Insect Antifeedants

INSECT ANTIFEEDANTS

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INSECT ANTIFEEDANTS

Opender Koul Insect Biopesticide Research Centre Jalandhar, India

CRC PR E S S Boca Raton London New York Washington, D.C.

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Library of Congress Cataloging-in-Publication Data Koul, Opender. Insect antifeedants / by Opender Koul. p. cm. Includes bibliographical references (p. ). ISBN 0-415-33400-4 (alk. paper) 1. Insect antifeedants. 2. Biological insecticides. 3. Insecticidal plants. I. Title SB931.K786 2004 632'.7--dc22 2004051077

This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission, and sources are indicated. A wide variety of references are listed. Reasonable efforts have been made to publish reliable data and information, but the author and the publisher cannot assume responsibility for the validity of all materials or for the consequences of their use. Neither this book nor any part may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, microfilming, and recording, or by any information storage or retrieval system, without prior permission in writing from the publisher. The consent of CRC Press LLC does not extend to copying for general distribution, for promotion, for creating new works, or for resale. Specific permission must be obtained in writing from CRC Press LLC for such copying. Direct all inquiries to CRC Press LLC, 2000 N.W. Corporate Blvd., Boca Raton, Florida 33431. Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation, without intent to infringe.

Visit the CRC Press Web site at www.crcpress.com © 2005 by CRC Press LLC No claim to original U.S. Government works International Standard Book Number 0-415-33400-4 Library of Congress Card Number 2004051077 Printed in the United States of America 1 2 3 4 5 6 7 8 9 0

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ACKNOWLEDGMENTS I thank Prof. Sukh Dev (India), Prof. Murray B. Isman (Canada), Prof. A. J. Mordue Luntz (UK), Prof. W. Kraus (Germany), Prof. L. M. Schoonhoven (Netherlands), and Dr. Michael J. Smirle (Canada) for critical reading and valuable suggestions on various chapters in this book. I also thank my students, particularly Gurmeet Singh for editorial assistance in arranging references.

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PREFACE In the recent past, the virtual dependence on neurotoxic chemicals to control pest insects has provided the impetus for studies into alternative methods of pest control that could avoid the environmental hazards associated with broad-spectrum insecticides. Overuse of synthetic insecticides that share a neurotoxic mode of action for pest management in agriculture, forestry, and managed landscapes has often induced negative impacts on natural enemies, pollinators, and other non-target organisms and often leads to the development of resistance. Fortunately new alternatives for pest control can be found within the large group of natural products or the synthetic derivatives thereof, which have the advantage of providing novel modes of action, therefore reducing the risk of cross-resistance. Naturally occurring mixtures of substances provide a multifactorial selective pressure on pests that also slows down the development of resistance. More important, research in this area has uncovered subtle but effective mechanisms of pest control, such as the behavior-modifying method of feeding deterrence. Therefore, the concept of using insect antifeedants as crop protectants is intuitively attractive. Most plant defensive chemicals discourage insect herbivory, either by deterring feeding and oviposition or by impairing larval growth, rather than by killing insects outright. One application of our understanding of plant defensive chemistry, then, is the identification of putative deterrent substances that could be isolated in sufficient quantities or synthesized for use as crop protectants. In fact, an insect antifeedant is a behavior-modifying substance that deters feeding through a direct action on peripheral sensilla in insects. This definition excludes chemicals that suppress feeding by acting on the central nervous system (following ingestion and absorption), or a substance that has sublethal toxicity to the insect. During the past three decades scores of compounds have been isolated from various natural sources, or semi-synthetic derivatives have been prepared that have the potential to inhibit feeding of a variety of insect species. However, all these studies are scattered through the biological and chemical literature, and it was felt necessary to assemble this data in the form of a comprehensive treatise on this expanding area of study and application that would aid investigators and lead them to more effective and desirable solutions to insect control. The present volume, therefore, is an attempt to compile all the data as a single text that deals specifically, as far as possible, with various aspects of insect antifeedants discussed in seven chapters. Chapter 1 introduces the subject with an emphasis on definitions and the role of antifeedants as a whole. Food selection among insect herbivores is a highly specialized phenomenon. While olfactory and physical aspects of plants or their organs can be important in insect host finding and acceptance, the choice of food is based primarily upon contact chemoreception of various allelochemicals. In particular, dietary experience has been found to influence the ability of insects to taste plant chemicals that may serve as signals of suitability or unsuitability. Certain dietary constituents appear to suppress the development of taste sensitivity to deterrents in an insect. Avoidance of allelochemicals, when looked at from a behavioral point of view, is the outcome of interactions with chemoreceptors characterized by an often-broad sensitivity spectrum of deterrents; therefore, Chapter 2 discusses the concepts and mechanisms involved in the process.

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In relation to the response of insects to these chemicals, the aspect of evaluation is important and accordingly various bioassay procedures have been developed, which are discussed in Chapter 3 and are mostly species specific. The overall picture, which emerges from various evaluations, shows that small structural variations can produce drastic changes in the activity profile of compounds. A critical examination of functional groups present in the active molecules provides crucial information about the optimal relative stereochemistry required to stimulate an antifeedant response in insects. The main aim of Chapter 4 is directed in this direction and generalizes sufficient structure-activity information within specific skeletal systems to allow rational modification of readily available feeding deterrents to be made into potential insect control agents. Commercialization aspects, practical applications, and conclusions drawn from various studies are discussed in Chapters 5 and 6. The last chapter is the monograph section, which presents relevant information on nearly 900 compounds (in alphabetical order) that is directly accessible. It has been the endeavor to give complete details on the latest structural information and biological data for those compounds that deter feeding of insects. I hope the book will prove useful to all those interested in promoting the cause of new pest control allelochemicals so that sustainability in agriculture systems and environmental protection for future generations is achieved.

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Dedicated to the memory of my mother Uma Koul

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ABOUT THE AUTHOR Opender Koul, Fellow of the National Academy of Agricultural Sciences and the Indian Academy of Entomology, is an insect toxicologist/physiologist/chemical ecologist and currently the Director of the Insect Biopesticide Research Centre, Jalandhar, India. After obtaining his Ph.D. in 1975 he joined the Regional Research Laboratory (CSIR), Jammu, and then became Senior Group Leader of Entomology at Malti-Chem Research Centre, Vadodara, India (1980–1988). He has been a visiting scientist at the University of Kanazawa, Japan (1985–1986), University of British Columbia, Canada (1988–1992), and Institute of Plant Protection, Poznan, Poland (2001). His extensive research experience concerns insect–plant interactions, spanning toxicological, physiological, and agricultural aspects. Honored with an Indian National Science Academy medal (INSA) and the Kothari Scientific Research Institute award, he has authored over 140 research papers and articles, and is the author or editor of the books Insecticides of Natural Origin, Phytochemical Biopesticides, Microbial Biopesticides, Predators and Parasitoids, Neem: Today and in the New Millennium, Integrated Pest Management: Potential, Constraints and Challenges, and Transgenic Crop Protection: Concepts and Strategies. He has also been an informal consultant to BOSTID, NRC of the United States at ICIPE, Nairobi.

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CONTENTS 1 Introduction........................................................................................................................1 References............................................................................................................................6 2 Concepts and Mechanisms ...............................................................................................9 Chemosensory System.......................................................................................................10 Stereoselective Perception.................................................................................................11 Mechanisms .......................................................................................................................14 GABA Antagonistic Mechanism.......................................................................................15 Biogenic Amine Inhibition Mechanism ............................................................................17 Mechanisms Related to Specific Allelochemicals ............................................................17 References..........................................................................................................................19 3 Bioassays...........................................................................................................................25 Leaf Disk Assay ................................................................................................................26 Artificial Diet Feeding.......................................................................................................29 Styropor Assay ..................................................................................................................31 Glass Fiber Disk Test ........................................................................................................31 Paper Towel Disk Test.......................................................................................................31 Wafer Assay.......................................................................................................................32 Electrophysiological Assay ...............................................................................................33 Other Miscellaneous Methods...........................................................................................34 Simulation Bioassay .....................................................................................................34 Dipteran Assays ............................................................................................................35 WireWorm (Melanotus Communis) Assay...................................................................36 Boll Weevil Assay.........................................................................................................36 Scale Insect Assay ........................................................................................................36 Sawfly Assay.................................................................................................................36 Leaf Beetle Assay .........................................................................................................37 Oral Dosing...................................................................................................................37 Field Trials ....................................................................................................................38 References..........................................................................................................................38 4 Structure-Activity Relationships....................................................................................43 Limonoids ..........................................................................................................................43 Quassinoids........................................................................................................................50 Diterpenes ..........................................................................................................................53 Sesquiterpenes ...................................................................................................................56 Monoterpenes ....................................................................................................................58 Coumarins..........................................................................................................................59 xi © 2005 by CRC Press LLC

Isoflavonoids ......................................................................................................................63 Alkaloids............................................................................................................................64 Maytansinoids....................................................................................................................65 Ellagitannins ......................................................................................................................65 Aristolochic Acids .............................................................................................................67 References..........................................................................................................................68 5 Commercialization...........................................................................................................73 References..........................................................................................................................77 6 Practical Applications and Conclusions........................................................................79 Conclusions........................................................................................................................82 References..........................................................................................................................83 7 Bioefficacy Monographs..................................................................................................85

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1 INTRODUCTION Research over the last 35 years has provided substantial evidence that plants and animals often produce substances that affect the growth, development, behavior, and distribution of other organisms. Such naturally occurring substances are called “allelochemicals.” The term “allelochemic” was first proposed by Whitaker and Feeny (1971) and has been defined as a chemical that is significant to organisms of a species different from its source for reasons other than food as such (Nordlund, 1981). In fact, the term allelochemical comes from many terms that have been designated for chemicals that convey information between organisms; “semiochemicals” is the umbrella term, which comprises both information-conveying chemicals and toxins. Dicke and Sabelis (1988) have rightly used the term “information conveying chemicals,” as they differ from general toxins and nutrients in that the former are not themselves detrimental or beneficial, but may be through the responses they elicit. Thus using the term “infochemicals” is based on: 1. Whether the interaction is intra- or interspecific (pheromone versus allelochemical) 2. Which costs and benefits fall to each of the two interacting organisms 3. The identity of the producer and the receiver Four major categories of allelochemicals have now been recognized: the allomones, kairomones, synomones, and apneumones. However, Whitman (1988) has added another category, in which neither interactant benefits, and called them antimones. There is also a possibility that one chemical that benefits an organism in one interaction may also have side effects in other interactions (Whitman, 1988). However, all terms are context specific rather than chemical specific. To be precise, “infochemicals” in the present context is appropriate and can be characterized as in Figure 1.1.

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INFOCHEMICALS

PHEROMONES

ALLELOCHEMICALS

1. (+, −) Pheromone Benefit to emitter

1. Allomone

2. Kairomone 2. (−, +) Pheromone Benefit to receiver

3. Synomone 4. Apneumone

3. (+, +) Pheromone Benefit to both

5. Antimone

FIGURE 1.1 Infochemical terminology.

The objective of this book is to explore the studies of insect antifeedants and accordingly deal with allelochemicals in general and allomones in particular. “Allomones” have been defined as substance(s) produced or acquired by an organism that, when it contacts an individual of another species in the natural context, evokes in the receiver a behavioral or physiological response that is adaptively favorable to the emitter but not to the receiver (Nordlund, 1981). As such, allomones are differentiated from pheromones because they mediate interspecific, rather than intraspecific interactions. Receiving organisms respond to allomones in a variety of ways. Subtle changes in behavior and physiology of the receiver can result in host-shifts in phytophages or parasites, or extended developmental times due to reductions in nutritional value of foodstuffs. At the other end of the spectrum, violent reactions leading quickly to injury and death are often the result of encounters with highly toxic defensive allomones. This tremendous diversity, coupled with the intensity of allomonemediated interspecific interactions, makes allomonal chemicals potential agents for insect pest control. Although allomones mediate a wide variety of complex interactions, allomonal chemicals fall into one of two basic categories. The first of these includes materials produced by the organisms and released into the environment, mostly volatile compounds that exert their influences at some distance from the emitter. For instance, it is well known that green plants release characteristic volatiles arising from the metabolism of leaf lipids such as linoleic acids, which by oxidative degradation produce a variety of 6-carbon alcohols and aldehydes. Such volatiles include a wide variety of short chain alcohol and aldehydes, ketones, esters, aromatic phenols, mono- and sesquiterpenes, and a host of other secondary metabolites. The second group of allomones includes compounds produced or acquired for defense, which remain in the body of the producer. This group includes toxins sequestered by insects for defense and the vast array of plant allelochemicals or secondary plant compounds. There are several characteristics required for the evolution of the ability of polyphagous insects (in category II) to use plant secondary metabolites as defense compounds. The main prerequisites for the evolution of unpalatability due to such compounds could be the:

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Feeding on a toxic plant thus having potential defense compounds in the insect’s diet Elimination of detoxification mechanism by inactivating detoxification enzymes so that defense compounds are not broken down Ability of compounds to move through the gut and reach the haemolymph Accumulation of defense compounds in the haemolymph against an osmotic gradient and retention of compounds through the stadium (Bowers, 1992)

In other words, the allomones are the phytochemicals produced from secondary metabolic pathways and are the major mechanisms by which plants are protected from excessive herbivory. Behavioral mechanisms provide a system of avoidance of non-host chemicals by which insects select their food, though the molecular basis for action of chemical deterrents on both gustatory and olfactory sensory systems in insects is only poorly understood. Among plant anti-herbivore chemistry, a strong link does not exist between feeding deterrence and internal toxicity in insects, suggesting that behavioral rejection is not an adaptation to ingested effects but more an outcome of deterrent receptors with wide chemical sensitivity (Mullin et al., 1991, 1994). Many of these substances are bitter, and acceptance of host plants by herbivores requires chemoreception of favorable levels of phagostimulants relative to antifeedants (Dethier, 1980). This restricts the application of a very liberal definition for an antifeedant, namely, “any substance that reduces consumption by an insect” to a more precise definition: “A peripherally mediated behavior-modifying substance (i.e., acting directly on the chemosensilla in general and deterrent receptors in particular) resulting in feeding deterrence” (Isman, 1994). This definition, however, excludes chemicals that suppress feeding by acting on the central nervous system (following ingestion or absorption), or a substance that has sublethal toxicity to the insect (Isman, 2002). Feeding deterrents with a wide diversity of structures are not known to directly interfere with insect taste cell responses to phagostimulants such as sugars (Lam and Frazier, 1991; Schoonhoven et al., 1992). Presently the mode of action of feeding modifying chemicals in insect gustatory systems is largely unknown (Frazier, 1992; Schoonhoven et al., 1992), though some molecular targets have been identified (Koul, 1997). Taste receptor proteins are only now beginning to be biochemically purified and cloned. The determination of the molecular basis for action of feeding deterrents in the insect gustatory system is thus a primary goal among basic and applied entomologists interested in insect–plant interactions or in the control of herbivore pests. According to the theory of biochemical coevolution it should be possible to develop an evolutionary pattern of antifeedants on the basis of their distribution in different plant families and their biosynthetic pathways. Accordingly it has been possible to draw an evolutionary scheme as shown in Figure 1.2 (modified from Harborne, 1988). However, the pattern of distribution varies among families. One plant family may concentrate on one type of deterrent molecule, like limonoids in the Rutales (Champagne et al., 1992) and also, within a family, individual members may have developed further barriers to feeding. For instance, it is clear that flavonoids in plants can modulate the feeding behavior of insects, though mechanisms associated with these behavioral responses are not clearly understood (Simmonds, 2001). Other families may diversify their deterrents; for example, non-protein amino acids (e.g., L-canavanine), alkaloids, cyanogens, and isoflavones are found in the Fabaceae. Plants produce all these and many varied compounds in the first instance as protective devices against insect feeding. Thus a majority of plant families rely on secondary plant metabolites for protection from phytophagous insects. One might surmise that within such a family the more advanced members are better protected than others. Berenbaum (1983) has pointed to

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Opender Koul Sesquiterpene Lactones Alkaloids

Flavones

Monoterpene Lactones HERBACIOUS Sesquiterpenes Cardiac Glycosides

Non-protein Aminoacids

Cucurbitacins

Limonoids

WOODY

Diterpenes Saponins

Quassinoids

Polyacetylenes

Coumarins

ANGIOSPERMS -------------------------------------------------------------------------------------------------------------------Ecdysteroids Tannins Cyanogens Juvenoids

FATTY ACID

GYMNOSPERMS FERNS

TERPENOID

PHENOLICS

NITROGEN

BIOSYNTHETIC PATHWAYS

FIGURE 1.2 Possible evolutionary scheme of insect antifeedants in plants (modified from Harborne, 1988).

good evidence in the Apiaceae where plant defense is based on hydroxycoumarins, linear furanocoumarins, and angular furanocoumarins, which are biosynthetically and toxicologically related. It is also evident from various studies that as a result of coevolutionary pressures, plants have a startling number of plant chemicals including chromenes, polyacetylenes, saponins, quassinoids, cuccurbitacins, cyclopropanoid acids, phenolics, alkaloids, various types of terpenes, and their derivatives, and each insect species may process these allomones in a thoroughly idiosyncratic way, so that the same compound may have very different fates and consequences in different species of insects (Koul, 1993; Blum et al., 1987). These various insect–plant interactions are consistent with the idea of reciprocal evolutionary interactions based on secondary metabolites. This, however, could be related to the evolution of deterrent

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receptors in insects, too. There is a clear indication that no two insect species are equipped with an identical sensory system. Each species has a unique sensory window, which can discriminate between host and non-host plants (Schoonhoven, 1982). Even in very closely related species the chemical senses show striking differences (Drongelen, 1979). It can be visualized from such information that the contact chemical senses may in evolutionary terms be easily adapted to changing circumstances, as has been well evidenced in two strains of Mamestra brassicae in response to sinigrin and naphtyl-β-glucoside (Wieczorek, 1976). It can also be visualized that insect feeding deterrents may be perceived either by stimulation of specialized deterrent receptors or by distortion of the normal function of neurons, which perceive phagostimulating compounds. Some sugars are very important components of an insect’s sustained feeding; the inhibition of the receptors is an effective antifeedant action. Some antifeedants influence the feeding activity through a combination of the two principal modes of action mentioned above. Initial discoveries of antifeedant chemicals were simply made by chance when organometallic compounds and a few insecticides were found to reduce insect feeding (Ascher and Rones, 1964; Jermy and Metolcsy, 1967). This clearly emphasizes the point that many synthetic compounds could be potential antifeedants for insect pests (Koul, 1993), of course in addition to the allomones or their derivatives from natural sources. As early as 1932 Metzger and Grant tested about 500 plant extracts against Popillia japonica, though results were not substantially encouraging. Pradhan et al. (1962) evaluated extracts of the Indian neem tree, Azadirachta indica, which prevented feeding by the desert locusts, and today nearly 900 compounds have been identified to possess feeding deterrence against insects (see Chapter 7), though terrestrial plants produce a diverse array of secondary metabolites, likely more than 100,000 unique compounds (Isman, 2002). In addition to various compounds isolated or synthesized as insect antifeedants, a number of studies demonstrate the antifeedant efficacy in metabolite mixtures of plant essential oils or total extracts against a variety of insect species. In recent years studies have revealed the antifeedant potential of plant essential oils against post-harvest pests, aphids, thrips, lepidopterans, termites, and mite pests (Hori, 1999; HouHouaMin et al., 2002a, 2002b; Koschier et al., 2002; Maistrello et al., 2003). Similarly, during the past few years ample emphasis has been in demonstrating the antifeedant efficacy in total plant extracts (Mancebo et al., 2000a, 2000b; Wang et al., 2000; Jannet et al., 2001; Lababidi and Koudseieh, 2001; Schlyter, 2001; Wheeler and Isman, 2001; Mehta et al., 2002; Jayasinghe et al., 2003) as they seem to exhibit the activity as multicomponent systems. However, it is also well known that antifeedants show interspecific variability (Chapman, 1974; Schoonhoven and Jermy, 1977; Isman, 1993). Such interspecific differences, as shown for many insect species, encourage the need to search selectively for specific feeding deterrents. Van Beek and deGroot (1986) have suggested three considerations for the selection of plants that are to be evaluated for antifeedant activity: 1. The species can be selected at random. 2. They could be selected on chemotaxonomic bases. 3. The species can be selected on the basis of ethnobotanical or entomological data. All three methods have been used, and the second method has led to the most frequent successes. It is, therefore, necessary to focus attention on particular chemical groups occurring naturally in various sources, or environmentally safe synthetics, and thus obtain a large number of active antifeedant compounds, which could be successfully introduced in Insect Pest Management (IPM) programs. However, simultaneous to such developments it is necessary to understand the concepts and mechanisms involved in antifeedant interactions. It is

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also important to point out here that not much success has been achieved so far in establishing a good commercial antifeedant for crop protection. However, the commercial potential and the drawbacks will be discussed in Chapter 6. Recently, it has also been demonstrated that neuropeptide-based pesticides potentially offer levels of activity, specificity, and environmental compatibility absent in conventional insecticides. However, neuropeptides are generally poor candidates for insecticides because they do not easily penetrate the cuticle and degrade rapidly in the environment and insect gut. Manduca sexta allatostatin (Manse-AS) regulates juvenile hormone biosynthesis in moths and has myoregulatory action on the gut. Moreover, Manse-AS produces marked reductions in feeding and growth when injected into larvae of the tomato moth, Lacanobia oleracea. Snowdrop lectin (GNA) is detectable in the haemolymph of larvae following oral administration. To determine whether GNA could transport neuropeptides across the gut, a recombinant expression system was used to produce a GNA/Manse-AS fusion protein (FP). Following expression in Escherichia coli, purified FP was incorporated in an artificial diet and offered to tomato moth larvae. Intact FP appeared in the haemolymph following oral administration, which resulted in an almost total cessation of feeding and growth by larvae exposed to the FP diet. These results offer the possibility of developing a whole range of novel, orally active, target-specific antifeedants based on insect neuropeptides (Edwards et al., 2002).

REFERENCES Ascher, K.R.S. and Rones, G. (1964) Fungicide has residual effect on larval feeding. Int. Pest Control., 6, 6–9. Berenbaum, M. (1983) Coumarin and caterpillars, a case for coevolution. Evolution, 37, 163–179. Blum, M.S., Whitman, D.W., Severson, R.F., and Arrendale, R.F. (1987) Herbivores and toxic plants: evolution of a menu of options for processing allelochemicals. Insect Sci. Applic., 8, 459–563. Bowers, M.D. (1992) The evolution of unpalatability and the cost of chemical defense in insects. In B.D. Roitberg and M.B. Isman (eds.), Insect Chemical Ecology: An Evolutionary Approach, Chapman & Hall, New York, pp. 216–244. Champagne, D.E., Koul, O., Isman, M.B., Towers, G.H.N., and Scudder, G.G.E. (1992) Biological activity of limonoids from the rutales. Phytochemistry, 31, 377–394. Chapman, R.F. (1974) The chemical inhibition of feeding by phytophagous insects. A review. Bull. Entomol. Res., 64, 339–363. Dethier, V.G. (1980) Evolution of receptor sensitivity to secondary plant substances with special references to deterrents. Am. Nat., 115, 45–66. Dicke, M. and Sabelis, M.W. (1988) Infochemical terminology: should it be based on costbenefit analysis rather than origin of compounds? Funct. Ecol., 2, 131–139. Edwards, J.P., Fitches, E.C., Audsley, N., and Gatehouse, J.A. (2002) Insect neuropeptide fusion proteins—a new generation of orally active insect control agents. In Pests-anddiseases, Proceedings BCPC Conf., Brighton, UK, pp. 25–31. Frazier, J.L. (1992) How animals perceive secondary plant compounds. In G.A. Rosenthal and M.R. Berenbaum (eds.), Herbivores: Their Interaction with Secondary plant Metabolites, Evolutionary and Ecological Processes, 2nd edition, Vol. 2, Academic Press, San Diego, pp. 89–134. Harborne, J.B. (1988) Introduction to Ecological Biochemistry. Academic Press, New York.

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Hori, M. (1999) Antifeeding, settling inhibitory and toxic activities of Labiatae essential oils against the green peach aphid, Myzus persicae (Sulzer) (Homoptera:Aphididae). Appl. Entomol. Zool., 34, 113–118. Hou, HouaMin, Zhang Xing, Hou, H.M., and Zhang, X. (2002a) Effect of essential oil of plants on three lepidopterous insects: antifeeding and growth inhibition. Acta Phytophylacica Sinica, 29, 223–228. Hou, HouaMin, Feng, J.T., Chen AnLiang, Zhang Xing, Hou, H.M., Feng, J.T., Chen, A.L., and Zhang, X. (2002b) Studies of the bioactivities of essential oils against insects. Nat. Prod. Res. Develop., 14, 27–30. Huang, Y., Lam, S.L. and Ho, S.H. (2000) Bioactivities of essential oils from Elletaria cardemomum (L.) Maton to Sitophilus zeamais Motschulsky and Tribolium castaneum (Herbst.). J. Stored Prod. Res., 36, 107–117. Isman, M.B. (1993) Growth inhibition and antifeedant effects of azadirachtin on six noctuids of regional economic importance. Pestic. Sci., 38, 57–63. Isman, M.B. (1994) Botanical insecticides and antifeedants: New sources and perspectives. Pestic. Res. J., 6, 11–19. Isman, M.B. (2002) Insect antifeedants. Pestic. Outlook, 13, 152–157. Jannet, H.B., Skhiri, F., Mighri, Z., Simmonds, M.S.J., and Blaney, W.M. (2001) Antifeedant activity of plant extracts and a new natural diglyceride compounds isolated from Ajuga pseudoiva leaves against Spodoptera littoralis larvae. Industr. Crops Prod., 14, 213–222. Jayasinghe, U.L.B., Kumarihamy, B.M.M., Bandara, A.G.D., Waiblinger, J., and Kraus, W. (2003) Antifeedant activity of some Sri Lankan plants. Nat. Prod. Res., 17, 5–8. Jermy, T. and Metolcsy, G. (1967) Antifeedant effects of some systemic compounds on chewing phytophagous insects. Acta Phytopath. Acad. Sci. Hung., 2, 219–224. Koul, O. (1993) Plant allelochemicals and insect control: An antifeedant approach. In T.N. Ananthakrishanan and A. Raman (eds.), Chemical Ecology of Phytophagous Insects, IBH & Oxford Publishers Pvt. Ltd., New Delhi, pp. 51–80. Koul, O. (1997) Molecular targets for feeding deterrents in phytophagous insects. In A. Raman (ed.), Ecology and Evolution of Plant Feeding Insects in Natural and Man-Made Environments, International Scientific Publications, New Delhi, pp. 123–134. Koschier, E.H., Sedy, K.A., and Novak, J. (2002) Influence of plant volatiles on feeding damage caused by the onion thrips, Thrips tabaci. Crop Protection, 21, 419–425. Lababidi, M.S. and Koudseieh, S. (2001) Laboratory evaluation of the biological activity of several plant extracts against adults of the two-spotted spider mite, Tetranychus urticae Koch (Acari:Tetranychidae). Arab J. Plant Prot., 19, 86–91. Lam, P.Y.-S. and Frazier, J.L. (1991) Rational approach to glucose taste chemoreceptor inhibition as novel insect antifeedants. In D.R. Baker, J.G. Fenyes, and W.K. Moberg (eds.), Synthesis and Chemistry of Agrochemicals II, ACS Symp. Ser. 443, American Chemical Society, Washington, D.C., pp. 400–412. Maistrello, L., Henderson, G., and Laine, R.A. (2003) Comparative effects of vetiver oil, nootkatone, and disodium octaborate tetrahydrate on Coptotremes formosanus and its symbiotic fauna. Pest Managm. Sci., 59, 58–68. Mancebo, F., Hilje, L., Mora, G.A., and Salazar, R. (2000a) Antifeedant activity of plant extracts on Hypsipyla grandella larvae. Rev. Fores. Centroamericana, 31, 11–15. Mancebo, F., Hilje, L., Mora, G.A., and Salazar, R. (2000b) Antifeedant activity of Quassia amara (Simaroubaceae) extracts on Hypsipyla grandella (Lepidoptera:Pyralidae) larvae. Crop Prot., 19, 301–305.

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Mehta, P.K., Sood, A.K., Parmar, S., and Kashyap, N.P. (2002) Antifeedant activity of some plants of North-Western Himalayas against cabbage caterpillar, Pieris brassicae (L.). J. Entomol. Res., 26, 51-54. Metzger, F.W. and Grant, D.H. (1932) Repellency of the Japanese beetle of extracts made from plants immune to attack. Tech. Bull. USDA No. 299, 21 pp. Mullin, C.A., Mason, C.H., Chou, J., and Linderman, J.R. (1991) Phytochemical antagonism of γ-aminobutyric acid based resistance in Diabrotica. In C.A. Mullin and J.G. Scott (eds.), Molecular Mechanisms of Insecticide Resistance: Diversity Among Insects, ACS Symp. Ser. 505, American Chemical Society, Washington, D.C., pp. 288–308. Mullin, C.A., Chyb, S., Eichenseer, H., Hollister, B., and Frazier, J.L. (1994) Neuroreceptor mechanism in insect gustation, a pharmacological approach. J. Insect Physiol., 40, 913–931. Nordlund, D.A. (1981) Semiochemicals: A review of the terminology. In D.A. Nordlund, R.L. Jones, and W.J. Lewis (eds.), Semiochemicals, Their Role in Pest Control, Plenum Press, New York, pp. 13–28. Pradhan, S., Jotwani, M.S., and Rai, B.K. (1962) The neem seed deterrent to locusts. Indian Farming, 12, 7–11. Schoonhoven, L.M. (1982) Biological aspects of antifeedants. Entomol. Exp. Appl., 31, 57–69. Schoonhoven, L.M. and Jermy, T. (1977) A behavioural and electrophysiological analysis of insect feeding deterrents. In N.R. Mcfarlane (ed.), Crop Protection-Their Biological Evaluation, Academic Press, London, pp. 133–146. Schoonhoven, L.M., Blaney, W.M., and Simmonds, M.S.J. (1992) Secondary coding of feeding deterrents in phytophagous insects. In E.A. Bernays (ed.), Insect Plant Interactions, Vol. 4, CRC Press, Boca Raton, Florida, pp. 59–79. Schlyter, F. (2001) Antifeedants as plant protection against Hylobius pine weevils. Vaxtskyddsnotiser, 65, 47–53. Simmonds, M.S.J. (2001) Importance of flavonoids in insect–plant interactions: feeding and oviposition. Phytochemistry, 56, 245–252. Van Beek, T.A. and de Groot, A.C. (1986) Terpenoid antifeedants Part I. An overview of terpenoid antifeedants of natural origin. Recuril des Trav. Chimiq. Des Pays-Bas, 105, 513–527. Van Drongelen, W. (1979) Contact chemoreception of host plant specific chemicals in larvae of various Yponomenta species (Lepidoptera). J. Comp. Physiol., 134A, 265–279. Wang, S.F., Liu, A.Y., Ridsdill-Smith, T.J., and Chisalberti, E.L. (2000) Role of alkaloids in resistance of yellow lupin to red legged earth mite Halotydeus destructor. J. Chem. Ecol., 26, 429–441. Wheeler, D.A. and Isman, M.B. (2001) Antifeedant and toxic activity of Trichilia americana extract against the larvae of Spodoptera litura. Entomol. Exp. Appl., 98, 9–16. Whitaker, R.H. and Feeny, P.P. (1971) Allelochemics: chemical interactions between species. Science, 171, 757–770. Whitman, D.W. (1988) Allelochemical interactions among plants, herbivores and their predators. In P. Barbosa and D.K. Letourneau (eds.), Novel Aspects of Insect–Plant Interactions, John Wiley, pp. 11–64. Wieczorek, H. (1976) The glycoside receptor of the larvae of Mamestra brassicae L. (Lepidoptera: Noctuidae). J. Comp. Physiol., 106A, 153–176.

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2 CONCEPTS AND MECHANISMS Food selection among insect herbivores is a highly specialized phenomenon. While olfactory and physical aspects of plants or their organs can be important in insect host finding and acceptance (Miller and Strickler, 1984), the choice of food is primarily based upon contact chemoreception of various allelochemicals (Frazier, 1986; Stadler, 1992). In particular, dietary experience has been found to influence the ability of insects to taste plant chemicals that may serve as signals of suitability or unsuitability. Certain dietary constituents appear to suppress the development of taste sensitivity to deterrents in an insect (Renwick, 2001). Avoidance of allelochemicals, when looked at from a behavioral point of view, is the outcome of interactions with chemoreceptors characterized by an often-broad sensitivity spectrum of deterrents (Mullin et al., 1994). According to Schoonhoven et al. (1992) there are four basic reasons why the chemosensory perception of feeding deterrents by phytophagous insects warrants special attention: 1. Feeding deterrents are apparently more important in host-plant recognition than phagostimulants. 2. A huge number of feeding deterrents exist with variable molecular structures adding to their diversity. 3. There are fewer deterrent receptors. 4. Different deterrents may elicit different behavioral reactions, indicating the presence of a differential sensory coding system. On the whole the mode of action of feeding modifying chemicals in insect chemoreceptor systems is largely unknown, and no biochemically purified or cloned taste receptor proteins

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have been identified. However, a number of molecular targets for feeding deterrents have been identified (Koul, 1997), and there is evidence to show the existence of several sensory mechanisms involved. Therefore, to understand the concepts and mechanisms of feeding deterrents in an insect gustatory system, a search for candidate neuroreceptors and various behavioral end points is required. To achieve this, at first place one must look into the chemosensory equipment involved in the process.

CHEMOSENSORY SYSTEM The surface of the insect body is richly supplied with sensilla of various shapes and densities. The sensillum is the structural unit from which the majority of insect sensory organs are derived. Ectodermal in origin, a sensillum develops by differentiation from a mother epidermal cell. It consists of cuticular parts, one or more sense cells, and two or more sheath cells. The sense cells vary in number from 1 to 40 or more and have large nuclei located below the epidermis. These bipolar sense cells send their dendrites to the cuticular parts where their form, ultrastructural features, and methods of attachment are characteristic for cells of different modalities. Their axons extend into the sensory nerve parallel with other sensory axons, often extending directly to the central nervous system (CNS) before making synaptic connections to second-order neurons. Thus, they are primary sense cells that contain both a sensory receptor area on their dendrites and an impulse-conducting membrane along their axons. Usually sheath cells vary in number and are of three types: the basal, the outer, and the inner sheath cells. These cells have tight and gap junctions among them and form a sort of insulating barrier between the extracellular space surrounding the dendrites and the haemolymph space below the epidermis (Kuppers and Thurm, 1982). The cuticular projections of insect sensilla are the most visible portions, and their size, shape, and position have been the basis for classifying them. With various microscopic examinations and impulse recording techniques, various features of structure and function have been demonstrated. Insect sensilla on the outside of the body consist of the major types based on shape of the cuticular part, the presence or absence of pores, and the type of attachment to the cuticle (Frazier, 1985). They have been classified as: • • • • • •

Sensillum in a flexible socket with a single sense cell containing a tubular body Sensillum without a flexible socket containing a sense cell with lamellated dendrite Uniporous sensillum in a flexible socket containing one cell with a tubular body and one or more cells with dendrites extending to the terminal pore Uniporous sensillum without a flexible socket containing two or more cells with unbranched dendrites Multiporous sensillum with a single wall and multiple cells with branched dendrites Multiporous sensillum with a double wall and multiple cells with unbranched dendrites

Out of these six major types the sensilla that possess only a single terminal pore (thickwalled) are of gustatory nature and are concentrated on the mouth parts, though taste hairs also occur on tarsae, antennae, and ovipositors. They possess flexible sockets; 2 to 20 sensory cells, 1 dendrite with tubular unbranched body or inflexible sockets; 2 to 9 sensory cells and unbranched dendrites. They are usually uniporus. However, uniporous sensilla with inflexible sockets are fewer in number, but dome-shaped sensilla occur often in the preoral cavity, where they serve to monitor the food being eaten.

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Lepidopterous larvae have been observed to carry in each maxilla a palpus and a galea, the latter carrying two sensilla styloconica, non-socketed pegs with an apical papilla. These taste hairs are innervated by four bipolar neurons, the dendrites of which extend through the length of the hollow cuticular peg ending just below the pore at the tip (i.e., within a few milliseconds of diffusion time from the external chemical environment) (Schoonhoven, 1987; Descoins, 2001). The tip of the maxillary palp is covered with eight sensilla basiconica. The palp tip sensilla are innervated by 14 to 19 neurons in total (Schoonhoven and Dethier, 1966). This number, however, varies in different insect species (Devitt and Smith, 1982). As most of these sensilla are gustatory in nature, they are also involved in food recognition (Descoins, 2001). Palpation of the intact leaf surface, prior to biting activity, is related to contact chemoreception during which chemicals on the leaf cuticle are perceived (Devitt and Smith, 1985). An epipharyngeal taste sensillum in Leptinotarsa decemlineata larvae was studied using electron microscopy, which showed that the sensillum is innervated by five neurons. Electrophysiological experiments showed that one of these cells responds to water, a second to sucrose, and a third to two feeding deterrents that were also effective in a behavioral test. The response of the sucrose-sensitive cell was strongly inhibited by one of the two feeding deterrents and only slightly by the other feeding deterrent. It was concluded that probably both the response of the deterrent cell and peripheral interactions exerted by feeding deterrents on the sucrose-sensitive cell determine the potency of feeding deterrents. These results provide a physiological basis for the hypothesis that the presence or absence of feeding deterrents in potential food plants is a decisive cue in food plant selection by L. decemlineata larvae (Messchendorp et al., 1998). However, differential neurosecretory response of this insect species has also been recorded, for instance, against glycoalkaloids (Hollister et al., 2001). Thus one can easily surmise that gustatory chemosensilla must be regulating feeding behavior. It is obvious that many cells furnish information during the feeding sequence. In grasshoppers, for instance, receptor complement is large in number and low in specificity, and in caterpillars the number is low and relatively high in specificity (Frazier, 1986). In both extremes there is, however, redundancy among chemosensory cells, both with respect to specificity as well as overlap of sensitivity ranges of individual receptor cells (Blom, 1978). Obviously it is vital to have extensive and dependable information about plant allelochemicals that reduce or inhibit feeding. This link between single chemosensory cell input and behavioral output must be known before we are able to correlate the effects of allelochemicals on single cells in electrophysiological studies with their effects on the feeding behavior of the whole insect (Frazier, 1986).

STEREOSELECTIVE PERCEPTION Antifeedant properties of a plant compound may be revealed either by direct observation or by using electrophysiological methods that need thorough understanding of an insect’s chemoreceptory system. The latter procedure provides information on sensory mechanisms underlying the perception of antifeedant chemicals. However, no two insects possess fully identical chemoreceptory systems, but rather show different responses to various stimuli. Consequently, plant compounds may evoke different behavioral reactions even in closely related insect species (Schoonhoven, 1987). According to Schoonhoven (1988) life at a macroscopic scale usually presents itself in symmetrical forms. At the molecular level, however, asymmetry prevails. Nature often produces only one type of a stereospecific molecule and not its stereoisomer(s). Since chemoreception is a process of molecular interactions, the phenomenon of stereoisomerism may have consequences for the process of stimulus

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recognition. Therefore, the question arises: What is the role of stereospecificity of insect chemoreceptors vis-a-vis antifeedants? As mentioned above, the sense of taste in insects is localized in specialized receptors on the mouthparts, on the preoral cavity, on the tarsi, and on the antennae—often at several of these sites in the same insect. Extensive studies performed mainly on blowfly (Dethier, 1976) and lepidoteran larvae (Schoonhoven, 1987) have shown that receptors are usually not highly specific, and responses could be multineural. A correlation of the electrophysiological response with behavioral discrimination in caterpillars has provided evidence supporting the idea that patterns of multireceptor activity constitutes the basic code for recognition and discrimination. The sensory code may be altered due to the stimulation of specialized receptors or modulation of the activity of receptors tuned to other compounds. In lepidopteran larvae several specialized deterrent receptors have been described that respond to various alkaloids, phenolic compounds, and glycosides and that inhibit food intake. The deterrent receptors in different species often overlap in their sensitivity spectra, but show at the same time characteristic interspecific variations (Schoonhoven, 1982). Feeding deterrents may also change the activity of receptors that signal the presence of feeding stimulants, for instance when suppressing sugar receptors, and thereby act as strong antifeedants (Kennedy and Halpern, 1980). Azadirachtin, a terpenoid isolated from the neem tree, stimulates a deterrent receptor in a number of herbivorous insects (Schoonhoven, 1988), but appears to suppress sugar and inositol receptors in other species (Schoonhoven, 1988). On the whole, several specialized deterrent receptors have been described mainly in lepidopteran larvae. For instance, Bombyx mori possesses a bitter receptor that is located in one of the two sensilla styloconica on the maxilla and responds to various alkaloids acting as feeding inhibitors (Ishikawa, 1966) or responds to limonoid inhibitors, in the case of Helicoverpa armigera and H. assulta (Tang et al., 2000). Pieris brassicae larvae and several other lepidopteran species have one or more deterrent receptors, which overlap in their sensitivity spectra (Schoonhoven, 1982; Chapman, 1982). Colorado beetles also have deterrent receptors in their tarsal sensilla, responding to various solanaceous plant alkaloids (Sturckow, 1959). Specific deterrent receptors are also present in the preoral cavity of lepidopteran larvae (Ma, 1972; de Boer et al., 1977). Electrophysiological studies of Blaney (1980) emphasize the fact that deterrent receptors cannot be of a single and simple category. Therefore, even today the conclusion of Dethier (1980) that in insects with few receptors, multiple receptor sensitivity occurs and that “there is no generalized deterrent receptor,” seems to be highly plausible. As it is clear now that deterrent receptors vary from species to species, it won’t be an exaggeration to conclude that the contact chemical senses may in evolutionary terms be easily adapted to changing circumstances (Schoonhoven, 1982). Receptor sensitivity and specificity, however, is genetically determined, and changes in them apparently occur by a gradual replacement of certain receptor sites in the dendritic membrane by other types of sites, which bind different stimulants. For example, Wieczorek (1976) showed that the deterrent cell in two strains of Mamestra brassicae show quantitative differences in their response to some chemicals (Table 2.1), which may be explained by a different ratio between two types of receptor sites present in the receptor membrane. As shown in Table 2.1, one strain is very sensitive due to the presence of many sinigrin receptor sites, whereas the other strain is more easily stimulated by naphtyl-β-glucoside (Wieczorek, 1976). This is consistent with the model of Bernays and Chapman (1994), which suggests that differences in taste sensitivity to deterrent compounds could account for the difference in host range. It is also possible that diet breadth has a direct link with sensitivity of the deterrent receptor cells. For instance, genetic differences in the sensitivity of the deterrent

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TABLE 2.1 Sensitivity (in impulses/sec.) of a deterrent receptor to a standard concentration of sinigrin and 1-naph-β-glucoside in two strains of Mamestra brassicae (calculated from Wieczorek, 1976). Strain

Response

1 Sinigrin

16–21 Imp. Freq.

2

21–30

1 1-naph-β-glucoside

38–46 Imp. Freq.

2

23–29

receptor cells of Bombyx mori in relation to diet breadth (Asaoka, 1994) imply that the effect could not be peripheral; however, the same interpretation does not hold true for Heliothis species and suggests central nervous system mediated differences (Bernays et al., 2000). Reduced feeding on deterrent diets is, in fact, a consequence either of rejection without any ingestion or of rejection following some ingestion. Rejection without ingestion indicates that deterrent compound is detected by chemoreceptors on the mouthparts. Rejection following some ingestion apparently results from the accumulation of sensory information, since deterrent receptors sometimes adapt relatively slowly (Schoonhoven et al., 1998). There could be post-ingestive feedbacks that allow limited intake (Bernays et al., 2000). An intriguing question concerns the origin of deterrent receptors. It has been suggested that herbivorous insects, rather than evolving receptors for some specific deterrents, have developed from a “common chemical sense,” resulting in a receptor type that is sensitive to a wide variety of compounds, even including chemicals to which a particular species has never been exposed before (Dethier, 1980). It may be concluded from state-of-the-art studies that insect deterrent receptors cannot be considered as a primitive or uniform type of receptor, but rather as compound receptor types with a high degree of plasticity. According to Schoonhoven (1982) this plasticity on the one hand insures that the insect may quickly adapt to changes in its environment, but maintain the capacity to recognize unpalatable plants, and on the other hand, has led to considerable divergence resulting in no two insects being identical. In terms of CNS interpretation of the sensory code, feeding activity obviously requires motor output from the CNS, whereas the presence of feeding deterrents signaled via chemosensory input may inhibit feeding motor output, leading to a refusal to eat (Ma, 1972). Presently it is difficult to study the process as underlying the evaluation of sensory input by the CNS, and resulting in either continuation or cessation of feeding activity. However, the sensory inputs can be analyzed and the principles upon which central neural integration is based can be hypothesized. Some basic considerations put forth are: • • •

The gustatory sense has a leading role in feeding activity. The epipharyngeal organs do not add new information to that of the maxillary hairs. Sensory input from the maxillae is sent to the suboesophageal ganglion, that from the epipharyngeal organ to the tritocerebrum. The message indicating whether a plant is acceptable or not must be hidden in the sensory pattern it evokes (Schoonhoven, 1987).

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If the CNS is able to read this message, it is in principle also decipherable to us, and accordingly some messages may permit feeding activity and others may not. Sensory coding of feeding deterrents is based upon neural activity in one or more neurons. Three basic types of sensory coding are known (Schoonhoven et al., 1992): 1. Labeled lines: Each neuron conveys a specific message, which can be understood by the CNS without additional information from other neurons. 2. Across-fiber patterns: The message is contained in a neural activity pattern, transmitted by two or more receptors, possessing different stimulus spectra. 3. Temporal patterns: Stimulus quality affects nerve impulse interval patterns and adaptation rates, which may contain additional information. These coding principles could be cited in several cases and often occur in combination in insects (Dethier and Crnjar, 1982; Schoonhoven and Blom, 1988). A temporary distortion of such sensory codes can result in the inhibition of feeding. When in Leptinotarsa decemlineata the responses were compared between host and non-host potato saps. The response patterns for the non-host stimuli appeared to be considerably less consistent than the patterns evoked by the sap from the host plant (Mitchell et al., 1990; Schoonhoven et al., 1992). This suggests that such variable patterns are interpreted by the CNS as “nonsense,” with the result that no feeding or only limited feeding occurs, a pattern that has also been observed in various lepidopteran larvae (Simmonds and Blaney, 1990). Several chemicals, including some heavy metal ions, may distort the functioning of chemoreceptors in such a way that, even in the presence of an acceptable plant, the neural acceptance profile that the CNS requires for initiating feeding behavior is not evoked (Schoonhoven, 1987; Schoonhoven and Jermy, 1977).

MECHANISMS Secondary plant substances are in principle noxious because they interfere with the normal structure and function of insect cells and thus disturb their integrity. Thus insects, like other animals, have developed various mechanisms to reduce or prevent harmful effects of secondary plant substances when contacting them or after ingesting them (Brattsten and Ahmad, 1986). As we have seen, chemoreceptors in insects are primary sense cells and thus true neurons generally protected from the deleterious effects of secondary plant compounds. This is supported by the fact that insects have sensory neurons that respond to sugars, amino acids, or salts and function normally despite the presence of these host-specific noxious compounds, as was demonstrated in the case of polyhydroxy alkaloids against Spodoptera and Helicoverpa species (Simmonds et al., 1990). If some receptor cells have retained their primordial sensitivity to different kinds of secondary plant compounds, they would be ideally suited to signal the presence of chemicals to be avoided. Thus, the primitive, unmodified taste cell may be considered as the primordial deterrent receptor, which still possesses a sensitivity to odd plant substances originally shown by all primitive neurons. That does not mean that the present-day deterrent receptors are unchanged and wholly identical to their ancestral neural cell type. The modern deterrent receptors, while retaining sensitivity to various secondary plant compounds, have developed a physiological mechanism, which protects them against the harmful effects of their adequate stimuli. Not only has the basic sensitivity to secondary plant substances been preserved in these receptors, it also became connected to the action potential generating system, resulting in a change of impulse frequency upon stimulation (Schoonhoven, 1991). Thus, in contrast

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to sugar and salt receptors, deterrent receptors have preserved their general sensitivity, which has been linked to a neural response mechanism. In fact, all lepidopteran larvae possess a pair of maxillary palps that “drum” the surface of foods during feeding. These chemosensory organs contain over 65 percent of a larva's taste receptor cells, but their functional significance remains largely unknown. Their role in rejection of plant allelochemicals was examined, using the tobacco hornworm, Manduca sexta, as a model insect and an extract from a plant species, Grindelia glutinosa, as a model stimulus. This system was selected because hornworms reject foods containing Grindelia extract, and because preliminary studies indicated that their maxillary palps respond to this extract. It was hypothesized that Grindelia extract elicits rejection through stimulating (i) olfactory receptor cells, (ii) taste receptor cells, (iii) oral mechanoreceptors, and (iv) a post-ingestive response mechanism. The results were consistent only with hypothesis (ii); larvae approached Grindelia-treated diets without apparent hesitation, but rejected it within 6 seconds of initiating biting. Grindelia-treated solutions stimulated taste receptor cells in the maxillary palp, but not the other gustatory chemosensilla, and ablating the maxillary palps eliminated rejection of Grindelia-treated diets. The results demonstrate that taste receptor cells in the maxillary palps mediate rejection of Grindelia extract and provide the first direct evidence for a role of maxillary palps in rejection of plant allelochemicals (Glendinning et al., 1998). The possibility exists that insects use some other codes for taste quality, such as assessment of the temporal sequence of firing, which gives a continuous evaluation of the activity of individual neurons. It is also likely that simultaneous evaluation of inputs from different neurons allows contradictory signals, indicating the presence of phagostimulants or antifeedants, and is assessed concurrently (Schoonhoven, 1987). In addition to these neural mechanisms, it should be mentioned that some other targets are also vulnerable to antifeedants, like γ-amino butyric acid (GABA) antagonistic mechanisms, biogenic amine inhibition, and so on.

GABA ANTAGONISTIC MECHANISM GABA and related aminobutyric acids are known to stimulate feeding and evoke taste cell responses among herbivorous insects of various taxa, like Orthoptera, Homoptera, Coleoptera, and Lepidoptera (Mullin et al., 1994). However, it has also been established that allelochemicals antagonize GABA phagostimulants, like the isoquinoline alkaloid papavarine does in the Colorado potato beetle, thereby inducing feeding deterrence (Mitchell, 1987). GABAgated chloride channels respond to many classes of chemicals in insects (Sattelle, 1990; Anthony et al., 1993). The antagonism of GABA binding allows increased depolarization within an excitable cell and functions at both the neuromuscular junction and central synapses within the nervous system of insects. The present view is that inhibitory GABAA (Cl– conducting) receptors belong to a gene superfamily of ligand-gated ion channels that include excitatory nicotinic acetylcholine (Na+, K+) and inhibitory glycine (Cl–) receptors (Anthony et al., 1993). In turn, the α-carboxylated and precursor form of GABA, glutamic acid, gates a more distantly related family of both excitatory K+/Na+ and inhibitory Cl– channels (Darlison, 1992; Sattelle, 1992). On the whole it has been shown that the GABAA and glycine receptor complexes must incorporate two or three different four-transmembrane-domain subunits (Mullin et al., 1994). Association of GABA/glycine receptors with sensory systems has been demonstrated. For instance, bicuculline insensitivity at GABAA sites in insects has been found in CNS interneurons of the cockroach (Walker et al., 1971) and Manduca sexta (Waldrop et al., 1987).

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Opender Koul TABLE 2.2 Neuroreceptor antagonists on Western corn rootworm showing feeding deterrency. Chemical Strychnine HCl β-Hydrastine Bicuculline PK 11195 Gabazine Bulbocapnine HCl d-Tubocararine Cl Cyproheptadine HCl 7-Chlorokynurenic acid Harmine 2-Hydroxysaclofen Piperine Azadirachtin Parthenolide Agrophyllin A

ED50 nmol/dish 2.2 4.6 6.3 7.1 9.1 17.0 29.0 30.0 35.0 40.0 > 50.0 110.0 0.1 mM 1.5 mM 2.15 mM

Neuroreceptor Type Glycine (also GABAA) GABAA GABAA Periphral benzodiazepine GABAA Dopaminergic GABAA 5HT2 NMDA glutamergic GABAA GABAA Voltage sensitive Na gate GABAA ? GABAA ? GABAA ?

Source: Mullin et al. (1994).

In M. sexta GABA was found to mediate olfactory behavior via inhibitory interneurons in the antennal lobe of the deutocerebrum. However, only β-like subunits of GABA receptors from the CNS of Drosophila spp. (Henderson et al. 1993) and yellow fever mosquito, Aedes aegypti (Thompson et al., 1993), have been cloned from insect species. An interesting study of Mullin et al. (1991a, 1991b) shows the association of an antifeedant with a GABA/glycine receptor. Epoxy sesquiterpene lactone antifeedants from sunflower exhibit picrotoxinin-like GABA-gated chloride channel neurotoxicities in adult Western corn rootworm. In fact, terpenoid epoxides and isoquinoline and related alkaloids, such as azadirachtin, a strong antifeedant from neem (Koul, 1996), bicuculline, and so on, are interesting antifeedants of this category (Table 2.2). Mullin and coworkers (1994) have used three-dimensional structure-function relationships in Diabrotica to demonstrate antifeedant potency of compounds proposed to interact at a common binding site. Compounds were co-fitted through use of Alchemy III molecular modeling software (Tripos Associates). Common binding features for high antifeedant activity among the polycyclic terpenoid epoxides like azadirachtin, agrophylin, picrotoxinin, and caryophyllene oxide include an epoxide and π bonding sites separated by 0.5 to 0.6 nm, one or more electronegative oxygen centers, and a trisubstituted oxirane. Polyoxygenation may maintain sufficient polarity to allow diffusion to and interaction with the taste receptor. The 3D structural similarity between argophyllin (Mullin et al., 1991b) and picrotoxinin and dieldrin (Matsumura et al., 1987) suggest action through a shared picrotoxinin receptor site. The above studies also indicate that optimal polarity for molecular interactions at an exterior chemosensory receptor is different from internal interaction requirements with excitable cells, since membrane penetration and transport by binding proteins are not necessary (Mullin et al., 1994). A hydrophobic nature of compounds makes them non-inhibitory to feeding, as has been determined by using partition coefficient techniques. Many deterrents tested against Diabrotica have been shown to cause firing of a single taste neuron, and this chemosensory response correlates well with their feeding deterrency. In fact, GABA antagonism at the taste cell level may after neural processing result in net inhibition or excitation,

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respectively, of the dominant adductor, with a converse effect on the adductor. Clearly higher CNS inputs into mandibular opening and closing are also required. The actual inhibitory and excitatory inputs at each synaptic level, their means of integration, and the responsible neurotransmitters, receptors, and ion movements for insect gustation mostly remain to be clarified (Frazier, 1992).

BIOGENIC AMINE INHIBITION MECHANISM Biogenic amines are widely distributed within the insect CNS and thought to act as neurohormones, neuromodulators, or neurotransmitters (Evans, 1980). To get information about the mechanism of insect feeding, the insect response at biogenic amine levels against the feeding deterrents has been investigated (Ikemoto et al., 1995). For example, chlordimeform and aristolochic acid are well-known insect antifeedants and have been used as a probe of antifeedant activity. Five typical biogenic amines (5-hydroxytryptamine, dopamine, epinephrine, norepinephrine, and octopamine) using HPLC with an electrochemical detector have been investigated in the CNS of last instar Spodoptera litura larvae. It has been demonstrated that chlordimeform causes an increase in N-acetyldopamine levels in cerebral and suboesophageal ganglia and a decrease in 5-hydroxytryptamine (5HT) and n-acetyloctopamine levels in the cerebral, suboesophageal, and thoracic ganglia. On the other hand, aristolochic acid I, an antifeedant from Aristolochia species, did not cause any significant change in any amine levels except for dopamine and 5-hydroxytryptamine in suboesophageal ganglia and tyranine in thoracic ganglia (Ikemoto et al., 1995). Decrease in 5HT has also been reported in the cockroach cerebral ganglia (Omar et al., 1982). Inhibitory activity of chlordimeform against N-acetyltransferase has been shown in several insect species (Wierenga and Hollingworth, 1990). Although these studies suggest that some antifeedants have a mechanism of action through bioamine system in insects, comparing the effect on biogenic amine levels, no similar alterations have been observed. The relationship between such alterations and the antifeedant treatment is not clear as yet, but this could be one of the directions to study the mechanism of antifeedants and to understand the biochemical and physiological meaning of such alterations occurring due to feeding deterrents.

MECHANISMS RELATED TO SPECIFIC ALLELOCHEMICALS Chapter 7 illustrates more than 800 compounds that inhibit feeding of a variety of insect species using various bioefficacy procedures. However, the question remains: How do these chemicals affect the insect chemosensory cells, though a generalistic concept has been discussed above, and do they indicate the multiplicity of actions that can reduce feeding? Substantial data has been obtained in this regard for a diverse group of allelochemicals, the alkaloids. They inhibit impulse generation in sugar-sensitive cells in lepidopterans (Frazier, 1986; Simmonds et al., 1990) and competitively block sucrose responses in flesh flies (Morita et al., 1977). They also reduce the firing of the sugar-sensitive cells. Alkaloids as inhibitors of pyranose and furanose receptor sites have been established for flies (Wieczorek et al., 1988). The steroidal glycoalkaloids elicit irregular firing from several cells in the galeal and tarsal sensilla of adult and the larval α-sensilla of the Colorado potato beetle (Mitchell and Harrison, 1985). On the contrary, deterrent effects of various alkaloids, when tested against black blow flies, Phormia regina, in order to determine tarsal threshold for mixtures of sucrose and alkaloids, using kinetic analysis of electrophysiological data, ruled out competitive, no competitive, and

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un-competitive inhibition at receptor sites. Even no correlation of thresholds with available data on lipid solubility or octanol/water partition coefficients was observed. This suggests that there is no uniform limiting mechanism for this multiform array of compounds (Dethier and Bowdan, 1989). Terpenes of various classes also inhibit insect feeding. Azadirachtin, one of the most potent deterrents known, has been shown to induce the firing of one cell in the labial palps and one in the A3 sensillum of the clypeo-labrum of Schistocerca gregaria (Haskell and Schoonhoven, 1969). It also induces the firing of cells in the medial sensilla styloconica of Pieris brassicae and Lymantria dispar larvae (Schoonhoven and Jermy, 1977; Schoonhoven, 1982). Azadirachtin effects in other caterpillar species are characterized by the firing of large spikes in the lateral and medial sensilla styloconica. This cell appears to fire independently of the sugar-sensitive cell (Simmonds and Blaney, 1984). This confirms a general observation that the effects of azadirachtin (and many other compounds as well) are different in different species; that is, affecting more than one chemosensory cell type in more than one way. Luo et al. (1995) describe a significant correlation between behavior and response of the medial deterrent cell for three triterpenoids, azadirachtin, salannin, and toosendanin. They showed a relationship between sensory input and feeding inhibition, supporting the hypothesis that the response of the medial deterrent cell directly causes inhibition of feeding in Pieris brassicae (Messchendorp et al., 1996). However, interference with the lateral glucosinolate- and sugar-sensitive receptor cells measured for toosendanin (Schoonhoven and Luo, 1994) did not contribute to a closer relationship between sensory response and inhibition of feeding on cabbage leaf disks in P. brassicae, mentioned above. Toosendanin has been shown to modulate the sensory code underlying feeding behavior via several different peripheral sensory mechanisms; that is, stimulation of the deterrent receptor cell located in the medial maxillary sensillum styloconicum and inhibition of responses of both the sugar and glycosinolate receptor cells (Schoonhoven and Luo, 1994). Other limonoids have also been shown to deter feeding in a variety of insect species (Champagne et al., 1992), but there is no electrophysiological data available to compare the effects on taste receptor cells. This information gap is mainly due to the fact that limonoids are insoluble in water, and this makes it difficult to apply the tip recording technique in an electrophysiological bioassay of limonoids. Some workers have solved the problem by using mixtures of 50% tetrahydrofuran and 50% aqueous sodium chloride as a solvent system (Waladde et al., 1989). In these studies the compounds, like deoxylimonin, obacunone, and pedonin, were used to investigate responses of Eldana saccharina maxillary styloconic sensilla and exhibited an inhibition of the sugar receptor cells. The sesquiterpene warburganal produces irregular firing of more than one cell and then blocks the responsiveness of the sucrose- and inositol-sensitive styloconic cell of Spodoptera exempta (Ma, 1977). It was suggested that in this case the deterrent acts via interaction with protein sulfhydral groups located at the receptor membrane. Some studies also suggest that warburganal reversibly blocks chemoreceptors, but the observation that feeding behavior of larvae of Spodoptera eridania, Schistocerca gregaria, and Manduca sexta is little affected may indicate that sensory input to the brain in these species does not inhibit food intake (Schoonhoven and Yan, 1989). It is well evident that such dialdehydic sesquiterpenoids (including polygodial, muzigadiol, etc.) affect not only the phagostimulant receptors, but also the deterrent cells located in the medial hair of insects (Schoonhoven and Yan, 1989). This suggests a mechanism of interference common to all taste receptors. Therefore, it remains unexplained why different receptors show different degrees of inhibition and different recovery periods. However, what is certain is that these sesquiterpenoids induce antifeedant effects

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in various insect species by (i) stimulation of a deterrent receptor and (ii) decreased sensitivity of most or all other receptors. Clerodin, an antifeedant diterpene, induces greater feeding deterrency when applied to the maxillary palps as compared to the sensilla styloconica (Antonious et al., 1984), which is in contrast to what has been observed in formamidine compounds (discussed above). Ginkgolides from Ginkgo biloba, when tested electrophysiologically for neural responses in the maxillary taste sensilla, show a strong stimulation of the deterrent receptors of two types in Pieris brassicae and P. rapae. However, in P. brassicae the medial sensillum is more strongly stimulated than the lateral sensillum, whereas in P. rapae the reverse is true (Yan et al., 1990). This illustrates the marked difference between the chemoreceptory systems of the two species. Drimanes with a lactone group on the B-ring appear to be the most potent antifeedants at 5 mM level (Messchendorp et al., 1996). The positive correlation between feeding inhibition and response of the deterrent cell suggests that these compounds exert a direct inhibitory effect on the feeding centers in the CNS. At the same time few compounds, though highly deterrent, do not evoke strong responses from the deterrent cells. This suggests that other mechanisms, either sensory or post-ingestive, are also involved in feeding inhibition. One of the drimanes tested in the above studies depressed the neurons sensitive to feeding stimulants. Whether or not this interference contributes to feeding inhibition remains to be elucidated. What could be concluded from this study is that highly effective drimane antifeedants can be selected electrophysiologically on the basis of response intensity of the medial deterrent cells, but further details of the mechanisms underlying feeding inhibition await to be revealed. There is also the evidence that mechanisms for antifeedants may vary within a species. In another study, for instance, 11 analogous synthetic drimane antifeedant compounds were evaluated for their feeding-inhibiting effects on larvae of the large white butterfly Pieris brassicae in no-choice tests on the host plant Brassica oleracea. The results show that the five analogous antifeedants differentially influence feeding behavior and locomotion activity. Some are most likely sensory-mediated antifeedants. Habituation to these compounds occurs soon after the onset of the tests (i.e., within 0.5 to 1.5 h). Others, like confertifolin, probably are not direct sensory-mediated antifeedants and rather induce post-ingestive anorexia. In conclusion, the behavioral observations performed in this research indicate that analogous drimanes inhibit feeding by P. brassicae larvae through multiple mechanisms of action (Messchendorp et al., 2000). The antifeedant activity of chalcones, flavones, and flavanones is due to the predominant stimulation of the deterrent neurons in the medial sensillum stylonicum, and more than one receptor may be involved (Simmonds et al., 1990). These studies suggest that there are at least two different receptor types involved, each having a different structure-function type of response. From the preceding discussion it is clear that the molecular structure of compounds visa-vis the neural responses associated with feeding deterrence mechanisms should throw some light on various molecular parameters such as chirality, functional groups, molecular size, and lipophilicity of the compounds. However, it appears difficult, if not impossible, to ascertain any common molecular conformation to all active molecules and their induction of a specific type of neural/receptor response towards a specific deterrent.

REFERENCES Anthony, N.M., Harrison, J.B., and Sattelle, D.B. (1993) GABA receptor molecules of insects. In Y. Pichon (ed.), Comparative Molecular Neurobiology, Birkhauser Verlag, Basel, pp. 172–209.

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Antonious, A.G., Saito, T., and Nakamura, K. (1984) Electrophysiological response of the tobacco cutworm Spodoptera litura (F) to antifeedant compounds. J. Pestic. Sci., 9, 143–146. Asaoka, K. (1994) Different spectrum in responses of deterrent receptor cells in Sawa-J, a strain of the silkworm, Bombyx mori, with abnormal feeding habit. Zool. Sci (suppl.), 102. Bernays, E.A. and Chapman, R.F. (1994) Host Plant Selection by Phytophagous Insects. Chapman and Hall, New York. Bernays, E.A., Oppenheim, S., Chapman, R.F., Kwon, H., and Gould, F. (2000) Taste sensitivity of insect herbivores to deterrents is greater in specialists than in generalists: A behavioural test of the hypothesis with two closely related caterpillars. J. Chem. Ecol., 26, 547–563. Blaney, W.M. (1980) Chemoreception and food selection of locusts. Olfaction and Taste, 7, 127–130. Blom, F. (1978) Sensory activity and food intake: a study of input-output relationships in two phytophagous insects. Netherl. J. Zool., 28, 277–340. Boer de, G., Dethier, V.G., and Schoonhoven, L.M. (1977) Chemoreceptors in the preoral cavity of the tobacco hornworm, Manduca sexta, and their possible function in feeding behaviour. Entomol. Exp. Appl., 21, 287–298. Brattsten, L.M. and Ahmad, S. (1986) Molecular Aspects of Insect Plant Associations. New York: Plenum Press. Champagne, D.E., Koul, O., Isman, M.B., Towers, G.H.N., and Scudder, G.G.E. (1992) Biological activity of limonoids from the rutales. Phytochemistry, 31, 377–394. Chapman, R.F. (1982) Chemoreception: the significance of receptor numbers. Adv. Insect Physiol., 16, 247–285. Darlison, M.G. (1992) Invertebrate GABA and glutamate receptors: molecular biology reveals predictable structures but some unusual pharmacologies. TINS, 15, 469–473. Descoins, C. Jr. (2001) Sensing of antifeeding agents by phytophagous caterpillars (Lepidoptera). Annee-Biologique, 40, 55–73. Dethier, V.G. (1976) The Hungry Fly. Cambridge: Harvard University Press. Dethier, V.G. (1980) Evolution of receptor sensitivity to secondary plant substances with special reference to deterrents. Amer. Nat., 115, 45–66. Dethier, V.G. and Crnjar, R.M. (1982) Candidate codes in the gustatory system of caterpillars. J. Gen. Physiol., 79, 549–569. Dethier, V.G. and Bowdan, E. (1989) The effect of alkaloids on sugar receptors and the feeding behaviour of the blowfly. Physiol. Entomol., 14, 127–136. Devitt, B.D. and Smith, J.J.B. (1982) Morphology and fine structure of mouth part sensilla in the darksided cutworm, Euxoa messoria (Harris) (Lepidoptera: Noctuidae). Int. J. Insect Morph. Embryol., 11, 225–270. Devitt, B.D. and Smith, J.J.B. (1985) Action of mouth parts during feeding in the darkside cutworm, Euxoa messoria (Lepidoptera: Noctuidae). Can. Entomol., 117, 343–349. Evans, P.D. (1980) Biogenic amines in the insect nervous system. Adv. Insect Physiol., 15, 317–330. Frazier, J.L. (1985) Nervous system: Sensory system. In M.S. Blum (ed.), Fundamentals of Insect Physiology, John Wiley & Sons., New York, pp. 287–356. Frazier, J.L. (1986) The perception of plant allelochemicals that inhibit feeding. In L.B. Brattsten and S. Ahmad (eds.), Molecular Aspects of Insect Plant Associations, Plenum Press, New York, pp. 1–42.

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Frazier, J.L. (1992) How animals perceive secondary plant compounds. In G.A. Rosenthal and M.R. Berenbaum (eds.), Herbivores: Their Interaction with Secondary Plant Metabolites, Evolutionary and Ecological Processes, 2nd ed., Vol. 2, Academic Press, San Diego, pp. 89–134. Glendinning, J.I., Valcic, S., and Timmermann, B.N. (1998) Maxillary palps can mediate taste rejection of plant allelochemicals by caterpillars. J. Comp. Physiol. (A), 183, 35–43. Haskell, P.T. and Schoonhoven, L.M. (1969) The function of certain mouth part receptors in relation to feeding in Schistocerca gregaria and Locusta migratoria migratorioides. Entomol. Exp. Appl., 12, 423–440. Henderson, J.E., Soderlund, D.M., and Knipple, D.C. (1993) Characterization of putative γamino butyric acid (GABA) receptor β-subunit gene from Drosophila melanogaster. Biochem. Biophys. Res. Commun., 193, 474–482. Hollister, B., Dickens, J.C., Perez, F., and Deahl, K.L. (2001) Differential neurosensory responses of adult Colorado potato beetle, Leptinotarsa decemlineata, to glycoalkaloids. J. Chem. Ecol., 27, 1105–1118. Ikemoto, Y., Matsuzawa, Y., and Mizutani, J. (1995) The effect of antifeedants against the level of biogenic amines in the central nervous system of the lepidopteran insect (Spodoptera litura). Pestic. Biochem. Physiol., 52, 60–70. Ishikawa, S. (1966) Electrical response and functions of a bitter substance receptor associated with the maxillary sensilla of the larvae of the silkworm Bombyx mori. J. Cell Physiol., 67, 1–12. Kennedy, L.M. and Halpern, B. (1980) Fly chemoreceptors: A novel system for the taste modifier ziziphin. Physiol. Behavior, 24, 1–9. Koul, O. (1996) Mode of azadirachtin action. In N.S. Randhawa and B.S. Parmar (eds.), Neem, New Age International Publishers Ltd., New Delhi, pp. 160–170. Koul, O. (1997) Molecular targets for feeding deterrents in phytophagous insects. In A. Raman (ed.), Ecology and Evolution of Plant Feeding Insects in Nature and Man-Made Environments, International Scientific Publications, New Delhi and Backhuys Publishers, Leiden, The Netherlands, pp. 123–134. Kuppers, J. and Thurm, U. (1982) On the functional significance of ion circulation induced by electrogenic tissue. In A.D.F. Addink and N. Spronk (eds.), Exogenous and Endogenous Influences on Metabolic and Neural Control, Pergamon Press, Oxford, pp. 313–327. Luo, L.-E., van Loon, J.J.A., and Schoonhoven, L.M. (1995) Behavioural and sensory responses to some neem compounds by Pieris brassicae larvae. Physiol. Entomol., 20, 134–140. Ma, W.C. (1972) Dynamics of feeding responses in Pieris brassicae L. as a function of chemosensory input: a behavioural, ultrastructural and electrophysiological study. Meded. Landbouwhogeschool Wageningen 72/11, 162 pp. Ma, W.C. (1977) Alteration of chemoreceptor function in armyworm larvae (Spodoptera exempta) by a plant-derived sesquiterpenoid and sulfhydral reagent. Physiol. Entomol., 2, 199–207. Matsumura, F., Tanaka, K., and Ozoe, Y. (1987) GABA-related systems as targets for insecticides. In R.M. Hollingworth and M.B. Green (eds.), Sites of Action for Neurotoxic Pesticides, Symp. Ser. 356, American Chemical Society, Washington, D.C., pp. 44–70. Messchendorp, L., van Loon, J.J.A., and Gols, G.J.Z. (1996) Behavioural and sensory responses to drimane antifeedants in Pieris brassicae larvae. Entomol. Exp. Appl., 79, 195–202.

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Messchendorp, L., Smid, H.M., and van Loon, J.J.A. (1998) The role of an epipharyngeal sensillum in the perception of feeding deterrents by Leptinotarsa decemlineata larvae. J. Comp. Physiol. (A), 183, 255–264. Messchendorp, L., Gols, G.J.Z., and van Loon, J.J.A. (2000) Behavioural observations of Pieris brassicae larvae indicate multiple mechanisms of action of analogous drimane antifeedants. Entomol. Exp. Appl., 95, 217–227. Miller, J.R. and Strickler, K.L. (1984) Finding and accepting host plants. In W.J. Bell and R. Carde (eds.), Chemical Ecology of Insects, Sinauer Associates, Sunderland, MA, pp. 127–157. Mitchell, B.K. (1987) Interaction of alkaloids with galeal chemosensory cells of Colorado potato beetle. J. Chem Ecol., 13, 2009–2022. Mitchell, B.K. and Harrison, G.D. (1985) Effects of Solanum glycoalkaloids on chemosensilla in the Colorado potato beetle; a mechanism of feeding deterrence. J. Chem. Ecol., 11, 73–83. Mitchell, B.K., Rolseth, B.M., and McCashin, B.G. (1990) Differential responses of galeal sensilla of the adult Colorado potato beetle, Leptinotarsa decemlineata (Say) to leaf saps from host and non-host plants. Physiol. Entomol., 15, 61–72. Morita, H., Enomoto, K., Nakashima, M.N., Shimada, I., and Kijima, H. (1977) The receptor site for sugars in chemoreception of the flesh fly and the blow fly. In J. LeMagnen and P. MacLeod (eds.), Proceedings of Sixth International Symp., Olfaction and Taste, Information Retrieval, London, pp. 39–46. Mullin, C.A., Alfatafta, A.A., Harman, J.L., Serino, A.A., and Everett, S.L. (1991a) Corn rootworm feeding on sunflower and other composite: influence of floral terpenoid and phenolic factors. In P.A. Hedin (ed.), Naturally Occurring Pest Bioregulators, Symp. Ser. 449, American Chemical Society, Washington, D.C., pp. 278–292. Mullin, C.A., Alfatafta, A.A., Harman, J.L., Everett, S.L., and Serino, A.A. (1991b) Feeding and toxic effects of floral sesquiterpene lactones, diterpenes and phenolics from sunflower (Helianthus annuus L.) on western corn rootworm. J. Agric. Food Chem., 39, 2293–2299. Mullin, C.A., Chyb, S., Eichenseer, H., Hollister, B., and Frazier, J.L. (1994) Neuroreceptor mechanisms in insect gustation: A pharmacological approach. J. Insect Physiol., 40, 913–931. Omar, D., Murdock, L.L., and Hollingworth, R.M. (1982) Actions of pharmacological agents on 5-hydroxytryptamine and dopamine in the cockroach nervous system (Periplaneta americana L.). Comp. Biochem. Physiol., 73, 423–429. Renwick, J.A.A. (2001) Variable diets and changing taste in plant–insect relationships. J. Chem. Ecol., 27, 1063–1076. Sattelle, D.B. (1990) GABA receptors of insects. Adv. Insect Physiol., 22, 1–113. Sattelle, D.B. (1992) Receptors for L-glutamate and GABA in the nervous system of an insect (Periplaneta americana). Comp. Biochem. Physiol., 103C, 429–438. Schoonhoven, L.M. (1982) Biological aspects of antifeedants. Entomol. Exp. Appl., 31, 57–69. Schoonhoven, L.M. (1987) What makes a caterpillar eat? The sensory code underlying feeding behaviour. In R.F. Chapman, E.A. Bernays, and J.G. Stoffolano (eds.), Perspectives in Chemoreception and Behaviour, Springer-Verlag, New York, pp. 69–97. Schoonhoven, L.M. (1988) Stereoselective perception of antifeedants in insects. In E.J. Ariens, J.J.S. van Rensen, and W. Welling (eds.), Stereoselectivity of Pesticides; Biological and Chemical Problems, Elsevier, Amsterdam, pp. 289–302. Schoonhoven, L.M. (1991) The sense of distaste in plant feeding insects: A reflection on its evolution. Phytoparasitica, 19, 3–7.

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Schoonhoven, L.M. and Dethier, V.G. (1966) Sensory aspects of host-plant discrimination by lepidopterous larvae. Arch. Neerl. Zool., 16, 497–530. Schoonhoven, L.M. and Jermy, T. (1977) A behavioural and electrophysiological analysis of insect feeding deterrents. In N.R. Mcfarlane (ed.), Crop Protection Agents, Academic Press, New York, pp. 133–146. Schoonhoven, L.M. and Blom, F. (1988) Chemoreception and feeding behaviour in a caterpillar: towards a model of brain functioning in insects. Entomol Exp. Appl., 49, 123–129. Schoonhoven, L.M. and Yan Fu-Shun (1989) Interference with normal chemoreceptor activity by some sesquiterpenoid antifeedants in an herbivorous insect, Pieris brassicae. J. Insect Physiol., 35, 725–728. Schoonhoven, L.M. and Luo, L.-E. (1994) Multiple mode of action of the feeding deterrent toosendanin, on the sense of taste in Pieris brassicae larvae. J. Comp. Physiol., 175A, 519–524. Schoonhoven, L.M., Blaney, W.M., and Simmonds, M.S.J. (1992) Sensory coding of feeding deterrents in phytophagous insects. In E. Bernays (ed.), Insect–Plant Interactions, Vol. 4, CRC Press, Boca Raton, FL, pp. 59–79. Schoonhoven, L.M., Jermy, T., and van Loon, J.J.A. (1998) Insect–Plant Biology. Chapman and Hall, London. Simmonds, M.S.J. and Blaney, W.M. (1984) Some neurophysiological effects of azadirachtin on lepidopteran larvae and their feeding response. Proc. 2nd Int. Neem Conf., GTZ, Rauischazhausen, pp. 163–179. Simmonds, M.S.J., and Blaney, W.M. (1990) Gustatory codes in lepidopterous larvae. Symp. Biol. Hung., 39, 17–27. Simmonds, M.S.J., Blaney, W.M., and Fellows, L.E. (1990) Behaviour and electrophysiological study of antifeedant mechanisms associated with polyhydroxy alkaloids. J. Chem. Ecol., 16, 3167–3196. Stadler, E. (1992) Behavioural responses of insects to plant secondary compounds. In G.A. Rosenthal and M. R. Berenbaum (eds.), Herbivores: Their Interaction with Secondary Plant Metabolites; Evolutionary and Ecological Processes, Academic Press, San Diego, pp. 44–88. Sturckow, B. (1959) Ueber den Geschmackssinn und den Tastsinn von Leptinotarsa decemlineata Say (Chrysomelidae). Z. Vergl. Physiol., 42, 255–302. Tang, D.L., Wang, C.Z., Luo, L., and Qin, J.D. (2000) Comparative study on the responses of maxillary sensilla styloconica of cotton bollworm Helicoverpa armigera and Oriental tobacco budworm H. assulta larvae to phytochemicals. Sci. China Ser.C, Life Sci., 43, 606–612. Thompson, M., Shotkoski, F., and ffrench-Constant, R. (1993) Cloning and sequencing of the cyclodiene insecticide resistant gene from the yellow fever mosquito, Aedes aegypti. FEBS Letters, 325, 187–190. Waldrop, B., Christensen, T.A., and Hildebrand, J.G. (1987) GABA mediated synaptic inhibition of projection neurons in the antennal lobes of the sphinx moth, Manduca sexta. J. Comp. Physiol., 161A, 23–32. Walker, R.J., Crossman, A.R., Woodruff, G.N., and Kerkut, G.A. (1971) The effect of bicuculline on the γ-amino butyric acid (GABA) receptors of neurons of Periplaneta americana and Helix aspersa. Brain Res., 33, 75–82. Waladde, S.M., Hassanali, A., and Ochieng, S.A. (1989) Taste sensilla responses to limonoids, natural insect antifeedants. Insect Sci. Applic., 10, 301–308.

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Wieczorek, H. (1976) The glycoside receptor of the larvae of Mamestra brassicae L. (Lepidoptera: Noctuidae). J. Comp. Physiol., 106A, 153–176. Wieczorek, H., Shimada, I., and Hopperdietzel, C. (1988) Treatment with pronase, uncouples water and sugar reception in the labellar water receptor of blowfly. J. Comp. Physiol., 163A, 413–419. Wierenga, J.M. and Hollingworth, R.M. (1990) Octopamine uptake and metabolism in the insect nervous system. J. Neurochem., 54, 479–489. Yan Fu-shun, Evans, K.A., Stevens, L.H., van Beek, T.A., and Schoonhoven, L.M. (1990) Deterrents extracted from the leaves of Ginkgo biloba: effects on feeding and contact chemoreceptors. Entomol. Exp. Appl., 54, 57–64.

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3 BIOASSAYS Bioassays against insects have been used for decades as a means of elucidating the activity of many chemical components. The major goals achieved by employing bioassay techniques are to determine the roles of naturally occurring chemicals, identify the mechanism of resistance in crop plants, and to find various insect control agents. As the aim of this book is to understand chemicals that inhibit feeding, the emphasis will be on antifeedant allelochemical bioassays. However, before going into the details of various types of bioassays for feeding-deterrent activity, it is imperative to know about certain fundamental requirements for such evaluations. The basic design to study deterrents is to present to an insect a substrate with the candidate chemical and to measure the response of the insect. Therefore, substrate choice and presentation are important factors for a successful bioassay. Both natural and artificial substrates are used, depending upon the goal of the experiment. On one hand one may emphasize that artificial substrates offer uniformity, but at the same time studies have shown that thresholds for the same deterrent may vary as much as 1000 times between natural and artificial substrates (Schoonhoven, 1982), perhaps due to differences in porosity or uptake rates by the insect. For sucking insects, the principal artificial substrate used has been a chemically defined liquid presented between natural or artificial membranes (Mittler and Dadd, 1962). However, whatever the substrate may be, it is important that no textural differences should occur between the control and test substrates. Color differences may also influence insects tested (Meisner and Ascher, 1973). Care is needed to ensure the least hindrance with the insect’s chemoreceptor’s encounter, which should be in the usual way (i.e., for edge feeders substrates are placed above the floor level). Natural substrates could be whole plant, leaves, leaf disks (more frequently used), or specialized substrates like twigs, blocks of wood, board, and paper towel disks. Artificial substrates usually include agar-based artificial diets, simple

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liquid-based artificial diets, styropors (which are good model substrates for many insects using lamellae), or disks of foamed polystyrene, styrofoam, or polyurethane, and glass fiber disks. After the choice of the substrate, an important step is the chemical application. For antifeedant testing, concentrations need to be selected to achieve the goal of finding the effective concentrations for crop protection. Higgins and Pedigo (1979a) used a foliar phytotoxicity threshold base as the presence of leaf necrosis to determine maximum acceptable concentration. One could use the sensitivity of the insect chemosensilla as a criterion for concentration, but it is difficult as very little is known about these sensitivities. The role of solvents is another important factor. Ascher et al. (1981) found that grades of a common solvent, methanol, could differ in their effects. My studies with antifeedant evaluations have revealed that alcohols interfere with the texture of natural substrates (particularly leaf materials), and therefore should be avoided. The best way is to depend on waterbased emulsified solutions, which hold a small quantity of the solvent. Therefore, natural control substrates with and without solvent should be tested to verify that there is no alteration in palatability due to solvents. In electrophysiological studies appropriate electrolyte use is essential. The next important factors for evaluation are the conditions of the test. Jermy et al. (1968) used a sytem of evaluation where tests were terminated when 50% of either substrate in a choice trial was consumed, so the insects did not lose discrimination due to hunger. This system is adopted even today in many studies. There is also evidence that previous experiences affect insect diet choice by induction, habituation, food aversion learning, and associative learning. Therefore, such problems need to be avoided and apparently could be achieved by using insects only once in a test and for a short duration. Pilot observations are necessary to establish time of maximum feeding, which varies among various insect species. Temperature, humidity, light levels, and population of test insects are other parameters that need to be determined from field observations for better results in the antifeedant assay. In fact, performing short- and long-term tests provides the most information, as data on changes in behavior through lengthy exposure to a chemical may be useful (Lewis and Bernays, 1985). The above-mentioned step is then followed by measurements and observations. These parameters will depend upon the feeding behavior of the insect; that is, methodologies will depend upon whether the bioassay is conducted against a chewing insect, a sucking insect, and so on. Depending on the different modes of feeding in insects, various types of bioassay procedures have been developed in laboratories to evaluate insect antifeedants. I have categorized these bioassays as shown in Figure 3.1. However, some specific assays used against specific insect species are also described.

LEAF DISK ASSAY Leaf disks are commonly used in insect bioassays of preference or consumption with chewing insects. This assay can be conducted in two basic ways: i) choice assay and ii) no-choice assay. Insects can choose either control or treated disks (choice) or insects may be exposed to the test substance only (no-choice). The no-choice situation often is more representative of our agricultural system, especially for monophagous species, but at the same time it is very sensitive. The general procedure adopted in this test is that measured leaf disks are punched out from substrates and treated either on one side or both sides with a known quantity of test material in a carrier solvent. It is preferable to use emulsified solutions in water in order to avoid interference with leaf disk texture due to solvents (Koul et al., 1990). A method has been described by which leaf surfaces can be covered with a uniform amount of a test chemical

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LEAF DISC TEST LOCUSTS, GRASSHOPPERS MOSTLY LEPIDOPTERANS

ARTIFICIAL DIET TEST

ARGENTINE STEM WEEVIL GREEN BUGS, LEPIDOPTERANS

PAPER TOWEL DISC TEST

TERMITES

WHEAT WAFER ASSAY

STORED GRAIN PESTS

STYROPOR ASSAY

LEPIDOPTERANS SUCKING INSECTS

ANTIFEEDANT BIOASSAYS GLASS FIBER DISC ASSAY

PIPET ASSAY

SIMULATION ASSAY

IMPREGNATION ASSAY

ELECTRO PHYSIOLOGICAL ASSAY

LEPIDOPTERANS, LOCUSTS ACRIDIDS

DIPTERANS

MANY PHYTOPHAGOUS INSECTS

BEAN BEETLES, SCALE INSECTS, WHITE FLIES, CITRUS MITES, WIREWORMS, LEPIDOPTERANS LEPIDOPTERANS LEAFHOPPERS COCKROACHES

FIGURE 3.1 Bioassay methods.

for bioassay with leaf-feeding insects. Chemicals are dissolved in gelatin solutions, which can be sprayed evenly and which will adhere well to many leaf surfaces. However, calibrations of rates of application are required (Wolfson and Murdock, 1987). After application, the leaf disks are dried at room temperature and then fed to candidate insects. Usually the arenas used are petri dishes of variable sizes (9-cm-diameter size is most common for lepidopteran larvae) in which one treated and one control disk is placed (choice), or both the leaf disks are treated (no-choice). In certain experiments five to ten treated and

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untreated leaf disks are used and placed alternately in the petri dishes in a choice situation. The number of larvae introduced into each arena is variable depending upon the size and stadium of the larvae used. There is also considerable variation in the duration of experiments (see Chapter 7), both long term and short term. The consumption in each experiment is measured using various digitizing leaf area meters. In certain studies the choice tests have been referred to as dual choice tests. In these experiments individual larvae are confined for a short term (5 to 6 hours) in a petri dish containing two leaf disks. The treatment disks are painted with an aliquot of test solution and the control disks with solvent solution only. The bioassay is conducted for very short duration or until 50% of either disk is consumed. The amount eaten is then assessed and calculated. In certain cases even more than two leaf disks have been used. For instance, while testing drimane-type antifeedants in dual-choice tests against Pieris brassicae, six cabbage leaf disks (3.8 cm2 area) placed in a circle were assayed in a glass petri dish. The upper surface of alternate disks was painted with 10 µl drimane or control solution, after which they were left to dry for 30 minutes. After 3 hours of ad libitum feeding, the remaining disk areas were measured with a leaf area meter (Messchendorp et al., 1996). However, some findings have implications to the design of disk bioassays. Clearly, the ratio of cut edge to overall leaf disk surface area is an important variable that should be taken into account (Jones and Coleman, 1988). The decision to choose one disk size over another has often been a matter of convenience for the experimenter. Thus, it has been suggested that selection of the appropriate disk size will depend upon several variables (Jones and Coleman, 1988): • • •

Whether the insect feeds in the center or edges of the leaves The size of the insect, particularly the ratio of insect size to disk size The type of bioassay being carried out

For example, if a leaf disk from the host plant of a center-feeding insect were painted with a deterrent chemical, one would predict the deterrent effects would be greater in a large disk assay than in a small disk assay. This is because the cut edge would contribute counteracting host-plant attractant or stimulant signals to a greater extent on small disks. In order to measure and calculate the effective concentrations of insect antifeedants, there is no standard size terminology. In certain cases the consumed area of treated leaf disks is expressed as a percentage of the consumed area of control leaf disks. In others, antifeedance has been calculated on the basis of feeding ratios (i.e., test consumption/control consumption followed by grading) (Zalkow et al., 1979). This ratio has also been calculated as: Feeding control = 100 { 1 – % feeding/% feeding by stock} and graded as +++ (90–100%); ++ (60–90%); + (30–60%) protection, and – (0–30%) showing no protection (Lidert et al., 1985). In many cases an antifeedant is considered to be effective when feeding inhibition of 80–100% is achieved (Bernays and Chapman, 1978). EC90 and EC95 values have also been calculated. On the whole some generalized formulas have been devised to calculate feeding deterrence quantitatively: • •

D = (1 – T/C) × 100, where T and C are percent weights of treated and control leaf disks (dry weight basis) and D is the percent deterrence (Hosozawa et al., 1974). Protection (%) = (% PTS – % PIC)/100 – % PIC, where PTS is protection in treated samples and PIC is protection in control samples (Singh and Pant, 1980).

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Feeding inhibition (%) = % CTD × 100/% CTD + % CUD; where CTD is consumption of treated disks and CUD is consumption of untreated disks (Reed and Jacobson, 1983). Feeding deterrence (%) = (C – T)/(C + T) × 100, where C and T are the consumption of control and treated disks, respectively (Koul et al., 1990). This formula is preferred for the measurement of deterrence.

Recently, leaf disk choice bioassay has been very successfully used to study aphids (Lowery and Isman, 1993; Koul et al., 1997). In this procedure two leaf disks with the test material and two disks with carrier alone are allowed to dry and then arranged alternately in small petri dishes (9 × 50 mm) with their edges barely touching. Deterrence of the test material is determined by the proportion of aphids on the treated disks relative to the total number of aphids on treated and untreated disks in each dish. An improved antifeedant bioassay has been devised that allows an accurate measurement of consumed disk surfaces, using a video camera interfaced with a computer. The scanned image of the leaf disk is stored and the eaten areas are measured with the help of videoimage analysis software. This method allows for precise quantification of insect antifeedant activity tested on leaf material (Escoubas et al., 1993). The process of storing the image involves selection of the interesting area in the scanning window via cut-and-paste functions. By this method, the image can be edited, enhanced, and used in later measurements.

ARTIFICIAL DIET FEEDING Artificial diet tests are also commonly used against many lepidopterans, green bugs, and weevils. A general procedure for this evaluation is to incorporate the test material into artificial diets, feed to test insects, and calculate mean percent feeding depression. However, artificial diets usually have one of two problems: they are suboptimal or they can be superoptimal (Wolfson, 1988). Compared with the most susceptible host plants, artificial diets often foster more rapid growth (Reese and Field, 1986) and thus can make insects less susceptible to the allelochemicals being tested. According to Berenbaum (1986), tests of chemicals in artificial diets could be compromised by eliminating naturally occurring synergistic interactions between nutrients and allelochemicals. However, there are some specific examples where artificial diets have been successfully used for evaluation. For instance, artificial diet plugs of known weight were placed in an arena (35 × 10 mm petri dishes) along with two sixth instar larvae of spruce budworm, Choristoneura fumiferana. Both choice and no-choice situations were established. Larvae were allowed to feed for 48 hours, at which time remaining portions of diet plugs were weighed. Results were expressed as weight of plugs consumed/insect/48h. Each group was replicated three times for a total of 24 insects/treatment (Alford and Bentley, 1986). Mean percent feeding depression was calculated as = [ 1 – treatment consumption/control consumption × 100 ]. In the case of the boll weevil, bioassay chambers were constructed by pouring a layer (5 mm thick) of beeswax paraffin (2:1 by weight) into the bottom of a petri dish (1.5 × 10 cm). Three to six media wells were cut into the cooling paraffin with a No. 9 cork borer (13 mm diameter), 2 cm from the center of the dish and equidistant apart. The wells were filled with cooling 2.5% nonnutrient agar solution plus 3.0% pharmamedia or freeze-dried cotton square powder. A lens paper disk cut with a No. 10 cork borer (15 mm diameter) was placed on top of the solidified medium surface. Water (20 µl) was applied to the paper to provide

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moisture for the insects and to hold the papers to the medium surface. Chemicals were randomly applied to the lens papers as 20 µl aliquots in methanol and allowed to dry for 30 minutes. 10 male or female boll weevils were released into each assay chamber and the tops were applied to prevent escape. The scores for the number of punctures after 3 to 6 hours were noted using a dissecting microscope, and deterrence effects were calculated (Bird and Hedin, 1986). For Eurema hecabe mandarina (yellow butterfly), larvae pre-starved for 4 hours were placed on each of the following diets: 1. The basal diet (1% agar only). 2. The control diet prepared by incorporating dried leaf powder of Lespedeza cuneata (0.39 g) in 1.4 ml of 1% agar. 3. The test diets prepared by incorporating plant powders or fractions or compounds into dried leaf powder as in (2) in 1 ml of 1% agar at a total weight of 1.28 g. The number of frass pellets deposited during the test period (20 h) was then counted. The feeding inhibition activity was calculated on the basis of feeding ratio:

Feeding ratio =

Mean frass count/test diet – Mean frass count for the basal diet Mean frass count for the control diet – Mean fraass count for the basal diet

When the ratio was < 50% it was considered to be a positive inhibition. When the response was between 0 and 20% the test material was a very strong inhibitor (Numata et al., 1984). Agar-based diets have also been used for Argentine stem weevils, Listronotus bonariensis (Rowan and Gaynor, 1986). After cooling, these diets were cut into 35 to 40 disks with a cork borer (1 cm × 3 mm thick) in a choice bioassay. For treatment experiments, cellulose powder was mixed with the candidate chemical at 2 g of extract/4 g of cellulose powder. The suspensions were made, evaporated to dryness, and agar disks were made. There are artificial diets developed for evaluating antifeedant chemicals against aphids. A generalized pattern has been adopted for Schizaphis graminum. In this procedure small (35 ml) polystyrene catsup cups are used as test chambers. For each test 50 to 75 aphids of all ages are transferred from the colony by brushing them carefully off the plant with a hair paint brush. The polystyrene test chambers consist of tight-fitting plastic snap-on caps, which possess circular holes (1.5 cm) punched with a cork borer for the placement of the diet container. The container is usually made from a soft polyethylene vial cap, which fits snuggly into the hole prepared with the cork borer in the lid. A thin sheet of parafilm is stretched across the vial cap to create a sealed diet chamber. Diet containing the test material is added by injection with a syringe through the topside of each polyethylene cap. The diet-filled containers are placed by a snug fit into the hole bored in the lid of the test chamber with the parafilm membrane facing the interior of the test chamber towards the aphids. The tests are maintained for 24 hours at 24˚C. After 24 hours the number of aphids feeding and the number wandering are counted and compared with appropriate controls. One week later an identical set of experiments is run and all the replicates are averaged (Dreyer et al., 1981). In certain cases in synthetic diet feeding, each substance is tested at a series of concentrations so that a dose-dependent curve could be constructed. From this curve a concentration could be obtained at which half of the aphids (ED50 values) would not feed (Rose et al., 1981). Calculations can also be based on the difference in weight of the larvae in each group of treatments, multiplied by 100 and divided by the average weight of larvae in the control group to obtain a larval weight index (Warthen et al., 1982).

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STYROPOR ASSAY This method is usually used for lepidopterans and sucking types of insects (Koul, 1993). Thin 0.6 mm lamellae (6 × 4 cm) of styropor (foamed polystyrene) of density 0.016 (P16) are dipped into solutions of the test compounds of different concentrations containing 5% sucrose. The lamellae are left to dry for 24 hours and then weighed individually. They are then offered singly in large 15-cm-diameter petri dishes to one early sixth instar larvae (e.g., Spodoptera littoralis of 170 to 190 mg body weight), together with water absorbed in cotton wads. The number of replicates varies from five to ten for each level of treatment. The weight of styropor after consumption and the weight of fecal pellets voided are recorded for each larva after 48 hours and used as criteria for antifeedant activity (Ascher and Meisner, 1973).

GLASS FIBER DISK TEST This type of antifeedant bioassay, though used for lepidopteran larvae, has also been useful to evaluate compounds against locusts and other acridids. In this method the test compounds are added to glass fiber disks (Whatman GF/A), a pair of which are presented dry to each individual insect. The disk size varies from 2.1 to 4.25 cm, which are usually dried in a cool air stream. The loading of the disks varies from 100 to 400 µl of test material. Locusts are confined individually in clear plastic boxes (27 × 15 × 10 cm), each screened from its neighbor so that insects in adjacent boxes do not disturb each other. Disks are presented in pairs to facilitate feeding for 24 hours until 30 to 50% of the control disk has been consumed; the amount of disk eaten is measured by an area meter. Lepidopteran larvae are confined in petri dishes (9 cm diameter) with a pair of disks for up to 8 hours so that never more than 50% of any disk is eaten. After removal of the larvae disks are redried and the amount eaten is determined by weight (Blaney et al., 1984). For acridids, glass fiber disks of 4.5 cm diameter have been used by adding known quantities of sucrose solutions to give either 5% or 12% dry weight of sucrose. After drying, disks are treated with a known amount of compound in solution. Approximately 0.4 ml solution saturates this size of disk and gives an average concentration of 0.02 to 2.0% on a dry weight basis. After evaporation of solvent the disks are checked by weight and then fed to insects. All choice tests are carried with well-fed insects approximately halfway through the final larval instar. Experiments are run for 3 hours and usually as 10 to 15 replicates. After the test each remaining disk is measured with an area meter or in certain cases weighed and the amount of each disk eaten/insect is calculated (Bernays and DeLuca, 1981).

PAPER TOWEL DISK TEST Commonly used for termites, this method has been very well described by Scheffrahn and Rust (1983). The natural paper towels, cut into 9.6-cm-diameter disks (72 cm2 area and 360 mg average weight) are individually placed in glass petri dishes. Predetermined amounts of wood extract or pure compounds that would yield calculated specific mass per unit area of paper (mg/cm2) are weighed in glass shell vials (e.g., 36 mg of a compound applied to a disk provided a deposit of 0.5 mg/cm2). The test compound dissolved in 2 ml of an appropriate solvent is poured from the vial evenly onto the disk resting inside a petri dish cover. The cover is then placed on a warm hot plate to evaporate the solvent. Trial tests using an ethersoluble dye can be used for practice to get uniform deposits. Each treated disk is cut into four smaller disks (3.9 cm diameter) and held overnight at room temperature before testing. For deterrency bioassays 0.5 mg/cm2 application is presented for 3 days. A choice test is conducted in which four disks are constructed from two half disks; one is treated with test

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material and the other half a solvent blank to demonstrate feeding preference. The half disks are joined with a thin strip of cellophane tape on the surface not exposed to termites. Evaluation of weight loss of the disks due to feeding is averaged for each treatment and a comparison of their means determined statistically (Scheffrahn and Rust, 1983). There are many statistical procedures valid to use in antifeedant assays to establish the significance of the data obtained. In some cases feeding bioassays are based on a comparison of feeding on 1.2-cm-round paper penicillin assay disks. Penicillin disks are prepared by placing them on a clean enamelated tray, and then treated with 50 µl of test material in 95% ethanol (controls with carrier alone). Disks are allowed to dry and placed in 35 × 1.0 mm plastic petri dishes (1/dish). Each disk then receives 50 µl of 0.03M L-proline and 0.3M sucrose solutions. For example, sixth instars of spruce budworm (24- to 48-h-old) have been used in this type of bioassay and placed in petri dishes with test or control disks (three replicates or more). At 48 h after initiation of the test, the larvae were removed and frass pellets counted. The yellowish brown frass pellets derived from the artificial food in this insect species were easily differentiated from the white pellets derived from the paper disks. Frass pellets from artificial food were not included in counts (Bentley et al., 1984). The percentage of deterrence was calculated as:

1–

No. of pellets of frass from disks in teest × 100 No. of pellets of frass from disks in coontrol

WAFER ASSAY Wafer assays have been successfully used in assessing antifeedants against stored product insects (Nawrot et al., 1982; Harmatha and Nawrot, 1984). In this method wheat wafer disks (1 cm diameter) are immersed in test solution (in ethanol). After ethanol evaporation, stored grain insects (e.g., Tribolium, Trogoderma, Sitophilus, etc.) are provided with either two wafer disks immersed in ethanol (CC) or two disks saturated with test solution (TT), or they have a choice between ethanol or test material treated disks (CT). On the basis of amount of food consumed (on a weight difference basis) in the experiments where the insects have a possibility of choice, a relative index of deterrence is calculated (Paruch et al., 2000). The weight of food supersaturated with test material and consumed by the control group is used for the calculation of the absolute index. A compound for which both indices reach the value of 100 and the sum = 200 is called an ideal deterrent. The classification of indices is as follows: Below 0 0 – 50 51 – 100 101 – 150 151 – 200

= Attractant = Poor deterrent = Medium deterrent = Good deterrent = Very good deterrent

The coefficients are calculated as: Absolute coefficient of deterrency = [ (CC – TT)/(CC + TT) × 100 ] {A} Relative coefficient of deterrency = [ (C – T)/(C + T) × 100 ] {R} Total coefficient of deterrency = ∑ {A} + {R} A very specific wafer assay to evaluate feeding deterrents against plant weevils has been documented (Thomas and Bradley, 1975). In this assay compounds have been used on pith

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wafers of American elder, Sambucus camadensis L., in petri dishes; 2-mm-thick wafers were initially treated with some feeding stimulant, which would produce uniform feeding. The feeding deterrents were then added and the amount of feeding on the wafers treated with deterrent was compared with the feeding on control wafers (i.e., those treated with stimulants only). Wafers first treated with sucrose solution (15% dry weight) were dried for 1 hour at 65˚C. An ethanol extract of mature Loblolly pine phloem (20 mg/ml) was made and 0.1 ml pipetted evenly over the surface of each wafer and dried again at 65˚C for 1 hour. This was followed by the application of the feeding deterrent in appropriate solvent at the rate of 0.1 ml/wafer. The wafers were then dried to a constant weight for 1 hour at 70˚C under a vacuum. The wafers were then weighed to the nearest 0.1 mg and placed in petri dishes having a 1-cm-thick layer of moistened plaster of paris in the bottom. After feeding for 7 hours by the weevils, the wafers were removed, dried to constant weight for 1 hour at 70˚C under vacuum, and reweighed. The mean weight losses resulting from feeding were ranked by analysis of variance as the parameter of antifeedance.

ELECTROPHYSIOLOGICAL ASSAY Electrophysiological assays are modern techniques to evaluate the physiological deterrency of chemicals. The generalized approach is that two microelectrodes are inserted into the maxillary palp and the sensilla. The electrophysiological responses are then recorded with an oscilloscope as impulses/sec. by contacting the tips of sensilla with filter paper impregnated with the test material. The maximum number of impulses that can be evoked under treatment and control conditions are recorded. The functions of all the receptors, though not clear, it is now known that some respond to feeding deterrents (Ma, 1977; Nakanishi and Kubo, 1977), and is discussed separately in Chapter 2. For instance, a procedure adopted for Spodoptera litura larvae was that larvae were fixed ventral side upwards on a piece of plastic foam plate with three loops of steel around the neck, thorax, and the posterior abdomen segments. Recording was accomplished by means of stainless steel electrodes (5 µm diameter). The electrode was inserted into the proximal part of the hypopharynx by means of micromanipulator. This method permitted simultaneous recording of muscle potential and nerve impulses. Impulses were conducted proximally towards the CNS and also distally towards the hypopharynx tip. The effectiveness was based on the number of impulses. The test compounds were applied topically to various mouthparts and antennae by means of a fine glass capillary adapted to a microsyringe attached to a manual applicator. The recording was done on an oscilloscope to which a recording camera was attached (Antonious et al., 1984). Some specific techniques in electrophysiological evaluation have been used that could be generalized if tested against a variety of insect species. In the case of Ostrinia furnacalis, an attempt has been made to study the gustatory chemoreceptor in larval taste systems for bioassay-guided fractionation of antifeedants. This tip recording technique (Shang et al., 1993) has been used to detect the antifeedant activity by placing electrodes in contact with the tip of medial or lateral sensilla styloconica of the isolated maxillae. The nerve action potential yielding high frequencies of spikes are recorded and relative effects calculated. Jones (1979) established an automatic feeding detector (AFD) for use in evaluating insect angles to form a flat plate. This plate fits through a 1.4-cm-diameter hole drilled in the center of a small petri dish base. The dish is maintained on two small pneumatic pistons (disposable 2 ml syringes)—one fixed and the other free—that permit the dish height and the alignment of the trembler to be adjusted. A lid covers the petri dish base with a gauze guard (the guard prevents the larva from moving over the disk). At an approximate central position on the trembler is located a needle fixed to the central brass rod of a clamped linear differential

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transductor. The transductor output is connected to a chart recorder and a light source positioned over the petri dish. The whole apparatus is mounted on a leveled, vibration-free bench. Movement of the trembler results in a deflection on the chart recorder. This deflection is calibrated by adding known weights to the end plate and by moving the end plate a vertical distance. Changes in weight are measurable at an accuracy of ±10 mg from 20 to 500 mg and ±30 mg from 500 to 1000 mg. Vertical distance is measurable at an accuracy of ±0.2 mm over the range of 0.2 to 3.6 mm. A pre-weighed leaf disk is fixed to the end plate using a small amount of inert silicon grease, and the recorder offset adjusted to center the pen at mid-scale. A single insect larva is introduced into the petri dish and behavioral observations made over a 30- to 40-minute period. A number of such trials are carried out to establish a correlation between traces and feeding behavior. The behavior of larvae on disks treated with deterrent chemicals results in characteristic traces, which differ from those obtained with natural host-plant controls. Quantitative measurements of consumption, duration of feeding, number of test bites, and number of rejections of the disk are then made and compared. This detector system is cheap to construct, is robust in operation, and gives rapid analyses. This method can be used with any insect capable of causing a deflection of greater than 0.2 mm. Another interesting device has been used to study aphids. Synthetic diets treated with chemicals (like DIMBOA) are prepared just prior to the recording assay. The diet is injected into plastic vial caps (300 µl) over which is stretched a parafilm membrane. A platinum wire, inserted through the plastic cap into the diet, serves as the voltage input electrode. A gold wire fixed to the dorsum of the test aphid with silver conductive paint serves as a lead to the input of the amplifier. The analysis is based on the duration of I-waves (ingestion), S-waves (salivation), and non-probing over 2 h assay period (Argandona et al., 1983). A similar useful electronically recorded feeding behavior for rice hoppers, Nephotettix virescens, is known to evaluate the efficacy of allelochemicals (Saxena and Khan, 1985). In this experimental bioassay a 5 cm fine (18 µm) gold wire is attached by a small quantity of silver paint to the dorsum of an 8- to 10-h-old female reared on a virus-free 45-d-old TN1rice plant. Before attaching the wire, insects are anesthetized with carbon dioxide gas. The insects are starved but water satiated for 2 hours and then placed on an intact leaf blade of a treated or control plant. The gold wire is connected directly to the negative input terminal of a transistorized automatic null balancing DC chart recorder having 250 nm recording width and input resistance of 1MΩ. The voltage source consists of two 1.5v DC batteries connected in series. The positive battery terminal is connected with plant roots through moistened filter paper and an aluminium foil. The negative battery terminal is connected directly to the positive input terminal of the chart recorder. The recorder pen is adjusted to the chart baseline and insect feeding is monitored for 180 minutes. A chart speed of 1.5 cm/min at 500 mV amplifier power is adequate for distinguishing various waveforms and associated voltage reversals. Each treatment including the control is replicated ten times. The evaluation is based on the reduction in phloem feeding compared with controls. Phloem feeding shows erratic response in treated plants, evidenced by repeated voltage reversals in associated waveforms, which indicates the antifeedant behavior (Saxena and Khan, 1985).

OTHER MISCELLANEOUS METHODS Simulation bioassay Higgins and Pedigo (1979b) developed a simulation bioassay procedure to demonstrate feeding deterrence in phytophagous insects. This method involved rearing of two cohorts of green clover worm larvae, Plathypene scabra (F), under optimal conditions, but separated in

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time of oviposition by 3 days. Thereafter the mean development of the cohort to be used in the chemically defined treatments remained 3 days ahead of the average age and development of the physically stressed individuals. Trifoliates of the primary host, soybean (Glycine max), always were available in amounts exceeding requirements during the pre-experimental rearing period. Twenty-four hours before experimental initiation, larvae were removed from the growth chamber and allowed to acclimatize to room temperature. Upon reaching fourth stage plus 1 day, larvae in the chemically treated cohort were individually presented premeasured leaves selectively dip treated with solutions of guazitine triacetate and allowed to feed for 48 hours in 0.55 liter paper cartons. No significant larval weight differences existed at this stage (test initiation). Every 48 hours until pupation or death, leaves were replaced with equivalent treated trifoliates. Damaged leaves were removed and remeasured to determine the mean of 48 h consumption (An) under chemical stress. This cycle was then replaced until pupation or population extinction through toxicity or starvation. Upon reaching 4th stage +1 larvae of the second cohort (physically stressed) were presented untreated leaf material (Bn) equal in area to the mean daily consumption ±SE of the equivalently aged larvae feeding on chemically treated leaves. Preliminary trials revealed that split offerings of the food into 24 h treatments (Bn and Bn') would more closely model the stress imposed by the antifeedant. Area Bn' = An – (actual mean of Bn), ±1SE of An/2 (maximum of 1 cm2). In this way equal amounts of food were available for consumption by each cohort. This delayed cycle of leaf exchange was continued until pupation or population death or until forced absolute starvation was caused by the lack of feeding by the chemically treated cohort. Larvae of the physical cohort were individually placed in 9.53 × 6.99 × 2.24 cm ventilated, clear plastic snap-lid boxes. To obtain the proper untreated area, leaves were measured and then remeasured after the tip of the terminal leaflet was turned under to simulate feeding loss. The area to be presented to the physical cohort (the area turned under) was found by subtraction. The area turned under was then adjusted, by allowing the leaf to refold until it was within the acceptable bounds set by the average daily consumption of the corresponding chemically treated cohort. The leaflet was then slightly creased and the cage was snapped shut on the fold line (turned under area inside larval cage). As area determination continued, an effort was made to maintain equal numbers of larvae above and below the true desired mean. Thus, mean areas presented to the physical cohort were equivalent ±1SE to that consumed by individuals of the chemical cohort. Two trials exhibited feeding restriction of 40 to 75% depending upon the level of treatment (Higgins and Pedigo, 1979b).

Dipteran Assays In a test against Phormia regina, an adjustable pipette rack was fashioned from wood to hold pipettes and vials (each vial containing one fly). Disposable pipettes of 100 µl capacity in 10 µl graduation were used in combination with 25 ml vials fitted with plastic caps. A central hole for entry of the pipette tip and several smaller ventilation holes were drilled in each vial cap. Male and female flies were used, raised on beef liver and maintained on skim milk powder and sugar. Test compounds were mixed with 0.5 molar stock solution (control) of sucrose at a concentration of 0.01 M and stored at 4˚C in darkness for the duration of each trial (6 days). To ensure that the fly could easily ingest the test solution, the pipette racks were adjusted to an angle that allowed the solution to be readily absorbed on Whatman No. 1 filter paper. Newly emerged adults (1, 3, and 5 days old) were anesthetized with carbon dioxide gas prior to transfer to the vials in which they were given one day to acclimate and starve. Eleven

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of the twelve pipettes on each rack were connected to vials containing flies and the 12th served as an evaporation control. Three of the four racks held pipettes with alkaloid diets and the fourth held the 0.5 M solution of sucrose control. Readings were taken 6 hours and 24 hours after the beginning of the trial to determine the volume consumed to the nearest microliter (Blades and Mitchell, 1986).

WireWorm (Melanotus communis) Assay For wireworms both choice and no-choice designs have been adopted (Villani and Gould, 1985). In the choice design two experiments were performed. Plexiglas containers of 2.5 cm3 (Experiment 1) and 30 × 15 × 4 cm (Experiment 2) were filled with moist soil. A treated potato section (Experiment 1) or treated corn seed (Exp eriment 2) was placed 2.5 cm below the surface at one end of each container and a control for each at the opposite end. A single corn wireworm was buried head downwards in the center of the container; 25 containers were used in Experiment 1 and 50 containers in Experiment 2. The containers were placed in the dark, and after 36 hours (Experiment 1) and 8 days (Experiment 2) baits were checked for feeding damage. A potato section or corn seed and sprout, which showed any indication of having been fed upon, was considered damaged. The no-choice test design was as above with the exception that only one bait, either treated or untreated (control), was placed in each Plexiglas container.

Boll Weevil Assay A 1% solution of test fraction or compound was used, and an unpunctured debracted bud from a greenhouse-grown cotton plant was dipped momentarily in the solution. Ten 1- or 2-day-old adult boll weevils unfed from time of emergence or starved for 24 hours were placed in a petri dish with one treated and one untreated bud (dipped in solvent alone) and held for 4 hours. Five control and five test dishes were prepared for each test. The number of feeding punctures per bud was counted under a dissecting microscope (Bird et al., 1987).

Scale Insect Assay Test for red scale, Aonidiella aurantii, and yellow scale, A. citrina, have been conducted by spraying (with an atomizer) half of a green lemon fruit with a dilution of 0.01 to 1.0% as an aqueous emulsion and covering the other half with parafilm to protect it. The crawlers were allowed to migrate from heavily infested lemons onto the treated lemons. The insects were counted after 5 and 25 days post-treatment. A similar test has been conducted for citrus red mite, Panonychus citri (Jacobson et al., 1978).

Sawfly Assay A standard bioassay for sawflies used a 7- to 10-cm twig of 1-year-old jack pine foliage. Foliage was stripped from the twig until ten pairs of needles remained at each end. Twigs were rinsed in distilled water and allowed to dry. Needles at one end of each twig were covered with the resin acid/methanol solution by pipetting a few drops at the base of the needle and allowing it to flow to the tip. Needles on the other end were treated with solvent only. A similar twig received the solvent at one end and nothing at the other, to serve as an additional control. The treated needles were allowed to dry at room temperature for a minimum of 30 minutes. The treated twig was suspended horizontally on an insect pin that passed through the center of the twig; the pin was then inserted through 6.2 cm2 moss-green

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paper and into a No. 11.5 rubber stopper. Five 4th or 5th instar sawflies, Neodiprion dubiosus, N. lecontei, and N. rugifrons, were placed on the needles at each end of the twig. Replicates were placed in an environmental chamber at 20˚C under continuous light. A test concentration was recognized as biologically active in inhibiting larval feeding if > 70% of the total number of larvae settled on the end treated with solvent only after 4 hours (Schuh and Benjamin, 1984).

Leaf Beetle Assay Matsuda and Senbo (1986) described a method to test feeding deterrents against leaf beetles of various families. The bioassay procedure was based on a comparison of nibbling by adult beetles on 2 × 2 cm filter papers. The assay chamber was composed of a plastic petri dish of 9 cm diameter and 1.5 cm in depth. Three 7-cm-diameter filter papers were immersed in 2 ml of water and were placed on the bottom of the petri dish, and a doughnut-like plastic disk (3 cm ID and 7 cm OD) was put on the papers. Four pieces of filter paper per dish were equidistantly placed on the doughnut-like disk. Filter papers were treated with 0.075 ml of test chemical in methanol; control papers were treated with carrier alone. Papers were allowed to dry for several minutes, then placed in a petri dish, four to a dish. Twenty adult beetles starved for 24 hours were released into a petri dish with test or control material. All assays were completed in darkness at 24 to 25˚C. Five replicates of test and controls were run for each compound tested. Twenty-four hours after release of the beetles, the feeding response was judged from the differences between test and control pieces and expressed as (- - -) = no nibbling, (- -) = less nibbling than controls, (±) = same nibbling as in controls, and (+) = more nibbling than controls. A negative score was considered to indicate feeding deterrence.

Oral Dosing In this procedure a preliminary assessment is made for potential feeding deterrent compounds. In fact, several earlier studies have shown that deterrent chemicals could be consumed after elimination of chemoreceptors. Recently cannulas have been used to place test compounds into the gut lumen via the oesophagous in order to avoid behavior rejection in some grasshoppers (Cottee et al., 1988). Sutherland et al. (1981) have also used cannulas for oral dosing of scarabid grubs. This technique, however, has problems particularly in handling, which induces deleterious and damaging effects to the foregut during ingestion. Another problem is that doses are necessarily sporadic and do not mimic normal intake patterns. Semi-microgelatin capsules have been successfully used with grasshoppers (Cottee et al., 1988), which conceals the taste completely and there is rapid release in the gut. However, this technique is not feasible for smaller insects and is time consuming. Another technique of oral dosing for feeding deterrents was recently demonstrated for various insect species (Usher et al., 1989). In this method deterrent solutions are enclosed inside lipid vesicles and suspended in non-deterrent solutions that can be offered to the insects to drink. Liposomes containing an aqueous solution can be formed in a number of ways, such as reverse phase evaporation, where reverse micelles are formed of phosphatidylcholine around the aqueous phase in an excess of diethyl ether. The ether is evaporated, causing the lipid to form bilayer vesicles, or liposomes, which are sized to approximately 1 µm in diameter by passage through a polycarbonate filter. The liposomes can be separated from any remaining deterrent in the surrounding medium by passage through a gel filtration column. The liposomes are collected in the void volume of the eluting solvent, while deterrent molecules not inside liposomes are retained in the column.

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In the assay each insect is weighed immediately before and after a drinking bout and the volume drunk determined by the weight change. Amounts drunk by control and treatment groups of insects are compared. Thus this technique is a very useful approach to dose insects with compounds that normally deter feeding. Some other processes on similar lines use microspheres, microcoating, and molecular encapsulation (Usher et al., 1989; Clancy et al., 1992).

Field Trials Not many studies are available where feeding deterrents have been used in large-scale field trials. The vast majority of feeding bioassays with plant-derived chemicals have been performed under laboratory (or in some cases greenhouse) conditions, although field tests of metal-containing fungicides as antifeedants have been done (Jermy and Matolcsy, 1967; Ascher, 1979). Though field tests have confirmed laboratory results for some naturally occurring chemicals (All and Benjamin, 1976; Metcalf et al., 1980), laboratory results cannot necessarily be extrapolated to field conditions due to: • • • • •

Alteration of the chemicals in the field by environmental factors Habituation of insects Use of artificial substrates in the laboratory experiments Insect movement away from treated plants Composition of the plant community (Lewis and van Emden, 1986)

In fact there is no specific procedural design devised for field evaluation of antifeedants. The procedures are similar to those used for conventional chemical pesticides and have been followed for various field trials in a similar fashion. Among the antifeedant plant chemicals, the most extensive field trials have been carried out with neem products, mostly due to broad international cooperation (Schmutterer and Ascher, 1987). Ladd et al. (1978) carried out the earliest neem seed extract evaluation in the field against Japanese beetles, Popillia japonica, using plots consisting of four to five plants. Similarly, field trials with Colorado potato beetles, European corn borer, diamond back moth, and various aphids have been conducted to show reasonable control by foliar application of neem extracts and azadirachtin (Isman et al., 1991; Lowery et al., 1993). The proceedings of the World Neem Conference held in Bangalore, India, in 1993 (Singh et al., 1996) reports 24 papers on successful field application of various neem-based formulations. These results show the effect of these formulations on a variety of insects like grasshoppers, rice pests, bean flies, various Helicoverpa species, cotton pests, pod borers, maize pests, fruit flies, mango hoppers, and others. Such studies definitely demonstrate the potential of antifeedants on a large scale. However, there is a need to evaluate other identified antifeedant compounds in the field to determine the practical application potential of such compounds.

REFERENCES Alford, A.R. and Bently, M.D. (1986) Citrus limonoid as potential antifeedants for the spruce budworm (Lepidoptera: Tortricidae). J. Econ. Entomol., 79, 35–38. All, J.N. and Benjamin, D.M. (1976) Potential of antifeedants to control larval feeding of selected Neodiprion saw flies (Hymenoptera: Diprionidae). Can. Entomol., 108, 1137–1143. Antonious, A.G., Saito, T., and Nakamura, K. (1984) Electrophysiological response of the tobacco cutworm, Spodoptera litura (F), to antifeedant compounds. J. Pestic. Sci., 9, 143–146.

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Ascher, K.R.S. (1979) Fifteen years (1963–1978) of organotin antifeedants: a chronological bibliography. Phytoparasitica, 7, 117–137. Ascher, K.R.S. and Meisner, J. (1973) Evaluation of methods for assay of phagostimulants with Spodoptera littoralis larvae under various conditions. Entomol. Exp. Appl., 16, 101–114. Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Withanolides and related ergostane-type steroids as antifeedants for larvae of Epilachna varivestis (Coleoptera: Chrysomelidae). Phytoparasitica, 9, 197–205. Argandona, V.H., Corcuera, L.J., Niemeyer, H.M., and Campbell, B.C. (1983) Toxicity and feeding deterrency of hydroxamic acids from graminae in synthetic diets against the green bug, Schizaphis graminum. Entomol. Exp. Appl., 34, 134–138. Bentley, M.D., Leonard, D.E., Stoddard, W.F., and Zalkow, L.H. (1984) Pyrrolizidine alkaloids as larval feeding deterrents for spruce budworm, Choristoneura fumiferana (Lepidoptera: Tortricidae). Ann. Entomol. Soc. Am., 77, 393–397. Berenbaum, M. (1986) Post ingestive effects of phytochemicals on insects: On paracelsus and plant products. In J.R. Miller and T.A. Miller (eds.), Insect Plant Interactions, Springer Verlag, New York, pp. 121–153. Bernays, E.A. and Chapman, R.F. (1978) Plant chemistry and acridoid feeding behaviour. In J.H. Harborne (ed.), Biochemical Aspects of Plant and Animal Coevolution, Academic Press, New York, pp. 99–141. Bernays, E.A. and DeLuca, C. (1981) Insect antifeedants, properties of an iridoid glycoside: ipolamide. Experientia, 37, 1289–1290. Blades, D. and Mitchell, B.K. (1986) Effect of alkaloids on feeding by Phormia regina. Entomol. Exp. Appl., 41, 299–304. Blaney, W.M., Simmonds, M.S.J., Evans, S.V., and Fellows, L.E. (1984) The role of secondary plant compounds 2,5-dihydroxymethyl-3,4-dihydroxy pyrrolidine as a feeding inhibitor for insects. Entomol. Exp. Appl., 36, 209–216. Bird, T.G. and Hedin, P.A. (1986) An improved feeding bioassay for the boll weevil (Coleoptera: Curculionidae). J. Econ. Entomol., 79, 882–886. Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) Feeding deterrent compounds to the boll weevil, Anthonomus grandis Boheman in Rose-of-Sharon, Hibiscus syriacus L. J. Chem. Ecol., 13, 1087–1097. Clancy, K.M., Foust, R.D., Huntsberger, T.G., Whitaker, J.G., and Whitaker, D.M. (1992) Technique for using microencapsulated terpenes in lepidopteran artificial diets. J. Chem. Ecol., 18, 543–560. Cottee, P.K., Bernays, E.A., and Mordue, L. (1988) Comparisons of deterrency and toxicity of selected secondary plant compounds to an oligophagous and a polyphagous acridid. Entomol. Exp. Appl., 46, 241–247. Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) Aphid feeding deterrents in sorghum: Bioassay, isolation and characterization. J. Chem. Ecol., 7, 273–284. Escoubas, P., Lajide, L., and Mitzutani, J. (1993) An improved leaf-disk antifeedant bioassay and its application for the screening of Hokkaido plants. Entomol. Exp. Appl., 66, 99–107. Harmatha, J. and Nawrot, J. (1984) Comparison of the feeding deterrent activity of some sesquiterpene lactones and a lignin lactone towards selected insect storage pests. Biochem. Syst. Ecol., 12, 95–98. Higgins, R.A. and Pedigo, L.P. (1979a) Evaluation of guazatine triacetate as an antifeedant feeding deterrent for the green cloverworm on soybean. J. Econ. Entomol., 72, 680–686.

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Higgins, R.A. and Pedigo, L.P. (1979b) A laboratory antifeedant simulation bioassay for phytophagous insects. J. Econ. Entomol., 72, 238–244. Hosozawa, S., Kato, N., Munakata, K., and Chen, Y.L. (1974) Antifeedant substances for insects in plants. Agric. Biol. Chem., 38, 1045–1048. Isman, M.B., Koul, O., Arnason, J.T., Stewart, J., and Salloum, G.S. (1991) Developing a neem based insecticide for Canada. Mem. Ent. Soc. Can., 159, 39–47. Jacobson, M., Reed, D.K., Crystal, M.M., Moreno, D.S., and Soderstrom, E.L. (1978) Chemistry and biological activity of insect feeding deterrents from certain weed and crop plants. Entomol. Exp. Appl., 24, 448–457. Jermy, T. and Matolcsy, G. (1967) Antifeedant effects of some systemic compounds on chewing phytophagous insects. Acta. Phytopath. Acad. Sci. Hung., 2, 219–224. Jermy, T., Hanson, F., and Dethier, V. (1968) Induction of specific food preference in lepidopterous larvae. Entomol. Exp. Appl., 11, 211–230. Jones, C.G. (1979) An automatic feeding detector (AFD) for use in insect behaviour studies. Entomol. Exp. Appl., 25, 112–115. Jones, C.G. and Coleman, J.S. (1988) Leaf disk size and insect feeding preference, implications for assays and studies on induction of plant defense. Entomol. Exp. Appl., 47, 167–172. Koul, O. (1993) Plant allelochemicals and insect control: An antifeedant approach. In T.N. Ananthakrishnan and A. Raman (eds.), Chemical Ecology of Phytophagous Insects, Oxford & IBH Publishing Co. Pvt. Ltd., pp. 51–80. Koul, O., Smirle, M.J., and Isman, M.B. (1990) Asarones from Acorus calamus L. Oil: Their effect on feeding behaviour and dietary utilization in Peridroma saucia. J. Chem. Ecol., 16, 1911–1920. Koul, O., Shankar, J.S., and Mehta, N. (1997) Antifeedant activity of neem seed extracts and azadirachtin to cabbage aphid Brevicoryne brassicae (L). Ind. J. Expt. Biol., 35, 994–997. Ladd, T.L., Jacobson, M., and Buriff, C.R. (1978) Japanese beetles: extracts from neem tree seeds as feeding deterrents. J. Econ. Entomol., 71, 810–813. Lewis, A.C. and Bernays, E.A. (1985) Feeding behaviour selection of both wet and dry food for optimal growth by Schistocerca gregaria nymphs. Entomol. Exp. Appl., 37, 105–112. Lewis, A.C. and van Emden, H.F. (1986) Assays for insect feeding. In J.R. Miller and T.A. Miller (eds.), Insect Plant Interactions, Springer Verlag, New York, pp. 95–119. Lidert, Z., Taylor, D.A.H., and Thirungnanam, M. (1985) Insect antifeedant activity of four prieurianin type limonoids. J. Nat. Prod., 48, 843–845. Lowery, D.T. and Isman, M.B. (1993) Antifeedant activity of extracts from neem, Azadirachta indica to strawberry aphid Chaetosiphon fragaefolii. J. Chem. Ecol., 19, 1761–1773. Lowery, D.T., Isman, M.B., and Brard, N.L. (1993) Laboratory and field evaluation of neem for the control of aphids (Homoptera: Aphididae). J. Econ. Entomol., 86, 864–870. Ma, W.-C. (1977) Alteration of chemoreceptor function in armyworm larvae (Spodoptera exempta) by a plant-derived sesquiterpenoid and by sulfhydral reagent. Physiol. Entomol., 2, 199–207. Matsuda, K. and Senbo, S. (1986) Chlorogenic acid as a feeding deterrent for the Salicaceae feeding leaf beetle, Lochmaeae capreae cribrata (Coleoptera: Chrysomelidae) and other species of leaf beetles. Appl. Ent. Zool., 21, 411–416. Meisner, J. and Ascher, K.R.S. (1973) Attraction of Spodoptera littoralis larvae to colours. Nature London, 242, 332–334. Messchendorp, L., van Loon, J.J.A., and Gols, G.J.Z. (1996) Behaviour and sensory responses to drimane antifeedants in Pieris brassicae larvae. Entomol. Exp. Appl., 79, 195–202.

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Metcalf, R.L., Metcalf, R.A., and Rhodes, A.M. (1980) Cucurbitacins as kairomones for diabroticite beetles. Proc. Natl. Acad. Sci. USA, 77, 3769–3772. Mittler, T.E. and Dadd, R.H. (1962) Artificial feeding and rearing of the aphid, Myzus persicae (sulzer) on a completely defined synthetic diet. Naturre London, 195, 404. Nakanishi, K. and Kubo, I. (1977) Studies on warburgnal, muzigadial and related compounds. Israel J. Chem., 16, 28–31. Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Deterrent properties of sesquiterpene lactones for the selected storage pests. Proc. Nauk. Inst. Ochr. Roslin, 24, 27–36. Numata, A., Katsuno, T., Yamamoto, K., Tomoko, N., Tsuruko, T., and Seto, K. (1984) Plant constituents biologically active to insects IV. Antifeedants for the larvae of the yellow butterfly, Eurema hecabe mandarina in Arachniodes standishii. Chem. Pharm. Bull., 32, 325–331. Paruch, E., Ciunik, Z., Nawrot, J., and Wawrzencyzk, C. (2000) Lactones. 9. Synthesis of terpenoid lactones: active insect antifeedants. J. Agric. Food Chem., 48, 4973–4977. Reed, D.K. and Jacobson, M. (1983) Evaluation of aromatic tetrahydropyranyl ethers as feeding deterrents for the striped cucumber beetle, Acalymma vittatum. Experientia, 39, 378–380. Reese, J.C. and Field, M.D. (1986) Defence against insect attack in susceptible plants. Black cutworm (Lepidoptera: Noctuidae) growth on corn seedling and artificial diets. Ann. Entomol. Soc. Am., 79, 372–376. Rose, A.F., Jones, K.C., Hadden, W.F., and Dreyer, D.L. (1981) Grindelane diterpenoid acids from Grindelia humilis, feeding deterrency of diterpene acids towards aphids. Phytochemistry, 20, 2249–2255. Rowan, D.D. and Gaynor, D.L. (1986) Isolation of feeding deterrents against argentine stem weevil from ryegrass infected with the endophyte. J. Chem. Ecol., 12, 647–658. Saxena, R.C. and Khan, Z.R. (1985) Electronically recorded disturbances in feeding behaviour of Nephotettix virescens (Homoptera: Cicadellidae) on neem oil treated rice plants. J. Econ. Entomol., 78, 222–226. Scheffrahn, R.H. and Rust, M.K. (1983) Dry wood termite feeding deterrents in sugar pine and antitermite activity of related compounds. J. Chem. Ecol., 9, 39–55. Schmutterer, H. and Ascher, K.R.S. (1987) Natural pesticides from neem tree (Azadirachta indica A. Juss) and other tropical plants. Proc. 3rd Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany. Schoonhoven, L.M. (1982) Biological aspects of antifeedants. Entomol. Exp. Appl., 31, 57–69. Schuh, B.A. and Benjamin, D.M. (1984) The chemical feeding ecology of Neodiprion dubiosus Schedl., N. rugifrons Midd., and N. lecontei (Ritch.) on Jack Pine (Pinus banksiana Lamb.). J. Chem. Ecol., 10, 1071–1079. Shang, Z., Zhao, W., Zhu, Y., and Li, Q. (1993) The use of electrophysiological technique to explore antifeedants in plants. Prog. Natural. Sci., 3, 530–534. Singh, R.P. and Pant, N.C. (1980) Lycorine: A resistant factor in the plants of subfamily Amaryllidodieae (Amaryllidaceae) against desert locust, Schistocerca gregaria. Experientia, 36, 552–553. Singh, R.P., Chari, M.S., Raheja, A.K., and Kraus, W. (1996) Neem and Environment, Vol. 1, Oxford & IBH Publishing Co. Pvt. Ltd., New Delhi. Sutherland, O.R.W., Hutchnis, R.F.N., Russel, G.B., Lane, G.A., and Biggs, D.R. (1981) Biochemical plant resistance mechanisms: an evaluation of basic research. In K.E. Lee (ed.), Proc. Third Aust. Conf. Grassl. Invert. Ecol., S.A. Govt. Printer, Adelaide, pp. 245–253.

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Thomas, H.A. and Bradley, E.L. (1975) Feeding deterrents for the pales weevil in a laboratory bioassay. J. Econ. Entomol., 68, 147–149. Usher, B.F., Bernays, E.A., Barbehenn, R.V., and Wrubel, R.P. (1989) Oral dosing of insects with feeding deterrent compounds. Entomol. Exp. Appl., 52, 119–133. Villani, M.G. and Gould, F. (1985) Screening of crude plant extracts as feeding deterrents of the corn wire worm, Melanotus communis. Entomol. Exp. Appl., 37, 69–75. Warthen, J.D. Jr., Redfern, R.E., Uebel, E.C., and Mills, G.D. Jr. (1982) Antifeedant screening of 39 local plants with fall armyworm larvae. J. Environ. Sci. Health, 17A, 885–895. Wolfson, J.L. (1988) Bioassay techniques: An ecological perspective. J. Chem. Ecol., 14, 1951–1963. Wolfson, J.L. and Murdock, L.L. (1987) Method for applying chemicals to leaf surfaces for bioassay with herbivorous insects. J. Econ. Entomol., 80, 1334–1336. Zalkow, L.H., Gordon, M.M., and Lanir, N. (1979) Antifeedants from rayless goldenrod and oil of pennyroyal: Toxic effects for the fall armyworm. J. Econ. Entomol., 72, 812–815.

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4 STRUCTURE-ACTIVITY RELATIONSHIPS Biologically active compounds are found among all major classes of secondary plant substances and especially among the higher oxidized metabolites. The diversity of structures is usually large, and many of the biological effects are interpreted in terms of plant defense against predation and pathogenecity. Insect antifeedants are one of such biologically active substances that induce the cessation of feeding either temporarily or permanently. Various aspects of behavioral physiology in response to such chemicals have been described in the previous chapter, but quantitative structural-activity relationships have posed several problems. The overall picture that emerges from various evaluations shows that small structural variations can produce drastic changes in the activity profile of compounds. A critical examination of functional groups present in the active molecules provides crucial information about the optimal relative stereochemistry required to stimulate an antifeedant response in insects, but an analysis based on functionality and skeletal types appears to be difficult to produce any generalization, albeit one can certainly discuss activity variations within a skeletal type. The main aim of this chapter is directed in this direction and generalizes sufficient structure-activity information within specific skeletal systems to allow rational modification of readily available feeding deterrents to be made into potential insect control agents. Accordingly some specific class of compounds will be discussed in terms of structural-activity relationships to bring forth some generalizations.

LIMONOIDS This group of compounds, today, are considered to be most potential antifeedant allelochemicals that could be introduced in an Insect Pest Management (IPM) system. A specific example like azadirachtin (1), a tetranortriterpenoid from the Indian neem tree Azadirachta indica, is

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Opender Koul

known for its potent antifeedant characteristics (Koul, 1992). It is widely reported that azadirachtin affects the feeding behavior of many insect species (Koul, 1996), and a variation in the structure influences the activity of this compound (Blaney et al., 1990; Rembold, 1989; Ley et al., 1993). For instance, hydrogenation of the dihydrofuran ring as in dihydroazadirachtin (4) does not affect the activity of the molecule, and esters on the A ring do not affect the activity of the compound (Yamasaki and Klocke, 1987), although they could be important in transporting the compounds to the receptor sites. The difference in the level of antifeedance, for instance, among compounds 1 to 7 evaluated against four noctuid larvae (Blaney et al., 1990), has been attributed to the ability of the respective esters at C-1 or C-3 to transport the molecule to the target site. COOCH3 R1O

COOCH3

R4

O

OH

R1O

11

22

O

1

1

3

O OR3

R2O O

O

23

3

O

O

OR3

R 2O O

H3COOC

O (1) R1 =

OH

11

O

H3COOC

R4

O

O , R2 = Ac, R3 = H, R4 = OH

(4) R1 =

, R2 = Ac, R3 = H, R4 = OH

O (2) R1 = H, R2 =

, R 3 = R4 = H

(5) R1 = 2 methylbutenate, R2 = Ac, R3 = H, R4 = OH (6) R1 = pyruvate, R2 = Ac, R3 = H, R4 = OH

(3) R1 = R2 = R3 = R4 = H (7) R1 = R3 = H, R2 = Ac, R4 = OH

However, change in C-1 or C-3 ester in combination with a structural variation at C-11 resulted in decrease of feeding deterrent activity, especially in H. armigera. This suggests that the type of ester present at C-11 is important. These results also show that hydrogenation of C-22,23 double bond in azadirachtin does not significantly influence antifeedant activity, thus confirming the observations of Yamasaki and Klocke (1987). Hein et al. (1999) also report the hydroxy group at C-11 in azadirachtin A is important for high mortality rates, and a single bond between C-22 and C-23 increases the degree of efficiency. An exchange of the large ester group ligands at C-1 and C-3 with hydroxy groups in combination with a single bond between C-22 and C-23 and a hydroxy group at C-11 leads to high feeding activity and a degree of efficiency of about 100 percent. Ley and his co-workers have synthesized a large number of compounds to establish structure-activity relationships. Ley et al. (1993) report screening of 31 compounds related to azadirachtin against Spodoptera littoralis and point to the importance of hydroxyfuranacetal moeity in the high level of potency of this compound. Stereochemistry at C-7 is crucial, and the bridging oxygen substituent at C-6 may play some role. The precise spatial and electrostatic requirements of all the various oxygen substituents, according to Ley, need more detailed studies. These studies also reveal reduction in activity by increasing bulk at C-23. However, similar things do not hold true for other evaluated species like S. frugiperda or H. armigera. In fact the bulky isopropoxy substitute results in a compound with very potent antifeedant activity against S. frugiperda (Blaney et al., 1990) and less bulky ethoxy substitution quite active against H. armigera.

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Insect Antifeedants φ8

O O O

φ7 OH O 11 φ11 O D

1 O

φ3

φ4

CH3C

3

φ6

B

A

OH φ12 F

φ9 O φ10

C C φ5

8

13 E 14

7

4

O CH3O

OCH3

C

φ2 φ1

45

20

G O

OH

O

O

FIGURE 4.1 Azadirachtin key structural features. The designation of torsional angles and notation of the different rings are shown.

These studies, therefore, imply that large numbers of functional groups present in azadirachtin and the sensitivity of azadirachtin in different bioassays exhibit variable results. Therefore, the question still remains that specificity of structural features responsible for such an activity remains unpredicted. A recent theoretical study on the conformations of azadirachtin has provided some cruical information by critically examining the functional groups present in this compound and its methyl ether derivatives, which provide the data about the optimal relative conformations required to stimulate antifeedant response (Baldoni et al., 1996). In this study, uniform scanning using molecular mechanics calculations were carried out, and accordingly the conformations arising from the combinations of torsional analysis φ – φ (Figure 4.1) were considered (Dewar et al., 1985). In order to obtain a structure-activity relationship, the results obtained for azadirachtin were compared with those for its 7-methyl ether derivatives (Figure 4.2). In case of azadirachtin the substituents at C-1, C-3, C-4, and C-11 showed a moderate but significant conformational flexibility; in contrast, the tricyclic dihydrofuran ring showed a restricted rotation about the single bond with a highly preferred conformation at φ 9 ≈ 70°. Similar conformations were obtained for methyl ether derivatives. However, different results were obtained for the energy profiles, which reflected the influence of the dihydrofuran ring orientation. After comparing various results it was obvious that OH groups at C-11 and C-20 could collectively play a significant role in conferring the appropriate structural conformation and thus significant decrease in activity. Similarly the monomethyl substituent on C-7, C-11, or C-20 may not be critical to confer the structural conformation leading to biological activity for these compounds. In contrast, the presence of two methyl groups at C-11 and C-20 respectively or trimethylation introduces important changes in the conformational behavior of these compounds, which may be responsible for the lack of the activity (Baldoni et al., 1996). Similar studies with 3-tigloyl azadirachtol and other derivatives of azadirachtin have established that lack of antifeedant activity of 7-keto derivative and other inactive compounds can be explained on the basis of their different conformational behavior (Baldoni et al., 1997). For instance, on the three 2D conformational energy maps a total of 18 conformations were selected on energetic grounds for 3-tigloyl azadirachtol from molecular mechanism calculations. These data together with other experimental findings on the antifeedant activity of closely related compounds suggest that specific ester groups are not required at positions C-1 and C-3 in the azadirachtin nucleus in order to maintain a high level of activity. However, the presence of certain ester groups (e.g., tigloyl) at these positions may provide a favorable hydrophilic/lipophilic balance, necessary for optimum transport across various membranes

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Opender Koul COOCH3

O O

O

COOCH3

O

OH

OH

O

11

OCH3

O

O

O

13 14

1

20 O

O OCH3

CH3COO

3

H

COOCH3

O OH O

11

OH

O

O

O

13 14

20

7

O

O OH

3

H

OCH3

AZADIRACHTIN-7,20-METHYLETHER

COOCH3

COOCH3

O

OH

OCH3

O

O

13 14

20

1

8

H3COOC

O

O OH

CH3COO

13 14

20

7

7 4

OCH3

11 O

3

OCH3

O

11 1

H

O

H3COOC

O

O

O

CH3COO

AZADIRACHTIN-11-METHYLETHER

O

7

4

O

O

20

8

CH3COO H3COOC

13 14

1

8 4

OCH3

11

1 3

H

AZADIRACHTIN-7,11-DIMETHYLETHER

OCH3

O

OCH3 O

H3COOC

COOCH3 O

O

O

CH3COO

AZADIRACHTIN-7-METHYLETHER

O

7

4

O

H3COOC

20

8

7

4

13 14

1

8 3

OH

11

3

8

4 H

OH

CH3COO

O

AZADIRACHTIN-20-METHYLETHER

H3COOC

O

O H

O

AZADIRACHTIN-11,20-METHYLETHER

FIGURE 4.2 7-methylether derivatives of azadirachtin

and physiological partitions, as these molecules make their way to their target sites or receptors — an observation made by earlier workers as well. It is essential, therefore, to point out here that the highest level of biological activity was obtained when C-1 and C-3 positions were occupied by only OH functional groups (Hansen et al., 1994). Another interesting example of a limonoid from neem showing potential antifeedant activity is salannin (Yamasaki and Klocke, 1989; Koul et al. 1996). Fourteen derivatives of salannin (8) when bioassayed against Colorado potato beetle, Leptinotarsa decemlineata, larvae have revealed four target points which after modification change the activity pattern of salannin. These targets are (i) hydrogenation of the furan ring, (ii) replacement of the acetoxy group, (iii) modification of the tigloyl group, and (iv) saponification of the methyl ester. The hydrogenation of the furan ring to the tetrahydrofuran ring increases the antifeedant activity. The replacement of the acetoxy group at position 3 by a methoxy group increases

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Insect Antifeedants

47

the activity, and a similar increase occurs when the acetoxy group at position 3 is replaced by hydrogen. The modification of a tigloyl function, such as hydrogenation, increases the activity at least twofold. On the contrary, deesterfication of the tigloyl or the α-methyl butyrene groups result in a reduction of activity. Saponification of the methyl ester at C-11 increases the activity, for instance, salannic acid (9) is at least eightfold more active than 1,3-diol derivative (10). O

O

OH

O

O

O

OH

O

3

O

3

O

O

CH3COO

HO O

O

(8)

(9)

O O O O

OH

O

O

O

O

3 O

O

7

HO

OH O

(10)

(11)

However, other derivatives in which the methyl ester is chemically modified need to be prepared in order to ascertain the activity of the carbomethoxyl group (Yamasaki and Klocke, 1989). Another group that has shown potential as antifeedant limonoids is that of citrus limonoids. It appears that furan and epoxide groups have to play a major role in the activity of these compounds. A possible role of C-7 is implied by the modest activity of the 7-hydroxylated de-epoxy system (Bentley et al., 1988). For instance, highly reduced activity of deoxyepilimonol (11) against epilimonol (12) and Limonin (13) demonstrate the above conclusion. In certain cases the cyclohexenone A ring and the α-hydroxy enone group in the B ring appear to be important for antifeedant activity. Also, the absence of 14-15 epoxide may not drastically reduce antifeedant activity (Govindachari et al., 1995). Recently, 23 semisynthetic derivatives of citrus limonoids, with a focus on the changes in C-7 carbonyl and the furan ring, have been evaluated against Spodoptera frugiperda larvae. In particular, reduction at C-7 afforded the related alcohols, and from these their acetates, oximes, and methoximes were prepared. Hydrogenation of the furan ring was also performed on limonin and obacunone to establish the significance of the furan ring in the antifeedant activity against insects (Ruberto et al., 2002).

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48

Opender Koul

O

O O

O

O 14 O

O

O

C

D 14

15 O

O

7

O

A

A'

O

B

7

15 O

O O

OH

(12)

(13)

If we look at the overall system of limonoid compounds there are several impediments to developing a quantitative understanding of structure-activity relationships. Different investigators seldom utilize the same bioassay species, interspecific differences in the response of the test insect can easily mask any meaningful observations, and differences in larval stadium make comparisons invalid (Champagne et al., 1992). Although some specific examples from neem and citrus have been discussed above and despite the difficulties inherent in comparing data from such diverse array of studies, some qualitative trends could be generalized. Aside from the C-seco limonoids mentioned above, the most active compounds appear to be intact apo-euphol limonoids (14) with a 14,15-epoxide and either a 19/28 lactol bridge or a cyclohexenone (3-oxo-1-ene) A ring. Absence of the 14,15-epoxide results in reduced activity as with azadiradione (15) in comparison to cedrelone (16) or anthothecol (17). OH O O OH O

OAc

O

HO

(14)

(15)

O

O

R

14 15 O O

O

O

(16) R
H (17) R
OH

O

O O

OAc

OH

(18)

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Insect Antifeedants

49

Oxidation to a D-seco limonoid (18) appears to correlate with reduced activity. For example, azadirone (19) is almost inactive as a feeding deterrent, but the 16-keto intermediate azadiradione (20) is quite active. Further oxidation to 14-epoxy-azadiradione (21) results in considerable loss of activity, which is scarcely improved by formation of the lactone-D ring in gedunin (18).

O

O

16

O

OAc

O

O

OAc

(19)

(20)

O

O AcO

O

O O

O

O

O O

O

O

OAc

(21)

(22)

O

OAc O OH

O

O

O

O

O

O

O O

O

AcO

OH

AcO H

(23)

(24)

The A,D-secolimonoids like liminin (13), nomilin (22), and obacunone (23) are usually less active than D-seco and many apo-euphol compounds. Model compounds based on the C and D rings, the associated furan ring are slightly more active than limonin, suggesting that this region of the molecule is most critical for bioactivity (Bently et al., 1990). However, few A, B, or B-seco limonoids seem to be less active than above A,D-seco limonoids, but it

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Opender Koul

is difficult to ascertain functional comparisons due to substantial variability in bioassay procedures. At this point of time it is not possible to draw any specific conclusions due to the paucity of structure-activity data based on monophyletic biosynthetic pathways of limonoids and the process of ring modification represented by the O and S values, which are likely independent of each other. However, there is some relationship in structure activity to some cytotoxicity studies against mammals. Pettit et al. (1983) bioassayed 38 limonoids from Meliaceae and Rutaceae for inhibition of a murine P-388 lymphocytic leukemia cell line. The most active compounds were 14,15-epoxy D ring and a 19-28 lactol bridge compounds like sendanin (24). Compounds with the epoxide and a 3-oxo-1-ene A ring (anthothecol) were somewhat less active and the reduction of the olefin eliminated the activity. In a very recent study, structure-related insect antifeedant relationship of 56 limonoids of both natural ones from various plants and modified forms belonging to the order Rutales was attempted, considering substitution patterns, oxidation states, and hydrophobicity, as well as distant geometry derived through conformational analysis on molecular modeling. It was demonstrated that orientation of the furan and hydroxylation at specific carbon sites influence the antifeedant activity against Spodoptera litura (Suresh et al., 2002). These studies suggest that molecular modeling could be a significant helping tool for designing of compounds. For instance, relaxed bond distance between oxygen atom at C-3 and C-20 of the azadirachtin molecule was found comparable to that of 20-β-hydroxyecdysone, which has a significance in binding to ecdysone receptors; therefore, such a change of the distance between the active sites could have an impact on antifeedant activity as well. These studies also suggest that the most active limonoid could be either an intact apoeuphol compound or a C-seco compound with a hydroxylated furan (an –OH that may overlap with a C-20 –OH in azadirachtins) and a dihydroxy A-ring.

QUASSINOIDS Quassinoids, which are, like limonoids, degraded triterpenes, exhibit some structural relationship vis-a-vis the antifeedant activity. Discovery of bruceantin (25), a quassinoid from Brucea antidysenterica, as a potent antineoplastic compound has generated tremendous interest in quassinoid type of natural and synthetic biologically active compounds (Lidert et al., 1987). Apart from anticancer, antiviral, antiamoebic, antimalarial, and anti-inflamatory properties of such compounds, quassinoids possess anti-insect properties as well, particularly the feeding deterrent effects (Leskinen et al., 1984). The structure activity correlation pattern OH COOCH3

HO O O

OCO A

HO

O

O

(25)

for the feeding inhibition, as demonstrated against tobacco budworm, Heliothis virescens, can be summarized as follows:

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Insect Antifeedants •

51

The A-ring enerone function is essential for activity. Reduction of the electrophilic capacity of this michael acceptor results in lowering of activity. Thus the A-ring diosphenols are on the whole less active, as can be seen in compounds 26 versus 27 (Lidert et al., 1987). However, higher electrophilicity of diosphenol achieved by placement of the electron withdrawing trifluoromethyl sulfonyl substituent onto the 3-hydroxy group (28) did not result in increased activity. OH

OH COOCH3

HO

HO

O

O

HO

O

O

O

O

COOCH3

HO

OCO

O

O

(26)

(27) OH COOCH3

HO O O

OCO A

SO2F3CO

O

O

(28)

•

•

The C-ring oxomethylene bridge is very important (compound 29 is of poor activity). C-8 and C-13 linkages seem to be somewhat more advantageous than C-8 to C-11 (compound 30 versus 31 and 32). Ester side chains have in many cases great influence on activity (compound 33 more active than 34). On the whole hydrophilic side-chains seem to be deterimental (35 versus 36) while hydrophobic, unsaturated side chains improve activity (37, 38). OH

HO O

HO C

O

O

(29)

Compounds lacking side chains altogether can be fairly active (30). Their pattern of structure-activity relationships is similar to the ones reported by other workers, too (Klocke et al., 1985; Odjo et al., 1981).

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52

Opender Koul OH

OH

HO

HO

HO

HO

O OH

O

O OH

O

OH O

O

O

(30)

O

(31) OH HO HO

O OCO

O

O

O

(32) OH

OH

HO

HO

OAc

OAc

O

O OCO

O

O

HO

OAc

O

O

HO

O

(33)

(34) OH

OH HO

HO

OAc

OAc

O

OCO

O

O

O

OCO

O

HO

(35) OH OAc

HO

HO

O

O

OCO

O

(37)

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O

(36)

OH

HO

OH

O

O

HO

O

O

OAc

HO O

O

OCO

O

O

(38)

Insect Antifeedants

53

DITERPENES Various diterpene acids and clerodane types of diterpenes have been identified from various plant sources and shown to deter feeding in various insect species (Hosozawa et al., 1974; Rose et al., 1981; Miyase et al., 1981; Koul, 1982; Wagner et al., 1983; Schuh and Benjamin, 1984; Belles et al., 1985; Enriz et al., 1994; Giordano et al., 2000). In fact, clerodanes occur in different isomeric forms, and the general problem of a structure-activity relationship exists here too, due to variability in bioassay evaluations. Nevertheless, it is possible to draw some conclusions. For instance taking clerodin (39) as the parent compound, changes in different carbons vis-a-vis the activity can be discussed. There are few derivatives that bear a substituent at C-1 as in ajugareptansin (40) and ajugareptansone A (41), but these are weak antifeedants. According to Belles et al. (1985) this may be accounted for by a Skew boat confirmation of the A ring, caused by sterical hinderence between substituents at C-1 and C-9. In clerodendrin A (42) aceylation at C-2 position results in a complete loss of activity; however, in Ivaine I (43), aceylation has no effect on the activity. O

O 15

O

O

14

16

O

O

O

COO

1

3

5 4

AcO

6

AcO

(39)

O

7 CO O

O

OAc

8

10

HO

O

9

1

2

OAc

AcO

(40)

(41)

O

O

O

O

HO

OAc

HO 2

2 COO

COO OAc

O AcO

(42)

OAc

O AcO

OAc

(43)

In any case, stereochemistry at C-2 is important, which is evident from higher activity in 14,15-dihydroajugapitin (44) than Ivaine IV (45). The substitution or stereochemistry at C-3 does not seem to affect the activity in any case. The epoxy ring also does not appear to

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Opender Koul

hinder the activity due to the similarity in activity among ajugarin II and III (46, 47) and tafricanins (48, 49). On the other hand, stereochemistry at C-4 seems to play an important role in the activity of these compounds. Several decalins with an epoxide of the opposite stereochemistry are less active (Ley et al., 1982; Geuskens et al., 1983) than otherwise identical decalins of the normal stereochemistry. O

O O

O

O

O

HO

HO 2

2

COO

COO O AcO

O

OAc

AcO

(44)

(45)

OAc

O

OH AcO

(46)

O

O

O O

(48) R1 = O, R2 = H, R3 = Cl, R4+R5 = O (49) R1 = O, R2 = R4 = H, R3 = Cl, R5 = OAc

R1 R2O

HO HO

AcO

OAc

R4 R3

R5

AcO

(47)

According to vanBeek and deGroot (1986), an important feature of the clerodane diterpenes might well be the α-CH2OAc side chain at C-5. All derivatives, including those with an intact epoxy group, lacking the acetyl substitution at C-19, are only very weakly active or inactive, like ajugarin V and clerodendrin A tetraol (50, 51). A loss of acetyl group at C6 does not affect the activity, as ajugarin I (52) and ajugarin II (46) do not differ in their antifeedant action. The necessity of some oxygen-containing substituent at C-9 is immediately obvious from the low level of activity of several synthesized decalins relative to clerodin and other natural clerodanes. Many different furofuran side chains in the ajugarin series and a furan side chain in the tefricanins all give rise to deterrent activity. Geuskens et al. (1983) suggest that activity of clerodanes is neither located in the side chain nor the decalin moiety alone but rather two groups appear to exert a synergistic effect on each other with regard to antifeedant activity.

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Insect Antifeedants O

55 O

O O

O O

HO

HO

O HO

O

OAc

HO

(50)

O

OH

AcO

(51)

OAc

(52)

Considering the feeding deterrent activity exhibited towards Tenebrio molitor of several diterpenes with clerodane skeleton using electronic and conformational behaviors (Enriz et al., 1994), they seem to mediate at least through two binding sites. The presence of an α,βunsaturated system, or one spiroepoxide substituent at C-4 in the clerodane structure, together with the β-furyl moiety at C-9 is important to evoke antifeedant activity. In addition the free rotation of the β-furyl group could play a significant role in the biological activity. These results will be apparently helpful in the structural identification and understanding of the minimal structural requirements for these molecules and can provide a guide in the design of compounds with antifeedant activity (Enriz et al., 1994). Enriz and his co-workers (2000) have further emphasized that steroelectronic factors are more important than the hydrophobic aspects. A conformational study indicates that the optimum interatomic distance between furan ring in the side chain and a spiro-epoxide range between 9.5 and 10.5 Å. They also found similar steroelectronic response among withanolides and azadirachtin, which for the first time gives an indication of a relative chemical mechanism for these compounds (Enriz et al., 2000). Certain structural transformations in this respect by synthesizing such derivatives have proved the importance of furan moiety and cleavage of the oxirane ring, which causes almost total disappearance of activity (Gallardo et al., 1996). To be precise the presence of β-axial spiro epoxy at C-4 together with β-ethylfuran ring, an ethyl butenolide or a hexahydrofurofuran substituent at C-9 is necessary to elicit the antifeedant activity of neoclerodanes against insects (Camps and Coll, 1993; Rodriguez et al., 1993; Malakov et al., 1994; Urones et al., 1995). Recently a new class of insect antifeedants, the ryanodine diterpenes (53), have been isolated from Persea indica (a Lauraceae plant). The structure-activity relationship of these compounds show that C-14 and C-1 substituents play an important role. Aceylation of these centers results in loss of activity, whereas pyrrolecarboxylate at C-14 (54) confers high OH

1 HO

OH O

14

R=

RO

C N

OH HO

O

(53)

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(54)

56

Opender Koul

potency (Gonzalez-Coloma et al., 1996). The comparisons of the mammalian toxicity and insect feeding deterrency of these compounds suggest a mechanism of action of these diterpenes in insects different from the Ca2+ release channel (Gonzalez-Coloma et al., 1996).

SESQUITERPENES Caryophyllene oxide, spathalenol, guaianol, helenalin, eupatoriopicrin, bakkenolide A, bisabolangelone, and various sesquiterpene lactones are active antifeedants against a variety of insect species (see Chapter 7). In fact antifeedant activity of a number of sesquiterpene lactones has been comprehensively reviewed (Picman, 1986), but as usual due to efficacy variabilities it has been difficult to generalize structural features responsible for this activity. Two conclusions that could be emphasized here are the importance of α-methylene group evidenced by diethylamine and methanol adducts of eupatolide being more deterrent than eupatolide (55). Michael type addition with the α-methylene on γ-lactone as well as with α,β-unsaturated ketone or with other exomethylenes could explain the activity of sesquiterpene lactones, which do not contain the α-methylene-γ-lactone moeity and, therefore, are worth consideration. Similarly antifeedant activity of 53 sesquiterpenes of Lactarius origin is known against stored grain pests (Daniewski et al., 1995). The sesquiterpenes with lactarane (56) and marasmane (57) skeletons are much more active than those with an isolactarane skeleton (58). The activity of furans is generally higher than their lactonic counterparts. The activity of furans depends upon the presence of hydroxyl groups in their molecules. The greater the number of OH groups the lower the activity. However, no simple correlation is possible between the antifeedant activity of lactones and the number of –OH groups in their molecules. A change in the position of a carbonyl group from C-5 to C-13 in the lactone ring does not improve the activity. Alteration in the natural characteristic configuration at C-8 causes a decrease in antifeeedant activity in both lactones and furans of lactarane skeleton (Daniewski et al., 1995). R1

OH

O

CH2

O

O

O

CH2R4 R2

O

(55)

O

(56)

(58)

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OH

O

OHC

R

(57)

OH

OH

O

R1

R3

HOH2C

OH

(59)

(60)

R2

Insect Antifeedants

57 CHO

CHO

OH

CHO

CHO

OH CHO

CHO

CH2

(61)

(62)

(63)

It could be further demonstrated that a mixture of hemiacetal and γ-hydroxyaldehyde form of isolactarane sesquiterpenes (59) are very active compounds compared with those that exist only in hemiacetal form (60) (Daniewski et al., 1997). Sesquiterpene drimane antifeedants like warburganal (61), polygodial (62), and muzigadial (63) are also known active compounds (Lam and Frazier, 1987) with a reactive enedial functionality that interacts with a chemoreceptor site via pyrrole formation. A series of natural drimanes and related synthetic compounds, when tested against aphids, show least activity due to polygodial or those compounds that do not possess the trans-decalin ring of the natural drimane aldehydes. Despite the high activity of (-) warburganal, of the other 9 α-hydroxy compounds only compound (64), the 9 α-hydroxy analogue of cinnamolide (65), is active. In fact, these compounds, which have been reported to be active against several species of Spodoptera and Heliothis (Blaney et al., 1987), are inactive against aphids. O

9 8

CHO OH

O O

CHO

(64)

(65)

(66)

At the molecular level most active dialdehydes have a double bond in common between C-7 and C-8 and an 11-12 β dialdehyde (Gols et al., 1996). The importance of such a configuration is supported by the lack of activity of compound (66) and (±) isotadeonal (67). The deterrence of lactones is higher when the lactone group is present at the C-8/C-9 position. Forty-one sesquiterpenes with a dihydro-β-agarofuran skeleton (68) and 14 related synthetic compounds have been evaluated against Spodoptera littoralis larvae (Gonzalez et al., 1997). These studies show activity in 38 compounds, the most active being those with isoalatol (69) and 4 β-hydroxyalatol (70) skeletons. Comparing the activities of the compounds with the same skeleton, the activity seems to increase with the number of acetate esters and decrease with the number of benzoate esters. In general products with aromatic esters at C-1 and C-9, whatever the stereochemistry, are moderately active. The introduction of ester groups at C-2 does not seem to change the activity of the compounds. CHO 11

9

1 8

12 CHO

2 3

8 10

A 4

7

5 6 O

14

(67)

© 2005 by CRC Press LLC

(69)

4β - OH, 9α - OBz, 1α,6β,15 - OAc, 8α OCH3

(70)

4β - OH, 9α - OBz, 2α,6β,8α,15 − OAc, 1α − OAng

B 7 C 12

11 13

(68)

58

Opender Koul

Silphenene sesquiterpenes are established chrysomelid antifeedants and have been evaluated against S. littoralis, L. decemlineata, Myzus persicae, Rhopalosiphum padi, Metopolophium dirhodum, Diuraphis noxia, and Sitobion avenae (Gonzalez-Coloma et al., 2002). Small structural changes (see Chapter 7) resulted in drastic differences in antifeedant activity, suggesting a high molecular selectivity for silphinene derivatives on chemoreceptors. The changes from angelate to acetate or tiglate or isobutyrate as C-5 substitution induces a great impact on the antifeedant potency. Esterification at C-5 with different substituents has strong effect on the activity (e.g., 5α-acetoxysilfinen-3-one; see Chapter 7) (Reina et al., 2002). Significant to moderate increase depending on the type of C-5 substituent (258-fold for ang., 187-fold for tig., 4-fold for isobut., and 3-fold for Ac) has been demonstrated (Reina et al., 2002). Importance of C-11 acetate has also been demonstrated and apparently the tricyclic silphinene sesquiterpenes are good antifeedant candidates for future study.

MONOTERPENES Many monoterpenes have been evaluated against insects to show feeding deterrence against them (Koul, 1982). However, capillin (71), capillarin (72), methyl eugenol (73), and arcurcumene (74) isolated from Artemisia capillaris have a promise as antifeedant compounds against cabbage butterfly larvae, Pieris rapae crucivora. The relative strong antifeedant activity of capillin and capillarin suggest that C=O carbonyl group instead of CH2 methylene group, a C ≡ C in a side chain, and a lactone ring are some of the many factors that contribute to the biological activity (Yano, 1987). Various derivatives of these base compounds like methyl eugenol reveal that the 3,4-dimethyl group and 1-substituent of 3,4-dimethoxy-1substituted benzenes (75) contribute to the antifeedant activity (Yano and Kamimura, 1993). Similarly capillin structure has an aromatic carbonyl group and two C ≡ C bonds. In order to demonstrate the importance of these two functions for the candidate activity, various derivatives evaluated against P. rapae crucivora reveal that arylmethyl ketone with a CH3 group (76), instead of an H atom combined with C = O group of aromatic aldehyde, is more active than that of aromatic aldehyde (Yano and Tanaka, 1995). Also a relationship between antifeedant activity using phenyl alkynes suggests that C ≡ C triple bond in the side chain is associated with antifeedant activity. It has also been observed that terminal groups (R) of side chain of C6H5-C≡C-R influences activity considerably, and the intensity of activity of various compounds shows a reasonable trend (77). This suggests that charge separation of C ≡ C triple bond by electron donative effect of alkyl group combination with C ≡ C bond may be correlated with an increase in antifeedant activity, and that a carbon chain enlargement of the alkyl group results in a decrease of antifeedant activity, probably because of the stereochemical hindrance (Yano, 1986). OCH3 OCH3

O O

O

(71)

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CH2

(72)

(73)

Insect Antifeedants

59

OCH3 OCH3

C=O R

R

(74)

R = CH3

(75)

(76)

>

>

>

> (77)

It has also been established that the 3,4-dimethoxy group and the 1-substituent of 3,4-dimethoxy-1-substituted benzenes related to methyl eugenol contribute to the activity. As for aromatic carbonyl compounds related to capillin, arylmethylketones [Ar – C(CH3)=O] became more active than aromatic aldehydes [Ar–C(H)=O], when an H atom of aldehyde group of aromatic aldehydes was replaced with a CH3 group (Yano, 1998).

COUMARINS Inhibitory activity of feeding by coumarins isolated from Atlanta recemosa and other related species against Spodoptera litura larvae have made it possible to draw some structural patterns for the said activity in this class of allelochemicals. Xanthotoxin (78) is known from decades to induce inhibitory effects in insects and accordingly has been shown to deter feeding as well (and so has its derivatives). Amongst these, xanthotoxol ethyl ether (79) has shown the highest feeding inhibition. Demethylated products like xanthotoxol (80) and its acetate (81) totally lack activity. Methyl and ethyl ethers of rutaretin (82), which are 2-(α-hydroxyisopropyl) dihydrofurano analogues of xanthotoxin are also inactive. Similarly 2-isopropylexanthotoxin (83) and its ethyl analogues (84) are also inactive (Luthria et al., 1989). OCH3 O

OC2H5 O

(78)

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O

O

OH O

(79)

O

O

O

(80)

O

60

Opender Koul OAc O

OR

OH O

O

O

R = CH3

O

O

or R = C2H5

(81)

(82)

OCH3 ipr

O

OC2H5 O

O ipr

O

O

O

(83)

O

O

O

(84)

(85)

OCH3 O O

O

O

OCH3

O

O

O

O

O

OCH3

(86)

(87)

(88)

OCH3 O

O

O

R1

O

O

OCH3

(89)

O

RO

O

R2

(90)

(91)

Psoralen (85), which has a linearly fused furan ring like xanthotoxin but lacks a methoxyl group, is moderately active. However, its isomer angelicin (86), with an angularly fused furan ring, shows several-fold reduction in activity. Isopimpinellin (87), which has an additional methoxyl group at C-4, is sixfold more active than the former compounds. An interesting observation is the least activity in luvangetin (88), racemosin (89) and xanthyletin (90), which are corresponding pyrano-analogues of xanthotoxin, isopimpinellin, and psoralen respectively. Substituted coumarins like umbelliferones (91) without furano and pyrano moieties are also inactive (Luthria et al., 1989). The conclusions that can be drawn from the comparisons are: • •

A linearly fused furan ring along with alkoxy groups at positions 4 and 9 play an important role in determining antifeedant activity. A substituent in the furan ring causes a loss of antifeedant activity.

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Insect Antifeedants

61

A series of 3-acyl-4-hydroxy coumarins structurally related to dicoumarol are also known to induce feeding inhibition in insects (Dreyer et al., 1987). It has been suggested that increase in 3-acyl group size in such compounds decreases the activity. These compounds are known antibacterial agents against gram positive bacteria but inactive against gram negative bacteria (Toda et al., 1958). Similar studies on furochromones have revealed some distinctive features responsible for antifeedant activity against insects (Luthria et al., 1993). The assumptions made on the basis of activity suggest that substitution at C-2 lowers the actviity (92 versus 93). Saturation of the 2,3-double bond as in 2,3-dihydronomellin (94) also diminishes the activity compared to that of khellin (95). Absence of cleavage of the furan ring results in drastic reduction in activity, which is evident from the reduced activity in chromones (96) and chromonones (97). Changes at the substituents at the pyrone ring (C-7 position) reduces activity. Thus compounds 98 and 99, which contain a CH2OH group at C-7 and are analogues of 92 and 95, are significantly active. The furanoflavones (100), the aryl analogues of 95, also do not show any significant antifeedant activity. O

Ac

O

O

2

O

> CH3O

CH2

(92)

O

(93) OCH3

OCH3

O

O

O

2

O

<

3

OCH3

OCH3

(94)

(95)

O

R4 R3

O

R2

R

R2

O

R1 O

R1

(96)

R

O

(97)

Similarly, benzofurans (101) obtained by the cleavage of the γ-pyrone rings of 95 and 92 do not deter feeding of the larvae, and saturation of the the 6,7 double bond of the pyrones causes reduction in activity (102). Thus an intact pyrone ring seems to be essential with methyl substitution at C-7 for inducing a potential feeding deterrence.

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Opender Koul OCH3 O

CH2OH

O

OCH3

O

O

CH2OH

O

O

OCH3

(98)

(99) OCH3 OCH3 O

O

R1

R2 O

OCH3

(100) R1

OCH3

OCH3 1

OH

O

O

O

O

2

O

7

3

6

R2

5

4 OCH3

OCH3

(101)

O

(102)

(103) OCH3

OH O O

O

OH

O

O

9

O

O

4

OH

(104)

O

OH

(105)

O

O

O

(106)

Another interesting aspect of the structure-activity relationship of these compounds is the alkoxy groups on the aromatic ring. Complete or partial dealkylation of compounds 95 and 92, as in compounds 103, 104, and 105, causes total loss of activity. On the other hand synthetic ethyl ether derivative (106) shows increased activity compared to the natural product (Luthria et al., 1993). A number of naturally occurring benzofurans that differ in their substitution pattern and oxidation state have been investigated for their ability to inhibit the feeding of third-instar larvae of common cutworm, Spodoptera litura, in a leaf disk bioassay. The introduction of methoxy and acetyl groups increased antifeedant activity. Insect antifeedant activity also increased with decreasing lipophilicity of the test compounds (Morimoto et al., 1999).

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Overall analysis of the activity suggests that among furanochromones the presence of an unsaturated furan ring and an alkoxy substitution at positions C-4 or C-9 are essential for antifeedant activity. Also both heterocyclic (furan and pyran) rings are essential. Cleavage or saturation of either of the heterocyclic rings as well as replacement of C-7 methyl diminishes the activity.

ISOFLAVONOIDS A comprehensive study against Costelytra zealandica using various naturally occurring isoflavonoids of different substitution patterns and oxidation states reveals that these compounds are significantly active in the range of 0.2 to 1.0 µg/g level (Russel et al., 1978; Lane et al., 1985). Out of 36 isoflavonoids including optical isomers, 18 are active antifeedants. Phaseolin (107) (and related compounds with a cyclic isoprenoid unit fused to ring B) and rotenone (108) are particularly active with a significant effect on feeding. The deterrent activity is not restricted to a particular isoflavonoid class. While all the pterocarpins (like 107) show feeding deterrence, none of the coumestans (109) are active. Similarly isoflavans, isoflavones, and isoflavonones belong to both active as well as inactive categories (Lane et al., 1985).

HO

O

7

O

2 A

C 3

6 5

4

D

C

A

6'

1'

O

5'

B 2'

O

6'

3' 4' OCH3

5'

α β

(108)

(107)

OCH3

(108) HO

O

O

2' B

O

3'

O

1'

4'

O

R

D

O

R1

O OH R = OH, R1 = H

(109)

or

R = H, R1 = OH

RO

O

R = H or R = CH3

(110)

Two structural features that are characteristic of most of the highly active isoflavonoid feeding deterrents are: • •

The presence of 2′-oxy function. The occurrence of a 2,2-dimethyl-1, H-pyran (cyclic isoprenoid group) fused to ring B (107, 110).

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Opender Koul

There is a difficulty of comparing inactive compounds with those of the marginal activity. However, the balance of evidence supports the view that the difference in activity between 2′-deoxy compounds and their 2′-oxy counterparts is real. Several inactive or marginally active compounds do contain 2-oxy function (109, 111, 112), and the contrast between the inactivity of the coumestans (109) and the active pterocarpins (107) suggests that 2′-oxygenation is a feature of all the active feeding deterrents of this class, but its occurrence does not correlate with activity.

HO

HO

O

H3CO

(111)

O

OH

O

HO

OH

OCH3

(112)

Recent studies with flavonoids against termites have revealed some basic requirements in a structure-activity relationship. It was found that compounds containing two hydroxyl groups at C-5 and C-7 in A-rings showed high antifeedant activity. Furthermore, the presence of a carbonyl group at C-4 in the pyran rings of the compounds was necessary for the occurrence of high activity. 3-Hydroxyflavones and 3-hydroxyflavanones with 3',4'-dihydroxylated B-rings exhibited higher activity than those with 4'-hydroxylated B-rings (Ohmura et al., 2000).

ALKALOIDS Various alkaloids have been evaluated in insect herbivore relationships (Levinson, 1976) and possess considerable toxicity and phagodeterrency effects against variety of organisms (Levin, 1976). Insect larval feeding deterrence due to pyrrolizidine alkaloids, lupine alkaloids, and solanum alkaloids (Chapter 7) is well known (Bentley et al., 1984a, 1984b, 1984c). However, from the structure-activity relationship point of view there is a wide variation in feeding response to alkaloids in different species of insects. Even in the studies against the same species, like spruce budworm (a species with a rather narrow range of coniferous host plants that do not contain glycoalkaloids; therefore, a fortuitous choice of a test insect), it is still difficult to generalize any functionalities responsible for activity in these compounds. What has been postulated is that at least with alkaloids, the evolution of host–herbivore interactions may be a function of the class of alkaloids present or of nonchemical selective factors (Bentley, 1984c). However, in case of lycorine alkaloids, increase in nucleophilicity attributes to increased activity (Evidente et al., 1986) and an undissociated phenolic group leads to a marked decrease in activity. The insect antifeedant activity of the Delphinium diterpene

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alkaloids, 15-acetylcardiopentamine and cardiopentamine, are known to inhibit feeding of Spodoptera littoralis and Leptinotarsa decemlineata (Gonzalez-Coloma et al., 1998). Structure-activity studies point to C-13 and C-15 hydroxy substituents as essential features of the active molecules against S. littoralis, but C-13 hydroxy or C-15 acetate as responsible for feeding inhibition in L. decemlineata. This again implies that species-specific structural functionalities in a molecule determine their antifeedant activity.

MAYTANSINOIDS Powell et al. (1981, 1982) isolated a series of biologically active maytansinoids from ethanolic extract of Trewia nudiflora L. (Euphorbiaceae), of which trewiasine (113) is the most abundant. These compounds are unique in that they contain a 15-methoxyl group, thus far found only in maytansinoids from Trewia. Moreover, some of these also contain two fused macrocyclic rings, as in treflorine (114). O

H

C

N

O HO

C

CH

O CH

N

O

Cl

O

H3CO

N 18

Cl

O H3CO

O 1

3

H3CO

O

N

7 8

16 13

11

O

O

9 10

14

O

6

17

15

O

5 4

2

CH2

12

N

O

N

H3CO

OH OCH3

(113)

O

OH OCH3

(114)

In addition to the 19-membered ring characteristic structure, a 12-membered ring joining C-3 and the amide nitrogen at C-18 have been identified (Madrigal, 1985). These compounds inhibit feeding in the corn borer, Ostrinia nubilalis. The correlation among structures suggest that unique maytansinoid ring system, the hydroxyl at C-3 esterified with an amino acid, is essential for activity. A methoxyl group at C-15 seems to make little difference. However, more comprehensive study of such compounds is required to bring forth genuine conclusions.

ELLAGITANNINS Feeding-deterrent activity of ellagic acid (115), ellagitannin (116), gallic acid (117), geraniin (118), and several gallic acid derivatives towards various aphid species have revealed some structural basis for the activity (Jones and Klocke, 1987). Ellagitannins are characterized by the tanning property of forming hydrogen bonds between the phenolic hydroxyls of the tannin and the free amino and amide groups of proteins (McManus et al., 1983). This property has been hypothesized to be responsible for feeding deterrence in insects (Swain, 1979; Rhoades and Cates, 1976).

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Opender Koul OH HO

O

O

HO

O

O

O

COOH

OH

HO

OH

OH

OH

(116)

(117)

OH

(115)

OH

HO

OH

HO

HO

OH

HO

OH O

O

HO O

O

O HO

O

O

O O

OH

O O

OH HO O O

HO

OH OH

(118)

Ellagic acid, formed by oxidative coupling of two molecules of gallic acid, is tenfold more active as a feeding deterrent against Schizophis graminum than the gallic acid itself. A free ortho-hydroxyl group in gallic acid is important for deterrent activity, but esterfication of its carboxyl group with alkyl chains of increasing length results in increased activity. Thus there is considerable increase in activity from methyl gallate (119) and n-propyl gallate (120) to n-octyl gallate (121) and n-decyl gallate (122); the latter is as active as ellagic acid (Jones and Klocke, 1987). COOCH3

COOCH2CH2CH3

OH HO

HO OH

(119)

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OH OH

(120)

COO(CH2)7CH3

HO

OH OH

(121)

CH3(CH2)9OOC

OH

HO OH

(122)

Insect Antifeedants

67

ARISTOLOCHIC ACIDS The antifeedant activity of the metabolites of Aristolochia albida root extracts against S. litura larvae (Lajide et al., 1993a) is due to aristolochic acids (123). While 6-hydroxy aristolochic acid (128) is moderately active, aristolic acid (124), aristolactam (125), and aristolone (126) are inactive up to 0.1% treatment level. The synthetic analogues like methyl aristolochiate (127) and methyl-6-hydroxy aristolochiate (127) are lower in activity than parent compounds. Decarboxylation of parent acid also results in decreased activity. On comparing aristolochic acids, phenanthrene and 1,3-benzodioxole derivatives (Lajide et al., 1993b), aristolochic acids (123, 124) are most potent. Of the phenanthrene analogues, only phenanthridine (129) has a significant activity against S. litura larvae. O 2 O

3

O

4

COOH

1

COOH

O

O

NH NO2

10

O

O

9 5 8

6 7

OCH3

OCH3

OCH3

(123)

(124)

(125) COOCH3

O

COOH

O NO2

O

OCH3

R

R = H or R = OH (126)

NO2

O

O

(127)

OCH3

HO (128)

These observations reveal that the location of a –COOH group in close proximity to an –NO2 group is essential for activity, and the modification of the –COOH group results in reduced activity. In the series of aristolochic acid derivatives it is suggestive that more oxidized or unsaturated structures are efficient antifeedants. Such oxidized or unsaturated compounds like p-benzoquinones against p-hydroquinones (Chapter 7) are also known potential antifeedants (Norris, 1986). However, on analyzing the structures for specific structural features no single factor emerges predominantly among the compounds tested for antifeedant activity against S. litura larvae. Antifeedant activity seems to be strongly reduced upon modification of natural aristolochic acid structure, in particular the carboxylic acid group. The compounds that possess the ability to form reactive quinone intermediates such as (130, 131), as well as phenanthrene, are quite toxic, suggesting different mechanism of action and different molecular targets (Lajide et al., 1993b).

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Opender Koul O

N

(129)

NO2

O

(130)

O

H

O

NO2 (131)

The above discussion, therefore, clearly implies that there seems to be an inherent difficulty with respect to drawing meaningful generalized quantitative structural-activity relationship profile vis-à-vis the antifeedant activity. The basic explanation for this in part could be attributed to interspecific differences among bioassay organisms, i.e., use of insect growth stages, diversity of bioassays, and variations in the modes of application. Despite all these impediments, the above discussion has brought to the fore some specific relationships in basic skeletons that suggest that changes in substitution patterns, oxidation state, hydrophobicity, molecular connectivity, electrostatic potential, conformation, and distance geometry play a significant role in influencing the antifeedant activity of the compounds.

REFERENCES Baldoni, H.A., Enriz, R.D., Jauregui, E.A., and Csizmadia, I.G. (1996) A theoretical study on the conformations of azadirachtin. Theochem, 363, 167–178. Baldoni, H.A., Enriz, R.D., Jauregui, E.A., and Csizmadia, I.G. (1997) Theoretical study on the conformations of 3 tigloyl-azadirachtol and azadirachtin derivatives. Theochem, 391, 27–38. Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) Insect antifeedant activity of clerodane diterpenoids against larvae of Spodoptera littoralis (Boisd) (Lepidoptera). J. Chem. Ecol., 11, 1439–1445. Bentley, M.D., Leonard, D.E., Stoddard, W.F., and Zalkow, L.H. (1984a) Pyrrolizidine alkaloids as larval feeding deterrents for spruce budworm, Choristoneura fumiferana (Lepidoptera: Tortricidae). Ann. Entomol. Soc. Am., 77, 393–397. Bentley, M.D., Leonard, D.E., Reynolds, E.K., Leach, S., Beck, A.B., and Murakoshi, I. (1984b) Lupine alkaloids as larval feeding deterrents for spruce budworm, Choristoneura fumiferana (Lepidoptera: Tortricidae). Ann. Entomol. Soc. Am., 77, 398–400. Bentley, M.D., Leonard, D.E., and Bushway, R.J. (1984c) Solanum alkaloids as larval feeding deterrents for spruce budworm, Choristoneura fumiferana (Lepidoptera: Tortricidae). Ann. Entomol. Soc. Am., 77, 401–403. Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Structureactivity studies of modified citrus limonoids as antifeedants for Colorado potato beetle, Leptinotarsa decemlineata. Entomol. Exp. Appl., 49, 189–193. Bentley, M.D., Rajab, D.H.R., Herald, C.L., Polonsky, J., Schmidt, J.M., and Connolly, J.D. (1990) Limonoid model insect antifeedants. J. Agric. Food Chem., 38, 1400–1403. Blaney, W.M., Simmonds, M.S.J., Ley, S.V., and Katz, R.B. (1987) An electrophysiological and behavioural study of insect antifeedant properties of natural and synthetic drimane-related compounds. Physiol. Entomol., 12, 281–291. Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Antifeedant effects of azadirachtin and structurally related compounds on lepidopterous larvae. Entomol. Exp. Appl., 55, 149–160.

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Camps, F. and Coll, J. (1993) Insect allelochemicals from Ajuga plants. Phytochemistry, 32, 1361–1370. Champagne, D.E., Koul, O., Isman, M.B., Scudder, G.G.E., and Towers, G.H.N. (1992) Biological activity of limonoids from the rutales. Phytochemistry, 31, 377–394. Daniewski, W.M., Gumulka, M., Przesmycka, D., Ptaszynska, K., Bloszyk, E., and Drozdz, B. (1995) Sesqueterpenes of lactarius origin, antifeedant structure-activity relationships. Phytochemistry, 38, 1161–1168. Daniewski, W.M., Gumulka, M., Bloszyk, E., Jacobson, U., and Norin T. (1997) Isovellerol and new isolavtarane sesquiterpenes, their structure and antifeedant activity. Polish J. Chem., 71, 1254–1259. Dewar, M.J.S., Joebisch, E.G., Healey, E.F., and Stewart, J.J.P. (1985) AM1 a new general purpose quantum mechanical molecular model. J. Am. Chem. Soc., 107, 3902–3909. Dreyer, D.L., Jones, K.C., Jurd, L., and Campbell, B.C. (1987) Feeding deterrency of some 4-hydroxycoumarins and related compounds: relationships to host plant resistance of alfalfa towards pea aphid (Acyrthosiphon pisum). J. Chem Ecol., 13, 925–930. Enriz, R.D., Baldoni, H.A., Jauregui, E.A., Sosa, M.E., Tonn, C.E., and Giordano, O.S. (1994) Structure activity relationship of clerodane diterpenoids acting as antifeedant agents. J. Agric. Food Chem., 42, 2958–2963. Enriz, R.D., Baldoni, H.A., Zamora, M.A., Jauregui, E.A., Sosa, M.E., Tonn, C.E., Luco, J.M., and Gordaliza, M. (2000) Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azdirachtin. J. Agric. Food Chem., 48, 1384–1392. Evidente, A., Arrigoni, O., Luso, R., Calabrese, G., and Randazzo, G. (1986) Further experiments on structure-activity relationships among lycorine alkaloids. Phytochemistry, 25, 2739–2743. Gallardo, V.O., Tonn, C.E., Nieto, M., Morales, B.G., and Giordano, O.S. (1996) Bioactive neoclerodane diterpenoids towards Tenebrio molitor larvae from Teucrium nudicaule H. and Baccharis spicata (Lam) Bell. Natural Prod. Lett., 8, 189–197. Geuskens, R.B.M., Luteijn, J.M., and Schoonhoven, L.M. (1983) Antifeedant activity of some ajugarin derivatives in three lepidopterous species. Experientia, 39, 403-404. Giordano, O.S., Sosa, M.E., and Tonn, C.E. (2000) Biological activity of plant secondary metabolites towards Tenebrio molitor L. (Coleoptera: Tenebrionidae). Ann. Acad. Nacional Cienc. Exactas Fisic. Nat., 52, 163–181. Gols, G.J.Z., van Loon, J.J.A., and Messchendorp, L. (1996) Antifeedant and toxic effects of drimanes on Colorado potato beetle larvae. Entomol. Exp. Appl., 79, 69–76. Gonzalez, A.G., Jimenez, I.A., Ravelo, A.G., Coll, J., Gonzalez, J.A., and Lloria, J. (1997) Antifeedant activity of sesquiterpenes from celastraceae. Biochem. Syst. Ecol., 25, 513–519. Gonzalez-Coloma, A., Terrero, D., Perales, A., Escoubas, P., and Fraga, B.M. (1996) Insect antifeedant ryanodine diterpenes from Persea indica. J. Agric. Food Chem., 44, 296–300. Gonzalez-Coloma, A., Guadano, A., Gutierrez, C., Cabrera, R., Pena, E., Fuente, G., and Reina, M. (1998) Antifeedant Delphinium diterpenoid alkaloids. Structure-activity relationships. J. Agric. Food Chem., 46, 286–290. Gonzalez-Coloma, A., Valencia, F., Martin, N., Hoffmann, J.J., Hutter, L., Marco, J.A., and Reina, M. (2002) Silphinene sesquiterpenes as model insect antifeedants. J. Chem. Ecol., 28, 117–129. Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari, G.N. (1995) Structure-related insect antifeedant and growth regulating activities of some limonoids. J. Chem Ecol., 21, 1585–1600.

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Hansen, D.J., Cuomo, J., Khan, M., Gallagher, R.T., and Ellenberger, W.R. (1994) Advances in neem and azadirachtin chemistry and bioactivity. In Natural and Engineered Pest Management Agents, ACS Symp. Ser. 551, Am. Chem. Soc., Washington, D.C., pp. 103–129. Hein, D.F., Hummel, H.E., and Ley, S.V. (1999) Structure activity relationships in azadirachtin A derivatives: feeding activity and degree of efficiency tested on Epilachna varivestis larvae. Med. Fac. Landbou. Toegepaste Biol. Wetensch. Univ. Gent., 64, 197–204. Hosozawa, S., Kato, N., Munakata, K., and Chen, Y.L. (1974) Antifeeding active substances for insects in plants. Agric. Biol. Chem., 38, 1045–1048. Jones, K.C. and Klocke, J.A. (1987) Aphid feeding deterrency of ellagitannins, their phenolic hydrolysis products and related phenolic derivatives. Entomol Exp. Appl., 44, 229–234. Klocke, J.A., Arisawa, M., Handa, S.S., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1985) Growth inhibitory, insecticidal and antifeedant effects of some antileukemic and cytotoxic grass inoids on two species of agricultural pests. Experientia, 41, 379-382. Koul, O. (1982) Insect feeding deterrents in plants. Ind. Rev. Life Sci., 2, 97–125. Koul, O. (1992) Neem allelochemicals and insect control. In S.J.H. Rizvi and V. Rizvi (eds.), Allelopathy: Basic and Applied Aspects, Chapman & Hall, London, pp. 389–413. Koul, O. (1996) Neem research and development: Present and future scenario. In S.S. Handa and M.K. Koul (eds.), Supplement to Cultivation and Utilization of Medicinal Plants, PID, CSIR, New Delhi, pp. 583–611. Lajide, L., Escoubas, P., and Mizutani, J. (1993a) Antifeedant activity of metabolites of Aristolochia albida against the tobacco cutworm, Spodoptera litura. J. Agric. Food Chem., 41, 669–673. Lajide, L., Escoubas, P., and Mizutani, J. (1993b) Comparative effects of aristolochic acids, phenanthrene and 1,3-benzodioxole derivatives on the behaviour and survival of Spodoptera litura larvae. J. Agric. Food Chem., 41, 2426–2430. Lam, P.Y.-S. and Frazier, J.L. (1987) Model study on the mode of action of muzigadial antifeedant. Tetrahedron Lett., 28, 5477–5480. Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) Isoflavonoid feeding deterrents for Costelytra zealandica: Structure-activity relationships. J. Chem Ecol., 11, 1713–1735. Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) Antifeedant activity of quassinoids. J. Chem Ecol., 10, 1497–1507. Levin, D.A. (1976) Alkaloid bearing plants, an ecogeographical perspective. Am. Natr., 110, 261–284. Levinson, H.A. (1976) The defensive role of alkaloids in insects and plants. Experientia, 32, 408–411. Ley, S.V., Neuhaus, D., Simpkins, N.S., and Whittle, A.J. (1982) Synthesis of polyoxygenated trans-decalins as potential insect antifeedants. J. Chem Soc. Perkin I, 2157–2162. Ley, S.V., Denholm, A.A., and Wood, A. (1993) Chemistry of azadirachtin. Nat. Prod. Reports, 109–157. Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K. (1987) Insect antifeedant and growth inhibitory activity of forty six quassinoids on two species of agricultural pests. J. Nat. Prod., 50, 442-448. Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) Insect antifeedants from Atalantia racemosa. J. Agric. Food Chem., 37, 1435–1437. Luthria, D.L., Ramakrishnan, V., and Banerji, A. (1993) Insect antifeedant activity of furochromones: structure activity relationships. J. Nat. Prod., 56, 671–675.

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Madrigal, R.V., Zilkowski, B.W., and Smith, C.R. Jr. (1985) Structure/activity relationships among maytansinoids in their effect on the European corn borer, Ostrinia nubilalis (Hubner). J. Chem. Ecol., 11, 501–506. Malakov, P.Y., Papanov, G.Y., Rodriguez, B., de la Torre, M.C., Simmonds, M.S.J., Blaney, W.M., and Benova, I.M. (1994) Chemical transformation of some neo-clerodanes isolated from Teucrium: effect on the antifeedant activity. Phytochemistry, 37, 147–157. McManus, J., Lilley, J.H., and Haslam, E. (1983) Plant polyphenols and their association with proteins in plant resistance in insects. In P.A. Hedin (ed.), ACS Symp. Ser. 208, American Chemical Society, Washington, D.C., pp. 123–137. Miyasie, T., Kawasaki, H., Noro, T., Ueno, A., Fukushima, S., and Takemoto, T. (1981) Studies on the furanoid diterpenes from Teucrium japonicum Heutt. Chem. Pharm. Bull., 29, 3561–3564. Morimoto, M., Urakawa, M., Fujitaka, T., and Komai, K. (1999) Structure-activity relationship for the insect antifeedant activity of benzofuran derivatives. Biosci. Biotechnol. Biochem., 63, 840–846. Norris, D.M. (1986) Antifeeding compounds. In W.S. Bowers, W. Ebing, I.R. Fukuto, D. Martins, R. Weigler, and I. Yamamoto (eds.), Chemistry of Plant Protection, Sterol Biosynthesis, Inhibitors and Antifeeding Compounds, Springer Verlag, Secaucus, N.J., pp. 97–143. Odjo, A., Piart, J., Polonsky, J., and Roth, M. (1981) Etude de l’effet insecticide de deux quassinoids sur des larves de Locusta migratoria migratorioides R et F (Orthoptera, acrididae). C.R. Acad. Sci. Paris, 293, 241–244. Ohmura, W., Doi, S., Aoyama, M., and Ohara, S. (2000) Antifeedant activity of flavonoids and related compounds against the subterranean termite, Coptotermes formosanus Shiraki. J. Wood Sci., 46, 149–153. Pettit, G.R., Barton, D.H.R., Herald, C.L., Polonsky, J., Schmidt, J.M., and Connolly, J.D. (1983) Evaluation of limonoids against the murine P388 lymphocytic leukemia cell line. J. Nat. Prod., 46, 379–390. Picman, A.K. (1986) Biological activities of sesquiterpene lactones. Biochem. Syst. Ecol., 14, 255-281. Powell, R.G., Weisleder, D., and Smith, C.R. Jr. (1981) Novel maytansinoid tumor inhibitors from Trewia nudiflora: Trewiasine, dehydrotrewiasine and demethyltrewiasine. J. Org. Chem., 46, 4398–4403. Powell, R.G., Weisleder, D., Smith, C.R. Jr., Kozlowski, J., and Rohwedder, W.K. (1982) Treflorine, trenudine, and N-methyltrenudone: novel maytansinoid tumor-inhibitors containing two fused macrocyclic rings. J. Am. Chem. Soc., 104, 4929–4934. Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) C-5substituted antifeedant silphinene sesquiterpenes from Senecio palmensis. J. Nat. Prod., 65, 448–453. Rembold, H. (1989) Isomeric azadirachtins and their mode of action. In M. Jacobson (ed.), Focus on Phytochemical Pesticides, Vol. I (The Neem Tree), CRC Press, Boca Raton, Fla., pp. 47–67. Rhoades, D.F. and Cates, R.G. (1976) Towards a general theory of plant antiherbivore chemistry. Rec. Adv. Phytochem., 10, 168–213. Rodriguez, B., de la Torre, M.C., Rodriguez, B., Bruno, M., Piozzi, F., Savona, G., Simmonds, M.S.J., Blaney, W.M., and Perales, A. (1993) Neo-clerodane insect antifeedants from Scutellaria galericulata. Phytochemistry, 33, 309–315.

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Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Grindelane diterpenoid acids from Grindelia humilis, feeding deterrency of diterpenoid acids towards aphids. Phytochemistry, 20, 2249–2255. Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) Citrus limonoids and their semisynthetic derivatives as antifeedant agents against Spodoptera frugiperda larvae. A structure-activity relationship study. J. Agric. Food Chem., 50, 6766–6774. Russel, G.B., Sutherland, O.R.W., Hutchins, R.F.N., and Christmas, P.E. (1978) Vestitol: A phytoalexin with insect feeding deterrent activity. J. Chem. Ecol., 4, 571–579. Schuh, B.A., and Benjamin, D.M. (1984) The chemical feeding ecology of Neodiprion dubious Schedl., N. rugifrons Midd. and N. leconti (Ritch) on Jack Pine (Pinus barksiana Lamb.). J. Chem. Ecol., 10, 1071–1079. Suresh, G., Gopalakrishnan, G., Wesley, S.D., Pradeep Singh, N.D., Malathi, R., and Rajan, S.S. (2002) Insect antifeedant activity of tetranortriterpenoids from the Rutales. A perusal of structure relations. J. Agric. Food Chem., 50, 4484–4490. Swain, T. (1979) Tannins and lignins. In G.A. Rosenthal and D.H. Janzen (eds.), Herbivores: Their Interaction with Secondary Plant Metabolites, Academic Press, New York, pp. 657–682. Toda, T., Tokunaja, T., Ouchida, T., Shiroya, K., and Nakamoto, T. (1958) Chemotherapeutic agents I. The antibacterial activity of pyrone derivatives in vitro. Chemotherapy (Tokyo), 6, 91–95. Urones, J.G., Basabe, P., Lithogow, A.M., Marcos, I.S., Jimenez, A., Diez, D., Gomez, A., White, A.J.P., Williams, D.J., Simmonds, M.S.J., and Blaney, W.M. (1995) New antifeedant neo-clerodane triol. Semisynthesis and antifeedant activity of neo-clerodane diterpenoids. Tetrahedron, 51, 2117–2128. Van Beek, T.A. and deGroot, A.C. (1986) Terpenoid antifeedants I. An overview of terpenoid antifeedants of natural origin. Recueil des Trav. Chimiq. des Pays-Bas, 105, 513–527. Wagner, M.R., Benjamin, D.M., Clancy, K.M., and Schuh, B.A. (1983) Influence of diterpene resin acids on feeding and growth of larch sawfly, Pristophora erichsonii (Hartig). J. Chem. Ecol., 9, 119–127. Yamasaki, R.B. and Klocke, J.A. (1987) Structure-bioactivity relationship of azadirachtin, a potential insect control agent. J. Agric. Food Chem., 35, 467–471. Yamasaki, R.B. and Klocke, J.A. (1989) Structure-bioactivity relationship of salannin as an antifeedant against the Colorado potato beetle (Leptinotarsa decemlineata). J. Agric. Food Chem., 37, 1118–1124. Yano, K. (1986) Relationship between chemical structure of phenylalkynes and their antifeedant activity for larvae of a cabbage butterfly. Insect Biochem., 16, 717–719. Yano, K. (1987) Minor components from growing buds of Artemisia capillaris that act as insect antifeedants. J. Agric. Food Chem., 35, 889–891. Yano, K. (1998) Relationship between chemical structure of antifeedants from Artemisia capillaris buds and their antifeedant activity toward Pieris rapae crucivora larvae. Recent Res. Develop. Agric. Biol. Chem., 2, 293–305. Yano, K. and Kamimura, H. (1993) Antifeedant activity toward larvae of Pieris rapae crucivora of phenol ethers related to methyleugenol isolated from Artemisia capillaris. Biosci. Biotech. Biochem., 57, 129–130. Yano, K. and Tanaka, N. (1995) Antifeedant activity toward larvae of Pieris rapae crucivora of aromatic carbonyl compounds related to capillin isolated from Artemisia capillaris. Biosci. Biotech. Biochem., 59, 1130–1132.

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5 COMMERCIALIZATION The present state-of-the-art situation of insect antifeedants, from a commercial point of view, indicates that such chemicals have not really made headway on a large scale because of the lack of technology to produce them in sufficient quantity and the time-consuming and laborintensive procedures to prepare them. Therefore, in spite of the wide recognition that many allelochemicals possess potential insect control properties, only a handful are in use in some parts of the world. At best, botanical insecticides constitute 1% of the world insecticide market, but annual sales growth in the range of 10 to 15% is entirely possible. The impact, however, in the range of 25% market share within 5 years, has been envisaged in the homeand-garden sector (Isman, 1997). Among more than 800 insect antifeedant compounds known today (Chapter 7) only the compounds from neem, Azadirachta indica, have shown commercial potential; quite a few products are in the market that have met regulatory requirements and received firm or provisional registrations. The overall picture makes one surmise that commercial neem products have gained greater significance in the Indian subcontinent, where there are commercially marketed products for virtually all types of usage. Many products occupy a large share of the market, e.g., neem-based soap, toothpaste, pesticides, and fertilizers (Koul, 1996). In all other countries, commercial neem products count for only a modest share of the market. Throughout the world, in those countries where neem trees are grown, the prices for dried seeds are between U.S. $0.10 and $2.00 per kg. To effectively control most pests, one hectare of crops must be treated once with between 20 and 60 g of the main active ingredient, azadirachtin. Thus, given the fact that there are approximately 2 g of azadirachtin per kg of seeds on an average, somewhere between 10 and 30 kg of neem seeds are needed in all. This means that the seed costs alone for the single treatment of one hectare of crops are between U.S. $1.00 and U.S. $60.00, although in most countries they are somewhere in the narrower range between U.S. $5.00 and U.S. $20.00 (Status Report on Global Neem Usage, 2000).

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COMMERCIAL NEEM INSECTICIDE PRODUCTS BY COUNTRIES or REGIONS, IN % OF THE RESPONSES FROM THE GIVEN REGIONS Asia Africa Caribbean/Latin America Industrialized Countries

71% 38% 50% 100%

An additional factor when calculating the cost of manufacturing formulated, neem-based pesticides are the costs of extraction, which means that production of this kind is most probably only profitable in those countries with low seed prices. However, these costs decrease in relation to the quality of pesticides produced. For instance, according to the estimates of Neem Foundation (2003), environmental service rendered by neem tree at $10 per month, would yield a value of U.S. $24,000 to $36,000 in its 200- to 300-year lifetime. Further, the alternative uses in organic agriculture (like fertilizer) and medicinal products give commercialized neem huge economic potential. However, it is to be seen how exclusive rights to produce and export botanical biopesticides are going to be handled globally; this has tremendous legal implications. So it is to be seen what happens in 2005 when the real effects of TRIPS (Trade Related Intellectual Property Rights) will be felt. When assessing the economic efficiency of neem, it is important not to forget that other secondary products can be obtained from the tree, which not only constitute additional biological activity potential but also their own marketing right. Present status of commercial neem-based pesticides on the market and their respective registration status is given in Table 5.1. However, apart from neem products, there are few actual demonstrations of antifeedant efficacy in the field. Application of polygodial or methyl salicylate at the IARC-Rothamsted showed that aphid populations are reduced with concomitant increases in yields of winter wheat, in one case comparable to that achieved with the pyrethroid insecticide cypermethrin (Pickett et al., 1997). Similarly, toosendanin, an antifeedant limonoid from the bark of the trees Melia toosendan and M. azedarach (Meliaceae), has been subjected to considerable research as a botanical pesticide (Chiu, 1989, Zhang et al., 1992, Chen et al., 1995, Koul et al., 2002). Vertebrate selectivity of this compound is very favorable (LD50 mice = 10 g/kg) (Isman, 1994). Production of a botanical insecticide based on toosendanin, using a refined bark extract containing approximately 3% toosendanin (racemic mixture) as the active ingredient, has recently begun in P.R. China (Zhang et al., 1992). This could become a potential commercial product worldwide, as formulations based on the technical concentrate are under evaluation in Canada to assess its potential against pests of agriculture and forestry in North America. Triphenyltin acetate, used as a fungicide, algicide, and molluscicide, had shown potential for use as a crop protectant against lepidopteran pests through antifeedant action, but this pesticide has fallen from favor owing to environmental concerns (Perry et al., 1998). At this stage it is imperative to know that, in spite of the wide recognition that many plants possess antifeedant compounds, only neem allelochemicals have made some impact. The reason is that neem allelochemicals apparently have admirably met most of the criteria for useful pest control agent as compared to other isolated compounds from various plants. Still, the commercialization of neem products for use in North America and Europe has taken many years, incurring the cost in millions of U.S. dollars. Obviously, in addition to being an efficacious and safe product, there are apparently other considerations required to be satisfied in order to compete with conventional pesticides. In fact, the commercialization of new feeding deterrents is hindered by three basic factors:

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Limitations in natural resources Quality control and standardization Regulatory constraints

From a commercial point of view it is very essential to have an abundance of starting material, which can meet market demand on a consistent basis. The main aim is to obtain sufficient biomass for extraction or subsequent isolation of pure active ingredients. Therefore, it is very essential to get such material through cultivation or plantation of such trees, as has been established in the case of neem in Australia, Brazil, Kenya, Philippines, and so on. It is very useful to have a source of biomass in a convenient fashion such as seeds, because it is easy to collect and process them. This has been achieved in the case of neem (Koul, 1996), citrus fruit seeds (Klocke and Kubo, 1982), and Annona seeds (McLaughlin et al., 1997). Tissue culture technique is a useful procedure for obtaining bioactive products on a large scale. There are a number of plants that have been subjected to this technique for obtaining bioactive materials (Koul, 1996; Koul and Wahab, 2004) but only the substantial success in terms of feeding deterrents is azadirachtin, where cell suspension cultures have produced azadirachtin in good yields (Holowach et al., 1994). The second important hindrance is that of standardization and quality control. Standardization of active ingredients in natural products has several constraints, particularly: • • •

Ecotypical differences for the same species that influence active ingredients Activity due to complex mixtures Synergistic action of co-occurring toxins within a natural mixture

These factors affect the standardization of a material considerably and are well evidenced in many compounds like pyrethrins, rotenones, isoflavonoids, azadirachtins, and toosendanins (Isman, 1997). However, complex mixtures could be advantageous, too, from pest resistance and behavioral desensitization points of view. Regulatory requirements for active ingredient specifications are a must, but very difficult to achieve in case of mixtures. That is why in neem-based formulations, quantification of azadirachtin A and azadirachtin B is a minimum requirement under regulatory measures, although other active ingredients such as salannin and others (Koul, 1992) are also the components of such formulations. Regulatory requirements are essential for the commercialization of a product and thus applicable to feeding deterrents as well. Neem-based products have been successful to some extent in obtaining registration for a number of formulations in various parts of the world (Table 5.1). However, the registration of a new feeding deterrent is a tough task because most of the regulatory parameters are based specifically around synthetic chemicals. Some organizations ask for toxicological data for every characterized active component, which will cost millions of dollars. However, some solace comes from the actions taken in Canada by the Pest Management Regulatory Agency, which approved an experimental use permit allowing the aerial application of neem to control forest-defoliating sawflies based on HPLC analysis of the neem concentrate (in which the major ten limonoids, accounting for 90% of the UV-visible material, were identified and quantified) (Isman, 1997). In North America, this “reduced risk” pesticide category identified through product identicality has been emphasized every time it is manufactured. Because the large multinationals have no serious interest in the development of nonpersistent nature-based biological pesticides (like feeding deterrents), commercialization of such products is mainly taken by small manufacturers. In fact in India to achieve this goal, provisional registrations have been given to manufacturers, and the products are being sold

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TABLE 5.1 Commercial Neem-Based Pesticides in Various Countries Country Australia Austria Benin Brazil Canada China Colombia Costa Rica Cuba Denmark Dominican Republic Dutch Antilles Ecuador Egypt Fiji Germany Ghana India Indonesia Israel Italy Kenya Mauritius Myanmar Nepal Nicaragua Niger Pakistan Saudi Arabia Senegal Spain Sri Lanka Sweden Switzerland Thailand Togo Uganda U.S. Venezuela

Number of products 2 3 1 Unclear 1 1 3 2 3 2 3 2 4 5 1 5 3 ~100 1 3 2 8 1 3 1 4 2 2 4 2 2 2 2 3 3 2 2 5 3

Status About to be registered Registration for eco-cropping Unclear Imported from Germany Temporary registration for forest pests Provisional registration Unclear Registered Registered Under registration Registered Registered Unclear, imported from U.S. Registered, imported from Germany and Sweden Registered Registered and offered as raw material Provisional registration, imported from India, U.S. Limited number of products registered Registration pending Registered and imported from U.S. Registered products from India and Germany Variable registration status, imported from India and U.S. Registered and imported from India Registered Registered and imported from India Registered About to be registered Unclear Registered, imported from U.S. Provisional registration Registered formulated products Registered products from India, local unclear Registered Registered for fruit crops, offered as raw material Registered Registration not required Registered, imported from Kenya Registered Unclear, imported from U.S.

Modified from Status Report on Global Neem Usage (2000), GTZ, Germany.

in the market. However, it becomes imperative for producers to fulfill the requirements within the stipulated time frame, as provided by the regulatory authorities. I believe that Western countries should adopt this policy, if biological pesticides are to make any impact in the near future in the conventional insecticide market. Neem has already provided a modern paradigm for the development of biopesticides, and others have to follow the direction. Another operational problem specific to antifeedants is the potential for insects to rapidly desensitize (habituate) to a feeding deterrent. Several investigations have demonstrated that individual (naïve) insects initially deterred by an antifeedant become increasingly tolerant

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upon repeated exposures or through continuous exposure. Under no-choice conditions, feeding by tobacco cutworm larvae on cabbage disks treated with azadirachtin was initially deterred by 90%, but with continuous exposure, the response had waned by more than one half within 5 hours (Bomford and Isman, 1996). With another insect antifeedant, toosendanin from Melia toosendan (Chiu and Zhang, 1987) and Melia azedarach (Koul et al., 2002), feeding deterrence was completely abolished at 4.5 hours (Isman, 2002). This implies that a crop treated with an antifeedant might only enjoy protection from a pest for a few hours before the insect becomes habituated and can then feed with impunity. This also shows that caterpillars can become habituated to a variety of plant secondary metabolites, and importantly, they can become cross-habituated (Isman, 2002). However, use of mixtures could help in mitigating the habituation process in insects, by presenting mixtures of antifeedants. Recent studies have shown that mixtures of compounds play a significant role in the activity within a plant system (Koul et al., 2003). It is also well documented that Spodoptera litura larvae could habituate to pure azadirachtin, but less so to a neem extract containing the same absolute amount of azadirachtin (Bomford and Isman, 1996). In conclusion, given the aforementioned limitations to the use of insect antifeedants (differences in response between pest species, potential desensitization of pests, and rapid environmental degradation), it is most unlikely that an antifeedant will emerge with sufficient field efficacy to act as a standalone crop protectant. According to Isman (2002), assuming that there are insect antifeedants (i) with minimal bioactivity in mammals and other nontarget organisms, and (ii) are available on a commercial scale, there are likely specific crop–pest combinations where an antifeedant can play a significant role as part of an integrated pest management system. Whether the market(s) for such a specific protectant can justify the costs of development remains to be seen. Ongoing research into insect sensory systems, neuropharmacology, and organic chemistry may ultimately mitigate the limitations to antifeedants observed at present and lead to a suite of new crop protectants based on deterrence of insect feeding and oviposition.

REFERENCES Bomford, M.K. and Isman, M.B. (1996) Desensitization of fifth instar Spodoptera litura to azadirachtin and neem. Entomol. Exp. Appl., 81, 301–313. Chen, W., Isman, M.B., and Chiu, S.-F. (1995) Antifeedant and growth inhibitory effects of the limonoid toosendanin and Melia toosendan extracts on the variegated cutworm, Peridroma saucia (Lep., Noctuidae). J. Appl. Ent., 119, 367–370. Chiu, S.-F. (1989) Recent advances in research on botanical insecticides in China. In J.T. Arnason, B.J.R. Philogene, and P. Morand (eds.), Insecticides of Plant Origin, ACS Symp. Ser. 387, Am. Chem. Soc., Washington, D.C., pp. 69–77. Chiu, S.-F. and Zhang, X. (1987) A critical review of toosendanin, a novel insecticide isolated from Melia toosendan Sieb. et Zucc. (Meliaceae). J. South China Agric. Univ., 8, 57–67. Holowach, K., Lorraine, P., Birman, I., and Patterson, D.R. (1994) A method for producing azadirachtin. Eur. Patent EP 605139, 21 pp. Isman, M.B. (1994) Botanical insecticides. Pestic. Outlook, 5, 26–31. Isman, M.B. (1997) Neem and other botanical insecticides: Barriers for commercialization. Phytoparasitica, 25, 339–344. Isman, M.B. (2002) Insect antifeedants. Pestic. Outlook, 13, 152–157. Klocke, J.A. and Kubo, I. (1982) Citrus limonoid by-products as insect control agents. Entomol. Exp. Appl., 32, 299–301.

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Koul, O. (1992) Neem allelochemical and insect control. In S.J.H. Rizvi and V. Rizvi (eds.), Allelopathy: Basic and Applied Aspects, Chapman & Hall, London, pp. 389–413. Koul, O. (1996) Natural product leads as anti-insect compounds: Prospects for biotechnology. In T.N. Ananthakrishnan (ed.), Biotechnological Perspectives in Chemical Ecology of Insects, Oxford & IBH Publishing Co. Pvt. Ltd., New Delhi, pp. 15–27. Koul, O. and Wahab, S. (2004) Neem: Today and in the New Millennium, Kluwer Academic Publishers, The Netherlands. Koul, O., Multani, J.S., Singh, G., and Wahab, S. (2002) Bioefficacy of toosendanin from Melia dubia (syn. M. azedarach) against gram pod-borer, Helicoverpa armigera (Hubner). Curr. Sci., 83, 1387–1391. Koul, O., Multani, J.S., Singh G., Daniewski, W.M., and Berlozecki, S. (2003) 6β-Hydroxygedunin from Azadirachta indica, its potentiation effects with some non-azadirachtin limonoids in neem against lepidopteran larvae. J. Agric. Food Chem., 51, 2937–2942. McLaughlin, J.L., Zeng, L., Oberlies, N.H., Alfonso, D., Jhonson, H.A., and Cummings, B.A. (1997) Annonaceous acetogenins as new pesticides: recent progress. In P.A. Hedin, R.M. Hollingworth, E.P. Masler, J. Miyamoto, and D.G. Thompson (eds.), Phytochemicals for Pest Control, ACS Symp. Ser. 658, Am. Chem. Soc., Washington, D.C., pp. 117–133. Neem Foundation (2003) www.neemfoundation.org. Perry, A.S., Yamamoto, I., Ishaaya, I., and Perry, R.Y. (1998) Insecticides in Agriculture and Environment. Springer Verlag, Berlin. Pickett, J.A., Wadhams, L.J., and Woodcock, C.M. (1997) Developing sustainable pest control from chemical ecology. Agric. Ecosyst. Environ., 64, 149–156. Status report on global neem usage (2000) Deutsche Gesellschaft fur Technische Zusammenarbeit (GTZ), Eschborn, Germany. Zhang, X., Wang, X.-L., and Chiu, S.-F. (1992) Studies on the bioactivities and applications of Chinese botanical insecticide: toosendanin. XIX Intl. Congr. Entomol., Beijing, abstracts, p. 570.

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6 PRACTICAL APPLICATIONS AND CONCLUSIONS The use of antifeedants in pest-management programs has enormous intuitive appeal. They satisfy the need to protect specific crops while avoiding damage to non-target organisms, so that potential value is very great. In fact, insect damage to plants results from feeding or from transmission of pathogens during feeding; therefore, the chemicals that reduce pest injury by rendering plants unattractive or unpalatable can be considered as potential substitutes for conventional insecticides. Programs have been launched in several countries for developing feeding deterrents known to occur naturally in plants (Saxena, 1987); killing and destruction of pests is not always necessary if using antifeedants can incapacitate them. According to Jermy (1983), research on the practical use of antifeedants of plant origin should consider: • • • • • •

The wide capability of the chemosensory mechanism governing feeding behavior in polyphagous insects The complexity of the inhibitory biochemical profile of plants deterring a given insect species The difference of these profiles in relation to different insect species The variation in feeding behavior of different populations of the same insect species The changes of plant constituents in time and space (polychemism) The problem of formulation of antifeedants for plant protection purposes

The question, therefore, is, What have we achieved in terms of research in this relatively new and promising field? When we look at the role of antifeedants in pest management

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strategies, the answer is quite deplorable that only a few allelochemicals have been subjected to large-scale field experimentation to prove the practicability of such approaches. However, the outcome of many studies is that there is increasing interest in the use of insect antifeedants against agricultural pests, but their effects are often short lived, either because the compounds themselves are non-persistent or because, after a period of starvation, insects habituate to such materials. This aspect has been very well demonstrated in neem and azadirachtin studies. For instance, in a very recent study the deterrence of azadirachtin, in its pure form and as a constituent of neem seed extract, to fifth instar Spodoptera litura larvae has been measured. The effects of hunger and habituation on desensitization have been demonstrated. After repeated exposure, larvae become desensitized to pure azadirachtin in both choice and nochoice tests. Hunger was responsible for approximately one third of the desensitization response (Bomford and Isman, 1996). This means that new strategies have to be devised that allow for possible changes in insect behavior. The future for the use of antifeedants in crop protection lies in their integration into pest management programs, in combination with other agents of control. In a study the insect growth regulator teflubenzuron, which acts by the oral route and is relatively inactive as an antifeedant against mustard beetles or diamond back moth larvae, has been used in a similar program. Two methods of combining the use of teflubenzuron with insect antifeedant have been studied (Griffiths et al., 1991). The strategy of applying the antifeedant and growth inhibitor together relies on stopping the overshoot in feeding that occurs when the insects are poisoned by teflubenzuron. The insect needs to eat < 1% of the leaf disk to acquire a toxic dose but, in the absence of an antifeedant, it eats > 40% even at the highest doses, during the lag phase that occurs between treatment and effect. In laboratory conditions, the combination of antifeedant with teflubenzuron decreased feeding damage by Plutella xylostella and Phaedon cochlearae without diminishing the toxic effect (Griffiths et al., 1991). In the alternative strategy teflubenzuron and antifeedant were applied separately. Treatment of the growing tips of mustard plants with antifeedant forced insects down the plant to the lower leaves, where they were killed by diflubenzuron. Manipulation of insect populations in this way now forms part of various insect control studies, such as the stimulo-deterrent diversionary cropping strategy (Miller and Cowles, 1990) and the push pull strategies described by Pyke et al. (1987). In terms of toxicological aspects the most important aspect of practical application is mammalian toxicity. It is theoretically possible to find antifeedants lacking any harmful effects to humans, such as Margosan-O (Larson, 1987), mint compounds, and quinine (Jermy, 1990). Unfortunately, for the known plant antifeedants, reports regarding mammalian toxicity are mostly lacking (see Chapter 7). This may be due to the belief that secondary plant compounds are of natural origin and highly degradable, and therefore pose lesser environmental hazards than synthetic chemicals. Of course, this does not eliminate the safety procedures required for new product development. Persistence is another prerequisite for practical application. The persistence of metalorganic antifeedants such as copper and tin fungicides is well known but persistence is largely unknown for plant allelochemicals. Again detailed studies are known for neem products. Stokes and Redfern (1982) have shown azadirachtin losing its antifeedant activity by more than 50% in 7 days when exposed to sunlight. Ermel et al. (1987) showed that azadirachtin was degraded to 50% in 12 days in greenhouse. Saxena (1987) lost the activity of neem oil in 4 days in rice plants. Half-life of azadirachtin sprayed on conifer and deciduous foliage was only 20 hours (Isman, 1997); however, exposure of neem insecticides on glass plate to

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light at one-quarter of intensity of sunlight (at the latitude of southern Canada) resulted in a half-life for azadirachtin of 5 days (Sunderam and Curry, 1996). The half-life of azadirachtin in normal soil at 25°C is 20 days, but is 31.5 days in autoclaved soil, indicating that organisms are involved in its degradation (Stark and Walter, 1995). The persistence of antifeedants, however, is affected by behavioral desensitization (Bomford and Isman, 1996); a generalized model for quantifying the behavioral desensitization using lepidopteran larvae has been developed (Raffa and Frazier, 1988). Along with the persistence, of course, it is important that antifeedants do not have phytotoxic effects on the plants to be protected. Few secondary compounds have been studied for their phytotoxicity, which indicates little or no phytotoxicity (Schoonhoven, 1982), but it may be expected that several feeding deterrents will be toxic because of their known allelopathic function. Systemic action of antifeedants is another useful aspect of their practical application. On one hand it will exert uniform distribution within the plant, and on the other it will counterbalance the phagostimulatory effects of plant surface chemicals (Chapman and Bernays, 1989). The systemic action of neem extracts is well documented (Gill and Lewis, 1971; Abdul Kareem et al., 1989; Osman and Port, 1990; Koul and Shankar, 1995). Thus gradual release of neem compounds from neem seed powder incorporated in the soil and their gradual translocation by plant gives neem a considerable persistence as a control agent. Similarly extracts of Amora ruhituka and A. squamosa (Islam, 1987) have also been shown to have systemic action. Coumarin is transported in grass leaves and thus unpalatable to Chorthippus parallelus, and sinigrin is absorbed from water solution and transported to stems and leaves of various plant species. However, if a promising antifeedant is to be established for insect control, further investigations into systemic studies are unavoidable. Antifeedant study is also dependent on monocomponent systems, testing single compounds, which could sometimes be totally artificial. In fact, additive effects of antifeedant compounds have been demonstrated against Locusta migratoria (Adams and Bernays, 1978). In several cases, a plant containing a combination of antifeedants acts in unison to protect itself from insect attack. Therefore, a mixture of compounds is likely to be more effective as an antifeedant and accordingly quite useful in response to great interspecific variations among insects. De facto, neem preparations have clearly shown this (Koul et al., 2003a, 2003b), and Jermy (1990) rightfully suggested that comparative trials with simple antifeedant compounds and with their combinations, especially under field conditions, are indispensable. Lack of resistance is also very useful for practical application of antifeedants, as it is unlikely that oligophagous insects could develop general resistance to such deterrents, because this would result in rapid change of their host-plant range, which is determined mainly by the occurrence of such chemicals in the non-host plants. Different molecular structures of possible antifeedant compounds could be another advantage. However, permanent application of a feeding deterrent may result in the development of resistance. This has been indicated in the studies of selection of resistance to azadirachtin in the green peach aphid, Myzus persicae (Feng and Isman, 1995). When two lines of this aphid were treated repeatedly with pure azadirachtin, after 40 generations the AZA-selected line developed ninefold resistance to AZA compared to a non-selected control line. Interestingly this type of resistance did not develop in extract-treated (with same amount of AZA) insects. These results suggest that a blend of active constituents might diffuse the selection process, mitigating the development of resistance compared to that expected with a single active ingredient. This also supports the earlier-mentioned contention that combination mixtures of antifeedants could be more effective than individual compounds.

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CONCLUSIONS Most of the research to date on the antifeedant compounds has been motivated by the desire to find useful compounds for specific agricultural applications. As a result bioassay designs and choice bioassays have varied considerably. Many of the various types of structures of antifeedants appear to be highly oxidized, with a variety of functional groups present in the molecules. From the high level of activity of more than 800 antifeedant compounds, only azadirachtin or neem preparations have made a real impact. Accordingly limited progress has been made in this field, particularly from a commercial point of view. Several aspects deserve more attention in order to implement use of antifeedants in integrated pest management programs. • • • • • •

•

•

Bioassays used should have close conformity with the field conditions. Extensive structure-bioactivity relationships combined with behavioral and electrophysiological studies are required. Systemic action of antifeedants should be stressed, which could be highly useful in pest control. Formulation aspects should be used strictly in laboratory conditions, so that there is less variation from lab to field. Modes of action and influence on insect behavior and ecological systems should be monitored closely. Phytochemistry studies should be continued and new or known antifeedants should be isolated and identified with the right bioassay and phytotoxicity evaluation. In fact, a combination of co-occurring molecules should be given priority for better results. An alternative approach could be the introduction of antifeedant in the plant itself, either by breeding experiments or by genetic manipulation. However, one has to keep fingers crossed because such approaches could prop up new problems of toxicity and resistance. Use of antifeedants with a synergist deserves attention.

On the whole, for a characteristic and ideal antifeedant for insect control, van Beck and de Groot (1986) proposed a list of conditions that seem to be very appropriate for obtaining a suitable insect feeding deterrent: • • • • • • • • • • • • •

They They They They They They They They They They They They They

should should should should should should should should should should should should should

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be non-toxic to the ecosystem. not be phytotoxic. be as far as possible a generalistic antifeedant. be preferably also toxic against the same insect. be active at a very low concentration. be persistent when applied to crops. yield no toxic or bad-tasting metabolites. have systemic action. be easily applied. be low cost and supplied without disruptions. be compatible with other forms of pest management. not lead to habituation or resistance easily. be stable during storage, but biodegradable to some extent in field.

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83

REFERENCES Abdul Kareem, A., Saxena, R.C., Boncodin, M.E.M., Krishnasamy, V., and Seshu, D.V. (1989) Neem and seed treatment for rice before sowing. Effect on two homopteran insects and seedling vigour. J. Econ. Entomol., 82, 1219–1223. Adams, C.A. and Bernays, E.A. (1978) The effect of combination of deterrents on the feeding behaviour of Locusta migratoria. Entomol. Exp. Appl., 23, 107–109. Bomford, M.K. and Isman, M.B. (1996) Desensitization of fifth instar Spodoptera litura to azadirachtin and neem. Entomol. Exp. Appl. 81, 307–313. Chapman, R.F. and Bernays, E.A. (1989) Insect behaviour at the leaf surface and learning as aspects of host plant relation. Experientia, 45, 215–222. Ermel, K., Pahlich, E., and Schmutterer, H. (1987) Azadirachtin content of neem kernels from different geographical locations and its dependence on temperature, relative humidity and light. In H. Schmutterer and K.R.S. Ascher (eds.), Natural Pesticides from Neem Tree and Other Tropical Plants, GTZ, Eschborn, pp. 171–184. Feng, R. and Isman, M.B. (1995) Selection for resistance to azadirachtin in the green peach aphid, Myzus persicae. Experientia, 51, 831–833. Gill, J.S. and Lewis, C.T. (1971) Systemic action of an insect feeding deterrent. Nature London, 232, 402–403. Griffiths, D.C., Maniar, S.P., Merritt, L.A., Mudd, A., Pickett, J.A., Pye, B.J., Smart, L.E., and Wadhams, L.J. (1991) Laboratory evaluation of pest management strategies combining antifeedants with insect growth regulator insecticides. Crop Protection, 10, 145–151. Islam, B.N. (1987) Use of some extracts from Meliaceae and Annonaceae for control of rice hispa, Dicladispa armigera and pulse beetle, Callosobruchus chinensis. In H. Schumutterer and K.R.S. Ascher (eds.), Natural Pesticides from Neem Tree and Other Tropical Plants, GTZ, Eschborn, pp. 217–242. Isman, M.B. (1997) Neem insecticides. Pesticide Outlook, 8, 32–38. Jermy, T. (1983) Multiplicity of insect antifeedants in plants. In D.L. Whitehead and W.S. Bowers (eds.), Natural Products for Innovative Pest Management, Pergamon Press, New York, pp. 223–236. Jermy, T. (1990) Prospects of antifeedant approach to pest control: A critical review. J. Chem. Ecol., 16, 3151–3161. Koul, O. and Shankar, J.S. (1995) Systemic uptake of azadirachtin into Ricinus communis: Effect on larvae of Spodoptera litura. Ind. J. Expt. Biol., 33, 865–867. Koul, O., Multani, J.S., Singh G., Daniewski, W.M., and Berlozecki, S. (2003) 6β-Hydroxygedunin from Azadirachta indica, its potentiation effects with some non-azadirachtin limonoids in neem against lepidopteran larvae. J. Agric. Food Chem., 51, 2937–2942. Koul, O., Multani, J.S., Goomber S., Daniewski, W.M., and Berlozecki, S. (2004) Activity of some non-azadirachtin limonoids from Azadirachta indica against lepidopteran larvae. Aust. J. Entomol. 43, 189–195. Larson, R.O. (1987) Development of Margosan-O, a pesticide from neem seed. In H. Schmutterer and K.R.S. Ascher (eds.), Natural Pesticides from Neem Tree and Other Tropical Plants, GTZ, Eschborn, pp. 243–250. Miller, J.R. and Cowles, R.S. (1990) Stimulo-deterrent diversionary cropping: a concept and its possible application to onion maggot control. J. Chem. Ecol., 16, 3197–3212. Osman, M.Z. and Port, G.R. (1990) Systemic action of neem seed substances against Pieris brassicae. Entomol. Exp. Appl., 54, 297–300.

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Pyke, B., Rice, M., Sabine, B., and Zalucki, M.S. (1987) The push-pull strategy: behavioural control of Heliothis. Aust. Cotton Grower, 7–9. Raffa, K.F. and Frazier, J.L. (1988) A generalised model for quantifying behavioural desensitization to antifeedants. Entomol. Exp. Appl., 46, 93–100. Saxena, R.C. (1987) Antifeedants in tropical pest management. Insect Sci. Applic., 8, 731–736. Schoonhoven, L.M. (1982) Biological aspects of antifeedants. Entomol. Exp. Appl., 31, 57–69. Stark, J.D. and Walter, J.F. (1995) Persistence of azadirachtin A & B in soil: effect of temperature and microbial activity. J. Environ. Sci. Health, 30B, 685–698. Stokes, J.B. and Redfern, R.E. (1982) Effect of sunlight on azadirachtin: Antifeeding potency. J. Environ. Sci. Health, 17A, 57–65. Sundaram, K.M.S. and Curry, J. (1996) Effect of some UV light absorbers on the photosensitization of azadirachtin, a neem-based biopesticide. Chemosphere, 32, 649–659. Van Beek, T.A. and de Groot, A.C. (1986) Terpenoid antifeedants I. An overview of terpenoid antifeedants of natural origin. Recueil des Trav. Chimiq. des Pays-Bas, 105, 513–527.

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7 BIOEFFICACY MONOGRAPHS A resurgent interest in plant-derived chemicals to control pest insects stems from the need of pesticide products with less environmental hazards and health impacts than the toxic synthetic chemicals. Although many natural products show lower mammalian toxicity than organochlorine, carbamate, or other synthetic insecticides, they do not get free license for use just because they are natural products. When searching for new insect control agents, one has to be cautious about the risk that target insect species may become resistant to them and non-target invertebrates and natural enemies are not harmed. Accordingly, compounds that modify the behavior of target species and have a primarily nontoxic mode of action may in the long term provide the most dependable and environmentally safe method of chemical control. Insect antifeedants are one of the major categories of such compounds and have been extensively studied during the past decade or two as a method of insect pest management. As various aspects of antifeedant chemicals have been discussed in preceding chapters, it is essential to know such compounds from their chemical and bioefficacy point of view. Since fewer than 1% of all secondary plant substances, estimated to number 400,000 or more plus many other synthetic analogues, have been tested, and then on a limited number of insect species only, several effective compounds may remain to be discovered. Various compounds evaluated specifically as antifeedants are, therefore, presented in the form of monographs to get firsthand information about any antifeedant evaluated so far. Though it would have been more appropriate to list the compounds on the basis of their chemical structures like acyclic, alicyclic (all isoprenoids: mono-, sesqui-, di-, and triterpenoids), aromatic, heterocyclic, specific alkaloids, and so on, I have deliberately placed them in alphabetical order. The reason for this is to have an easy access to each and every compound so that a nonchemist and general reader could approach the details of efficacy and other aspects with ease. It has been the endeavor to find as much about each compound and also to relate the bioefficacy data on

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a single scale, and accordingly the feeding inhibition concentration to deter 50% of the population has been calculated in all those cases where it was possible to do so from the data presented in respective publications. However, success has been little in the sense that due to the tremendous variations in evaluations of results it was difficult to correlate the efficacy of compounds even within a group. This probably has been due to the great differences between species in their sensitivity to a given antifeedant compound. Researchers, when testing candidate compounds, employ only a few or even only one species for evaluation, so effective feeding deterrents to a particular insect will easily escape attention. For example, with a well-known antifeedant, azadirachtin, tested against seven orthopterans, the inter-specific differences span six orders of magnitude. However, the effort in the present compilation has been to put whole data on antifeedant compounds at one place in a comprehensive volume, which should give strong impetus for continual exploration of such compounds for future research, and make the practical use of insect antifeedants a reality. Here are some abbreviations used in the data sheets: B.p. EC50 ED50 FI50 FR50 i.p. ivn. LD50 M.p. PC50 PC95 s.c. [α]D

= Boiling point = Effective concentration to deter 50% of the population = = = = = = = = = = =

Effective dose to deter 50% of the population Effective feeding inhibition index level to deter 50% of the population Feeding ratio when 50% of control leaf disk area is consumed Intraperitonial Intravenous Lethal dose to kill 50% of the population Melting point Concentration to achieve 50% protection Concentration to achieve 95% protection Subcutaneous Optical rotation

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Insect Antifeedants

ABIETIC ACID (7,13-Abietadien-18-oic acid)

87

C20H30O2 (302.46)

M.p. : 172–174° [α]D24 : −106° (EtoH)

H

COOH

H

(1, 2)

(1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinnaceae) Commercial sample also tested

(2) (3)

ACTIVITY PROFILE Test Insect 1. Incisitermes minor (Hagan) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk test

Efficacy

Remarks

0.05 mg/cm2

Feeding deterrence = 27%

1. Treatment to nymphs of 10–13 mg body weight for 6 days.

0.25 mg/cm2

Feeding deterrence = 55%

Treatment to nymphs of 10–13 mg body weight for 7 days. (2) 2. Treatment to 4th and 5th instar larvae for 4 h. (3) 3. Treatment to 4th and 5th instar larvae for 4 h. (3) 4. Treatment to 4th and 5th instar larvae for 4 h. (3)

2. Neodiprion dubiosus Schedl. (Brownhead jack pine sawfly)

Pine needle application

5.0 mg/ml

Feeding deterrence = 70%

3. N. rugifrons Middleton (Redhead jack pine sawfly)

Pine needle application

7.8 mg/ml

Feeding deterrence = 70%

4. N. lecontei (Fitch) (Redhead pine sawfly)

Pine needle application

12.5 mg/ml

Feeding deterrence = 70%

LD50 (rats): 180 mg/kg (ivn.)

(4)

(1) Burgstahler, A.W. and Worden, L.R. (1961) J. Am. Chem. Soc., 83, 2587. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Soc., 9, 39. (3) Schuh, B.A. and Benjamin, D.M. (1984) J. Econ. Entomol., 77, 802. (4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8tth edition, Van Nostrand Reinhold.

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ABSINTHIN

C30H40O6 (496.64) M.p. : 182–183° (dec.) OH

[α]20 D : +180° (CHCl3)

H H

H OH

H

H

H

O

H

O

O

O

(1, 2, 4)

(1, 2, 3)

SOURCE: Artemisia absinthium L., wormwood (Asteraceae)

(1, 3)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd) (Egyptian cotton leafworm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

0.125%

Feeding inhibition = 100%

Treatment to 10- to 13-d-old larvae. There was absolute deterrence in feeding. (4)

0.063%

Feeding inhibition = 95%

(1) Novotny, L., Herout, V., and Sorm, F. (1960) Collect. Czech. Chem. Commun., 25, 1492. (2) Beauhaire, J., Fourrey, J.L., Vuilhorgne, M., and Lallemand, J.Y. (1980) Tetrahedron Lett., 21, 3191. (3) Beauhaire, J., Fourrey, J.L., Vuilhorgne, M., and Lallemand, J.Y. (1981) Tetrahedron Lett., 22, 2269. (4) Wada, K. and Munakata, K. (1971) Agric. Biol. Chem., 35, 115.

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Insect Antifeedants

ABYSSININ

89

C27H30O8 (482.53) O

M.p. : 278°

O

O H

CHO

OCH3 H O

OCOCH3

(1)

(1)

SOURCE: Bersama abyssinica Fressen., African medicinal plant (Melianthaceae)

(1)

ACTIVITY PROFILE Test Insect Helicoverpa zea (Boddie) (Cotton bollworm)

Test Method

Conc. / Dose

Leaf disk choice test

5 µg/cm2

Efficacy

Remarks

Feeding inhibition = 95%

Treatment to larvae. The treatment concentration = PC95, i.e., 95% protection of foliage was achieved. (1)

(1) Kubo, I. and Matsumoto, T. (1984) Tetrahedron Lett., 25, 4601.

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2-ACETONAPHTHONE

C12H10O (170.21)

M.p. : 56° B.p. : 171–173°/17 mm

O

(1, 2)

(1)

SOURCE: Commercial sample (Occurs in many essential oils)

(2)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method Leaf disk dual-choice test

Conc. / Dose 5 × 10–7 mol/cm2

Efficacy

Remarks

Feeding inhibition = 99.2%

Treatment to 5th instar larvae prestarved for 3 h. The treatment given for 2 h. (2)

LD50 (mice): 599 mg/kg (oral) (1) Immediata, T. and Day, A.R. (1940) J. Org. Chem., 5, 512. (2) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130. (3) Opdyke, D.L.J. (1975) Food Cosmet. Toxicol., 13, 867.

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(3)

Insect Antifeedants

2α-ACETOXY-1α-ACETOXYMETHYL-5,5DIMETHYL-1α,6β-10 O, α-BICYCLO DECANE -10-SPIRO-2′-OXIRAN

91

C18H28O5 (324.42)

M.p. : 105.5–106°

H

O OCOCH3 OCOCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Locusta migratoria L. (Migratory locust)

Test Method

Conc. / Dose

Glass fiber disk test

100 ppm

Efficacy Feeding inhibition = 70%

Remarks Treatment to laststage nymphs. (1)

(1) Ley, S.V., Neuhaus, D., Simpkins, N.S., and Whittle, A.J. (1982) J. Chem. Soc. Perkin I, 2157.

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2β-ACETOXY-1α-ACETOXYMETHYL-5,5DIMETHYL-1α,6α-10 O,α-BICYCLO DECANE -10-SPIRO-2′-OXIRAN

C18H28O5 (324.42)

M.p. : 64°

H

O OCOCH3 OCOCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Locusta migratoria L. (Migratory locust)

Test Method Glass fiber disk test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding inhibition = 72%

Treatment to laststage nymphs. This isomer, however, inhibited 72% feeding at a high concentration of 1000 ppm. (1)

(1) Jackson, W.P. and Ley, S.V. (1981) J. Chem. Soc. Perkin I, 1516.

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Insect Antifeedants

19-ACETOXY-18 CHLORO-4α-HYDROXY-6OXONEOCLEROD-13-EN-15,16 OLIDE

93

C22H31O6Cl (426.94)

O

M.p. : 154–156° [α]D22 : –41.7° (CHCl3)

O

HO

O Cl

OAc

(1)

(1)

SOURCE: Semisynthetic, prepared from ajugarin II

(1)

ACTIVITY PROFILE Test Insect Spodoptera exigua (Hubner) (Beet armyworm)

Test Method

Conc. / Dose

Efficacy

Remarks

Leaf disk test

1000 ppm

Feeding inhibition =

Treatment to newly emerged 5th instar larvae pre-starved for 6 h until 50% of the control disks were consumed in choice situation and 75% in no-choice assay. Assayed against Leptinotarsa decemlineata as well but found inactive against this species. (1)

No-choice Choice

29.9% 91.7%

(1) Caballero, C., Castanera, P., Ortego, F., Fontana, G., Pierro, P., Savona, G., and Rodriguez, B. (2001) Phytochemistry, 58, 249.

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19-ACETOXY-4,6-DIOXO-18-NORNEOCLEROD-13-EN-15,16 OLIDE

C21H28O6 (376.45) O

[α]22 D : +8.2° (CHCl3)

O

O OAc

M.p. : 176–177°

O

(1)

(1)

SOURCE: Semisynthetic, prepared from ajugarin II

(1)

ACTIVITY PROFILE Test Insect Spodoptera exigua (Hubner) (Beet armyworm)

Test Method

Conc. / Dose

Efficacy

Remarks

Leaf disk test

1000 ppm

Feeding inhibition =

Treatment to newly emerged 5th instar larvae pre-starved for 6 h until 50% of the control disks were consumed in choice situation and 75% in no-choice assay. Assayed against Leptinotarsa decemlineata as well but found inactive against this species. (1)

No-choice Choice

9.9% 72.9%

(1) Caballero, C., Castanera, P., Ortego, F., Fontana, G., Pierro, P., Savona, G., and Rodriguez, B. (2001) Phytochemistry, 58, 249.

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Insect Antifeedants

11β-ACETOXY-5α-ISOBUTYRYLOXYSILPHINEN-3-ONE

95

C21H30O5 (362.21)

Oil Only spectral data given

OAc

O

C

O

O

(1)

(1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Choice leaf disk feeding assay

~100 nmol/cm2

Feeding deterrence = 50.0%

1. Treatment to L6 larvae for 24 h. Concentration = EC50

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Choice leaf disk feeding assay

0.08 nmol/cm2

Feeding deterrence = 50.0%

2. Treatment to adults for 24 h. Concentration = EC50

3. Diuraphis noxia (Mordvilko) (Solanum aphid)

Choice feeding assay

8.0 nmol/cm2

Feeding deterrence = 50.0%

3. Treatment to adults for 24 h. Concentration = EC50

4. Myzus persicae (Sulzer) (Green peach aphid)

Choice feeding assay

29.3 nmol/cm2

Feeding deterrence = 50.0%

4. Treatment to adults for 24 h. Concentration = EC50 (1)

(1) Gonzalez-Coloma, A., Valencia, F., Martin, N., Hoffmann, J.J., Hutter, L., Marco, J.A., and Reina, M. (2002) J. Chem. Ecol., 28, 117.

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11β-ACETOXY-5α-TIGLOYLOXYSILPHINEN-3-ONE

C22H30O5 (374.21)

OAc

O

Oil Only spectral data given

O

O

(1)

(1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Choice leaf disk feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

1. Treatment to L6 larvae for 24 h. Concentration = EC50

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Choice leaf disk feeding assay

0.17 nmol/cm2

Feeding deterrence = 50.0%

2. Treatment to adults for 24 h. Concentration = EC50

3. Diuraphis noxia (Mordvilko) (Solanum aphid)

Choice feeding assay

>120 nmol/cm2

Feeding deterrence = 50.0%

3. Treatment to adults for 24 h. Concentration = EC50 (1)

(1) Gonzalez-Coloma, A., Valencia, F., Martin, N., Hoffmann, J.J., Hutter, L., Marco, J.A., and Reina, M. (2002) J. Chem. Ecol., 28, 117.

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Insect Antifeedants

11β-HYDROXY-5α-ANGELOYLOXYSILPHINEN-3-ONE

97

C20H28O4 (332.44)

Oil Only spectral data given

OH

OAng

O

(1)

(1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Choice leaf disk feeding assay

>150 nmol/cm2

Feeding deterrence = 50.0%

1. Treatment to L6 larvae for 24 h. Concentration = EC50

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Choice leaf disk feeding assay

21.6 nmol/cm2

Feeding deterrence = 50.0%

2. Treatment to adults for 24 h. Concentration = EC50

3. Diuraphis noxia (Mordvilko) (Solanum aphid)

Choice feeding assay

38.8 nmol/cm2

Feeding deterrence = 50.0%

3. Treatment to adults for 24 h. Concentration = EC50 (1)

(1) Gonzalez-Coloma, A., Valencia, F., Martin, N., Hoffmann, J.J., Hutter, L., Marco, J.A., and Reina, M. (2002) J. Chem. Ecol., 28, 117.

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11β-ACETOXY-5α (ANGELOYLOXY) SILPHINEN-3-ONE

C22H30O5 (374.48)

Oil [α]D : –69° (CHCl3)

OAc

OAng

O

(1, 3)

(1, 3) SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae)

(1, 2)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice assay

Conc. / Dose

Efficacy

Remarks

1.69 µg/cm2

Feeding inhibition = 50%

Treatment to newly emerged 4th instar larvae for ≤ 6 h.

14.43 µg/cm2

Feeding inhibition = 50%

Treatment to newly emerged 4th instar larvae for 24 h. Concentration = FI50 values. (2)

(1) Gonzalez-Coloma, A., Reina, M., Cabrera, R., Castanera, P., and Gutierrez, C. (1995) J. Chem. Ecol., 21, 1255. (2) Gonzalez-Coloma, A., Gutierrez, C., Cabrera, R., and Reina, M. (1997) J. Agric. Food Chem., 45, 946. (3) Jakupovic, J. and Abraham, W.R. (1985) Phytochemistry, 24, 3048.

© 2005 by CRC Press LLC

Insect Antifeedants

12-α-ACETOXYFRAXINELLONE

99

C16H18O5 (290.32)

M.p. : 102–104°C

O

O

O O

O

structure under review (1)

(1)

SOURCE: Melia azedarach L., darekh (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy Feeding inhibition = 100%

Remarks Treatment to 3rd instar larvae. (1)

(1) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., and Tadera, K. (1998) Phytochemistry, 49, 1773.

© 2005 by CRC Press LLC

100

Opender Koul

12β-ACETOXYHARRISONIN

C29H34O12 (574.58)

M.p. : 253–254°

O

OAc

O O O O

O OH

HO

O O

(1, 2)

(1)

SOURCE: Harrisonia abyssinica Oliv., East African medicinal plant (Simaroubaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice assay

500 ppm

Feeding inhibition = 100%

1. Treatment to 3rd instar larvae. Only one of the few antifeedants active against this voracious herbivore. (2)

2. Eldana saccharina Walker (sugar cane borer)

Leaf disk choice assay

100 µg/disk

Feeding inhibition = 54 ± 8%

2. Treatment to 12-h pre-starved late 5th instar larvae. (3)

3. Maruca testulalis (Geyer) (bean pod borer)

Leaf disk choice test

100 µg/disk

Feeding deterrence = 84 ± 10%

10 µg/disk

Feeding deterrence = 46 ± 15%

3. Treatment to 12-h pre-starved late 5th instar larvae. (3)

(1) Liu, H., Kubo, I., and Nakanishi, K. (1982) Heterocycles, 17, 67. (2) Rajab, M.S., Rugutt, J.K., Fronczek, F.R., and Fischer, N.H. (1997) J. Nat. Prod., 60, 822. (3) Hassanali, A., Bentley, M.D., Sitayo, E.N.O., Njoroge, P.E.W., and Yatagai, M. (1986) Insect Sci. Applic., 7, 495.

© 2005 by CRC Press LLC

Insect Antifeedants

7β-ACETOXY (–)-KAUR-16-EN-19-OIC ACID

101

C22H32O4 (360.49)

Only spectral data given

H H

H OAc COOH

(1)

(1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae)

(1)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method Paper disk choice bioassay

Conc. / Dose

Efficacy

2500 ppm

Feeding inhibition index = 0

1000 ppm

Feeding inhibition index = 5.4

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

Remarks Treatment to 2nd instar workers where feeding was continued for 14 days. Antifeedant index value below 20 was considered highly deterrent in this evaluation. (1)

102

Opender Koul

15β-ACETOXY (–)-KAUR-16-EN-19-OIC ACID

C22H32O4 (360.49)

Only spectral data given

H H

OAc

COOH

(1)

(1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae)

(1)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method Paper disk choice bioassay

Conc. / Dose 2500 ppm

Efficacy Feeding inhibition index = 32.9

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

Remarks Treatment to 2nd instar workers where feeding was continued for 14 days. Antifeedant index value below 20 was considered highly deterrent in this evaluation. (1)

Insect Antifeedants

5α-ACETOXYSILPHINEN-3-ONE

103

C17H24O3 (276.37)

Oil [α]D : –3° (CH2Cl2)

O

OAc

(1)

(1) SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

1. Spodoptera littoralis (Boisd.) (Eygyptian cotton leaf worm)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

1. Treatment to 6th instar larvae.

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Choice feeding assay

2.81 nmol/cm2

Feeding deterrence = 50.0%

2. Treatment to adults.

3. Myzus persicae (Sulzer) (Green peach aphid)

Choice feeding assay

>500 nmol/cm2

Feeding deterrence = 50.0%

3. Treatment to apterous adult aphids.

4. Rhopalosiphum padi (L.) (Cereal aphid)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

4. Treatment to apterous adult aphids.

5. Sitobion avenae (Fab.) (Grass aphid)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

5. Treatment to apterous adult aphids.

6. Diuraphis noxia (Mordvilko) (Wheat aphid)

Choice feeding assay

57.4 nmol/cm2

Feeding deterrence = 50.0%

6. Treatment to apterous adult aphids. Concentrations = EC50 values.

Efficacy

Remarks

(1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.

© 2005 by CRC Press LLC

104

Opender Koul

21-ACETOXYTOONACILID

C33H40O12 (628.67)

[α]20 D : +47.5° (CHCl3)

O

O OAc AcO

OAc

O O

CH2

COOCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf disk test

Conc. / Dose 0.05%

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to adult beetles, absolute feeding deterrence achieved within 24 h. (1)

(1) Kraus, W. and Grimminger, W. (1980) Nour. J. de Chimie, 4, 651.

© 2005 by CRC Press LLC

Insect Antifeedants

6-ACETOXYTOONACILIN

105

C33H40O11 (612.67) O

M.p. : 215° [α]D20 : +42.5° (CHCl3)

OAc AcO

O O

H2C

OAc

COOCH3

(1)

(1) SOURCE: Toona ciliata M.J. Roem, red cedar (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf disk test

Conc. / Dose 0.2%

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to adult beetles, absolute feeding deterrence achieved within 24 h. (2)

(1) Kraus, W., Grimminger, W., and Sawitzki, G. (1978) Angew. Chemie., 17, 452. (2) Kraus, W. and Grimminger, W. (1980) Nour. J. de Chimie, 4, 651.

© 2005 by CRC Press LLC

106

Opender Koul

1β-ACETOXY-2β,8β,9α-TRIBENZOYLOXY-4α, 6α-DIHYDROXY-β-DIHYDROAGAROFURAN

OAc

C38H40O11 (672.73)

M.p. : 245–246°

OBz OBz

BzO

O HO

OH

(1)

(1)

SOURCE: Celastrus rosthornianus Loes., bitter tree (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect Pieris rapae (L.) (Imported cabbage worm)

Test Method

Conc. / Dose

Macerated leaf feeding

500 ppm

(1) Tu, Y.Q. (1991) J. Chem. Soc. Perkin Trans. I, 425.

© 2005 by CRC Press LLC

Efficacy

Remarks

Feeding inhibition = 49.0%

Treatment to larvae pre-starved for 3 h. (1)

Insect Antifeedants

12-O-ACETYLAZEDARACHIN–A

107

C35H46O12 (658.74) O

[α]22 D : +7.5° (MeOH)

OAc

HO

O

O

O AcO

OH OCO

(1)

(1, 2) SOURCE: Melia azedarach L., chinaberry (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice assay

400 ppm or 8 µg/cm2

Feeding inhibition

1. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (2)

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice assay

400 ppm or 8 µg/cm2

Feeding inhibition

2. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. Concentration = minimum level required for inhibition. (2)

(1) Huang, R.C., Okamura, H., Iwagawa, T., and Nakatani, M. (1994) Bull. Chem. Soc. Jap., 67, 2468. (2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

108

Opender Koul

12-O-ACETYLAZEDARACHIN–B

C34H44O12 (644.71) O

[α]22 D : −55° (MeOH)

OAc

HO

O

O

O AcO

OH

OCO

(1)

(1, 2) SOURCE: Melia azedarach L., chinaberry (Meliaceae) M. Toosendan Sieb. et Zucc., Chinese melia (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice assay

400 ppm or 8 µg/cm2

Feeding inhibition

1. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (2)

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice assay

400 ppm or 8 µg/cm2

Feeding inhibition

2. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. Concentration = minimum level required for inhibition. (2)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117. (2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

Insect Antifeedants

1-O-ACETYL-3-DEACETYL-1DETIGLOYLSALANNIN

109

C28H36O8 (500.56)

Only spectral data given

O

AcO

HO

COOCH3

O H O

(1) SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to starved final stadium larvae (24 to 36 h old). Bioassay terminated after the larvae had eaten approximately 50% of one of the disks in each case.

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leafworm)

Glass fiber disk choice assay

1.0 ppm

Feeding inhibition = 44.0%

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk choice assay

1.0 ppm

Feeding inhibition = 31.0%

3. Heliothis virescens (Fab.) (Tobacco budworm)

Glass fiber disk choice test

1.0 ppm

Feeding inhibition = 11.0%

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Glass fiber disk choice test

1.0 ppm

Feeding inhibition = 21.0%

EC50 approximately 1.5 ppm to 2.0 ppm in this bioassay. (1)

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149.

© 2005 by CRC Press LLC

110

Opender Koul

1-O-ACETYL-1-DETIGLOYLSALANNIN

C31H40O9 (556.65)

Only spectral data given

O COOCH3 AcO H

O

AcO H O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice assay

Conc. / Dose >400 µg/cm2

Efficacy

Remarks

Feeding inhibition = 50%

Treatment to newly emerged 3rd instar larvae. Leaf disks examined every 2 h until 95% of control disks were eaten. Concentration used here is protection. Concentration = PC50 value. (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC

Insect Antifeedants

2-ACETYL-14,15-DIHYDRO AJUGAPTIN

111

C31H46O11 (594.70) H

Only spectral data given

O H O H

H H

CH3COO

COO O OCOCH3 OCOCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Leaf disk choice assay

1.0 µg/cm2

Efficacy Feeding ratio = 0.06 ± 0.02 (i.e., FR50 value: the ratio when 50% of control disk area has been consumed)

(1) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC

Remarks Treatment to newly ecdysed 5th instar larvae. FR50 = < 0.5 Considered as excellent antifeedant activity. (1)

112

Opender Koul

ACETYLISOMONTANOLIDE

C24H32O8 (448.51)

M.p. : 134° [α]20 D : −78.2° (CHCl3)

OOCCH3

OOC

OOCCH3 O

O

(1)

(1, 2) SOURCE: Laserpitium siler L., mountain lasser wort (Apiaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

1.0%

Feeding deterrence coefficient = 103 (adults)

1. Treatment given to adults.

2. Tribolium confusum Jacq. Duv. (Confused flour beetle)

Wafer disk test

1.0%

Feeding deterrence coefficient = 106 (adults) 85 (larvae)

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

1.0%

Feeding deterrence coefficient = 43 (larvae)

3. Treatment given to adults. Neutral value = 0 Absolute feeding deterrence value = 200. (2)

(1) Holub, M., Motl, O., Samek, Z., and Herout, V. (1972) Collect. Czech. Chem. Commun., 37, 1186. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

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Insect Antifeedants

2-ACETYLIVAIN-1

113

C31H46O11 (580.67) H

[α]20 D : +15.9° (CHCl3)

O H O H

H H

CH3COO

COO O OCOCH3 OCOCH3

(1)

(1, 2) SOURCE: Ajuga pseudoiva (L.) Schreber., African ajuga (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Leaf disk choice assay

1.0 µg/cm2

Efficacy Feeding ratio = 0.12 ± 0.04 (i.e., FR50 value: the ratio when 50% of control disk area has been consumed)

0.1 µg/cm2

Feeding ratio = 0.51 ± 0.05

(1) Camps, F., Coll, J., and Dargallo, O. (1984) Phytochemistry, 23, 387. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC

Remarks Treatment to newly ecdysed 5th instar larvae. FR50 = < 0.5 Considered as excellent antifeedant activity.

(2)

114

Opender Koul

6-ACETYLNIMBANDIOL

C28H34O8 (498.57)

OCH3 O

M.p. : 178° [α]D20 : +245° (CHCl3)

O

O

O HO OAc

(1)

(1) SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Bean leaf choice assay

Conc. / Dose 0.011%

Efficacy

Remarks

Feeding inhibition = 50%

Treatment to 4th instar larvae for 24 h. Concentration = EC50 value. (2)

(1) Kraus, W. and Cramer, R. (1981) Chem. Ber., 114, 2375. (2) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–198.

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Insect Antifeedants

3-O-ACETYLOHCHINOLAL

115

C36H46O11 (654.75)

O

Amorphous powder [α]D : +62°(CH3OH)

O COOCH3 O

O

AcO CHO

OAc

(1)

(1) SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania(Cramer) (Southern armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

1000 ppm (20 µg/ml)

Feeding deterrence = 50%

Treatment given to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (1)

(1) Zhou, J., Minami, Y., Yagi, F., Tadera, K., and Nakatani, M.(1997) Phytochemistry, 46, 911.

© 2005 by CRC Press LLC

116

Opender Koul

19-ACETYLTEUPOLIN–IV

C24H28O9 (460.48) O

M.p. : 230–234° [α]24 D : +132.3° (pyridine)

O O

OAc O OAc

O

(1, 2)

(1, 2) SOURCE: Teucrium polium pilosum, (L.) Decne., golden germander (Labiatae)

(1)

ACTIVITY PROFILE Test Insect No specific insect species mentioned

Test Method Leaf disk choice test

Conc. / Dose

Efficacy Feeding deterrent

Remarks Reported as insect feeding deterrent but no specific quantitative data have been recorded. (1)

(1) De la Torre, M.C., Piozzi, F., Rizk, A.-F., Rodriguez, B., and Savona, G. (1986) Phytochemistry, 25, 2239. (2) Hundal, G. and Martinez-Ripoll, M. (1996) Acta Cryst., 52C, 3157.

© 2005 by CRC Press LLC

Insect Antifeedants

7-ACETYLTRICHILIN–A

117

C37H48O14 (716.78) O

Only spectral data given

OH

HO

O

AcO O

O AcO

OAc

OCO

(1, 2)

(1)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

500 ppm

2. Epilachna varivestis Muls. (Mexican bean beetle)

Leaf disk choice test

500 ppm

3. Spodoptera littoralis (Boisd.) (Egyptian cotton leafworm)

Leaf disk choice test

500 ppm

Test Insect

Efficacy Feeding deterrent for all the three species.

Remarks Treatment given to larvae for 6–24 h. No quantitative data recorded for any of the species for this compound. (1)

(1) Nakatani, M., Iwashita, T., Naoki, H., and Hase, T. (1985) Phytochemistry, 24, 195. (2) Nakanishi, K., Cooper, R., and Nakatani, M. (1981) Proc. Inst. Org. Phys. Chem. Wroclaw, 7, 1091.

© 2005 by CRC Press LLC

118

Opender Koul

12-O-ACETYLTRICHILIN–B

C37H48O14 (716.78) O

[α]22 D : −2.5° (MeOH)

OAc

HO

O

AcO O

O AcO

OH

OCO

(1, 2)

(1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice assay

400 ppm or 8 µg/cm2

Feeding inhibition

1. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (2)

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice assay

400 ppm or 8 µg/cm2

Feeding inhibition

2. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. Concentration = minimum level required for inhibition. (2)

(1) Nakatani, M., Huang, R.C., Okamura, H., Naoki, H., and Iwagawa, T. (1994) Phytochemistry, 36, 39. (2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

Insect Antifeedants

ACETYLVISMINONE–B

119

C23H24O6 (396.44)

O

OH

M.p. : 115–120° (dec.)

O

OCH3

AcO

(1, 2)

(1, 2)

SOURCE: Synthetic Visma japuransis (Hypericaceae)

(1) (2)

ACTIVITY PROFILE Test Insect Locusta migratoria L. (migratory locust)

Test Method Glass fiber disk test

Conc. / Dose 10–3 M

Efficacy Feeding inhibition = 100%

Remarks Treatment to last stage nymphs. (1)

(1) Simmonds, M.S.J., Blaney, W.M., DelleMonache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem. Ecol., 11, 1593. (2) Pinheiro, R.M., Quhae, M.M., Bettolo, G.B.M., and Monache, F.D. (1984) Phytochemistry 23, 1737.

© 2005 by CRC Press LLC

120

Opender Koul

ACROPTILLIN

C19H23O7Cl (398.84) CH2

M.p. : 197–199° [α]D : +100° (MeOH)

Cl HO

OOC OH O CH2

O

O

(1, 2, 3)

(1, 2, 3)

SOURCE: Centaurea bella Trautv., tumbleweed (Cynaraceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

10.0 mg/cm3

Feeding deterrence coefficient = 57 (adults)

1. Treatment given to adults.

2. Tribolium confusum Jacq. Duv. (Confused flour beetle)

Wafer disk test

10.0 mg/cm3

Feeding deterrence coefficient = 88.7 (adults) 47.5 (larvae)

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10.0 mg/cm3

Feeding deterrence coefficient = 47.4 (larvae)

3. Treatment given to adults.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200. (2)

(1) Evstratova, R.I., Sheichenko, V.I., and Rybalko, K.S. (1973) Khim. Prir. Soedin., 9, 161. (2) Nawrot, J., Bloszyk, E., Girabarczyk, H., Dorzdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk. Inst. Ochr. Roslin., 25, 91. (3) Stevens, K.L. (1982) Phytochemistry, 21, 1093.

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Insect Antifeedants

AFLAVAZOLE

121

C28H35O2N (417.59) OH

M.p. : 156–160° (dec.) [α]D : +2.8° (CH3OH)

OH N H

(1)

(1) SOURCE: Aspergillus flavus Link, common mould (Fungi)

(1)

ACTIVITY PROFILE Test Insect Carpophilus hemipterus (L.) (Dried fruit beetle)

Test Method Artificial diet test

Conc. / Dose

Efficacy

Remarks

100 ppm

Feeding deterrence = Threshold level

Treatment given to adults.

200–600 ppm

Feeding deterrence = 100%

Variation obtained in achieving absolute feeding deterrence in different experiments. (1)

(1) TePaske, M.R., Gloer, J.B., Wicklow, D.T., and Dowd, P.F. (1990) J. Org. Chem., 55, 5299.

© 2005 by CRC Press LLC

122

Opender Koul

AGERATRIOL

C15H24O3 (252.35)

M.p. : 195° [α]20 D : +30.5° (CH3OH)

OH

OH CH2

OH CH2

CH2

(1)

(1, 2) SOURCE: Achillea ageratum L., yarrow (Asteraceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

10.0 mg/cm3

Feeding deterrence coefficient = 55.8 (adults)

1. Treatment given to adults. (2)

2. Tribolium confusum Jacq. Duv. (Confused flour beetle)

Wafer disk test

10.0 mg/cm3

Feeding deterrence coefficient = 64.6 (adults) 52.7 (larvae)

2. Treatment given to both adults and larvae. (2)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10.0 mg/cm3

Feeding deterrence coefficient = 97.2 (adults)

3. Treatment given to adults.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200. (2)

(1) Garanti, L., Marchesini, A., Pagnoni, U.M., and Trave, R. (1972) Tetrahedron Lett., 13, 1397. (2) Nawrot, J., Bloszyk, E., Girabarczyk, H., Dorzdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk. Inst. Ochr. Roslin., 25, 91.

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Insect Antifeedants

AGINOSIDE

123

C50H82O24 (1067.18) O

M.p. : 272–276° (dec.) [α]D29 : –66.7° (CHCl3)

O HO

xyl

gul

gul

O OH

(3)

(1, 3) SOURCE: Allium porrum (L.) Regel., elephant garlic (Amaryllidaceae) A. giganteum L.

(1)

ACTIVITY PROFILE Test Insect Peridroma saucia Hubner (Variegated cutworm)

Test Method

Conc. / Dose

Leaf disk choice test

Efficacy

Remarks

2.85 µg/cm2

Feeding deterrence = 67.3%

Treatment to 5th instar larvae for 5 h. (2)

11.4 µg/cm2

Feeding deterrence = 84.7%

28.5 µg/cm2

Feeding deterrence = 95.5%

57.0 µg/cm2

Feeding deterrence = 100%

EC50 calculated = 2.27 µg/cm2

(1) Harmatha, J., Mauchamp, B., Arnault, C., and Slama, K. (1987) Biochem. Syst. Ecol., 15, 113. (2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194. (3) (1994) Dictionary of Natural Products, Chapman & Hall, London.

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124

Opender Koul

AILANTHINONE

C25H34O9 (478.54)

M.p. : 227–230° [α]27 D : +90° (CHCl3)

OH HO HO

O

O

OCO

O

O

(1)

(1, 2) SOURCE: Pierreodendron kerstingii (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens Fab. (Tobacco budworm)

Test Method

Conc. / Dose

Leaf disk choice test

19.8 µg/cm2

Efficacy Feeding deterrence = 60–90% after 2 days

Remarks Treatment to 3rd instar larvae. (2)

Feeding deterrence = 30–60% after 6 days

(1) Kupchan, S.M. and Lacadie, J.A. (1975) J. Org. Chem., 40, 654. (2) Lidert, Z., Wiing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K. (1987) J. Nat. Prod., 50, 442.

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Insect Antifeedants

AJUGAREPTANSIN

125

C29H44O10 (552.66) H

Amorphous [α]D20 : –28° (CCl4)

O H O H

COO H H

H

HO O OCOCH3 OCOCH3

(1)

(1, 2) SOURCE: Ajuga reptans L., Catlins giant (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Leaf disk choice test

10.0 µg/cm2

Efficacy Feeding ratio = 0.20 ± 0.07 (i.e., FR50 value: the ratio when 50% of control disk area is consumed)

(1) Camps, F., Coll, J., Cortel, A., and Messeguer, A. (1979) Tetrahedron Lett., 20, 1709. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC

Remarks Treatment to newly ecdysed 5th instar larvae. FR50 = < 0.5 considered as excellent feeding deterrent. (2)

126

Opender Koul

AJUGAREPTANSONE–A

C29H40O10 (548.63) O

M.p. : 177–180° [α]D : –6° (CHCl3)

O

O

COO O OCOCH3 OCOCH3

(1)

(1, 2)

SOURCE: Ajuga reptans L., Catlins giant (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Leaf disk choice test

25.0 µg/cm2

Efficacy Feeding ratio = 0.74 ± 0.12 (i.e., FR50 value: the ratio when 50% of control disk area is consumed)

(1) Camps, F., Coll, J., and Cortel, A. (1981) Chem. Lett., 1093. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC

Remarks Treatment to newly ecdysed 5th instar larvae. FR50 = < 0.5 considered as excellent feeding deterrent. Thus this compound has moderate activity. (2)

Insect Antifeedants

AJUGAPITIN (Clerodendrin D)

127

C29H42O10 (550.65)

M.p. : 196–198°

O H

[α]D20 : –70.3° (CHCl3)

O H H

H

H

HO COO O OCOCH3 OCOCH3

(1)

(1, 2) SOURCE: Ajuga chamaepitys (L.) Schreb., ground pine (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose 1.0 µg/cm2

Efficacy Feeding ratio = 0.04 ± 0.0 (i.e., FR50 value: the ratio when 50% of control disk area is consumed)

0.1 µg/cm2

FR50 = 0.24 ± 0.06

0.01 µg/cm2

FR50 = 0.41 ± 0.10

Remarks Treatment to newly ecdysed 5th instar larvae. FR50 = < 0.5 considered as excellent feeding deterrent. Thus this compound has moderate activity. (2)

(1) Hernandez, A., Pascual, C., Sanz, J., and Rodriguez, B. (1982) Phytochemistry, 21, 2909. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

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128

Opender Koul

AJUGARIN–I

C24H34O7 (434.53) O

H

M.p. : 155–157°

O

O OAc CH2OAc

(1)

(1,2)

SOURCE: Ajuga remota Benth., African ajuga (Labiatae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (African armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Leaf disk choice test

100 ppm

Leaf disk choice test

300 ppm

Efficacy

Remarks

Minimum level of treatment to exhibit antifeedant activity.

1. Treatment to larvae at random.

Minimum level of treatment to exhibit antifeedant activity.

2. Treatment to larvae at random.

(1)

(1)

Glass fiber disk choice test

100 ppm

Feeding deterrence = 43%

Treatment to final stadium larvae for 12 h. (2)

3. Schistocerca gregaria Forsk. (Desert locust)

Leaf disk choice test

60 µg/l

Minimum level of treatment to exhibit antifeedant activity.

3. Treatment to 3- to 5-day-old well-fed 5th instar larvae. (3)

4. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk No-choice test Choice test

Feeding deterrence = 70.04% 67.9%

4. Treatment to 4th instar larvae prestarved for 6 h. (4)

1000 ppm 1000 ppm

(1) Kubo, I., Lee, Y., Balogh-Nair, V., Nakanishi, K., and Chapya, A. (1976) J. Chem. Soc. Chem Commun., 949. (2) Cole, M.D., Anderson, J.C., Blaney, W.M., Fellows, L.E., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J. (1990) Phytochemistry, 29, 1793. (3) Kubo, I. and Nakanishi, K. (1979) Adv. Pestic. Sci., 2, 284. (4) Caballero, C., Castanera, P., Ortego, F., Fontana, G., Pierro, P., Savona, G., and Rodriguez, B. (2001) Phytochemistry, 58, 249.

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Insect Antifeedants

AJUGARIN–II

129

C22H36O6 (396.52) O

H

M.p. : 188–189° [α]D24 : +14.6° (CDCl3)

O

O OH CH2OAc

(1,2)

(1) SOURCE: Ajuga remota Benth., African ajuga (Labiatae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (African armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Leaf disk choice test

100 ppm

Leaf disk choice test

300 ppm

Efficacy

Remarks

Minimum level of treatment to exhibit antifeedant activity.

1. Treatment to larvae at random.

Minimum level of treatment to exhibit antifeedant activity.

2. Treatment to larvae at random.

(1)

(1)

(1) Kubo, I., Lee, Y., Balogh-Nair, V., Nakanishi, K., and Chapya, A. (1976) J. Chem. Soc. Chem. Commun., 949. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

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130

Opender Koul

AJUGARIN–III

C24H36O8 (452.54)

O

H

M.p. : 243–245°

O

HO HOH2C

OAc CH2OAc (1)

(1)

SOURCE: Ajuga remota Benth., African ajuga (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera exempta (Walker) (African armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

100 ppm

Efficacy

Remarks

Minimum level of treatment to exhibit antifeedant activity.

Treatment to larvae at random. (2)

(1) Kubo, I., Lee, Y., Balogh-Nair, V., Nakanishi, K., and Chapya, A. (1976) J. Chem. Soc. Chem. Commun., 949. (2) Kubo, I. and Nakanishi, K. (1979) Adv. Pestic. Sci., 2, 284.

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Insect Antifeedants

ALANTOLACTONE

131

C15H20O2 (232.32)

M.p. : 78.5–80.0° B.p. : 275° [α]D : +175° (CHCl3)

O O

CH2

(1, 2)

(1, 2) SOURCE: Inula helenium L., eleocampane (Asteraceae)

(1, 3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

10.0 mg/cm3

Feeding deterrence coefficient = 119 (adults)

1. Treatment given to adults. (3)

2. Tribolium confusum Jacq. Duv. (Confused flour beetle)

Wafer disk test

10.0 mg/cm3

Feeding deterrence coefficient = 197 (adults) 177 (larvae)

2. Treatment given to both adults and larvae. (3)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10.0 mg/cm3

Feeding deterrence coefficient = 148 (adults)

3. Treatment given to adults.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200. (3)

(1) Asselineau, C. and Borg, S. (1958) Comp. Rend., 246, 1874. (2) Marshall, J.A. and Cohen, N. (1964) J. Org. Chem., 29, 3727. (3) Streibl, M., Nawrot, J., and Herout, V. (1983) Biochem. Syst. Ecol., 11, 381.

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132

Opender Koul

ALATOLIDE

C19H26O6 (350.41)

M.p. : 59–61° [α]D25 : +64.4° (CHCl3)

CH2OH OCO

CH2

CH2OH

O O

(1, 2)

(1, 2) SOURCE: Jurinea alata Cass., jurinea weed (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

8.0 mg/cm3

Feeding deterrence coefficient = 51–100 (adults)

1. Treatment given to adults. (2)

2. Tribolium confusum Jacq. Duv. (Confused flour beetle)

Wafer disk test

8.0 mg/cm3

Feeding deterrence coefficient = 51–100 (adults) 101–150 (larvae)

2. Treatment given to both adults and larvae. (2)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

8.0 mg/cm3

Feeding deterrence coefficient = 151–200 (adults)

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200. (2)

(1) Drozdz, B., Samek, Z., Holub, M., and Herout, V. (1973) Collect. Czech. Chem. Commun., 38, 727. (2) Nawrot, J., Bloszyk, K.E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin, 24, 27.

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Insect Antifeedants

ALBIZZINE

133

C4H9O3N3 (147.14)

M.p. : 218–220° (dec.) [α]25 D : –66.2° (H2O)

COOH

H 2N

C

H

CH2NHCONH2

(1, 2)

(1, 2) SOURCE: Acacia sp. (Fabaceae)

(3)

ACTIVITY PROFILE Test Insect Locusta migratoria migratoriodes (R & F) (Migratory locust)

Test Method Glass fiber disk test

Conc. / Dose 1.0% of disk weight

Efficacy

Remarks

Feeding inhibition = 91–100%

Treatment to male 5th instar nymphs. (3)

(1) Gmelin, R., Strauss, G., and Hasenmaier, G. (1958) Z. Naturforsch., 13B, 252. (2) Kjaer, A., Larsen, P.O., and Gmelin, R. (1959) Experientia, 15, 253. (3) Evans, C.S. and Bell, E.A. (1979) Phytochemistry, 18, 1807.

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134

Opender Koul

ALLIARINOSIDE

C10H15O6N (245.22)

Colorless gum Only spectral data given

OH

O

O

HO HO OH

H

CN

(1)

(1)

SOURCE: Alliaria petiolata Cavara and Grande, garlic mustard (Cruciferae)

(1)

ACTIVITY PROFILE Test Insect Pieris napi oleracea L. (Green-veined white butterfly)

Test Method Leaf disk choice test

Conc. / Dose 0.1 g leaf equivalent/ 20 µl/1.5 cm disk

Efficacy Feeding inhibition observed. No quantitative data given.

Remarks Treatment to neonate larvae for 18 h. (1)

(1) Haribal, M., Yang, Z., Attygalle, A.B., Renwick, A.J.A., and Meinwald, J. (2001) J. Nat. Prod., 64, 440.

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Insect Antifeedants

2-AMINO-3-OXALYL AMINO PROPANOIC ACID

135

C5H8O5N2 (176.13)

M.p. : 206° (dec.) [α]D27 : –36.9° (HCl)

COOH

H

C

NH2

CH2NHCOCOOH

(1)

(1, 2) SOURCE: Acacia sp. (Fabaceae)

(2)

ACTIVITY PROFILE Test Insect 1. Anacridium melanorhodon arabafrum (Dirsh.) (Tree locust)

2. Locusta migratoria migratoriodes (R and F) (Migratory locust)

Test Method Glass fiber disk test

Glass fiber disk test

Conc. / Dose

Efficacy

Remarks

0.5% of disk weight

Feeding inhibition = 61–90%

1.0% of disk weight

Feeding inhibition = 91–100%

1. Treatment at random to 3rd to 6th instar nymphs. (2)

1.0% of disk weight

Feeding inhibition = 30–60%

10.0% of disk weight

Feeding inhibition = 91–100%

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Evans, C.S. and Bell, E.A. (1979) Phytochemistry, 18, 1807.

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2. Treatment to male 5th instar nymphs. (2)

136

Opender Koul

AMYGDALIN

C20H27O11N (457.43)

M.p. : 220° (anhydr.) [α]20 D : –42° (H2O)

CH2OH

CN

O O H

C

O

OH

O OH

OH OH OH OH

(1)

(1) SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Synthetic diet feeding

Conc. / Dose 0.5%

Efficacy

Remarks

Feeding inhibition = 50%

Treatment to 50–75 aphids of all ages for 24 h. Concentration = EC50 value. (2)

LD50 (rats): 522 mg/kg (oral)

(3)

(1) Haworth, W.N. and Wylam, B. (1923) J. Chem Soc., 3120. (2) Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) J. Chem. Ecol., 7, 273. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

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Insect Antifeedants

ANDROGRAPHOLIDE

137

C20H30O5 (350.45) O

M.p. : 230–231° [α]26 D : –126° (AcOH)

O

HO

CH2

HO CH2OH

(2)

(1) SOURCE: Andrographis paniculata (Burm. f.) Wall. ex. Nees, king of bitters (Acanthaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Plutella xylostella (L.) (Diamondback moth)

Test Method Leaf disk no-choice test

Conc. / Dose

Efficacy

Remarks

2.5 µg/2 cm diameter leaf disk

Feeding inhibition = 50%

1. Treatment to 4th stadium larvae for 24 h. Insects pre-starved for 3 h. Concentration corresponds to FI50 value calculated from Reference 1. (1)

2. Nephotettix cincticeps (Uhler) (Green rice leafhopper)

Artificial diet feeding

1.0 ppm

Feeding inhibition = 83.4%

2. Treatment to hoppers for 24 h. (3)

(1) Hermawan, W., Nakajima, S., Tsukuda, R., Fujisaki, K., and Nakasuji, F. (1997) Appl. Entomol. Zool., 32, 551. (2) (1982) Dictionary of Organic Compounds, Vol. 1, Chapman & Hall, New York, p. 351. (3) Widiasta, I.N., Hermawan, W., Oya, S., Nakajima, S., and Nakasuji, F. (1997) Appl. Entomol. Zool., 32, 561.

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138

Opender Koul

ANGELICIN

C11H6O3 (186.17)

O

O

M.p. : 138–139.5°

O

(1, 2, 3)

(1, 2)

SOURCE: Angelica archangelica L., garden angelica (Apiaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura Fab. (Tobacco armyworm)

LD50 (rats): 322 mg/kg (oral)

Test Method

Conc. / Dose

Efficacy

Remarks

Leaf disk nochoice test

1000 ppm

Feeding ratio = 4%

Treatment to 3rd instar larvae. Activity ratio between 0 and 20% considered high active value. (3)

Artificial diet feeding

616 ppm

Feeding inhibition = 50%

Treatment to 4th instar larvae prestarved for 4 h. Treatment given for 48 h. Concentration = FI50 value. (4)

(5)

(1) Spath, E. and Pailer, M. (1934) Ber., 67, 1212; (1935) Ber., 68, 943. (2) Spath, E. and Pesta, O. (1934) Ber., 67, 853. (3) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701. (4) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem., 37, 1435. (5) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

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Insect Antifeedants

8α-ANGELOYLOXYCOSTUNOLIDE

139

C20H26O4 (330.42)

Only spectral data given

O

O CH2 O O

(1)

(1)

SOURCE: Tanacetum argenteum (Lam.) Willd., tansy (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Artificial diet feeding

Efficacy

Remarks

0.5 µmol/g

Feeding inhibition = 37.5%

Treatment to neonate larvae.

1.0 µmol/g

Feeding inhibition = 54.9%

EC50 = 0.63 µmol/g

2.5 µmol/g

Feeding inhibition = 97.69%

(1)

(1) Goren, N., Tahtasakal, E., Pezzuto, J.M., Cordell, G.A., Schwarz, B., and Proksch, P. (1994) Phytochemistry, 36, 389.

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140

Opender Koul

5α-ANGELOYLOXYSILPHINEN-3-ONE

C20H28O3 (316.42)

Oil [α]D : –59.2° (CHCl3)

O

O

O

(1)

(1) SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera littoralis (Boisd.) (Eygyptian cotton leaf worm)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

1. Treatment to 6th instar larvae.

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Choice feeding assay

>150 nmol/cm2

Feeding deterrence = 50.0%

2. Treatment to adults.

3. Myzus persicae (Sulzer) (Green peach aphid)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

3. Treatment to apterous adult aphids.

4. Rhopalosiphum padi (L.) (Cereal aphid)

Choice feeding assay

~190 nmol/cm2

Feeding deterrence = 50.0%

4. Treatment to apterous adult aphids.

5. Sitobion avenae (Fab.) (Grass aphid)

Choice feeding assay

31.6 nmol/cm2

Feeding deterrence = 50.0%

5. Treatment to apterous adult aphids.

6. Diuraphis noxia (Mordvilko) (Wheat aphid)

Choice feeding assay

>150 nmol/cm2

Feeding deterrence = 50.0%

6. Treatment to apterous adult aphids. Concentrations = EC50 values. (1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.

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Insect Antifeedants

ANGULATUEOID–G

141

C33H36O9 (552.62)

O

Only spectral data given

OH

O

H OH

O O

O OAc

(1)

(1)

SOURCE: Celastrus angulatus Maxim., bittersweet tree (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Plutella xylostella (L.) (Diamondback moth)

Leaf disk nochoice test

100 ppm

Feeding inhibition = 87.7%

1. Treatment to larvae.

2. Aulacophora femoralis (Motsch.) (Leaf beetle)

Leaf disk nochoice test

100 ppm

Feeding inhibition = 73.2%

2. Treatment to beetles.

(1) Dagang, Wu, Jikai, L., and Chunquan, C. (1992) Phytochemistry, 31, 4219.

© 2005 by CRC Press LLC

(1)

142

Opender Koul

ANGUSTONE–A

C25H26O6 (422.48) HO

M.p. : 159–160°

O

OH

O

OH

HO

(1, 2)

(1)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Costelytra zealandica (White) (Scarab beetle)

Synthetic diet disk feeding

200 µg/ml

Feeding inhibition = 69%

1. Treatment to 24-h starved 3rd instar larvae for 24 h. Percentage feeding inhibition calculated from Reference 2. (2)

2. Heteronychus arator Fab. (Pasture scarab beetle)

Synthetic diet disk feeding

200 µg/ml

Feeding inhibition = 43.0%

2. Treatment to 24-h starved 3rd instar larvae for 24 h. Data calculated from Reference 3. (3)

(1) Lane, G.A. and Newman, R.H. (1987) Phytochemistry, 26, 295. (2) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) J. Chem. Ecol., 11, 1713. (3) Lane, G.A., Sutherland, O.R.W., and Skipp, R.A. (1987) J. Chem. Ecol., 13, 771.

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Insect Antifeedants

ANGUSTONE–B

143

C25H24O6 (420.46)

HO

M.p. : 160–161°

O

OH

O

O

HO

(1, 2)

(1)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Synthetic diet disk feeding

Conc. / Dose

Efficacy

Remarks

20 µg/ml

Feeding inhibition = 49.0%

100 µg/ml

Feeding inhibition = 64.0%

Treatment to 24-h starved 3rd instar larvae for 24 h. Percentage feeding inhibition calculated from Reference 2. (2)

(1) Lane, G.A. and Newman, R.H. (1987) Phytochemistry, 26, 295. (2) Lane, G.A., Sutherland, O.R.W., and Skipp, R.A. (1987) J. Chem. Ecol., 13, 771.

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144

Opender Koul

ANGUSTONE–C

C25H24O6 (420.46) O

M.p. : 170–180°

O

OH

O

OH

HO

(1, 2)

(1)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Synthetic diet disk feeding

Conc. / Dose 20 µg/ml

Efficacy

Remarks

Feeding inhibition = 44.0%

Treatment to 24-h starved 3rd instar larvae for 24 h. Percentage feeding inhibition calculated from Reference 2. (2)

(1) Lane, G.A. and Newman, R.H. (1987) Phytochemistry, 26, 295. (2) Lane, G.A., Sutherland, O.R.W., and Skipp, R.A. (1987) J. Chem. Ecol., 13, 771.

© 2005 by CRC Press LLC

Insect Antifeedants

ANTHOTHECOL

145

C28H32O7 (480.56)

M.p. : 225° [α]20 D : –63° (CHCl3)

O AcO

O O

O OH

(1, 2)

(1, 2) SOURCE: Khaya anthotheca (Welw.) CDC, khaya wood (Meliaceae)

(2)

ACTIVITY PROFILE Test Insect Ostrinia nubilalis Hubner (European corn borer)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

50 µg/g

Feeding inhibition = 80.0%

Treatment to neonate larvae for 48 h.

500 µg/g

Feeding inhibition = 91.0%

Data calculated from Reference 3. (3)

(1) Kubo, I. and Klocke, J.A. (1981) Colloques Inst. Nat. Recherches Agric., 7, 117. (2) (1982) Dictionary of Organic Compounds, Vol. 1, Chapman & Hall, New York, p. 381. (3) Arnason, J.T., Philogene, B.J.R., Donskov, N., and Kubo, I. (1987) Entomol. Exp. Appl., 43, 221.

© 2005 by CRC Press LLC

146

Opender Koul

ANTHRANILIC ACID

C7H7O2N (137.14)

M.p. : 144–148°

COOH

NH2

(1)

(1)

SOURCE: Alchornea triplinervia (Spreng.) Muell. Arg., tapia (Euphorbiaceae)

(1)

ACTIVITY PROFILE Test Insect Anthonomus grandis Bohem. (Boll weevil)

LD50 (mice): 1400 mg/kg (oral)

Test Method

Conc. / Dose

Synthetic diet feeding

10 mg/4 cm2

Feeding ratio = 12

Treatment to freshly emerged boll weevils.

20 mg/4 cm2

Feeding ratio = 11

30 mg/4 cm2

Feeding ratio = 6

Feeding ratio based on treated/control values. Total feeding inhibition value = 0 and >100 value denotes attraction. (1)

Efficacy

Remarks

(2)

(1) Miles, D.H., Hankinson, B.L., and Randle, S.A. (1985) Proc. ACS Symp. Ser., 276, 469. (2) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

ANTHRAQUINONE-2-ALDEHYDE

147

C15H8O3 (236.21)

M.p. : 188–191°

O CHO

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk assay choice test

0.75 µmol/cm2

Efficacy

Remarks

Feeding deterrence = 50%

Treatment to 3rd instar larvae for 6 h. Concentration = ED50 value. (1)

(1) Morimoto, M., Tanimoto, K., Sakatani, A., and Komai, K. (2002) Phytochemistry, 60, 163.

© 2005 by CRC Press LLC

148

Opender Koul

APHANASTATIN (Trichilin E)

C35H46O13 (674.74)

O

20

OH

AcO

M.p. : 269–271° [α]D : –38.9° (Py/CH3OH)

O

HO O

O AcO

OH

OCO

(1)

(1, 2) SOURCE: Melia azedarach L., chinaberry (Meliaceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice test

Test Insect

Efficacy

Remarks

200 ppm

Feeding inhibition = Threshold level

1. Treatment to 3rd instar larvae for 6–24 h, during which period 50% of one of the disks was consumed.

200 ppm

Feeding inhibition = Threshold level (2)

(1) Polonsky, J., Varon, Z., Arnoux, B., Pascard, C., Pettit, G.R., Schmidt, J.H., and Lang, L.M. (1978) J. Am. Chem. Soc., 100, 2575. (2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

Insect Antifeedants

ARCHANGELOLIDE

149

C29H40O10 (548.63)

M.p. : 109–112° [α]D : –120.2° (MeOH)

OAc

CO.O

OOC

O OAc O

(3)

(1, 2) SOURCE: Laserpitium archangelica Wulf., laserwort (Apiaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

1.0%

Feeding deterrence coefficient = 44 (adults)

1. Treatment given to adults. (2)

2. Tribolium confusum Jacq. Duv. (Confused flour beetle)

Wafer disk test

1.0 %

Feeding deterrence coefficient = 49 (adults) 80 (larvae)

2. Treatment given to both adults and larvae. (2)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

1.0%

Feeding deterrence coefficient = 52 (larvae)

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200. (2)

(1) Holub, M. and Samek, Z. (1973) Collect. Czech. Chem. Commun., 38, 731. (2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243. (3) Holub, M., Budesinsky, M., Smitalova, Z., and Saman, D. (1984) Tetrahedron Lett., 25, 3755.

© 2005 by CRC Press LLC

150

Opender Koul

ARCTOLIDE

C17H20O6 (320.34)

M.p. : 144–145° [α]D : +64.1° (MeOH)

H

O

AcO

O

CH2

O

OH CH2

(1, 2)

(1, 2) SOURCE: Arctotis grandis Thumb., African daisy (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius L. (grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 95.1 (adults)

1. Treatment given to adults. (2)

2. Tribolium confusum Jacq. Duv. (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 145.1 (adults) 154.4 (larvae)

2. Treatment given to both adults and larvae. (2)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 170.8 (larvae)

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200. (2)

(1) Samek, Z., Holub, M., Grabarczyk, H., and Drozdz, B., (1977) Collect. Czech. Chem. Commun., 42, 2217. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk. Inst. Ochr. Roslin, 25, 91.

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Insect Antifeedants

ARECOLINE

151

C8H13O2N (155.19)

B.p. : 209° n20 D

: 1.4302

N

COO

(1, 2)

(1, 2, 3) SOURCE: Commercial sample

(3)

ACTIVITY PROFILE Test Insect Phormia regina Meigen (Blow fly)

Test Method Sucrose solution feeding

Conc. / Dose 10 mM

Efficacy

Remarks

Feeding inhibition = 51% (after 6 h)

Treatment to 2-, 4-, and 6-day-old adults, pre-starved for 24 h. (3)

Feeding inhibition = 63% (after 24 h)

LD50 (mice): 100 mg/kg (s.c.) (1) (2) (3) (4)

Johns, E. (1891) Arch. Pharm., 229, 673. Chemnitius, F. (1928) J. Prakt. Chem., 117, 147. Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299. Burrows, R.B. (1973) Progr. Drug Res., 17, 108.

© 2005 by CRC Press LLC

(4)

152

Opender Koul

ARGOPHYLLIN–A

C20H28O7 (380.44) O

M. p.: 190–192° [α]D22 : –157° (CHCl3)

O O OH HO

CH2 O O

(1, 2)

(1, 2, 3)

SOURCE: Helianthus annuus L., sunflower (Asteraceae)

(1, 2)

ACTIVITY PROFILE Test Insect Diabrotica virgifera virgifera LeConte (Western corn rootworm)

Test Method

Conc. / Dose

Leaf disk test

40 µg/1.5 cm2

Efficacy

Remarks

Feeding inhibition = 77% approximately in 24 h.

Treatment to adults. Data based on consumption of 32% after 5 h and 23% after 24 h in comparison to controls. (2)

Calculated from Reference 2.

(1) Melek, F.R., Gage, D.A., Gershenzon, J., and Mabry, T.J. (1985) Phytochemistry, 24, 1537. (2) Mullin, C.A., Alfatafta, A.A., Harman, J.L., Everett, S.L., and Serino, A.A. (1991) J. Agric. Food Chem., 39, 2293. (3) Watanabe, K., Ohno, N., Yoshioka, H., Gershenzon, J., and Mabry, T.J. (1982) Phytochemistry 21, 709

© 2005 by CRC Press LLC

Insect Antifeedants

ARISTOLOCHIC ACID

153

C17H11O7N (341.28)

M.p. : 281–286° (dec.)

COOH

O

NO2

O

OCH3

(1)

(1)

SOURCE: Aristolochia albida Duch., Nigerian climber (Aristolochiaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura Fab. (Tobacco armyworm)

LD50 (rats): 184 mg/kg (oral)

Test Method Leaf disk choice bioassay

Conc. / Dose

Efficacy

500 ppm

Feeding inhibition index = 0

100 ppm

Feeding inhibition index = 3.73

50 ppm

Feeding inhibition index = 19.96

Remarks 1. Treatment to 4-day-old larvae for 1 day. Antifeedant index value below 20 considered highly deterrent. (1)

(2)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1993) J. Agric. Food Chem., 41, 669. (2) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

154

Opender Koul

ARTECANIN (Chrysartemin B)

C15H18O5 (278.30) OH

M.p. : 244–245° [α]23 D : +26.6° (C2H5OH)

O

O H

CH2

O

O

(1, 2)

(1, 2) SOURCE: Chrysanthemum macrophyllum W & K, chrysanthemum (Asteraceae)

(3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

8.0 mg/cm3

Feeding deterrence coefficient = 51–100 (adults)

1. Treatment given to adults. (3)

2. Tribolium confusum Jacq. Duv. (Confused flour beetle)

Wafer disk test

8.0 mg/cm3

Feeding deterrence coefficient = 101–150 (adults) 101–150 (larvae)

2. Treatment given to both adults and larvae. (3)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

8.0 mg/cm3

Feeding deterrence coefficient = 101–150 (larvae)

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200. (3)

(1) Lee, K.H., Simpson, R.F., and Geissman, T.A. (1969) Phytochemistry, 8, 1515. (2) Bhadane, N.R. and Shafizadeh, F. (1975) Phytochemistry, 14, 2651. (3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Dorzdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin, 24, 27.

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Insect Antifeedants

ARTEMISININ

155

C15H22O5 (282.34)

M. p.: 156–157° [α]17 D : 66.3° (neat)

H

O

H

O O O H O

(1)

(1, 2) SOURCE: Artemisia annua L., annual wormwood (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Diabrotica virgifera virgifera LeConte (Western corn rootworm)

Test Method

Conc. / Dose

Leaf disk test

40 µg/1.5 cm2

Efficacy

Remarks

Feeding inhibition = 59% approximately in 24 h.

Treatment to adults. Data based on consumption of 32% after 5 h and 41% after 24 h in comparison to controls. (2)

Calculated from Reference 2.

80 µg/1.5 cm2

Feeding inhibition = 60% approximately in 24 h. Calculated from Reference 2.

LD50 (mice): 5105 mg/kg (oral)

Treatment to adults. Data based on consumption of 20% after 5 h and 40% after 24 h in comparison to controls. (2)

(3)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Mullin, C.A., Mason, C.H., Chou, J., and Linderman, J.R. (1992) In C.A. Mullin and J.G. Scott (eds.), Molecular Mechanisms of Insecticide Resistance: Diversity Among Insects, ACS Symp. Ser. 505, Washington, D.C., pp. 288–308. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

156

Opender Koul

ASIATIC ACID

C30H48O5 (488.71)

M.p. : 300–305°

COOH HO

HO HO

(1, 2)

(2)

SOURCE: Shorea robusta Gaertn. f., sal (Dipterocarpaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Oxya fuscovittata (Marsh.) (Rice grasshopper)

Test Method Whole leaf application from Coix lachryma leaves

Conc. / Dose 0.5%

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to overnight-starved 6th instar nymphs for 24 h. (3)

(1 ml/g) of leaf

(1) Purushothman, K.K., Saraswathy, A., and Sasikala, E. (1988) Indian Drugs, 26, 146. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London. (3) Sanjayan, K.P. and Dhang, P.P. (1993) J. Appl. Ent., 115, 506.

© 2005 by CRC Press LLC

Insect Antifeedants

ASIMICIN (Annonastatin)

157

C37H66O7 (622.92)

OH

O

M.p. : 70–72° [α]D : +21.8° (MeOH)

O

O OH

O

OH

(1, 2, 3)

(1, 2) SOURCE: Rollinia sylvatica (A. St.-Hill) Mart., araticum (Annonaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Whole leaf application

Conc. / Dose 0.5 ppm

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to beetles. (2)

(1) Cortes, D. et al. (1991) Tetrahedron Lett. 32, 6133. (2) Mikolajczak, K.L., McLaughlin, J.L., and Rupprecht, J.K. (1986) U.S. Patent Appl. 860351, 28 pp. (3) Rupprecht, J.K., Chang, C.J., Cassady, J.M., and McLaughlin, J.L. (1986) Heterocycles, 24, 1197.

© 2005 by CRC Press LLC

158

Opender Koul

ATALANTIN

C27H32O9 (500.54) O

M.p. : 184–185° [α]D22 : +84.4° (CHCl3)

O OCH3

O

O

O

O OH O

(1, 2)

(1, 2, 3)

SOURCE: Severinia buxifolia (Poir.) Tenore., Chinese box orange (Rutaceae)

(1)

ACTIVITY PROFILE Test Insect Plutella xylostella (L.) (Diamondback moth)

Test Method

Conc. / Dose

Leaf disk choice test

0.0625%

Efficacy Feeding inhibition = 50%

Remarks Treatment to 3rd instar larvae. Concentration = EC50 value. (1)

(1) Wu, T.S., Leu, Y.L., Chan, Y.Y., Wu, P.L., Kuoh, C.S., Wu, S.J., and Wang, Y. (1997) Phytochemistry, 45, 1393. (2) Basu, D. and Basu, S.C. (1972) J. Org. Chem., 37, 3035. (3) Dreyer, D.L., Bennett, R.D., and Basa, S.C. (1976) Tetrahedron, 32, 2367.

© 2005 by CRC Press LLC

Insect Antifeedants

ATROPINE

159

C17H23O3N (289.38)

M.p. : 114–116°

N

CH2OH

OOCCH

(1, 2, 3)

(1, 2)

SOURCE: Commercial sample

(3)

ACTIVITY PROFILE Test Insect Phormia regina Meigen (Blow fly)

Test Method Sucrose solution feeding

Conc. / Dose 10 mM

Efficacy

Remarks

Feeding inhibition = 86.0% after 6 h and 83.0% after 24 h.

Treatment to 2-, 4-, and 6-day-old adults pre-starved for 24 h. (3)

LD50 (rats): 750 mg/kg (oral) (1) (2) (3) (4)

Chemnitius, F. (1927) J. Prakt. Chem., 116, 276. Schwenker, G., Premtzell, W., Gassuer, U., and Gerber, R. (1966), Ber. 99, 2407. Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299. Cahen, R.L. and Tvede, K.M. (1952) J. Pharmacol. Exp. Ther., 105, 166.

© 2005 by CRC Press LLC

(4)

160

Opender Koul

AZADIRACHTIN–A

C35H44O16 (720.72)

M.p. : 155–158° (165°) [α]20 D : –65.4° (CHCl3)

COOCH3

O O

O

OH

OH

O

O OH

AcO H3COOC

O

H

O

(1, 2)

(1, 2) SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Efficacy

Remarks 1. Treatment to 24- to 36-h-old pre-starved final stadium larvae. Bioassay terminated after the larvae had eaten approximately 50% of one of the disks. (3) Treatment given to larvae. (4)

Glass fiber disk choice test

1.0 ppm

Feeding deterrence = 99.0%, calculated from Reference 3

No-choice test

1.0 ppm

Feeding deterrence = 90.0%, calculated from Reference 3

Artificial diet feeding

10.0 ppm

Feeding deterrence = 100.0%

Foiliage spray

0.06 ppm

Feeding deterrence = 50.0%

Treatment for larvae. (5)

Foiliage spray

600 ppm

Feeding deterrence = 100.0%

Treatment for larvae. (6)

(1) Kraus, W., Bokel, M., Klenk, A., and Pohnl, H.D. (1985) Tetrahedron Lett., 26, 6435. (2) Kraus, W., Bokel, M., Bruhn, A., Cramer, R., Klaiber, I., Klenk, A., Nagl., G., Pohnl., H., Sadlo, H., and Vogler, B. (1987) Tetrahedron, 43, 2817. (3) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149. (4) Meisner, J., Ascher, K.R.S., Aly, R., and Warthen, J.D. Jr. (1981) Phytoparasitica, 9, 27. (5) Plieger, D. and Muckenstrum, B. (1987) Tetrahedron Lett., 28, 1519.

© 2005 by CRC Press LLC

Insect Antifeedants

161

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE Test Insect 2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

3. Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Efficacy

Remarks 2. Treatment to 24- to 36-h-old pre-starved final stadium larvae. Bioassay terminated after the larvae had eaten approximately 50% of one of the disks. (3)

Glass fiber disk choicetest.

1.0 ppm

Feeding deterrence = 90.0%, calculated from Reference 3

No-choice test

1.0 ppm

Feeding deterrence = 84.3%, calculated from Reference 3

Leaf disk test

50.0 ppm

Feeding deterrence = 43.0%

Treatment to larvae. (7)

Glass fiber disk choicetest.

1.0 ppm

Feeding deterrence = 77.0%, calculated from Reference 3

3. Treatment to 24- to 36-h-old pre-starved final stadium larvae.

(6) Klocke, J.A. and Barnby, M.A. (1989) In C.H. Chou and G.R. Walls (eds.) Phytochemical Ecology: Allelochemicals, Mycotoxins and Insect Pheromones and Allomones, Inst. of Botany, Academia Sinica Monograph Series No. 9, Taipei, Taiwan. (7) Raffa, K.F. (1987) J. Econ. Entomol., 80, 384.

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162

Opender Koul

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE Test Insect

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Test Method

Conc. / Dose

Efficacy

Remarks

No-choice test

1.0 ppm

Feeding deterrence = 88.9%, calculated from Reference 3

Bioassay terminated after the larvae had eaten approximately 50% of one of the disks. (3)

Artificial diet feeding

0.07 ppm

Feeding deterrence = 50.0%.

Concentration = EC50 value. (8)

Glass fiber disk choice test.

1.0 ppm

Feeding deterrence = 85.0%, calculated from Reference 3

4.Treatment to 24- to 36-h-old pre-starved final stadium larvae. (3)

(8) Yamasaki, R.B. and Klocke, J.A. (1987) J. Agric. Food Chem., 35, 467.

© 2005 by CRC Press LLC

Insect Antifeedants

163

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE Test Insect 5. Spodoptera litura Fab. (Tobacco armyworm)

6. Peridroma plorans (Cutworm)

Test Method

Conc. / Dose

Leaf disk choice test

Artificial diet feeding

Efficacy

Remarks

0.015 µg/cm2

Feeding deterrence = 50.0%

5. Treatment to 5th instar larvae for 6 h. Concentration = EC50 value. (9)

50 ppm

Feeding deterrence = 37.0%

Treatment to freshly moulted 4th instar larvae for 24 h. (10)

0.4 ppm

Feeding deterrence = 50.0%

6. Treatment to larvae. Concentration = EC50 value. (11)

(9) Koul, O., Shankar, J.S., and Kapil, R.S. (1996) Entomol. Exp. Appl., 79, 43. (10) Ramachandran, R., Mukherjee, S.N., and Sharma, R.N. (1989) Entomol. Exp. Appl., 51, 29. (11) Champagne, D.E., Isman, M.B., and Towers, G.H.N. (1989) ACS Symp. Ser. 387, Am. Chem. Soc., Washington, D.C., pp. 95–109.

© 2005 by CRC Press LLC

164

Opender Koul

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

7. Peridroma saucia (Hubner) (Variegated cutworm)

Leaf disk choice test

2.4 ppm

Feeding deterrence = 50.0%

7. Treatment to 4th instar larvae for 6 h. Concentration = EC50 value. (12)

8. Earias insulana Boisd. (Spotted bollworm)

Artificial diet feeding

50.0 ppm

Feeding deterrence = 100.0%

8. Treatment to larvae. (13)

9. Ostrinia nubilalis (Hubner) (European corn borer)

Leaf disk test

24.0 ppm

790 ppm

Feeding deterrence = 50.0%. Data calculated on the basis of protection concentration (PC). Feeding inhibition = 95%

9. Treatment to 3rd instar larvae up to 72 h. Concentration = PC50 and PC95 value. (14)

(12) Isman, M.B., Koul, O., Luczynski, A., and Kaminski, J. (1990) J. Agric. Food Chem., 38, 1406. (13) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) Proc. 2nd Int. Neem Conf., GTZ, Eschborn, Germany, pp. 181–198. (14) Arnason, J.T., Philogene, B.J.R., Donskov., N., Hudon, M., McDougall, C., Fortier, G., Morand, P., Gardner, D., Lambert, J., Morris, C., and Nozzolillo, C. (1985) Entomol. Exp. Appl., 38, 29.

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Insect Antifeedants

165

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

10. Pieris brassicae L. (Large white butterfly)

Systemic

30.0 ppm

Feeding deterrence = 56.0%

10. Treatment to first instar for 72 h. (15)

11. Achaea janata (L.) (Castor semilooper)

Leaf disk test

1.0 ppm

Feeding deterrence = 54.0%

10.0 ppm

Feeding deterrence = 74.0%

11. Treatment to freshly molted 4th instar larvae for 24 h. (10)

0.0014%

Feeding deterrence = 50.0%

12. Epilachna varivestis Muls. (Mexican bean beetle)

Bean half leaf test

(15) Arpaia, S. and Van Loon, J.J.A. (1993) Entomol. Exp. Appl., 66, 39.

© 2005 by CRC Press LLC

12. Treatment to 4th instar larvae for up to 24 h. Concentration = EC50 value. (13)

166

Opender Koul

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE Test Insect

Test Method

13. Diabrotica undecimpunctata howardi Barber (Spotted cucumber beetle)

Spray

14. Acalymma vittatum (Fab.) (Striped cucumber beetle)

Spray

Conc. / Dose 100 ppm

Efficacy Feeding deterrence = 98.0%.

Remarks 13. Treatment to beetles. (16)

100 ppm

Feeding deterrence = 98.0%.

14. Treatment to beetles. (16)

15. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Spray

600 ppm

No feeding deterrence

15. Treatment to beetles.

(16) Reed, D.K., Warthen, J.D. Jr., Uebel, E.C., and Reed, G.L. (1982) J. Econ. Entomol., 75, 1109.

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(16)

Insect Antifeedants

167

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE Test Insect 16. Myzus persicae (Sulzer) (Green peach aphid)

Test Method Artificial diet feeding

Conc. / Dose 100 ppm

Efficacy Feeding deterrence = 80.0%

Remarks 16. Treatment to adults. (17)

17. Chaetosiphon fragaefolii (Cockerell) (Strawberry aphid)

Systemic

300 ppm

Feeding deterrence = 30.0%

Treatment to adults. (18)

18. Rhopalosiphum padi (L.) (Bird cherry aphid)

Leaf disk choice test

119.5 ppm

Feeding deterrence = 50.0%

17. Treatment to adult aphids. Concentration = EC50 value. (19)

Leaf disk choice test

250 ppm

Feeding deterrence = 50.0%

Systemic

500 ppm

Feeding deterrence = 18.0%

18. Treatment to adult aphids and data assessed after 25 m of probing. (20)

(17) Nisbet, A.J., Woodford, J.A.T., and Strang, R.H.C. (1992) In S.B.J. Menken, J.H. Viser, and P. Harrewiju (eds.), Proc. 8th Int. Symp. Insect-Plant Relationships, Kluwer Acad. Publishers, Dordrecht, The Netherlands, pp. 424. (18) Nisbet, A.J., Woodford, J.A.T., Strang, R.H.C., and Conolly, J.D. (1993) Entomol. Exp. Appl., 68, 87. (19) Lowery, D.T. and Isman, M.B. (1993) J. Chem. Ecol., 19, 1761. (20) West, A.J. and Mordue (Luntz), A.J. (1992) Entomol. Exp. Appl., 62, 75.

© 2005 by CRC Press LLC

168

Opender Koul

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE Test Method

Conc. / Dose

19. Brevicoryne brassicae (L.) (Cabbage aphid)

Leaf disk choice test

20. Rhodnius prolixus L. (Assassin bug)

21. Schistocerca gregaria (Forska.) (Desert locust)

Test Insect

Efficacy

Remarks

10.7 ppm

Feeding deterrence = 50.0%

19. Treatment to 2nd instar aphids. Concentration = EC50 value. (21)

Blood meal feeding

25.0 ppm

Feeding deterrence = 50.0%

Filter paper disk test

0.008 ppm

Feeding deterrence = 50.0% Feeding deterrence = 95.0% Feeding deterrence = 100.0%

20. Treatment to 4th instar larvae. Concentration = EC50 value. (22) 21. Treatment to various nymphal stages by various workers. Range of potential activity between 0.01 and 0.05 ppm. (23–26) Foliage spray. (27)

0.005 ppm 0.01 ppm

Spray

(21) (22) (23) (24) (25) (26) (27)

1.0 ppm

Feeding deterrence = 50.0%

Koul, O., Shankar, J.S., and Mehta, N. (1997) Ind. J. Expt. Biol., 35, 994. Garcia, E.S. and Rembols, H. (1984) J. Insect Physiol., 30, 939. Haskel, P.T. and Mordue (Luntz), A.J. (1969) Entomol. Exp. Appl., 12, 591. Morgan, E.D. (1981) Proc. Ist Int. Neem Conf., GTZ, Eschborn, Germany, pp. 43–52. Butterworth, J.H. and Morgan, E.D. (1968) J. Chem. Soc. Chem. Commun., 23. Butterworth, J. H. and Morgan, E.D. (1971) J. Insect Physiol., 17, 969. Nasiruddin, M. and Mordue (Luntz), A.J. (1994) Entomol. Exp. Appl., 70, 247.

© 2005 by CRC Press LLC

Insect Antifeedants

169

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE Test Insect 22. Locusta migratoria (L.) (Migratory locust)

23. Melanoplus sanguinipes (Fab.) (Migratory grasshopper)

Test Method

Conc. / Dose

Fiber glass disk test

Efficacy

Remarks

100 ppm

Feeding deterrence = 50.0%

22. Treatment to nymphs Concentration = EC50 value. (28)

Filter paper disk test

100 ppm

Feeding deterrence = 50.0%

Treatment to larvae. Concentration = EC50 value. (29)

Artificial diet feeding

1000 ppm

No feeding deterrence

23. Treatment to various nymphal stages. (30) EC50 considered to be >1000 ppm. (31)

24. Eyprepocnemis plorans (Charpentier) (Grasshopper)

Topical treatment to leaves/disks

0.01 ppm 0.1 ppm

Feeding inhibition = 54% = 85%

24. Treatment to nymphs.

(28) Cottee, P.K., Bernays, E.A., and Mordue (Luntz), A.J. (1988) Entomol. Exp. Appl., 46, 241. (29) Pradhan, S., Jotwani, M.G., and Rai, B.K. (1962) Indian Farming, 12, 7. (30) Mulkern, G.B. and Mongolkiti, S. (1975) Acrida, 4, 95. (31) Mordue (Luntz), A.J. and Blackwell, A. (1993) J. Insect Physiol., 39, 903. (32) Ascher, K.R.S., Streloke, M., Schmidt, G.H., and Warthen, J.D. Jr. (1989) Phytoparasitica, 17, 167.

© 2005 by CRC Press LLC

(32)

170

Opender Koul

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE Test Insect

Test Method

25. Phyllotreta striolata (Fab.) (Flea beetle)

Cotyledon painting

26. Coptotermes formosanus Shiraki (Formosan subterranean termite)

27. Reticulitermes speratus Kolbe (Subterranean termite)

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding deterrence = 54.0%.

25. Treatment to adult beetles for 24 h. (33)

Filter paper disk test

100 ppm

Feeding deterrence = 50.0% in terms of paper mass loss.

26. Treatment to workers for 10 days. Data calculated from Reference 34. (34)

Paper disk no-choice test

2157 ppm

Feeding deterrence = 50.0% Feeding deterrence = 95.0%

27. Treatment to 3rd instar larvae based on size over 25 days. Concentrations = EC50 and EC95 respectively. (35)

65,293 ppm

(33) Meisner, J. and Mitchell, B.K. (1982) Z. Pflanzenkrank. Pflanzen., 89, 463. (34) Grace, J.K. and Yates, J.R. (1992) Trop. Pest. Manag., 38, 176. (35) Serit, M., Ishida, M., Hagiwara, N., Kim, M., Yamamoto, T., and Takahashi, S. (1992) J. Chem. Ecol., 18, 593.

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Insect Antifeedants

171

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE Test Insect 28. Pericallia ricini (Fab.) (Tiger moth)

29. Oxya fuscovittata (Grasshopper)

LD50 (rats): >5000 mg/kg (oral)

Test Method Leaf disk dual-choice test

Leaf disk dual-choice test

Conc. / Dose 1 µg/cm2 10 µg/cm2 1 µg/cm2 10 µg/cm2

Efficacy

Remarks

Feeding deterrence = 79.2% Feeding deterrence = 87.5%

28. Treatment to 3rd instar larvae for 24 h. (36)

Feeding deterrence = 74.2% Feeding deterrence = 87.2%

29. Treatment to 3rd instar larvae for 24 h. (36)

(37)

(36) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., and Gopalakrishnan, G. (1996) J. Chem Ecol., 18, 593. (37) Koul, O. (2003) In M.M. Srivastava and S. Srivastava (eds.), Recent Trends in Chemistry, Discovery Publishing House, New Delhi, pp. 248–265.

© 2005 by CRC Press LLC

172

Opender Koul

AZADIRACHTIN–B

C33H42O14 (662.68)

M.p. : 204–206°

COOCH3 HO

H

O

OH

11 O

1 3

O

O OH

O H H3COOC

O

O

(1)

(1)

SOURCE: Azadirachta indica A. Juss. neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura Fab. (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 50 ppm 10 ppm 5 ppm 1 ppm

2. Rhodnius prolixus L. (Assassin bug)

Blood meal feeding

26.0 µg/ml

Efficacy

Remarks

Feeding deterrence = 81.9% Feeding deterrence = 78.4% Feeding deterrence = 77.0% Feeding deterrence = 54.5%

1. Treatment to 3rd instar freshly moulted larvae for 24 h. EC50 = 0.85 ppm calculated from Reference 2. (2)

Feeding deterrence = 50.0%

2. Treatment to 4th instar nymphs. Concentration = EC50 value. (3)

(1) Rembold, H., Forster, H., and Sonnenbichler, J. (1987) Z. Naturforsch., 42C, 4. (2) Govindachari, T.R., Suresh, G., and Ganeshwar Prasad, K. (1994) Pestic. Res. J., 6, 20. (3) Garcia, E.S., Azambuja, P., Forster, H., and Rembold, H. (1984) Z. Naturforsch., 39C, 1155.

© 2005 by CRC Press LLC

Insect Antifeedants

AZADIRACHTIN–D

173

C34H44O14 (676.71)

M.p. : 170–176°

COOCH3

O O

O

Only spectral data given

OH

OH

[α]D27 : –1.27° (CHCl3) (for 11 epimer)

O

O

O

OH

AcO H

O

(1,3)

(1) SOURCE: Azadirachta indica A. Juss. neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura Fab. (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 50 ppm 10 ppm 5 ppm 1 ppm

No-choice test

50 ppm 10 ppm 5 ppm 1 ppm

Efficacy

Remarks

Feeding deterrence = 81.9% Feeding deterrence = 78.4% Feeding deterrence = 77.0% Feeding deterrence = 54.5%

Treatment to 3rd instar freshly moulted larvae for 24 h. EC50 = 1.3 ppm calculated from Reference 2. (2)

Feeding deterrence = 36.5% Feeding deterrence = 33.0% Feeding deterrence = 16.8% Feeding deterrence = 16.8%

Treatment to 3rd instar freshly moulted larvae for 24 h. EC50 = 65.0 ppm calculated from Reference 2. (2)

(1) Rembold, H. (1990) ACS Symp. Ser. 387, Am. Chem. Soc., Washington, D.C., pp. 150–163. (2) Govindachari, T.R., Suresh, G., and Ganeshwar Prasad (1994) Pestic. Res. J., 6, 20. (3) Ramji, N., Venkatakrishnan, K., and Madyastha, K.M. (1998) Phytochemistry, 49, 265.

© 2005 by CRC Press LLC

174

Opender Koul

AZADIRACHTIN–H

C33H42O14 (662.68)

M.p. : 258–261° [α]D25 : –33.3° (CHCl3)

O

H O

O

OH

OH

O

O OH

AcO H3COOC

O

H

O

(1)

(1) SOURCE: Azadirachta indica A. Juss. neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura Fab. (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 50 ppm 10 ppm 5 ppm 1 ppm

No-choice test

50 ppm 10 ppm 1 ppm

Efficacy

Remarks

Feeding deterrence = 53.7% Feeding deterrence = 50.4% Feeding deterrence = 56.8% Feeding deterrence = 64.6%

Treatment to 3rd instar freshly moulted larvae for 24 h. EC50 could not be calculated from the recorded data. (2)

Feeding deterrence = 30.2% Feeding deterrence = 24.1% Feeding deterrence = 18.8%

Treatment to 3rd instar freshly moulted larvae for 24 h. EC50 = 70.0 ppm calculated from Reference 2. (2)

(1) Govindachari, T.R., Sandhya, G., and Ganesh Raj, S.P. (1992) J. Nat. Prod., 55, 596. (2) Govindachari, T.R., Suresh, G., and Ganeshwar Prasad (1994) Pestic. Res. J., 6, 20.

© 2005 by CRC Press LLC

Insect Antifeedants

AZADIRACHTIN–I

175

C32H42O12 (618.68)

O

[α] 25 D : –21.8° (CHCl3)

H O

O

M.p. : 198–200°

OH

OH

O

O

O

OH

AcO H

O

(1)

(1) SOURCE: Azadirachta indica A. Juss. neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura Fab. (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 10 ppm 1 ppm

No-choice test

50 ppm 5 ppm

Efficacy

Remarks

Feeding deterrence = 55.3% Feeding deterrence = 37.2%

Treatment to 3rd instar freshly moulted larvae for 24 h. EC50 could not be calculated from the recorded data. (2)

Feeding deterrence = 9.2% Feeding deterrence = 8.1%

(1) Govindachari, T.R., Sandhya, G., and Ganesh Raj, S.P. (1992) J. Nat. Prod., 55, 596. (2) Govindachari, T.R., Suresh, G., and Ganeshwar Prasad (1994) Pestic. Res. J., 6, 20.

© 2005 by CRC Press LLC

176

Opender Koul

AZADIRACHTOL (3-Detigloylazadirachtin B)

C28H37O13 (581.56)

Only spectral data given

COOCH3 HO

O

H

OH O

O HO H3COOC

O

OH O

(1, 2)

(3)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to 24- to 36-h-old pre-starved final stadium larvae. Bioassay terminated after the larvae had eaten approximately 50% of one of the disks. (1)

Glass fiber disk choice test

1 ppm

Feeding deterrence = 86.0%

Glass fiber disk nochoice test

1 ppm

Feeding deterrence = 38.3%

Deterrence calculated from Reference 1 for nochoice assay, which was run for 8 to 9 h.

(1) Siddiqui, S., Siddiqui, B.S., Faizi, S., and Mahmood, T. (1988) J. Nat. Prod., 51, 30. (2) Blaney, W.M., Simmonds, M.S.J., Ley S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149. (3) Ley, S.V., Denholm, A.A., and Wood, A. (1993) Nat. Prod. Rep., 10, 109.

© 2005 by CRC Press LLC

Insect Antifeedants

AZADIRADIONE

177

C28H34O5 (450.57)

M.p. : 168° [α]20 D : +35.5° (CHCl3)

O

O

O

OAc

(1)

(1) SOURCE: Azadirachta indica A. Juss. neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dual-choice test

Conc. / Dose 1 µg/cm2 5 µg/cm2 10 µg/cm2 20 µg/cm2

2. Epilachna varivestis Muls. (Mexican bean beetle)

Bean leaf choice assay

0.033%

Efficacy

Remarks

Feeding deterrence = 57.5% Feeding deterrence = 61.0% Feeding deterrence = 74.1% Feeding deterrence = 77.0%

1. Treatment to 3rd instar freshly moulted larvae for 24 h. (2)

Feeding inhibition = 50%

2. Treatment to 4th stadium larvae up to 24 h. Concentration = EC50 value. (3)

EC50 = 0.43 µg/cm2 calculated from Reference 2.

(1) Lavie, D., Levy, E.C., and Jain, M.K. (1971) Tetrahedron, 27, 3927. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari, G.N. (1995) J. Chem. Ecol., 21, 1586. (3) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC

178

Opender Koul

AZADIRONE

C28H36O4 (436.59)

Amorphous [α]D : +26° (CHCl3)

O

OAc

O

(1)

(1) SOURCE: Azadirachta indica A. Juss. neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Bean leaf choice assay

Conc. / Dose 0.66%

Efficacy

Remarks

Feeding deterrence = 50%

Treatment to 4th stadium larvae up to 24 h. Concentration = EC50 value. (2)

(1) Lavie, D., Levy, E.C., and Jain, M.K. (1971) Tetrahedron, 27, 3927. (2) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC

Insect Antifeedants

AZEDARACHIN–A

179

C33H44O11 (616.70)

Amorphous powder

O

[α]22 D : –10° (CH3OH)

OH

HO

O

O

O AcO

OH

OCO

(1)

(1) SOURCE: Melia azedarach L., chinaberry (Meliaceae) M. toosendan Sieb. et Zucc., Chinese melia (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

200 ppm or 4 µg/cm2

Threshold level for feeding deterrence

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice test

200 ppm or 4 µg/cm2

Threshold level for feeding deterrence

Test Insect

Efficacy

Remarks Treatment to 3rd instar larvae for 6–24 h, during which period 50% of one of the disks was consumed. (1, 2)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117. (2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

180

Opender Koul

AZEDARACHIN–B

C32H42O11 (602.68) O

Amorphous powder [α]D : –22° (CH3OH)

OH

HO

O

O

O AcO

OH

OCO

(1)

(1) SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Leaf disk choice test

200 ppm or 4 µg/cm2

Efficacy Threshold level for feeding deterrence

Remarks Treatment to 3rd instar larvae for 6–24 h, during which period 50% of one of the disks was consumed. (1)

(1) Zhou, J., Minami, Y., Yagi, F., Tadera, K., and Nakatani, M. (1997) Heterocycles, 45, 1718.

© 2005 by CRC Press LLC

Insect Antifeedants

AZEDARACHIN–C

181

C32H42O10 (586.68) O

HO

Only spectral data given

O

O

O AcO

OH

OCO

(1)

(1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

400 ppm or 8 µg/cm2

Threshold level for feeding deterrence

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice test

400 ppm or 8 µg/cm2

Threshold level for feeding deterrence

Test Insect

Efficacy

Remarks Treatment to 3rd instar larvae for 6–24 h, during which period 50% of one of the disks was consumed. (1)

(1) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

182

Opender Koul

AZEDARACHOL

C25H40O5 (420.59) CH2

M.p. : 231–232° [α]24 D : +20° (CHCl3)

O H O OH

H HO H HO H

(1)

(1) SOURCE: Melia azedarach L. var. japonica Makino, Japanese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Agrotis segetum Denis and Schiff. (Turnip cutworm)

Test Method

Conc. / Dose

Leaf disk choice test

500 ppm

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to larvae. (1)

(1) Nakatani, M., Takao, H., Miura, I., and Hase, T. (1985) Phytochemistry, 24, 1945.

© 2005 by CRC Press LLC

Insect Antifeedants

AZEDARALIDE

183

C15H16O4 (260.11)

Yellowish powder [α]D25 : +165° (CH3OH)

O

O

O CH2OH

(1)

(1) SOURCE: Melia azedarach L., darekh (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy Feeding inhibition = 100%

Remarks Treatment to 3rd instar larvae. (1)

(1) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., and Tadera, K. (1998) Phytochemistry, 49, 1773.

© 2005 by CRC Press LLC

184

Opender Koul

BAKKENOLIDE–A

C15H22O2 (234.34)

M.p. : 80.5–80.6° [α]D22 : +17° (CH3OH)

O

O

CH2

H

(1, 2)

(1, 2) SOURCE: Homogyne alpina (L.) Cass., alpine colts foot (Asteraceae)

(3)

ACTIVITY PROFILE Test Insect 1. Sitophilus granarius L. (Grain weevil)

Test Method Wafer disk test

Conc. / Dose 10 mg/ml

Efficacy Feeding deterrence coefficient = 140

Remarks 1. Treatment to adults. (3)

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 197 = 141

2. Treatment to Adults Larvae (3)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

4. Peridroma saucia (Hubner) (Variegated cutworm)

Leaf disk choice test

10 mg/ml

Feeding deterrence coefficient = 187

3. Treatment to larvae. (3) Data based on a 0 to 200 greater deterrence scale.

28.5 µg/cm2 57.0 µg/cm2

Feeding inhibition = 38.3% Feeding inhibition = 74.3%

4. Treatment to 5th instar larvae for 5 h. (4)

(1) Naya, K., Takagi, I., Hayashi, M., Nakamura, S., Kobayashi, M., Katsumura, S., Harmatha, J., and Samek, Z. (1968) Chem. Ind., 318. (2) Synackova, M., Novotny, L., Herout, V., and Sorm, F. (1976) Collect. Czech. Chem. Commun., 41, 2047. (3) Harmatha, J. and Nawrot, J. (1984) Biochem. Syst. Ecol., 12, 95. (4) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.

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Insect Antifeedants

BENZALDEHYDE

185

C7H6O (106.12)

M.p. : –26° B.p. : 179° n20 D

CHO

: 1.5456

(1)

(1) SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Synthetic diet feeding

Conc. / Dose 0.4%

Efficacy

Remarks

Feeding deterrence = 50%

Treatment to 50–75 aphids at random for 24 h. Concentration = EC50 value. (2)

LD50 (rats): 1300 mg/kg (oral)

(3)

(1) Vogel, A.I. (1959) Practical Organic Chemistry, Longmans, London, p. 693. (2) Dreyer, D.L., Reese, J.C., and Jones, K..C. (1981) J. Chem. Ecol., 7, 273. (3) Jenner, P.M., Hagan, E.C., Taylor, J.M., Cook, E.L., and Fitzhugh, O.G. (1964) Food Cosmetics Toxicol., 2, 327.

© 2005 by CRC Press LLC

186

Opender Koul

p-BENZOQUINONE

C6H4O2 (108.10)

M.p. : 115.7° (117°) d20 4

: 1.32

O

O

(1)

(1, 2) SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Pieris brassicae (L.) (Large white butterfly)

LD50 (rats): 130 mg/kg (oral)

Test Method

Conc. / Dose

Leaf disk nochoice test

9.3 × 10–2 M

Efficacy Feeding deterrence ratio = 32

Remarks Treatment to 2nd day 5th instar un-starved larvae. Ratio of less than 20 considered as effective feeding deterrence. (2)

(3)

(1) Underwood, H.W. Jr., and Walsh, W.L. (1936) Org. Synth., 16, 73. (2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8tth edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

15-O-BENZOYL BRUCEINE–D

187

C27H30O10 (514.53)

M.p. : 290–298° [α]22 D : +24.05° (Pyridine)

OH HO O OCO

O H

OH O

O

(1)

(1, 2) SOURCE: Soulamea amara Lam., bouati (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Leaf disk choice test

12.0 µg/cm2

Feeding deterrence = 90–100% after 2 days; 60–90% after 6 days

3.0 µg/cm2

Feeding deterrence = 60–90% after 2 days; 30–60% after 6 days

Efficacy

Remarks Treatment to 3rd instar larvae.

(2)

(1) Lee, K.H., Imakura, Y., Sumida, Y., Wu, R.-Y., Hall, I.H., and Huang, H.-C. (1979) J. Org. Chem. 44, 2180. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

188

Opender Koul

BENZOYLOXY TETRA-ACETOXY-4HYDROXY-DIHYDRO-β-AGAROFURAN

C30H38O12 (590.62)

M.p. : 75–76° [α]25 D : –21.7° (CHCl3)

AcO

CH2OAc OBz OAc

O HO

OAc

(1)

(1) SOURCE: Maytenus canariensis (Loes) Kunk et Sund. (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy

Remarks

Feeding deterrence = Threshold level

Treatment to larvae. (1)

(1) Gonzalez, A.G., Jimenez, I.A., Ravelo, A.G., Sazatornil, J.G., and Bazzocchi, I.L. (1993) Tetrahedron, 49, 697.

© 2005 by CRC Press LLC

Insect Antifeedants

BENZOYLOXY TRIACETOXY-1,4DIHYDROXY DIHYDRO-β-AGAROFURAN

189

C28H36O11 (548.59)

Oil [α]25 D : +25° (CHCl3)

HO

CH2OAc OBz OAc

O HO

OAc

(1)

(1) SOURCE: Maytenus canariensis (Loes) Kunk. & Sund., peralillo (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy

Remarks

Feeding deterrence = Threshold level

Treatment to larvae. (1)

(1) Gonzalez, A.G., Jimenez, I.A., Ravelo, A.G., Sazatornil, J.G., and Bazzocchi, I.L. (1993) Tetrahedron, 49, 697.

© 2005 by CRC Press LLC

190

Opender Koul

BENZOYLOXY TRIACETOXY-4,8DIHYDROXY DIHYDRO-β-AGAROFURAN

C28H36O11 (548.59)

Oil [α]25 D : –23.3° (CHCl3)

AcO

CH2OAc OBz OH

O HO

OAc

(1)

(1) SOURCE: Maytenus canariensis (Loes) Kunk. & Sund., peralillo (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy

Remarks

Feeding deterrence = Threshold level

Treatment to larvae. (1)

(1) Gonzalez, A.G., Jimenez, I.A., Ravelo, A.G., Sazatornil, J.G., and Bazzocchi, I.L. (1993) Tetrahedron, 49, 697.

© 2005 by CRC Press LLC

Insect Antifeedants

BENZYL ALCOHOL

191

C7H8O (108.13)

M.p. : –15.19° B.p. : 204.7°/760 mm

CH2OH

n20 D

: 1.045

d15 15

: 1.05

(1)

(1) SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Synthetic diet feeding

Conc. / Dose 0.08%

Efficacy

Remarks

Feeding deterrence = 50%

Treatment to 50–75 aphids at random for 24 h. Concentration = EC50 value. (2)

LD50 (rats): 3.1 g/kg (oral) (1) Vogel, A.I. (1959) Practical Organic Chemistry, Longmans, London, p. 711. (2) Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) J. Chem. Ecol., 7, 273. (3) Smyth, H.F. Jr., Carpenter, C.P., and Carol, S.W. (1951) Arch. Ind. Hyg. Occup. Med., 4, 119.

© 2005 by CRC Press LLC

(3)

192

Opender Koul

BERBERINE

C20H18O4N (336.37)

No data given

O O

N

+

CH 3O OCH3

(1, 2)

(2)

SOURCE: Coptis japonica Makino, evergreen rosette (Ranunculaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Hyphantria cunea (Drury) (Fall webworm)

Leaf disk assay

500 ppm

Feeding deterrence = 75.4%

1. Treatment to 4th instar larvae prestarved for 9 h. Treatment duration = 24 h. (2)

2. Agelastica coerulea Baly. (Leaf beetle)

Leaf disk assay

125 ppm

Feeding deterrence = 57.5%

250 ppm

91.1%

500 ppm

97.2%

2. Treatment to adults pre-starved for 9 h. Treatment duration = 24 h. (2) Compound tested as berberine chloride

LD50 (mice): 329 mg/kg (oral)

(3)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Park, I., Lee, H., Lee, S., Park, J., and Ahn, Y. (2000) J. Econ. Entomol., 93, 331. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold

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Insect Antifeedants

BERGAPTEN

193

C12H8O4 (216.19)

O

O

M.p. : 188–189°

O

OCH3

(1, 2)

(2)

SOURCE: Boeninghausenia albiflora (Hook.) Reichb. ex Meissn., flea plant (Rutaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk choice test

500 ppm

Feeding deterrence = 100% in 2 h

Treatment to 3rd instar larvae. The activity retarded after 6 h, thus compound was termed as relative antifeedant. (2)

2. Peridroma saucia (Hubner) (Variegated cutworm)

Leaf disk choice test

57.0 µg/cm2

Feeding deterrence = 5.5%

2. Treatment to 5th instar larvae for 5 h. (3)

LD50 (mice): 8100 mg/kg (oral)

(4)

(1) Thoms, H. and Baetcke, E. (1912) Chem. Ber., 45, 3705. (2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045. (3) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194. (4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand, Reinhold.

© 2005 by CRC Press LLC

194

Opender Koul

(+) BICUCULLINE

C20H17O6N (367.36)

M.p. : 215° [α]D : +130° (CHCl3)

O N

O H

H O

O O

O

(1)

(1) SOURCE: Dicentra cucullaria L., squirrel corn (Fumariaceae)

(1,2)

ACTIVITY PROFILE Test Insect Diabrotica virgifera virgifera LeConte (Western corn rootworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

4.71 µg/1.5 cm2 disk

Feeding deterrence = 50%

Treatment to adults of resistant insects.

2.47 µg/1.5 cm2 disk

Feeding deterrence = 50%

Treatment to adults of susceptible insects.

Remarks

Concentrations = EC50 values. (2)

(1) (1982) Dictionary of Organic Compounds, Vol. 1, Chapman & Hall, New York, p. 640. (2) Mullin, C.A., Mason, C.H., Chou, J. and Linderman, J.R. (1992) In C.A. Mullin and J.G. Scott (eds.), Molecular Mechanism of Insecticide Resistance: Diversity Among Insects, ACS Symp. Ser. 505, Washington, D.C., pp. 288–308.

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Insect Antifeedants

(–) BICUCULLINE

195

C20H17O6N (367.36)

M.p. : 193–195° [α]33 D : –128° (CHCl3)

O + N

O H

H

Cl

O O O

O

(1)

(1) SOURCE: Fumaria parviflora, F. vaillantii, fumitory, and Corydalis swertzovii (Fumariaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Diabrotica virgifera virgifera LeConte (Western corn rootworm)

Test Method Leaf disk choice test

Conc. / Dose 69.0 nmol/ 1.5 cm2 disk

Efficacy

Remarks

Feeding deterrence = 50% after 24 h.

Treatment to adults of cyclodieneresistant insects. (2)

Feeding deterrence = 40% after 48 h.

Data calculated from Reference 2. ( – assayed as MeCl)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Mullin, C.A., Mason, C.H., Chou, J., and Linderman, J.R. (1992) In C.A. Mullin and J.G. Scott (eds.) Molecular Mechanism of Insecticide Resistance: Diversity Among Insects, ACS Symp. Ser. 505, Washington, D.C., pp. 288–308.

© 2005 by CRC Press LLC

196

Opender Koul

BILOBALIDE

C15H18O8 (326.30)

M.p. : >300° [α]20 D : –66.6° (Acetone)

O

O

O

O OH

O OH

O H

(1)

(1, 2) SOURCE: Ginkgo biloba L., gingko tree (Ginkgoaceae)

(2)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Japanese cabbage butterfly)

Test Method Leaf disk no-choice test

Conc. / Dose 500 µg/disk

Efficacy Feeding deterrence = 90%

Remarks Treatment to 3rd instar larvae. (2)

(1) Nakanishi, K., Habaguchi, K., Nakadaira, Y., Woods, M.C., Maruyama, M., Major, R.T., Alauddin, M., Patel, A.R., Weinges, K., and Bahr, W. (1971) J. Am. Chem. Soc., 93, 3544. (2) Matsumoto, T. and Sei, T. (1987) Agric. Biol. Chem., 51, 249.

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Insect Antifeedants

BIOCHANIN

197

C22H22O10 (446.41)

M.p. : 220° [α]30 D : –35.3° (HCONMe2)

CH2OH

O O

O OH

HO

H

O

OCH3

OH

(1)

(1, 2) SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Costelytra zealandica (White) (Scarab beetle)

Synthetic diet feeding

2. Heteronychus arator (Fab.) (Black beetle)

Synthetic diet feeding

Test Insect

Efficacy

Remarks

200 µg/ml

Feeding deterrence = 23%

1. Treatment to 3rd instar larvae after 24-h starvation. (2)

200 µg/ml

Feeding deterrence = 51%

2. Treatment to 3rd instar larvae after 24-h starvation. (2) Data calculated from Reference 2.

(1) Wong, E., Mortimer, P.I., and Geissman, T.A. (1965) Phytochemistry, 4, 89. (2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

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198

Opender Koul

(6S)-2,10-BISABOLADIEN-1-ONE

C15H24O (220.18)

Oil [α]D : –34° (EtOH)

O H

(1)

(1) SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera littoralis (Boisd.) (Eygyptian cotton leaf worm)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

1. Treatment to 6th instar larvae.

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Choice feeding assay

66.5 nmol/cm2

Feeding deterrence = 50.0%

2. Treatment to adults.

3. Myzus persicae (Sulzer) (Green peach aphid)

Choice feeding assay

92.2 nmol/cm2

Feeding deterrence = 50.0%

3. Treatment to apterous adult aphids.

4. Rhopalosiphum padi (L.) (Cereal aphid)

Choice feeding assay

110.0 nmol/cm2

Feeding deterrence = 50.0%

4. Treatment to apterous adult aphids.

5. Sitobion avenae (Fab.) (Grass aphid)

Choice feeding assay

84.4 nmol/cm2

Feeding deterrence = 50.0%

5. Treatment to apterous adult aphids.

6. Diuraphis noxia (Mordvilko) (Wheat aphid)

Choice feeding assay

14.9 nmol/cm2

Feeding deterrence = 50.0%

6. Treatment to apterous adult aphids. Concentrations = EC50 values

Test Insect

Efficacy

Remarks

(1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.

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Insect Antifeedants

BISABOLANGELONE

199

C15H20O3 (248.32)

M.p. : 148–149° [α]D20 : +198° (EtOH)

O OH

H

O H

(1, 2)

(1)

SOURCE: Angelica silvestris L., angelica (Apiaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 139

1. Treatment to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 195 = 200

2. Treatment to

(2)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 200

4. Peridroma saucia (Hubner) (Variegated cutworm)

Leaf disk choice test

14.25 µg/cm2

Feeding inhibition = 55.0% Feeding inhibition = 78.8%

28.5 µg/cm2

5. Pieris brassicae (L.) (Large white butterfly

(1) (2) (3) (4)

Leaf disk dual choice test

5.0 µg/cm2

Feeding inhibition = 100.0%

Novotny, L., Samek, Z., and Sorm, F. (1966) Tetrahedron Lett., 7, 3541. Nawrot, J., Harmatha, J., and Novotny, L. (1984) Biochem. Syst. Ecol., 12, 99. Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194. Benz, C., Abivardi, C., and Muckensturm, B. (1989) Entomol. Exp. Appl., 53, 257.

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Adults. Larvae. (2) 3. Treatment to larvae. (2) Data based on a 0 to 200 greater deterrence scale 4. Treatment to 5th instar larvae for 5 h. (3)

Treatment to 3rd instar larvae for 24 h. (4)

200

Opender Koul

N, 3-BIS (4-CHLOROPHENYL)-4,5DIHYDRO-1H-PYRAZOLE-1 CARBOXAMIDE

N

C16H11ON3Cl2 (332.17)

NCONH

Only spectral data given

Cl

Cl

(1, 2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Ceramica picta (Harris) (Zebra caterpillar)

Test Method Leaf dip test

Conc. / Dose

Efficacy

Remarks

500 ppm

Feeding deterrence = 91.8% (small) 91.2% (medium) 85.4% (large)

1. Treatment at random to small-, medium-, and largesized larvae. (2)

250 ppm

Feeding deterrence = 78.9% (small) 74.5% (medium) 48.7% (large)

125 ppm

Feeding deterrence = 14.8% (small) 25.2% (medium) 28.0% (large)

(1) Mulder, R., Wellinga, K., and van Daalen, J.J. (1975) Naturwissenschaften, 62, 531. (2) Tamaki, G. (1976) J. Econ. Entomol., 63, 644.

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Data calculated from Reference 2.

Insect Antifeedants

BORNEOL

201

C10H18O (154.25)

M.p. : 208–209° B.p. : 212° [α]D20 : –37.74° (EtOH)

HO

(2)

(1, 2) SOURCE: Commercial sample

(1)

ACTIVITY PROFILE Test Insect Hylobius pales (Herbst.) (Pales weevil)

Test Method Twig dip treatment choice assay

Conc. / Dose 10.0%

Efficacy

Remarks

Feeding inhibition = 68.0%

Treatment to 22–65 mg body weight weevils for 24 h. (1) Data calculated from Reference 1.

LD50 (rats): 5800 mg/kg (oral)

(3)

(1) Salom, S.M., Carlson, J.A., Aug, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

202

Opender Koul

BORNYL ACETATE

C12H20O2 (196.28)

M.p. : 27° B.p. : 103°/14 mm [α]D : –42.0°, –44.45°

AcO

(1, 2)

(1, 2)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

1. Pieris rapae crucivora Boisd. (Cabbage butterfly)

Leaf disk choice assay

2. Hylobius pales (Herbst.) (Pales weevil)

Twig dip treatment choice assay

Efficacy

Remarks

10−1 mol/l

Feeding inhibition = 100%

1. Treatment to 5th instar larvae for 2 h. (2)

10.0%

Feeding inhibition = 50%

2. Treatment to weevils of 22–65 mg body weight for 24 h. (3) Data calculated from Reference 3.

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 58. (2) Yano, K. (1987) J. Agric. Food Chem., 35, 889. (3) Salom, S.M., Carlson, J.A., Aug, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407.

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Insect Antifeedants

2-BROMODECANOIC ACID

203

C10H19O2Br (251.16)

M.p. : 40°

Br

COOH

(1, 2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk assay

0.05 mg/cm2

Efficacy

Remarks

Feeding inhibition = 52.7% after 6 days of treatment exposure.

Treatment to larvae of 10–13 mg body weight (2)

Data calculated from Reference 2.

(1) Bagard, A. (1907) Bull. Soc. Chim., 1, 310 and 348. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC

204

Opender Koul

22-α-BROMO-22,23-DIHYDRO-23α,β-ETHOXYAZADIRACHTIN

C37H47O17Br (843.63)

No data given

COOCH3

O O

O

OH

Br

OH

O OC2H5 O

O

OH

AcO H

H3COOC

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to starved 24- to 36-h-old final stadium larvae. Bioassay terminated after 1 h of feeding. (1)

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk choice assay

1.0 ppm

Feeding inhibition = 38.7%

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk choice assay

1.0 ppm

Feeding inhibition = 20.5%

Data calculated from Reference 1.

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149.

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Insect Antifeedants

22-α-BROMO-22,23-DIHYDRO-23α,β-ISOPROPOXYZADIRACHTIN

205

C38H49O17Br (857.66)

No data given

COOCH3

O O

O

OH

OH

Br

O OPr O OH

AcO H3COOC

O

H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to starved 24- to 36-h-old final stadium larvae. Bioassay terminated after 8–9 h of feeding. (1)

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk nochoice assay

1.0 ppm

Feeding inhibition = 64.7%

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk nochoice assay

1.0 ppm

Feeding inhibition = 69.0%

Data calculated from Reference 1. Approximate EC50 = 0.82 ppm

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149.

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206

Opender Koul

22-α-BROMO-22,23-DIHYDRO-23β-METHOXYZADIRACHTIN

C36H45O17Br (829.60)

No data given

COOCH3

O O

O

OH

OH

Br

O OCH3 O OH

AcO H3COOC

O

H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to starved 24- to 36-h-old final stadium larvae. Bioassay terminated after the larvae had eaten approximately 50% of one of the disks. (1)

Glass fiber disk choice assay

1.0 ppm

Feeding inhibition = 50.0%

Glass fiber disk nochoice assay

1.0 ppm

Feeding inhibition = 69.7%

Data calculated from Reference 1 for nochoice assay, which was run for 8 to 9 h.

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149.

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Insect Antifeedants

2-BROMOEICOSANOIC ACID

207

C20H39O2Br (391.44)

No physical data given

HOOC Br

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk assay

0.05 mg/cm2

Efficacy

Remarks

Feeding inhibition = 55.0% after 6 days of treatment exposure.

Treatment to larvae of 10–13 mg body weight. (1) Data calculated from Reference 1.

(1) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC

208

Opender Koul

α-BROMOERGOCRYPTINE

C32H40O5N5Br (654.60) OH O

[α]20 D : –195° (CH2Cl2)

N N O

M.p. : 215–218° (dec.)

N O

O

N

HN Br

(1)

(1, 2)

SOURCE: Commercial sample (2) It has been obtained from Lolium perenne L., rye grass (Graminaceae), infected with fungus Neotyphodium lolii. ACTIVITY PROFILE Test Insect Heteronychus arator (Fab.) (Black beetle)

LD50 (rats): 72 mg/kg (ivn.)

Test Method Artificial diet feeding. Choice test

Conc. / Dose

Efficacy

Remarks

5.0 µg/g

Feeding inhibition = 25.0%

Treatment to adults for 96 h. (2) Data calculated from Reference 2.

20.0 µg/g

Feeding inhibition = 70.4%

(3)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

2-BROMOOCTADECANOIC ACID

209

C18H35O2Br (363.38)

M.p. : 60°

COOH Br

(1, 2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk assay

Efficacy

Remarks

0.05 mg/cm2

Feeding inhibition = 53.5% after 6 days of treatment exposure.

Treatment to larvae of 10–13 mg body weight. (2)

0.25 mg/cm2

Feeding inhibition = 85.4% after 6 days of treatment exposure.

Data calculated from Reference 2.

(1) Radcliffe, L.G. and Gibson, W. (1923) J. Soc. Dyers Colourists, 39, 4. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

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210

Opender Koul

BRUCEANOL–A

C28H30O11 (542.54)

M.p. : 174–177° [α]D25 : +60° (EtOH)

OH COOCH3

HO HO

O OCO

O H O

O

(1)

(1, 2) SOURCE: Brucea antidysenterica Mill, brucea (Xanthoxylaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method Leaf disk assay

Conc. / Dose

Efficacy

6.0 µg/cm2

Feeding inhibition = 60–90% after 6 days of treatment.

3.0 µg/cm2

Feeding inhibition = 60–90% after 2 days of treatment, which declines to 30–60% after 6 days of treatment.

Remarks Treatment to 3rd instar larvae.

(2)

(1) Polonsky, J., Baskevitch Varon, Z., and Sevenet, T. (1975) Experientia, 31, 1113. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

Insect Antifeedants

BRUCEANOL–B

211

C27H36O11 (536.58)

Amorphous solid M.p. : 170–172°

OH

[α]25 D : +32° (MeOH) HO

COOCH3

HO O

O

OCO H O

O

(1)

(1, 2) SOURCE: Brucea antidysenterica Mill, brucea (Xanthoxylaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method Leaf disk assay

Conc. / Dose

Efficacy

12.0 µg/cm2

Feeding inhibition = 60–90% after 2 days of treatment and goes down to 30–60% after 6 days.

6.0 µg/cm2

Feeding inhibition = 60–90% after 2 days of treatment, which declines to 0–30% after 6 days of treatment.

Remarks Treatment to 3rd instar larvae.

(2)

(1) Okano, M., Fukamiya, N., Aratani, T., Juichi, M., and Lee, K.-H. (1985) J. Nat. Prod., 48, 972. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

212

Opender Koul

BRUCEANTIN

C28H36O11 (548.58) OH

M.p. : 225–226°

HO

[α]25 D : –27.7° (Pyridine)

COOCH3 O OCO

O H O

HO

O

H

(1)

(1, 2) SOURCE: Brucea antidysenterica Mill., brucea (Xanthoxylaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Heliothis virescens (Fab.) (Tobacco budworm)

2. Epilachna varivestis Muls. (Mexican bean beetle)

3. Spodoptera eridania (Cramer) (Southern armyworm)

LD50 (mice): 7 mg/kg (oral)

Test Method Leaf disk assay

Whole leaf application

Whole leaf application

Conc. / Dose

Efficacy

12.0 µg/cm2

Feeding inhibition = 90–100% after 2 days of treatment and goes down to 60–90% after 6 days.

3.0 µg/cm2

Feeding inhibition = 90–100% after 2 days of treatment, which declines to 30–60% after 6 days of treatment.

500 ppm

Feeding inhibition = 90%

250 ppm

Feeding inhibition = 72.2%

500 ppm

Feeding inhibition = 29.0%

Remarks 1. Treatment to 3rd instar larvae.

(2)

2. Treatment to 4th instar larvae starved for 2 h. Treatment duration = 24 h. Data calculated from Reference 3. (3) Treatment to freshly molted 5th instar larvae for 24 h. Data calculated from Reference 3. (3) (4)

(1) Kupchan, S.M., Britton, R.W., Lacadie, J.A., Ziegler, M.F., and Sigel, C.W. (1975) J. Org. Chem., 40, 648. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442. (3) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497. (4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

BRUCEINE–A

213

C26H34O11 (522.55)

M.p. : 267–270° [α]D25 : –86.3° (Pyridine)

OH HO

COOCH3 O OCO

O H O

HO

O

H

(1)

(1, 2) SOURCE: Brucea amarissima (Lour.) Merril., common brucea (Xanthoxylaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Heliothis virescens (Fab.) (Tobacco budworm)

Test Method Leaf disk assay

Conc. / Dose

Efficacy

12.0 µg/cm2

Feeding inhibition = 60–90% after 6 days of treatment.

6.0 µg/cm2

Feeding inhibition = 60–90% after 2 days of treatment, which declines to 30–60% after 6 days of treatment.

Remarks 1. Treatment to 3rd instar larvae.

(2)

2. Epilachna varivestis Muls. (Mexican bean beetle)

Whole leaf application

500 ppm

Feeding inhibition = 64.2%

2. Treatment to 4th instar larvae starved for 2 h. Treatment duration = 24 h. Data calculated from Reference 3. (3)

3. Spodoptera eridania (Cramer) (Southern armyworm)

Whole leaf application

500 ppm

Feeding inhibition = 55.8%

3. Treatment to freshly moulted 5th instar larvae for 24 h. Data calculated from Reference 3. (3)

(1) Polonsky, J., Baskevitch, Z., Gaudemer, A., and Das, B.C. (1967) Experientia, 23, 424. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442. (3) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC

214

Opender Koul

BRUCEINE–B

C23H28O11 (480.47)

M.p. : 264–268° [α]D : –76° (Pyridine)

OH COOCH3

HO O

OCOCH3

O H O

HO

O

H

(1)

(1, 2) SOURCE: Brucea amarissima (Lour.) Merril., common brucea (Xanthoxylaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Heliothis virescens (Fab.) (Tobacco budworm)

2. Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf disk assay

Whole leaf application

Conc. / Dose

Efficacy

Remarks

19.8 µg/cm2

Feeding inhibition = 60–90% after 6 days of treatment.

1. Treatment to 3rd instar larvae. (2)

12.0 µg/cm2

Feeding inhibition = 60–90% after 2 days of treatment, which declines to 30–60% after 6 days of treatment.

500 ppm

Feeding inhibition = 75.0%

2. Treatment to 4th instar larvae starved for 2 h. Treatment duration = 24 h. Data calculated from Reference 3. (3)

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 131. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442. (3) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC

Insect Antifeedants

BRUCEINE–C

215

C28H36O12 (564.58) OH

M.p. : 175–180° [α]D : –34.2° (Pyridine)

COOCH3

HO

OH

O OCO

O H O

HO

O

H

(1)

(1, 2) SOURCE: Brucea amarissima (Lour.) Merril., common brucea (Xanthoxylaceae)(1)

ACTIVITY PROFILE Test Insect 1. Heliothis virescens (Fab.) (Tobacco budworm)

2. Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf disk assay

Whole leaf application

Conc. / Dose

Efficacy

Remarks

19.8 µg/cm2

Feeding inhibition = 90–100% after 2 days and 60–90% after 6 days of treatment.

1. Treatment to 3rd instar larvae. (2)

12.0 µg/cm2

Feeding inhibition = 60–90% after 2 days of treatment, which declines to 30–60% after 6 days of treatment.

6.0 µg/cm2

Feeding inhibition = 60–90% after 2 days of treatment, which declines to 0–30% after 6 days of treatment.

500 ppm

Feeding inhibition = 66.3%

2. Treatment to 4th instar larvae starved for 2 h. Treatment duration = 24 h. Data calculated from Reference 3. (3)

(1) Polonsky, J., Baskevitch, Z., Gaudemer, A., and Das, B.C. (1967) Experientia, 23, 424. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442. (3) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC

216

Opender Koul

BRUCEINE–D

C20H26O9 (410.42)

M.p. : 285–290° [α]D : –21° (Pyridine)

OH HO HO

O OH

O OH

H

O

O

H

(1)

(1, 2) SOURCE: Brucea amarissima (Lour.) Merril., common brucea (Xanthoxylaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method Leaf disk assay

Conc. / Dose

Efficacy

6.0 µg/cm2

Feeding inhibition = 90–100% after 2 days and 60–90% after 6 days of treatment.

3.0 µg/cm2

Feeding inhibition = 60–90% after 2 days of treatment which declines to 30–60% after 6 days of treatment.

Remarks Treatment to 3rd instar larvae.

(2)

(1) Polonsky, J., Baskevitch, Z., Das, B.C., and Muller, J. (1968) Compt. Rend., 267, 1346. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

Insect Antifeedants

BUCHANINOSIDE

217

C32H42O11 (602.68) O

M.p. : 259° [α]D : –44.6° (CHCl3)

O

H3CO OH

OAc O O

O

OH

O

(1)

(1) SOURCE: Elaeodendron buchananii, African tropical tree (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera exempta (Walker) (Nutgrass armyworm)

Test Method Leaf disk choice assay

Conc. / Dose 100.0 µg/µl

Efficacy

Remarks

Feeding inhibition = 70.0%

Treatment to 6th instar larvae prestarved for 2 h. Treatment duration = 2 h. (1)

(1) Tsujino, Y., Ogoche, J.I.J., Tazaki, H., Fujimori, T., and Mori, K. (1995) Phytochemistry, 40, 753.

© 2005 by CRC Press LLC

218

Opender Koul

BUDDLEIN–A

C20H22O7 (374.39)

M.p. : 106–108° [α]D25 : –82.3° (CH3OH)

O O O O O

CH2

HO O

(1)

(1, 2) SOURCE: Viguiera buddleiaeformis, viguiera (Asteraceae)

(1,2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk no-choice assay

Conc. / Dose 70.0 µg/ 1.5 cm2

Efficacy

Remarks

Feeding inhibition = 60.2%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 30 min. (1)

(1) Passreiter, C.M. and Isman, M.B. (1997) Biochem Syst. Ecol., 25, 371. (2) De Vivar, A.R., Guerrero, C., Diaz, E., Bratoeff, E.A., and Jimenez, L. (1976) Phytochemistry, 15, 525.

© 2005 by CRC Press LLC

Insect Antifeedants

BUSSEIN

219

C43H54O18 (858.92)

O

M.p. : 300–304° (dec.) [α]20 D : –57° (CHCl3)

OAc AcO O O O H3COOC

O

O OH OAc OH OCO

(1)

(1) SOURCE: Entandrophragma bussei Sprague, mahogany (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Peridroma saucia (Hubner) (Variegated cutworm)

Artificial diet feeding

0.5 µM/g

Feeding inhibition = Weak

Treatment to neonate larvae for 24 h. 34% of the larvae were seen on treated diets against 100% of controls in a choice situation. (2)

2. Ostrinia nubilalis (Hubner) (European corn borer)

Leaf disk nochoice assay

50 µg/g

Feeding inhibition = 45.0% Feeding inhibition = 74.0%

2. Treatment to neonate larvae for 48 h.

500 µg/g

(3) Data calculated from Reference 3.

(1) (1982) Dictionary of Organic Compounds, Vol. 1, Chapman & Hall, New York, p. 900. (2) Champagne, D.E., Isman, M.B., and Towers, G.H.N. (1989) In J.T. Arnason, B.J.R. Philogene, and P. Morand (eds.), Insecticides of Plant Origin, ACS Symp. Ser. 387, Am. Chem. Soc., Washington, D.C., pp. 95–109. (3) Arnason, J.T., Philogene, B.J.R., Donskov., N., and Kubo, I. (1987) Entomol. Exp. Appl., 43, 221.

© 2005 by CRC Press LLC

220

Opender Koul

3β-n BUTYRYLOXY-1-OXOMELIAC8 (14)-ENATE

C31H40O8 (540.65) O

M.p. : 65–68° [α]20 D : –135° (CHCl3)

O

H3COOC

O

O

OCO

(1)

(1) SOURCE: Khaya ivorensis Chev., African mahogany (Meliaceae)

(1,2)

ACTIVITY PROFILE Test Insect Agrotis segetum (L.) (Turnip cutworm)

Test Method Artificial diet feeding

Conc. / Dose 100 ppm

Efficacy

Remarks

Feeding inhibition = 36.0%

Treatment to larvae for 5 days. (1)

(1) Vanucci, C., Lange, C., Lhommet, G., Dupont, B., Davoust, D., Vauchot, B., Clement, J.L., and Brunck, F. (1992) Phytochemistry, 31, 3003.

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Insect Antifeedants

CAFFEIC ACID

221

C9H8O4 (180.16)

M.p. : 200°

COOH

CH

CH

OH OH

(1, 2)

(1)

SOURCE: Pteridium aquilinum (L.) Kuhn, bracken fern (Pteridophyte)

(2, 3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Pieris brassicae (L.) (Large white butterfly)

Leaf disk no-choice test

5.6 × 10–2 M

Feeding ratio = 2.87

1. Treatment to 2nd day 5th instar unstarved larvae. Ratio <20 considered as effective deterrence (2)

2. Locusta migratoria (L.) (Migratory locust)

Glass fiber disk choice test

0.5% dry weight

Significant deterrent effect

2. Treatment to 3-day-old 5th instar nymphs for 3 to 4 h. (4)

(1) (2) (3) (4)

Pacsu, E. and Stieber, C. (1929) Ber., 62, 2974. Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187. Bohm, B.A. and Tryon, R.M. (1967) Can. J. Bot., 45, 585. Bernays, E.A. (1990) Entomol. Exp. Appl., 54, 53.

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222

Opender Koul

CAFFEINE

C8H10O2N4 (194.19)

O

M.p. : 235° (anhyd.) 178° (subl.) [α]15 D : +2°

N N N O

N

(1)

(1, 2) SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Phormia regina (Meigen) (Blow fly)

LD50 (rats): 127 mg/kg (oral)

Test Method Sucrose solution feeding

Conc. / Dose 10.0 mM

Efficacy

Remarks

Feeding inhibition = 40.0% after 6 h 46.0% after 24 h

Treatment to 2-, 4-, and 6-day-old adults, pre-starved for 24 h. (2)

(3)

(1) Biltz, H. and Beck, A. (1928) J. Prakt. Chem., 118, 198. (2) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299. (3) Palm, P.E., Arnold, E.P., Rachwell, P.C., Leyczek, J.C., Teague, K.W., and Kensler, C.J. (1978) Toxicol. Appl. Pharmacol., 44, 1.

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Insect Antifeedants

223

CAMELLIDIN–II

C53H84O24 (1105.23) M.p. : 211–212° [α]D25 : –6° (MeOH) HO

OH

O OH

O

O

O

O

O HO

HO HO

O

O

O HO

H

HO COOH

OH

HO

HO

HO

OH

(1)

(1, 2) SOURCE: Camellia japonica L., common camellia (Theaceae)

(2)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina Del’Orza (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose 0.25%

Efficacy Feeding ratio = 46.8%

Remarks Treatment to 5th instar larvae. Deterrence observed to be of mild nature only. (1)

(1) Itokawa, H., Nakajima, H., Ikuta, A., and Iitaka, Y. (1981) Phytochemistry, 20, 2539. (2) Numata, A., Kitajima, A., Katsuno, T., Yamamoto, K., Nagahama, N., Takahashi, C., Fujiki, R., and Nabae, M. (1987) Chem. Pharm. Bull., 35, 3948.

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224

Opender Koul

CANIN

C15H18O5 (278.30) OH

M.p. : 245–246° (M.p. : 250° for Crystals from Me2CO)

O

[α]23 D : –30.5° (EtOH) O H

CH2

O

O

(1, 2)

(1,2)

SOURCE: Chrysanthemum macrophyllum W&K, chrysanthemum (Asteraceae)

(3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 51–100

1. Treatment given to adults.

2. Tribolium confusum Jacq. Duv. (Confused flour beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Lee, K.H., Simpson, R.F., and Geissman, T.A. (1969) Phytochemistry, 8, 1515. (2) Bhadane, N.R., and Shafizadeh, F. (1975) Phytochemistry, 14, 2651. (3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Dorzdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin., 24, 27.

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Insect Antifeedants

(−) – CANNABISIN–B

225

C34H32O8N2 (596.64) O

HO

Amorphous powder

OH

[α]D : –38° (MeOH) H N N H

HO O

OH

OH OH

(1)

(1) SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae)

(1)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe. (Subterranean termite)

Test Method Paper disk choice test

Conc. / Dose 5000 ppm

Efficacy Antifeedant index value = 7.10

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index value below 20.0 for a compound considered as highly deterrent (1)

226

Opender Koul

(–) – CANNABISIN–D

C36H36O8N2 (624.69) OH

O CH3O

M.p. : 164–166° (165–168°)

H N N H

HO O

OH

OCH3 OH

(1, 2)

(1, 2)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae)

(1)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method Paper disk choice test

Conc. / Dose 5000 ppm

Efficacy Antifeedant index value = 12.93

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index value below 20.0 for a compound considered as highly deterrent (1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105. (2) Sakakibara, I., Ikeya, Y., Hayashi, K., and Mitsuhashi, H. (1992) Phytochemistry, 31, 3219.

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Insect Antifeedants

CAPILLARIN

227

C13H10O2 (198.22)

M.p. : 124°

O

O

(1, 2, 3)

(1, 2)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae)

(3)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method

Conc. / Dose

Leaf disk test

10–1 mol/l

Efficacy

Remarks

Feeding inhibition = 97.0%

Treatment to 5th instar larvae for 2 h. (3)

(1) Harada, R., Noguchi, S., and Sugiyama, N. (1960) Nippon Kagaku Zasshi, 81, 654. (2) Bohlmann, F. and Kleine, K.–M. (1962) Chem. Ber., 95, 39. (3) Yano, K. (1987) J. Agric. Food Chem., 35, 889.

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228

Opender Koul

CAPILLENE

C12H10 (154.21)

Oil d20 0

: 0.977

(1)

(1, 2) SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method Leaf disk test

Conc. / Dose 0.3 mg/2 cm diameter disk.

(1) Harada, R. (1957) J. Chem. Soc. Jap., 78, 415. (2) Yano, K. (1983) J. Agric. Food Chem., 31, 667.

© 2005 by CRC Press LLC

Efficacy

Remarks

Feeding inhibition = 100.0%

Treatment to 5th instar larvae for 2 h. However, consumption in controls was also 50% of the amount provided (2)

Insect Antifeedants

CAPILLIN

229

C12H8O (168.19)

M.p. : 79.5–80.5°

O

(1)

(1)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method

Conc. / Dose

Leaf disk test

10–1 mol/l

(1) Yano, K. (1987) J. Agric. Food Chem., 35, 889.

© 2005 by CRC Press LLC

Efficacy

Remarks

Feeding inhibition = 100.0%

Treatment to 5th instar larvae for 2 h. (1)

230

Opender Koul

(+) CARVONE

C10H14O (150.21)

B.p. : 230° [α]20 D : +62.3° (H2O)

O

n20 D

: 1.4995

d20 4

: 0.9608

CH2

(2)

(1, 2) SOURCE: Commercial sample

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Hylobius pales (Herbst.) (Pales weevil)

Twig dip treatment choice assay

10.0%

Feeding inhibition = 69.0%

1. Treatment to 22–65 mg weevil body weight for 24 h. Data calculated from Reference 1. (1)

2. Locusta migratoria (L.) (Migratory locust)

Wafer disk test

0.1% dry weight basis

Feeding inhibition = 50.0%

2. Treatment to 5th instar 3- to 6-day-old nymphs (3)

LD50 (rats): 1640 mg/kg (oral)

(4)

(1) Salom, S.M., Carlson, J.A., Ang, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407. (2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 55. (3) Bernays, E.A. and Chapman, R.F. (1977) Ecol. Entomol., 2, 1. (4) Jenner, P.M., Hagan, E.C., Taylor, J.M., Cook, E.L., and Fetzhugh, O.G. (1964) Food Cosmetics Toxicol., 2, 327.

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Insect Antifeedants

(–) CARVONE

231

C10H14O (150.21)

B.p. : 230° [α]20 D : +69.1° (H2O) n18 D

O

: 1.4999

CH2

(1, 2)

(1, 2) SOURCE: Commercial sample

(3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Hylobius pales (Herbst.) (Pales weevil)

Twig dip treatment choice assay

10.0%

Feeding inhibition = 65.5%

1. Treatment to 22–65 mg weevil body weight for 24 h. Data calculated from Reference 4. (4)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Artificial diet feeding

1.0%

Only 26.4% of normal pupae developed against 74.4 in controls due to phagodeterrence

2. Treatment to 10–20 mg body weight larvae.

0.5%

(1) (2) (3) (4)

Only 33.7% of normal pupae developed against 74.4 in controls due to phagodeterrence

Doeuvre, J. (1934) Bull. Soc. Chim., 1, 198. Naves, Y.R. and Bachmann, P. (1946) Helv. Chim. Acta, 29, 61. Meisner, J., Fleischer, A., and Eizick, C. (1982) J. Econ. Entomol., 75, 462. Salom, S.M., Carlson, J.A., Ang, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407.

© 2005 by CRC Press LLC

(3)

232

Opender Koul

β-CARYOPHYLLENE

C15H24 (204.36)

B.p. : 129–130°/14 mm [α]15 D : –5.2° (benzene)

H2C

(1)

(1, 2) SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Pieris rapae crucivora Boisd. (Cabbage butterfly)

Leaf disk test

2. Locusta migratoria (L.) (Migratory locust)

Wafer disk test

Test Insect

Efficacy

Remarks

10–1 mol/l

Feeding inhibition = 73.0%

1. Treatment to 5th instar larvae for 2 h. (2)

0.01% dry weight basis

Feeding inhibition = 50.0%

2. Treatment to 5th instar 3- to 6-day-old nymphs. (3)

(1) Aebi, A., Barton, D.H.R., and Lindsay, A.S. (1953) J. Chem. Soc., 3124. (2) Yano, K. (1987) J. Agric. Food Chem., 35, 889. (3) Bernays, E.A. and Chapman, R.F. (1977) Ecol. Entomol., 2, 1.

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Insect Antifeedants

6,7-EPOXY-3(15)-CARYOPHYLLENE

233

C15H24O (220.34)

Oil [α]D : –40° (CHCl3)

H H O

H CH2

(1)

(1) SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera littoralis (Boisd.) (Eygyptian cotton leaf worm)

Choice feeding assay

159.1 nmol/cm2

Feeding deterrence = 50.0%

1. Treatment to 6th instar larvae.

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

2. Treatment to adults.

3. Myzus persicae (Sulzer) (Green peach aphid)

Choice feeding assay

>500 nmol/cm2

Feeding deterrence = 50.0%

3. Treatment to apterous adult aphids.

4. Rhopalosiphum padi (L.) (Cereal aphid)

Choice feeding assay

43.3 nmol/cm2

Feeding deterrence = 50.0%

4. Treatment to apterous adult aphids.

5. Sitobion avenae (Fab.) (Grass aphid)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

5. Treatment to apterous adult aphids.

6. Diuraphis noxia (Mordvilko) (Wheat aphid)

Choice feeding assay

38.4 nmol/cm2

Feeding deterrence = 50.0%

6. Treatment to apterous adult aphids. Concentrations = EC50 values

Test Insect

Efficacy

Remarks

(1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.

© 2005 by CRC Press LLC

234

Opender Koul

CARYOPTIN

C26H36O9 (492.56)

M.p. : 176–177°

O

[α]D : –91° (CHCl3)

H

H O H

AcO

H

O

CH2 OAc OAc

(1, 2)

(1, 2) SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk test

Conc. / Dose 200 ppm

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to 3rd instar larvae. Feeding duration = 2 h. Larvae eventually starved to death. Thus compound termed as absolute antifeedant. (2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1973) Phytochemistry, 12, 1833. (2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC

Insect Antifeedants

CARYOPTIN HEMIACETAL

235

C26H38O10 (510.58)

OH

M.p. : 188–189°

O H

H O H

AcO

H

O

CH2 OAc OAc

(1, 2)

(1, 2)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk test

Conc. / Dose 200 ppm

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to 3rd instar larvae. Feeding duration = 2 h. Larvae eventually starved to death. Thus compound termed as absolute antifeedant. (2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1973) Phytochemistry, 12, 1833. (2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC

236

Opender Koul

CARYOPTINOL

C24H34O8 (450.53)

M.p. : 219–220° [α]D : –83° (CHCl3)

O H

H O H

HO O

CH2 OAc OAc

(1)

(1)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae)

(1,2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk test

Conc. / Dose 200 ppm

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to 3rd instar larvae. Feeding duration = 2 h. Larvae eventually starved to death. Thus compound termed as absolute antifeedant. (2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1973) Phytochemistry, 12, 1833. (2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

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Insect Antifeedants

CASTANOSPERMINE

237

C8H15O4N (189.21)

M.p. : 212–215° (dec.) [α]25 D : +79.7° (H2O)

OH OH

H HO

N HO

(1)

(1, 2) SOURCE: Castanospermum australe A. Cunn. and Fraser, black bean (Fabaceae)

(2)

ACTIVITY PROFILE Test Insect Acyrthosiphon pisum (Harris) (Pea aphid)

Test Method

Conc. / Dose

Efficacy

Remarks

Artificial diet feeding

0.00002 ± 0.00001%

Feeding inhibition = 50.0%

Treatment to aphids at random. Concentration = EC50 value (2)

(1) Hohenschutz, L.D., Bell, E.A., Jewess, P.J., Leworthy, D.P., Pryce, R.J., Arnold, E., and Clardy, J. (1981) Phytochemistry, 20, 811. (2) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045.

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238

Opender Koul

CATALPOSIDE OCO

C22H26O12 (482.44)

OH

H

M.p. : 215–216° [α]29 D : –167° (MeOH)

O O HOH2C

H O

CH2OH O OH

HO

H OH

(2)

(1)

SOURCE: Catalpa speciosa (Warder) Barney, catalpa (Bignoniaceae)

(2)

ACTIVITY PROFILE Test Insect Lymantria dispar (L.) (Gypsy moth)

Test Method

Conc. / Dose

Artificial diet feeding

1.7 mg/ml

Efficacy

Remarks

Feeding inhibition = 19.0%

Treatment to larvae. (2)

(1) Bobbit, J.M., Schmid, H., and Africa, T.B. (1961) J. Org. Chem., 26, 3090. (2) El-Naggar, S.F. and Doskotch, R.W. (1980) J. Nat. Prod., 43, 524.

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Insect Antifeedants

CEDRELONE

239

C26H30O5 (422.52)

O

M.p. : 209–214° [α]30 D : –65° (CHCl3)

O O

O OH

(1, 2)

(1, 2)

SOURCE: Cedrela toona Roxb., cedro toona (Meliaceae) Cedrela odorata L., Spanish cedar (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding inhibition = 100.0%

0.05%

Feeding inhibition = 50.0%

5.0 µg/cm2

Feeding inhibition = 50.5%

1. Treatment to larvae in the weight range of 100–130 mg for 24 h. Data calculated from Reference 3. (3) Treatment to 3rd instar larvae for 24 h. (4)

50.0 µg/cm2

Feeding inhibition = 75.8%

2. Peridroma saucia (Hubner) (Variegated cutworm)

Leaf disk choice test

28.6 µg/cm2

Feeding inhibition = 51.7%

3. Mamestra configurata Walker (Bertha armyworm)

Leaf disk choice test

28.6 µg/cm2

Feeding inhibition = 75.9%

4. Ostrinia nubilalis (Hubner) (European corn borer)

Leaf disk no-choice assay

50 µg/g

Feeding inhibition = 55.0%

2. Treatment to 5th instar larvae for 6 h. (5) 3. Treatment to 5th instar larvae for 6 h. (5) 4. Treatment to neonate larvae for 48 h. (6) Data calculated from Reference 6.

(1) Gopinath, K.W., Govindachari, T.R., Parthasarthy, P.C., Viswanathan, N., Arigoni, D., and Wildmann, W.C. (1961) Proc. Chem. Soc. (London), 446. (2) Chaterjee, A., Cjhakraborthy, T., and Chandrasekharan, S. (1971) Phytochemistry, 10, 2533. (3) Koul, O. (1983) J. Appl. Entomol., 95, 166. (4) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishnakumari, G.N. (1995) J. Chem Ecol., 21, 1586. (5) Koul, O. and Isman, M.B. (1992) Entomol. Exp. Appl., 64, 281. (6) Arnason, J.T., Philogene, B.J.R., Donskov, N., and Kubo, I. (1987) Entomol. Exp. Appl., 43, 221.

© 2005 by CRC Press LLC

240

Opender Koul

CEDRELONE ACETATE

C28H32O6 (464.56)

M.p. : 156–159° [α]D : –56° (CHCl3)

O

O O

O OAc

(1, 2)

(1)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding inhibition = 45.0%

5 µg/cm2

Treatment to 3rd instar larvae for 24 h. FI50 = 8.2 µg/cm2

Feeding inhibition = 45.2%

10 µg/cm2

Feeding inhibition = 57.0%

50 µg/cm2

Feeding inhibition = 61.5%

Data calculated from Reference 2. (2)

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishnakumari, G.N. (1995) J. Chem Ecol., 21, 1586.

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Insect Antifeedants

CEDRELONE EPOXIDE

241

C26H30O6 (438.52)

M.p. : 222–228° [α]D : –10.6° (CHCl3)

O

O

O O

O OH

(1, 2)

(1)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding inhibition = 56.5%

5 µg/cm2

Treatment to 3rd instar larvae for 24 h. FI50 = 0.85 µg/cm2

Feeding inhibition = 59.2%

10 µg/cm2

Feeding inhibition = 58.5%

50 µg/cm2

Feeding inhibition = 64.5%

Data calculated from Reference 2. (2)

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishnakumari, G.N. (1995) J. Chem Ecol., 21, 1586.

© 2005 by CRC Press LLC

242

Opender Koul

CEDRELONE EPOXIDE ACETATE

C28H32O7 (480.56)

M.p. : 214–217° [α]D : –26° (CHCl3)

O

O

O O

O OAc

(1, 2)

(1)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding inhibition = 46.8%

5 µg/cm2

Treatment to 3rd instar larvae for 24 h. FI50 = 4.5 µg/cm2

Feeding inhibition = 52.4%

10 µg/cm2

Feeding inhibition = 59.2%

50 µg/cm2

Feeding inhibition = 59.1%

Data calculated from Reference 2. (2)

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishnakumari, G.N. (1995) J. Chem Ecol., 21, 1586.

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Insect Antifeedants

CEDRELONE EPOXIDE-METHYLETHER

243

C27H32O6 (452.55)

Only spectral data given

O

O

O O

O OCH3

(1, 2)

(2)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding inhibition = 46.0%

5 µg/cm2

Treatment to 3rd instar larvae for 24 h. FI50 = 4.8 µg/cm2

Feeding inhibition = 51.6%

10 µg/cm2

Feeding inhibition = 52.4%

50 µg/cm2

Feeding inhibition = 63.0%

Data calculated from Reference 2. (2)

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishnakumari, G.N. (1995) J. Chem Ecol., 21, 1586.

© 2005 by CRC Press LLC

244

Opender Koul

CEDRELONE METHYLETHER

C27H32O5 (436.55)

M.p. : 207–210° [α]D : –13.4° (CHCl3)

O

O O

O OCH3

(1, 2)

(1)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding inhibition = 44.0%

5 µg/cm2

Treatment to 3rd instar larvae for 24 h. FI50 = 9.5 µg/cm2

Feeding inhibition = 50.5%

10 µg/cm2

Feeding inhibition = 48.5%

50 µg/cm2

Feeding inhibition = 57.2%

Data calculated from Reference 2. (2)

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishnakumari, G.N. (1995) J. Chem Ecol., 21, 1586.

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Insect Antifeedants

CELANGULIN

245

C32H40O14 (648.66)

Amorphous powder

OAc OAc

O

O

CH2 OAc

AcO

HO

O OAc

(1)

(1)

SOURCE: Celastrus angulatus Maxim., bittersweet tree (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method Artificial diet test

Conc. / Dose

Efficacy

Remarks

5 ppm

Feeding inhibition = 39.0%

10 ppm

Feeding inhibition = 63.0%

Treatment to 1st instar larvae. Calculations made on the basis of reduction in weight due to starvation. (1)

(1) Wakabayashi, N., Wu, W.J., Waters, R.M., Redfern, R.E., Mills, G.D. Jr., DeMilo, A.B., Lusby, W.R., and Andrzejewski, D. (1988) J. Nat. Prod., 51, 537–542.

© 2005 by CRC Press LLC

246

Opender Koul

α-CHACONINE (solanidine)

C45H73O14N (852.07)

M.p. : 243° [α]D : –85° (Pyridine)

N

2.Rham - glu - O

(1)

(1, 2) SOURCE: Solanum sp. (Solanaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Choristoneura fumiferana (Clemens) (Spruce budworm)

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Paper penicillin disk assay

Sensillum response recording

Conc. / Dose

Efficacy

Remarks

10–3 M

Feeding inhibition = 77.0%

1. Treatment to 6th instar larvae. (2)

10–4 M

Feeding inhibition = 41.0%

0.6% wet weight

Feeding inhibition = 50.0%

2. Treatment to adult beetles. Concentration = FI50 value. (3)

LD50 (rats): 84 mg/kg (ipr.) (1) (2) (3) (4)

(4)

(1994) Dictionary of Natural Products, Chapman & Hall, London. Bentley, M.D., Leonard, D.E., and Bushway, R.J. (1984) Ann. Entomol. Soc. Am., 77, 401. Mitchell, B.K. and Harrison, G.D. (1985) J. Chem. Ecol., 11, 73. Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

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Insect Antifeedants

CHALCONE 2′,4′-DIHYDROXY-4,6′-DIMETHOXY

247

C17H16O5 (300.29)

M.p. : 194–195°

OH

OCH3

H3CO

OH

O

(1)

(1)

SOURCE: Gnaphalium affine D. Don, cudweed (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

2.1 × 10–5 mol/cm2

Feeding inhibition = 50%

1. Treatment to 3rd instar larvae in the dark for 2 to 5 h. Concentration = FI50 value (1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC

248

Opender Koul

CHALCONE 2′-HYDROXY-4,4′,6′-TRIMETHOXY

C18H18O5 (314.32)

M.p. : 113°

OCH3

OCH3

H3CO

OH

O

(1)

(1)

SOURCE: Gnaphalium affine D. Don, cudweed (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

9.0 × 10–6 mol/cm2

Feeding inhibition = 50%

1. Treatment to 3rd instar larvae in the dark for 2 to 5 h. Concentration = FI50 value (1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC

Insect Antifeedants

CHALCONE 4,2′,4′,6′-TETRAMETHOXY

249

C19H20O5 (328.35)

M.p. : 119–121°

OCH3

OCH3

H3CO

OCH3

O

(1)

(1)

SOURCE: Gnaphalium affine D. Don, cudweed (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

5.2 × 10–7 mol/cm2

Feeding inhibition = 50%

1. Treatment to 3rd instar larvae in the dark for 2 to 5 h. Concentration = FI50 value (1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC

250

Opender Koul

CHALCONE 4,4′,6′-TRIHYDROXY-2′-METHOXY

C16H14O5 (286.27)

M.p. : 248°

OH

OCH3

HO

OH

O

(1)

(1)

SOURCE: Gnaphalium affine D. Don, cudweed (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

3.8 × 10–7 mol/cm2

Feeding inhibition = 50%

1. Treatment to 3rd instar larvae in the dark for 2 to 5 h. Concentration = FI50 value (1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC

Insect Antifeedants

CHAMAEDROXIDE

251

C20H22O7 (374.39)

M.p. : 255–257°

O

[α]20 D : +37.1° (Pyridine)

O O

HO

O O O

(1)

(1, 2) SOURCE: Teucrium chaemaedrys L., wall germander (Labiatae)

(1,2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Glass fiber disk choice test

Glass fiber disk choice test

Conc. / Dose

Efficacy

Remarks

100 ppm

Feeding inhibition = 31.8%

10 ppm

Feeding inhibition = 25.6%

1. Treatment to final stadium larvae prestarved for 4 h. Treatment was never longer than 18 h so that not more than 50% of any disk was consumed. (2)

100 ppm

Feeding inhibition = 18.9%

10 ppm

Feeding inhibition = 16.7%

2. Treatment to final stadium larvae prestarved for 4 h. Treatment was never longer than 18 h so that not more than 50% of any disk was consumed. (2)

(1) Eguren, L., Perales, A., Fayos, J., Rodriguez, B., Savona, G., and Piozzi, F. (1982) J. Org. Chem., 47, 4157. (2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry, 28, 1069.

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252

Opender Koul

CHAPARRIN

C20H28O7 (380.44)

M.p. : 306–308° [α]26 D : 45.2° (pyridine)

OH HO HO

O H

HO

O

O

H

(1, 2, 3)

(1, 2, 4)

SOURCE: Castela nicholsoni Hook, cockspur (Simaroubeaceae)

(2, 3)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Leaf disk choice test

19.8 µg/cm2

Efficacy Feeding inhibition = 30–60% after 2 days.

Remarks Treatment to 3rd instar larvae. (3)

(1) Geissman, T.A. and Chandorkar, K.R. (1961) J. Org. Chem., 26, 1217. (2) Geissman, T.A. and Ellestad, G.A. (1962) Tetrahedron Lett., 3, 1083. (3) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K. (1987) J. Nat. Prod., 50, 442. (4) Davidson, T.A., Hollands, T.R., Mayo, P.D., and Nisbet, M. (1965) Can. J. Chem., 43, 2996.

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Insect Antifeedants

CHAPARRINONE

253

C20H26O7 (378.42)

M.p. : 238–242° [α]D : –47° (pyridine)

OH HO HO

O H

O

O

O

(1, 2, 3)

(1, 2, 4)

SOURCE: Simaba multiflora A. Juss., cajurana (Simaroubaceae)

(2, 3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Heliothis virescens (Fab.) (Tobacco budworm)

Leaf disk choice test

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

3. Epilachna varivestis Muls. (Mexican bean beetle)

Test Insect

Efficacy

Remarks

15.0 µg/cm2

Feeding inhibition = 95%

1. Treatment to 3rd instar larvae. Concentration = PC95. (3)

Leaf disk choice test

6.0 µg/cm2

Feeding inhibition = 95%

2. Treatment to 3rd instar larvae. Concentration = PC95. (3)

Whole leaf application

200 ppm

Feeding inhibition = 82.4%

100 ppm

Feeding inhibition = 78.0%

3. Treatment to 4th instar larvae prestarved for 2 h. Treatment duration = 24 h. Data calculated from Reference 4. (4)

(1) Polonsky, J. and Bourguignon-Zylber, N. (1965) Bull. Soc. Chim. Fr., 2793. (2) Arisawa, M., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1983) J. Nat. Prod., 46, 218. (3) Clocke, J.A., Arisawa, M., Handa, S.S., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1985) Experientia, 41, 7. (4) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

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254

Opender Koul

CHELIDONIC ACID

C7H4O6 (184.10)

HOOC

O

M.p. : 262° (dec.)

COOH

O

(1)

(1)

SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 0.15%

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 50 to 75 aphids at random in each treatment. Concentration = EC50. (2)

(1) Bough, W.A. and Gander, J.E. (1972) Phytochemistry, 11, 209. (2) Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) J. Chem. Ecol., 7, 273.

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Insect Antifeedants

CHICORIC ACID

255

C22H18O12 (474.37)

M.p. : 206°

OH

[α]D : +383.5° (MeOH) COOH OH H

C

OOC

COO

C

H

COOH HO

OH

(1)

(1, 2) SOURCE: Cichorium intybus L., chicory (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Schistocerca gregaria (Forsk.) (Desert locust)

Test Method Glass fiber disk test

Conc. / Dose

Efficacy

Remarks

1.06% dry weight

Feeding inhibition = 92.6%

Treatment to 2- to 3day-old adults of either sex (1:1).

0.83% dry weight

Feeding inhibition = 72.3%

0.48% dry weight

Feeding inhibition = 56.6%

(1) Scarpati, M.L. and Oriente, G. (1958) Tetrahedron, 4, 43. (2) Rees, S.B. and Harborne, J.B. (1985) Phytochemistry, 24, 2225.

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Data calculated from Reference 2. (2)

256

Opender Koul

CHLORDIMEFORM

C10H13N2Cl (196.67)

M.p. : 35° B.p : 156–157°/0.4 mm n25 D

Cl

: 1.5885

N = CHN

(1, 2)

(1, 2) SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

200 ppm

Feeding inhibition = 50.0%

4493.12 ppm

Feeding inhibition = 95.0%

Treatment to 5th instar larvae without subjecting to prestarvation. Concentration = EC50 value. Concentration = EC95 value. (2)

956.0 ppm

Feeding inhibition = 50.0%

LD50 (rats): 238 mg/kg (i.p.) (1) Schering, A.G. (1964), Ger. Pat. 1172081. (2) Antonious, A.G. and Saito, T. (1981) Appl. Ent. Zool., 16, 328. (3) Robinson, C.P. and Smith, P.W. (1977) J. Toxicol. Environ. Health, 3, 565.

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Treatment to 5th instar larvae prestarved for 24 h. Concentration = EC50 value. (2)

(3)

Insect Antifeedants

15-O-CHLOROBENZOYL BRUCEOLIDE

257

C28H30O11Cl (577.99)

Only spectral data given

OH Cl COOCH3

HO O O

OCO A

H

HO

O

O

H

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Leaf disk choice test

12.0 µg/cm2

6.0 µg/cm2

Efficacy

Remarks

Feeding inhibition = 60–90% after 2 days and 0–30% after 6 days

Treatment to 3rd instar larvae.

Feeding inhibition = 30–60% after 2 days and 0–30% after 6 days

Treatment to 3rd instar larvae.

(1)

(1)

(1) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

258

Opender Koul

15-m-CHLOROBENZOYL BRUCEOLIDE

C28H30O11Cl (577.99)

Only spectral data given

OH COOCH3

HO O O

OCO A

H

HO

O

Cl

O

H

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Leaf disk choice test

12.0 µg/cm2

6.0 µg/cm2

Efficacy

Remarks

Feeding inhibition = 60–90% after 2 days and 0–30% after 6 days

Treatment to 3rd instar larvae.

Feeding inhibition = 30–60% after 2 days and 0–30% after 6 days

Treatment to 3rd instar larvae.

(1)

(1)

(1) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

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Insect Antifeedants

CHLOROGENIC ACID

259

C16H18O9 (354.31) M.p. : 208°

OH

[α]26 D : –35.2° (H2O)

OH

OOCCH = CH COOH

OH

OH OH

(1, 2)

(1, 2) SOURCE: Many dicotyledenous plants Pteridium aquilinum L. Kuhn., bracken fern (Pteridophyte) Salix integra, willow (Salicaceae)

(1, 2, 3) (4) (5)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

0.2%

Feeding inhibition = 50.0%

1. Treatment to 50–75 aphids at random for 24 h.

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

0.35%

Feeding inhibition = 50.0%

2. Treatment to 50–75 aphids at random for 8 h. Concentrations = EC50 values. (3)

3. Pieris brassicae (L.) (Large white butterfly)

Leaf disk no-choice test

1.4 × 10–2 M

Feeding ratio = 2.51

3. Treatment to 2nd day 5th instar unstarved larvae. Ratio of < 20 is effective deterrence. (4)

4. Lochmaea capreae cribrata Solsky. (Leaf beetle)

Filter paper disk test

0.1 M

Feeding inhibition = 100%

0.01 M

Considerably less feeding than controls.

4. Treatment to adult beetles starved for 24 h. No nibbling of test material observed at 0.1 M. (5)

0.1 M

As much feeding as in controls

5. Plagiodera versicolora distincta Baly. (Salicaceae leaf beetle)

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Filter paper disk test

5. Treatment to adult beetles starved for 24 h. (5)

260

Opender Koul

6. Altica oleraceae (L.) (Alder leaf beetles)

Filter paper disk test

0.01 M

Feeding inhibition = 100%

6. Treatment to adult beetles starved for 24 h. (5)

7. Galelucella vittaticollis Baly. (Strawberry leaf beetle)

Filter paper disk test

0.01 M

Considerably less feeding than controls

7. Treatment to adult beetles starved for 24 h. (5)

(1) (2) (3) (4) (5)

Fischer, H.O.L. and Danyschat, G. (1932) Ber. Dtsch. Chem. Ges., 65, 1037. Barnes, H.M., Feldman, J.R., and White, W.V. (1950) J. Am. Chem. Soc., 72, 4178. Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489. Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187. Matsuda, K. and Senbo, S. (1986) Appl. Ent. Zool., 21, 411.

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Insect Antifeedants

12α-CHLOROMETHYL ROTENONE

261

C23H23O6Cl (442.89) No physical data gven

OCH3 CH3O

O CH2Cl

O O

O

CH2

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 81.1

Treatment given to adults. (1)

2. Tribolium confusum Jacq. Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = Larvae = 132.4 Adults = 138.4

Treatment given to both adults and larvae. (1)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 192.7

Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (1)

(1) Nawrot, J., Harmatha, J., Kostova, I., and Ognyanov, I. (1982) Biochem. Syst. Ecol., 17, 55.

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262

Opender Koul

8′-CHLOROROTENONE

C22H20O6Cl (427.86)

No physical data given

OCH3 CH3O

O

O O

O CH2Cl

C H

CH2

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 142.1

Treatment given to adults. (1)

2. Tribolium confusum Jacq. Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = Larvae = 116.8 Adults = 133.8

Treatment given to both adults and larvae. (1)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 115.9

Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (1)

(1) Nawrot, J., Harmatha, J., Kostova, I., and Ognyanov, I. (1982) Biochem. Syst. Ecol., 17, 55-57.

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Insect Antifeedants

CICHORIIN

263

C15H16O9 (340.28)

M.p. : 213–215° [α]18 D : –105° (dioxane)

HO O HO

O

OH

OH

O

O

HO

(1, 2)

(1, 2, 3) SOURCE: Cichorium intybus L., chicory (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Schistocerca gregaria (Forsk.) (Desert locust)

Test Method Glass fiber disk test

Conc. / Dose

Efficacy

Remarks

0.168% dry weight

Feeding inhibition = 96.3%

Treatment to 2- to 3day-old adults of either sex (1:1).

0.084% dry weight

Feeding inhibition = 66.9%

Data calculated from Reference 3. (3)

0.011% dry weight

Feeding inhibition = 66.1%

0.001% dry weight

Feeding inhibition = 51.1%

(1) Merz, K. (1932) Arch. Pharm., 270, 476. (2) Head, F. and Robertson, A. (1939) J. Chem. Soc., 1266. (3) Rees, S.B. and Harborne, J.B. (1985) Phytochemistry, 24, 2225.

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264

Opender Koul

CINNAMALDEHYDE

C9H8O (132.15) B.p. : 210°/250 mm

CHO

d20 4

: 1.0497

n20 D

: 1.61949

(1, 2)

(1, 2, 3) SOURCE: Commercial sample Alchornea triplinervia (Spreng.) Muell. Arg., larenjeira (Euphorbiaceae)

(3) (4)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Pieris brassicae (L.) (Large white butterfly)

Leaf disk no-choice test

7.6 × 10–2 M

Feeding ratio = 21.9, considered as strong antifeedant effect.

1. Treatment to 2nd day 5th instar unstarved larvae. (3)

2. Anthonomus grandis Bohem. (Boll weevil)

Artificial diet feeding

10 mg/4 cm2

Feeding ratio = 4.0%

20 mg/4 cm2

Feeding ratio = 4.0%

30 mg/4 cm2

Feeding ratio = 0.0%

2. Treatment to freshly emerged boll weevils. Percent feeding ratio (T/C) value of 0 represents total feeding deterrence and >100 as attraction. (4)

Test Insect

LD50 (rats): 2220 mg/kg (oral)

Efficacy

Remarks

(5)

(1) Bert, L. and Anneguin, R. (1931) Compt. Rend., 192, 1315. (2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 138. (3) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187. (4) Miles, D.H., Hankinson, B.L., and Randle, S.A. (1985) Proc. ACS Symp. Ser., 276, 469. (5) Jenner, P.M., Hagan, E.C., Jean, M.T., Cook, E.L., and Fitzhugh, O.G. (1964) Food Cosmet. Toxicol., 2, 327.

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Insect Antifeedants

CINNAMAMIDE

265

C9H9ON (147.18)

M.p. : 147°

O

H2N

(1, 2)

(1)

SOURCE: Commercial sample Cornopteris decurrentialata, fern (Pteridophte)

(2) (1)

ACTIVITY PROFILE Test Insect Pieris brassicae (L.) (Large white butterfly)

Test Method Leaf disk no-choice test

Conc. / Dose 6.8 × 10–2 M

Efficacy

Remarks

Feeding ratio = 2.42, considered as effective antifeedant.

Treatment to 2nd day 5th instar unstarved larvae. (2)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.

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266

Opender Koul

Trans-CINNAMIC ACID

C9H8O2 (148.16)

M.p. : 133° B.p. : 300°

COOH

(1, 2)

(1)

SOURCE: Synthetic Commercial sample Alchornea triplinervia (Spreng.) Muell. Arg., larenjeira (Euphorbiaceae)

(2) (3) (4)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Incisitermes minor (Hagen) (Western drywood termite)

Paper towel disk test

2. Pieris brassicae (L.) (Large white butterfly)

3. Anthonomus grandis Bohem. (Boll weevil)

Test Insect

LD50 (rats): 2500 mg/kg (oral) (1) (2) (3) (4) (5)

Efficacy

Remarks

0.05 mg/cm2

Feeding inhibition = 23.5%

1. Treatment to immature termites for 6 days. (2)

Leaf disk no-choice test

6.8 × 10–2 M

Feeding ratio = 3.11, considered as effective antifeedant.

2. Treatment to 2nd day 5th instar unstarved larvae. (3)

Artificial diet feeding

30 mg/4 cm2

Feeding ratio = 25.0%

3. Treatment to freshly emerged boll weevils. Percent feeding ratio (T/C) value of 0 represents total feeding deterrence and >100 as attraction. (4)

(5)

Camte, P., Zwingelstein, G., Ville, A., and Mentzer, C. (1957) Compt. Rend., 245, 1144. Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187. Miles, D.H., Hankinson, B.L., and Randle, S.A. (1985) Proc. ACS Symp. Ser., 276, 469. Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

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Insect Antifeedants

CINNAMONITRILE

267

C9H7N (129.16)

M.p. : 20–21° B.p. : 134°/12 mm

N

(1, 2)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Pieris brassicae (L.) (Large white butterfly)

Test Method

Conc. / Dose

Leaf disk no-choice test

7.8 × 10–2 M

Efficacy Feeding ratio = 19.5, considered as strong antifeedant.

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.

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Remarks Treatment to 2nd day 5th instar unstarved larvae. (2)

268

Opender Koul

5-CINNAMOYL-9-ACETYL-TAXICIN I

C31H38O8 (538.64)

M.p. : 163–165°

OH

[α]25 D : +186° (CHCl3)

OAc

O

OH OH

O CH2 O

(1)

(1, 2) SOURCE: Taxus baccata Nutt., yew tree (Taxaceae)

(1, 2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 115.5

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 103.4 Larvae = 129.0

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 79.0

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Appendino, G., Gariboldi, P., Pisetta, A., Bombardelli, E., and Gabetta, B. (1992) Phytochemistry, 31, 4253. (2) Daniewski, W.M., Gumulka, M., Anczewski, W., Masnyk, M., Bloszyk, E., and Gupta, K.K. (1998) Phytochemistry, 49, 1279.

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Insect Antifeedants

6-CINNAMOYL-5-HYDROXY-2, 2-DIMETHYLCHROMAN

O

269

C20H17O3 (305.39)

No physical data given

OH

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nutgrass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dual choice test

Glass fiber disk dual choice test

Efficacy

Remarks

100 ppm

Feeding inhibition = 52.0%

10 ppm

Feeding inhibition = 41.0%

100 ppm

Feeding inhibition = 68.0%

10 ppm

Feeding inhibition = 32.0%

1. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae pre-starved for 4 h. (1) 1. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae pre-starved for 4 h. (1)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

270

Opender Koul

13-Trans-CINNAMOYL OXYLUPANINE

C24H30O3N2 (394.51)

M.p. : 166° [α]20 D : +42° (neat)

H O

N

N

O H

O

(1)

(1, 2) SOURCE: Synthetic Also isolated from Lupinus angustifolius L., European blue lupine and L. polyphyllus Lindl., lupine (Fabaceae)

(2) (1)

ACTIVITY PROFILE Test Insect Choristoneura fumiferana (Clemens) (Spruce budworm)

Test Method

Conc. / Dose

Paper penicillin disk assay

Efficacy

Remarks

1.3 × 103 M

Feeding inhibition = 95.0%

1. Treatment to 6th instar larvae. (2)

0.1 × 103 M

Feeding inhibition = 54.0%

0.01 × 103 M

Feeding inhibition = 2.0%

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Bentley, M.D., Leonard, D.E., Reynolds, E.K., Leach, S., Beck, A.B., and Murakoshi, I. (1984) Ann. Entomol. Soc. Am., 77, 398.

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Insect Antifeedants

CINNAMYL ALCOHOL

271

C9H10O (134.17)

M.p. : 33° B.p. : 72.6°/1 mm

OH

n20 D

: 1.58190

(1)

(1, 2) SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Pieris brassicae (L.) (Large white butterfly)

LD50 (rats): 2000 mg/kg (oral)

Test Method

Conc. / Dose

Leaf disk no-choice test

7.5 × 10–2 M

Efficacy Feeding ratio = 4.76

Remarks Treatment to 2nd day 5th instar unstarved larvae. Ratio <20 considered as effective antifeedant. (2)

(3)

(1) Meerwein, H. and Schmidt, R. (1925), Ann., 444, 221. (2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

272

Opender Koul

CINNZEYLANINE

C22H34O8 (426.50)

M.p. : 265–267° [α]27 D : +45° (CH3OH)

α- OAc OH

HO

HO

O

OH HO

(2)

(1, 2) SOURCE: Persea indica Spreng., Indian bay (Lauraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk choice assay

1000 ppm

Efficacy Feeding inhibition index = 23.41

Remarks Treatment to 3rd instar larvae for 1 day. Feeding inhibition index value of < 23 highly deterrent. (1)

(1) Gonzalez-Coloma, A., Terrero, D., Parales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem., 44, 296. (2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 97.

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Insect Antifeedants

CINNZEYLANOL

273

C20H32O7 (384.46)

M.p. : 125–127° [α]15 D : +18° (CH3OH)

α - OH OH

HO

HO

O

OH HO

(2)

(1, 2) SOURCE: Persea indica Spreng, Indian bay (Lauraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

LD50 (mice): 11.98 mg/kg (i.p.)

Test Method

Conc. / Dose

Leaf disk choice assay

1000 ppm

Efficacy Feeding inhibition index = 7.28

Remarks Treatment to 3rd instar larvae for one day. Feeding inhibition index value of < 23 highly deterrent. (1)

(1)

(1) Gonzalez-Coloma, A., Terrero, D., Parales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem., 44, 296. (2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 96.

© 2005 by CRC Press LLC

274

Opender Koul

EPI – CINNZEYLANOL

C20H32O7 (384.47)

Only spectral data given

β - OH OH

HO

HO

O

OH HO

(1)

(1)

SOURCE: Persea indica Spreng., Indian bay (Lauraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk choice assay

1000 ppm

Efficacy Feeding inhibition index = 6.6

Remarks Treatment to 3rd instar larvae for 1 day. Feeding inhibition index value of < 23 highly deterrent. (1)

(1) Gonzalez-Coloma, A., Terrero, D., Parales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem., 44, 296.

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Insect Antifeedants

CINNZEYLANONE

275

C20H30O7 (382.45)

Only spectral data given

O OH

HO

HO

O

OH HO

(1)

(1)

SOURCE: Persea indica Spreng., Indian bay (Lauraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk choice assay

1000 ppm

Efficacy Feeding inhibition index = 9.41

Remarks Treatment to 3rd instar larvae for 1 day. Feeding inhibition index value of < 23 considered highly deterrent. (1)

LD50 (mice): >25 mg/kg (i.p.)

(1)

(1) Gonzalez-Coloma, A., Terrero, D., Parales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem., 44, 296.

© 2005 by CRC Press LLC

276

Opender Koul

CITROLIN

C26H28O6 (436.50)

M.p. : 305°

O

O

O

O

O

O

(1, 2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect 1. Eldana saccharina Walker (Sugar cane borer)

2. Maruca testulalis (Geyer) (Bean pod borer)

Test Method Leaf disk choice assay

Leaf disk choice assay

Conc. / Dose

Efficacy

Remarks

100 µg/disk

Feeding inhibition = 55 ± 21%

10 µg/disk

48 ± 10%

1. Treatment to 12-h pre-starved late 5th instar larvae. (2)

100 µg/disk

Feeding inhibition = 66 ± 5%

2. Treatment to late 5th instar larvae. (2)

(1) Dreyer, D.L. (1965) Tetrahedron, 21, 75. (2) Hassanali, A., Bentley, M.D., Sitayo, E.N.O., Njoroge, P.E.W., and Yatagai, M. (1986) Insect Sci. Applic., 7, 495.

© 2005 by CRC Press LLC

Insect Antifeedants

d-CITRONELLIC ACID

277

C10H18O2 (170.25)

M.p. : 257° [α]D : +21° (acetone) : +10.3° (CHCl3)

COOH

(1)

(1, 2) SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Incistermes minor Hagen (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk test

0.05 mg/cm2

Efficacy Feeding inhibition = 11.4%

Remarks Treatment to immature termites for 6 days. Data calculated from Reference 2. (2)

LD50 (rats): 2610 mg/kg (oral)

(3)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

278

Opender Koul

(–) CLAUSSEQUINONE

HO

C16H14O5 (286.28)

M.p. : 189–194° (dec.) (197–205°)

O

O

OCH3

O

(1, 2)

(1)

SOURCE: Cyclolobium clausseni Benth. (Fabaceae) C. vecchii A. Samp.

(1)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Artificial diet feeding

Conc. / Dose 6.5 µg/g

Efficacy Feeding inhibition = 50.0%

Remarks Treatment to 24-h starved 3rd instar larvae. Concentration = EC50 value. (2)

(1) Gottlieb, O.R., deOliveira, A.B., Goncalves, T.M.M., deOliveira, G.G., and Pereira, S.A. (1975) Phytochemistry, 14, 2495. (2) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) J. Chem. Ecol., 11, 1713.

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Insect Antifeedants

CLERODENDRIN–A

279

C31H42O12 (606.66) O

M.p. : 164–165° [α]D : +7.4° (CHCl3)

O

HO

CCOO CH2

O

OAc

OAc OAc

(1)

(1)

SOURCE: Clerodendron tricotomum Thunb., Japanese kusagi (Verbenaceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk choice test

2. Ostrinia nubilalis (Hubner) (European corn borer)

Leaf disk choice test

Test Insect

Efficacy

Remarks

300 ppm

Feeding inhibition = 100%

1. Treatment to 3rd instar larvae. (2)

5000 ppm

Feeding inhibition = 100%

2. Treatment to larvae at random. (2)

3. Euproctis subflava (Bremer) (Oriental tusk moth)

Leaf disk choice test

1000 ppm

Feeding inhibition = 100%

3. Treatment to larvae at random. (2)

(1) Kato, N., Shibayama, M., and Munakata, K. (1973) J. Chem. Soc. Perkin I, 712. (2) Kato, N., Takahashi, M., Shibayama, M., and Munakata, K. (1972) Agric. Biol. Chem., 36, 2579.

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280

Opender Koul

CLERODENDRIN–B

C31H44O12 (608.68) O

M.p. : 207–209° (228–230°) [α]22 D : –66° (CHCl3)

O

HO

CCOO CH2

O

OAc

OAc OAc

(2)

(1, 2) SOURCE: Clerodendron tricotomum Thunb., Japanese kusagi (Verbenaceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk choice test

2. Ostrinia nubilalis (Hubner) (European corn borer)

Leaf disk choice test

Test Insect

Efficacy

Remarks

200 ppm

Feeding inhibition = 100%

1. Treatment to 3rd instar larvae. (1)

5000 ppm

Feeding inhibition = 100%

2. Treatment to larvae at random. (1)

3. Euproctis subflava (Bremer) (Oriental tusk moth)

Leaf disk choice test

1000 ppm

Feeding inhibition = 100%

3. Treatment to larvae at random. (1)

(1) Kato, N., Takahashi, M., Shibayama, M., and Munakata, K. (1972) Agric. Biol. Chem., 36, 2579. (2) Rao, L.J.M., Pereira, J., and Gurudutt, K.N. (1993) Phytochemistry, 34, 572.

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Insect Antifeedants

CLERODIN

281

C24H34O7 (434.53) O

M.p. : 161–162° (164–165°) [α]30 D : –37.6° (EtOH)

O

O

CH2

OAc

OAc

(1) (1, 4)

SOURCE: Clerodendron infortunatum Gaertn., Indian bhat tree (Verbenaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf dip

80 ppm

Feeding inhibition = 100%

1. Treatment to 3rd or 4th instar larvae. (2) This activity was observed at 50 ppm within 2 h in later studies. (3)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk choice test

100 ppm

Feeding inhibition = 74.0% Feeding inhibition = 59.0% Feeding inhibition = 24.0%

2. Treatment to final stadium larvae prestarved for 4 h. Treatment duration = 12 h. (4)

50 ppm 25 ppm

FI50 = 46.4 ppm calculated from Reference 4.

(1) Barton, D.H.R., Cheung, H.T., Cross, A.D., Jackman, L.M., and Martin-Smith, M. (1961) J. Chem. Soc., 5061. (2) Kato, N., Takahashi, M., Shibayama, M., and Munakata, K. (1972) Agric. Biol. Chem., 36, 2579. (3) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045. (4) Cole, M.D., Anderson, J.C., Blaney, W.M., Fellows, L.E., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J. (1990) Phytochemistry, 29, 1793.

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282

Opender Koul

CLERODIN HEMIACETAL

C24H36O8 (452.54)

OH

M.p. : 179–181°

O H

H O H

O

CH2

OAc

OAc

(1, 2)

(1)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk test

Conc. / Dose 50 ppm

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to 3rd instar larvae for 2 h. This activity has been termed as absolute antifeedant effect. (2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1974) Agric. Biol. Chem., 38, 823. (2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

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Insect Antifeedants

CNICIN

283

C20H26O7 (378.42)

M.p. : 143° [α]20 D : +158° (EtOH)

OH OH OCO CH2

CH2OH

CH2

O O

(1, 2)

(1, 2) SOURCE: Centaurea diffusa Lam., thistle (Cynaraceae)

(3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

Treatment given to adults. (3)

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = Larvae = 51–100 Adults = 151–200

Treatment given to both adults and larvae. (3)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Suchy, M., Benesova, V., Herout, V., and Sorm, F. (1960) Chem. Ber., 93, 2449. (2) Suchy, M., Samek, Z., Herout, V., and Sorm, F. (1965) Collect. Chech. Chem. Commun., 30, 3473. (3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin., 24, 27.

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284

Opender Koul

CORONOPILIN

C15H20O4 (264.32)

M.p. : 177–178° [α]21 D : –30.2° (EtOH)

OH

O

CH2

O

O

(1)

(1, 2) SOURCE: Iva xanthifolia Nutt., iva (Asteraceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

Treatment given to adults. (3)

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = Larvae = 51–100 Adults = 51–100

Treatment given to both adults and larvae. (3)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 151–200

Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Herz, W. and Hogenauer, G. (1961) J. Org. Chem., 26, 5011. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin., 24, 27.

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Insect Antifeedants

o-COUMARIC ACID

285

C9H8O3 (164.16)

M.p. : 207–208° (dec.)

COOH

OH

(1, 2)

(1)

SOURCE: Pteridium aquilinum (L.) Kuhn, bracken fern (Pteridophyte)

(2,3)

ACTIVITY PROFILE Test Insect Pieris brassicae (L.) (Large white butterfly)

LD50 (mice): 180 mg/kg (ivn)

Test Method Leaf disk no-choice test

Conc. / Dose

Efficacy

Remarks

6.1 × 10–2 M

Feeding ratio = 1.82

Treatment to 2nd day 5th instar unstarved larvae. Ratio considered as average deterrence. (2)

(4)

(1) Tiemann, F. (1877) Ber., 10, 284. (2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187. (3) Glass, A.D.M. and Bohm, B.A. (1969) Phytochemistry, 8, 371. (4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

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286

Opender Koul

p-COUMARIC ACID

C9H8O3 (164.16)

M.p. : 210–213°

COOH

OH

(1, 2)

(1, 3)

SOURCE: Pteridium aquilinum (L.) Kuhn, bracken fern (Pteridophyte)

(2, 3)

ACTIVITY PROFILE Test Insect Pieris brassicae (L.) (Large white butterfly)

LD50 (mice): 657 mg/kg (ipr.) (1) (2) (3) (4)

Test Method

Conc. / Dose

Efficacy

Remarks

Leaf disk no-choice test

6.1 × 10–2 M

Feeding ratio = 4.54

Treatment to 2nd day 5th instar unstarved larvae. Ratio considered as effective deterrence. (2)

(4)

Ogawa, S. (1927) Bull. Chem. Soc. Jap., 2, 25. Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187. Glass, A.D.M. and Bohm, B.A. (1969) Phytochemistry, 8, 371. Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

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Insect Antifeedants

COUMESTROL

287

C15H8O5 (268.22) M.p. : 385°

OH

HO

O

O

O

(1)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Costelytra zealandica (White) (Scarab beetle)

Artificial diet feeding

2. Heteronychus arator (Fab.) (Black beetle)

Artificial diet feeding

Test Insect

Efficacy

Remarks

200 µg/ml

Feeding inhibition = 17.0%

1. Treatment to 3rd instar larvae after 24-h starvation. (2) Data calculated from Reference 2.

200 µg/ml

Feeding inhibition = 44.0%

2. Treatment to 3rd instar larvae after 24-h starvation. (2) Data calculated from Reference 2.

(1) Bikoff, E.M., Lyman, R.L, Livingston, A.L., and Booth, A.N. (1958) J. Am. Chem Soc., 80, 3969. (2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

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288

Opender Koul

CRISPATINE

C16H23O5N (309.36)

[α]20 D : +40.7° (EtOH)

H H

C

C

O

C

C O

M.p. : 137–138°

C O

OH H

O

CH2

N

(1)

(1, 2) SOURCE: Crotalaria crispata F. Muell et Benth., crotalaria (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Choristoneura fumiferana (Clemens) (Spruce budworm)

Test Method Paper penicillin disk test

Conc. / Dose 1.6 × 103 M

Efficacy Feeding inhibition = 65.0%

Remarks Treatment to 6th instar larvae. (2)

(1) Culvenor, C.C.J. and Smith, C.W. (1963) Aust. J. Chem., 16, 239. (2) Bentley, M.D., Leonard, D.E., Stoddard, W.F., and Zalkow, L.H. (1984) Ann. Entomol. Soc. Am., 77, 393.

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Insect Antifeedants

CUCURBITACIN–B

289

C32H46O8 (558. 71)

O OH

M.p. : 180–182° [α]25 D : +87.5° (EtOH)

OAc O OH HO

O

(1, 2)

(1, 2) SOURCE: Citrullus colocynthis L., cucurbit (Cucurbitaceae) And many other cucurbit plants.

(1) (3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks 1. Treatments to adults until 25–50% disks were eaten. (1) 2. Treatments to adults until 25–50% disks were eaten. (1) 3. Treatments to 4th instar larvae until 25–50% disks were eaten. (1) 4. Treatments to 5th instar larvae until 25–50% food was eaten. (1) 5. Treatments to adults until 25–50% disks were eaten. (1) 6. Treatment to bilaterally ablated beetles for 24 h. EC50 = 0.1 µM. (4) Data calculated from Reference 4.

1. Popillia japonica Newman (Japanese beetle)

Leaf disk dual choice test

25 µg/cm diameter

Feeding inhibition = 57.0%

2. Cerotoma trifurcata (Foster) (Bean leaf beetle)

Leaf disk dual choice test

50 µg/cm diameter

Feeding inhibition = 64.9%

3. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk dual choice test

50 µg/cm diameter

Feeding inhibition = 90.2%

4. Tenebrio molitor L. (Yellow mealworm)

Oat meal flake assay

50 µg/37 mg flakes

Feeding inhibition = 91.4%

5. Nauphoeta cinerea (Oliver) (Cinereous cockroach)

Flake treatment assay

50 µg/37 mg flakes

Feeding inhibition = 91.4%

6. Diabrotica virgifera virgifera LeConte (Western corn rootworm)

Disk choice test

10.7 nmol/30 mm2

Feeding inhibition = 38.9%

(1) Tallamy, D.W., Stull, J., Ehresman, P., Gorski, P.M., and Mason, C.E. (1997) Environ. Entomol., 26, 678. (2) (1982) Dictionary of Organic Compounds, Vol. 2, Chapman & Hall, New York, p. 1315. (3) Lavie, D. and Glotter, E. (1977) Forts. Chem. Organ. Naturstoffe., 29, 306. (4) Chyb, S., Eichenseer, H., Hollister, B., Mullin, C.A., and Frazier, J.L. (1995) J. Chem. Ecol., 21 313.

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290

Opender Koul

CUCURBITACIN–E

C32H44O8 (556. 69)

M.p. : 234° [α]20 D : –64.3° (CHCl3)

O OH

OAc O OH HO

O

(1, 2)

(1, 2) SOURCE: Commercial sample

(1)

ACTIVITY PROFILE Test Insect Hylobius pales (Herbst.) (Pales weevil)

Test Method Twig dip choice assay

Conc. / Dose 300 ppm

Efficacy

Remarks

Feeding inhibition = 63.7%

Treatments to 22–65 mg body weight weevils for 24 h. (1) Data calculated from Reference 1.

(1) Salom, S.M., Carlson, J.A., Ang, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407. (2) (1982) Dictionary of Organic Compounds, Vol. 2, Chapman & Hall, New York, p. 1316.

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Insect Antifeedants

ar – CURCUMENE

291

C15H22 (202.34)

B.p. : 137°/17 mm [α]D : –34.3° n20 D

: 1.4989

(1)

(1, 2) SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method

Conc. / Dose

Leaf disk test

10-1 mol./L

Efficacy

Remarks

Feeding inhibition = 85.0%

Treatment to 5th instar larvae for 2 h. (2)

(1) Carter, F.D., Copp, F.C., Sanjiva Rao, B., Simmonsen, J.L., and Subramanian, K.S. (1939) J. Chem. Soc., 1504. (2) Yano, K. (1987) J. Agric. Food Chem., 35, 889.

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292

Opender Koul

CYCLOEPIATALANTIN

C26H28O8 (468.50) M.p. : 310° (dec.) O

O

O

O

O

O

O

(1, 2)

(1)

SOURCE: Severinia buxifolia (Poir.) Tenore., Chinese box orange (Rutaceae)

(2)

ACTIVITY PROFILE Test Insect Plutella xylostella (L.) (Diamondback moth)

Test Method Leaf disk choice test

Conc. / Dose 0.25%

Efficacy Feeding inhibition = 50.0%

Remarks Treatment to 3rd instar larvae. Concentration = EC50 value. (2)

(1) Dreyer, D.L., Bennett, R.D., and Basu, S.C. (1976) Tetrahedron, 32, 2376. (2) Wu, T.S., Leu, Y.L., Chan, Y.Y., Wu, P.L., Kuoh, C.S., Wu, S.J., and Wang, Yu (1997) Phytochemistry, 45, 1393.

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Insect Antifeedants

CYPERAQUINONE

293

C14H10O4 (242.23) M.p. : 182–183°

O

O

O

O

(1)

(1)

SOURCE: Cyperus nipponicus, C. distans L., sedge (Cyperaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk assay

Conc. / Dose

Efficacy

1.7 × 10–7 mol/cm2

Feeding inhibition = 50.0%

Remarks Treatment to 3rd instar larvae up to 5 h. Concentration = EC50 value. (1)

(1) Morimoto, M., Fujii, Y., and Komai, K. (1999) Phytochemistry, 51, 605.

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294

Opender Koul

CYTISINE (sophorine/ulexine)

C11H14ON2 (190. 24)

M.p. : 155° B.p. : 218°/2 mm [α]17 D : –119° (H2O)

NH

N

O

(1,3)

(1, 2) SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Acyrthosiphon pisum (Harris) (Pea aphid)

Test Method

Conc. / Dose

Efficacy

Remarks

Artificial diet feeding

0.00016 ± 0.00004%

Feeding inhibition = 50.0%

Treatment to aphids at random. Concentration = EC50 value. (2)

LD50 (mice): 101 mg/kg (oral) (1) (2) (3) (4)

(4)

Govindachari, T.R., Rajadurai, S., Subramanian, M., and Thyagarajan, B.S. (1957) J. Chem. Soc., 3839. Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045. Murakoshi, I., Fukuchi, K., Haginiwa, J., Ohmiya. S., and Otomasu, H. (1977) Phytochemistry, 16, 1460. Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

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Insect Antifeedants

DANIELLIC ACID

295

C20H28O3 (316.44)

M.p. : 129–130.5° [α]D : –58° (MeOH)

H2C O

O

OH

(1, 3)

(1, 2, 3) SOURCE: Daniellia oliveri (Rolle) Hutch. and Dalz., copaiba balsam (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 0.01%

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to aphids at random. Concentration = EC50 value. (2)

(1) Haeuser, J., and Lombard, R. (1961) Tetrahedron, 12, 205. (2) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249. (3) Mills, J.S. (1973) Phytochemistry, 12, 2479.

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296

Opender Koul

DATURALACTONE

C28H38O7 (486.60)

M.p. : 264–267°

O H OH O O

OH

O

(1,2)

(1)

SOURCE: Datura qyercifolia H.B.K., datura Nicandra physaloides (L.) Gaertn., apple-of-Peru (Solanaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Styropor test

100 ppm

Feeding inhibition = 6.0%

Treatment to early 5th instar larvae. Treatment given in combination with anicandrin. Data calculated from Reference 2. (2)

2. Epilachna varivestis Muls. (Mexican bean beetle)

Bean leaf assay

100 ppm

0.5 mg body weight against 8.9 mg in controls. 2.8 mg body weight against 9.8 mg in controls.

2. Treatment to 4th instar larvae for 48 h. (2)

0.8 mg body weight against 2.1 mg in controls.

3. Treatment to 0 to 3-h-old larvae for 14 days. (2)

10 ppm

3. Tribolium castaneum (Herbst.) (Red flour beetle)

Yeast diet feeding

100 ppm

(1) Kalla, A.K., Raina, M.L., Dhar, K.L., Qurishi, M.A., and Snatzke, G. (1979) Phytochemistry, 18, 637. (2) Ascher, K.R.S., Eliyahu, M., Glotter, E., Goldman, A., Kirson, I., Abraham, A., Jacobson, M., and Schmutterer, H. (1987) Phytoparasitica, 15, 15.

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Insect Antifeedants

297

3-DEACETOXY-2′,3′,20,21,22,23HEXAHYDROSALANNIN

C32H48O7 (544.73)

COOCH3

Only spectral data given

O

COO H

O

H H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy

Remarks

Feeding inhibition = 95.0%

Treatment to freshly molted 3rd instar larvae. Disks examined every 2 h until 95% of control disks were eaten. Concentration = PC95 (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC

298

Opender Koul

10-DEACETYL BACCATIN III

C29H36O10 (544.60)

Only spectral data given

OH O OH HO

OH

O OAc

O

O

(1, 2, 3)

(1, 2)

SOURCE: Taxus baccata Nutt., yew tree (Taxaceae)

(3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 185.0

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 180.2 Larvae = 149.4

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 115.5

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200. (3)

(1) Miller, R.W., Powell, R.G., and Smith, C.R. (1981) J. Org. Chem., 46, 1469. (2) Gabetta, B., De Bellis, P., Pace, R., Appendino, G., Barboni, L., Torregiani, E., Gariboldi, P., and Viterbo, D. (1995) J. Nat. Prod., 58, 1508. (3) Daniewski, W.M., Gumulka, M., Anczewski, W., Masnyk, M., Bloszyk, E., and Gupta, K.K. (1998) Phytochemistry, 49, 1279.

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Insect Antifeedants

6-DEACETYLNIMBIN

299

C28H34O8 (498.57)

COOCH3

M.p. : 208°

O

O

O H3COOC

OH

(1)

(1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

2. Pericallia ricini (Fab.) (Tiger moth)

3. Oxya fuscovittata (Marsh.) (Grasshopper)

Test Method

Conc. / Dose

Leaf disk dual-choice test

1 µg/cm2

Leaf disk dual-choice test

1 µg/cm2

Leaf disk dual-choice test

1 µg/cm2

10 µg/cm2

10 µg/cm2

10 µg/cm2

Efficacy

Remarks

Feeding inhibition = 64.6% Feeding inhibition = 66.9%

1. Treatment to 3rd instar larvae for 24 h. (2)

Feeding inhibition = 64.5% Feeding inhibition = 70.2%

2. Treatment to 3rd instar larvae for 24 h. (2)

Feeding inhibition = 67.6% Feeding inhibition = 79.6%

3. Treatment to 3rd instar larvae for 24 h. (2)

(1) Narayanan, C.R. and Iyer, K.N. (1967) Ind. J. Chem., 5, 460. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., and Gopalakrishnan, G. (1996) J. Chem. Ecol., 22, 1453.

© 2005 by CRC Press LLC

300

Opender Koul

6-DEACETYLNIMBINENE

C26H32O6 (440.54)

M.p. : 141° [α]D20 : +132° (CHCl3)

OCH3 O O

O

O

OH

(1, 2)

(1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Bean leaf choice test

Conc. / Dose 0.082%

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 4th instar larvae for 24 h. Concentration = EC50 (2)

(1) Kraus, W. and Cramer, R. (1981) Chem. Ber., 114, 2375. (2) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd Int. Neem Conf., Rauischholzhausen, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC

Insect Antifeedants

3-DEACETYLSALANNIN

301

C32H42O8 (554.68)

O

M.p. : 214–215° [α]D20 : +134° (CHCl3)

COOCH3

O

O H

O

HO H

O

(1, 2)

(1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method

Conc. / Dose

Bean leaf choice test

Efficacy

Remarks

0.0027%

Feeding inhibition = 50.0%

Treatment to 4th instar larvae for 24 h. Concentration = EC50 (2)

0.05%

Feeding inhibition = 100%

At this level of treatment absolute antifeedance maintained until 16 h post-treatment. Data calculated from Reference 3. (3)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118. (2) Kraus, W. and Cramer, R. (1981) Liebigs Ann. Chem., 2381. (3) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd Int. Neem Conf., Rauischholzhausen, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC

302

Opender Koul

DEACETYL SERGEOLIDE

C23H26O10 (462.45)

M.p. : 295–300° (dec.) [α]D24 : –145° (pyridine)

OH COOCH3

HO O

OH

O O

H O

O

H

(1, 2)

(1, 3)

SOURCE: Picrolemma pseudocoffea Ducke. (Simaroubaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Leaf disk choice test

12.0 µg/cm2

Feeding inhibition = 60–90% after 6 days of treatment.

3.0 µg/cm2

Feeding inhibition = 60–90% after 2 days of treatment and 0–30% after 6 days of treatment.

Efficacy

Remarks Treatment to 3rd instar larvae.

(2)

(1) Polonsky, J., Bhatnagar, S., and Moretti, C. (1984) J. Nat. Prod., 47, 994. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442. (3) Moretti, C., Polonsky, J., Vuilhorgne, M., and Prange, T. (1982) Tetrahedron Lett., 23, 647.

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Insect Antifeedants

DEACETYL VISMINONE–A

O

303

C21H24O5 (356.42)

OH

M.p. : 161–164°

OH

OCH3 OH

(1, 2)

(1)

SOURCE: Psorospermum febrifugum Spach., Christmas berry (Clusiaceae)

(1)

ACTIVITY PROFILE Test Insect Locusta migratoria (L.) (Migratory locust)

Test Method Glass fiber disk test

Conc. / Dose 10–3 M

Efficacy Feeding inhibition = 69.22%

Remarks Treatment to last instar larvae. (2)

(1) Botta, B., Monache, F.D., Monache, G.D., Bettolo, G.B.M., and Ogukawa, J.V. (1983) Phytochemistry, 22, 539. (2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem. Ecol., 11, 1593.

© 2005 by CRC Press LLC

304

Opender Koul

DEACYLADENOSTYLONE

C15H22O3 (250.34)

M.p. : 177–178° [α]D24 : 108.8° (CHCl3)

OH

O O

(1, 2)

(1)

SOURCE: Adenostyles alliariae (Gouan) Kern., grauer alpino (Asteraceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 45

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 112 Larvae = 103

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 37

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200. (2)

(1) Harmatha, J., Samek, Z., Novotny, L., Herout, V., and Sorm, F. (1969) Collect. Czech. Chem. Commun., 34, 1739. (2) Nawrot, J., Harmatha, J., and Novotny, L. (1984) Biochem. Syst. Ecol., 12, 99.

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Insect Antifeedants

DEAMINOACYLTAXINE–A

305

C24H34O8 (450.53)

M.p. : 204–206° [α]D25 : –116.9° (CHCl3)

OH

O

OH

AcO OH

OAc

(1, 2)

(1)

SOURCE: Taxus baccata Nutt., yew tree (Taxaceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 110.3

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 112.3 Larvae = 129.1

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 73.6

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200. (2)

(1) Appendino, G., Cravotto, G., Enriu, R., Jakupovic, J., Gariboldi, P., Bombardelli, E., and Gabetta, B. (1994) Phytochemistry, 36, 407. (2) Daniewski, W.M., Gumulka, M., Anczewski, W., Masnyk, M., Bloszyk, E., and Gupta, K.K. (1998) Phytochemistry, 49, 1279.

© 2005 by CRC Press LLC

306

Opender Koul

DECANOIC ACID (Capric acid)

C10H20O2 (172.26)

M.p. : 31.5° B.p. : 268–270° n40 D

: 1.42855

COOH

(1, 2)

(1, 2)

SOURCE: Synthetic Hibiscus syriacus L., rose-of-sharon (Malvaceae)

(3) (4)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Incisitermes minor (Hagen) (Western drywood termite)

Paper towel disk test

2. Anthonomus grandis Bohem. (Boll weevil)

Plate bioassay

Test Insect

Efficacy

Remarks

0.05 mg/cm2

Feeding deterrence = 11.7%

1. Treatment to immature termites. Duration of treatment = 6 days. (3)

100 µg per feeding site

Feeding of 64% of controls after 2 h and 63% after 6 h in males, and 69% and 64%, respectively, in females.

2. Treatment given to adult weevils. (4)

LD50 (mice): 129 ± 5.4 mg/kg (i.v.) (1) (2) (3) (4) (5)

Kao, C.H. and Ma, S.-Y. (1931) J. Chem. Soc., 2046. Sisido, K., Kazama, Y., Kodama, H., and Nozaki, H. (1959) J. Am. Chem. Soc., 81, 5817. Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) J. Chem. Ecol., 13, 1087. Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

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(5)

Insect Antifeedants

n-DECYL GALLATE

307

C17H26O5 (310.39)

No data given

COO

OH

HO HO

(1)

(1)

SOURCE: Commercial sample

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

16 ppm

Feeding deterrence = 50.0%

1. Treatment to aphids at random Concentration = EC50 (1)

2. Acyrthosiphon pisum (Harris) (Pea aphid)

Artificial diet feeding

40.7 ppm

Feeding deterrence = 50.0%

2. Treatment to aphids at random. Concentration = EC50 (1)

3. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

484 ppm

Feeding deterrence = 50.0%

3. Treatment to aphids at random. Concentration = EC50 (1)

(1) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.

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308

Opender Koul

DEHYDROABIETIC ACID

C20H28O2 (300.44)

M.p. : 172–173° [α]D20 : +62° (EtOH)

COOH

(1)

(1) SOURCE: Pinus banksiana Lamb., jack pine (Pinaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

1. Neodiprion dubiosus Schedl. (Brownhead jack pine saw fly)

Pine needles and twig application

1 mg/ml

2. Neodiprion lecontei (Fitch) (Redhead pine saw fly)

Pine needles and twig application

3. Neodiprion rugifrons Middleton (Redhead jack pine saw fly)

(1) (2) (3) (4)

Conc. / Dose

Efficacy

Remarks

Feeding deterrence = 57.0% Feeding deterrence = >70.0%

1. Treatment to 3rd or 4th instar larvae for 4 h. (2, 3)

10.6 mg/ml

Feeding deterrence = >70.0%

2. Treatment to 3rd or 4th instar larvae for 4 h. (3)

Pine needles and twig application

6.7 mg/ml

Feeding deterrence = >70.0%

3. Treatment to 3rd or 4th instar larvae for 4 h. (3)

Spray

3 mg/ml

Feeding deterrence = 24.6%

Treatment to 3rd instar larvae. Sprays made on both larvae and the host branches. (4)

13.5 mg/ml

Stork, G. and Schulenberg, J.W. (1962) J. Am. Chem. Soc., 84, 284. Schuh, B.A. and Benjamin, D.M. (1984) J. Chem. Ecol., 10, 1071. Schuh, B.A. and Benjamin, D.M. (1984), J. Econ. Entomol., 77, 802. Ikeda, T., Matsumura, F., and Benjamin, D.M. (1977) J. Chem. Ecol., 3, 677.

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Insect Antifeedants

14,15-DEHYDROAJUGAREPTANSIN

309

C29H42O10 (550.65)

Only spectral data given

O O

H

H

O O

HO O

CH2 OAc OAc

(1)

(1)

SOURCE: Ajuga reptans L., catlins giant (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Glass-fiber disk test

Conc. / Dose

Efficacy

Remarks

25 ppm

Feeding deterrence = 60.0%

100 ppm

Feeding deterrence = 92.0%

Treatment to 6th stadium larvae prestarved for 4 h. Treatment removed either after 50% of disk was consumed or after 14 h. (1)

(1) Bremner, P.D., Simmonds, M.S.J., Blaney, W.M., and Veitch, N.C. (1998) Phytochemistry, 47, 1227.

© 2005 by CRC Press LLC

310

Opender Koul

DEMETHYLGROSSAMIDE

C35H34O8N2 (610.66)

OH

Amorphous powder

OH

NH HN

O

O OH O OH

OCH3

(1)

(1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae)

(1)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method

Conc. / Dose

Paper disk choice test

500 ppm

Efficacy Feeding inhibition index = 29.49

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index value below 20 considered as highly effective deterrent value. (1)

Insect Antifeedants

DEMETHYLHOMOLYCORINE

311

C17H19O4N (301.34)

M.p. : 213–214° (138–140°; 270–272°) [α]D : +96.4° (CHCl3)

N H CH3O

O HO O

(1)

(1, 2) SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae)

(2)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina DelOrza (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose

Efficacy

Remarks

0.4%

Feeding ratio = 20.9%

0.2%

Feeding ratio = 20.0%

0.1%

Feeding ratio = 19.1%

0.05%

Feeding ratio = 22.8%

Treatment to 5th instar larvae after 4 h of pre-starvation. Feeding ratio up to 20% considered as strong feeding deterrence. (2)

(1) Uyeo, S. (1960) c.f. Wildman, The Alkaloids, Ed. Manske, 3, 333. (2) Numata, A., Takemura, T., Ohbayashi, H., Katsuuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983) Chem. Pharm. Bull., 31, 2146.

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312

Opender Koul

DEMISSINE

C50H83O20N (1018.20)

M.p. : 305–308° (Uncor.) [α]D10 : –20° (Pyridine)

N

Xyl - Gal - 2Glu - O H

(1)

(1) SOURCE: Solanum demissum Lindl., solanum (Solanaceae) Commercial sample

(1) (2)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method

Conc. / Dose

Sensillum response recording

0.4% wet weight

Efficacy Feeding inhibition = 50.0%

Remarks Treatment to adult beetles. Concentration = EC50 (2)

(1) Kuhn, R. and Low, I. (1947) Chem. Ber., 80, 406. (2) Mitchel, B.K. and Harrison, G.D. (1985) J. Chem. Ecol., 11, 73.

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Insect Antifeedants

313

C21H29N2O⊕ (325.48)

DENATONIUM BENZOATE

M.p. : 166–170°

+ NHCOCH2N CH2

(1, 2)

(2)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Myzus persicae (Sulzer) (Green peach aphid)

Test Method Leaf disk nochoice test

Conc. / Dose 250 ppm

Efficacy

Remarks

Feeding inhibition = 66.0%

Treatment to 2-dayold larvae for 48 h. Data calculated from Reference 1. (1)

(1) Perera, M.T.M.D.R., Armstrong, G., and Naylor, R.E.L. (1995) Trop. Agric. Res., 7, 39. (2) (1982) Dictionary of Organic Compounds, Vol. 2, Chapman & Hall, New York, p. 1482.

© 2005 by CRC Press LLC

314

Opender Koul

14-DEOXYANDROGRAPHOLIDE

C20H30O4 (334.46) O

M.p. : 175° [α]D : –30.7° (MeOH)

O

CH2

HO CH2OH

(2)

(1, 2) SOURCE: Andrographis paniculata (Burm. f.) Wall. ex. Nees, king of bitters (Acanthaceae)

(1)

ACTIVITY PROFILE Test Insect Plutella xylostella (L.) (Diamondback moth)

Test Method

Conc. / Dose

Leaf disk nochoice test

100 µg/leaf disk of 2 cm diameter

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 4th stadium larvae for 24 h. Insects were pre-starved for 3 h. Concentration = EC50 value calculated from Reference 1. (1)

(1) Hermawan, W., Nakajima, S., Ritsuko, T., Fujisaki, K., and Nakasuji, F. (1997) Appl. Entomol. Zool., 32, 551. (2) Balmain, A. and Connolly, J.D. (1973) J. Chem. Soc. Perkin Trans I, 1247.

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Insect Antifeedants

DEOXYEPILIMONOL

315

C26H32O7 (456.51)

M.p. : 300–305° [α]D : +61° (Acetone)

O O

O

O

O O OH

(1)

(1, 2) SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

100 µg/cm2

Feeding inhibition = 75.1%

Treatment to 4th instar larvae for 6 to 8 h. (2)

31.7 µg/cm2

Feeding inhibition = 36.9%

10 µg/cm2

Feeding inhibition = 1.4%

Approximate FI50 = 49.8 µg/cm 2. Calculated from Reference 2.

(1) Barton. D.H.R., Pradhan, S.K., Sternhell, S., and Templeton, J.F. (1961) J. Chem Soc., 255. (2) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.

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316

Opender Koul

8-DEOXYLACTUCIN

C15H16O4 (260.29)

M.p. : 143–148°

O

H H H CH2OH

CH2

O

O

(1,2)

(2)

SOURCE: Cichorium intybus L., chicory (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Schistocerca gregaria (Forsk.) (Desert locust)

Test Method Glass fiber disk test

Conc. / Dose

Efficacy

Remarks

0.49% dry weight

Consumption of treated food = 19.4%

Treatment to 2- to 3-day-old adults of either sex (1:1) (2)

0.36% dry weight

Consumption of treated food = 14.1%

0.24% dry weight

Consumption of treated food = 24.5%

0.22% dry weight

Consumption of treated food = 53.7%

(1) Pyrek, J.S. (1977) Roczniki Chemii., 51, 2165. (2) Rees, S.B., and Harborne, J.B. (1985) Phytochemistry, 24, 2225.

© 2005 by CRC Press LLC

It was not possible to calculate EC50 from this data.

Insect Antifeedants

DEOXYLIMONIN

317

C26H30O7 (454.52) O

M.p. : 331–336° [α]D : –39° (CHCl3)

O

O

O

O O O

(1)

(1,2) SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect 1. Eldana saccharina Walker (Sugar cane borer)

2. Maruca testulalis (Geyer) (Bean pod borer)

Test Method Leaf disk test

Leaf disk test

Conc. / Dose

Efficacy

Remarks

100 µg/disk

Feeding inhibition = 83 ± 9%

10 µg/disk

Feeding inhibition = 81 ± 10%

1. Treatment to 12-h starved late 5th instar larvae. (2)

1 µg/disk

Feeding inhibition = 66 ± 11%

100 µg/disk

Feeding inhibition = 46 ± 14%

10 µg/disk

Feeding inhibition = 56 ± 14%

2. Treatment to late 5th instar larve prestarved for 12 h. (2)

(1) Barton, D.H.R., Pradhan, S.K., Sternhell, S., and Templeton, J.F. (1961) J. Chem. Soc., 255. (2) Hassanali, A., Bentley, M.D., Sitayo, E.N.O., Njoroge, P.E.W., and Yatagai, M. (1986) Insect. Sci. Applic., 7, 495.

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318

Opender Koul

DEOXYLIMONOL

C26H33O7 (457.22)

M.p. : 250–252°

O O O

O

O O OH

(1,2)

(1)

SOURCE: Synthetic Also isolated from Citrus paradisi Macfad., grapefruit (Rutaceae)

(2) (1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

100 µg/cm2

Feeding inhibition = 71.0%

1. Treatment to 4th instar larvae for 6–8 h. (2)

31.7 µg/cm2

Feeding inhibition = 30.4%

(1) Bennett, R.D., and Hasegawa, S. (1982) Phytochemistry, 21, 2349. (2) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.

© 2005 by CRC Press LLC

Insect Antifeedants

DEOXYVASICINE

319

C11H12N2 (172.23)

M.p. : 99–100°

N

N

(1)

(1)

SOURCE: Adhatoda vasica L., vasaka (Acanthaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Aulacophora foveicollis (Lucas) (Red leaf beetle)

2. Epilachna vijintioctopunctata (Fab.) (Brinjal beetle)

Test Method Leaf spray test

Leaf spray test

Conc. / Dose

Efficacy

0.05%

Feeding inhibition = 67.8%

1. Treatment to adults for 24 h.

0.1%

Feeding inhibition = 30.4%

Data calculated from Reference 1. (1)

0.05%

Feeding inhibition = 57.1%

2. Treatment to adults for 24 h.

0.1%

Feeding inhibition = 60.2%

Data calculated from Reference 1. (1)

(1) Saxena, B.P., Tikku, K., Atal, C.K., and Koul, O. (1986) Insect Sci. Applic., 7, 489.

© 2005 by CRC Press LLC

Remarks

320

Opender Koul

DERRICIN

C21H22O3 (322.40)

O

Physical data not given

OH

O

(1,2)

(1)

SOURCE: Lonchocarpus neuroscapha Bentt., coroa piaca (Fabaceae)

(2)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nutgrass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dualchoice test

Glass fiber disk dualchoice test

Efficacy

Remarks

100 ppm

Feeding inhibition = 72.0%

10 ppm

Feeding inhibition = 54.0%

1. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (2)

100 ppm

Feeding inhibition = 75.0%

10 ppm

Feeding inhibition = 56.0%

2. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (2)

(1) Rao, J.M., Subrahmanyam, K., and Rao, K.V.J. (1976) Ind. J. Chem., 14B, 339. (2) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

Insect Antifeedants

DESACETYLOARCTOLIDE

321

C15H17O5 (277.34)

Only spectral data given

O

H

HO

O

CH2

O

OH CH2

(1, 2)

(1)

SOURCE: Arctotis grandis Thunb., African daisy (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius L. (Grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 98.7

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient Adults = 194.9 Larvae = 114.3

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 164.5

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200. (2)

(1) Samek, Z., Holub, M., Grabarczyk, H., and Drozdz, B. (1977) Collect. Czech. Chem. Commun., 42, 2217. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk. Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC

322

Opender Koul

4-DESOXY-8-EPI-IVANGUSTIN

C15H20O2 (232.32)

[α]D24 : +35.2°

O O

CH2

(1)

(1, 2) SOURCE: Eupatorium quadrangularae L., joe-pye-weed (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Atta cephalotes (L.) (Leaf cutter ant)

Test Method Rye flake forced choice test

Conc. / Dose 0.6 mg/ml or 12 µg/flake

Efficacy

Remarks

Feeding inhibition = 29.2%

Treatment to adult workers. (2)

(1) Bohlmann, F., Mahanta, P.K., Jakupovic, J., Rastogi, R.C., and Natu, A.A. (1978) Phytochemistry, 17, 1165. (2) Hubert, T.D., Okunade, A.L., and Weimer, D.F. (1987) Phytochemistry, 26, 1751.

© 2005 by CRC Press LLC

Insect Antifeedants

1-DETIGLOYL-3-DEACETYLSALANNIN

323

C27H36O7 (472.58)

Only spectral data given

COOCH3 O

OH

H

O HO H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

25 µg/cm2

Feeding inhibition = 50.0%

>400 µg/cm2

Feeding inhibition = 95.0%

Treatment to freshly moulted 3rd instar larvae. Disks examined every 2 h until 95% of control disks were eaten. Concentrations = PC50 and PC95 values, respectively. (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC

324

Opender Koul

1-DETIGLOYL-3-DEACETYL-20,21,22, 23-TETRAHYDROSALANNIN

C27H40O7 (476.61)

Only spectral data given

COOCH3 O

OH

H

O HO H

O

(1,2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Conc. / Dose 50 µg/cm2

Efficacy

Remarks

Feeding inhibition = 95.0%

Treatment to freshly molted 3rd instar larvae. Disks examined every 2 h until 95% of control disks were eaten. Concentration = PC95 value. (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC

Insect Antifeedants

1-DETIGLOYL-22,23-DIHYDROAZADIRACHTIN

325

C30H41O15 (641.61)

No physical data given

COOCH3 HO

O

OH

OH

O

O OH

AcO H3COOC

O

H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to starved final stadium larvae (24 to 36 h old). Bioassays terminated after the larvae had eaten approximately 50% of one of the disks. (1)

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leafworm)

Glass fiber disk choice test

1.0 ppm

Feeding inhibition = 75.0%

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk choice test

1.0 ppm

Feeding inhibition = 56.0%

3. Heliothis virescens (Fab.) (Tobacco budworm)

Glass fiber disk choice test

1.0 ppm

Feeding inhibition = 58.0%

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Glass fiber disk choice test

1.0 ppm

Feeding inhibition = 40.0%

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. App., 55, 149.

© 2005 by CRC Press LLC

326

Opender Koul

1-DETIGLOYL-3-O-METHYL-3DEACETYLSALANNIN

C28H38O7 (486.61)

Only spectral data given

COOCH3 O

OH

H

O CH3O

H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Conc. / Dose 400 µg/cm2

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to freshly moulted 3rd instar larvae. Disks examined every 2 h until 95% of control disks were eaten. Concentration = PC50 value. (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC

Insect Antifeedants

1-DETIGLOYL-3-O-METHYL-3DEACETYL-20,21,22,23TETRAHYDROSALANNIN

327

C28H42O7 (490.64)

Only spectral data given

COOCH3 O

OH

H

O

CH3O

H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Conc. / Dose 50 µg/cm2

Efficacy

Remarks

Feeding inhibition = 95.0%

Treatment to freshly moulted 3rd instar larvae. Disks examined every 2 h until 95% of control disks were eaten. Concentration = PC95 value. (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC

328

Opender Koul

DHURRIN

C14H17O7N (311.28)

M.p. : 165° [α]D20 : –62.7° (Alcohol)

H CH2OH O

O

OH

C

OH CN OH

H

OH

(1)

(1) SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 0.16%

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 50–75 aphids at random. Concentration = EC50 value. (2)

(1) Towers, G.H.N., McInnes, A.G., and Neish, A.C. (1964) Tetrahedron, 20, 71. (2) Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) J. Chem. Ecol., 7, 273.

© 2005 by CRC Press LLC

Insect Antifeedants

DIACETOXY DIBENZOYLOXY-1,4-DI HYDROXY-DIHYDRO-β-AGAROFURAN

329

C33H38O11 (610.66)

Oil [α]D25 : –39.7° (CHCl3)

AcO OBz

OH

OBz

O HO

OAc

(1)

(1) SOURCE: Maytenus canariensis (Loes) Kunk. & Sund., peralillo (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy Feeding deterrent

Remarks Treatment to larvae. No quantitative percentage inhibition given. (1)

(1) Gonzalez, A.G., Jimenez, I.A., Ravelo, A.G., Sazatornil, J.G., and Bazzochi, I.L. (1993) Tetrahedron, 49, 697.

© 2005 by CRC Press LLC

330

Opender Koul

6α-12-DIACETOXY-2β,9α-DI (β-FURAN CARBONYLOXY)-4α-HYDROXY-1β-2METHYLBUTANOYLOXY-β-DIHYDRO AGAROFURAN

O COO

AcO

C33H39O14 (659.66)

Amorphous powder [α]D14 : 70.8° (CHCl3)

OCO

O

OOC

O OAc

OH

(1)

(1) SOURCE: Euonymus bungeanus Max., winter berry (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect Pieris rapae (L.) (Imported cabbage worm)

Test Method Leaf feeding

Conc. / Dose

Efficacy

200 ppm

Feeding inhibition = 67.0%

Treatment to larvae for 48 h

500 ppm

Feeding inhibition = 33.0%

Treatment to larvae pre-starved for 3 h. (1)

(1) Tu, Y.Q., Wu, D.G., Zhou, J., Chen, Y.Z., and Pan, X.F. (1990) J. Nat. Prod., 53, 603.

© 2005 by CRC Press LLC

Remarks

Insect Antifeedants

6α-12-DIACETOXY-1β,9α-DI (β-FURAN CARBONYLOXY)-4α-HYDROXY-2β-2METHYLBUTANOYLOXY-β-DIHYDRO AGAROFURAN

O COO

AcO

331

C34H42O14 (674.70)

M.p. : 145–146° [α]D14 : 43.07° (CHCl3)

O OOC OCO

O OAc

OH

(1)

(1) SOURCE: Euonymus bungeanus Max., winter berry (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect Pieris rapae (L.) (Imported cabbage worm)

Test Method Leaf feeding

Conc. / Dose

Efficacy

200 ppm

Feeding inhibition = 31.0%

Treatment to larvae for 48 h

500 ppm

Feeding inhibition = 28.0%

Treatment to larvae pre-starved for 3 h. (1)

(1) Tu, Y.Q., Wu, D.G., Zhou, J., Chen, Y.Z., and Pan, X.F. (1990) J. Nat. Prod., 53, 603.

© 2005 by CRC Press LLC

Remarks

332

Opender Koul

6α-12-DIACETOXY-1β,2β,9α-TRI (β-FURANCARBONYLOXY)-4αHYDROXY-β-DIHYDROAGAROFURAN

C34H42O14 (684.65)

Amorphous powder [α]D14 : 83.94° (CHCl3)

O

O COO

AcO

OOC

O OOC

O OAc

OH

(1)

(1) SOURCE: Euonymus bungeanus Max., winter berry (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect Pieris rapae (L.) (Imported cabbage worm)

Test Method Leaf feeding

Conc. / Dose

Efficacy

200 ppm

Feeding inhibition = 42.0%

Treatment to larvae for 48 h

500 ppm

Feeding inhibition = 22.0%

Treatment to larvae pre-starved for 3 h. (1)

(1) Tu, Y.Q., Wu, D.G., Zhou, J., Chen, Y.Z., and Pan, X.F. (1990) J. Nat. Prod., 53, 603.

© 2005 by CRC Press LLC

Remarks

Insect Antifeedants

DIACETOXY TRIBENZOYLOXY-4HYDROXY-DIHYDRO-β-AGAROFURAN

333

C40H42O12 (714.76)

M.p. : 174–175° [α]D25 : +52.7° (CHCl3)

OAc OBz

BzO

OBz

O HO

OAc

(1)

(1) SOURCE: Maytenus canariensis (Loes) Kunk. & Sund., peralillo (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy Feeding deterrent

Remarks Treatment to larvae. No quantitative percent inhibition given. (1)

(1) Gonzalez, A.G., Jimenez, I.A., Ravelo, A.G., Sazatornil, J.G., and Bazzochi, I.L. (1993) Tetrahedron, 49, 697.

© 2005 by CRC Press LLC

334

Opender Koul

2α,7β-DIACETOXY-15-ISOPIMARENE 3β,8β-DIOL

C24H38O6 (422.56)

M.p. : 174–176°

OH CH2

AcO

OAc

HO

(1)

(1)

SOURCE: Satureja gilliesii (Grah.) Briq., savory (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy Feeding inhibition ratio = 0.27 ± 0.09

Remarks Treatment to 3rd instar larvae. Concentration = EC50 value. (1)

(1) Labbe, C., Castillo, M., Fainia, F., Coll, J., and Connolly, J.D. (1994) Phytochemistry, 36, 735.

© 2005 by CRC Press LLC

Insect Antifeedants

6,19 – DIACETYLTEUMASSILIN

335

C24H34O7 (434.53)

M.p. : 155–156° [α]D20 : –19.3° (CHCl3)

O

OH

O OAc

OAc

(1)

(1, 2) SOURCE: Teucrium massiliense L., purple germander (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Helicoverpa armigera (Hubner) (Gram pod borer)

Test Method Glass fiber disk choice test

Glass fiber disk choice test

Conc. / Dose

Efficacy

Remarks

100 ppm

Feeding deterrence = 32.2%

10 ppm

Feeding deterrence = 21.7%

1. Treatment to final stadium larvae starved for 4 h. Treatment was never longer than 18 h so that at no stage more than 50% of any disk was consumed. (2)

100 ppm

Feeding deterrence = 63.2%

10 ppm

Feeding deterrence = 16.9%

2. Treatment to final stadium larvae as above. (2)

(1) Savona, G., Bruno, M., Piozzi, F., Servettaz, O., and Rodriguez, B. (1984) Phytochemistry, 23, 849. (2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry, 28, 1069.

© 2005 by CRC Press LLC

336

Opender Koul

1,12-DI-O-ACETYLTRICHILIN–B

C39H50O15 (758.88)

O

OAc

OAc

[α]D22 : +0.8° (MeOH)

O

AcO O

O AcO

OH

OCO

(1)

(1, 2) SOURCE: Melia azedarach L., chinaberry (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

400 ppm

Feeding deterrent

1. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (2)

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice test

400 ppm

Feeding deterrent

2. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (2)

Test Insect

Efficacy

Remarks

Concentration = Threshold level for deterrence

(1) Nakatani, M., Huang, R.C., Okamura, H., Naoki, H., and Iwagawa, T. (1994) Phytochemistry, 36, 39. (1) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

Insect Antifeedants

DIACETYLVILASININE

337

C30H40O7 (512.64)

M.p. : 157–158°

O

AcO

AcO

OH O

(1)

(1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Bean leaf test

Conc. / Dose 13 ppm

Efficacy Feeding deterrence = 50%

Remarks Treatment to 4th instar larvae. (2)

(1) Kraus, W. and Cramer, R. (1981) Liebigs Ann. Chem., 2381. (2) Kraus, W. (2002) In H. Schmutterer (ed.), The Neem Tree, 2nd edition, The Neem Foundation, Mumbai, India, pp. 39–111.

© 2005 by CRC Press LLC

338

Opender Koul

β-γ-DIAMINOBUTYRIC ACID

C4H10O2N2 (118.14)

M.p. : 222–223° (HCl) [α]D : +7.9° (H2O)

CH2COOH

H2N

C

H

CH2NH2

(1, 2)

(1, 2) SOURCE: Lathyrus latifolius L., everlasting pea (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Glass fiber disk test

Conc. / Dose

Efficacy

Remarks

0.25%

Feeding inhibition = 26.0%

0.5%

Feeding inhibition = 61.0%

Final stadium larvae treatment pre-starved for 4 h. Treatment given until 50% of the disk was eaten or 18 h, whichever was achieved first. At lower concentrations this compound was phagostimulant. (2)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Bell, E.A., Perera, K.P.W.C., Nunn, P.B., Simmonds, M.S.J., and Blaney, W.M. (1996) Phytochemistry, 43, 1003.

© 2005 by CRC Press LLC

Insect Antifeedants

DIAMINOGUANIDINE HYDRAZONE

339

C21H20O3N6F8 (556.42)

H

No physical data given

H

=

NH OF2CF2CH

CH = N.N.(CH3)2N.CO.CNHN = CH

HCF2F2O

(1, 2)

(1, 2)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Cramer) (Southern armyworm)

Test Method Leaf disk test

Conc. / Dose 8.6 ppm

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to larvae. Concentration = EC50 value. (1)

(1) Addor, R.W., Wright, D.P. Jr., Siddens, J.K., and Hand, J.J. (1986) U.S. patent 4575560, 12 pp.

© 2005 by CRC Press LLC

340

Opender Koul

2,3-DIAMINOPROPANOIC ACID

C3H8O2N2 (104.11)

M.p. : 97° (begins to melt at this temperature)

COOH

H

C

NH2

CH2NH2

(1)

(1)

SOURCE: Acacia spp. (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Anacridium melanorhodon arabafrum (Dirsh.) (Tree locust)

Test Method Glass fiber disk test

Conc. / Dose

Efficacy

Remarks

0.5% of disk weight

Feeding inhibition = 30.0–60.0%

1. Treatment to 3rd to 6th instar larvae at random.

5.0% of disk weight

Feeding inhibition = 91.0–100.0% (2)

2. Locusta migratoria migratorioides (R & F) (Migratory locust)

Glass fiber disk test

1.0% of disk weight

(1) (1983) Merck Index, p. 431. (2) Evans, C.S. and Bell, E.A. (1971) Phytochemistry, 18, 1807.

© 2005 by CRC Press LLC

Feeding inhibition = 61.0–90.0%

2. Treatment to male 5th instar larvae. (2)

Insect Antifeedants

14-15-DIHYDROAJUGAPITIN

341

C29H44O10 (552.66)

M.p. : 212–214°

O H

[α]D20 : –40° (CHCl3)

O H

H H

HO

COO O

CH2 OCOCH3 OCOCH3

(1)

(1, 2) SOURCE: Ajuga pseudoiva (L.) Schreber, African ajuga (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding ratio = 0.11 ± 0.04 (ratio calculated when 50% of control disk area was consumed)

0.1 µg/cm2

Feeding ratio = 0.22 ± 0.08

Treatment to newly ecdysed 5th instar larvae. Ratio of < 0.5 considered as excellent feeding inhibition value. (2)

0.01 µg/cm2

Feeding ratio = 0.32 ± 0.10

0.001 µg/cm2

Feeding ratio = 0.46 ± 0.20

(1) Camps, F., Coll, J., and Dargallo, O. (1984) Phytochemistry, 23, 387. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC

342

Opender Koul

22,23-DIHYDROAZADIRACHTIN

C35H46O16 (722.74)

Only spectral data given

COOCH3

O O

OH

O

OH

O

O OH

AcO H3COOC

O

H

O

(1, 2)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to 24- to 36-h-old starved final stadium larvae. Bioassay terminated after the larvae had consumed about 50% of one of the disks. (2)

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 100%.

Glass fiber disk no-choice test

1 ppm

Feeding inhibition = 77.8%.

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 100%.

Glass fiber disk no-choice test

1 ppm

Feeding inhibition = 87.3%.

Glass fiber disk choice test

1 ppm

Feeding inhibition = 87.3%.

Glass fiber disk no-choice test

1 ppm

Feeding inhibition = 67.0%.

Glass fiber disk choice test

1 ppm

Feeding inhibition = 74.0%.

3. Heliothis virescens (Fab.) (Tobacco budworm)

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Deterrence calculated from Reference 2 for nochoice assay run for 8 to 9 h.

(1) Bilton, J.N., Broughton, H.B., Jones, P.S., Ley, S.V., Lidert, Z., Morgan, E.D., Rzepa, H.S., Sheppard, R.N., Slawin, A.M.Z., and Williams, D.J., Tetrahedron, 43, 2805. (2) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149.

© 2005 by CRC Press LLC

Insect Antifeedants

343

[11 RS]-22,23-DIHYDROAZADIRACHTININ

C35H46O16 (722.74)

Only spectral data given

COOCH3

O O

O

OH

H

OH O

O H

O

OH

AcO H3COOC

H

O

(1, 2)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to 24- to 36-h-old starved final stadium larvae. Bioassay terminated after the larvae had consumed about 50% of one of the disks. (2)

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 96.0%.

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 45.0%.

3. Heliothis virescens (Fab.) (Tobacco budworm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 21.0%.

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 11.0%.

(1) Bilton, J.N., Broughton, H.B., Jones, P.S., Ley, S.V., Lidert, Z., Morgan, E.D., Rzepa, H.S., Sheppard, R.N., Slawin, A.M.Z., and Williams, D.J., Tetrahedron, 43, 2805. (2) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149.

© 2005 by CRC Press LLC

344

Opender Koul

22,23-DIHYDROAZADIRACHTOL

C28H37O14 (597.59)

Only spectral data given

COOCH3 HO

O

OH

OH

O

O OH

HO H3COOC

O

H

O

(1)

(2)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to 24- to 36-h-old starved final stadium larvae. Bioassay terminated after the larvae had consumed about 50% of one of the disks. (1) Approximate EC50 calculated = < 1.0 ppm. Deterrence calculated from Reference 1 for nochoice assay run for 8 to 9 h.

Glass fiber disk choice test

1 ppm

Feeding inhibition = 63.0%

Glass fiber disk nochoice test

1 ppm

Feeding inhibition = 47.4%

Glass fiber disk choice test

1 ppm

Feeding inhibition = 60.0%

Glass fiber disk nochoice test

1 ppm

Feeding inhibition = 51.3%

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149. (2) Ley, S.V. (1990) In E. Frehse (ed.), Pesticide Chemistry, VCH, New York, p. 97.

© 2005 by CRC Press LLC

Insect Antifeedants

DIHYDROCARYOPTIN

345

C27H38O9 (506.59)

CH2

M.p. : 198.5–199.5° [α]D : –63° (CHCl3)

O H

H

O H

AcO H O

CH2 OAc OAc

(1)

(1)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 80 ppm

Efficacy

Remarks

Feeding inhibition = 100% within 2 h

Treatment to 3rd instar larvae. The larvae eventually starve to death. The compound termed as absolute antifeedant. (2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1973) Phytochemistry, 12, 1833. (2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC

346

Opender Koul

DIHYDROCARYOPTINOL

C25H36O8 (464.55)

CH2

M.p. : 204–205° [α]D : –73° (CHCl3)

O H

H

O H

HO O

CH2 OAc OAc

(1)

(1)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

100 ppm

Efficacy

Remarks

Feeding inhibition = 100% within 2 h

Treatment to 3rd instar larvae. The larvae eventually starve to death. The compound termed as absolute antifeedant. (2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1974) Phytochemistry, 13, 1019. (2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC

Insect Antifeedants

DIHYDROCLERODIN–I

347

C24H36O7 (436.54)

M.p. : 169–170° [α]D24 : –10.9° (CHCl3)

O H

H

O H

O

CH2 OAc OAc

(1, 2)

(1, 2)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae) Ajuga parviflora Benth, ajuga (Labiatae)

(1, 2, 3)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 50 ppm

Efficacy

Remarks

Feeding inhibition = 100% within 2 h

Treatment to 3rd instar larvae. The larvae eventually starve to death. The compound termed as absolute antifeedant. (3)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1974) Agric. Biol. Chem., 38, 823. (2) Beauchamp, P.S., Bottini, A.T., Caselles, M.C., Dev, V., Hope, H., Larter, M., Lee, G., Mathela, C.S., Melkani, A.B., Miller, P.D., Miyatake, M., Pant, A.K., Raffel, R.J., Sharma, V.K. and Wyatt, D. (1996) Phytochemistry, 43, 827. (3) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC

348

Opender Koul

DIHYDROCEDRELONE

C26H32O5 (424.54)

M.p. : 216° [α]D30 : –55.5° (CHCl3)

O

O O

O OH

(1, 2)

(1)

SOURCE: Synthetic Also isolated from Cedrela toona Roxb., cedro toona (Cedrelaceae)

(1) (2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding inhibition = 49.5%

Treatment to 3rd instar larvae for 24 h. (2)

5 µg/cm2

Feeding inhibition = 57.1%

Approximate EC50 = 1.2 µg/cm2

10 µg/cm2

Feeding inhibition = 70.5%

50 µg/cm2

Feeding inhibition = 67.7%

Calculated from Reference 2.

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari, G.N. (1995) J. Chem. Ecol., 21, 1586.

© 2005 by CRC Press LLC

Insect Antifeedants

DIHYDROCEDRELONE METHYL ETHER

349

C27H34O5 (438.57)

Only spectral data given

O

O O

O OCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding inhibition = 43.5%

Treatment to 3rd instar larvae for 24 h. (2)

5 µg/cm2

Feeding inhibition = 44.5%

Approximate EC50 = 8.8 µg/cm2

10 µg/cm2

Feeding inhibition = 56.5%

50 µg/cm2

Feeding inhibition = 64.2%

Calculated from Reference 2.

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari, G.N. (1995) J. Chem. Ecol., 21, 1586.

© 2005 by CRC Press LLC

350

Opender Koul

DIHYDROERGOCRYSTINE

C35H41O5N5 (611.74)

Only spectral data given

OH O

O

N NH

N

O

O

N

NH

(1)

(1)

SOURCE: Commercial sample Basically obtained from Lolium perenne L., ryegrass (Graminaceae) infected with fungus Neotyphodium lolii

(2)

ACTIVITY PROFILE Test Insect Heteronychus arator (Fab.) (Black beetle)

Test Method Artificial diet choice test

Conc. / Dose

Efficacy

Remarks

5 µg/g

Feeding inhibition = 45.5%

Treatment to adults for 96 h. (2)

10 µg/g

Feeding inhibition = 54.8%

(1) Coppi, G. (1992) Ayzneim-Forsch, 42, 1381, 1391. (2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.

© 2005 by CRC Press LLC

Data calculated from Reference 2.

Insect Antifeedants

DIHYDROERGOTAMINE

351

C33H37O5N5 (583.69) OH

M.p. : 239° [α]D20 : –64° (pyridine)

O

O

N N H

N

O

O

N

NH

(1, 2)

(1)

SOURCE: Commercial sample Basically obtained from Lolium perenne L., ryegrass (Graminaceae) infected with fungus Neotyphodium lolii

(2)

ACTIVITY PROFILE Test Insect Heteronychus arator (Fab.) (Black beetle)

Test Method Artificial diet choice test

Conc. / Dose

Efficacy

Remarks

5 µg/g

Feeding inhibition = 60.0%

Treatment to adults for 96 h. (2)

20 µg/g

Feeding inhibition = 60.0%

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.

© 2005 by CRC Press LLC

Data calculated from Reference 2.

352

Opender Koul

22,23-DIHYDRO-23-α,β-ETHOXY AZADIRACHTIN

C37H50O17 (766.79)

Only spectral data given

COOCH3

O O

O

OH

OH

O OC2H5 O OH

AcO H3COOC

O

H

O

(1) SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to 24- to 36-h-old starved final stadium larvae. Bioassay terminated after the larvae had consumed about 50% of one of the disks. (1)

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 66.0%

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 62.0%

3. Heliothis virescens (Fab.) (Tobacco budworm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 64.0%

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 54.0%

EC50 = < 1.0 ppm

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149.

© 2005 by CRC Press LLC

Insect Antifeedants

DIHYDROISOLONCHOCARPIN

O

353

C20H20O3 (308.36)

No physical data given

O

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nutgrass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dualchoice test

Glass fiber disk dualchoice test

Efficacy

Remarks

100 ppm

Feeding inhibition = 75.0%.

10 ppm

Feeding inhibition = 42.0%.

1. Treatment to 24- to 36-h-old starved final stadium larvae for 5 h. Larvae prestarved for 4 h. (2)

100 ppm

Feeding inhibition = 23.0%.

10 ppm

Feeding inhibition = 33.0%.

2. Treatment to 24- to 36-h-old starved final stadium larvae for 5 h. Larvae prestarved for 4 h. (2)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

354

Opender Koul

DIHYDROISOPIMPINELLIN

C13H12O5 (248.23)

M.p. : 162–163°

OCH3

O

O

O

OCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

100 ppm

Feeding ratio = 8.0%

10 ppm

Feeding ratio = 15.0%

5 ppm

Feeding ratio = 67.0%

(1) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar larvae. Ratio between 0 and 20% considered as strong inhibitory effect. (1)

Insect Antifeedants

22,23-DIHYDRO-23-α,β-ISOPROPOXY AZADIRACHTIN

355

C38H52O17 (780.44)

Only spectral data given

COOCH3

O O

O

OH

OH

O OPr O

O OH

AcO H3COOC

H

O

(1) SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to 24- to 36-h-old starved final stadium larvae. Bioassay terminated after the larvae had consumed about 50% of one of the disks. (1)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 94.0%

Glass fiber disk nochoice test

1 ppm

Feeding inhibition = 96.7%

Deterrence calculated from Reference 1 for nochoice assay run for 8 to 9 h.

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149.

© 2005 by CRC Press LLC

356

Opender Koul

14,15-DIHYDROJODRELLIN–T

C29H40O10 (548.63) OAc

[α]D20 : –24.4° (CHCl3)

OAc O O

O O O O

(1)

(1)

SOURCE: Scutellaria galericulata L., blue skullcap (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Glass fiber disk choice test

Conc. / Dose

Efficacy

Remarks

100 ppm

Feeding inhibition = 63.0%

50 ppm

Feeding inhibition = 59.0%

25 ppm

Feeding inhibition = 44.0%

Treatment to final stadium larvae prestarved for 4 h. Treatment until either 50% of disk had been consumed or for 12 h. (1)

(1) Cole, M.D., Anderson, J.C., Blaney, W.M., Fellows, L.E., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J. (1990) Phytochemistry, 29, 1793.

© 2005 by CRC Press LLC

Insect Antifeedants

DIHYDROKOKUSAGINE

357

C13H11O4N (245.23)

M.p. : 165–166°

OCH3

O

N

O O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk test

300 ppm

Feeding inhibition = 78.0%

1. Treatment to 3rd instar larvae. (1)

2. Periplaneta americana (L.) (American cockroach)

Sugar pellet test

0.1 mg/ 1.5 g pellet

Feeding inhibition = 100.0%

2. Treatment to adults. (1)

3. Stylopyga rhombifolia (Cockroach)

Sugar pellet test

0.1 mg/ 1.5 g pellet

Feeding inhibition = 85.0%

3. Treatment to adults. (1)

4. Blatella germanica (L.) (German cockroach)

Sugar pellet test

0.1 mg/ 1.5 g pellet

Feeding inhibition = 51.0%

4. Treatment to adults. (1)

(1) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC

358

Opender Koul

22,23-DIHYDRO-23-β-METHOXY AZADIRACHTIN (vepaol)

C36H48O17 (752.76)

[α]D31 : –23° (CHCl3)

COOCH3

O O

O

OH

OH

O OCH3 O OH

AcO H3COOC

O

H

O

(2)

(1) SOURCE: Synthetic Azadirachta indica A. Juss., neem (Meliaceae)

(1) (2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

3. Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to 24- to 36-h-old starved final stadium larvae. Bioassay terminated after the larvae had consumed about 50% of one of the disks.

Glass fiber disk choice test

1 ppm

Feeding inhibition = 81.0%

No-choice

1 ppm

Feeding inhibition = 67.0%

Glass fiber disk choice test No-choice

1 ppm

Feeding inhibition = 70.0%

Approx. EC50 = < 1.0 ppm.

1 ppm

Feeding inhibition = 43.9%

Glass fiber disk choice test

1 ppm

Feeding inhibition = 64.0%

Deterrence calculated from Reference 1 for nochoice assay run for 8 to 9 h. (1)

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149. (2) Sankaram, A.V.B., Murthy, M.M., Bhaskaraiah, K., Subramanyam, M., Sultana, N., Sharma, H.C., Leuschner, K., Ramaprasad, G., Sitaramaiah, S., Rukmini, C., and Rao, P.U. (1987) In H.Schmutterer and K.R.S. Ascher (eds.), Natural Pesticides from Neem and Other Tropical Plants, 3rd Int. Neem Conf., Nairobi, pp. 127–148.

© 2005 by CRC Press LLC

Insect Antifeedants

[11 RS]-22,23-DIHYDRO-23-α,βMETHOXYAZADIRACHTININ

359

C36H48O17 (752.76)

Only spectral data given

COOCH3

O O

O

OH

H

OH O

O OCH3

O

OH

AcO H3COOC

H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Heliothis virescens (Fab.) (Tobacco budworm)

3. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to 24- to 36-h-old starved final stadium larvae. Observations recorded after 1 h. (1)

Glass fiber disk choice test No-choice

1 ppm

Feeding inhibition = 41.7%

1 ppm

Feeding inhibition = 75.0%

Glass fiber disk choice test No-choice

1 ppm

Feeding inhibition = 38.5%

1 ppm

Feeding inhibition = 61.9%

Glass fiber disk choice test

1 ppm

Feeding inhibition = 61.6%

Deterrence calculated from Reference 1 for nochoice assay run for 8 to 9 h.

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149.

© 2005 by CRC Press LLC

360

Opender Koul

[11 RS]-22,23-DIHYDRO-23-α,βPHENYLTHIOAZADIRACHTININ

C41H50O16S (830.85)

No physical data given

COOCH3

O O

O

OH

H

OH O

O SPh

O

OH

AcO H3COOC

H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to 24- to 36-h-old starved final stadium larvae. Bioassay terminated after the larvae had consumed about 50% of one of the disks. (1)

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 37.0%

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 32.0%

3. Heliothis virescens (Fab.) (Tobacco budworm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 32.0%

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 6.0%

Approximate EC50 calculated = 2.0 ppm except in case of H. armigera.

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149.

© 2005 by CRC Press LLC

Insect Antifeedants

2′,3′-DIHYDROSALANNIN

361

C34H46O9 (598.73)

Only spectral data given

O

O

O

O O

O AcO H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Conc. / Dose 200 µg/cm2

Efficacy

Remarks

Feeding inhibition = 95.0%

Treatment to freshly molted 3rd instar larvae. Disks examined every 2 h until 95% of control disks were eaten. Concentration = PC95 value. (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC

362

Opender Koul

2,3-DIHYDRO WITHAFERIN–A

C28H40O6 (472.62)

OH

H O

M.p. : 225–227° (229–230°) [α]D : +8° (CHCl3)

O

H

O

O OH

(1,2)

(1, 3)

SOURCE: Synthetic Also isolated from Withania sominifera (L.) Dunal., common withania (Solanaceae)

(2, 3)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm))

Test Method Styropor method

Conc. / Dose

Efficacy

Remarks

1000 ppm

Feeding inhibition = 5.8%

Treatment to early 5th instar larvae for 48 h. (2)

100 ppm

Feeding inhibition = 11.0%

Data calculated from Reference 2.

50 ppm

Feeding inhibition = 9.5%

(1) Yarden, A. and Lavie, D. (1962) J. Chem. Soc., 2925. (2) Ascher, K.R.S., Eliyahu, M., Glotter, E., Goldman, A., Kirson, I., Abraham, A., Jacobson, M., and Schmutterer, H. (1987) Phytoparasitica, 15, 15. (3) Lavie, D., Glotter, E., and Shuo, Y. (1965) J. Org. Chem., 30, 1774.

© 2005 by CRC Press LLC

Insect Antifeedants

2,3-DIHYDRO WITHANOLIDE–E

363

C28H40O7 (488.62)

M.p. : 264–265° (273–275°) [α]D : –42°

OH O

O

OH

O

OH O

(1, 2)

(1)

SOURCE: Synthetic Also isolated from Physalis peruviana L., Peruvian groundcherry (Solanaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Styropor method

100 ppm

Feeding inhibition = 95.7%

1. Treatment to early 5th instar larvae for 48 h. Data calculated from Reference 2. (2)

2. Epilachna varivestis Mulsant (Mexican bean beetle)

Bean leaf test

1000 ppm

Feeding inhibition determined by loss in weight to 1.5 mg against 11.7 mg gain in controls Feeding inhibition determined by loss in weight to 1.3 mg against 12 mg in controls Feeding inhibition = 44.0%

2. Treatment to 4th instar larvae for 48 h.

250 ppm

3. Tribolium castaneum (Herbst.) (Red flour beetle)

Yeast diet feeding

500 ppm

Loss in weight due to starvation. (2)

3. Treatment to 0 to 3-h-old larvae. (2)

(1) Glotter, E., Abraham, A., Gunzberg, G., and Kirson, I. (1977) J. Chem. Soc. Perkin Trans I, 341. (2) Ascher, K.R.S., Eliyahu, M., Glotter, E., Goldman, A., Kirson, I., Abraham, A., Jacobson, M., Schmutterer, H. (1987) Phytoparasitica, 15, 15.

© 2005 by CRC Press LLC

364

Opender Koul

DIHYDROXANTHOTOXIN

C12H10O4 (218.21)

O

O

M.p. : 159–160°

O

OCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

500 ppm

Feeding ratio = 18%

300 ppm

Feeding ratio = 38%

Efficacy

Remarks Treatment to 3rd instar larvae for 90 m. Ratio = 0–20% strong feeding inhibition. (1)

100 ppm

Feeding ratio = 62%

(1) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC

Insect Antifeedants

2′,4′-DIHYDROOXYCHALCONE

HO

365

C15H12O3 (240.26)

M.p. : 149–150° (142–143°)

OH

O

(1, 2)

(1)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dualchoice test

Efficacy

Remarks

500 ppm

Feeding inhibition = 59.0%

100 ppm

Feeding inhibition = 22.0%

1. Treatment to 24- to 36-h-old starved final stadium larvae for 5 h. Larvae prestarved for 4 h. (2)

(1) Adityachaudhury, N., Kirtaniya, C.L., and Mukherjee, B. (1971) Tetrahedron, 27, 2111. (2) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

366

Opender Koul

2,7-DIHYDROXY-3 (3′-METHOXY-4′-HYDROXY)5-METHOXYISOFLAVONE

C17H14O7 (330.29)

M.p. : 232°

OH O

O

HO O

O

OH

(1, 2)

(1, 2)

SOURCE: Wedelia biflora (L.) DC., sami scandent shrub (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Anthonomous grandis Bohem. (Boll weevil)

Test Method Paper disk test

Conc. / Dose 2.0%

Efficacy

Remarks

Feeding inhibition = 71.0%

Treatment to weevils. Data calculated on the basis of punctures of test paper per number of punctures of control paper. (1)

(1) Miles, D.H., Chittawong, V., Hedin, P.A., and Kokpol, U. (1993) Phytochemistry, 32, 1427. (2) Mabry, T.J., Markham, K.R., and Thomas, M.B. (1970) The Systemic Identification of Flavonoids, Academic, New York.

© 2005 by CRC Press LLC

Insect Antifeedants

2,5-DIHYDROXYMETHYL-3,4DIHYDROXY PYRROLIDINE (DMDP)

C6H13O4N (163.17)

[α]D20 : + 56.4° (H2O)

OH

HO

HOH2C

367

N H

CH2OH

(1)

(1, 2) SOURCE: Derris elliptica Benth., derris plant (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Locusta migratoria (L.) (Migratory locust)

Glass fiber disk test

10–2 M

Feeding inhibition = 80.0 ± 13.34% with sucrose and 90.0 ± 10.01% with fructose.

1. Treatment to early 5th instar larvae. (2)

2. Schistocerca gregaria (Forsk.) (Desert locust)

Glass fiber disk test

10–2 M

Feeding inhibition = 100% with sucrose

2. Treatment to 5th instar larvae. (2)

3. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk test

4 × 10–2 M

Feeding inhibition = 61.4 ± 16.41% with sucrose

3. Treatment to last instar larvae. (2)

4. Spodoptera exempta (Walker) (Nutgrass armyworm)

Glass fiber disk test

4 × 10–2 M

Feeding inhibition = 93.3 ± 5.99% with sucrose

4. Treatment to last instar larvae. (2)

(1) Welter, A., Jadot, J., Dardenne, G., Marlier, M., and Casimir, J. (1976) Phytochemistry, 15, 747. (1) Blaney, W.M., Simmonds, M.S.J., Evans, S.V., and Fellows, L.E. (1984) Entomol. Exp. Appl., 36, 209.

© 2005 by CRC Press LLC

368

Opender Koul

E-3- (3,4-DIHYDROXYPHENYL)-N-2[4-HYDROXYPHENYLETHYL]-2PROPENAMIDE

C17H17O4N (299.33)

Only spectral data given

OH

O HO N H HO

(1, 2)

(1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae)

(2)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method Paper disk choice bioassay

Conc. / Dose 7500 ppm

Efficacy Feeding inhibition index value = 14.6

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index value below 20.0 is highly deterrent value. (2)

(1) Sakakibara, I., Katsuhara, I., Ikeya, Y., Hayashi, K., and Mitsuhashi, H. (1981) Phytochemistry, 20, 3013. (2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

Insect Antifeedants

11β,5α-DIHYDROXY SILPHINEN-3-ONE

369

C15H22O3 (250.34)

Only spectral data given

OH

OH

O

(1, 2)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method

Conc. / Dose

Efficacy

Remarks

Leaf disk choice bioassay

22.6 µg/cm2

Feeding inhibition = 50.0%

Treatments to newly emerged 4th instar larvae for ≤ 6 h.

Leaf disk no-choice bioassay

11.32 µg/cm2

Feeding inhibition = 50.0%

Treatments to newly emerged 4th instar larvae for 24 h. Concentration = FI50 value. (1)

(1) Gonzalez-Coloma, A., Gutierrez, C., Cabrera, R., and Reina, M. (1997) J. Agric. Food Chem., 45, 946. (2) Gonzalez-Coloma, A., Reina, M., Cabrera, R., Castanera, P., and Gutierrez, C. (1995) J. Chem. Ecol., 21, 1255.

© 2005 by CRC Press LLC

370

Opender Koul

DIMBOA

C9H9O5N (211.17)

H3CO

O

OH

N

O

M.p. : 156–157° (dec.)

OH

(1, 2)

(1)

SOURCE: Zea mays L., maize (Graminae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Green bug)

Artificial diet feeding

Conc. / Dose

Efficacy

Remarks

4 nM

Feeding inhibition = 83.7.0%

Treatment to aphids at random.

6 nM

Feeding inhibition = 100.0%

Absolute antifeedant effect achieved within 20 h. (2)

(1) Wahlroos, O. and Virtanen, A.I. (1959) Acta Chem. Scand., 13, 1906. (2) Argandona, V.H., Corcuera, L.J., Niemeyer, H.M., and Campbell, B.C. (1983) Entomol. Exp. Appl., 34, 134.

© 2005 by CRC Press LLC

Insect Antifeedants

DIMBOA-GLUCOSYL

371

C15H19O10N (373.31)

M.p. : 262–263° (dec.)

OH HO

OH

OH H3CO

O

O

N

O

O

OH

(1, 2, 3)

(1, 3)

SOURCE: Zea mays L., maize (Graminae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose

Efficacy

Remarks

4 nM

Feeding inhibition = 71.4%

Treatment to aphids at random.

6 nM

Feeding inhibition = 100.0%

Absolute antifeedant effect achieved within 20 h. (2)

(1) Wahlroos, O. and Virtanen, A.I. (1959) Acta Chem. Scand., 13, 1906. (2) Argandona, V.H., Corcuera, L.J., Niemeyer, H.M., and Campbell, B.C. (1983) Entomol. Exp. Appl., 34, 134. (3) Hofman, J., Hofmanova, O., and Hanus, V. (1969) Tetrahedron Lett., 5001.

© 2005 by CRC Press LLC

372

Opender Koul

3,4-DIMETHOXYBENZALDEHYDE

C9H10O3 (166.18)

M.p. : 44° (58°) B.p. : 172–175°/18 mm

OCH3 OCH3

CHO

(1, 2)

(1, 2)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method Leaf disk dual-choice test

Conc. / Dose 10–1 mol/l

Efficacy

Remarks

Feeding inhibition = 72.8%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 2 h. (1)

or 5 × 10–7 mol/cm2

LD50 (rats): 2000 mg/kg (oral) (1) Yano, K. and Kamimura, H. (1993) Biosci. Biotech. Biochem., 57, 129. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London. (3) Opdyke, D.L.J. (1975) Food Cosmet. Toxicol., 13, 923.

© 2005 by CRC Press LLC

(3)

Insect Antifeedants

3,4-DIMETHOXYBENZAL ALCOHOL

373

C9H12O3 (168.19)

Viscous oil B.p. : 172°/12 mm d17 17

OCH3

: 1.179

OCH3

CH2OH

(1, 2)

(1, 2)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method Leaf disk dual-choice test

Conc. / Dose 10–1 mol/l

Efficacy

Remarks

Feeding inhibition = 61.7%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 2 h. (1)

or 5 × 10–7 mol/cm2

(1) Yano, K. and Kamimura, H. (1993) Biosci. Biotech. Biochem., 57, 129. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC

374

Opender Koul

3,4-DIMETHOXYETHYLBENZENE

C11H14O2 (187.22)

Only spectral data given

OCH3 OCH3

CH2

(1, 2)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method Leaf disk dual-choice test

Conc. / Dose 10–1 mol/l

Efficacy

Remarks

Feeding inhibition = 77.3%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 2 h. (1)

or 5 × 10–7 mol/cm2

(1) Yano, K. and Kamimura, H. (1993) Biosci. Biotech. Biochem., 57, 129.

© 2005 by CRC Press LLC

Insect Antifeedants

3,5-DIMETHOXYPHENOL

375

C8H10O3 (154.16)

M.p. : 44.5° (36–38°) B.p. : 199°/36 mm

OH

H3CO

OCH3

(1)

(1, 2)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding inhibition = 100% up to 3 h

Treatment to adult beetles. (1)

0.5%

Feeding inhibition = 100% up to 22 h

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC

376

Opender Koul

2,6-DIMETHOXYPHENOL

C8H10O3 (154.16)

M.p. : 55–56° B.p. : 262–267°

OH H3CO

OCH3

(1, 2)

(1 ,2)

SOURCE: Synthetic Also found naturally in the essential oil of Artemisia herba-alba var. densiflora Boisd.

(1, 2)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding inhibition = 100% up to 6 h

Treatment to adult beetles. (1)

0.5%

Feeding inhibition = 100% up to 22 h

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC

Insect Antifeedants

3,4-DIMETHOXYPHENOL

377

C8H10O3 (154.16)

M.p. : 79–82° B.p. : 140–142°/0.1 mm n25 D

OH

: 1.5331

OCH3 OCH3

(1)

(1, 2)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk choice test

Conc. / Dose 0.5%

Efficacy

Remarks

Feeding inhibition = 100% up to 24 h

Treatment to adult beetles. (1)

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC

378

Opender Koul

2,3-DIMETHOXYPHENOL

C8H10O3 (154.16)

Oil B.p. : 124–125°/17 mm

OH OCH3

OCH3

(1, 2)

(1, 2)

SOURCE: Synthetic Also isolated from trunkwood of Machaerium kuhlmannii Benth., jacranda (Fabaceae)

(1) (2)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding inhibition = 100% up to 3 h

Treatment to adult beetles. (1)

0.5%

Feeding inhibition = 100% up to 22 h

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC

Insect Antifeedants

2,6-DIMETHOXY-4- (2-PROPENYL) PHENOL

379

C11H14O3 (194.23)

OH

Oil B.p. : 166–168°/10 mm (123–125°/2 mm)

H3CO

OCH3

CH2

(1)

(2)

SOURCE: Synthetic Also isolated from oil of Sassafras albidum (Nutt.) Nees, laurus sassafras roots (Lauraceae)

(1) (2)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding inhibition = 100% up to 6 h

Treatment to adult beetles. (1)

0.5%

Feeding inhibition = 100% up to 6 h

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC

380

Opender Koul

3,4-DIMETHOXYPROPYLBENZENE

C11H16O2 (180.25)

Only spectral data given

OCH3 OCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

10–1 mol/l

Feeding inhibition = 100%

10–2 mol/l

Feeding inhibition = 35.3%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 2 h. (1)

(1) Yano, K. and Kamimura, H. (1993) Biosci. Biotech. Biochem., 57, 129.

© 2005 by CRC Press LLC

Insect Antifeedants

4,6-DIMETHYL-3,7-p-ACETOXYPHENYL -2,8-DIOXO-2H,8H-BENZODIPYRAN

O

O

381

C30H22O8 (510.47)

M.p. : 270°

O

O

CH3OCO

OCOCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk nochoice test

Conc. / Dose Not recorded

Efficacy Feeding inhibition = 83.01%

Remarks Treatment to 4th instar larvae prestarved for 6 h. (1)

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC

382

Opender Koul

4,6-DIMETHYL-3,7-p-BROMOPHENYL -2,8-DIOXO-2H,8H-BENZODIPYRAN

O

C26H18O4Br2 (554.23)

O

M.p. : 291°

O

O

Br

Br

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk nochoice test

Conc. / Dose Not recorded

Efficacy Feeding inhibition = 98.57%

Remarks Treatment to 4th instar larvae prestarved for 6 h. (1)

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC

Insect Antifeedants

4,6-DIMETHYL-3,7-p-CHLOROPHENYL -2,8-DIOXO-2H,8H-BENZODIPYRAN

O

R

383

C26H18O4Cl2 (565.33)

O

M.p. : 285°

O

O

R

R = p-Cl or o-Cl

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk nochoice test

Conc. / Dose Not recorded

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC

Efficacy Feeding inhibition = 97.46% for p-compound and 73.96% for o-compound

Remarks Treatment to 4th instar larvae prestarved for 6 h. (1)

384

Opender Koul

1,3,O,O-DIMETHYL-1-DETIGLOYL3-DEACETYLSALANNIN

C29H40O7 (500.63)

Only spectral data given

O O

OCH3

O H

O CH3O H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Conc. / Dose 50 µg/cm2

Efficacy

Remarks

Feeding inhibition = 95.0%

Treatment to freshly molted 3rd instar larvae. Disks examined every 2 h until 95% of control disks were eaten. Concentration = PC95 value. (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC

Insect Antifeedants

1,3,O,O-DIMETHYL-1-DETIGLOYL3-DEACETYL-20,21,22,23TETRAHYDROSALANNIN

385

C29H44O7 (504.66)

Only spectral data given

O O

OCH3

O H

O CH3O H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Conc. / Dose 100 µg/cm2

Efficacy

Remarks

Feeding inhibition = 95.0%

Treatment to freshly molted 3rd instar larvae. Disks examined every 2 h until 95% of control disks were eaten. Concentration = PC95 value. (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC

386

Opender Koul

4,6-DIMETHYL-3,7-p-HYDROXYPHENYL -2,8-DIOXO-2H,8H-BENZODIPYRAN

O

O

C26H18O6 (426.42)

M.p. : 310°

O

O

HO

OH

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk nochoice test

Conc. / Dose Not recorded

Efficacy Feeding inhibition = 97.36%

Remarks Treatment to 4th instar larvae prestarved for 6 h. (1)

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC

Insect Antifeedants

4,6-DIMETHYL-3,7-DIPHENYL-2,8DIOXO-2H,8H-BENZODIPYRAN

O

387

C26H18O4 (394.43)

O

M.p. : 278°

O

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk nochoice test

Conc. / Dose Not recorded

Efficacy Feeding inhibition = 61.75%

Remarks Treatment to 4th instar larvae prestarved for 6 h. (1)

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC

388

Opender Koul

4,6-DIMETHYL-3,7-p-METHOXYDIPHENYL -2,8-DIOXO-2H,8H-BENZODIPYRAN

O

R

O

C28H22O6 (454.48)

M.p. : 264°

O

O

R

R = p-OCH3 or o-OCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk nochoice test

Conc. / Dose Not recorded

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC

Efficacy Feeding inhibition = 89.84% for p-compound and 83.49% for o-compound

Remarks Treatment to 4th instar larvae prestarved for 6 h. (1)

Insect Antifeedants

3,3′-DI-o-METHYLQUERCETIN

OH

389

C17H14O5 (298.28)

M.p. : 256°

O OH

HO

O

(1, 2)

(1, 2)

SOURCE: Wedelia biflora (L.) DC., sami scandent shrub (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Anthonomus grandis Bohem. (Boll weevil)

Test Method Paper disk choice test

Conc. / Dose 3.5%

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to weevils. Data based on punctures of compound impregnated paper/number of punctures of control disks. (1)

(1) Miles, D.H., Chittawong, V., Hedin, P.A., and Kokpol, V. (1993) Phytochemistry, 32, 1427. (2) Yang, C.H., Braymer, H.D., Murphy, E.L., Chorney, W., Scully, N., and Wender, S.H. (1960) J. Org. Chem., 25, 2063.

© 2005 by CRC Press LLC

390

Opender Koul

4,6-DIMETHYL-3,7-p-NITROPHENYL -2,8-DIOXO-2H,8H-BENZODIPYRAN

O

C26H18O8N2 (486.44)

O

M.p. : >320°

O

O

O2N

NO2

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk nochoice test

Conc. / Dose Not recorded

Efficacy Feeding inhibition = 76.98%

Remarks Treatment to 4th instar larvae prestarved for 6 h. (1)

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC

Insect Antifeedants

DIONCOPHYLLINE–A

391

C24H27O3N (377.48)

M.p. : 215° [α]D20 : –14° (CHCl3)

NH

H3CO

OH

H3CO

(1, 2)

(1, 2)

SOURCE: Triphyophyllum peltatum (Hutch et Dalz.) Airy Shaw and Dioncophyllum thollonii Baill. (Dioncophyllaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Fab.) (Egyptian cotton leaf worm)

Test Method Artificial diet test

Conc. / Dose 0.4 mg/g

Efficacy

Remarks

Feeding inhibition = 59% approximately

Treatment to larvae of 75 to 85 mg body weight for 3 days. Data calculated from Reference 2. (2)

(1) Bringmann, G., Rubenacker, M., Jansen, J.R., Schetuzow, D., and Ake Assi, L. (1990) Tetrahedron Lett., 31, 639. (2) Bringmann, G., Gramatzki, S., Grimm, C., and Proksch, P. (1992) Phytochemistry 31, 3821.

© 2005 by CRC Press LLC

392

Opender Koul

1,5-DIPHENYL-1-PENTANONE

C17H18O (238.31)

Only spectral data given

O

(1)

(1)

SOURCE: Stellera chamaejasme L., Chinese Lang du (Thymelaeaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Aphis gossypii Glov. (Cotton aphid)

2. Schizaphis graminum (Rondani) (Wheat aphid)

Test Method Coated leaf assay

Coated leaf assay

Conc. / Dose

Efficacy

Remarks

2000 mg/litre

Feeding inhibition = 95.8%

1000 mg/litre

Feeding inhibition = 86.0%

Treatment to apterous adult aphids up to 12 h. (1)

2000 mg/litre

Feeding inhibition = 92.7%

1000 mg/litre

Feeding inhibition = 89.9%

Treatment to apterous adult aphids up to 12 h. (1)

(1) Ping, G, Taiping, H., Rong, G., Qui, C., and Shigui, L. (2001) Pest. Manag. Sci., 57, 307.

© 2005 by CRC Press LLC

Insect Antifeedants

1,5-DIPHENYL-2-PENTEN-1-ONE

393

C17H16O (236.31)

Only spectral data given

O

(1)

(1) SOURCE: Stellera chamaejasme L., Chinese Lang du (Thymelaeaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Aphis gossypii Glov. (Cotton aphid)

2. Schizaphis graminum (Rond.) (Wheat aphid)

Test Method Coated leaf assay

Coated leaf assay

Conc. / Dose

Efficacy

Remarks

2000 mg/litre

Feeding inhibition = 100.0%

1000 mg/litre

Feeding inhibition = 92.4%

Treatment to apterous adult aphids up to 12 h. (1)

2000 mg/litre

Feeding inhibition = 100.0%

1000 mg/litre

Feeding inhibition = 95.2%

Treatment to apterous adult aphids up to 12 h. (1)

(1) Ping, G, Taiping, H., Rong, G., Qui, C., and Shigui, L. (2001) Pest. Manag. Sci., 57, 307.

© 2005 by CRC Press LLC

394

Opender Koul

DIPLOPHYLLOLIDE–A

C15H20O2 (232.32)

M.p. : 60–62° [α]D27 : +18.6° (neat)

O O

CH2

(1)

(1, 2)

SOURCE: Eupatorium quadrangularae L., joe-pye-weed (Asteraceae); Diplophyllum albicans (L.) Dum., Liverwort (Bryophyta) (1, 2) ACTIVITY PROFILE Test Insect Atta cephalotes (L.) (Leaf cutter ant)

Test Method Rye flake forced choice test

Conc. / Dose 0.3 mg/ml or 6 µg/flake

Efficacy

Remarks

Feeding inhibition = 69.7%

Treatment to adult workers. (1) Data calculated from Reference 1.

(1) Hubert, T.D., Okunade, A.L., and Weimer, D.F. (1987) Phytochemistry, 26, 1751. (1) Benesova, V., Samek, Z., and Vasickova, S. (1975) Collect. Czech. Chem. Commun., 40, 1966.

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Insect Antifeedants

DITHYREANITRILE

395

C13H14ON2S2 (278.40)

M.p. : 135°

S

S

CN

N

O

(1)

(1)

SOURCE: Dithyrea wislizenii Engelm., desert lily (Cruciferae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

1. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Leaf disk choice test

2. Ostrinia nubilalis (Hubner) (European corn borer)

Leaf disk choice test

Conc. / Dose 1.0%

Efficacy

Remarks

Feeding ratio = 0.11

Treatment to larvae starved overnight for 3 h. Ratio below 0.2 considered as highly deterrent. (1)

Feeding deterrent

2. Treatment to larvae. No quantitative data recorded. (1)

(1) Powell, R.G., Mikolajczak, K.L., Zilkowski, B.W., Lu, H.S.M., Mantus, E.K., and Clardy, J. (1991) Experientia, 47, 304.

© 2005 by CRC Press LLC

396

Opender Koul

DJENKOLIC ACID

C7H14O4N2S2 (254.33)

M.p. : 300–350° (dec.) [α]D25 : –44.5° (HCl)

COOH

H2N

C

CH2

COOH

H2N

H

S

S

CH2

C

H

CH2

(1, 2)

(1, 2)

SOURCE: Acacia sp. (Fabaceae)

(3)

ACTIVITY PROFILE Test Insect Locusta migratoria migratoriodes (R & F) (Migratory locust)

Test Method Glass fiber disk test

Conc. / Dose

Efficacy

Remarks

1.0% of disk weight

Feeding inhibition = 61–90%

Treatment to male 5th instar nymphs. (3)

(1) Van Veen, A.G. and Hijman, A.J. (1935) Rec. Trav. Chim., 54, 493. (2) Armstrong, M.D. and du Vigneaud, V. (1947) J. Biol. Chem., 168, 373. (3) Evans, C.S. and Bell, E.A. (1979) Phytochemistry, 18, 1807.

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Insect Antifeedants

DYMALOL

397

C31H54O5 (506.76)

M.p. : 182–184° [α]D : +35° (CHCl3)

H O OH

H3COOC OH

(1)

(1)

SOURCE: Dysoxylum malabaricum Bedd. and ex CDC, white cedar (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding inhibition = 55.6%

Treatment to 3rd instar larvae for 24 h. (2)

5 µg/cm2

Feeding inhibition = 59.5%

10 µg/cm2

Feeding inhibition = 72.5%

50 µg/cm2

Feeding inhibition = 75.1%.

EC50 = 0.85 µg/cm2 Calculated from Reference 2.

(1) Govindachari, T.R., Suresh, G., and Krishna Kumari, G.N. (1994) Phytochemistry, 37, 1127. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari, G.N. (1995) J. Chem. Ecol., 21, 1586.

© 2005 by CRC Press LLC

398

Opender Koul

EICOSANOIC ACID (Arachidic acid)

C20H40O2 (312.54)

M.p. : 77° B.p. : 203–205°/1 mm

HOOC

(1, 2, 3)

(1, 2)

SOURCE: Synthetic Hibiscus syriacus L., rose-of-sharon (Malvaceae)

(3) (4)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Incisitermes minor (Hagen) (Western drywood termite)

Paper towel disk test

2. Anthonomus grandis Bohem. (Boll weevil)

Plate bioassay

Test Insect

Efficacy

Remarks

0.05 mg/cm2

Feeding inhibition = 40.0%

1. Treatment to 10 to 13 mg body weight larvae for 6 days. (3)

100 µg/ feeding site

Feeding = 80% of controls after 3 h and 87% after 6 h in males and 80% of controls after 6 h in females.

2. Treatment to adult weevils. (4)

(1) Adams, N.K. and Dyer, J.W.W. (1925) J. Chem. Soc., 72. (2) Bleyburg, W. and Ulrich, H. (1931) Ber., 64, 2512. (3) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. (4) Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) J. Chem. Ecol., 13, 1087.

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Insect Antifeedants

13-EICOSENOIC ACID

399

C20H38O2 (310.52)

Only spectral data given

HOOC

(1, 2)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk test

0.05 mg/cm2

Efficacy

Remarks

Feeding inhibition = 26.5%

Treatment to 10 to 13 mg body weight larvae for 6 days. (2) Data calculated from Reference 2.

(1) Richter, I., Mukherjee, K. D., and Weber, N. (1978) Z. Naturforsch., 33C, 629. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

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400

Opender Koul

α-ELEOSTEARIC ACID

C18H30O2 (278.44)

M.p. : 49–49.2°

HOOC

(1)

(1)

SOURCE: Aleurites fordii Hemsl., tung tree (Euphorbiaceae)

(1)

ACTIVITY PROFILE Test Insect Anthonomus grandis grandis Bohem. (Boll weevil)

Test Method Cotton bud dip method

Conc. / Dose 1.0%

Efficacy

Remarks

Feeding inhibition = 82.1%

Treatment to 1- or 2day-old boll weevils for 4 h. Data based on punctures made on buds in both treated and control situations. (1) Data calculated from Reference 1.

(1) Jacobson, M., Crystal, M.M., and Warthen, J.D. Jr. (1981) J. Agric. Food Chem., 29, 591.

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Insect Antifeedants

ELLAGIC ACID

401

C14H6O8 (302.19)

M.p. : >360°

O OH

O

HO

OH

O

OH

O

(1, 2)

(1, 2) SOURCE: Geranium viscosissium Fisch and Meyer, sticky geranium (Geraniaceae)

(3)

ACTIVITY PROFILE Test Insect 1. Schizaphis graminum (Rondani) (Wheat aphid)

Test Method Artificial diet feeding

Conc. / Dose 15 ppm

Efficacy Feeding inhibition = 50.0%

Remarks 1. Treatment to aphids at random. (3)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

1500 ppm

Not active up to this level of treatment

2. Treatment to aphids at random. (3)

(1) Perkin, A.G. and Nierenstein, M. (1905) J. Chem. Soc., 1415. (2) Nierenstein, M. (1931) Helv. Chim. Acta, 14, 912. (3) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.

© 2005 by CRC Press LLC

402

Opender Koul

EMBELIN

C17H26O4 (294.39)

Orange crystals M.p. : 142–143° 145–146°

O OH

HO O

(1, 2)

(2)

SOURCE: Rapanea melanphloes (L.) Mez., East African ethano-plant (Myrsinaceae)

(1)

ACTIVITY PROFILE Test Insect Schistocerca gregaria (Forsk.) (Desert locust)

Test Method Filter paper no-choice assay

Conc. / Dose 100 µg/ml

Efficacy

Remarks

Feeding inhibition = 88.4%

Treatment to mid 5th instar females prestarved for 24 h. Treatment duration = 24 h. (1)

(1) Midiwo, J.O., Mwangi, R.W., and Ghebremeskel, Y. (1995) Insect Sci. Applic., 16, 163. (2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 157.

© 2005 by CRC Press LLC

Insect Antifeedants

ENCECALIN

403

C14H16O3 (232.27)

B.p. : 135–137°/0.11 mm

O

O

H3CO

(1, 2)

(1)

SOURCE: Encelia farinosa Gray, brittle bush (Asteraceae) Also in many other species of the desert sunflowers of genus Encelia, Ageratina, etc.

(1)

ACTIVITY PROFILE Test Insect Epilachana varivestis Muls. (Mexican bean beetle)

Test Method

Conc. / Dose

Efficacy

Remarks

Leaf disk test

0.05 µmol/ leaf disk

Feeding inhibition = 50.0%

Treatment to 1- to 4-day-old insects for 20 to 24 h. Concentration = FI50 value (2)

(1) Sukh, Dev and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 193. (2) Srivastava, R.P. and Proksch, P. (1990) Naturwissenschaften, 77, 438.

© 2005 by CRC Press LLC

404

Opender Koul

ENCELIN

C15H16O3 (244.29)

M.p. : 195–196° [α]26 D : –16.5° (CHCl3)

O O O CH2

CH2

(1, 2)

(1)

SOURCE: Encelia asperifolia (S.F. Blake) Clark and Kyhos, brittle bush (Asteraceae) Encelia actoni Elmer., acton encelia (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Artificial diet feeding

1.0 µmol/g

Efficacy Feeding inhibition = significant

Remarks Treatment to 2nd instar larvae for 3 days. No quantitative data recorded. (2)

(1) Geissman, T.A. and Mukherjee, R. (1968) J. Org. Chem., 33, 656. (2) Srivastava, R.P., Proksch, P., and Wray, V. (1990) Phytochemistry, 29, 3445.

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Insect Antifeedants

ENHYDRIN

405

C23H28O10 (464.47) O

H3COOC

M.p. : 185–186° [α]D : –56.6° (CHCl3)

OOC OAc

CH2

O O O

(1, 2)

(1)

SOURCE: Polymnia uvedali L., bear’s foot (Asteraceae) Enhydra fluctuans Lour., weed (Asteraceae)

(2) (3)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method Cellulose millipore filter disk test

Conc. / Dose 1.0%

Efficacy Mean feeding inhibition rating = 7.1 mg

(1) Kartha, G., Go, K.T., and Joshi, B.S. (1972) J. Chem Soc. Chem. Commun., 1327. (2) Smith, C.M., Kester, K.M., and Fischer, N.H. (1983) Biol. Syst. Ecol., 11, 377. (3) Joshi, B.S. (1976) J. Sci. Indus. Res., 35, 239.

© 2005 by CRC Press LLC

Remarks Treatment to 4th instar larvae. Average deterrence rating based on (control-treated) disk consumption. (2)

406

Opender Koul

ENTANDROPHRAGMIN

C43H56O17 (844.91) O

M.p. : 256° [α]20 : –4°

COO O O

O

O O

OH H3COOC

OCO OH OCO

O

(1, 2)

(1)

SOURCE: Entandrophragma spp. (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Ostrinia nubilalis (Hubner) (European corn borer)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

50 µg/g

Feeding inhibition = 73.0%

Treatment to neonate larvae for 48 h. (2)

500 µg/g

Feeding inhibition = 75.0%

(1) Halsall, T.G., Wragg, K., Connolly, J.D., McLellan, M.A., Bredell, L.D., and Taylor, D.A.H. (1977) J. Chem. Res. Synop., 154. (2) Arnason, J.T., Philogene, B.J.R., Donskov., N., and Kubo, I. (1987) Entomol. Exp. Appl., 43, 221.

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Insect Antifeedants

ENT-3,13E-CLERODIEN-15-OIC ACID

407

C20H32O2 (304.47)

Only spectral data given

COOH

(1)

(1)

SOURCE: Detarium microcarpum Guill. & Perr., African atokolo (Caesalpiniaceae)

(1)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method Paper disk choice bioassay

Conc. / Dose 1.0% or 80 µg/cm2

Efficacy

Remarks

Feeding inhibition index value = < 5.0

Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index below 20 highly active. (2)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1101. (2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

408

Opender Koul

ENT-4 (18),13E-CLERODIEN-15-OIC ACID

C20H32O2 (304.47)

Oil [α]D : +10° (CHCl3)

COOH

CH2

(1)

(1)

SOURCE: Detarium microcarpum Guill. & Perr., African atokolo (Caesalpiniaceae)

(1)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method Paper disk choice bioassay

Conc. / Dose 1.0% or 80 µg/cm2

Efficacy

Remarks

Feeding inhibition index value = < 5.0

Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index below 20 highly effective. (1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1101.

© 2005 by CRC Press LLC

Insect Antifeedants

ENTILIN–D

409

C29H38O9 (530.61) O

M.p. : 107–110° (177–178°) [α]20 D : –38.6° (CHCl3)

OAc O HO O

O

O OH

(1, 2)

(1)

SOURCE: Entandrophragma utile (Dawe et Sprague) Sprague, utile (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 78.6

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 188.1 Larvae = 180.0

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 157.3

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Daniewski, W.M., Ancezewski, W., Gumulka, M., Danikiewicz, W., Jacobson, U., and Norin, T. (1995) Phytochemistry, 40, 903. (2) Daniewski, W.M., Gumulka, M., Ancezewski, W., Truszewska, D., Bloszyk, E., and Drozdz, B. (1996) Polish J. Chem., 70, 1265.

© 2005 by CRC Press LLC

410

Opender Koul

ENT-KAURADIENOIC ACID

C20H28O2 (300.44)

M.p. : 171–172°

CH2

COOH

(1)

(1)

SOURCE: Wedelia biflora (L.) DC., sami scandent shrub (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Anthonomus grandis grandis Bohem. (Boll weevil)

Test Method Agar plug bioassay

Conc. / Dose 5.0 mg/plug

Efficacy

Remarks

Feeding inhibition = 83.4%

Treatment to newly emerged boll weevils in the dark at 80°F for 4 h. Plug size for experiments In dark = 1.3 cm In light = 3.6 cm (1)

(1) Miles, D.H., Chittawong, V., Payne, A.M., Hedin, P.A., and Kokpol, U. (1990) J. Agric. Food Chem., 38, 1591.

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Insect Antifeedants

3-EPICARYOPTIN

411

C26H36O9 (492.56) O

M.p. : 171–172° [α]D : –70° (CHCl3)

H

H O H

AcO O

CH2 OAc OAc

(1)

(1)

SOURCE: Clerodendron calamitosum L., clerodendron (Verbenaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice bioassay

Conc. / Dose 200 ppm

Efficacy

Remarks

Feeding inhibition = 100% within 2 h

Treatment to 3rd instar larvae. Compound considered to be absolute antifeedant. (2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1974) Phytochemistry, 13, 308. (2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC

412

Opender Koul

3-EPIDIHYDROCARYOPTIN

C27H38O9 (506.59) CH2

M.p. : 161–162° [α]D : –42° (CHCl3)

O H

H O H

AcO O

CH2 OAc OAc

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice bioassay

Conc. / Dose 100 ppm

Efficacy

Remarks

Feeding inhibition = 100% within 2 h

Treatment to 3rd instar larvae. Larvae die within 24 h. Compound considered to be absolute antifeedant. (2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1974) Phytochemistry, 13, 308. (2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC

Insect Antifeedants

(+) EPIEUDESMIN

413

C22H26O6 (386.44)

M.p. : 131–132° [α]25 D : 130° (CHCl3)

O O O O O O

(1)

(1)

SOURCE: Parabenzoin praecox Nakai, Japanese parabenzoin (Lauraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

1.0%

Feeding inhibition = 90–100%

Treatment to 3rd instar larvae for 2 h. (1)

0.05%

Feeding inhibition = 90–100%

0.01%

Feeding inhibition = 50–70%

(1) Matsui, K., Wada, K., and Munakata, K. (1976) Agric. Biol. Chem., 40, 1045.

© 2005 by CRC Press LLC

414

Opender Koul

EPILIMONOL

C26H32O8 (472.51)

M.p. : 262–266° [α]D : +9° (Acetone)

O O

O

O

O O

O OH

(1, 2)

(1)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect 1. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method Leaf disk bioassay

Glass-fiber disk test

Conc. / Dose

Efficacy

Remarks

100 µg/cm2

Feeding inhibition = 98.5%

31.7 µg/cm2

Feeding inhibition = 84.9%

1. Treatment to 4th instar larvae for 6–8 h. (2)

10.0 µg/cm2

Feeding inhibition = 53.9%

3.17 µg/cm2

Feeding inhibition = 19.3%

100 ppm

Feeding inhibition = 56.0%

FI50 = 8.84 µg/cm2 Calculated from Reference 2.

2. Treament to 24- to 36-h-old last stadium larvae for 8 h. The larvae were prestarved for 2 h. (3)

(1) Barton, D.H.R., Pradhan, S.K., Sternhell, S., and Templeton, J.F. (1961) J. Chem. Soc., 255. (2) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189. (3) Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) J. Agric. Food Chem., 50, 6766.

© 2005 by CRC Press LLC

Insect Antifeedants

EPILIMONOL ACETATE

415

C28H34O9 (514.54)

M.p. : 298–301°

O O

O

O

O O

O OAc

(1, 2)

(1)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk bioassay

Conc. / Dose

Efficacy

100 µg/cm2

Feeding inhibition = 97.5%

31.7 µg/cm2

Feeding inhibition = 86.1%

10.0 µg/cm2

Feeding inhibition = 53.8%

3.17 µg/cm2

Feeding inhibition = 9.5%

Remarks Treatment to 4th instar larvae for 6–8 h. (2) FI50 = 10.49 µg/cm2 Calculated from Reference 2.

(1) Barton, D.H.R., Pradhan, S.K., Sternhell, S., and Templeton, J.F. (1961) J. Chem. Soc., 255. (2) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.

© 2005 by CRC Press LLC

416

Opender Koul

12-EPI-TEUCVIN

C19H20O5 (328.36)

M.p. : 197–199°

O

[α]D : +222.6° (CHCl3)

O O

O O

(1)

(1, 2) SOURCE: Teucrium flavum glaucum L., geber germander (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Helicoverpa armigera (Hubner) (Gram pod borer)

Test Method

Conc. / Dose

Glass fiber disk choice bioassay

100 ppm

Glass fiber disk choice bioassay

100 ppm

10 ppm

10 ppm

Efficacy

Remarks

Feeding inhibition = 49.9% Feeding inhibition = 45.4%

Treatment to final stadium larvae starved for 4 h. Treatment duration = maximum of 18 h so that never more than 50% of any disk was consumed. (2)

Feeding inhibition = 29.6% Feeding inhibition = 29.2%

(1) Fayos, J., Fernandez-Gadea, F., Pascual, C., Perales, A., Piozzi, F., Rico, M., Rodriguez, B., and Savona, G. (1984) J. Org. Chem., 49, 1789. (2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry, 28, 1069.

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Insect Antifeedants

14-EPOXYAZADIRADIONE

417

C28H34O6 (466.57)

M.p. : 202–204° [α]D : +45° (CHCl3)

O

O

O O

OAc

(1, 2, 3)

(1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Epilachna varivestis Muls. (Mexican bean beetle)

Bean leaf choice bioassay

0.14%

Feeding inhibition = 50.0%

Treatment to 4th stadium larvae for up to 24 h. Concentration = EC50 value. (2)

2. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk dual choice bioassay

1 µg/cm2

Feeding 51.5% Feeding 61.4% Feeding 64.8% Feeding 73.0%

2. Treatment to 3rd instar larvae for 24 h. (3)

5 µg/cm2 10 µg/cm2 50 µg/cm2

inhibition = inhibition = inhibition = inhibition =

FI50 = 0.66 µg/cm2 Calculated from Reference 3.

(1) Lavie, D., Levy, E.C., and Jain, M.K. (1971) Tetrahedron, 27, 3927. (2) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–189. (3) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari, G.N. (1995) J. Chem. Ecol., 21, 1586.

© 2005 by CRC Press LLC

418

Opender Koul

19β,28-EPOXY-2 (β-D-GLUCO-PYRANO SYLOXY)-18-α-OLEAN-1-EN-3-ONE

C36H57O8 (617.84)

M.p. : 157–158°

O

GluO

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Heliothis zea (Boddie.) (Corn earworm)

Test Method Leaf disk choice bioassay

Conc. / Dose

Efficacy

Remarks

3.17 µg/cm2

Feeding inhibition = 40.0%

Treatment to 4th stadium larvae for up to 19–22 h. (1)

10 µg/cm2

Feeding inhibition = 83.0%

FI50 = 3.48 µg/cm2 Calculated from Reference 1.

100 µg/cm2

Feeding inhibition = 92.0%

(1) Lugemwa, F.N., Huang, F., Bentley, M.D., Mendel, M.J., and Alford, A.R. (1990) J. Agric. Food Chem., 38, 493.

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Insect Antifeedants

5β,6β-EPOXY-1β,14α,17β,20-TETRA HYDROXY WITH-24-ENOLIDE

419

C28H40O7 (488.61)

No physical data given

OH O

O

OH OH

OH O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Epilachna varivestis Muls. (Mexican bean beetle)

Test Method

Conc. / Dose

Styropor test

Leaf residue test

Efficacy Feeding inhibition =

0.1%

98.5%

0.01%

91.0%

0.005%

86.3%

0.0025%

54.6%

0.0001%

40.7%

0.1%

Weight gain = − 1.22 mg versus control = 12.1 mg Weight gain = − 1.76 mg versus control = 11.5 mg

0.05%

Remarks 1. Treatment to larvae of 170–190 mg body weight. (1) FI50 = 0.0019% Data calculated from Reference 1.

2. Treatment to 4th instar larvae for 48 h. Data based on growth rate. (2)

(1) Ascher, K.R.S., Nemny, N.E., Eliyahu, M., Kirson, I., Abraham, A., and Glotter, E. (1980) Experientia, 36, 998. (2) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197.

© 2005 by CRC Press LLC

420

Opender Koul

α-ERGOCRYPTINE

C32H41O5N5 (575.71) OH

M.p. : 211–212° (dec.) [α]20 D : –198° (CHCl3)

O

O

N N

N O

O

N

N

(1)

(1, 2) SOURCE: Commercial sample Also obtained from Lolium perenne L. (rye grass) infected with fungus Neotyphodium Lolii.

(2)

ACTIVITY PROFILE Test Insect Heteronychus arator (Fab.) (Black beetle)

LD50 (rats): 0.95 mg/kg (ivn.)

Test Method Artificial diet choice test

Conc. / Dose

Efficacy

Remarks

5 µg/g

Feeding inhibition = 47.1%

Treatment to adult beetles for 96 h. (2)

10 µg/g

Feeding inhibition = 60.0%

Data calculated from Reference 2.

(3)

(1) Schlientz, W., Brunner, R., Ruegger, A., Berde, B., Stuermer, E., and Hofmann, A. (1968) Pharm. Acta Helv., 43, 497. (2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

ERGONOVINE

421

C19H23O2N3 (325.41) HO

M.p. : 162–163° (dec.) (212°, dec., dimorph.)

O NH

N

N

(1, 2)

(1)

SOURCE: Commercial sample Also obtained from Lolium perenne L. (rye grass) infected with fungus Neotyphodium Lolii.

(2)

ACTIVITY PROFILE Test Insect Heteronychus arator (Fab.) (Black beetle)

Test Method Artificial diet choice test

Conc. / Dose 10 µg/g

Efficacy

Remarks

Feeding inhibition = 40.0%

Treatment to adult beetles for 96 h. (2) Data calculated from Reference 2.

LD50 (mice): 144 mg/kg (ivn.)

(3)

(1) Jacobs, W.A. and Craig, L.C. (1935) Science, 82,16. (2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

422

Opender Koul

α-ERGOSINE

C30H37O5N5 (547.65) OH

[α]20 D : –161° (CHCl3)

O

O

M.p. : 228° (dec.)

N N

N O

O

N

N

(1, 2,3)

(1, 2)

SOURCE: Commercial sample Also obtained from Lolium perenne L. (rye grass) infected with fungus Neotyphodium Lolii.

(3)

ACTIVITY PROFILE Test Insect Heteronychus arator (Fab.) (black beetle)

Test Method Artificial diet choice test

Conc. / Dose

Efficacy

Remarks

5 µg/g

Feeding inhibition = 69.2%

Treatment to adult beetles for 96 h. (3)

10 µg/g

Feeding inhibition = 75.8%

20 µg/g

Feeding inhibition = 81.3%

(1) Smith, S. and Timmis, G.M. (1937) J. Chem. Soc., 396. (2) Stauffacher, D., Tscherter, H., and Hofmann, A. (1965) Helv. Chim. Acta, 48, 1379. (3) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.

© 2005 by CRC Press LLC

Data calculated from Reference 3.

Insect Antifeedants

ERGOTAMINE

423

C33H35O5N5 (581.67) OH

[α]20 D : –160° (CHCl3)

O

O

M.p. : 213–214° (dec.)

N N

N

O

O

N

N

(1)

(1, 2) SOURCE: Commercial sample Also obtained from Lolium perenne L. (rye grass) infected with fungus Neotyphodium Lolii.

(2)

ACTIVITY PROFILE Test Insect Heteronychus arator (Fab.) (Black beetle)

Test Method Artificial diet choice test

Conc. / Dose

Efficacy

Remarks

5 µg/g

Feeding inhibition = 53.8%

Treatment to adult beetles for 96 h. (2)

10 µg/g

Feeding inhibition = 60.0%

20 µg/g

Feeding inhibition = 85.7%

(1) Stoll, A., Hofmann, A., and Petrzilka, Th. (1951) Helv. Chim. Acta, 34, 1544. (2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.

© 2005 by CRC Press LLC

Data calculated from Reference 2.

424

Opender Koul

ERGOVALINE

C29H35O5N5 (533.63) OH

[α]20 D : –172° (CHCl3)

O

O

M.p. : 207–208° (dec.)

N N

N O

O

N

N

(1)

(1, 2) SOURCE: Commercial sample Also obtained from Lolium perenne L. (rye grass) infected with fungus Neotyphodium Lolii.

(2)

ACTIVITY PROFILE Test Insect Heteronychus arator (Fab.) (Black beetle)

Test Method Artificial diet choice test

Conc. / Dose

Efficacy

Remarks

5 µg/g

Feeding inhibition = 42.9%

Treatment to adult beetles for 96 h. (2)

10 µg/g

Feeding inhibition = 73.9%

Data calculated from Reference 2.

(1) Brunner, R., Stuetz, P.L., Tscherter, H., and Stadler, P.A. (1979) Can. J. Chem., 57, 1638. (2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.

© 2005 by CRC Press LLC

Insect Antifeedants

ERIOCEPHALIN

425

C24H30O9 (462.50)

M.p. : 197–200°

O

[α]20 D : +76.1° (CHCl3)

O OAc

OH O O OAc

(1, 2)

(1)

SOURCE: Teucrium eriocephalum, germander (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Efficacy

Glass fiber disk choice bioassay

100 ppm

2. Helicoverpa armigera (Hubner) (Gram pod borer)

Glass fiber disk choice bioassay

100 ppm

3. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk choice test

1000 ppm

Feeding inhibition = 23.8%

Leaf disk nochoice test

1000 ppm

Feeding inhibition = 60.1%

10 ppm

10 ppm

Feeding 48.9% Feeding 40.9% Feeding 23.9% Feeding 24.0%

inhibition = inhibition = inhibition = inhibition =

Remarks 1, 2. Treatment to final stadium larvae starved for 4 h. Treatment duration = maximum of 18 h so that never more than 50% of any disk was consumed. (2) 3. Treatment to 4th instar larvae for 4 h in no-choice assay and for up to 24 h or until 50% of disks were consumed in choice situation. (3)

(1) Piozzi, F. (1981) Heterocycles, 15, 1489. (2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry, 28, 1069. (3) Ortego, F., Rodriguez, B., and Castanera, P. (1995) J. Chem. Ecol., 21, 1375.

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426

Opender Koul

ERIODICTYOL

C15H12O6 (288.25) OH

OH

HO

M.p. : 257° (dec.)

O

OH

O

(1, 2)

(1)

SOURCE: Eriodictyon californicum (Hook and Arn.) Torr., bear’s weed (Hydrophyllaceae) Semisynthetic as well

(1) (2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

0.02%

Feeding inhibition = 50.0%

1. Treatment to 50 to 75 aphids at random. (2)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

0.02%

Feeding inhibition = 50.0%

2. Treatment to 50 to 75 aphids at random. (2)

(1) Geissman, T.A. (1940) J. Am. Chem. Soc., 62, 3258. (2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

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Insect Antifeedants

ERIVANIN

427

C15H22O4 (266.34)

M.p. : 203–205° [α]20 D : +112° (EtOH)

OH

HO CH2

O

(1)

(1)

SOURCE: Chrysanthemum balsamita L., costmary (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 98.2

Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 132.1 (adults) 81.0 (larvae)

Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 79.8

Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Evstratova, R.I., Sheichenko, V.I., Bankovskii, A.I., and Rybalko, K.S. (1969) Khim. Prir. Soedin., 5, 239. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Dorzdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk. Inst. Ochr. Roslin., 25, 91.

© 2005 by CRC Press LLC

428

Opender Koul

ERMANIN

C17H14O6 (314.29)

OH

M.p. : 235°

O OCH3

HO

O

OCH3

(1, 2)

(1, 2)

SOURCE: Passiflora foetida L., passionflower weed (Passifloraceae)

(1)

ACTIVITY PROFILE Test Insect Dione juno (Stoll) (Silverspot butterfly)

Test Method Plant lobule choice test

Conc. / Dose 40 ppm

Efficacy Feeding deterrence = Significant

Remarks Treatment to 3rd instar larvae prestarved for 12 h. (1) No quantitative data recorded.

(1) Echeverri, F., Cardona, G., Torres, F., Pelaez, C., Quinones, W., and Renteria, E. (1991) Phytochemistry, 30, 153. (2) Wollenweber, E. and Mann, K. (1984) Z. Naturforsch., 39, 303.

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Insect Antifeedants

ERYTHRO-9,10-DIHYDROXY-1OCTADECANOL ACETATE

429

C20H40O4 (344.54)

M.p. : 54°

AcO

OH

OH

(1)

(1)

SOURCE: Aleurites fordii Hensl., tung tree (Euphorbiaceae)

(1)

ACTIVITY PROFILE Test Insect Anthonomus grandis grandis Bohem (Boll weevil)

Test Method Cotton bud dip test

Conc. / Dose 1.0%

Efficacy

Remarks

Feeding deterrence = 66.7%

Treatment to 1- or 2day-old boll weevils for 4 h. Data based on punctures observed in test material versus controls. (1)

(1) Jacobson, M., Crystal, M.M., and Warthen, J.D. Jr. (1981) J. Agric. Food Chem., 29, 591.

© 2005 by CRC Press LLC

430

Opender Koul

15-ETHOXY-14-HYDRO AJUGAPTIN

C31H48O11 (596.71)

OC2H5

[α]20 D : –3.53° (CHCl3)

O H

H O H

H HO

COO O

CH2 OAc OAc

(1)

(1)

SOURCE: Ajuga chamaepitys (L.) Schreb., ground pine (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

10 µg/cm2

Feeding ratio = 0.11 ± 0.03

1 µg/cm2

Feeding ratio = 0.39 ± 0.07

(1) Camps, F., Coll, J., and Dargallo, O. (1984) Phytochemistry, 23, 2577. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC

Remarks Treatment to newly ecdysed 5th instar larvae. Data based on the ratio when 50% of control disk area was consumed and represents FR50 value. FR50 value < 0.5 is excellent antifeedant activity. (2)

Insect Antifeedants

24-ETHYLCOPROSTANONE

431

C29H50O (414.72)

M.p. : 113–114°

O

(1)

(1)

SOURCE: Wedelia biflora (L.) DC., sami scandent shrub (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Anthonomus grandis grandis Bohem. (Boll weevil)

Test Method Agar plug bioassay

Conc. / Dose 2.0 mg/plug

Efficacy

Remarks

Feeding inhibition = 90.0%

Treatment to newly emerged boll weevils in the dark at 80°F for 4 h. Plug size for experiments In dark = 1.3 cm In light = 3.6 cm (1)

(1) Miles, D.H., Chittawong, V., Payne, A.M., Hedin, P.A., and Kokpol, U. (1990) J. Agric. Food Chem., 38, 1591.

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432

Opender Koul

EUDESMENE

C15H20O2 (232.32)

Oily solid

CH2

HO

O

(1)

(1)

SOURCE: Helianthus annuus L., sunflower (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Diabrotica virgifera virgifera LeConte (Western corn rootworm)

Test Method

Conc. / Dose

Leaf disk bioassay

4.0 µg/1.5 cm2

Efficacy

Remarks

Feeding inhibition = 47% reduction in consumption after 5 h and 25% reduction in consumption after 24 h.

Treatment to adults. (1)

(1) Alfatafta, A.A. and Mullin, C.A. (1992) Phytochemistry, 31, 4109.

© 2005 by CRC Press LLC

Insect Antifeedants

(+) EUDESMIN

433

C22H26O6 (386.44)

H3CO

M.p. : 107–108° [α]20 D : + 60.5° (Me2CO)

O H3CO H

H

O

OCH3 OCH3

(2)

(1) SOURCE: Parabenzoin praecox Nakai, Japanese parabenzoin (Lauraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

1.0%

Feeding inhibition = 90–100%

0.5%

Feeding inhibition = 70–90%

0.1%

No activity

Remarks Treatment to 3rd instar larvae. (1)

(1) Matsui, K., Wada, K., and Munakata, K. (1976) Agric. Biol. Chem., 40, 1045. (2) (1982) Dictionary of Organic Compounds, Vol. 3, Chapman & Hall, New York, p. 2581.

© 2005 by CRC Press LLC

434

Opender Koul

EUGENOL

C10H12O2 (164.20)

M.p. : –9° B.p. : 254°

CH2

n19 D

: 1.5439

d25 4

: 1.0620

CH3O OH

(1)

(1, 2) SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Pieris brassicae (L.) (Large white butterfly)

LD50 (rats): 2680 mg/kg (oral)

Test Method Leaf disk no-choice test

Conc. / Dose

Efficacy

Remarks

6.6 × 10–2 M

Feeding ratio = 9.95

Treatment to 2nd day 5th instar unstarved larvae. Ratio based on control/treated insects (2)

Considered as strong deterrence

(3)

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 152. (2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187. (3) Hagan, E.C., Jenner, P.M., Jones, W.I., Fitzhugh, O.G., Long, E.L., Brouwer, J.G., and Webb, W.K. (1965) Toxicol. Appl. Pharmacol., 7, 18.

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Insect Antifeedants

EUPATOLIDE

435

C15H20O3 (248.32)

M.p. : 185–188° [α]22 D : +20° (Acetone)

OH

CH2

O O

(1)

(2)

SOURCE: Synthetic (also isolated from Eupatorium formosanum Hayata, bugleweed, E. cannabinum L., common water hemp; Asteraceae)

(1, 3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 54

Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 97.0 (adults) 36.0 (larvae)

Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 98.0

Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Harmatha, J., and Samek, Z. (1982) Collect. Czech. Chem. Commun., 47, 2779. (2) Sukh, Dev and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 84. (3) Harmatha, J. and Nawrot, J. (1984) Biochem. Syst. Ecol., 12, 95.

© 2005 by CRC Press LLC

436

Opender Koul

METHOXY EUPATOLIDE

C16H23O3 (263.36)

No physical data given

OH

OCH3 O

(1)

(2)

SOURCE: Synthetic

(1, 3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 109

Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 124.0 (adults) 89.0 (larvae)

Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 69.0

Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Harmatha, J. and Samek, Z. (1982) Collect. Czech. Chem. Commun., 47, 2779. (2) Harmatha, J. and Nawrot, J. (1984) Biochem. Syst. Ecol., 12, 95.

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Insect Antifeedants

DIETHYL NITRO EUPATOLIDE

437

C20H30O2N (316.47)

Only spectral data given

OH

N O

(1, 2)

(1, 2)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 68

Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 119.0 (adults) 109.0 (larvae)

Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 156.0

Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Harmatha, J. and Samek, Z. (1982) Collect. Czech. Chem. Commun., 47, 2779. (2) Harmatha, J. and Nawrot, J. (1984) Biochem. Syst. Ecol., 12, 95.

© 2005 by CRC Press LLC

438

Opender Koul

EUPATORIOPICRIN

C20H26O7 (378.42)

M.p. : 157–161° [α]20 D : +95° (CHCl3)

O O CH2 OH

HO

O OH O

(1, 2)

(1, 2)

SOURCE: Eupatorium cannabinum L., common water hemp (Asteraceae)

(3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 151–200 (adults) 101–150 (larvae)

Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 151–200

Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Dolejs, L. and Herout, V. (1962) Collect. Czech. Chem. Commun., 27, 2654. (2) Kupchan, S.M., Kelsey, J.E., and Sim, G.A. (1967) Tetrahedron Lett., 2863. (3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC

Insect Antifeedants

EVOXINE

439

C18H21O6N (347.37) OCH3

N

O

M.p. : 151–152° [α]22 D : +14.6° (EtOH)

O

OCH3

HO

OH

(1)

(1)

SOURCE: Oryxa japonica Thumb., Japanese kokusagi (Rutaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

500 ppm

Efficacy Feeding inhibition = 50.0%

Remarks Treatment to 3rd instar larvae. (1)

(1) Yajima, T., Kato, N., and Munakata, K. (1977) Agric. Biol. Chem., 41, 1263.

© 2005 by CRC Press LLC

440

Opender Koul

FENTIN ACETATE

C20H18O2Sn (409.04)

M.p. : 121-122°

CH3OCO.Sn

(1, 2)

(1)

SOURCE: Commercial formulation

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Musca domestica vicina L. (Housefly)

Artificial diet feeding

33 ppm

Due to starvation only 15 pupae were formed against 438 in controls.

1. Treatment to larvae at random in breeding media. (2)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Leaf disk choice test

0.058%

Feeding inhibition = 95.0%

2. Treatment to 170–190 mg body weight larvae. (3)

3. Gnorimoschema operculella (Zell.) (Potato tuber moth)

Leaf dip test

.05%

Feeding inhibition = 38.5%

3. Treatment to 2nd instar larvae. Data calculated from Reference 3. (3)

4. Scolytus mediterraneus Eggers (Bark beetle)

Twig dip test

0.2% AI

Twig penetration = 9%

4. Treatment to 0 to 1-day-old females. (4)

0.1% AI

Twig penetration = 26%

0.01% AI

Twig penetration = 68%

0.1 g/l AI

Only 7.9 pupae formed due to starvation

5. Boarmia selenaria (Denis & Schiff.) (Giant looper)

© 2005 by CRC Press LLC

Leaf dip test

5. Treatment to larvae at random. (5)

Insect Antifeedants

441

6. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf dip test

0.058%

Feeding inhibition = 95.0%

6. Treatment to 4th instar larvae. Data calculated on the basis of leaf protection. (6)

7. Chilo agamemnon Blesz. (Striped maize borer)

Leaf disk test

0.05%

Feeding inhibition = 74.7%

7. Treatment to larvae for 72 h. (7) Data calculated from Reference 7.

LD50 (rats): 140–298 mg/kg (oral) (1) Ingham, R.K., Rosenberg, S.D., and Gilman, H. (1960) Chem. Rev., 60, 459. (2) Ascher, K.R.S. and Moscowitz, J. (1968) Int. Pest Contr., 10, 10. (3) Ascher, K.R.S., Avdat, N., and Kamhi, J. (1970) Int. Pest Contr., 12, 11. (4) Ascher, K.R.S., Gurevitz, E., Renneh, S., and Nemny, N.E. (1975) Z. Pflkrankh. PflSchutz., 82, 378. (5) Ascher, K.R.S., Nemny, N.E., Wysoki, M., and Gur-Telzak, L. (1978) Pestic. Sci., 9, 566. (6) Ascher, K.R.S. and Nissim, S. (1965) Int. Pest Contr., 7, 21. (7) Meisner, J. and Ascher, K.R.S. (1965) Z. Pflkrankh. PflPath. Pflschutz., 72, 458. (8) Farms Chem. Handbook (1982) Meister Publishing Co., C300.

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442

Opender Koul

FENTIN CHLORIDE

C18H15SnCl (385.50)

M.p. : 105.5–107° B.p. : 249°/13.5 mm

Cl

Sn

(1, 2)

(1)

SOURCE: Commercial formulation

(2, 3)

ACTIVITY PROFILE Test Insect

Test Method

1. Boarmia selenaria (Denis & Schiff.) (Giant looper)

Leaf dip test

2. Tribolium confusum Duv. (Confused flour beetle)

Wheat flour mixture feeding

Conc. / Dose 0.1 g /l

Efficacy

Remarks

No larva reached to pupal stage due to starvation

1. Treatment to larvae at random

25 µmol/kg

Larval weight was only 24% of controls due to antifeedant efect.

2. Treatment to 0- to 3–h-old larvae. (3)

50 µmol/kg

< 5% weight than controls

(2)

LD50 (mice): 8 mg/kg (oral) (1) Ingram, R.K., Rosenberg, S.D., and Gilman, H. (1960) Chem. Rev., 60, 459. (2) Ascher, K.R.S., Nemny, N.E., Wysoki, M., and Gur-Telzak, L. (1978) Pestic. Sci., 9, 566. (3) Ishaaya, I., Ascher, K.R.S., and Yablonski, S. (1982) Phytoparasitica, 10, 205. (4) Farms Chem. Handbook (1982) Meister Publishing Co., C288.

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(4)

Insect Antifeedants

FENTIN HYDROXIDE

443

C18H16Osn (367.04)

HO

M.p. : 119–120°

Sn

(1, 2)

(1)

SOURCE: Commercial formulation

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Musca domestica vicina L. (Housefly)

Artificial diet feeding

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Insect

Efficacy

Remarks

33 ppm

Due to starvation only 48.5 pupae were formed against 183.2 in controls.

1. Treatment to larvae at random in breeding media. (2)

Leaf disk choice test

0.065%

Feeding inhibition = 95.0%

2. Treatment to 170190 mg body weight larvae. (3)

3. Gnorimoschema operculella (Zell.) (Potato tuber moth)

Leaf dip test

0.05%

Feeding inhibition = 38.5%

3. Treatment to 2nd instar larvae. Data calculated from Reference 3. (3)

4. Scolytus mediterraneus Eggers (Bark beetle)

Twig dip test

0.2% AI

Twig penetration = 8%

0.2% AI

Twig penetration = 17%

4. Treatment to 0- to 1-day-old females. (4)

0.02% AI

Twig penetration = 44%

0.1 g/l AI

No pupae formed due to starvation

5. Boarmia selenaria (Denis & Schiff.) (Giant looper)

Leaf dip test

6. Spodoptera litura Fab. (Tobacco armyworm)

Leaf dip test

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5. Treatment to larvae at random. (5)

0.065%

Feeding inhibition = 95.0%

6. Treatment to 4th instar larvae. Data calculated on the basis of leaf protection. (6)

444 7. Chilo agamemnon Blesz. (Striped maize borer)

Opender Koul Leaf disk test

0.05%

Feeding inhibition = 76.7%

7. Treatment to larvae for 72 h. (7) Data calculated from Reference 7

8. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk test

0.02%

Feeding inhibition = 89.9%

8. Treatment to F1 generation adults. (8)

LD50 (rats): 40–298 mg/kg (oral) (1) Ingham, R.K., Rosenberg, S.D., and Gilman, H. (1960) Chem. Rev., 60, 459. (2) Ascher, K.R.S. and Moscowitz, J. (1968) Int. Pest Contr., 10, 10. (3) Ascher, K.R.S., Avdat, N., and Kamhi, J. (1970) Int. Pest Contr., 12, 11. (4) Ascher, K.R.S., Gurevitz, E., Renneh, S., and Nemny, N.E. (1975) Z. Pflkrankh. PflSchutz., 82, 378. (5) Ascher, K.R.S., Nemny, N.E., Wysoki, M., and Gur-Telzak, L. (1978) Pestic. Sci., 9, 566. (6) Ascher, K.R.S. and Nissim, S. (1965) Int. Pest Contr., 7, 21. (7) Meisner, J. and Ascher, K.R.S. (1965) Z. Pflkrankh. PflPath. Pflschutz., 72, 458. (8) Hare, J.D., Logan, P.A., and Wright, R.J. (1983) Environ. Entomol., 12, 1470. (9) Farms Chem. Handbook (1982) Meister Publishing Co., C300.

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(9)

Insect Antifeedants

FERRUGININ–A

445

C30H36O4 (460.61)

OH

OH

M.p. : 168–170°

O

OH

(1, 2)

(1)

SOURCE: Vismia baccifera (L.) Tr. and Planch. var. ferruginea, achiote tigre (Clusiaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera exempta (Walker) (Nut grass armyworm)

Glass fiber disk test

10–3 M

Feeding inhibition = 54.29%

1. Treatment to last instar larvae. (2)

2. Heliothis virescens (Fab.) (Tobacco bud worm)

Glass fiber disk test

10–3 M

Feeding inhibition = 72.47%

2. Treatment to last instar larvae. (2)

(1) Delle Monache, F., Mac-Quhae, M.M., Ferrari, F., and Bettolo, G.B.M. (1985) Tetrahedron, 35, 2143. (2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem. Ecol., 11, 1593.

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446

Opender Koul

FERRUGININ–B

C30H36O4 (460.61) M.p. : 110–114°

OH

OH

O

OH

(1, 2)

(1)

SOURCE: Vismia baccifera (L.) Tr. and Planch. var. ferruginea, achiote tigre (Clusiaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Heliothis virescens (Fab.) (Tobacco bud worm)

Glass fiber disk test

10–3 M

Feeding inhibition = 57.76%

1. Treatment to last instar larvae. (2)

2. Locusta migratoria (L.) (Migratory locust)

Glass fiber disk test

10–3 M

Feeding inhibition = 65.5%

2. Treatment to last instar larvae. (2)

(1) Delle Monache, F., Mac-Quhae, M.M., Ferrari, F., and Bettolo, G.B.M. (1985) Tetrahedron, 35, 2143. (2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem. Ecol., 11, 1593.

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Insect Antifeedants

FLAVONE 5-HYDROXY-3,6,7,8,4′-PENTAMETHOXY

C20H20O8 (388.35)

M.p. : 122–123°

OCH3

OCH3 H3CO

447

O

H3CO

OCH3 OH

O

(1)

(1)

SOURCE: Gnaphalium affine D. Don, cud weed (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

1.1 × 10–7 mol/cm2

Feeding inhibition = 50%

1. Treatment to 3rd instar larvae in the dark for 2 to 5 h. Concentration = EC50 value (1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC

448

Opender Koul

FLAVONE 5-HYDROXY-3,6,7,8-TETRAMETHOXY

C19H18O7 (358.33)

M.p. : 98–100°

OCH3 H3CO

O

H3CO

OCH3 OH

O

(1)

(1)

SOURCE: Gnaphalium affine D. Don, cud weed (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

2.0 × 10–8 mol/cm2

Feeding inhibition = 50%

1. Treatment to 3rd instar larvae in the dark for 2 to 5 h. Concentration = EC50 value (1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC

Insect Antifeedants

FLAVONE 5,6-DIHYDROXY-3,7 DIMETHOXY

H3CO

449

C17H14O6 (314.28)

M.p. : 178°

O

HO

OCH3 OH

O

(1)

(1)

SOURCE: Gnaphalium affine D. Don, cud weed (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

2.5 × 10–8 mol/cm2

Feeding inhibition = 50%

1. Treatment to 3rd instar larvae in the dark for 2 to 5 h. Concentration = EC50 value (1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC

450

Opender Koul

FORMONONETIN

HO

C16H12O4 (268.26)

M.p. : 265–266° (257–258°)

O

O

OCH3

(1)

(1)

SOURCE: Trifolium pratense L., red clover (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Costelytra zealandica (White) (Scarab beetle)

Artificial diet feeding

2. Heteronychus arator (Fab.) (Black beetle)

Artificial diet feeding

Test Insect

Efficacy

Remarks

200 µg/ml

Feeding inhibition = 17.0%

1. Treatment to 3rd instar larvae after 24-h pre-starvation. (2)

200 µg/ml

Feeding inhibition = 15.0%

2. Treatment to 3rd instar larvae after 24-h pre-starvation. (2)

(1) Bradbury, R.B. and White, D.E. (1951) J. Chem. Soc., 3447. (2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

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Insect Antifeedants

8′-FORMYLOXYROTENONE

451

C25H22O8 (450.42)

OCH3 H3CO

No physical data given

O

O O

O CCH2OC

OH

H CH2

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 142.5

Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 140.6 (adults) 122.1 (larvae)

Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence Coefficient = 152.3

Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (1)

(1) Nawrot, J., Harmatha, J., Kostova, I., and Ognyanov, I. (1989) Biochem. Syst. Ecol., 17, 55.

© 2005 by CRC Press LLC

452

Opender Koul

3′-FORMYL-2′,4′,6′-TRIHYDROXY5′-METHYLDIHYDROCHALCONE

C17H16O5 (300.31)

M.p. : 157–158° [α]25 D : 0° (CHCl3)

CHO HO

OH

OH

O

(1)

(1) SOURCE: Psidium acutangulum DC, para guava (Myrtaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco bud worm)

Test Method Leaf disk choice test

Conc. / Dose 24.8 µg/cm2

Efficacy

Remarks

Feeding inhibition = 90.0%

Treatment to larvae for 2 days.

Feeding inhibition = 60.0-90.0%

Treatment to larvae for 4 days (1)

(1) Miles, D.H., Medeiros, J.M.R.D., Chittawong, V., Swithenbank, C., Lidert, Z., Weeks, J.A., Atwood, J.L. and Hedin, P.A. (1990) J. Nat. Prod., 53, 1548.

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Insect Antifeedants

FRAXINELLONE

453

C14H16O3 (232.28)

M.p. : 116°C [α]22 D : –44° (EtOH)

O

O

O

(1, 2)

(1)

SOURCE: Melia azedarach L., darekh (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy Feeding inhibition = 100%

Remarks Treatment to 3rd instar larvae. (2)

(1) Dreyer, D.L. (1983) Chemistry and Chemical Taxonomy of the Rutales, in P.G. Waterman and M.F. Grundon (eds.), Academic Press, London, p. 215. (2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., and Tadera, K. (1998) Phytochemistry, 49, 1773.

© 2005 by CRC Press LLC

454

Opender Koul

FRIEDELIN

C30H50O (426.73)

M.p. : 267–269° (263–263.5°) [α]14 D : –27.8° (CHCl3)

O

(1)

(1) SOURCE: Acokanthera spectabilis Hook, Bushman’s poison (Apocynaceae) Virola calophylla (Spruce) Warb., virola (Myristicaceae)

(2) (3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Leaf disk choice test

0.1%

Feeding inhibition = 50%

1. Treatment to larvae.

2. Anthonomus grandis grandis Bohem. (Cotton boll weevil)

Agar plug bioassay

50 µg/mm2

Feeding inhibition = 22.4%

2. Treatment to newly emerged boll weevils for 4 h in dark. (3)

(1) Brownlie, G., Spring, F.S., Stevenson, R., and Strachan, W.S. (1956) J. Chem. Soc., 2419. (2) Abbassy, M.A., Elshazli, A., and Elgayar, F. (1977) Z. Angew. Entomol., 83, 317. (3) Miles, D.H., Ly, A.M., Randle, S.E., Hedin, P.A., and Burks, M.L. (1987) J. Agric. Food Chem., 35, 794.

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Insect Antifeedants

1α-(3′-FURYL)-4β-4aβ-EPOXY-5β,8aαDIMETHYL-3-OXOOCTAHYDRO-1H-2BENZOPYRAN

455

C15H18O4 (262.31)

M.p. : 141–143°

O

O

O O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk bioassay

Conc. / Dose

Efficacy

Remarks

100 µg/cm2

Feeding inhibition = 100%

Treatment to 4th instar larvae for 6–8 h.

31.7 µg/cm2

Feeding inhibition = 82.9%

FI50 = 6.5 µg/cm2 or 0.025 µ mol/cm2 (1)

10.0 µg/cm2

Feeding inhibition = 71.0%

3.17 µg/cm2

Feeding inhibition = 30.0%

(1) Bentley, M.D., Rajab, M.S., Mendel, M.J., and Alford, A.R. (1990) J. Agric. Food Chem., 38, 1400.

© 2005 by CRC Press LLC

456

Opender Koul

1β-(3′-FURYL)-4α-4aα-EPOXY-5β,8aαDIMETHYL-3-OXOOCTAHYDRO-1H-2BENZOPYRAN

C15H18O4 (262.31)

M.p. : 114–115°

O

O

O O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk bioassay

Conc. / Dose

Efficacy

Remarks

100 µg/cm2

Feeding inhibition = 88.8%

Treatment to 4th instar larvae for 6–8 h.

31.7 µg/cm2

Feeding inhibition = 84.7%

FI50 = 7.0 µg/cm2 or 0.027 µ mol/cm2 (1)

10.0 µg/cm2

Feeding inhibition = 83.3%

3.17 µg/cm2

Feeding inhibition = 9.8%

(1) Bentley, M.D., Rajab, M.S., Mendel, M.J., and Alford, A.R. (1990) J. Agric. Food Chem., 38, 1400.

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Insect Antifeedants

GALACTOPYRANOSYL SAPONIN-3

C53H85O22 (1073.56)

OH HO

COOH

O

OH OH

O

O

O

O

OH

HO

HO HO

[α]22 D : +0.7° (MeOH)

O

OH HO

457

O O

HO OH

(1)

(1) SOURCE: Barringtonia asiatica Kurz, fish killer tree (Lecythidacaceae)

(1)

ACTIVITY PROFILE Test Insect Epilachna spp. (Bean beetles)

Test Method Whole leaf assay

Conc. / Dose

Efficacy

1000 µg/ml

Feeding deterrence = 100%

500 µg/ml

Feeding deterrence = 54.54%

100 µg/ml

Feeding deterrence = 0.00%

Remarks Treatment to 3rd and 4th stage larvae prestarved for 2 h. Treatment duration = 24h. (1)

(1) Herlt, A.J., Mander, L.N., Pongoh, E., Rumampuk, R.J., and Tarigan, P. (2002) J. Nat. Prod., 65, 115.

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458

Opender Koul

GALACTOPYRANOSYL SAPONIN-4

C53H83O22 (1071.54)

OH

O

OH

HO

COOH

O

HO

OH OH

O

O HO HO

[α]22 D : +4.6° (MeOH)

O

O OH

HO

O O

HO OH

(1)

(1) SOURCE: Barringtonia asiatica Kurz, fish killer tree (Lecythidacaceae)

(1)

ACTIVITY PROFILE Test Insect Epilachna spp. (Bean beetles)

Test Method Whole leaf assay

Conc. / Dose

Efficacy

Remarks

1000 µg/ml

Feeding deterrence = 100%

500 µg/ml

Feeding deterrence = 63.35%

Treatment to 3rd and 4th stage larvae prestarved for 2 h. Treatment duration = 24h. (1)

100 µg/ml

Feeding deterrence = 39.09%

50 µg/ml

Feeding deterrence = 10.00%

(1) Herlt, A.J., Mander, L.N., Pongoh, E., Rumampuk, R.J., and Tarigan, P. (2002) J. Nat. Prod., 65, 115.

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Insect Antifeedants

GALANTHAMINE CARBONATE

459

C17H21O3N.½H2CO3 (320.39)

M.p. : 218–222° [α]24 D : –98.8° (MeOH)

H H3CO

O OH

2CO3

+ N H

(1)

(1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae)

(1)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina delOrza (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose

Efficacy

0.4%

Feeding ratio = 21.9% (medium feeding inhibition)

0.1%

Feeding ratio = 41.4% (slight feeding inhibition)

0.05%

Feeding ratio = 91.6% (inactive)

Remarks Treatment to 5th instar larvae after 4 h of pre-starvation. (1)

(1) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983) Chem. Pharm. Bull., 31, 2146.

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460

Opender Koul

GALLIC ACID

C7H6O5 (170.12)

M.p. : 253° (dec.) (235–240°)

O

HO

HO

OH OH

(1)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 146 ppm

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to aphids at random. Concentration = EC50 value. (2)

LD (rats): 4 g/kg (s.c.), 5 g/kg (oral) (1) Cochrane, V.W. (1948) Econ. Bot., 2, 145. (2) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229. (3) (1983) Merck Index, p. 621.

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(3)

Insect Antifeedants

GEDUNIN

461

C28H34O7 (482.57)

O

M.p. : 157° (218°) [α]20 D : –44° (CHCl3)

O

O

O O

OAc

(1, 2)

(2,3)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1, 3)

ACTIVITY PROFILE Test Insect 1. Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Bean leaf choice assay

Conc. / Dose 0.1%

Efficacy

Remarks

Feeding inhibition = 50.0%

1. Treatment to 4th instar larvae for 24 h. Concentration = EC50 value. (3)

2. Ostrinia nubilalis (Hubner) (European corn borer)

Leaf disk nochoice assay

500 µg/g

Feeding inhibition = 100.0%

2. Treatment to neonate larvae for 48 h. (4) Data calculated from Reference 4.

(1) Lavie, D., Levy, E.C., and Jain, M.K. (1971) Tetrahedron, 27, 3927. (2) Housley, J.R., King, F.E., King, T.J., and Taylor, P.R. (1962) J. Chem. Soc., 5095. (3) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–198. (4) Arnason, J.T., Philogene, B.J.R., Donskov, N., and Kubo, I. (1987) Entomol. Exp. Appl., 43, 221.

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462

Opender Koul

GENISTEIN 7-RUTINOSIDE (spherobioside)

C27H30O14 (578.52)

M.p. : 203–204° [α]20 D : –73.3° (Pyridine)

HO O

OH O

O

HO

O OH

HO

O O OH

OH

OH

(1)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Heteronychus arator (Fab.) (Black beetle)

Artificial diet feeding

2. Costelytra zealandica (White) (Scarab beetle)

Artificial diet feeding

Test Insect

Efficacy

Remarks

200 µg/ml

Feeding inhibition = 31.6%

1. Treatment to 3rd instar larvae after 24 h of prestarvation. Data calculated from Reference 2. (2)

200 µg/ml

Feeding inhibition = 9.3%

2. Treatment to 3rd instar larvae after 24 h of prestarvation. Data calculated from Reference 2. (2)

(1) Rosler, H., Mabry, T.J., and Kogan, J. (1965) Chem. Ber., 98, 2193. (2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

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Insect Antifeedants

GENTISIC ACID

463

C7H6O4 (154.12)

M.p. : 204.5–205° (199–200°)

COOH OH

HO

(1)

(1, 2)

SOURCE: Alchornea triplinervia (Spreng.) Muell. Arg., tapia (Euphorbiaceae)

(1)

ACTIVITY PROFILE Test Insect Anthonomus grandis Bohem. (Boll weevil)

LD50 (rats): 800 mg/kg (oral)

Test Method

Conc. / Dose

Artificial diet feeding

Efficacy

Remarks

5 mg/4 cm2

Feeding ratio based on T/C = 65.0%

10 mg/4 cm2

Feeding ratio based on T/C = 8.0%

12 mg/4 cm2

Feeding ratio based on T/C = 14.0%

Treatment to freshly emerged boll weevils. Treated/Control = 0 represents absolute antifeedant effect and >100 is attractant. (1)

(3)

(1) Miles, D.H., Hankinson, B.L., and Randle, S.A. (1985) Proc. ACS Symp. Ser. 276, 469. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

464

Opender Koul

GERANIIN

HO

OH HO

HO

C41H28O27 (952.65)

OH

OH

O

M.p. : 360° [α]15 D : –141° (MeOH)

O O O

HO

O

O O

O HO

O

O O

OH

OH HO O

HO

O OH

OH

(1, 2)

(1, 2)

SOURCE: Geranium viscosissimum Fisch and Meyer var. viscossissimum, sticky geranium (Geraniaceae)

(2, 3)

ACTIVITY PROFILE Test Insect 1. Schizaphis graminum (Rondani) (Wheat aphid)

Test Method Artificial diet feeding

Conc. / Dose 179 ppm

Efficacy Feeding inhibition = 50.0%

Remarks 1. Treatment to aphids at random. Concentration = EC50 value (3)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

338 ppm

Feeding inhibition = 50.0%

2. Treatment to aphids at random. Concentration = EC50 value (3)

(1) Okuda, T., Yoshida, T., and Nayeshiro, H. (1976) Tetrahedron Lett., 3721. (2) Yoshida, T., Seno, K., Takama, Y., and Okuda, T. (1982) Phytochemistry, 21, 1180. (3) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.

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Insect Antifeedants

GINKGOLIDE–A

465

C20H24O9 (408.40)

O

[α]D : –39° (Dioxane)

O

O O

M.p. : 280° (dec.)

OH

OH O H H O

O

H

(1, 2)

(1)

SOURCE: Ginkgo biloba L., ginkgo tree (Ginkgoaceae)

(2)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method Leaf disk test

Conc. / Dose

Efficacy

500 µg/disk

Feeding inhibition = 98.0%

50 µg/disk

Feeding inhibition = 57.0%

Remarks Treatment to 3rd instar larvae. (2)

(1) Maruyama, M., Terahara, A., Itagaki, Y., and Nakanishi, K. (1967) Tetrahedron Lett., 299. (2) Matsumoto, T. and Sei, T. (1987) Agric. Biol. Chem., 51, 249.

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466

Opender Koul

GINKGOLIDE–B

C20H24O10 (424.40)

M.p. : >280° (dec.) [α]D : –63° (Dioxane)

O

O O

O

OH

OH O H

O

O

OH

H

(1, 2)

(1)

SOURCE: Ginkgo biloba L., ginkgo tree (Ginkgoaceae)

(2)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method Leaf disk test

Conc. / Dose 500 µg/disk

Efficacy Feeding inhibition = 81.0%

Remarks Treatment to 3rd instar larvae. (2)

(1) Maruyama, M., Terahara, A., Itagaki, Y., and Nakanishi, K. (1967) Tetrahedron Lett., 299. (2) Matsumoto, T. and Sei, T. (1987) Agric. Biol. Chem., 51, 249.

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Insect Antifeedants

GLAUCARUBINE

467

C25H36O10 (496.55)

M.p. : 250–255° (dec.) [α]25 D : +45° (Pyridine)

OH

+69° (MeOH) HO HO

O OCO

HO

OH

O

O

H

(1, 2)

(2,3)

SOURCE: Simarouba glauca DC, bitter wood (Simaroubaceae)

(2, 3)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

(1) (2) (3) (4)

Test Method Leaf disk test

Conc. / Dose 19.8 µg/disk

Efficacy

Remarks

Feeding inhibition = 30–60% after 2 days

Treatment to 3rd instar larvae for 24 h. (4)

Polonsky, J. and Gaudemer, A. (1961) Bull. Soc. Chim., 1432. Bourguigon, N. and Polonsky, J. (1964) Bull. Soc. Chim. Biol., 47, 1145. Kartha, G. and Haas, D.J. (1964) J. Am. Chem. Soc., 86, 3630. Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

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468

Opender Koul

GLAUCARUBINONE

C25H34O10 (494.54)

OH

M.p. : 225–228° (228–230°) [α]D : +50° (MeOH)

HO HO

O OCO

O

OH

O

O

H

(1, 2)

(1)

SOURCE: Simarouba glauca DC, bitter wood (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Heliothis virescens (Fab.) (Tobacco budworm)

Leaf disk test

19.8 µg/disk

Feeding inhibition = 60–90% after 2 days and 30–60% after 6 days.

1. Treatment to 3rd instar larvae. (2)

2. Epilachna varivestis Muls. (Mexican bean beetle)

Whole leaf application

250 ppm

Feeding inhibition = 83.5% after 24 h.

2. Treatment to 4th instar larvae prestarved for 2 h. Data calculated from Reference 3. (3)

3. Spodoptera eridania (Cramer) (Southern armyworm)

Whole leaf application

500 ppm

Feeding inhibition = 50.0% after 24 h.

3. Treatment to freshly molted 5th instar larvae prestarved for 2 h. (3)

(1) Bourguigon, N. and Polonsky, J. (1964) Bull. Soc. Chim. Biol., 47, 1145. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K. (1987) J. Nat. Prod., 50, 442. (3) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

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Insect Antifeedants

GLAUCARUBOL

469

C20H28O8 (396.44)

M.p. : 290–292° (dec.) [α]25 D : +38° (Pyridine)

OH HO HO

O

HO

OH

O

O

H

(1, 2, 3)

(1, 2)

SOURCE: Simarouba glauca DC, bitter wood (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method Leaf disk test

Conc. / Dose 19.8 µg/disk

Efficacy

Remarks

Feeding inhibition = 30–60% after 2 days

Treatment to 3rd instar larvae for 24 h. (3)

(1) Polonsky, J. and Gaudemer, A. (1961) Bull. Soc. Chim., 1432. (2) Stocklin, W. and Geissman, T.A. (1970) Phytochemistry, 9, 1887. (3) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

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470

Opender Koul

GLAUCARUBOLONE

C20H26O8 (394.42)

M.p. : 255–258° [α]D : +34° (Pyridine)

OH HO HO

O

O

OH

O

O

(1, 2)

(1)

SOURCE: Hannoa klaineana Pierre et Engler, African guassia (Simaroubaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Heliothis virescens (Fab.) (Tobacco budworm)

Leaf disk test

19.8 µg/disk

Feeding inhibition = 60–90% after 2 days and 30–60% after 6 days

1. Treatment to 3rd instar larvae. (2)

2. Epilachna varivestis Muls. (Mexican bean beetle)

Whole leaf application

500 ppm

Feeding inhibition = 77.8% after 24 h

2. Treatment to 4th instar larvae prestarved for 2 h. Data calculated from Reference 3. (3)

3. Spodoptera eridania (Cramer) (Southern armyworm)

Whole leaf application

500 ppm

Feeding inhibition = 36.0% after 24 h

3. Treatment to freshly molted 5th instar larvae prestarved for 2 h. (3)

(1) Gaudemer, A. and Polonsky, J. (1965) Phytochemistry, 4, 149. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y, Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442. (3) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

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Insect Antifeedants

GLAUCOLIDE–A

471

C23H28O10 (464.47) OAc

[α]25 D : –29° (CHCl3)

CH2

O

M.p. : 153–154°

O

H

O

O O OAc O

(1, 2)

(1)

SOURCE: Vernonia glauca (L.) Willd., vernonia weed (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method Cellulose millipore filter disk test

Conc. / Dose 1.0%

Efficacy

Remarks

Feeding inhibition rating = 15.6 mg in 48 h

Treatment to 4th stadium larvae. Average deterrence rating based on control-treated disk consumption. (2)

(1) Padolina, W.G., Yoshioka, H., Nakatani, N., Mabry, T.J., Monti, S.A., Davis, R.E., Cox, P.J., Sim, G.A., Watson, W.H., and Wu, I.B. (1974) Tetrahedron, 30, 1161. (2) Smith, C.M., Kester, K.M., and Fischer, N.H. (1983) Biol. Syst. Ecol., 11, 377.

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472

Opender Koul

GLUCOPYRANOSYL GLAUCARUBOLONE

C26H36O13 (556.56)

M.p. : 252–254° [α]22 D : –25.7° (Pyridine)

OH

OH OH

HO HO

OH CH2OH

O

O O

O

O

O

H

(1, 2)

(1)

SOURCE: Simarouba glauca DC, bitter wood (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method Leaf disk test

Conc. / Dose 19.8 µg/disk

12.0 µg/disk

Efficacy Feeding inhibition = 60–90% after 2 days and 0–30% after 6 days

Remarks Treatment to 3rd instar larvae. (2)

Feeding inhibition = 30–60% after 2 days and 0–30% after 6 days

(1) Bhatnagar, S., Polonsky, J., Prange, T., and Pascard, C. (1984) Tetrahedron Lett., 25, 299. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

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Insect Antifeedants

GLYCEOLLIN

473

C20H18O5 (338.36)

Only spectral data given

OH

H

O

OH

O

O

(1, 2)

(1)

SOURCE: Glycine max (L.) Merrill., soybean (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Epilachna varivestis Mulsant (Mexican bean beetle)

Leaf surface application

6.1 µg/mg leaf dry weight

Feeding inhibition = 50.0%

2. Diabrotica undecimpunctata howardi Barber (Southern corn rootworm)

Leaf surface application

3.5 µg/mg leaf dry weight

Feeding inhibition = 50.0%

Treatment to 12-h starved adults until half of the leaf material was consumed (6–8 h). Concentration = FI50

3. Cerotoma trifurcata (Forster) (Bean leaf beetle)

Leaf surface application

Highest conc.

Feeding inhibition = < 50.0% at the highest concentration used

(1) Burden, R.S. and Bailey, J.A. (1975) Phytochemistry, 14, 1389. (2) Fischer, D.C., Kogan, M., and Paxton, J. (1990) Environ. Entomol., 19, 1278.

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It was not possible to calculate EC50 because 50% deterrence was not achieved at the highest treatment level used. (2)

474

Opender Koul

GOSSYPOL

C30H30O8 (518.56)

M.p. : 181–183° [α]19 D : +445 ± 10° (CHCl3)

CHO

OH

OH

CHO

HO

OH

HO

OH

(1)

(1)

SOURCE: Gossypium hirsutum L., cotton (Malvaceae) Also synthetic from gossypol accetate

(2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Styropor method

Conc. / Dose

Efficacy

Remarks

1.0%

Feeding inhibition = 73.6%

Treatment to larvae at random.

0.5%

Feeding inhibition = 61.5%

Treatment duration = 48 h. (2)

0.25%

Feeding inhibition = 34.0%

0.1%

Feeding inhibition = 6.2%

FI50 = 0.42% calculated from Reference 2.

LD50 (rats): 2.57 g/kg (oral) (1) King, T.J. and deSilva, L.B. (1968) Tetrahedron Lett., 261. (2) Meisner, J., Ascher, K.R.S., and Zur, M. (1977) J. Econ. Entomol., 70, 149. (3) El-Nockrashy, A.S., Lyman, C.M., and Dollahite, J.W. (1963) J. Am. Oil Chem. Soc., 40, 14.

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(3)

Insect Antifeedants

GRADOLIDE

475

C25H34O7 (446.54)

M.p. : 154° [α]20 D : –50.9°

OH

OOC

OOC

O

O

(1, 2)

(1)

SOURCE: Laserpitium siler L., mountain lasser wort (Umbelliferae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

1.0%

Feeding deterrence coefficient = 84

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

1.0%

Feeding deterrence coefficient Adults = 146 Larvae = 140

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

1.0%

Feeding deterrence coefficient = 94

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Holub, M., Motl, O., and Samek, Z. (1978) Collect. Czech. Chem. Commun., 43, 2471. (2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

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476

Opender Koul

GRAMINE

C11H14N2 (174.24)

M.p. : 138–139° (131–132°)

N

N H

(1, 2)

(1)

SOURCE: Commercial material

(2)

ACTIVITY PROFILE Test Insect 1. Rhopalosiphum maidis (Fitch) (Corn leaf aphid)

2. Schizaphis graminum (Rondani) (Wheat aphid)

LD50 (mice): 122 mg/kg (ipr.)

Test Method Artificial diet feeding

Artificial diet feeding

Conc. / Dose

Efficacy

Remarks

4 mM

Feeding deterrence = 35.9%

6 mM

Feeding deterrence = 62.6%

1. Treatment to aphids at random for 5 h. (2)

4 mM

Feeding deterrence = 63.9%

6 mM

Feeding deterrence = 66.7%

2. Treatment to aphids at random for 5 h. (2)

(3)

(1) Pachter, I.J., Zacharias, D.E., and Ribeiro, O. (1959) J. Org. Chem., 24, 1285. (2) Corcuera, L.J. (1984) Phytochemistry, 23, 539. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

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Insect Antifeedants

GRISEOFULVIN

477

C17H17O6Cl (352.77)

M.p. : 225–226° [α]17 D : +370° (CHCl3)

OCH3

O OCH3

O

O

H3CO Cl

(1, 2)

(1)

SOURCE: Metabolite of Penicillium griseofulvum Dirck. (filamentous fungi)

(1, 2)

ACTIVITY PROFILE Test Insect Peridroma saucia (Hubner) (Variegated cutworm)

LD50 (rats): 1200 mg/kg (scu)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

28.5 µg/cm2

Feeding inhibition = 14.3%

Treatment to 5th instar larvae for 5 h. (2)

57.0 µg/cm2

Feeding inhibition = 72.8%

(3)

(1) Grove, J.F., MacMillan, J., Mulholland, T.P.C., and Zealley, J. (1952) J. Chem. Soc., 3949, 3967. (2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

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478

Opender Koul

(±)- GROSSAMIDE

OH

C36H36O8N2 (624.69)

OH

M.p. : 174–175° (133–135°)

NH O

HN O

O OH

OCH3 OCH3

(1, 2)

(1, 2)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method Paper disk choice test

Conc. / Dose 5000 ppm

Efficacy Feeding inhibition index = 1.91

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index value below 20 is highly deterrent effect. (1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105. (2) Sakakibara, I., Katsuhara, T., Ikeya, Y., Hayashi, K., and Mitsuhashi, H. (1991) Phytochemistry, 30, 3013.

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Insect Antifeedants

GROSSHEIMIN

479

C15H18O4 (262.31)

M.p. : 205° [α]20 D : +137.7° (MeOH)

CH2

OH

O

CH2

O

O

(1, 2)

(1, 2)

SOURCE: Grosshimia macrocephala Muss. (Push) D. Sosnet Takcht.

(3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

2. Tribolium confusum Duv. (Confused flour beetle)

3. Trogoderma granarium Everts (Khapra beetle)

Test Insect

Efficacy

Remarks

8 mg/cm3

Feeding deterrence coefficient = 51–100

1. Treatment given to adults.

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient Adults = 51–100 Larvae = 51–100

2. Treatment given to both adults and larvae.

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Mukhametzhanov, M.N., Sheichenko, V.I., Rybalko, K.S., and Boryaev, K.I. (1969) Khim. Prir. Soedin., 5, 184. (2) Samek, Z., Holub, M., Vokac, K., Drozdz, B., Jommi, G., Gariboldi, P., and Corbella, A. (1972) Collect. Czech. Chem. Commun., 37, 2611. (3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace Nauk. Inst. Ochr. Roslin, 24, 27.

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480

Opender Koul

GRAYANOTOXIN–I

C22H36O7 (412.51)

M.p. : 260–272° [α]D : –8.8° (EtOH)

OH H OAc HO OH OH OH

(1, 2)

(1, 2)

SOURCE: Rhododendron molle (B.) G. Don, yellow azalea (Ericaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk choice test

12.5 µg/50 mm2

Feeding inhibition = 95.0%

1. Treatment to 4th instar larvae until 95% of control disk was consumed. (1)

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Leaf disk choice test

12.0 µg/50 mm2

Feeding inhibition = 95.0%

2. Treatment to 3rd instar larvae until 95% of control disk was consumed. (1)

(1) Klocke, J.A., Hu, M., Chiu, S., and Kubo, I. (1991) Phytochemistry, 30, 1797. (2) Sukh, Dev and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 94.

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Insect Antifeedants

GRAYANOTOXIN–III

481

C20H34O6 (370.48)

M.p. : 218° [α]15 D : –12°

OH H OH HO OH OH OH

(1, 2)

(1, 2)

SOURCE: Rhododendron molle (B.) G. Don, yellow azalea (Ericaceae) Also isolated from several species of Ericaceae family.

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk choice test

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Leaf disk choice test

Test Insect

Efficacy

Remarks

12.5 µg/50 mm2

Feeding inhibition = 95.0%

1. Treatment to 4th instar larvae until 95% of control disk was consumed. (2)

12.0 µg/50 mm2

Feeding inhibition = 95.0%

2. Treatment to 3rd instar larvae until 95% of control disk was consumed. (2)

(1) Hikino, H., Ogura, M., Ohta, T., and Takemoto, T. (1970) Chem. Pharm. Bull., 18, 1071; 2357. (2) Klocke, J.A., Hu, M., Chiu, S., and Kubo, I. (1991) Phytochemistry, 30, 1797.

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482

Opender Koul

HALOSTACHINE

C9H13ON (151.21) H N

H

M.p. : 43–45° [α]D : –47°

C

OH

(1)

(1)

SOURCE: Halostachys caspica Meyer ex Schrenk., salt wort (Chenopodiaceae)

(1)

ACTIVITY PROFILE Test Insect Locusta migratoria (L.) (Migratory locust)

Test Method

Conc. / Dose

Remarks Treatment at random. (2)

Wafer test

0.025%

Feeding inhibition = 98.0%

Leaf test

0.025%

Feeding inhibition = 48.0%

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Bernays, E.A. and Chapman, R.F. (1977) Ecol. Ent., 2, 1–18.

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Efficacy

Insect Antifeedants

HARRISONIN

483

C27H32O10 (516.54) O

M.p. : 155–156° (164.5–165°)

O

O H3COOC

O OH

HO O O

(1, 4)

(1,3)

SOURCE: Harrisonia abyssinica Oliv., East African medicinal plant (Simaroubaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Leaf disk choice test

Conc. / Dose 20 ppm

Efficacy Feeding inhibition = 100%

Remarks 1. Treatment to larvae at random. (2)

2. Eldana saccharina Walker (Sugar cane borer)

3. Maruca testulalis (Geyer) (Bean pod borer)

Leaf disk test

Leaf disk test

100 µg/disk

Feeding inhibition = 32.0 ± 17.0%

Treatment to early to mid 6th instar larvae. (3)

100 µg/disk

Feeding inhibition = 74.0 ± 13.0%

2. Treatment to 12–h pre-starved late 5th instar larvae.

1 µg/disk

Feeding inhibition = 74.0 ± 16.0%

100 µg/disk

Feeding inhibition = 81.0 ± 14.0%

1 µg/disk

Feeding inhibition = 39.0 ± 8.0%

(3) 3. Treatment to late 5th instar larvae. (3)

(1) Kubo, I., Tanis, S.P., Lee, Y., Miura, I., Nakanishi, K., and Chapya, A. (1976) Heterocycles, 5, 485. (2) Kubo, I. and Nakanishi, K. (1978) Adv. Pestic. Chem., 2, 284. (3) Hassanali, A., Bentley, M.D., Sitayo, E.N.O., Njoroge, P.E.W., and Yatagai, M. (1986) Insect Sci. Applic., 7, 495. (4) Rajab, M.S., Rugutt, J.K., Fronczek, F.R., and Fischer, N.H. (1997) J. Nat. Prod., 60, 822.

© 2005 by CRC Press LLC

484

Opender Koul

HARUNGANIN

C30H36O4 (460.61)

OH

M.p. : 190°

O

OH

OH

(1, 2)

(1)

SOURCE: Harungana madagascariensis Lam. ex Poir., harungana (Clusiaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Glass fiber disk test

10–3 M

Feeding inhibition = 71.18%

1. Treatment to last instar larvae. (2)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk test

10–3 M

Feeding inhibition = 48.27%

2. Treatment to last instar larvae. (2)

3. Heliothis virescens (Fab.) (Tobacco bud worm)

Glass fiber disk test

10–3 M

Feeding inhibition = 60.96%

3. Treatment to last instar larvae. (2)

4. Locusta migratoria (L.) (Migratory locust)

Glass fiber disk test

10–3 M

Feeding inhibition = 42.33%

4. Treatment to last instar larvae. (2)

(1) Ritchie, E. and Taylor, W.C. (1964) Tetrahedron Lett., 1431. (2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem. Ecol., 11, 1593.

© 2005 by CRC Press LLC

Insect Antifeedants

HAUTRIWAIC ACID

485

C20H28O4 (332.44)

M.p. : 183–184° [α]D : –105°

H O

COOH

OH

(1, 2)

(1)

SOURCE: Dodonaea viscosa Jacq., hopseed bush, D. attenuata (Sapindaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method Leaf disk no-choice test

Conc. / Dose

Efficacy

Remarks

2 ppm

Feeding inhibition = 25.0%

50 ppm

Feeding inhibition = 50.0%

Treatment to 3rd instar larvae prestarved for 4 h. Treatment duration = 24 h. (2)

100 ppm

Feeding inhibition = 100.0%

Data calculated from Reference 2.

(1) Bohlmann, F. (1972) Chem Ber., 105, 2123. (2) Taboada, J., Guerrero, C., Camino, L.M., and Aldama, L.L. (1996) Rev. Latinoamer. Quim., 24, 33.

© 2005 by CRC Press LLC

486

Opender Koul

HELENALIN

C15H18O4 (262.30)

M.p. : 225–228° [α]25 D : –102.8° (CHCl3)

O

O

O OH CH2

(1, 2)

(1, 2)

SOURCE: Helenium aromaticum (Hook) Bailey, aromatic weed (Asteraceae)

(3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 151–200

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient Adults = 151–200 Larvae = 101–150

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 151–200

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (3)

LD50 (rats): 125 mg/kg (oral)

(4)

(1) Adams, R. and Herz, W. (1949) J. Am. Chem. Soc., 71, 2546. (2) Lee, K.H., Anuforo, D.C., Huang, E.-S., and Piantadosi, C. (1972) J. Pharm. Sci., 61, 626. (3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace Nauk. Inst. Ochr. Roslin, 24, 27. (4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

HELIOTRINE

487

C16H27O5N (313.39)

H3CO

H C

M.p. : 128° (125–126°) [α]20 D : +63.8° (CHCl3)

C

CH(CH3)2 C

O

OH H HO

O CH2

N

(1, 2, 3)

(1, 2)

SOURCE: Heliotropium arbainense Fres., heliotrope (Boraginaceae)

(3)

ACTIVITY PROFILE Test Insect Choristoneura fumiferana (Clemens) (Spruce bud worm)

Test Method Paper penicillin disk assay

Conc. / Dose 1.6 × 103 M

Efficacy Feeding inhibition = 35.0%

Remarks Treatment to 6th instar larvae.

LD50 (rats): 300 mg/kg (i.p.) (1) (2) (3) (4)

Menshikov, G. (1932) Ber., 65, 974. Menshikov, G. (1935) Ber., 68, 974. Bentley, M.D., Leonard, D.E., Stoddard, W.F., and Zalkow, L.H. (1984) An. Entomol. Soc. Am., 77, 393. Cordell, G.A. (1981) Introduction to Alkaloids, John Wiley & Sons, New York, p. 134.

© 2005 by CRC Press LLC

(3)

(4)

488

Opender Koul

15 – HEPTYLCHAPARRINONE

C27H40O7 (476.61)

Only spectral data given

OH HO HO

O

O

O

O

H

(1, 2)

(1, 2)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

19.8 µg/cm2

Feeding inhibition = 90–100% after 2 days and 60–90% after 6 days of treatment.

Treatment to 3rd instar larvae for 24 h. (2)

6.0 µg/cm2

Feeding inhibition = 60–90% after 6 days of treatment.

3.0 µg/cm2

Feeding inhibition = 30–60% after 2 days and 0–30% after 6 days of treatment.

(1) Caruso, A.J., Polonsky, J., and Rodriguez, B.S. (1982) Tetrahedron Lett., 23, 2567. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

Insect Antifeedants

9 – HEXADECENOIC ACID

489

C16H30O2 (254.41)

M.p. : 32–33° (dec.) B.p. : 180–183°/1 mm

COOH

(1, 2, 3)

(1, 2)

SOURCE: Synthetic

(3)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagan) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk test

Efficacy

Remarks

0.25 mg/cm2

Feeding inhibition = 22.7%

Treatment to larvae of 10–13 mg body weight up to 7 days.

0.05 mg/cm2

Feeding inhibition = 9.7%

Treatment to larvae of 10–13 mg body weight up to 6 days. (3) Data calculated from Reference 3.

(1) Armstrong, E.F. and Hilditch, T.P. (1925) J. Soc. Chem Ind., 44, 182T. (2) Hilditch, T.P. and Vidyarthi, N.L. (1927) J. Soc. Chem Ind., 46, 172T. (3) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC

490

Opender Koul

2′,3′,20,21,22,23 – HEXAHYDROSALANNIN

C34H50O9 (602.76)

Only spectral data given

O O

COO O H

O

AcO H

O

(1)

(1, 2)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

25 µg/cm2

Feeding inhibition = 95.0%

10 µg/cm2

Feeding inhibition = 50.0%

Treatment to freshly molted 3rd instar larvae. Leaf disks examined every 2 h until 95% of control disks were consumed. Concentrations denote the protection levels = PC95 and PC50, respectively. (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC

Insect Antifeedants

HEXAMETHYLDITIN

491

C6H18Sn2 (327.59)

B.p. : 182°/760 mm M.p. : 62–63°/12 mm

Sn

Sn

(1)

(1, 2)

SOURCE: Commercial formulation

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Scolytus mediterraneus Eggers (Fruit bark beetle)

Test Method Leaf dip test

Twig dipping method

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding inhibition = 64.0%

0.2%

Feeding inhibition = 58.0%

1. Treatment to 2cm-long larvae. Field deposit residue leaves were used in each treatment. (1)

0.2%

No twig penetration

0.02%

5% twig penetration

0.002%

48% twig penetration

2. Treatment to 0 to 1-day-old females. (2)

LD50 (rats): 10–25 mg/kg (oral) (1) Ascher, K.R.S. and Moscowitz, J. (1969) Int. Pest Contr., 11, 17. (2) Ascher, K.R.S., Gurevitz, E., Renneh, S., and Nemny, N.E. (1975) Z. Pflkrankh. Pflschutz., 82, 378.

© 2005 by CRC Press LLC

(1)

492

Opender Koul

HILDECARPIN

C17H14O7 (330.29)

HO

[α]D : –244° (MeOH)

O OH O

H3CO H O

O

(1)

(1)

SOURCE: Tephrosia hildebrandtii Vatke, tephrosia (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Leaf disk choice test

2. Maruca testulalis (Geyer) (Bean pod borer)

Leaf disk test

Conc. / Dose 5000 ppm

Efficacy

Remarks

Inactive up to this level of treatment in this insect species.

1. Treatment to larvae at random.

100 µg/disk

Feeding inhibition = 85.8%

Treatment to 5th instar larvae.

10 µg/disk

Feeding inhibition = 51.9%

(1)

(1)

(1) Lwande, W., Hassanali, A., Njoroge, P.W., Bentley, M.D., Monache, F.D., and Jondiko, J.I. (1985) Insect Sci. Applic., 6, 537.

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Insect Antifeedants

HIPPEASTRINE

493

C17H17O7N (315.32)

M.p. : 214–215° [α]22 D : +160° (CHCl3)

N H O OH O

O

O

(1, 2)

(1, 2) SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae)

(1)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina delOrza (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose

Efficacy

0.3%

Medium feeding inhibition, feeding ratio = 27.4%

0.2%

Medium feeding inhibition, feeding ratio = 23.7%

0.1%

Not active at this level, feeding ratio = 55.3%

Remarks Treatment to 5th instar larvae after pre-starvation for 4 h. (3)

(1) Boit, H.G. (1956) Chem Ber., 89, 1129, 2093, 2462. (2) Kitagawa, T., Uyeo, S., and Yokoyama, N. (1959) J. Chem Soc., 3741. (3) Numata, A., Takemura, T., Ohbayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983) Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC

494

Opender Koul

HIRSUTOLIDE

C19H24O9 (396.39)

Oil [α]24 D : +36.3° (CHCl3)

O H2C

O O

HO

OH OAc

OAc

(1, 2)

(1)

SOURCE: Venidium hirsutum Harv., hairy blueberry (Asteraceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

2. Tribolium confusum Duv. (Confused flour beetle)

3. Trogoderma granarium Everts (Khapra beetle)

Test Insect

Efficacy

Remarks

8 mg/cm3

Feeding deterrence coefficient = 51–100

1. Treatment given to adults.

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient Adults = 101–150 Larvae = 151–200

2. Treatment given to both adults and larvae.

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Grabarczyk, H. (1975) Pol. J. Pharmacol. Pharm., 27, 107. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace Nauk. Inst. Ochr. Roslin, 24, 27.

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Insect Antifeedants

HISPIDULIN

495

C16H12O6 (300.27)

HO

M.p. : 304–305° (291–292°)

O OH

H3CO OH

O

(1, 2, 3)

(1, 2)

SOURCE: Tithonia diversifolia (Hemsl.) Gray, Mexican sunflower (Asteraceae)

(3)

ACTIVITY PROFILE Test Insect Philosamia ricini Hutt. (Eri-silkworm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

1.0%

Feeding deterrence = 96.3%

0.5%

Feeding deterrence = 84.0%

Treatment to 0 to 12–h-old 4th instar larvae. (3)

0.25%

Feeding deterrence = 62.7%

0.05%

Feeding deterrence = 49.6%

0.02%

Feeding deterrence = 32.2%

FI50 = 0.063% Calculated from Reference 3.

(1) Herz, W. and Sumi, Y. (1964) J. Org. Chem., 29, 3438. (2) Herz, W. and Sumi, Y. (1966) Tetrahedron, 22, 1907. (3) Dutta, P., Bhattacharyya, P.R., Rabha, L.C., Bordoloi, D.N., Barua, N.C., Chowdhury, P.K., Sharma, R.P., and Barua, J.N. (1986) Phytoparasitica, 14, 77.

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496

Opender Koul

HOMOARGININE

C7H16O2N4 (188.23)

M.p. : 207–209° [α]22 D : +13° (HCl)

COOH

H 2N

C

H NH

(CH2)4NHC NH2

(1, 2)

(1, 2)

SOURCE: Acacia spp. (Fabaceae)

(3)

ACTIVITY PROFILE Test Insect 1. Anacridium melanorhodon arabafrum (Dirsh.) (Tree locust)

2. Locusta migratoria migratoriodes (R & F) (Migratory locust)

Test Method

Conc. / Dose

Glass fiber disk test

Glass fiber disk test

Efficacy

Remarks

1% of disk wt.

Feeding deterrence = 30–60%

2% of disk wt.

Feeding deterrence = 91–100%

1. Treatment to 3rd to 6th instar larvae at random. (3)

0.1% of disk wt.

Feeding deterrence = 30–60%

0.25% of disk wt.

Feeding deterrence = 61–90%

0.5% of disk wt.

Feeding deterrence = 91–100%

(1) Steib, H. (1926) Z. Physiol. Chem., 155, 292. (2) Greenstein, J.P. (1937) J. Org. Chem., 2, 480. (3) Evans, C.S. and Bell, E.A. (1979) Phytochemistry, 18, 1807.

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2. Treatment to male 5th instar nymphs. (3)

Insect Antifeedants

HOMOERIODICTYOL

497

C16H14O6 (302.28)

M.p. : 224° [α]20 D : –28.2° (EtOH))

OCH3 OH

HO

O

OH

O

(1, 2)

(1, 2)

SOURCE: Eriodictyon californicum (Hook and Arn) Torr., (Hydrophylaceae) Semisynthetic preparation as well.

(1, 3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Schizaphis graminum (Rondani) (Green bug)

Artificial diet feeding

0.04%

Feeding deterrence = 50.0%

1. Treatment to 50–75 aphids at random up to 24 h. (3)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

0.07%

Feeding deterrence = 50.0%

2. Treatment to 50–75 aphids at random up to 8 h. Concentrations = EC50 values. (3)

(1) Geissman, T.A. (1940) J. Am. Chem. Soc., 62, 3258. (2) Shinoda, J. and Sato, S. (1929) J. Pharm. Soc, Jap., 49, 64. (3) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC

498

Opender Koul

HOMOGYNOLIDE–A

C20H28O4 (332.44)

H2C

M.p. : 62–65°

O

O O

O

(1)

(1, 2)

SOURCE: Homogyne alpina (L.) Cass., alpine coltsfoot (Asteraceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 150

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 110 Larvae = 136

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 160

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Harmatha, J., Samek, Z., Synackova, M., Novotny, L., Herout, V., and Sorm, F. (1976) Coll. Czech. Chem. Commun., 41, 2047. (2) Nawrot, J., Harmatha, J., and Bloszyk, E. (1986) In E. Donahaye and S. Navarro (eds.), Proc. 4th Int. Work Conf. Stored Product Protection, Tel Aviv, Israel, pp. 591–597.

© 2005 by CRC Press LLC

Insect Antifeedants

HOMOGYNOLIDE–B

499

C20H28O4 (332.44) H2C

Oil

O

O

O

O

(1)

(1, 2)

SOURCE: Homogyne alpina (L.) Cass., alpine coltsfoot (Asteraceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 140

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 165 Larvae = 135

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 170

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Harmatha, J., Samek, Z., Synackova, M., Novotny, L., Herout, V., and Sorm, F. (1976) Coll. Czech. Chem. Commun., 41, 2047. (2) Nawrot, J., Harmatha, J., and Bloszyk, E. (1986) In E. Donahaye and S. Navarro (eds.), Proc. 4th Int. Work Conf. Stored Product Protection, Tel Aviv, Israel, pp. 591–597.

© 2005 by CRC Press LLC

500

Opender Koul

HORDENINE-SULPHATE

[C10H15ON] 2 H2SO4 (330.47)

M.p. : 209–211° (205° anhydrous)

N H2SO4.2 H2O

2

OH

(1)

(1)

SOURCE: Synthetic sample

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Nilaparvata lugens (Stal.) (Brown planthopper)

Sucrose solution feeding

1000 ppm 100 ppm 10 ppm

87% Feeding inhibition 73% Feeding inhibition 51% Feeding inhibition

1. Treatment to adult females. (1)

2. Sogatella furcifera (Horvath) (Planthopper)

Sucrose solution feeding

1000 ppm 100 ppm 10 ppm

86% Feeding inhibition 59% Feeding inhibition 52% Feeding inhibition

2. Treatment to adult females. (1)

3. Laodelphax striatella (Fallen) (Planthopper)

Sucrose solution feeding

1000 ppm 100 ppm 10 ppm

93% Feeding inhibition 89% Feeding inhibition 57% Feeding inhibition

3. Treatment to adult females. (1)

4. Nephotettix cincticeps (Uhler) (Fruit leafhopper)

Sucrose solution feeding

1000 ppm 100 ppm 10 ppm

83% Feeding inhibition 69% Feeding inhibition 39% Feeding inhibition

4. Treatment to adult females. (1)

(1) Kurata, S. and Sogawa, K. (1976) Appl. Ent. Zool., 11, 89.

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Insect Antifeedants

6,7-EPOXY-2,9-HUMULADIENE

501

C15H24O (220.18)

Oil B.p. : 105–106°/1.5 mm [α]30 D : –31.2° (CHCl3)

O

(1)

(1,2)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera littoralis (Boisd.) (Eygyptian cotton leaf worm)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

1. Treatment to 6th instar larvae.

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Choice feeding assay

28.7 nmol/cm2

Feeding deterrence = 50.0%

2. Treatment to adults.

3. Myzus persicae (Sulzer) (Green peach aphid)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

3. Treatment to apterous adult aphids.

4. Rhopalosiphum padi (L.) (Cereal aphid)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

4. Treatment to apterous adult aphids.

5. Sitobion avenae (Fab.) (Grass aphid)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

5. Treatment to apterous adult aphids.

6. Diuraphis noxia (Mordvilko) (Wheat aphid)

Choice feeding assay

>180 nmol/cm2

Feeding deterrence = 50.0%

6. Treatment to apterous adult aphids. Concentrations = EC50 values (1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448. (2) (2000) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC

502

Opender Koul

HYDRASTINE

C21H21O6N (383.40)

M.p. : 162–163.5° [α]D : –141° (CHCl3)

O N

O H

H O

CH3O O

OCH3

(1, 2)

(1)

SOURCE: Hydrastis canadensis L., goldenseal (Papaveraceae)

(1)

ACTIVITY PROFILE Test Insect Diabrotica virgifera virgifera LeConte (Western corn rootworm)

Test Method

Conc. / Dose

Leaf disk test

69.0 nmol/ 1.5 cm2 disk

Efficacy

Remarks

Feeding inhibition = 100% after 24 h

Treatment to adults of cyclodieneresistant insects. (2)

Feeding inhibition = 92.5% after 48 h

Data calculated from Reference 2.

(1) Ohta, M., Tani, H., and Morozumi, S. (1963) Tetrahedron Lett., 859. (2) Mullin, C.A., Mason, C.H., Chou, J., and Linderman, J.R. (1992) In C.A. Mullin and J.G. Scott (eds.), Molecular Mechanism of Insecticide Resistance: Diversity Among Insects, ACS Symp. Ser. 505, Washington, D.C., pp. 288–308.

© 2005 by CRC Press LLC

Insect Antifeedants

14-HYDROAJUGAPITIN-2,15-DIONE

503

C29H40O11 (564.63)

O

[α]20 D : +1.41° (CHCl3)

O H O H O

C2H5CH CH3 COO O

CH2 OCOCH3 OCOCH3

(1, 2)

(1)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy Feeding ratio = 0.48 ± 0.07

(1) Camps, F., Coll, J., and Dargallo, O. (1984) Phytochemistry, 23, 2577. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC

Remarks Treatment to newly ecdysed 5th instar larvae. Data based on the ratio when 50% of control disk was consumed. Feeding ratio < 0.5 is excellent antifeedant activity. (2)

504

Opender Koul

14-HYDRO-15-HYDROXYAJUGAPITIN

C29H44O11 (568.66)

OH

Oil [α]20 D : +1.41° (CHCl3)

O H O H

H HO

C2H5CHCH3COO O

CH2 OCOCH3 OCOCH3

(1, 2)

(1)

SOURCE: Ajuga chamaepitys (L.) Schreb., ground pine (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Leaf disk choice test

1 µg/cm2

Feeding ratio = 0.30 ± 0.09

0.1 µg/cm2

Feeding ratio = 0.37 ± 0.08

Efficacy

(1) Camps, F., Coll, J., and Dargallo, O. (1984) Phytochemistry, 23, 2577. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC

Remarks Treatment to newly ecdysed 5th instar larvae. Data based on the ratio when 50% of control disk was consumed. Feeding ratio < 0.5 is excellent antifeedant activity. (2)

Insect Antifeedants

6-HYDROXYARISTOLOCHIC ACID

505

C17H11O8N (357.28)

M.p. : 269–271°

COOH

O

NO2

O

HO

OCH3

(1)

(1)

SOURCE: Aristolochia albida Duch., Nigerian climber (Aristolochiaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura Fab. (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

1000 ppm

Antifeedant index value = 0

500 ppm

Antifeedant index value = 21.4

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1993) J. Agric. Food Chem., 41, 669.

© 2005 by CRC Press LLC

Remarks Treatment to 4-dayold larvae for 24 hours. Antifeedant index value below 20 highly deterrent. (1)

506

Opender Koul

11-β-HYDROXY-5α-(ANGELOYLOXY) SILPHINEN-3-ONE

C20H24O4 (328.39)

Only spectral data given

OH

O

O

O

(1, 2)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method

Conc. / Dose

Leaf disk choice test

Leaf disk no-choice test

Efficacy

Remarks

14.56 µg/cm2

Feeding inhibition = 50.0%

Treatments to newly emerged 4th instar larvae for ≤ 6 h.

15.04 µg/cm2

Feeding inhibition = 50.0%

Treatments to newly emerged 4th instar larvae for 24 h. Concentration = FI50 value. (1)

(1) Gonzalez-Coloma, A., Gutierrez, C., Cabrera, R., and Reina, M. (1997) J. Agric. Food Chem., 45, 946. (1) Jakupovic, J., Abraham, W.R., and Bohlmann, F. (1985) Phytochemistry, 24, 3048.

© 2005 by CRC Press LLC

Insect Antifeedants

p-HYDROXYBENZALDEHYDE

507

C7H6O2 (122.12)

M.p. : 115–116°

CHO

HO

(1)

(1)

SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae)

(2, 4)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Schizaphis graminum (Rondani) (Green bug)

Artificial diet feeding

0.13%

Feeding inhibition = 50.0%

1. Treatment to 50–75 aphids at random per test for 24 h. (2)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

0.1%

Feeding inhibition = 50.0%

2. Treatment to 50–75 aphids at random per test for 8 h. (3)

3. Locusta migratoria (L.) (Migratory locust)

Leaf disk choice test

0.25%

Feeding inhibition = 70.0%

3. Treatment to 3rd instar larvae. (4)

1.0%

Feeding inhibition = 95.0%

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) J. Chem. Ecol., 7, 273. (3) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489. (4) Woodhead, S., Galeffi, C., and Bettolo, G.B.M. (1982) Phytochemistry, 21, 455.

© 2005 by CRC Press LLC

508

Opender Koul

4-HYDROXY-3-ARYLCOUMARYL QUINONE

C15H8O5 (268.22)

No physical data given

O

O

O

OH

O

(1)

(1)

SOURCE: Synthetic sample

(1)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Artificial diet feeding

Conc. / Dose 200 µg/g

Efficacy

Remarks

Feeding inhibition = 35.1%

Treatment to 24-h pre-starved 3rd instar larvae. (1) Data calculated from Reference 1.

(1) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC

Insect Antifeedants

p-HYDROXYBENZOIC ACID

509

C7H6O3 (138.12)

M.p. : 213–214°

COOH

OH

(1)

(1)

SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae) Pteridium aquilinum L. Kuhn, bracken fern (Pteridophyta)

(2, 4)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Schizaphis graminum (Rondani) (Green bug)

Artificial diet feeding

0.36%

Feeding inhibition = 50.0%

1. Treatment to 50–75 aphids at random per test for 24 h. (2)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

0.2%

Feeding inhibition = 50.0%

2. Treatment to 50–75 aphids at random per test for 8 h. (3)

3. Pieris brassicae (L.) (Large white butterfly)

Leaf disk no-choice test

7.2 × 10–2 M

Feeding inhibition index = 1.0 Feeding ratio = 2.87

3. Treatment to 2-day-old 5th instar larvae. (4)

(1) (2) (3) (4)

(1994) Dictionary of Natural Products, Chapman & Hall, London. Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) J. Chem. Ecol., 7, 273. Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489. Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.

© 2005 by CRC Press LLC

510

Opender Koul

6β-HYDROXYEREMOPHILENOLIDE

C15H22O3 (250.34)

M.p. : 208° [α]D : +205.8° (CHCl3)

H O O

OH

(1)

(1, 2) SOURCE: Petasites albus (L.) J. Gaertn., butterbur (Asteraceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = − 3

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = Adults = 84 Larvae = 82

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence = coefficient = 59

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Novotny, L., Herout, V., and Sorm, F. (1964) Collect. Czech. Chem. Commun., 29, 2187. (2) Harmatha, J. and Nawrot, J. (1984) Biochem. Syst. Ecol., 12, 95.

© 2005 by CRC Press LLC

Insect Antifeedants

γ-HYDROXYFERRUGININ–A

OH

511

C30H36O5 (476.61)

Only spectral data given

O

OH

OH

OH

(1, 2)

(1)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera exempta (Walker) (Nut grass armyworm)

Glass fiber disk test

10–3 M

Feeding inhibition = 56.36%

1. Treatment to last instar larvae. (2)

2. Heliothis virescens (Fab.) (Tobacco bud worm)

Glass fiber disk test

10–3 M

Feeding inhibition = 47.97%

2. Treatment to last instar larvae. (2)

3. Helicoverpa armigera (Hubner) (Gram pod borer)

Glass fiber disk test

10–3 M

Feeding inhibition = 38.69%

3. Treatment to last instar larvae. (2)

4. Locusta migratoria (L.) (Migratory locust)

Glass fiber disk test

10–3 M

Feeding inhibition = 56.42%

4. Treatment to last instar larvae. (2)

(1) Delle Monache, F., Torres, F., Bettolo, G.B.M., and Alves De Lima, R. (1980) Lloydia, 43, 487. (2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem. Ecol., 11, 1593.

© 2005 by CRC Press LLC

512

Opender Koul

γ-γ-HYDROXYFERRUGININ–A

OH

C30H36O6 (492.61)

No physical data given

O

OH

OH

OH

OH

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera exempta (Walker) (Nut grass armyworm)

Test Method Glass fiber disk test

Conc. / Dose 10–3 M

Efficacy

Remarks

Feeding inhibition = 62.64%

1. Treatment to last instar larvae. (1)

(1) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem. Ecol., 11, 1593.

© 2005 by CRC Press LLC

Insect Antifeedants

7-HYDROXYFLAVONONE

HO

513

C15H10O3 (238.24)

M.p. : 244° (240°)

O

O

(1, 2)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nut grass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dual choice test

Glass fiber disk dual choice test

Efficacy

Remarks

100 ppm

Feeding inhibition = 73.0%

10 ppm

Feeding inhibition = 59.0%

1. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae were prestarved for 4 h. (2)

100 ppm

Feeding inhibition = 17.0%

2. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae were prestarved for 4 h. (2)

(1) Looker, J.H., and Hanneman, W.W. (1962) J. Org. Chem., 27, 381. (2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

514

Opender Koul

2′-HYDROXYFORMONONETIN

HO

C16H12O5 (284.27)

M.p. : 215–217° (220–222°)

O

O

OCH3

HO

(1)

(1)

SOURCE: Synthetic sample

(1)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Artificial diet feeding

Conc. / Dose 14 µg/g

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 24-h pre-starved 3rd instar larvae. (1) Data calculated from Reference 1.

(1) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC

Insect Antifeedants

2′-HYDROXYGENISTEIN

HO

515

C15H10O6 (286.24)

M.p. : 270–273°

O

OH

O

OH

HO

(1, 2)

(1)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Artificial diet feeding

Conc. / Dose 20 µg/g

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 24-h pre-starved 3rd instar larvae. (2)

(1) Lane, G.A., Sutherland, O.R.W., and Skipp, R.A. (1987) J. Cherm. Ecol., 13, 771. (2) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC

516

Opender Koul

3-HYDROXYGRANDIOLIDE

C15H22O4 (266.34)

M.p. : 65° [α]24 D : –25° (CHCl3)

CH2

H

OH

HO

H O

O

(1, 2)

(1)

SOURCE: Arctotis grandis Thunb., African daisy (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 40.9

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient Adults = 89.5 Larvae = 89.6

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = − 37.7

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Holub, M., Samek, Z., Le, V.N.P., Grabarczyk, H., and Drozdz, B. (1979) Conf. on Isoprenoids, Torun., p. 66. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk. Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC

Insect Antifeedants

5-HYDROXY-2-HEXEN-4-OLIDE

H

517

C6H8O3 (128.13)

Colourless oil Distilled at 90–100°/0.05 mm

H

O

O OH

(1, 2)

(1)

SOURCE: Osmunda japonica (L.) Thunb., flowering fern (Osmundaceae)

(2)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina delOrza (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose 0.78%

Efficacy Medium feeding inhibition, feeding ratio = 38.0%

Remarks Treatment to 5th instar larvae after pre-starvation for 4 h. (2)

(1) Hollenbeak, K.H. and Kuehne, M.E. (1974) Tetrahedron, 30, 2307. (2) Numata, A., Hokimoto, K., Takemura, T., and Fukui, S. (1983) Appl. Ent. Zool., 18, 129.

© 2005 by CRC Press LLC

518

Opender Koul

5-HYDROXY-1-(4-HYDROXY-3-METHOXY PHENYL) DECAN-3-ONE

C17H26O4 (294.39)

Oil [α]D : +26.5° (CHCl3)

OH

O H3CO

HO

(1, 2, 3)

(1, 2) SOURCE: Aframomum melegueta (Roscoe) K. Schum. Cameroon cardamom (Zingiberaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method

Conc. / Dose

Paper disk choice assay

5000 ppm

Antifeedant index value = 8.2

2500 ppm

Antifeedant index value = 3.0

1000 ppm

Antifeedant index value = 19.6

Efficacy

(1) Kikuzaki, H., Tsai, S., and Nakatani, N. (1992) Phytochemistry, 31, 1783. (2) Escoubas, P., Lajide, L., and Mizutani, J. (1995) Phytochemistry, 40, 1097. (3) Connell, D.W. and Sutherland, M.D. (1969) Aust. J. Chem., 22, 1033.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index value below 20 = highly deterrent. (2)

Insect Antifeedants

2α-HYDROXYISOCOSTIC ACID

519

C15H22O3 (250.34)

M.p. : 153–156° [α]20 D : +48.4° (CHCl3)

HO

CH2 H COOH

(1)

(1)

SOURCE: Dittrichia viscosa (L.) Grenter., inula (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 151.1

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient Adults = 138.2 Larvae = 143.9

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 69.5

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (1)

(1) Daniewski, W.M., Kroszczynski, W., Bloszyk, E., Drozdz, B., Nawrot, J., Rychlewska, U., Budesinsky, M., and Holub, M. (1986) Collect. Czech. Chem. Commun., 51, 1710.

© 2005 by CRC Press LLC

520

Opender Koul

5-HYDROXYISODERRICIN (7-methyl-grabanin)

C21H22O4 (338.40)

H3CO

No physical data given

O

OH

O

(1)

(1)

SOURCE: Tephrosia villosa Pers., tephrosia (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nut grass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dualchoice test

Glass fiber disk dualchoice test

Efficacy

Remarks

100 ppm

Feeding inhibition = 71.0%

10 ppm

Feeding inhibition = 42.0%

1. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae were prestarved for 4 h. (1)

100 ppm

Feeding inhibition = 53.0%

2. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae were prestarved for 4 h. (1)

(1) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

Insect Antifeedants

3-HYDROXY-4-METHOXY CINNAMIC ACID

521

C10H10O4 (194.19)

M.p. : 233–234° (228°)

COOH

OH OCH3

(1, 2)

(1, 3)

SOURCE: Commercial sample (2) Also isolated from Cimicifuga racemosa (L.) Nutt., black bugbane (Ranunculaceae) and Catalpa ovata Don., catalpa (Bignoneaceae) ACTIVITY PROFILE Test Insect Pieris brassicae (L.) (Large white butterfly)

Test Method Leaf disk no-choice test

Conc. / Dose 5.2 × 10–2 M

Efficacy

Remarks

Feeding inhibition index = 1.0 Feeding ratio = 2.82

Treatment to 2-dayold 5th instar larvae. (2) Ratio < 20 highly deterrent

(1) Robinson, R. and Sugasawa, S. (1931) J. Chem. Soc., 3169. (2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187. (3) Blasé, F.R. and Banerjee, K. (1995) Synth. Commun., 25, 3187.

© 2005 by CRC Press LLC

522

Opender Koul

1- (4-HYDROXY-3-METHOXYPHENYL) DECAN-3-ONE

C17H26O3 (278.39)

M.p. : 27–29° (31–32°)

O H3CO

HO

(1, 2)

(1, 2)

SOURCE: Aframomum melegueta (Roscoe) K. Schum., Cameroon cardamom (Zingiberaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (subterranean termite)

Test Method

Conc. / Dose

Paper disk choice assay

7500 ppm

Antifeedant index value = 10.2

5000 ppm

Antifeedant index value = 22.8

1000 ppm

Antifeedant index value = 17.6

Efficacy

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index value below 20 considered as highly deterrent. (2)

(1) Tackie, A.N., Dwuma-Dadu, D., Ayim, J.S.K., Dabra, T., Knapp, J.E., Slatken, D.J., and Schiff, P.L. (1975) Phytochemistry, 14, 853. (2) Escoubas, P., Lajide, L., and Mizutani, J. (1995) Phytochemistry, 40, 1097.

© 2005 by CRC Press LLC

Insect Antifeedants

4′-HYDROXY-7-METHOXYFLAVAN

523

C16H16O3 (256.30)

M.p. : 148.5–149.5° [α]21 D : –15.6° (EtOH)

H OH H H3CO

O

(1, 2)

(1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae)

(2)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina delOrza (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose

Efficacy

Remarks

0.8%

Medium feeding inhibition, feeding ratio = 20.8%

Treatment to 5th instar larvae after pre-starvation for 4 h.

0.4%

Slight feeding inhibition, feeding ratio = 27.5%

0.2%

Strong feeding inhibition, feeding ratio = 19.1%

0.2% treatment level has been exceptionally active level. (2)

0.05%

Not active at this level, feeding ratio = 66.5%

(1) Cooke, R.G. and Down, J.G. (1971) Aust. J. Chem., 24, 1257. (2) Numata, A., Takemura, T., Ohbayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983) Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC

524

Opender Koul

(–)-3′-HYDROXY-4′-METHOXY-7HYDROXY-8-METHYLFLAVAN

C17H18O4 (286.33)

[α]20 D : –31° (CHCl3)

OH OCH3

HO

O

(1)

(1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae)

(2)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina delOrza (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose

Efficacy

0.8%

Strong feeding inhibition, feeding ratio = 7.2%

0.2%

Strong feeding inhibition, feeding ratio = 11.6%

0.05%

Slight feeding inhibition, feeding ratio = 35.8%

Remarks Treatment to 5th instar larvae after pre-starvation for 4 h. (1)

(1) Numata, A., Takemura, T., Ohbayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983) Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC

Insect Antifeedants

2-HYDROXY-4-METHOXY BENZALDEHYDE

525

C8H8O3 (152.15)

B.p. : 75–78°/0.4 mm n 25 D

: 1.5727

CHO OH

OCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding inhibition = 100% up to 6 h.

Treatment to adult beetles. (1)

0.5%

Feeding inhibition = 100% up to 22 h.

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.

© 2005 by CRC Press LLC

526

Opender Koul

2-HYDROXY-3-METHOXY BENZALDEHYDE

C8H8O3 (152.15)

B.p. : 80–85°/0.5 mm n25 D

: 1.5730

CHO OH

OCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk test

Conc. / Dose 0.5%

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.

© 2005 by CRC Press LLC

Efficacy

Remarks

Feeding inhibition = 100% up to 22 h.

Treatment to adult beetles. (1)

Insect Antifeedants

1- (4-HYDROXY-3-METHOXYPHENYL) DEC-5-EN-3-ONE

527

C17H24O3 (276.38)

Oil

O H3CO

HO

(1, 2)

(1, 2)

SOURCE: Aframomum melegueta (Roscoe) K. Schum. (Cameroon Cardamom Zingiberaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method

Conc. / Dose

Paper disk choice assay

7500 ppm

Antifeedant index value = 17.5

5000 ppm

Antifeedant index value = 15.2

Efficacy

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index value below 20 highly deterrent. (2)

(1) Tackie, A.N., Dwuma-Dadu, D., Ayim, J.S.K., Dabra, T., Knapp, J.E., Slatken, D.J., and Schiff, P.L. (1975) Phytochemistry, 14, 853. (2) Escoubas, P., Lajide, L., and Mizutani, J. (1995) Phytochemistry, 40, 1097.

© 2005 by CRC Press LLC

528

Opender Koul

E-3-(4-HYDROXY-3-METHOXYPHENYL) –N-2[4-HYDROXYPHENYLETHYL]-2-PROPENAMIDE

C18H19O4N (313.35)

Only spectral data given

OH

O H3CO N H HO

(1, 2)

(1, 2)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae)

(2)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method

Conc. / Dose

Paper disk choice assay

7500 ppm

Antifeedant index value = 8.5

5000 ppm

Antifeedant index value = 24.8

Efficacy

(1) Yoshihara, T., Takamatsu, S., and Sakamura, S. (1978) Agric. Biol. Chem., 42, 623. (2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index value below 20 highly deterrent. (2)

Insect Antifeedants

6α-HYDROXYGRINDELIC ACID

529

C20H32O4 (336.47)

M.p. : 106–108° [α]D : +19.3° (CHCl3)

COOH

O

OH (α)

(1)

(1)

SOURCE: Grindelia humilis Hook and Arn, hairy gumweed (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 0.02%

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 50–75 aphids at random per test for 24 h. (1)

(1) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

© 2005 by CRC Press LLC

530

Opender Koul

6β-HYDROXYGRINDELIC ACID

C20H32O4 (336.47)

M.p. : 147–150° [α]D : –151.5° (CHCl3)

COOH

O

OH (β)

(1)

(1)

SOURCE: Grindelia humilis Hook and Arn, hairy gumweed (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 0.02%

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 50–75 aphids at random per test for 24 h. (1)

(1) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

© 2005 by CRC Press LLC

Insect Antifeedants

18-HYDROXYGRINDELIC ACID

531

C20H32O4 (336.47)

Oil [α]D : –82.6° (CHCl3)

COOH

O

OH

(1)

(1, 2)

SOURCE: Chrysothamnus nauseosus (Pall.) Britt., rubber rabbitbush (Asteraceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 0.002%

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 50–75 aphids at random per test for 24 h. (1, 2)

(1) Rose, A.F. (1980) Phytochemistry, 19, 2689. (2) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

© 2005 by CRC Press LLC

532

Opender Koul

6-HYDROXYPICRASIN–B

C21H28O7 (392.45)

[α]D : –48.2° (CHCl3)

OCH3

O

M.p. : 285–290°

O

HO

O H O H OH

(1, 2)

(1)

SOURCE: Soulamea pancheri Brongn. & Griseb. (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method Leaf disk test

Conc. / Dose 19.8 µg/cm2

Efficacy

Remarks

Feeding inhibition = 30–60% after 2 days and 0–30% after 6 days

1. Treatment to 3rd instar larvae. (2)

(1) Viala, B. and Polonsky, J. (1970) Compt. Rend., 271C, 410. (2) Lidert, Z., Wing, K., Polonsky, J., Imakuram, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

Insect Antifeedants

6-HYDROXYSANDORICIN

533

C31H40O12 (604.65)

O

M.p. : 250–255° (dec.)

O

O

O

O O

O OH

CH2

O

OH COOCH3

(1)

(1)

SOURCE: Sandoricum koetjape (Burm. F.) Merr., Santol (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Artificial diet two-choice assay

25 ppm

Feeding inhibition = 64.0%

Treatment to newly hatched larvae for 16–20 h. (1)

2. Ostrinia nubilalis (Hubner) (European corn borer)

Artificial diet two-choice assay

200 ppm

Feeding inhibition = 70.0%

Data calculated from Reference 1.

(1) Powell, R.G., Mikolajczak, K.L., Zilkowski, B.W., Mantus, E.K., Cherry, D., and Clardy, J. (1991) J. Nat. Prod., 54, 241.

© 2005 by CRC Press LLC

534

Opender Koul

2-HYDROXYSENEGANOLIDE

C27H35O9 (503.54) O

Amorphous powder [α]D : +61° (MeOH)

O

O

O

O O

HO

H

OH O

(1)

(1)

SOURCE: Khaya senegalensis (Desv.) A. Juss., dry-zone mahogany (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis Boisd. (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

200 ppm (4 µg/cm2)

Feeding inhibition = 50%

Treatment to 3rd instar larvae until the larvae had eaten approximately 50% of one of the disks. (1)

(1) Nakatani, M., Abdelgaleil, S.A.M., Kurawaki, J., Okamura, H., Iwagawa, T., and Doe, M. (2001) J. Nat. Prod., 64, 1261.

© 2005 by CRC Press LLC

Insect Antifeedants

21- (R,S)-HYDROXYTOONACILID

535

C31H38O11 (586.63)

M.p. : 188–189°

O

[α]20 D : +37° (CHCl3) O AcO OH

AcO

O

H O

CH2

COOCH3

(1)

(1)

SOURCE: Toona ciliata M.J. Roem var. australis, red cedar (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method

Conc. / Dose

Leaf disk test

25–50 ppm

Efficacy

Remarks

Feeding inhibition = 100%.

Treatment to adult beetles. Absolute antifeedant effect at this level of treatment within 24 h. (1)

(1) Kraus, W. and Grimminger, W. (1980) Nouv. J. de Chimie., 4, 651.

© 2005 by CRC Press LLC

536

Opender Koul

23- (R,S)-HYDROXYTOONACILID

C31H38O11 (586.63)

M.p. : 163–164°

OH

[α]20 D : +66.7° (CHCl3) O AcO O AcO

O

H O

CH2

COOCH3

(1)

(1)

SOURCE: Toona ciliata M.J. Roem var. australis, red cedar (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf disk test

Conc. / Dose 0.2%

Efficacy

Remarks

Feeding inhibition = 100%.

Treatment to adult beetles. Absolute antifeedant effect at this level of treatment within 24 h. (1)

(1) Kraus, W. and Grimminger, W. (1980) Nouv. J. de Chimie., 4, 651.

© 2005 by CRC Press LLC

Insect Antifeedants

4β-HYDROXYWITHANOLIDE–E

537

C28H38O8 (502.60)

M.p. : 205–214° (197–198°) [α]22 D : +107° (dioxane)

OH

OH

O

O

O

OH O OH

(1, 2)

(1, 2)

SOURCE: Physalis peruviana L., Peruvian ground cherry (Solanaceae)

(2, 3)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Styropor test

Leaf residue test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding inhibition = 98.3%

0.01%

Feeding inhibition = 72.6%

1. Treatment to larvae of 170 to 190 mg body weight. (3) Data calculated from Reference 3.

0.005%

Feeding inhibition = 44.9%

0.1%

Negative weight gain of 3.23 against +12.24 in controls Negative weight gain of 3.5 against +11.59 in controls

2. Treatment to 4th instar larvae for 48 h. Weight loss considered as a result of antifeedant effect. (4)

Feeding inhibition = 50.0%

3. Treatment to larvae. Concentration is FI50 value. (5)

0.05%

3. Helicoverpa zea (Boddie) (Corn earworm)

Leaf disk test

250 ppm

(1) Kirson, I., Abraham, A., Sethi, P.D., Subramanian, S.S., and Glotter, E. (1976) Phytochemistry, 15, 340. (2) Sakurai, K., Ishii, H., Kobayashi, S., and Twao, T. (1976) Chem. Pharm. Bull., 24, 1403. (3) Ascher, K.R.S., Nemney, N.E., Eliyahu, M., Kirson. I., Abraham, A., and Glotter, E. (1980) Experientia, 36, 998. (4) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson. I. (1981) Phytoparasitica, 9, 197. (5) Baumann, T.W. and Meier, C.M. (1993) Phytochemistry, 33, 317.

© 2005 by CRC Press LLC

538

Opender Koul

O

HYRCANOSIDE

C34H48O14 (680.74) O

M.p. : 200–210° (177–179°) [α]20 D : +7.4° (MeOH)

CHO

OH O O HO

OH O

HO

OH

O

OH

OH

(1)

(1, 2)

SOURCE: Coronilla varia L., crownvetch (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Peridroma saucia (Hubner) (Variegated cutworm)

Test Method

Conc. / Dose

Leaf disk choice test

Efficacy

Remarks

14.25 µg/cm2

Feeding inhibition = 41.5%

1. Treatment to 5th instar larvae for 5 h. (2)

28.5 µg/cm2

Feeding inhibition = 60.5%

57.0 µg/cm2

Feeding inhibition = 87.8%

(1) Hembree, J.A., Chang, C.J., McLaughlin, J.L., Peck, G., and Cassady, J.M. (1979) J. Nat. Prod., 42, 293. (2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.

© 2005 by CRC Press LLC

Insect Antifeedants

IMPERATORIN

539

C16H14O4 (270.28)

M.p. : 102°

O O

O

O

(1, 2)

(1)

SOURCE: Clausena anisata (Willd.) Hook F. Ex Benth., samanobere (Rutaceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera exempta (Walker) (Nutgrass armyworm)

LD50 (mice): 330 mg/kg (ipr.)

Test Method Leaf disk test

Conc. / Dose

Efficacy

100 ppm

Feeding inhibition observed.

500 ppm

Feeding inhibition observed.

Remarks Treatment to larvae pre-starved for 2 h. No quantitative data recorded. (2)

(3)

(1) Govindachari, T.R., Pai, B.R., Subramaniam, P.S., and Muthukumaraswamy, N. (1968) Tetrahedron, 24, 753. (2) Gebreyesus, T. and Chapya, A. (1983) In T.R. Odhiambo (ed.), Natural Products for Innovative Pest Management, Current Themes in Tropical Science, Pergamon Press, Oxford, 237–241. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

540

Opender Koul

2-IODOOCTADECANOIC ACID

C18H35O2I (410.38)

M.p. : 66°

I

COOH

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk test

0.05 mg/cm2

Efficacy

Remarks

Feeding inhibition = 76.3%

Treatment to larvae of 10 to 13 mg body weight for 6 days. (2) Data calculated from Reference 2.

(1) Frewing, J.J. (1944) Proc. Roy. Soc., A182, 270. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC

Insect Antifeedants

IPOLAMIIDE

541

C17H26O11 (406.39)

M.p. : 144–145° [α]13 D : –136° (dioxane)

COOCH3 OH

H O OH

H O-β-Glc

(1, 3)

(1, 2)

SOURCE: Stachytarpheta mutabilis Vahl., velvet berry (Verbenaceae)

(3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Leaf disk test

0.1%

Feeding inhibition = 100%

1.Treatment to larvae on dry weight basis. (3)

2. Locusta migratoria (L.) (Migratory locust)

Leaf disk test

2.0%

Feeding inhibition = 100% Feeding inhibition = 97.0% Feeding inhibition = 29.0%

2. Treatment to insects approximately halfway through final larval stadium. (3)

Feeding inhibition = 100% Feeding inhibition = 43.0% Not active

4. Treatment to insects approximately halfway through final larval stadium. (3)

0.2% 0.02%

3. Schistocerca gregaria (Forsk.) (Desert locust)

Leaf disk test

2.0% 0.2% 0.02%

(1) Scarpati, M.L. (1969) Gazz. Chim. Ital., 99, 1150. (2) Tantisewie, B. and Sticher, O. (1975) Phytochemistry, 14, 1462. (3) Bernays, E. and DeLuca, C. (1981) Experientia, 37, 1289.

© 2005 by CRC Press LLC

542

Opender Koul

ISOALANTOLACTONE

C15H20O2 (232.32)

M.p. : 115° (109–110°) [α]D : +172° (CHCl3)

O O

H

CH2

CH2

(1, 2)

(1, 2)

SOURCE: Inula helenium L., eleocampane (Asteraceae) Eupatorium quadrangularae L., joe-pye-weed (Asteraceae)

(1, 3) (4)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 108

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 200 Larvae = 175

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 107

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (3)

4. Atta cephalotes (L.) (Leaf cutter ant)

Rye flake forced choice test.

0.2 mg or 4 µg/flake

Feeding inhibition = 36.4%

4. Treatment given to adult workers. Data calculated from Reference 4. (4)

Test Insect

Efficacy

(1) Asselineau, C. and Borg, S. (1958) Compt. Rend., 246, 1874. (2) Marshall, J.A. and Cohen, N. (1964) J. Org. Chem., 29, 3727. (3) Streibl, M., Nawrot, J., and Herout, V. (1983) Biochem. Syst. Ecol., 11, 381. (4) Hubert, T.D., Okunade, A.L., and Wiemer, D.F. (1987) Phytochemistry, 26, 1751.

© 2005 by CRC Press LLC

Remarks

Insect Antifeedants

Ent-ISOALANTOLACTONE

543

C15H20O2 (232.32)

M.p. : 112–115°

O O

H

CH2

CH2

(1, 2)

(1)

SOURCE: Locopholea heterophylla, liverwort (Pteridophyta)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 117

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 139 Larvae = 170

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 127

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Konecny, K., Ubik, K., Vasickova, S., Streibl, M., and Herout, V. (1982) Collect. Czech. Chem. Commun., 47, 3164. (2) Streibl, M., Nawrot, J., and Herout, V. (1983) Biochem. Syst. Ecol., 11, 381

© 2005 by CRC Press LLC

544

Opender Koul

ISOASARONE

C12H16O3 (208.26)

M.p. : 23.0–23.5° (25°)

OCH3

B.p. : 145–147°/2 mm H3CO

OCH3

CH2

(1, 2)

(1, 2)

SOURCE: Piper futokadzura Sieb. et Zucc., Japanese piper (Piperaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

1%

Feeding deterrence = 90–100%

0.5%

Feeding deterrence = 90–100%

0.1%

No activity

Remarks Treatment to 3rd instar larvae. (1)

(1) Matsui, K., Wada, K., and Munakata, K. (1976) Agric. Biol. Chem., 40, 1045. (2) de O. Santos, B.V., da Cunha, E.V.L., de O. Chaves, M.C., and Gray, A.I. (1998) Phytochemistry, 49, 1381

© 2005 by CRC Press LLC

Insect Antifeedants

ISOBERGAPTEN

545

C12H8O4 (216.19)

M.p. : 222° (217–219°)

OCH3

O

O

O

(1, 2, 3)

(1, 2)

SOURCE: Pimpinella saxifraga L., pimpinella (Apiaceae)

(1, 3)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

100 ppm

Feeding ratio = 7.0%

10 ppm

Feeding ratio = 3.0%

5 ppm

Feeding ratio = 4.0%

Treatment to 3rd instar larvae. Feeding ratio from 0 to 20% considered to be highly deterrent. (3)

(1) Wessely, F. and Nadler, E. (1932) Montash, 60, 142. (2) Spath, E. and Simon, A.F.J. (1936) Montash, 67, 349. (3) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC

546

Opender Koul

ISOBOLDINE

C19H21O4N (327.38) H3CO

M.p. : 127° [α]31 D : +60° (CHCl3)

N HO

H3CO OH

(1)

(1) SOURCE: Cocculus trilobus DC., Japanese mu fang (Menispermaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Trimeresia miranda Butler (Cutworm)

Leaf disk test

200 ppm

Threshold level of feeding deterrence

1. Treatment to larvae at random. Feeding = 0–20% of controls. (1)

2. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk test

200 ppm

0–20% consumption of controls

2. Treatment to 3rd instar larvae. (1)

100 ppm

20–50% consumption of controls

(1) Wada, K. and Munakata, K. (1968) J. Agric. Food Chem., 16, 471.

© 2005 by CRC Press LLC

Insect Antifeedants

ISOBRUCEIN–A

547

C26H34O11 (522.55)

M.p. : 200–202° [α]D : +43° (CHCl3)

OH HO OH

COOCH3 O

H

O

OCO

O H

O

H

(1, 2, 3)

(1, 2)

SOURCE: Soulamea soulameoides (Gray) Nooteboom (Simaroubaceae)

(2, 3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Heliothis virescens (Fab.) (Cotton budworm)

Leaf disk test

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

3. Epilachna varivestis Muls. (Mexican bean beetle)

Test Insect

Efficacy

Remarks

15 µg/cm2

Feeding inhibition = 95.0%

1. Treatment to 3rd instar larvae. Concentration = PC95 (3)

Leaf disk test

8 µg/cm2

Feeding inhibition = 95.0%

2. Treatment to 3rd instar larvae. Concentration = PC95 (3)

Whole leaf application

200 ppm

Feeding inhibition = 87.1%

3. Treatment to 4th instar larvae for 24 h. Larvae pre-starved for 2 h. Data calculated from Reference 4. (4)

(1) Polonsky, J., Baskevitch-Varon, Z., and Sevenet, T. (1975) Experientia, 31, 1113. (2) Handa, S.S., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1983) J. Nat. Prod., 46, 359. (3) Klocke, J.A., Arisawa, M., Handa, S.S., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1985) Experientia, 41, 7. (4) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC

548

Opender Koul

ISOBRUCEIN–B

C23H28O11 (480.47)

M.p. : 255–258° [α]22 D : +17° (MeOH)

OH HO OH

COOCH3 O

H OCOCH3

O

O H

O

H

(1, 2)

(1)

SOURCE: Picrolemma pseudocoffea Ducke. (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Cotton budworm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

19.8 µg/cm2

Feeding inhibition = 60–90% after 6 days of treatment.

1. Treatment to 3rd instar larvae. (2)

3 µg/cm2 to 12 µg/cm2

Feeding inhibition = 60–90% after 2 days and 0–30% after 6 days of treatment.

(1) Moretti, C., Polonsky, J., Vuilhorgne, M., and Prange, T. (1982) Tetrahedron Lett., 23, 647. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

Insect Antifeedants

3β-ISOBUTYRYLOXY-1-1-OXOMELIAC-8 (30)-ENATE

549

C31H40O8 (540.65)

O

M.p. : 211–213°

O H3COOC O

O

O

O

(1)

(1)

SOURCE: Carapa procera DC, crabwood (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method Leaf disk choice test

Conc. / Dose 0.1%

Efficacy

Remarks

Feeding ratio = 0.03

Treatment to 7- to 9-day-old larvae prestarved for 24 h. Treatment duration = 3 h. (1)

Value of 0.25 or less considered to be strongly deterrent.

(1) Mikolajczak, K.L., Weisleder, D., Parkanyi, L., and Clardy, J. (1988) J. Nat. Prod., 51, 606.

© 2005 by CRC Press LLC

550

Opender Koul

ISOCEDRELONIC ACID

C26H32O6 (440.51)

M.p. : 295–300° (dec.)

O

[α]D : –50° (CHCl3-EtOH, 1:1)

OH

O COOH OH

(1)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dual choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding inhibition = 42.6%

5 µg/cm2

Feeding inhibition = 46.5%

10 µg/cm2

Feeding inhibition = 59.8%

EC50 = 5.8 µg/cm2

50 µg/cm2

Feeding inhibition = 66.4%

Data calculated from Reference 2.

Treatment to 3rd instar larvae for 24 h. (2)

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumatri, G.N. (1995) J. Chem. Ecol., 21, 1585.

© 2005 by CRC Press LLC

Insect Antifeedants

(±) ISODRIMENIN

551

C15H22O2 (234.34)

M.p. : 131–132° [α]D : +87° (CHCl3)

O O

(2)

(1, 2) SOURCE: Synthetic Also occurs in the bark of Drimys winteri Forst., megellanic bay tree (Magnoliaceae)

(1) (2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk dual choice test

5 mM

Feeding inhibition = 87.0%

1. Treatment to larvae of 90 to 120 mg body weight for a period of 3 h. (1)

2. Pieris brassicae (L.) (Large white butterfly)

Leaf disk dual choice test

5 mM

Feeding inhibition = 88.0%

2. Treatment to 5th stadium larvae of 24to 72-h age for a period of 3 h. (3)

(1) Gols, G.J.Z., van Loon, J.J.A., and Messchendorp, L. (1996) Entomol. Exp. Appl., 79, 69. (2) Appel, H.H., Connolly, J.D., Overton, K.H., and Bond, R.P.M. (1960) J. Chem. Soc., 4685. (3) Messchendorp, L., van Loon, J.J.A., and Gols, G.J.Z. (1996) Entomol. Exp. Appl., 79, 195.

© 2005 by CRC Press LLC

552

Opender Koul

ISOERIOCEPHALIN

C24H30O9 (462.50)

M.p. : 232–234°

O

[α]20 D : –33.1° (CHCl3)

O

OAc

O O AcO

OH

(1, 2)

(1)

SOURCE: Teucrium lanigerum L., forest germander (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Helicoverpa armigera (Hubner) (Gram pod borer)

Test Method Glass fiber disk choice test

Glass fiber disk choice test

Conc. / Dose

Efficacy

Remarks

100 ppm

Feeding inhibition = 38.9%

10 ppm

Feeding inhibition = 33.1%

100 ppm

Feeding inhibition = 24.8%

Treatment to final stadium larvae prestarved for 4 h. Treatment was never longer than 18 h so that never more than 50% of any disk was consumed. (2)

10 ppm

Feeding inhibition = 20.9%

(1) Fernandez-Gadea, F., Rodriguez, B., Savona, G., and Piozzi, F. (1984) Phytochemistry, 23, 1113. (2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry, 28, 1069.

© 2005 by CRC Press LLC

Insect Antifeedants

ISOFRUTICOLONE

553

C22H30O6 (390.48)

Oil [α]D : –87.8° (CHCl3)

O O

O AcO

OH

(1, 2)

(2)

SOURCE: Teucrium fruticans L., bush germander (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Glass fiber disk choice test

Conc. / Dose 100 ppm

Efficacy

Remarks

Feeding inhibition = 53.0%

Treatment to final stadium larvae prestarved for 4 h. Treatment was never longer than 18 h so that never more than 50% of any disk was consumed. (2)

(1) Bruno, M., Ciriminna, R., Piozzi, F., Rosselli, S., and Simmonds, M.S.J. (1999) Phytochemistry, 52, 1055. (2) Savona, G., Passannanti, S., Paternostro, M.P., Piozzi, F., Hanson, J.R., Hitchcock, P.P., and Siverns, M. (1978) J. Chem. Soc. Perkin Trans I, 356.

© 2005 by CRC Press LLC

554

Opender Koul

ISOLACTARORUFIN

C15H22O4 (266.34)

M.p. : 191° [α]20 D : +8.4° (CHCl3)

OH

O

O

OH

(1, 2)

(1)

SOURCE: Lactarius rufus (Scop.) Fr., fungus (Fungi)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 90.3

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient Adults = 56.8 Larvae = 7.7 (inactive)

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 8.7 (inactive)

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Daniewski, W.M., Kocor, M., and Thoren, S. (1976) Heterocycles, 77. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk. Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC

Insect Antifeedants

ISOLONCHOCARPIN

555

C20H18O3 (306.36)

M.p. : 115° [α]24 D : –125° (CHCl3)

O

O

O

(1, 2)

(1)

SOURCE: Lonchocarpus eriocaulinalis M. Mich. (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nut grass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dualchoice test

Glass fiber disk dualchoice test

Efficacy

Remarks

100 ppm

Feeding inhibition = 74.0%

10 ppm

Feeding inhibition = 59.0%

1. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae were prestarved for 4 h. (2)

100 ppm

Feeding inhibition = 88.0%

10 ppm

Feeding inhibition = 87.0%

2. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae were prestarved for 4 h. (2)

(1) Delle Monache, F., Cuca Suarez, L.E., and Bettolo, G.B.M. (1978) Phytochemistry, 17, 1812. (2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

556

Opender Koul

ISOMONTANOLIDE

C22H30O7 (406.47)

M.p. : 174–176° [α]20 D : –25.2° (CHCl3)

OH

OOC OAc O

O

(1, 2)

(1)

SOURCE: Laserpitium siler L., mountain lasser wort (Apiaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

1%

Feeding deterrence coefficient = 77

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

1%

Feeding deterrence coefficient Adults = 171 Larvae = 73

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

1%

Feeding deterrence coefficient = 71

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Holub, M., Motl, O., Samek, Z., and Herout, V. (1972) Collect. Czech. Chem. Commun., 37, 1186. (2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

© 2005 by CRC Press LLC

Insect Antifeedants

ISOPETASIN

557

C20H28O3 (316.44)

M.p. : 99–100° (82–84°) [α]20 D : +31° (CHCl3)

O

O

O

(1)

(1, 2) SOURCE: Petasites kablikianus Tausch ex Bercht. (Asteraceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 29

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 60 Larvae = 99

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 56

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Novotny, L., Kotva, K., Toman, J., and Herout, V. (1972) Phytochemistry, 11, 2795. (2) Nawrot, J., Harmatha, J., and Novotny, L. (1984) Biochem. Syst. Ecol., 12, 99.

© 2005 by CRC Press LLC

558

Opender Koul

ISOPIMARIC ACID

C20H30O2 (302.46)

M.p. : 162–164° [α]24 D : 0° (neat)

CH2

COOH

(1, 2)

(1)

SOURCE: Commercial sample Occurs in Pinus spp.

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatments to 4th or 5th instar larvae for 4 h. (2)

1. Neodiprion dubiosus Schedl. (Brownhead jack pine sawfly)

Pine needle and twig application

7 mg/ml

Feeding inhibition = 70.0%

2. Neodiprion rugifrons Middleton (Redhead jack pine sawfly)

Pine needle and twig application

5.3 mg/ml

Feeding inhibition = 70.0%

3. Neodiprion lecontei (Fitch) (Redhead pine sawfly)

Pine needle and twig application

10.7 mg/ml

Feeding inhibition = 70.0%

(1) Bohlmann, F. and Le Van, N. (1976) Chem. Ber., 109, 1446. (2) Schuh, B.A. and Benjamin, D.M. (1984) J. Econ. Entomol., 77, 802.

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Insect Antifeedants

ISOPIMPINELLIN

559

C13H10O5 (246.22)

M.p. : 147–148° (151°)

OCH3

O

O

O OCH3

(1, 2)

(1)

SOURCE: Oryxa japonica Thunb., Japanese kokusagi (Rutaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk test

Artificial diet assay

Conc. / Dose

Efficacy

Remarks

5 ppm

Feeding inhibition = 50.0%

1. Treatment to 3rd instar larvae. (1)

100 ppm

Feeding inhibition = 100.0%

Treatment to 3rd instar larvae for 90 min. (2)

5 ppm

Feeding inhibition = 50.0%

Treatment to 4th instar larvae prestarved for 48 h. (3)

2. Periplaneta americana (L.) (American cockroach)

Sugar pellet method

0.1 mg/ 1.5 g pellet

Feeding inhibition = 57.0%

2. Treatment to adult cockroaches. (2)

3. Blatella germanica (L.) (German cockroach)

Sugar pellet method

0.1 mg/ 1.5 g pellet

Feeding inhibition = 31.0%

3. Treatment to adult cockroaches. (2)

(1) Yajima, T., Kato, N., and Munakata, K. (1977) Agric. Biol. Chem., 41, 1263. (2) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701. (3) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem., 37, 1435.

© 2005 by CRC Press LLC

560

Opender Koul

ISOPONGAFLAVONE

C21H18O4 (334.37)

O

M.p. : 215–216°

O

OCH3

O

(1, 2)

(1)

SOURCE: Tephrosia elata Deflers, African tephrosia (Fabaceae)

(2)

ACTIVITY PROFILE Test Insect 1. Maruca testulalis (Geyer) (Bean pod borer)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

Feeding inhibition = 86.0% Feeding inhibition = 77.0%

1. Treatment to late 5th instar larvae for 6 h. (2)

Feeding inhibition = 74.0% Feeding inhibition = 54.0%

2. Treatment to 5th instar larvae prestarved for 12 h. Feeding duration = 24 h in the dark. (2)

100 µg

Feeding inhibition = 23.0%

10 µg per 1.8 cm diameter

No inhibition

3. Treatment to mid 6th instar larvae for 2 h. Larvae were prestarved for 2 h. (2)

100 µg 10 µg per 1.8 cm diameter

2. Eldana saccharina Walker (Sugar cane borer)

Leaf disk test

100 µg 10 µg per 1.8 cm diameter

3. Spodoptera exempta (Walker) (Nutgrass armyworm)

Leaf disk test

(1) Chibber, S.S. and Dutt, S.K. (1981) Phytochemistry, 20, 1460. (2) Bentley, M.D., Hassanali, A., Lwandi, W., Njoroge, P.E.W., Sitayo, E.N.O., and Yatagai, M. (1987) Insect Sci. Applic., 8, 85.

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Insect Antifeedants

ISOPROTOSTEMONINE

561

C23H31O6N (417.50)

M.p. : 165–167° [α]D : –23.6° (EtOH)

O N

O

O

O

O OCH3

(1)

(1)

SOURCE: Stemona japonica Miq., Japanese stemona (Stemonaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Glass fiber disk test

200 ppm

Efficacy Feeding inhibition = 33.0%

Remarks Treatment to last instar larvae. (1)

(1) Ye, Y., Qin, G., and Xu, R. (1994) Phytochemistry, 37, 1205.

© 2005 by CRC Press LLC

562

Opender Koul

ISOSILEROLIDE

C22H30O6 (390.48)

M.p. : 141–143° [α]20 D : –138.9° (CHCl3)

OCOCH3

OCO O O

(1, 2)

(1)

SOURCE: Laserpitium siler L., mountain lasser wort (Apiaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

1%

Feeding deterrence coefficient = 52

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

1%

Feeding deterrence coefficient Adults = 136 Larvae = 20

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

1%

Feeding deterrence coefficient = 81

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Holub, M., Budesinsky, M., Smitalova, Z., Saman, D., and Rychlewska, U. (1982) Tetrahedron Lett., 4853. (2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

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Insect Antifeedants

ISOTADEONAL

563

C15H22O2 (234.34)

Oil B.p. : 145–153°/1 mm

CHO

[α]D : –237.4° (EtOH) CHO

(2)

(1) SOURCE: Synthetic Also isolated from Polygonum hydropiper L., water pepper (Polygonaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk dual-choice test

5 mM

Feeding inhibition = 51.0%

1. Treatment to larvae of 90 to 120 mg body weight for a period of 3 h. (1)

2. Pieris brassicae (L.) (Large white butterfly)

Leaf disk dual-choice test

5 mM

Feeding inhibition = 45.0%

2. Treatment to 5th stadium larvae of 24to 72-h-age for a period of 3 h. (3)

(1) Gols, G.J.Z., van Loon, J.J.A., and Messchendorp, L. (1996) Entomol. Exp. Appl., 79, 69. (2) Ohsuka, A. and Matsukawa, A. (1979) Chem. Lett., 63. (3) Messchendorp, L., van Loon, J.J.A., and Gols, G.J.Z. (1996) Entomol. Exp. Appl., 79, 195.

© 2005 by CRC Press LLC

564

Opender Koul

ISOTENULIN

C17H22O5 (306.36)

M.p. : 160–161° [α]D : +6° (EtOH)

H

O

O

O OAc

(1, 2)

(1)

SOURCE: Helenium tenuifolium Nutt., H. arizonicum, H. bigelovii, aster weeds (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Ostrinia nubilalis (Hubner) (European corn borer)

Test Method

Conc. / Dose

Leaf disk choice test

3 µmol/g

Efficacy

Remarks

Feeding inhibition = 65.5%

Treatment to larvae at random. (2)

(1) Herz, W., de Vivar, A.R., Romo, J., and Viswanathan, N. (1963) Tetrahedron, 19, 1359. (2) Arnason, J.T., Isman, M.B., Philogene, B.J.R., and Waddel, T.G. (1987) J. Nat. Prod., 50, 690.

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Insect Antifeedants

ISOTENULIN METHYL IMINE

565

C18H25O4N (319.40)

No physical data given

H

O

N

O OAc

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Ostrinia nubilalis (Hubner) (European corn borer)

Test Method

Conc. / Dose

Leaf disk choice test

3 µmol/g

Efficacy

Remarks

Feeding inhibition = 67.2%

Treatment to larvae at random. (1)

(1) Arnason, J.T., Isman, M.B., Philogene, B.J.R., and Waddel, T.G. (1987) J. Nat. Prod., 50, 690.

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566

Opender Koul

ISOTENULIN OXIDE

C17H24O6 (324.48)

H

No physical data given

H

O O

H

O

O OAc

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Ostrinia nubilalis (Hubner) (European corn borer)

Test Method

Conc. / Dose

Leaf disk choice test

3 µmol/g

Efficacy

Remarks

Feeding inhibition = 65.4%

Treatment to larvae at random. (1)

(1) Arnason, J.T., Isman, M.B., Philogene, B.J.R., and Waddel, T.G. (1987) J. Nat. Prod., 50, 690.

© 2005 by CRC Press LLC

Insect Antifeedants

3-ISOTHUJONE

567

C10H16O (152.24)

B.p. : 85.7–86.2°/17 mm [α]15 D : +72.5° (neat)

O

(1, 2)

(1, 2)

SOURCE: Thuja plicata Donn. ex Don., Western red cedar (Cupressaceae)

(3)

ACTIVITY PROFILE Test Insect Pissodes strobi (Peck) (White pine weevil)

Test Method Agar disk test

Conc. / Dose 75 µg/disk

Efficacy

Remarks

Feeding inhibition = 23.7%

Treatment to adult weevils for 24 h. (3)

LD50 (mice): 442.2 mg/kg (s.c.) (1) Eastman, R.H. and Winn, A.V. (1960) J. Am. Chem. Soc., 82, 5908. (2) Hach, V., Raimondo, R.F., Cartlidge, D.M., and McDonald, E.C. (1970) Tetrahedron Lett., 3175. (3) Alfaro, R.I., Pierce, H.D., Borden, J.H., and Oehlschlager, A.C. (1981) J. Chem. Ecol., 7, 39. (4) Rice, K.C. and Wilson, R.S. (1976) J. Med. Chem., 19, 1054.

© 2005 by CRC Press LLC

(4)

568

Opender Koul

ISOVELLEROL

C15H22O2 (234.35)

Only spectral data given

OHC

HOH2C

(1, 2)

(2)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 176

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 162 Larvae = 161.9

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 200

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Sterner, O., Bergman, R., Kihlberg, J., and Wickberg, B. (1985) J. Nat. Prod., 48, 279. (2) Daniewski, W.M., Gumulka, M., Bloszyk, E., Jacobsson, U., and Norin, T. (1997) Polish J. Chem., 71, 1254.

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Insect Antifeedants

ISOVITEXIN 6″-O-β-D-GLUCOPYRANOSIDE

569

C27H30O15 (594.53)

HO

M.p. : 214–216° O OH

O

OH OH

O

OH

OH

O OH O

HO

OH OH

(1)

(1)

SOURCE: Alliaria petiolata (M. Bieb.) Cavara and Grande, garlic mustard (Cruciferae)

(1)

ACTIVITY PROFILE Test Insect 1. Pieris napi oleracea (L.) (Cabbage butterfly)

Test Method Leaf disk choice test

Conc. / Dose Fraction containing compound used.

Efficacy

Remarks

Feeding deterrence index = 48.4% for a fraction containing the compound. No data given for the pure compound.

1. Treatment given to 4th instar larvae. (1)

(1) Haribal, M. and Renwick, J.A.A. (1998) Phytochemistry, 47, 1237.

© 2005 by CRC Press LLC

570

Opender Koul

IVAIN–1

C28H42O10 (538.63) H

Amorphous [α]D : –8° (CHCl3)

O H O H

H H

HO

H

H COO O

CH2 OCOCH3 OCOCH3

(1)

(1, 2)

SOURCE: Ajuga iva Schreber., bugle ivette (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Leaf disk choice test

1 µg/cm2

Efficacy Feeding ratio = 0.25 ± 0.07

(1) Camps, F., Coll, J., and Cortel, A. (1982) Chem. Lett., 1053. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC

Remarks Treatment to newly ecdysed 5th instar larvae. Feeding ratio of less than 0.5 considered as excellent antifeedant effect. (2)

Insect Antifeedants

IVAIN–2

571

C28H42O9 (522.63) H

M.p. : 158–161° [α]D : –26.8° (CHCl3)

O H O H

H H

H

H

COO O

CH2 OCOCH3 OCOCH3

(1)

(1, 2)

SOURCE: Ajuga iva Schreber., bugle ivette (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

1 µg/cm2

Feeding ratio = 0.14 ± 0.02

0.1 µg/cm2

Feeding ratio = 0.25 ± 0.09

0.01 µg/cm2

Feeding ratio = 0.67 ± 0.10

(1) Camps, F., Coll, J., and Cortel, A. (1982) Chem. Lett., 1053. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC

Remarks Treatment to newly ecdysed 5th instar larvae. Feeding ratio of less than 0.5 considered as excellent antifeedant effect. (2)

572

Opender Koul

IVAIN–3

C30H46O11 (582.69) OC2H5 O

Amorphous [α]D : +31.7° (CHCl3)

H O H

H H

H

HO

COO O

CH2 OCOCH3 OCOCH3

(1, 2)

(1)

SOURCE: Ajuga iva Schreber., bugle ivette (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Leaf disk choice test

1 µg/cm2

Efficacy Feeding ratio = 0.37 ± 0.10

(1) Camps, F., Coll, J., and Cortel, A. (1982) Chem. Lett., 1053. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC

Remarks Treatment to newly ecdysed 5th instar larvae. Feeding ratio of less than 0.5 considered as excellent antifeedant effect. (2)

Insect Antifeedants

IVAIN–4

573

C29H44O10 (552.66) H

Amorphous [α]D : +4.1° (CHCl3)

O H O

H

H H

H

HO

COO O

CH2 OCOCH3 OCOCH3

(1)

(1, 2)

SOURCE: Ajuga iva Schreber., bugle ivette (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Leaf disk choice test

1 µg/cm2

Efficacy Feeding ratio = 0.12 ± 0.04

(1) Camps, F., Coll, J., and Cortel, A. (1982) Chem. Lett., 1053. (2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC

Remarks Treatment to newly ecdysed 5th instar larvae. Feeding ratio of less than 0.5 considered as excellent antifeedant effect. (2)

574

Opender Koul

JAPONINE

C18H17O3N (295.34)

M.p. : 143° (145–146°)

O H3CO

OCH3

N

(1)

(1, 2)

SOURCE: Oryxa japonica Thunb., Japanese kokusagi (Rutaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

300 ppm

Efficacy Feeding inhibition = 50.0%

Remarks Treatment to 3rd instar larvae. (1)

(1) Yajima, T., Kato, N. and Munakata, K. (1977) Agric. Biol. Chem., 41, 1263. (2) Ha-Huy-Ke and Luckner, M. (1970) Phytochemistry, 9, 2199.

© 2005 by CRC Press LLC

Insect Antifeedants

JODRELLIN–A

575

C24H32O8 (448.51)

Oil

OAc OAc O

O

O

O

(1, 2)

(1)

SOURCE: Scutellaria woronowii Juz., skullcap (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Glass fiber disk choice test

Conc. / Dose

Efficacy

Remarks

50 ppm

Feeding inhibition = 100%

25 ppm

Feeding inhibition = 53.0%

Treatment to final stadium larvae prestarved for 4 h. Treatment duration until 50% of either disk was consumed or for 12 h. (2)

(1) Anderson, J.C., Blaney, W.M., Cole, M.D., Fellows, L.L., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J. (1989) Tetrahedron Lett., 30, 4737. (2) Cole, M.D., Anderson, J.C., Blaney, W.M., Fellows, L.E., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J. (1990) Phytochemistry, 29, 1793.

© 2005 by CRC Press LLC

576

Opender Koul

JODRELLIN–B

C26H36O8 (476.57)

Oil [α]20 D : –11.4° (CHCl3)

O OAc

O

O O

O

O

(1)

(1, 2) SOURCE: Scutellaria woronowii Juz., skullcap (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Glass fiber disk choice test

Conc. / Dose

Efficacy

Remarks

50 ppm

Feeding inhibition = 100%

25 ppm

Feeding inhibition = 83.0%

Treatment to final stadium larvae prestarved for 4 h. Treatment duration until 50% of either disk was consumed or for 12 h. (2)

(1) Anderson, J.C., Blaney, W.M., Cole, M.D., Fellows, L.L., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J. (1989) Tetrahedron Lett., 30, 4737. (2) Cole, M.D., Anderson, J.C., Blaney, W.M., Fellows, L.E., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J. (1990) Phytochemistry, 29, 1793.

© 2005 by CRC Press LLC

Insect Antifeedants

JUGLONE

577

C10H6O3 (174.16) M.p. : 155°

O

OH

O

(1, 2)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Peridroma saucia (Hubner) (Variegated cutworm)

LD50 (mice): 2.5 mg/kg (oral)

Test Method

Conc. / Dose

Leaf disk choice test

Efficacy

Remarks

14.25 µg/cm2

Feeding inhibition = 74.5%

Treatment to 5th instar larvae for 5 h. (2)

57.0 µg/cm2

Feeding inhibition = 78.2%

(3)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

578

Opender Koul

KAEMPFEROL-3-O-β-GLUCOPYRANOSIDE

C21H20O11 (448.38)

[α]D : –103°

OH

HO

M.p. : 243–245°

(pyridine:MeOH:H2O) (1 : 1 : 1)

O HO

OH

O O OH

OH

O CH2OH

(1)

(1, 2) SOURCE: Detarium microcarpum Guill. & Perr., African atokolo (Caesalpiniaceae)

(2)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method Paper disk choice test

Conc. / Dose 80 µg/cm2

Efficacy Feeding inhibition index = 5.0

(1) Hasan, C.M., Healey, T.M., and Waterman, P.G. (1982) Phytochemistry, 21, 1365. (2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1101.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index below 20 considered as highly deterrent. (2)

Insect Antifeedants

KALMANOL

579

C20H34O6 (370.48)

H

M.p. : 255–256° (258–261°) [α]25 D : +31° (MeOH)

HO H H

HO

OH OH

OH OH

(1, 2)

(1, 2) SOURCE: Rhododendron molle (B.) G. Don., yellow azalea (Ericaceae) Kalmia angustifoila L., sheep laurel (Ericaceae)

(1) (2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk choice test

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Leaf disk choice test

Test Insect

Efficacy

Remarks

15.0 µg/ 50 mm2

Feeding inhibition = 95.0%

1. Treatment to 4th instar larvae until 95% of control disk was consumed. (1)

12.5 µg/ 50 mm2

Feeding inhibition = 95.0%

2. Treatment to 3rd instar larvae until 95% of control disk was consumed. (1)

(1) Klocke, J.A., Hu, M., Chiu, S., and Kubo, I. (1991) Phytochemistry, 30, 1797. (2) Burke, J.W., Doskotch, R.W., Zhou, C., and Clardy, J. (1989) J. Am. Chem. Soc., 111, 5831.

© 2005 by CRC Press LLC

580

Opender Koul

(–)- KAURAN-16α-OL

C20H34O (290.49)

M.p. : 210–211°

OH

H

(1, 2)

(1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae)

(2)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method Paper disk choice test

Conc. / Dose

Efficacy

5000 ppm

Feeding inhibition index = 0.0

2500 ppm

Feeding inhibition index = 14.4

(1) Bohlmann, F. and le Van, N. (1977) Phytochemistry, 16, 487. (2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index below 20 considered as highly deterrent. (2)

Insect Antifeedants

(–)-KAURAN-16α-19-DIOL

581

C20H34O2 (306.49)

M.p. : 200–201° [α]22 D : –40.5° (EtOH)

OH

H CH2OH

(1)

(1, 2) SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae)

(2)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method Paper disk choice test

Conc. / Dose 5000 ppm

Efficacy Feeding inhibition index = 18.0

(1) Henrick, C.A. and Jefferies, P.R. (1964) Aust. J. Chem., 17, 915. (2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index below 20 considered as highly deterrent. (2)

582

Opender Koul

KAUR-16-EN-19-OIC ACID

C20H30O2 (302.46)

M.p. : 179–181° [α]D : –110° (CHCl3)

CH2

H COOH

(1)

(1, 2) SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) Lasianthaea sp. (Asteraceae)

(2) (1)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe (Subterranean termite)

Test Method Paper disk choice test

Conc. / Dose

Efficacy

2500 ppm

Feeding inhibition index = 7.78

1000 ppm

Feeding inhibition index = 5.4

(1) Wiemer, D.F. (1985) Rev. Latinoamer. Quim., 16, 98. (2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index below 20 considered as highly deterrent. (2)

Insect Antifeedants

KERLINIC ACID

583

C20H28O4 (332.44)

M.p. : 183–185° [α]22 D : –236.8° (CHCl3)

H O

OH HOOC

(1, 2)

(1)

SOURCE: Salvia keerlii Benth., sage plant (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method Leaf disk nochoice test

Conc. / Dose

Efficacy

Remarks

2 ppm

Feeding inhibition = 75.0%

50 ppm

Feeding inhibition = 75.0%

Treatment to 3rd instar larvae prestarved for 4 h. Treatment duration = 24 h. (2)

100 ppm

Feeding inhibition = 100%

Data calculated from Reference 2.

(1) Lidia Rodriguez-Ilahn, L. (1987) Can. J. Chem., 65, 2687. (2) Taboada, J., Guerrero, C., Camino, L.M., and Aldama, L. L. (1996) Rev. Latinoamer. Quim., 24, 33.

© 2005 by CRC Press LLC

584

Opender Koul

13-KETO-8 (14)-PODOCARPEN-18-OIC ACID

C17H24O3 (276.38)

Only spectral data given

O

COOH

(1)

(2)

SOURCE: Pinus banksiana Lamb., jack pine (Pinaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Neodiprion rugifrons Middleton (Pine sawfly)

2. Neodiprion swainei Middleton (Pine sawfly)

Test Method Spray

Spray

Conc. / Dose

Efficacy

Remarks

10 mg/ml

Feeding inhibition = 100%

1 mg/ml

Feeding inhibition = 100%

1. Treatment to 3rd instar larvae. Sprays applied on both larvae as well as host branches. (1)

5 mg/ml

Feeding inhibition = 85.8%

1 mg/ml

Feeding inhibition = 75.0%

2. Treatment to 3rd instar larvae. Sprays applied on both larvae as well as host branches. (1)

(1) Ikeda, T., Matsumura, F., and Benjamin, D.M. (1977) J. Chem. Ecol., 3, 677. (2) Cheung, H.T.A., Miyase, T., Lenguyeu, M.P., and Small, M.A. (1993) Tetrahedron, 49, 7903

© 2005 by CRC Press LLC

Insect Antifeedants

KHAYANOLIDE-A (1-O-ACETYL)

585

C29H35O11 (559.22) O

Amorphous powder [α]D : +59° (MeOH)

O CH3OOC

H

HO

O

OAc

O

O OH

(1)

(1)

SOURCE: Khaya senegalensis (Desv.) A. Juss., dry-zone mahogany (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

100 ppm (2 µg/cm2)

Feeding inhibition = 50%

Treatment to 3rd instar larvae until the larvae had eaten approximately 50% of one of the disks. (1)

(1) Nakatani, M., Abdelgaleil, S.A.M., Kurawaki, J., Okamura, H., Iwagawa, T., and Doe, M. (2001) J. Nat. Prod., 64, 1261.

© 2005 by CRC Press LLC

586

Opender Koul

KHAYANOLIDE–E

C29H35O11 (559.22) O

Amorphous powder

[α]D : +21° (MeOH)

CH3OOC

O

OH

H

HO

O

OAc O

O

(1)

(1)

SOURCE: Khaya senegalensis (Desv.) A. Juss., dry-zone mahogany (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

100 ppm (2 µg/cm2)

Feeding inhibition = 50%

Treatment to 3rd instar larvae until the larvae had eaten approximately 50% of one of the disks. (1)

(1) Nakatani, M., Abdelgaleil, S.A.M., Kassem, S.M.I., Takezaki, K., Okamura, H., Iwagawa, T., and Doe, M. (2002) J. Nat. Prod., 65, 1219.

© 2005 by CRC Press LLC

Insect Antifeedants

KHAYANONE

587

C27H35O9 (503.23) M.p. : 170–171°C

O

[α]D : +2.6° (MeOH)

CH3OOC

O

OH

H

HO

O

O H

O

(1)

(1) SOURCE: Khaya senegalensis (Desv.) A. Juss., dry-zone mahogany (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

300 ppm (6 µg/cm2)

Feeding inhibition = 50%

Treatment to 3rd instar larvae until the larvae had eaten approximately 50% of one of the disks. (1)

(1) Nakatani, M., Abdelgaleil, S.A.M., Kurawaki, J., Okamura, H., Iwagawa, T., and Doe, M. (2001) J. Nat. Prod., 64, 1261.

© 2005 by CRC Press LLC

588

Opender Koul

KHELLIN

C14H12O5 (260.24)

B.p. : 180–200°/0.05 mm

O

OCH3

O

M.p. : 150.3° 154–155° (dimorph.)

O OCH3

(1, 2)

(1)

SOURCE: Ammi visnaga (L.) Lamark., visnaga (Apiaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

2. Blatella germanica (L.) (German cockroach)

Test Method

Conc. / Dose

Efficacy

Remarks

Leaf disk choice test

1000 ppm

Feeding inhibition ratio = 20%

1. Treatment to 3rd instar larvae. Inhibition ratio of less than 20% is highly deterrent value. (2)

Artificial diet feeding

107.9 ppm

Feeding inhibition = 50.0%

Treatment to 4th instar larvae prestarved for 4 h. Treatment duration = 48 h. Concentration = FI50 (3)

Sugar pellet method

0.1 mg/ 1.5 g pellet

Feeding inhibition = 87.0%

2. Treatment to adults. (2)

3. Periplaneta americana (L.) (American cockroach)

Sugar pellet method

0.1 mg/ 1.5 g pellet

Feeding inhibition = 33.0%

3. Treatment to adults. (2)

4. Stylopyga rhambifolia (Cockroach)

Sugar pellet method

0.1 mg/ 1.5 g pellet

Feeding inhibition = 34.0%

4. Treatment to adults. (2)

LD50 (rats): 69 mg/kg (oral)

(4)

(1) Spath, E. and Gruber, W. (1938) Ber., 71, 106. (2) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701. (3) Luthria, D.L., Ramakrishnan, V., and Banerji, A. (1993) J. Nat. Prod., 56, 671. (4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

KHELLINOL DIETHYL ETHER

589

C16H16O5 (288.22)

Only spectral data given

OC2H5 O

O

O

OC2H5

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Artificial diet assay

Conc. / Dose 28.1 ppm

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 4th instar larvae prestarved for 4 h. Treatment duration = 48 h. Concentration = FI50 (1)

(1) Luthria, D.L., Ramakrishnan, V., and Banerji, A. (1993) J. Nat. Prod., 56, 671.

© 2005 by CRC Press LLC

590

Opender Koul

KHELLINOL ETHYL ETHER

C15H14O5 (274.21)

Only spectral data given

OCH3 O

O

O

OC2H5

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Artificial diet assay

Conc. / Dose 49.8 ppm

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 4th instar larvae prestarved for 4 h. Treatment duration = 48 h. Concentration = FI50 (1)

(1) Luthria, D.L., Ramakrishnan, V., and Banerji, A. (1993) J. Nat. Prod., 56, 671.

© 2005 by CRC Press LLC

Insect Antifeedants

KIEVITONE

591

C20H20O6 (356.37)

HO

Only spectral data given

O

OH

O

OH

HO

(1, 2)

(1)

SOURCE: Phaseolus vulgaris L., french bean (Fabaceae) (virus infected)

(2)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Artificial diet assay

Conc. / Dose 120 µg/g

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 24 h pre-starved 3 rd instar larvae. Concentration = FI50 (2)

(1) Burden, R.S., Bailey, J.A., and Dawson, G.W. (1972) Tetrahedron Lett., 4175. (2) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC

592

Opender Koul

KLAINEANONE

C20H28O6 (364.44)

M.p. : 253–258° [α]22 D : –52° (Pyridine)

OH HO HO O H O

O

H

(1, 2)

(1)

SOURCE: Hannoa klaineana Pierre et Engler., African quassia (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Leaf disk test

12 µg/cm2

6 µg/cm2

Efficacy Feeding inhibition = 60–90% after 2 days and 0–30% after 6 days of treatment.

Remarks Treatment to 3rd instar larvae. (2)

Feeding inhibition = 60–90% after 2 days and 0–30% after 6 days of treatment.

(1) Polonsky, J. and Zylber, N.B. (1965) Bull. Soc. Chim. Fr., 2793. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

Insect Antifeedants

KOKUSAGINE

593

C13H9O4N (243.22)

M.p. : 202–203°

OCH3

N

O

O

O

(1)

(1)

SOURCE: Oryxa japonica Thunb., Japanese kokusagi (Rutaceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk choice test

2. Blatella germanica (L.) (German cockroach)

Sugar pellet method

Test Insect

Efficacy

Remarks

100 ppm

Feeding inhibition = 50.0%

1. Treatment to 3rd instar larvae. (1)

0.1 mg/ 1.5 g pellet

Feeding inhibition = 91.0%

2. Treatment to adults. (2)

3. Periplaneta americana (L.) (American cockroach)

Sugar pellet method

0.1 mg/ 1.5 g pellet

Feeding inhibition = 70.0%

3. Treatment to adults. (2)

4. Stylopyga rhambifolia (Cockroach)

Sugar pellet method

0.1 mg/ 1.5 g pellet

Feeding inhibition = 91.0%

4. Treatment to adults. (2)

(1) Yajima, T., Kato, N., and Munakata, K. (1977) Agric. Biol. Chem., 41, 1263. (2) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC

594

Opender Koul

KOLAVENOL

C20H34O (290.49)

Oil [α]D : –45.7° (CHCl3)

OH

(1)

(1)

SOURCE: Melampodium divericatum Rolfe. (Asteraceae) Also occurs in Hardwickia pinnata Roxb., anjan (Fabaceae); Solidago elongata, goldenrod (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Atta cephalotes (L.) (Leaf cutter ant)

Test Method Rye flake forced choice test

Conc. / Dose 4 µg/flake

Efficacy

Remarks

Feeding inhibition = 32%

Treatment to adult workers. Data calculated from Reference 2. (2)

(1) Hubert, T.D. and Wiemer, D.F. (1985) Phytochemistry, 24, 1197. (2) Wiemer, D.F. (1985) Rev. Latinoamer. Quim., 16, 98.

© 2005 by CRC Press LLC

Insect Antifeedants

LACTARORUFIN–A

595

C15H22O4 (266.34)

M.p. : 156–158° [α]20 D : +7° (CHCl3)

O HO OH O H

(1, 2, 3)

(1, 2)

SOURCE: Lactarius rufus (Scop.) Fr., fungus (Fungi)

(4)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 88.6

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient Adults = 163.8 Larvae = 144.9

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 153.6

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (4)

(1) Daniewski, W.M. and Kocor, M. (1970) Bull. Acad. Pol. Sci. Ser. Sci. Chim., 18, 585. (2) Daniewski, W.M. and Kocor, M. (1971) Bull. Acad. Pol. Sci. Ser. Sci. Chim., 19, 553. (3) Baranowska, E. and Daniewski, W.M. (1972) Bull. Acad. Pol. Sci. Ser. Sci. Chim., 20, 313. (4) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk. Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC

596

Opender Koul

LACTARORUFIN–B

C15H22O5 (282.34)

M.p. : 213° [α]20 D : +24° (CHCl3)

HOH2C O HO OH O

(1, 2)

(1, 2) SOURCE: Lactarius rufus (Scop.) Fr., fungus (Fungi)

(3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 37.2

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient Adults = 133.3 Larvae = 67.9

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 92.6

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (4)

(1) Daniewski, W.M. and Kocor, M. (1970) Bull. Acad. Pol. Sci. Ser. Sci. Chim., 18, 585. (2) Daniewski, W.M., Kocor, M., and Krol, J. (1976) Rocz. Chem. Ann. Soc. Chem. Pol., 50, 2095. (3) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk. Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC

Insect Antifeedants

LACTUPICRIN

597

C23H22O7 (410.42)

M.p. : 132–178° [α]D : +73° (pyridine)

O

OOC

CH2OH

OH

CH2

O

O

(1, 2)

(1)

SOURCE: Cichorium intybus L., chicory (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Schistocerca gregaria (Forsk.) (Desert locust)

Test Method Glass fiber disk test

Conc. / Dose

Efficacy

Remarks

1.0%

Feeding deterrence = 89.0%

0.68%

Feeding deterrence = 83.5%

Treatment given to 2to 3-day-old adults of either sex (1:1). (2)

0.21%

Feeding deterrence = 77.5%

0.11%

Feeding deterrence = 54.5%

(on dry weight basis)

(1) Pyrek, J.S. (1977) Roczniki Chemii., 51, 2165. (2) Rees, S.B. and Harborne, J.B. (1985) Phytochemistry, 24, 2225.

© 2005 by CRC Press LLC

598

Opender Koul

LAMBERTIANIC ACID

C20H28O3 (316.44)

M.p. : 126.5–127.5° [α]22 D : +55° (EtOH)

O CH2

COOH

(1, 2)

(1)

SOURCE: Osmunda asiatica (Fern.) Fraser-Jenkins, fern (Osmundaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 0.006%

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment given to aphids at random. (2)

(1) Dauben, W.G. and German, V.F. (1969) Tetrahedron, 22, 679. (2) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

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Insect Antifeedants

LASEROLIDE

599

C22H30O6 (390.48) M.p. : 140–141° [α]20 D : –234° OAc

O

O O O

(1)

(1, 2) SOURCE: Laser trilobum (L.) Borkh., gladich (Apiaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

1%

Feeding deterrence coefficient = 76

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

1%

Feeding deterrence coefficient Adults = 117 Larvae = 71

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

1%

Feeding deterrence coefficient = 66

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Holub, M., Samek, Z., Popa, D.P., Herout, V., and Sorm, F. (1970) Collect. Czech. Chem. Commun., 35, 284. (2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

© 2005 by CRC Press LLC

600

Opender Koul

LASIDIOL ANGELATE

C20H32O3 (320.47)

Oil

OH

O

O

(1)

(1)

SOURCE: Lasianthaea fruticosa (L.) Becker (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Atta cephalotes (L.) (Leaf cutter ants)

Efficacy Feeding deterrence

Remarks Repels leaf cutter ants apparently due to antifeedant effect. No quantitative data given. (1)

(1) Wiemer, D.F. and Ales, D.C. (1981) J. Org. Chem., 46, 5449.

© 2005 by CRC Press LLC

Insect Antifeedants

LASIOCARPINE

601

C21H33O7N (411.49)

[α]20 D : –4° (EtOH)

OH

C

M.p. : 95° (95.5–97°)

H HO

CH3

C OCH3

C

C

O

C

C

O

O

H O

CH2

N

(1, 2)

(1)

SOURCE: Heliotropium arbainense Fres., heliotrop (Boraginaceae)

(2)

ACTIVITY PROFILE Test Insect Choristoneura fumiferana (Clemens) (Spruce budworm)

Test Method Paper penicillin disk assay

Conc. / Dose 1.2 × 103 M

Efficacy Feeding deterrence = 88.0%

Remarks Treatment to 6th instar larvae.

LD50 (rats): 72 mg/kg (i.p.) (1) Menshikov, G. (1932) Ber., 65, 974. (2) Bentley, M.D., Leonard, D.E., Stoddard, W.F., and Zalkow, L.H. (1984) An. Entomol. Soc. Am., 77, 393. (3) Cordell, G.A. (1981) Introduction to Alkaloids, John Wiley & Sons, New York, p. 134.

© 2005 by CRC Press LLC

(2)

(3)

602

Opender Koul

LAURIC ACID (dodecanoic acid)

C12H24O2 (200.32)

M.p. : 44° B.p. : 225°/100 mm nD82

: 1.4183

COOH

(1, 2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk assay

Efficacy

Remarks

0.25 mg/cm2

Feeding deterrence = 49.4%

0.05 mg/cm2

Feeding deterrence = 16.0%

Treatment to larvae of 10–13 mg body weight for 1 week. (2)

LD50 (mice): 131.0 + 5.7 mg/kg (i.v.) (1) Dale, A.P. and Meara, M.L. (1955) J. Sci. Food Agric., 6, 162. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. (3) Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

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(3)

Insect Antifeedants

LEDOL

603

C15H26O (222.37)

M.p. : 105° B.p. : 282–283° [α]D : +8° (EtOH)

OH

(1, 2)

(1, 2)

SOURCE: Entandrophragma cylindricum (Sprague) Sprague., penkua (Meliaceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 125.2

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 159.3 Larvae = 104.6

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence Coefficient = 178.3

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) El-Seedi, H., Ghia, F., and Torssell, K.B.G. (1994) Phytochemistry, 35, 1495. (2) Daniewski, W.M., Gumulka, M., Ancezewski, W., Truszewska, D., Bloszyk, E., and Drozdz, B. (1996) Polish J. Chem., 70, 1265.

© 2005 by CRC Press LLC

604

Opender Koul

LEPTINE–III Not well characterized

Unknown structure Sugar residual not identified

SOURCE: Commercial material

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Sensillum response recording

Conc. / Dose

Efficacy

Remarks

0.02% wet weight

Feeding deterrence = 50.0%

Treatment to adult beetles. (1)

(1) Mitchel, B.K. and Harrison, G.D. (1985) J. Chem. Ecol., 11, 73.

© 2005 by CRC Press LLC

Insect Antifeedants

LEVOPIMARIC ACID

605

C20H30O2 (302.46)

M.p. : 150–152° [α]24 D : –276° (EtOH)

COOH

(1, 2)

(1, 2)

SOURCE: Pinus banksiana Lamb., jack pine (Pinaceae)

(3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Neodiprion dubiosus Schedl. (Brownhead jack pine sawfly)

Pine needle and twig application

0.5 mg/ml 1.0 mg/ml

Feeding inhibition = 71.0% Feeding inhibition = 83.0%

1. Treatment to 3rd or 4th instar larvae for 4 h. (3)

2. Neodiprion rugifrons Middleton (Redhead jack pine sawfly)

Pine needle and twig application

0.5 mg/ml

Feeding inhibition = 45.0% Feeding inhibition = 67.0%

2. Treatment to 3rd or 4th instar larvae for 4 h. (3)

3. Neodiprion lecontei (Fitch) (Redhead pine sawfly)

Pine needle and twig application

11.3 mg/ml

Feeding inhibition = 70.0%

3. Treatment to 3rd or 4th instar larvae for 4 h. (4)

4. Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

0.03%

Feeding inhibition = 50.0%

4. Treatment to aphids at random.

(1) (2) (3) (4) (5)

1.0 mg/ml

Harris, G.C. and Sanderson, T.F. (1948) J. Am. Chem. Soc., 70, 334. Schuller, W.H. and Lawrence, R.V. (1961) J. Am. Chem. Soc., 83, 2563. Schuh, B.A. and Benjamin, D.M. (1984) J. Chem. Ecol., 10, 1071. Schuh, B.A. and Benjamin, D.M. (1984) J. Econ. Entomol., 77, 802. Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

© 2005 by CRC Press LLC

(5)

606

Opender Koul

LICOISOFLAVONE–A

C20H18O6 (354.36)

HO

M.p. : 111–114°

O

OH

O

HO

OH

(1, 2)

(1, 2)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Costelytra zealandica (White) (Scarab beetle)

Artificial diet feeding

2. Heteronychus arator (Fab.) (Pasture scarab beetle)

Artificial diet feeding

Test Insect

Efficacy

Remarks

200 µg/ml

Feeding inhibition = 31.0%

1. Treatment to 24-h starved 3rd instar larvae for 24 h. (3)

200 µg/ml

Feeding inhibition = 33.0%

2. Treatment to 24-h starved 3rd instar larvae for 24 h. (2)

(1) Kinoshita, T., Saitoh, T., and Shibata, S. (1978) Chem. Pharm. Bull., 26, 141. (2) Lane, G.A., Sutherland, O.R.W., and Skip, R.A. (1987) J. Chem. Ecol., 13, 771. (3) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnel, D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC

Insect Antifeedants

LICOISOFLAVONE–B

607

C20H16O6 (352.34)

HO

O

OH

M.p. : 185–186°

OH

O

O

(1, 3)

(1, 3)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Costelytra zealandica (White) (Scarab beetle)

Artificial diet feeding

1.2 µg/g

Feeding inhibition = 50.0%

1. Treatment to 24-h starved 3rd instar larvae for 24 h. (3)

2. Heteronychus arator (Fab.) (Pasture scarab beetle)

Artificial diet feeding

200 µg/ml

Feeding inhibition = 50.0%

2. Treatment to 24-h starved 3rd instar larvae for 24 h. (2)

(1) Ingham, J.L., Tahara, S., and Harborne, J.B. (1983) Z. Naturforsch, 38C, 194. (2) Lane, G.A., Sutherland, O.R.W., and Skip, R.A. (1987) J. Chem. Ecol., 13, 771. (3) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnel, D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC

608

Opender Koul

LIMONILIC ACID

C26H30O9 (486.52) O

M.p. : 290–292° [α]D : +104° (acetone)

O OH

O

O

O

O O O

(1, 2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk test

Conc. / Dose

Efficacy

100 µg/cm2

Feeding deterrence = 77.3%

31.7 µg/cm2

Feeding deterrence = 73.3%

10.0 µg/cm2

Feeding deterrence = 44.9%

3.17 µg/cm2

Feeding deterrence = 4.7%

Remarks Treatment to 4th instar larvae for 6–8 h. (2) FI50 = 18.28 µg/cm2 Calculated from Reference 2.

(1) Barton, D.H.R., Pradhan, S.K., Sternhell, S., and Templeton, J.F. (1961) J. Chem. Soc., 255. (2) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.

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Insect Antifeedants

LIMONIN

609

C26H30O8 (470.52) M.p. : 298°

O

[α]D : –125° (Acetone) O

O

O

O

O

O O

(1, 2)

(1)

SOURCE: Many citrus species Citrus paradis Macfad., grape fruit (Rutaceae)

(2) (3)

ACTIVITY PROFILE Test Insect 1. Eldana saccharina Walker (Sugarcane borer)

2. Maruca testulalis (Geyer) (Bean pod borer)

Test Method Leaf disk test

Leaf disk test

Conc. / Dose

Efficacy

Remarks

100 µg/disk

Feeding deterrence = 61.0 ± 10%

10 µg/disk

Feeding deterrence = 42.0 ± 14%

1. Treatment to 12-h pre-starved late 5th instar larvae. (2)

100 µg/disk

Feeding deterrence = 75.0 ± 9%

10 µg/disk

Feeding deterrence = 58.0 ± 21%

2. Treatment to 12-h pre-starved late 5th instar larvae. (2)

3. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk spray test

0.5%

Feeding inhibition ratio = + 4

3. Treatment to 3rd and 4th instar larvae. (3) EC50 = 0.78 µg/cm2 calculated from Reference 4. (4)

4. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk test

100 µg/cm2

Feeding deterrence = 67.4%

4. Treatment to 4th instar larvae. (5)

31.7 µg/cm2

Feeding deterrence = 64.4%

47,791 ppm

Feeding deterrence = 50.0%

5. Reticulitermes speratus Kolbe (Subterranean termite)

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Paper disk no-choice test

5. Treatment to 3rd instar larvae based on size. Treatment duration = 25 days. Concentration = EC50value. (6)

610 6. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

7. Heliothis zea (Boddie) (Corn earworm)

Opender Koul Leaf disk test

6.12 µg/disk

Feeding inhibition = 95.0%

Glass fiber disk test

100 ppm

Feeding inhibition = 87.0%

Leaf disk test

60.8 µg/disk

Feeding inhibition = 95.0%

6. Treatment to larvae. (7) Treatment to 24-to 36-h-old final stadium larvae prestarved for 2 h for 8 h. (9) 7. Treatment to larvae. (7)

8. Hylobius pales (Herbst.) (Pales weevil)

Twig dip treatment, choice test

10%

Feeding inhibition = 59.2%

8. Treatment to 22–65 mg body weight weevils for 24 h. (8) Data calculated from Reference 8.

(1) Melera, A., Schaffner, K., Arigoni, D., and Jeger, O. (1957) Helv. Chim. Acta, 40, 1420. (2) Hassanali, A., Bentley, M.D., Sitayo, E.N.O., Njoroge, P.E.W., and Yatagai, M. (1986) Insect Sci. Applic., 7, 495. (3) Koul, O. (1983) Z. Angew, Entomol., 95, 166. (4) Govindachari, T.R., Narasimhan, N.S., Suresg, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari, G.N. (1995) J. Chem. Ecol., 21, 1585. (5) Alford, A.R., Cullen, J.A., Storch, R.H., and Bentley, M.D. (1987) J. Econ. Entomol., 80, 575. (6) Serit, M., Ishida, M., Hagiwara, N., Kim, M., Yamamoto, T., and Takahashi, S. (1992) J. Chem Ecol., 18, 593. (7) Kubo, I. and Klocke, J.A. (1981) Colloques Inst. Nat. Recherches Agric., 7, 117. (8) Salom, S.M., Carlson, J.A., Ang, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407. (9) Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) J. Agric. Food Chem., 50, 6766.

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Insect Antifeedants

LIMONIN DIOSPHENOL (Evodol)

611

C26H28O9 (484.50) O

M.p. : 273–278° (280–285°) [α]24 D : –193° (Acetone)

O

O

O

O O

O O OH

(1)

(1, 2) SOURCE: Evodia glauca Miq., Summer fir (Rutaceae) Synthetic

(2) (3)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk test

1000 ppm

Efficacy Feeding deterrence = 100%

Remarks 1. Treatment to larvae at random. (2)

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk test

100 µg/cm2

Feeding deterrence = 93.8%

31.7 µg/cm2

Feeding deterrence = 81.4%

10.0 µg/cm2

Feeding deterrence = 56.6%

3.17 µg/cm2

Feeding deterrence = 6.2%

2. Treatment to 4th instar larvae for 6 to 8 h. (3) FI50 = 11.7 µg/cm2 Calculated from Reference 3.

(1) Dreyer, D.L. (1967) J. Org. Chem., 32, 3442. (2) Nakatani, M., Takao, H., Iwashita, T., Naoki, H., and Hase, T. (1987) Bull. Chem. Soc. Jpn., 60, 2503. (3) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.

© 2005 by CRC Press LLC

612

Opender Koul

LIMONIN-7-METHOXIME

C27H33O8N (499.56) O

Amorphous solid [α]25 D : –134.65° (CHCl3)

O

O

O

O

O

O

N OCH3

(1)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J. E. Smith) (Fall armyworm)

Test Method

Conc. / Dose

Glass-fiber disk test

100 ppm

Efficacy

Remarks

Feeding deterrence = 76.0%

Treatment for 8 h to 24- to 36-h-old final stadium larvae prestarved for 2 h. (1)

(1) Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) J. Agric. Food Chem., 50, 6766.

© 2005 by CRC Press LLC

Insect Antifeedants

LIMONIN-7-OXIME

613

C26H31O8N (485.53)

Amorphous solid

O

[α]25 D : –159.46° (CHCl3) O

O

O

O

O

O

N OH

(1)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J. E. Smith) (Fall armyworm)

Test Method

Conc. / Dose

Glass-fiber disk test

100 ppm

Efficacy

Remarks

Feeding deterrence = 68.0%

Treatment for 8 h to 24- to 36-h-old final stadium larvae prestarved for 2 h. (1)

(1) Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) J. Agric. Food Chem., 50, 6766.

© 2005 by CRC Press LLC

614

Opender Koul

LIMONOL

C26H32O8 (472.53)

[α]25 D : –57.28° (CHCl3)

O

O

O

O

O O

O OH

(1, 2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera frugiperda (J. E. Smith) (Fall armyworm)

Glass-fiber disk test

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk test

Test Insect

Efficacy

Remarks

100 ppm

Feeding deterrence = 68.0%

1. Treatment for 8 h to 24- to 36-h-old final stadium larvae pre-starved for 2 h. (1)

100 µg/cm2

Feeding deterrence = 78.7%

31.7 µg/cm2

Feeding deterrence = 48.4%

2. Treatment to 4th instar larvae for 6 to 8 h. (2)

10.0 µg/cm2

Feeding deterrence = 39.4%

3.17 µg/cm2

Feeding deterrence = 11.9%

FI50 = 24.28 µg/cm2 Calculated from Reference 2.

(1) Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) J. Agric. Food Chem., 50, 6766. (2) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.

© 2005 by CRC Press LLC

Insect Antifeedants

LINIFOLIN–A

615

C17H20O5 (304.34)

M.p. : 195–198° [α]26 D : +33° (CHCl3)

O

O

O OAc CH2

(1, 2)

(1)

SOURCE: Helenium aromaticum (Hook) Bailey, aromatic aster weed (Asteraceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient Adults = 101–150 Larvae = 51–100

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 151–200

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Herz, W. (1962) J. Org. Chem., 27, 4043. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace.Nauk. Inst. Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC

616

Opender Koul

LINOLEIC ACID

C18H32O2 (280.45)

B.p. : 230°/16 mm n20 D

: 1.4699

COOH

(1, 2)

(1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae) Hibiscus syriacus L., rose-of-sharon (Malvaceae)

(2) (3)

ACTIVITY PROFILE Test Insect 1. Incisitermes minor (Hagen) (Western drywood termite)

2. Anthonomus grandis Bohem. (Boll weevil)

Test Method

Conc. / Dose

Paper towel disk assay

Plate bioassay

Efficacy

Remarks

0.25 mg/cm2

Feeding deterrence = 43.4%

0.05 mg/cm2

Feeding deterrence = 12.4%

1. Treatment to larvae of 10–13 mg body weight for one week. (2) Data calculated from Reference 2.

100 µg/ feeding site

Feeding 25% of controls after 3 h and 35% after 6 h in males and 21% and 34% in females, respectively.

(1) Swern, D. and Parker, W.E. (1953) J. Am. Oil Chem. Soc., 30, 5. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. (3) Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) J. Chem. Ecol.., 13, 1087.

© 2005 by CRC Press LLC

2. Treatment to adult weevils. (3)

Insect Antifeedants

LINOLENIC ACID

617

C18H30O2 (278.44)

M.p. : –11.3° B.p. : 230–232°/1 mm

COOH

(1, 2)

(1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae) Hibiscus syriacus L., rose-of-sharon (Malvaceae)

(2) (3)

ACTIVITY PROFILE Test Insect 1. Incisitermes minor (Hagen) (Western drywood termite)

2. Anthonomus grandis Bohem. (Boll weevil)

Test Method

Conc. / Dose

Paper towel disk assay

Plate bioassay

Efficacy

Remarks

0.25 mg/cm2

Feeding deterrence = 45.1%

0.05 mg/cm2

Feeding deterrence = 22.0%

1. Treatment to larvae of 10–13 mg body weight for one week. (2) Data calculated from Reference 2.

100 µg/ feeding site

Feeding 33% of controls after 2 h and 34% after 6 h in males and 23% and 21% in females, respectively.

(1) Swern, D. and Parker, W.E. (1953) J. Am. Oil Chem. Soc., 30, 5. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. (3) Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) J. Chem. Ecol.., 13, 1087.

© 2005 by CRC Press LLC

2. Treatment to adult weevils. (3)

618

Opender Koul

LOBATIN–A

C22H30O8 (422.47)

M.p. : 154–155° [α]20 D : –304° (CHCl3)

O

O O

O OH

O CH O O

(1, 2)

(2)

SOURCE: Neurolaena lobata (L.) R. Br., golden rod (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk nochoice test

70 µg/1.5 cm2

Efficacy

Remarks

Feeding deterrence = 52.2%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 30 min. (1)

(1) Passreiter, C.M. and Isman, M.B. (1997) Biochem. Syst. Ecol., 25, 371. (2) Passreiter, C.M., Wendisch, D., and Gondol, D. (1995) Phytochemistry, 39, 133.

© 2005 by CRC Press LLC

Insect Antifeedants

LOBATIN–B

619

C20H24O7 (376.40)

Oil [α]20 D : –11.5° (CHCl3)

OH

O

O O O O

CH2

O

(1, 2)

(3)

SOURCE: Neurolaena lobata (L.) R. Br., golden rod (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk nochoice test

70 µg/1.5 cm2

Efficacy

Remarks

Feeding deterrence = 41.3%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 30 min. (1)

(1) Passreiter, C.M. and Isman, M.B. (1997) Biochem. Syst. Ecol., 25, 371. (2) Passreiter, C.M., Wendisch, D., and Gondol, D. (1995) Phytochemistry, 39, 133. (3) Borges-del-Castillo, J., Manresa-Ferrero, T., Rodriguez-Luis, F., Vazquez-Bueno, P., Gupta, M.P., and JosephNathan, P. (1987) J. Nat. Prod., 45, 762.

© 2005 by CRC Press LLC

620

Opender Koul

LONCHOCARPIN

C20H18O3 (306.36)

O

M.p. : 108°

OH

O

(1, 2)

(1)

SOURCE: Lonchocarpus neuroscapha Benth., Coroa piaca (Fabaceae)

(2)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nutgrass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dualchoice test

Glass fiber disk dualchoice test

Efficacy

Remarks

100 ppm

Feeding deterrence = 55.0%

10 ppm

Feeding deterrence = 39.0%

1. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (2)

100 ppm

Feeding deterrence = 43.0%

2. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (2)

(1) Monache, F.D., Suarez, L.E.C., and Bettolo, G.B.M. (1978) Phytochemistry, 17, 1812. (2) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

Insect Antifeedants

LUPANINE

621

C15H24ON2 (248.37)

M.p. : 40° B.p. : 185–186°/0.8 mm

H

[α]D : +61.4° (Me2CO) N

N H O

(1, 2)

(1)

SOURCE: Lupinus polyphyllus Lindl., lupine (Fabaceae)

(2)

ACTIVITY PROFILE Test Insect Choristoneura fumiferana (Clemens) (Spruce budworm)

LD50 (rats): 1440 mg/kg (oral)

Test Method Paper penicillin disk assay

Conc. / Dose 2 × 103 M

Efficacy Feeding deterrence = 25.0%

Remarks Treatment to 6th instar larvae. (2)

(3)

(1) Clemo, G.R., Raper, R., and Seaton, J.C. (1956) J. Chem. Soc., 3390. (2) Bentley, M.D., Leonard, D.E., Reynolds, E.K., Leach, S., Beck, A.B., and Murakoshi, I. (1984) Ann. Entomol. Soc. Am., 77, 398. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

622

Opender Koul

LUPININE

C10H19ON (169.27)

M.p. : 68.5–69° B.p. : 255–257°/ mm [α]17 D : –20.35° (EtOH)

CH2OH H

N

(1, 2, 3)

(1, 2)

SOURCE: Commercial sample

(3)

ACTIVITY PROFILE Test Insect Acyrthosiphon pisum (Harris) (Pea aphid)

Test Method

Conc. / Dose

Efficacy

Remarks

Artificial diet feeding

0.00082 ± 0.0003%

Feeding deterrence = 50.0%

Treatment to aphids at random. Concentration = EC50 (3)

LD50 (mice): 15 mg/kg (ivn.) (1) (2) (3) (4)

Karrer, P. (1928) Helv. Chim. Acta, 11, 1062. Gouch, J.F. (1934) J. Am. Chem. Soc., 56, 2434. Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045. (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC

(4)

Insect Antifeedants

LUTEOLIN

623

C15H10O6 (286.24)

M.p. : 328–330° (dec.)

OH OH

HO

O

OH

O

(1)

(1)

SOURCE: Semisynthetic

(2)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 0.03%

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 50–75 aphids at random for 24 h. Concentration = EC50 (2)

LD50 (mice): 180 mg/kg (ipr.) (1) C.f. Merck Index (1983). (2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489. (3) Elangovan, V. (1994) Cancer Lett., 87, 107.

© 2005 by CRC Press LLC

(3)

624

Opender Koul

LUTEONE

C20H18O6 (354.34)

HO

M.p. : 222–223° (dec.) (225–227°)

O

OH

O

OH

HO

(1)

(1)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Costelytra zealandica (White) (Scarab beetle)

2. Heteronychus arator (Fab.) (Pasture scarab beetle)

Test Method Artificial diet feeding

Artificial diet feeding

Conc. / Dose

Efficacy

Remarks

2 µg/ml

Feeding deterrence = 45.6%

100 µg/ml

Feeding deterrence = 92.3%

1. Treatment to 24-h pre-starved 3rd instar larvae. Treatment duration = 24 h. (1)

100 µg/ml

Feeding deterrence = 23.9%

(1) Lane, G.A., Sutherland, O.R.W., and Skipp, R.A. (1987) J. Chem. Ecol., 13, 771.

© 2005 by CRC Press LLC

2. Treatment to 24–h pre-starved 3rd instar larvae. Treatment duration = 24 h. (1)

Insect Antifeedants

LUVANGETIN

625

C15H14O4 (258.27)

M.p. : 108–109°

OCH3 O

O

O

(1, 2)

(1, 3)

SOURCE: Atalantia racemosa Wight, and Arn., wild lime (Rutaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Artificial diet assay

Conc. / Dose 220 ppm

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 4th instar larvae prestarved for 4 h. Treatment duration = 48 h. Concentration = EC50 (2)

(1) Murray, R.D.H. (1978) Prog. Chem. Org. Nat. Prod., 35, 199. (2) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem., 37, 1435. (3) Bose, P.K. (1944) J. Ind. Chem. Soc., 21, 181.

© 2005 by CRC Press LLC

626

Opender Koul

LYCORAMINE CARBONATE

C17H23O3N.½H2CO.2H2O (356.42)

H3CO

M.p. : 130–135° (amorphous)

H

O

OH

+ N

1/2 CO32-

H

(1)

(1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae)

(1)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina DelOrza (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose

Efficacy

0.8%

Feeding ratio = 40.5% (average feeding inhibition)

0.6%

Feeding ratio = 62.8% (no inhibition)

Remarks Treatment to 5th instar larvae after 4 h of pre-starvation. (1)

(1) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983) Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC

Insect Antifeedants

LYCORICIDINE

627

C14H13O6N (291.26)

M.p. : 214.5–215.5° (dec.) [α]20 D : +180° (pyridine)

OH OH H O OH NH

O

O

(1, 2)

(1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae)

(2)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina DelOrza (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose

Efficacy

0.25%

Feeding ratio = 21.9% (slight feeding inhibition)

0.1%

Feeding ratio = 46.0% (medium feeding inhibition)

0.025%

Feeding ratio = 44.2% (medium feeding inhibition)

Remarks Treatment to 5th instar larvae after 4 h of pre-starvation. (2)

(1) Okamoto, T., Torii, Y., and Isogai, Y. (1968) Chem. Pharm. Bull., 16, 1860. (2) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983) Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC

628

Opender Koul

LYCORICIDINOL (narciclasine)

C14H13O7N (307.26)

M.p. : 232–234° (216° dec.)

OH

[α]D : +145° (EtOH) OH H O OH NH

O

OH

O

(1, 2)

(1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae)

(2)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina DelOrza (Yellow butterfly)

LD50 (mice): 5 mg/kg (s.c.)

Test Method Artificial diet feeding

Conc. / Dose

Efficacy

0.25%

Feeding ratio = 13.0% (strong feeding inhibition)

0.1%

Feeding ratio = 15.3% (strong feeding inhibition)

0.025%

Feeding ratio = 29.3% (slight feeding inhibition)

Remarks Treatment to 5th instar larvae after 4 h of pre-starvation. (1)

(3)

(1) Okamoto, T., Torii, Y., and Isogai, Y. (1968) Chem. Pharm. Bull., 16, 1860. (2) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983) Chem. Pharm. Bull., 31, 2146. (3) Piozzi, F. and Marino, M.L. (1969) Phytochemistry, 8, 1745.

© 2005 by CRC Press LLC

Insect Antifeedants

LYCORINE

629

C16H17O4N (287.32)

M.p. : 275–280° (dec.) (262–264°) [α]16 D : –129° (EtOH)

OH HO H O H N

O

(1, 2)

(1, 2)

SOURCE: Hymenocallis littoralis Salisb., lily (Amaryllidaceae) Lycoris radiata Herb., red spider lily (Amaryllidaceae)

(3) (4)

ACTIVITY PROFILE Test Insect 1. Eurema hecabe mandarina DelOrza (Yellow butterfly)

2. Schistocerca gregaria (Forsk.) (Desert locust)

Test Method Artificial diet feeding

Leaf disk test

Conc. / Dose

Efficacy

0.4%

Feeding ratio = 34.0% (slight feeding inhibition)

0.25%

Feeding ratio = 22.8% (medium feeding inhibition)

0.05%

Feeding ratio = 53.5% (no inhibition)

0.1%

Feeding inhibition = 100%

0.05%

Feeding inhibition = 100%

0.025%

Feeding inhibition = 90.5%

Remarks 1. Treatment to 5th instar larvae after 4 h of pre-starvation. (4)

2. Treatment to sexually immature adults for 24 h. (3)

(1) Takagi, S., Taylor, W.I., Uyeo, S., and Hajima, H. (1955) J. Chem Soc., 4003. (2) Wildman, W.C. and Kaufman, C.J. (1954) J. Am. Chem. Soc., 76, 5815. (3) Singh, R.P. and Pant, N.C. (1980) Experientia, 36, 552. (4) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983) Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC

630

Opender Koul

MAACKIAIN

C16H12O5 (284.27)

M.p. : 199–200° (179–181°) [α]22 D : –260° (Me2CO)

HO

O H O H O

O

(1, 2)

(1, 2, 3)

SOURCE: Sophora japonica L., Japanese sophora (Fabaceae) Sophora microphylla Ait., sophora (Fabaceae)

(1) (2, 4)

ACTIVITY PROFILE Test Insect 1. Costelytra zealandica (White) (Scarab beetle)

2. Heteronychus arator (Fab.) (Pasture scarab beetle)

Test Method

Conc. / Dose

Artificial diet feeding

Artificial diet feeding

Efficacy

Remarks

200 µg/ml

Feeding inhibition = 100%

100 µg/ml

Feeding inhibition = 100%

1. Treatment to 24-h starved 3rd instar larvae for 24 h. (4)

200 µg/ml

Feeding inhibition = 52.7%

2. Treatment to 24-h starved 3rd instar larvae for 24 h. (4) Data calculated from Reference 3.

(1) (2) (3) (4)

Ollis, W.D. (1966) Experientia, 22, 777. Briggs, L.H., Cambie, R.C., and Montgomery, R.K. (1975) NZ. J. Sci., 18, 555. Shibata, S. and Yoshihiro, N. (1963) Chem. Pharm. Bull., 11, 167. Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

© 2005 by CRC Press LLC

Insect Antifeedants

MALTOL

631

C6H6O3 (126.11)

M.p. : 160–162°

O OH

O

(1)

(1)

SOURCE: Trifolium repens L., grassland huia (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect Heteronychus arator (Fab.) (Pasture scarab beetle)

Test Method

Conc. / Dose

Artificial diet feeding

Efficacy

Remarks

200 µg/ml

Feeding inhibition = 25.0%

100 µg/ml

Feeding inhibition = 31.6%

1. Treatment to 24-h starved 3rd instar larvae for 24 h. (1) Data calculated from Reference 1. However, the data does not have consistency in different sets of experiments.

LD50 (rats): 2330 mg/kg (oral)

(2)

(1) Russel, G.B., Sutherland, O.R.W., Christmas, P.E., and Wright, H. (1982) NZ. J. Zool., 9, 145. (2) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

632

Opender Koul

MARGARIC ACID

C17H34O2 (270.46)

M.p. : 61° n60 D

: 1.4342

COOH

(1, 2)

(1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

Paper towel disk assay

0.25 mg/cm2

Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Efficacy

Remarks

Feeding deterrence = 90.7%

Treatment to larvae of 10–13 mg body weight for 1 week. (2) Data calculated from Reference 2.

LD50 (mice): 36.0 ± 0.3 mg/kg (i.v.) (1) Bhattacharyya, S.C., Chakravarty, K.K., and Kumar, V. (1959) Chem & Indus., 1352. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. (3) Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

© 2005 by CRC Press LLC

(3)

Insect Antifeedants

MARRUBIN

633

C20H28O4 (332.44)

M.p. : 160° [α]D : +33.3° (CHCl3)

OH

O

O O

(1, 2, 3)

(1, 2)

SOURCE: Marrubium vulgare L., horehound (Labiatae)

(3)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method Leaf disk nochoice test

Conc. / Dose 100 ppm

Efficacy Feeding inhibition = 50.0%

Remarks Treatment to 4-h starved 3rd instar larvae for 24 h. (3)

(1) Fulke, J.W.B., Hederson, M.S., and McCrindle, R. (1968) J. Chem. Soc., 807. (2) Stephens, L.J. and Wheeler, D.M.S. (1970) Tetrahedron, 26, 1561. (3) Taboada, J., Camino, M., Gil, N.M., Campos, E., and Guerrero, C. (1994) Rev. Latinoamer. Quim., 23, 120.

© 2005 by CRC Press LLC

634

Opender Koul

MEDICARPIN

HO

C16H14O4 (270.28)

M.p. : 127.5–128.5°

O

O OCH3

(1)

(1)

SOURCE: Trifolium repens L., grassland huia (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Heteronychus arator (Fab.) (Pasture scarab beetle)

2. Costelytra zealandica (White) (Scarab beetle)

Test Method Artificial diet feeding

Artificial diet feeding

Conc. / Dose

Efficacy

Remarks

200 µg/g

Feeding inhibition = 33.0%

100 µg/g

Feeding inhibition = 25.8%

1. Treatment to 24-h starved 3rd instar larvae for 24 h. (1)

200 µg/g

Feeding inhibition = 62.6%

100 µg/g

Feeding inhibition = 39.9%

2. Treatment to 3rd instar larvae. (2) Data calculated from References 1 and 2.

(1) Russel, G.B., Sutherland, O.R.W., Christmas, P.E., and Wright, H. (1982) NZ. J. Zool., 9, 145. (2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem Syst. Ecol., 8, 73.

© 2005 by CRC Press LLC

Insect Antifeedants

635

MELAMPODININ–A

C25H30O12 (522.50)

O

OH

C

C

M.p. : 208–210°

COOCH3 O O

C

H OAc

AcO CH2 O O

(1, 2)

(1)

SOURCE: Melampodium americanum L., American blackfoot daisy (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method Cellulose millipore filter disk test

Conc. / Dose 1%

Efficacy Feeding inhibition rate = 18.5 mg in 48 h.

Remarks Treatment to 4th instar larvae. Average deterrence rating based on control-treated disk consumption. (2)

(1) Fischer, N.H., Wiley, R.A., Perry, D.L., and Haegele, K.D. (1976) J. Org. Chem., 41, 3956. (2) Smith, C.M., Kester, K.M., and Fischer, N.H. (1983) Biochem. Syst. Ecol., 11, 377.

© 2005 by CRC Press LLC

636

Opender Koul

MELIACARPININ–A

C39H46O14 (738.78)

Data not verified yet

O COOCH3 O

OCH3 OH

O

O

O

AcO

O OH

O

(1, 2)

(1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks 1. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (2)

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

50 ppm

Feeding inhibition = Threshold level

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice test

50 ppm

Feeding inhibition = Threshold level

(1) Nakatani. M., Arikawa, S., Okamura, H., and Iwagawa, T. (1994) Heterocycles, 38, 327. (2) Nakatani. M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

Insect Antifeedants

MELIACARPININ–B

637

C33H44O12 (632.70)

Amorphous powder [α]22 D : –6.7° (MeOH)

COOCH3 OCH3 OH

O

O

O O

O

O

OH

O

(1)

(1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (1)

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

50 ppm

Feeding inhibition = Threshold level

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice test

50 ppm

Feeding inhibition = Threshold level

(1) Nakatani. M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

638

Opender Koul

MELIACARPININ–C

C35H46O14 (690.74)

M.p. : 149–151° or Amorphous powder

COOCH3 H3COOC

[α]22 D : +9.1° (MeOH)

OCH3 OH

O

O

O O

O

O

OH

O

(1)

(1) SOURCE: Melia azedarach L., chinaberry (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (1)

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

50 ppm

Feeding inhibition = Threshold level

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice test

50 ppm

Feeding inhibition = Threshold level

(1) Nakatani. M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

Insect Antifeedants

MELIACARPININ–D

639

C35H46O14 (690.74)

M.p. : 165–167° [α]22 D : –8.3° (MeOH)

O COOCH3 O

OCH3 OH

O

O

O

AcO

O OH

O

(1)

(1) SOURCE: Melia azedarach L., chinaberry (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks 1. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (1)

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

50 ppm

Feeding inhibition = Threshold level

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice test

50 ppm

Feeding inhibition = Threshold level

(1) Nakatani. M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

640

Opender Koul

MELIACARPININ–E

C33H44O13 (648.70)

[α]20 D : –10° (MeOH)

COOCH3 HO

OCH3 OH

O

O

O O

O

O

OH

O

(1)

(1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Cramer) (Southern armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

1 µg/cm2

Efficacy

Remarks

Feeding inhibition = Threshold level

1. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (1)

(1) Huang, R.C., Tadera, K., Yagi, F., Minami, Y., Okamura, H., Iwagawa, T., and Nakatani. M. (1996) Phytochemistry, 43, 581.

© 2005 by CRC Press LLC

Insect Antifeedants

MELIANONE

641

C30H46O4 (470.69)

M.p. : 232–233°

O

[α]D : –62° (CHCl3)

O HO

O

(1, 2)

(1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Bean leaf choice test

Conc. / Dose 0.05%

Efficacy

Remarks

Feeding inhibition = Threshold level

Treatment to 4th stadium larvae. No quantitative data recorded. (1)

(1) Kraus, W. and Grimminger, W. (1980) Nouv. J. Chim., 4, 651. (2) Lavie, D., Jain, M.K., and Kirson, I. (1967) J. Chem. Soc. (C), 1347.

© 2005 by CRC Press LLC

642

Opender Koul

MELIANOTRIOL

C30H50O5 (490.72)

M.p. : 76–178° [α]D : –23° (CHCl3)

OH OH

O

OH

HO

(1)

(1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Cramer) (Southern armyworm)

Test Method Filter paper test

Conc. / Dose 8 γ /cm2

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to 5th midstadium larvae. (1)

(1) Lavie, D., Jain, M.K., and Shpan-Gabrielith, S.R. (1967) Chem. Commun., 910.

© 2005 by CRC Press LLC

Insect Antifeedants

MELICOPICINE

643

C18H19O5N (329.35)

OCH3

M.p. : 133–134°

O

H3CO

N

H3CO OCH3

(1, 2)

(1)

SOURCE: Teclea trichocarpa Engl., African evergreen teclea (Meliaceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera exempta (Walker) (Nutgrass armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding inhibition = 100%

1. Treatment to 3rd instar larvae for 2 h. (2)

(1) Price, J.R. (1949) Aust. J. Sci. Res., A2, 249. (2) Lwande, W., Gebreyesus, T., Chapya, A., MacFoy, C., Hassanali, A., and Okech, M. (1983) Insect Sci. Applic., 4, 393.

© 2005 by CRC Press LLC

644

Opender Koul

MELIATOXIN–A2

C34H44O12 (644.71) O

OH

M.p. : 155–160° (dec.) [α]22 D : –72.5° (MeOH)

O

AcO O

O AcO

OH

COO H

(1, 2)

(2)

SOURCE: Melia azedarach L. var. australasia, chinaberry (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk choice test

2. Spodoptera eridania (Cramer) (Southern armyworm)

3. Spodoptera exigua (Hubner) (Beet armyworm)

Test Insect

(1) (2) (3) (4)

Efficacy

Remarks

360 ppm

Feeding inhibition = 50.0%

1. Treatment to larvae of 9 to 11 mg body weight. Concentration = EC50 (3)

Leaf disk choice test

400 ppm

Threshold deterrence level

Leaf disk choice test

400 ppm

Threshold deterrence level

2, 3. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (4)

Oelrichs, P.B., Hill, M.W., Vallely, P.J., MacLeod, J.K., and Molinski, T.F. (1983) Phytochemistry, 22, 531. Nakatani, M., Huang, R.C., Okamura, H., Naoki, H., and Iwagawa, T. (1994) Phytochemistry, 36, 39. MacLeod, J.K., Moeller, P.D.R., Molinski, T.F., and Koul, O. (1990) J. Chem. Ecol., 16, 2511. Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

Insect Antifeedants

MELIATOXIN–B1

645

C35H46O12 (658.74)

M.p. : 140–150° (dec.)

O

O

AcO O O AcO

OH

COO H

(1, 2)

(1, 2)

SOURCE: Melia azedarach L. var. australasia, chinaberry (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

450 ppm

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to larvae of 9 to 11 mg body weight. Concentration = EC50 (2)

(1) Oelrichs, P.B., Hill, M.W., Vallely, P.J., MacLeod, J.K., and Molinski, T.F. (1983) Phytochemistry, 22, 531. (2) MacLeod, J.K., Moeller, P.D.R., Molinski, T.F., and Koul, O. (1990) J. Chem. Ecol., 16, 2511.

© 2005 by CRC Press LLC

646

Opender Koul

o-METHOXYACETOPHENONE

C9H10O2 (150.18)

Oil B.p. : 125–126°/12 mm

OCH3

O

(1, 2)

(2)

SOURCE: Commercial sample

(1, 2)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora (Boisd.) (Cabbage butterfly)

Test Method Leaf disk dual-choice test

Conc. / Dose 5 × 10–7 mol/cm2

Efficacy

Remarks

Feeding inhibition = 49.3%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 2 h. (1)

(1) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130. (2) Laird, R.M. and Parker, R.E. (1961) J. Am. Chem. Soc., 83, 4277.

© 2005 by CRC Press LLC

Insect Antifeedants

m-METHOXYACETOPHENONE

647

C9H10O2 (150.18)

Oil B.p. : 131°/18 mm

OCH3

O

(1, 2)

(1, 2)

SOURCE: Commercial sample Also found in many plant spp.

(1, 2)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora (Boisd.) (Cabbage butterfly)

Test Method Leaf disk dual-choice test

Conc. / Dose 5 × 10–7 mol/cm2

Efficacy

Remarks

Feeding inhibition = 96.8%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 2 h. (1)

(1) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC

648

Opender Koul

p-METHOXYACETOPHENONE

C9H10O2 (150.18)

M.p. : 37.5–38.5° B.p. : 138–139°/15 mm

OCH3

O

(1)

(1)

SOURCE: Commercial sample

(1)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method Leaf disk dual-choice test

Conc. / Dose 5 × 10–7 mol/cm2

Efficacy

Remarks

Feeding inhibition = 78.1%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 2 h. (1)

(1) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130.

© 2005 by CRC Press LLC

Insect Antifeedants

5-METHOXY-N,N-DIMETHYL TRYPTAMINE (Bufotenine)

649

C13H18ON2 (218.30)

M.p. : 67.5–68.5° B.p. : 208–210°/4 mm

H3CO

N

N H

(1, 2)

(1)

SOURCE: Commercial sample Occurs in Phalaris tuberosa (Graminae) and Leguminosae plants.

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Rhopalosiphum maidis (Fitch) (Corn leaf aphid)

Artificial diet feeding

4 mM

Feeding inhibition = 25.2%

1. Treatment to aphids at random for 5 h. (2)

2. Anthonomus grandis Bohem. (Boll weevil)

Agar plug bioassay

5.0 µg/mm2

Feeding inhibition = 3.5%

2. Treatment to newly emerged boll weevils for 4 h in dark. (3)

LD50 (mice): 115 mg/kg (ipr.) (1) (2) (3) (4)

(4)

Pachter, I.J., Zacharias, D.E., and Ribeiro, O. (1959) J. Org. Chem., 24, 1283. Corcuera, L.J. (1984) Phytochemistry, 23, 539. Miles, D.H., Ly, A.M., Randle, S.A., Hedin, P.A., and Burks, M.L. (1987) J. Agric. Food Chem., 35, 794. Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

650

Opender Koul

5-METHOXYISOLONCHOCARPIN

C21H20O4 (336.39)

O

Configuration not determined

O

OCH3

O

(1) SOURCE: Tephrosia vogelii Hook F., vogel tephrosia (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nutgrass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dualchoice test

Glass fiber disk dualchoice test

Efficacy

Remarks

100 ppm

Feeding inhibition = 80.0%

10 ppm

Feeding inhibition = 35.0%

1. Treatment to 24- to 36-h-old final stadium larvae for 5 hours. Larvae prestarved for 4 h. (1)

100 ppm

Feeding inhibition = 64.0%

10 ppm

Feeding inhibition = 59.0%

2. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (1)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

Insect Antifeedants

7-O-METHYL-8-(3-METHYLBUTADIENYL) -FLAVANONE

651

C22H23O3 (335.40)

No physical data given

CH2

H3CO

O

O

(1)

(1)

SOURCE: Tephrosia purpurea (L.) Pers., wild indigo (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nutgrass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dualchoice test

Glass fiber disk dualchoice test

Efficacy

Remarks

100 ppm

Feeding inhibition = 69.0%

10 ppm

Feeding inhibition = 42.0%

1. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (1)

100 ppm

Feeding inhibition = 43.0%

10 ppm

Feeding inhibition = 85.0%

2. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (1)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

652

Opender Koul

(+) 2-METHOXYPHASEOLLINISOFLAVAN

C21H22O4 (338.40)

M.p. : 135–136° [α]24 D : +19.5° (EtOH)

HO

O

H3CO

O

(1)

(1) SOURCE: Phaseolus vulgaris L., french bean (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Costelytra zealandica (White) (Scarab beetle)

Test Method Artificial diet feeding

Conc. / Dose

Efficacy

Remarks

10 µg/ml

Feeding inhibition = 100%

1 µg/ml

Feeding inhibition = 42.9%

1. Treatment to 24-h starved 3rd instar larvae for 24 h. (2) Data calculated from Reference 2.

(1) Van Etten, H.D. (1973) Phytochemistry, 12, 1791. (2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

© 2005 by CRC Press LLC

Insect Antifeedants

2-METHOXYPHENOL

653

C7H8O2 (124.14)

M.p. : 32° (prisms) B.p. : 105–110°/0.3 mm n25 D

OH

: 1.5256

OCH3

(1, 2)

(1, 2) SOURCE: Found in many essential oils and resins

(1, 2)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk assay

Conc. / Dose 0.1%

0.5%

LD50 (rats): 725 mg/kg (oral)

Efficacy

Remarks

Feeding deterrence = 100% up to 6 h. Reduction in deterrence by 11% in 22 h.

Treatment to adult beetles. (1) Data calculated from Reference 1.

Feeding deterrence = 100% up to 22 h.

(3)

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378. (2) Karrer, W. (1958) Konstitution und Vorkommen der Organischen Pflanzenstoffe, Vol. 1, Birkhauser Verlag, Basel, p. 72. (3) Opdyke, D.L.J. (1982) Food Cosmet. Toxicol., 20, 697

© 2005 by CRC Press LLC

654

Opender Koul

3-METHOXYPHENOL

C7H8O2 (124.14)

B.p. : 110–115°/0.3 mm n25 D

: 1.5276

OH

OCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk assay

Conc. / Dose 0.5%

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.

© 2005 by CRC Press LLC

Efficacy

Remarks

Feeding deterrence = 100% up to 22 h.

Treatment to adult beetles. (1)

Insect Antifeedants

4-METHOXYPHENOL

655

C7H8O2 (124.14)

M.p. : 53° B.p. : 100–103°/0.5 mm n25 D

OH

: 1.5228

OCH3

(1, 2)

(1) SOURCE: Synthetic Also from the leaves of Pirola secunda L., serrated wintergreen (Pyrolaceae)

(1,3)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

LD50 (rats): 1600 mg/kg (oral)

Test Method Leaf disk assay

Conc. / Dose 0.5%

Efficacy

Remarks

Feeding deterrence = 100% up to 22 h.

Treatment to adult beetles. (1)

(4)

(1) Reed, D.K. and Jacobson. M. (1983) Experientia, 39, 378. (2) Penner, G.H. and Wasylishen, R.E. (1989) Can. J. Chem., 67, 525. (3) Karrer, W. (1958) Konstitution und Vorkommen der Organischen Pflanzenstoffe, Vol. 1, Birkhauser Verlag, Basel, p. 88. (4) (1993) Patty’s Ind. Hyg. Toxicol., 4th edition, Vol. 2, Wiley, New York.

© 2005 by CRC Press LLC

656

Opender Koul

5-METHOXYTRYPTAMINE

C11H14ON2 (190.24)

M.p. : 121–122°

H3CO

NH2

N H

(1, 2)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Rhopalosiphum maidis (Fitch) (Corn leaf aphid)

Test Method Artificial diet feeding

Conc. / Dose 4 mM

Efficacy

Remarks

Feeding inhibition = 26.1%

Treatment to aphids at random for 5 h. (2) Data calculated from Reference 2.

LD50 (mice): 176 mg/kg (ipr.)

(3)

(1) Suniewski, J. and Misztal, S. (1960) Bull. Acad. Polon. Sci. Ser. Sci. Biol., 8, 479. (cf. CA 55, 15458). (2) Corcuera, L.J. (1984) Phytochemistry, 23, 539. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

METHYL ABIETATE

657

C21H32O2 (316.48)

B.p. : 360–365° n20 D

: 1.530

No structure given

(1, 2)

(1)

SOURCE: Commercial mixture of coniferous resin acids and methyl esters

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk assay

0.05 mg/cm2

Efficacy

Remarks

Feeding deterrence = 31.8% after 6 days

Treatment to immature termites of 10–13 mg body weight. (2)

(1) (1983), Merck Index, p. 863. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC

658

Opender Koul

METHYL 2(Z)-10-ACETOXY-8,9EPOXYDECEN-4,6-DIYNOATE

C13H12O5 (248.23)

Oil

O OAc

H3COOC

(1)

(1)

SOURCE: Chrysothamnus nauseosus (pall.) Britt., rubber rabbit bush (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk assay

Conc. / Dose < 35 µg/cm2

Efficacy Feeding deterrence = threshold level

(1) Rose, A.F., Butt, B.A., and Jermy, T. (1980) Phytochemistry, 19, 563.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar larvae. (1)

Insect Antifeedants

METHYL Z,Z-10-ACETOXY MATRICARIATE

659

C13H12O4 (232.23)

Oil

OAc

H3COOC

(1)

(1)

SOURCE: Chrysothamnus nauseosus (pall.) Britt., rubber rabbit bush (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method

Conc. / Dose

Leaf disk assay

35–70 µg/cm2

Efficacy Feeding deterrence = threshold level

(1) Rose, A.F., Butt, B.A., and Jermy, T. (1980) Phytochemistry, 19, 563.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar larvae. (1)

660

Opender Koul

METHYL ARISTOLOCHIATE

C18H13O7N (355.31)

M.p. : 285–286°

COOCH3

O

NO2

O

OCH3

(1)

(2)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk choice assay

1000 ppm

Efficacy Feeding deterrence index = 30.86

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1993a) J. Agric. Food Chem., 41, 2426. (2) Lajide, L., Escoubas, P., and Mizutani, J. (1993b) J. Agric. Food Chem., 41, 669.

© 2005 by CRC Press LLC

Remarks Treatment to 4-dayold larvae for 1 day. Antifeedant index value shows moderate activity. The value below 20 is highly deterrent index. (1)

Insect Antifeedants

3β-p-METHYLCINNAMATOXYLUP-20-EN28-OIC ACID

661

C42H60O4 (628.89)

M.p. : 225°

CH2

COOH

COO

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice assay

Conc. / Dose

Efficacy

Remarks

100 µg/2 cm diameter disk

Feeding deterrence = 74.0%

Treatment to freshly molted 4th instar larvae for 48 h. (1)

50 µg/2 cm diameter disk

Feeding deterrence = 46.0%

25 µg/2 cm diameter disk

Feeding deterrence = 33.0%

(1) Jagadeesh, S.G., Krupadanam, G.L.D., and Srimannarayana, G. (1998) J. Agric. Food. Chem., 46, 2797.

© 2005 by CRC Press LLC

662

Opender Koul

3-O-METHYL-3-DEACETYLSALANNIN

C33H44O8 (568.71)

Only spectral data given

O

O

O

O O H

O H3CO

H

O

(1) SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Conc. / Dose 100 µg/cm2

Efficacy

Remarks

Feeding deterrence = 95.0%

Treatment to newly molted 3rd instar larvae. Disks examined every 2 h until 95% of control disks were consumed. Concentration = PC95 value. (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC

Insect Antifeedants

663

3-O-METHYL-3-DEACETYL-2′,3′, 20,21,22,23-HEXAHYDROSALANNIN

C33H50O8 (574.75)

Only spectral data given

O O

COO

O H

O H3CO

H

O

(1) SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

10 µg/cm2

Feeding deterrence = 95.0%

2 µg/cm2

Feeding deterrence = 50.0%

Treatment to newly molted 3rd instar larvae. Disks examined every 2 h until 95% of control disks were consumed. Concentrations = PC95 and PC50 values. (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC

664

Opender Koul

METHYL α-ELEOSTEARATE

C19H32O2 (292.46)

B.p. : 210°/12 mm n25 D

: 1.5000

COOCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Anthonomus grandis grandis Bohem. (Boll weevil)

Test Method Cotton bud dip method

Conc. / Dose 1.0%

Efficacy

Remarks

Feeding deterrence = 73.9%

Treatment to 1- or 2day-old boll weevils for 4 h. Data based on the number of bud punctures in treated and control experiments. (1) Data calculated from Reference 1.

(1) Jacobson, M., Crystal, M.M., and Warthen, J.D. Jr. (1981) J. Agric. Food Chem., 29, 591.

© 2005 by CRC Press LLC

Insect Antifeedants

METHYL 6,11β-DIHYDROXY-12α-(2-METHYL PROPANOYLOXY)-3,7-DIOXO-14β,15β-EPOXY1,5-MELIACADIEN-29-OATE

665

C31H37O10 (569.24)

Only spectral data given

O O O HO

O O H3COOC

O OH

(1)

(1)

SOURCE: Trichilia pallida Sw., Kew trichila (Meliaceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk test

2. Spodoptera exigua (Hubner) (Beet armyworm)

Test Insect

Efficacy

Remarks

100 ppm

Feeding deterrence = 46%

Glass fiber disk test

100 ppm

Feeding deterrence = 40%

Treatment to final stadium larvae, 36–48 h into the stadium pre-starved for 2–3 h.

3. Heliothis virescens (Fab.) (Tobacco budworm)

Glass fiber disk test

100 ppm

Feeding deterrence = 49%

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Glass fiber disk test

100 ppm

Feeding deterrence = 42%

Treatment duration = 18 h. (1)

(1) Simmonds, M.S.J., Stevenson, P.C., Porter, E.A., and Veitch, N.C. (2001) J. Nat. Prod., 64, 1117.

© 2005 by CRC Press LLC

666

Opender Koul

3,4-METHYLENEDIOXY BENZYL ALCOHOL

C8H8O3 (152.15)

B.p. : 131–135°/0.4 mm n25 D

: 1.5287

CH2OH

O O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk assay

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding deterrence = 100% up to 6 h.

Treatment to adult beetles. (1)

0.5%

Feeding deterrence = 100% up to 22 h.

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.

© 2005 by CRC Press LLC

Insect Antifeedants

3,4-METHYLENEDIOXY PHENOL

667

C7H6O3 (138.12)

B.p. : 120–125°/0.3 mm nD25

: 1.5368

OH

O O

(1)

(1) SOURCE: Synthetic Also occurs naturally in sesame oil

(1) (2)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk assay

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding deterrence = 100% up to 6 h.

Treatment to adult beetles. (1)

0.5%

Feeding deterrence = 100% up to 22 h.

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378. (2) Beroza, M. (1954) J. Am. Oil Chem. Soc., 31, 302.

© 2005 by CRC Press LLC

668

Opender Koul

N-METHYL-TRANS-4-HYDROXY-L-PROLINE

C6H11O3N (145.16)

M.p. : 237–241° (dec.) [α]D : –74° (MeOH) : –86.6° (H2O)

H

H N OH

H

H

H

H

COOH

(1)

(1) SOURCE: Copaifera spp., copaiba (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Leaf disk choice test

Efficacy

Remarks

100 ppm

Feeding inhibition index = 11.2 ± 8.24

1000 ppm

Feeding inhibition index = 26.7 ± 11.41

Treatment to larvae at random. Antifeedant effect significant at 1000 ppm level. (1)

(1) Figliuolo, R., Naylor, S., Wang, T., and Langenheim, J.H. (1987) Phytochemistry, 26, 3255.

© 2005 by CRC Press LLC

Insect Antifeedants

E-3- (3,4-METHYLENEDIOXYPHENYL)-N2-[OCTADECYL]-2-PROPENAMIDE

669

C28H45O3N (443.67)

M.p. : 100–101°

O O

(CH2)15.CH3 N H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Reticulitermes speratus (Kolbe) (Subterranean termite)

Paper disk choice assay

5000 ppm

Efficacy Feeding deterrence index = 10.9

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. The value below 20 is highly deterrent effect. (1)

670

Opender Koul

1,5-BIS-(3,4-METHYLENEDIOXYPHENYL) PENT-1,4-DIEN-3-ONE

C19H14O5 (322.32)

M.p. : 198–200°

O

O

O

O

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Reticulitermes speratus (Kolbe) (Subterranean termite)

Test Method Paper disk choice assay

Conc. / Dose 10,000 ppm

Efficacy Feeding deterrence index = 18.0

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1097.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. The value below 20 is highly deterrent effect. (1)

Insect Antifeedants

E-3- (3,4-METHYLENEDIOXYPHENYL)-N2-[4-HYDROXYPHENYLETHYL]2-PROPENAMIDE

C18H17O4N (311.34)

M.p. : 168–170°

OH

O

O

671

N H

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Reticulitermes speratus (Kolbe) (Subterranean termite)

Paper disk choice assay

5000 ppm

Efficacy Feeding deterrence index = 25.9

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. The value below 20 is highly deterrent effect. (1)

672

Opender Koul

METHYL ESTER OF VACHANIC ACID

C16H26O3 (266.38)

M.p. : 55–56° [α]20 D : –36.9° (CHCl3)

CH2

H

COOCH3

HO

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 158.5

1. Treatment given to adults.

2. Tribolium confusum (Duv.) (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient Adults = 137.7 Larvae = 162.2

2. Treatment given to both adults and larvae.

3. Trogoderma granarium (Everts) (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 61.5

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200. (1)

(1) Daniewski, W.M., Kroszczynski, W., Bloszyk, E., Drozdz, B., Grabarczyk, H., Nawrot, J., Rychlewska, U., Budesinsky, M., and Holub, M. (1986) Collect. Czech. Chem. Commun., 51, 1710.

© 2005 by CRC Press LLC

Insect Antifeedants

METHYL EUGENOL

673

C11H14O2 (178.23)

B.p. : 128–129°/11 mm (125–127°/12 mm)

OCH3

nD20

OCH3

: 1.532

CH2

(1, 2)

(1)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora (Boisd.) (Cabbage butterfly)

LD50 (rats): 1179 mg/kg (oral)

Test Method Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

10–1 mol/l

Feeding inhibition = 100%

10–2 mol/l

Feeding inhibition = 80.0%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 2 h. (2, 3)

(4)

(1) Nagasawa, M. (1961) J. Pharm. Soc. Jap., 81, 129. (2) Yano, K. (1987) J. Agric. Food Chem., 35, 889. (3) Yano, K. and Kamimura, H. (1993) Biosci. Biotech. Biochem., 57, 129. (4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

674

Opender Koul

METHYL GALLATE

C8H8O5 (184.15)

M.p. : 157°

COOCH3

HO

OH OH

(1, 2)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

103 ppm

Feeding inhibition = 50%

Treatment to aphids at random.

2. Acyrthosiphon pisum (Harris) (Pea aphid)

Artificial diet feeding

218 ppm

Feeding inhibition = 50.0%

Concentration = EC50 values. (2)

3. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

303 ppm

Feeding inhibition = 50.0%

LD50 (mice): 1700 mg/kg (oral)

(3)

(1) Lajis, N.H. and Khan, M.N. (1994) Ind. J. Chem., 33B, 609. (2) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

14 – METHYL HEXADECANOIC ACID

675

C17H34O2 (270.45)

M.p. : 39–40° [α]29 D : +5.2° (Me2CO)

(CH2)12COOH

H3C

C

H

CH2.CH3

(1, 2)

(1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae)

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk assay

Efficacy

Remarks

0.25 mg/cm2

Feeding deterrence = 34.7% after 7 days

0.05 mg/cm2

Feeding deterrence = 16.4% after 6 days

Treatment to immature termites of 10–13 mg body weight. (2) Data calculated from Reference 2.

(1) Nunn, J.R. (1951) J. Chem. Soc., 1740. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC

676

Opender Koul

METHYL-p-HYDROXY BENZOATE

C8H8O3 (152.15)

M.p. : 131° (127–129°) B.p. : 270–280° (dec.)

COOCH3

OH

(1, 2)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Pieris brassicae (L.) (Large white butterfly)

Test Method Leaf disk no- choice test

Conc. / Dose 6.6 × 10–2 M

Efficacy Feeding inhibition ratio = 14.21

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.

© 2005 by CRC Press LLC

Remarks Treatment to 2nd day 5th instar un-starved larvae. Ratio less than 20 highly deterrent. (2)

Insect Antifeedants

METHYL 2(Z)-10-HYDROXY-8,9EPOXYDECEN-4,6-DIYNOATE

677

C11H10O4 (206.20)

M.p. : 53–54° (Uncorrected)

O OH

H3COOC

(1)

(1)

SOURCE: Chrysothamnus nauseosus (pall.) Britt., rubber rabbit bush (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk assay

Conc. / Dose < 35 µg/cm2

Efficacy Feeding deterrence = threshold level.

(1) Rose, A.F., Butt, B.A., and Jermy, T. (1980) Phytochemistry, 19, 563.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar larvae. (1)

678

Opender Koul

METHYL 2(Z), 8(Z)-10-HYDROXY MATRICARITE

C11H10O3 (190.20)

M.p. : 38.5–40.5° (Uncorrected)

CH2OH H3COOC

(1)

(1)

SOURCE: Chrysothamnus nauseosus (pall.) Britt., rubber rabbit bush (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk assay

Conc. / Dose < 35 µg/cm2

Efficacy Feeding deterrence = threshold level.

(1) Rose, A.F., Butt, B.A., and Jermy, T. (1980) Phytochemistry, 19, 563.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar larvae. (1)

Insect Antifeedants

METHYLISOCEDRELONATE

679

C26H30O6 (458.52)

Only spectral data given

O

O

O

COOCH3 HO

(1)

(1, 2)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding inhibition = 42.5%

Treatment to 3rd instar larvae for 24 h. (2)

5 µg/cm2

Feeding inhibition = 52.5%

10 µg/cm2

Feeding inhibition = 58.5%

50 µg/cm2

Feeding inhibition = 74.1%

EC50 = 2.97 µg/cm2 Data calculated from Reference 2.

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumatri, G.N. (1995) J. Chem. Ecol., 21, 1585.

© 2005 by CRC Press LLC

680

Opender Koul

16-METHYLKAUR-15-EN-19-OIC ACID

C20H30O2 (302.46)

M.p. : 171–172°

COOH

(1)

(1)

SOURCE: Wedelia biflora (L.) DC., sami scandent shrub (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Anthonomus grandis (Bohem.) (Cotton boll weevil)

Agar plug bioassay

13.0 mg/plug

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to newly emerged boll weevils in the dark at 80°F for 4 h. Plug size: diameter = 1.3 cm length = 3.6 cm. (1)

(1) Miles, D.H., Chittawong, V., Payne, A.M., Hedin, P.A., and Kokpol, U.. (1990) J. Agric. Food Chem., 38, 1591.

© 2005 by CRC Press LLC

Insect Antifeedants

O-METHYL LYCORENINE

681

C19H25O4N (331.41)

M.p. : 121–125° [α]24 D : + 198° (MeOH)

N H H3CO

O H3CO H

OCH3

(1)

(1) SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae)

(1)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina DelOrza (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose 0.8%

Efficacy Feeding ratio = 32.4% (moderate feeding inhibition)

Remarks Treatment to 5th instar larvae after 4 h of pre-starvation. (1)

(1) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983) Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC

682

Opender Koul

2-METHYL-6-METHOXY-1,2,3,4TETRAHYDRO-β-CARBOLINE

C13H16ON2 (216.28)

M.p. : 207–208°

H3CO

N N H

(1)

(1)

SOURCE: Virola calophylla (Spruce) Warb., Peruvian virola (Myristicaceae)

(1)

ACTIVITY PROFILE Test Insect Anthonomus grandis (Bohem.) (Cotton boll weevil)

Test Method Agar plug bioassay

Conc. / Dose 3.0 µg/mm2

Efficacy

Remarks

Feeding inhibition = 49.0%

Treatment to newly emerged boll weevils for 4 h in dark. (1)

(1) Miles, D.H., Ly, A.M., Randle, S.A., Hedin, P.A., and Burks, M.L. (1987) J. Agric. Food Chem., 35, 794.

© 2005 by CRC Press LLC

Insect Antifeedants

3-O-METHYLNIVEUSIN–A

683

C21H28O8 (408.45)

Only spectral data given

O OH O O H3CO

O CH2 OH O

(1)

(1)

SOURCE: Helianthus annuus L., sunflower (Asteraceae)

(1, 2)

ACTIVITY PROFILE Test Insect Diabrotica virgifera virgifera (LeConte) (Western corn rootworm)

Test Method

Conc. / Dose

Leaf disk test

Efficacy

Remarks

40.0 µg/1.5 cm2

Feeding inhibition = about 40.0% in 5 h and 25.0% in 24 h

Treatment to adults. (2)

80.0 µg/1.5 cm2

Feeding inhibition = about 57.0% in 5 h and 70.0% in 24 h

(1) Alfatafta, A.A. and Mullin, C.A. (1992) Phytochemistry, 31, 4109. (2) Mullin, C.A., Alfatafta, A.A., Harman, J.L., Everett, S.L., and Serino, A.A. (1991) J. Agric. Food Chem., 39, 2293.

© 2005 by CRC Press LLC

684

Opender Koul

METHYL OCTADECANOATE

C19H38O2 (298.51) M.p. : 39.1° B.p. : 21.5°/15 mm H3CO

O

(1, 2)

(1)

SOURCE: Synthetic Also occurs in many plant spp.

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk assay

0.05 mg/cm2

Efficacy

Remarks

Feeding deterrence = 8.0% after 6 days

Treatment to immature termites of 10–13 mg body weight. (2) Data calculated from Reference 2.

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC

Insect Antifeedants

2 – METHYLOCTADECANOIC ACID

685

C19H38O2 (298.51)

M.p. : 55° B.p. : 200°/2mm

COOH

H

C

CH3

CH2 (CH2)14CH3

(1, 2)

(1)

SOURCE: Synthetic Also occurs in the uropygial gland of the night heron

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk assay

0.05 mg/cm2

Efficacy

Remarks

Feeding deterrence = 22.8% after 6 days

Treatment to immature termites of 10–13 mg body weight. (2) Data calculated from Reference 2.

(1) Morgan, G.T. and Holmes, E. (1927) J. Soc. Chem. Ind., 46, 152T. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC

686

Opender Koul

3 – METHYLOCTADECANOIC ACID

C19H38O2 (298.51)

M.p. : 44° [α]20 D : +4.84°

COOH

H3C (CH2)14H2C

C

H

CH3

(1, 2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk assay

0.05 mg/cm2

Efficacy

Remarks

Feeding deterrence = 12.9% after 6 days

Treatment to immature termites of 10–13 mg body weight. (2) Data calculated from Reference 2.

(1) Stallberg-Stenhagen, S. (1949) Arkiv. Kemi., 1, 187. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC

Insect Antifeedants

7-O-METHYLPHASEOLLIN

687

C21H20O4 (336.39)

H3CO

M.p. : 120–122°

O H

H O O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Artificial diet feeding

Conc. / Dose 0.35 µg/g

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 24-h starved 3rd instar larvae. Concentration = FI50 value. (1)

(1) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) J. Chem. Ecol., 11, 1731.

© 2005 by CRC Press LLC

688

Opender Koul

(+)-2′-O-METHYLPHASEOLLIN ISOFLAVAN

HO

C21H22O4 (338.40)

[α]20 D : + 19.5° (EtOH)

O

O

H3CO

(2)

(1) SOURCE: Synthetic (Also from Phaseolus vulgaris L., kidney bean (Fabaceae)

(1) (2)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Artificial diet feeding

Conc. / Dose 0.21 µg/g

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 24-h starved 3rd instar larvae. Concentration = FI50 value. (1)

(1) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) J. Chem. Ecol., 11, 1731. (2) V. Etten, H.D. (1973) Phytochemistry, 12, 1791.

© 2005 by CRC Press LLC

Insect Antifeedants

7-O-METHYL-8-PRENYLFLAVANONE

H3CO

689

C22H24O3 (336.41)

No physical data given

O

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nutgrass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dualchoice test

Glass fiber disk dualchoice test

Efficacy

Remarks

100 ppm

Feeding inhibition = 65.0%

10 ppm

Feeding inhibition = 29.0%

1. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (2)

100 ppm

Feeding inhibition = 73.0%

2. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (2)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

690

Opender Koul

METHYLSAINFURAN

H3CO

C17H16O5 (300.31)

M.p. : 147–148°

OCH3

OH

O OCH3

(1)

(1)

SOURCE: Onobrychis viciifolia Scop., mainfoin (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Artificial diet feeding

Conc. / Dose 2 µg/g

Efficacy Feeding deterrence reported statistically significant. No quantitative data given.

Remarks Treatment to 24-h starved 3rd instar larvae. (1)

(1) Russel, G.B., Shaw, G.J., Christmas, P.E., Yates, M.B., and Sutherland, O.R.W. (1984) Phytochemistry, 23, 1417.

© 2005 by CRC Press LLC

Insect Antifeedants

Nω-METHYLTRYPTAMINE

691

C11H14O2 (174.25)

M.p. : 90° (87–88°)

NH

N H

(1, 2, 3)

(1, 2)

SOURCE: Commercial material Occurs in Myristicaceae and Rutaceae plants

(3)

ACTIVITY PROFILE Test Insect Rhopalosiphum maidis (Fitch) (Corn leaf aphid)

Test Method Artificial diet feeding

Conc. / Dose 4 mM

Efficacy

Remarks

Feeding deterrence = 24.3%

Treatment to aphids at random. Treatment duration = 5 h. (3) Data calculated from Reference 3.

(1) Yurashevskii, N.K. and Stepanov, S.I. (1939) J. Gen. Chem. USSR, 9, 2203. (2) Yurashevskii, N.K. (1940) J. Gen. Chem. USSR, 10, 1781. (3) Corcuera, L.J. (1984) Phytochemistry, 23, 539.

© 2005 by CRC Press LLC

692

Opender Koul

MONOCROTALINE

C16H23O6N (325.36)

M.p. : 202–203° (197–198°)

OH

[α]26 D : –54.7° (CHCl3) HC

C

C

COO

HO

CH2OCO

N

(1, 2)

(1, 2)

SOURCE: Crotalaria spectabilis Roth, showy crotalaria (Fabaceae)

(3)

ACTIVITY PROFILE Test Insect Acyrthosiphon pisum (Harris) (Pea aphid)

LD50 (rats): 66 mg/kg (oral)

Test Method Artificial diet feeding

Conc. / Dose 0.05 ± 0.03%

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to aphids at random. Concentration = EC50 value. (3)

(4)

(1) Adams, R. and Rogers, E.F. (1939) J. Am. Chem. Soc., 61, 2815. (2) Adams, R. and Rogers, E.F. (1950) J. Am. Chem. Soc., 72, 158. (3) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045. (4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

MONOMETHOXYCHALCONE (4-Methoxylonchocarpin)

693

C21H20O4 (336.39)

M.p. : 130° (109°)

O OCH3

OH

O

(1)

(1)

SOURCE: Millettia pachycarpa Benth., rosewood (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Philosamia ricini (Hutt.) (Eri-silkworm)

Test Method Leaf disk test

Conc. / Dose 1.0%

Efficacy

Remarks

Feeding inhibition = 90.0%

Treatment to larvae. (2)

(1) Singhal, A.K., Barua, N.C., Sharma, R.P., and Baruah, J.N. (1983) Phytochemistry, 22, 1005. (2) Barua, N.C., Barua, P., Goswami, A., Sharma, R.P., and Baruah, J.N. (1983) Chem. & Indus., 23, 900.

© 2005 by CRC Press LLC

694

Opender Koul

MORIN

C15H10O7 (302.24)

OH

HO

HO

M.p. : 303–304° (285–290°, anhydrous, dec.)

O

OH OH

O

(1, 2)

(1)

SOURCE: Chlophora tinctoria (L.) Candich. Ex Benth. and Hook f., fustic mulberry (Moraceae) and many other plants

(1, 2)

ACTIVITY PROFILE Test Insect 1. Schizaphis graminum (Rondani) (Wheat aphid)

Test Method Artificial diet feeding

Conc. / Dose 0.04%

Efficacy Feeding inhibition = 50.0%

Remarks 1. Treatment to 50–75 aphids at random. Treatment duration = 24 h. (2)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

0.04%

Feeding inhibition = 50.0%

1. Treatment to 50–75 aphids at random. Treatment duration = 8 h. (2)

LD50 (mice): 555 mg/kg (ipr.)

(3)

(1) Dave, K.G., Telang, S.A., and Venkataraman, K. (1962) Tetrahedron Lett., 9. (2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

MUTANGIN

695

C35H40O11 (636.69)

OAc

M.p. : 234°

O O

O

Ac O O

O OAc

(1)

(1)

SOURCE: Elaeodendron buchananii Loes., eukanda poisonous plant of E. Africa (Celastraceae)

(1)

ACTIVITY PROFILE Test Insect Chilo partellus (Swinhoe) (Spotted stem borer)

Test Method

Conc. / Dose

Efficacy

Remarks

Leaf disk test

100 µg/1.8-cm diameter disk

Feeding inhibition = 64.9%

50 µg/1.8-cm diameter disk

Feeding inhibition = 54.8%

25 µg/1.8-cm diameter disk

Feeding inhibition = 9.2%

Treatment to 3rd instar larvae prestarved for 24 h in dark. Treatment duration = 24 h. (1) Approx. EC50 = 61.0 µg/disk. Calculated from Reference 1.

(1) Tsanuo, M.K., Hassanali, A., Jondiko, I.J.O., and Torto, B. (1993) Phytochemistry, 34, 665.

© 2005 by CRC Press LLC

696

Opender Koul

MUZIGADIAL (canellal)

C15H20O3 (248.32)

M.p. : 127–128° [α]25 D : –193° (CHCl3)

CHO OH CHO

H CH2

(1, 2)

(1, 2)

SOURCE: Warburgia ugandensis Sprague, African muziga (Canellaceae)

(1,3)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (African armyworm)

Test Method Leaf disk choice test

Conc. / Dose 0.1 ppm

Efficacy Feeding inhibition = 100%

Remarks 1. Treatment to larvae. Treatment duration = 1 h. (3)

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

(1) (2) (3) (4)

Leaf disk dual-choice test

5 mM

Feeding inhibition = 82.0%

2. Treatment to larvae of 90–120 mg body weight. Treatment duration = 3 h. (4)

Kubo, I., Miura, I., Pettei, M.J., Lee, Y., Pilkiewicz, F., and Nakanishi, K. (1977) Tetrahedron Lett., 4553. El-Feraly, F.S., McPhail, A.T., Andrew, T., and Onan, K.D. (1978) Chem. Commun., 75. Nakanishi, K. and Kubo, I. (1977) Israel J. Chem., 16, 28. Gols, G.J.Z., van Loon, J.J.A.., and Messchendorp, L. (1996) Entomol. Exp. Appl., 79, 69.

© 2005 by CRC Press LLC

Insect Antifeedants

MYRCENE

697

C10H16 (136.24)

Oil B.p. : 51–51.5°/8.5 mm

(1, 2)

(2)

SOURCE: Commercial sample (Found in many essential oils)

(1)

ACTIVITY PROFILE Test Insect Hylobius pales (Herbst.) (Pales weevil)

Test Method Twig dip treatment choice assay

Conc. / Dose 10%

Efficacy

Remarks

Feeding deterrence = 40.3%

Treatment to 22 to 65 mg body weight weevils for 24 h. (1) Data calculated from Reference 1.

LD50 (rats): >5000 mg/kg (oral) (1) Salom, S.M., Carlson, J.A., Ang, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407. (2) Wrolstad, R.E. and Jennings, W.G. (1964) J. Agric. Food Chem., 12, 507. (3) Opdyke, D.L.J. (1976) Food Cosmet. Toxicol., 14, 615.

© 2005 by CRC Press LLC

(3)

698

Opender Koul

MYRICITRIN

C21H20O12 (464.38)

M.p. : 194–197°

OH OH

HO

O OH OH O OH

OH

O O OH

(1)

(1)

SOURCE: A naturally occurring compound and semisynthetic substance as well

(2)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 0.07%

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 50–75 aphids at random. Treatment duration = 24 h. (2)

(1) Hattori, S. and Hayashi, K. (1931) Acta Phytochim., 5, 213. (2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC

Insect Antifeedants

MYRICOSIDE

699

C34H44O19 (756.71) O

M.p. : 165–167°

OH

HO

O

O

OH

O O

HO

HO O

HO

H

OH

H H

O OH

O H

HO

H

HO

OH

(1)

(1)

SOURCE: Clerodendron infortunatum Gaertn., clerodendron (Verbenaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera exempta (Walker) (Nutgrass armyworm)

Test Method Leaf disk assay

Conc. / Dose 10 ppm

Efficacy Feeding inhibition = 100%

Remarks 1. Treatment to larvae at random. Activity comparable to ajugarins. (1)

(1) Cooper, R., Solomon, P.H., Kubo, I., Nakanishi, K., Shoolery, J.N., and Occolowitz, J.L. (1980) J. Am. Chem. Soc., 102, 7953.

© 2005 by CRC Press LLC

700

Opender Koul

MYRISTIC ACID

C14H28O2 (228.37)

M.p. : 54° B.p. : 250.5°/100 mm n70 D

: 1.4273

COOH

(1, 2)

(1, 2) SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae)

(3)

ACTIVITY PROFILE Test Method

Conc. / Dose

Paper towel disk assay

Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Efficacy

Remarks

0.05 mg/cm2

Feeding deterrence = 10.5% after 6 days

0.25 mg/cm2

Feeding deterrence = 59.8% after 7 days

Treatment to immature termites of 10–13 mg body weight. (3) Data calculated from Reference 3.

LD50 (mice): 43.0 ± 2.6 mg/kg (i.v.) (1) (2) (3) (4)

Merck Index (1983). Bailey, A.V. and Pittman, R.A. (1971) J. Am. Oil Chem. Soc., 48, 775. Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

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(4)

Insect Antifeedants

MYRSINAQUINONE

701

C34H50O7 (570.38)

O

H HO

O

(CH2)10

HO

O

OH

(CH2)10

No physical data given

O

(1)

(1)

SOURCE: Rapanea melanphloes (L.) Mez., East African medicinal plant (Myrsinaceae)

(1)

ACTIVITY PROFILE Test Insect Schistocerca gregaria (Forsk.) (Desert locust)

Test Method Filter paper no-choice assay

Conc. / Dose 100 µg/ml

Efficacy

Remarks

Feeding inhibition = 44.5%

Treatment to mid 5th instar females prestarved for 24 h. Treatment duration = 24 h. (1)

(1) Midiwo, J.O., Mwangi, R.W., and Ghebremeskel, Y. (1995) Insect Sci. Applic., 16, 163.

© 2005 by CRC Press LLC

702

Opender Koul

MYRSINONE

C17H26O4 (294.39)

M.p. : 120–122°

O HO

(CH2)10

HO O

(1, 2)

(1, 2)

SOURCE: Rapanea melanphloes (L.) Mez., East African medicinal plant (Myrsinaceae)

(2)

ACTIVITY PROFILE Test Insect Schistocerca gregaria (Forsk.) (Desert locust)

Test Method Filter paper no-choice assay

Conc. / Dose 100 µg/ml

Efficacy

Remarks

Feeding inhibition = 90.2%

Treatment to mid 5th instar females prestarved for 24 h. Treatment duration = 24 h. (2)

(1) Midiwo, J.O., Ghebremeskel. Y., Arot, L.M., Koyama, K., and Natori, S. (1992) Bull. Chem. Soc. Ethiop., 6, 15 (2) Midiwo, J.O., Mwangi, R.W., and Ghebremeskel, Y. (1995) Insect Sci. Applic., 16, 163.

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Insect Antifeedants

NAGILACTONE–C

703

C19H22O7 (362.37) O

M.p. : 290° (dec.) [α]D : +111° (neat)

O O

OH

HO H

O

O

(1, 2)

(1)

SOURCE: Podocarpus nagi Zoll. et Moritizi., pine (Podocarpaceae)

(2)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Efficacy

Artificial diet feeding

230 ppm

Feeding deterrence = 67.0%

Injection

25 µg/larva

Feeding deterrence = 34.0%

Remarks Treatment to 5th instar larvae for 4 days. (2)

(1) Dev, S., and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 112. (2) Zhang, M., Ying, B., and Kubo, I. (1992) J. Nat. Prod., 55, 1057.

© 2005 by CRC Press LLC

704

Opender Koul

NAGILACTONE–D

C18H20O6 (332.35)

M.p. : 265–266° (dec.) [α]D : +90° (neat)

O

O O

HO H

O

O

(1, 2)

(1)

SOURCE: Podocarpus nagi Zoll. et Moritizi., pine (Podocarpaceae)

(2)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Efficacy

Artificial diet feeding

60 ppm

Feeding deterrence = 70.0%

Injection

25 µg/larva

Feeding deterrence = 36.0%

Remarks Treatment to 5th instar larvae for 4 days. (2)

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 108. (2) Zhang, M., Ying, B., and Kubo, I. (1992) J. Nat. Prod., 55, 1057.

© 2005 by CRC Press LLC

Insect Antifeedants

1 – NAPHTHALDEHYDE

705

C11H8O (156.16)

No physical data given

CHO

(1, 2)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Pieris rapae crucivoraI (Boisd.) (Cabbage butterfly)

Test Method Leaf disk dual-choice test

Conc. / Dose 5 × 10–7 mol/cm2

Efficacy

Remarks

Feeding deterrence = 76.7%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 2 h. (1)

(1) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130.

© 2005 by CRC Press LLC

706

Opender Koul

2 – NAPHTHALDEHYDE

C11H8O (156.16)

No physical data given

CHO

(1)

(1)

SOURCE: Commercial sample

(1)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora (Boisd.) (Cabbage butterfly)

Test Method Leaf disk dual-choice test

Conc. / Dose 5 × 10–7 mol/cm2

Efficacy

Remarks

Feeding deterrence = 83.3%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 2 h. (1)

(1) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130.

© 2005 by CRC Press LLC

Insect Antifeedants

NARINGENIN

707

C15H12O5 (272.26)

[α]27 D : –22.5° (MeOH)

OH

HO

M.p. : 251° (227–228°)

O

OH

O

(1, 2)

(1, 2)

SOURCE: Semisynthetic

(1,3)

ACTIVITY PROFILE Test Insect 1. Schizaphis graminum (Rondani) (Wheat aphid)

Test Method Artificial diet feeding

Conc. / Dose 0.15%

Efficacy Feeding inhibition = 50.0%

Remarks 1. Treatment to 50–75 aphids at random. Treatment duration = 24 h. (3)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

0.25%

Feeding inhibition = 50.0%

2. Treatment to 50–75 aphids at random. Treatment duration = 8 h. (3)

(1) Gell, R.J., Pinhey, J.T., and Ritchie, E. (1958) Aust. J. Chem., 11, 372. (2) Gaffield, W. and Waiss, A.C. Jr. (1968) Chem. Commun., 29. (3) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC

708

Opender Koul

NEOABIETIC ACID

C20H30O2 (302.46)

M.p. : 173–173.5° (167–169°) [α]25 D : +161.6° (EtOH)

COOH

(1, 3, 4)

(1, 2)

SOURCE: Pinus banksiana Dougl., jack pine (Pinnaceae)

(3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Neodiprion dubiosus (Schedl.) (Brownhead jack pine sawfly)

Pine needle and twig application

1.0 mg/ml

Feeding inhibition = 67.0%

1. Treatment to 3rd or 4th instar larvae for 4 h. (3)

2. N. rugifrons (Middleton) (Redhead jack pine sawfly)

Pine needle and twig application

1.0 mg/ml

Feeding inhibition = 83.0%

2. Treatment to 3rd or 4th instar larvae for 4 h. (3)

3. N. lecontei (Fitch) (Redhead pine sawfly)

Pine needle and twig application

18.0 mg/ml

Feeding inhibition = 70.0%

3. Treatment to 3rd or 4th instar larvae for 4 h. (4)

(1) (2) (3) (4)

Harris, G.C. and Sanderson, T.F. (1948) J. Am. Chem. Soc., 70, 334, 339. Schuller, W.H. and Ray, V.L. (1961) J. Am. Chem. Soc., 83, 2563. Schuh, B.A. and Benjamin, D.M. (1984) J. Chem. Ecol., 10, 1071. Schuh, B.A. and Benjamin, D.M. (1984) J. Econ. Entomol., 77, 802.

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Insect Antifeedants

NEOADENOSTYLONE

709

C20H24O4 (328.41)

M.p. : 104–109° [α]24 D : –86° (CHCl3)

O

O

O O

(1, 2)

(1)

SOURCE: Adenostyles alliariae (Conan) Kern., grauer alpino (Asteraceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 80.0

1. Treatment given to adults.

2. Tribolium confusum (Duv.) (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 110.0 Larvae = 94.0

2. Treatment given to both adults and larvae.

3. Trogoderma granarium (Everts) (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 151.0

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (1)

(1) Harmatha, J., Samek, Z., Novotny, L., Herout, V., and Sorm, F. (1969) Collect. Czech. Chem. Commun., 34, 1739, 2793. (2) Nawrot, J., Harmatha, J., and Novotny, L. (1984) Biochem. Syst. Ecol., 12, 99.

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710

Opender Koul

NEOHESPERIDIN DHC

C28H36O15 (612.58)

M.p. : 156–158°

OH

CH2OH O

HO

O

OCH3

COCH2CH2

HO O OH

OH

O HO OH

OH

(1–4)

(1, 2)

SOURCE: Naturally occurring in grapefruit as well as a semisynthetic compound

(2, 3)

ACTIVITY PROFILE Test Insect 1. Schizaphis graminum (Rondani) (Wheat aphid)

Test Method Artificial diet feeding

Conc. / Dose 0.2%

Efficacy Feeding inhibition = 50.0%

Remarks 1. Treatment to 50–75 aphids at random. Treatment duration = 24 h. (4)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

0.2%

Feeding inhibition = 50.0%

2. Treatment to 50–75 aphids at random. Treatment duration = 8 h. (4)

(1) (2) (3) (4)

Pratter, P.J. (1981) Perfum. Flavor., 5, 12. Horowitz, R.M. and Gentili, B. (1969) J. Agric. Food Chem., 17, 696. Dubios, G.E., Crosby, G.A., Stephenson, R.A., and Wingard, R.E. Jr. (1977) J. Agric. Food Chem., 25, 763. Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

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Insect Antifeedants

NERIIFOLIN

711

C30H46O8 (534.69) O

[α]D : –49° (MeOH)

O

OH

OCH3

HO

M.p. : 214–218° (218–225°)

O

OH O

(1, 2)

(1, 2)

SOURCE: Thevetia thevetioides (HBK) K.Schum., Mexican yellow oleander (Apocynaceae)

(2, 3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Acalymma vittatum (Fab.) (Striped cucumber beetle)

Leaf disk test

0.1%

Feeding deterrence = 100% for 3 days

1. Treatment to female beetles only. (3)

2. Popillia japonica (Newman) (Japanese beetle)

Leaflet treatment

0.5%

Feeding deterrence assessed on the basis of 1 to 10% tissue loss due to feeding against 50 to 70% in controls.

2. Treatment to adult beetles. (3)

LD50 (cat): 0.2 mg/kg (ivn.) (1) Cruz, A., Garcia, I., Iriarte, J., Muchowski, J.M., and Regla, I. (1977) J. Org. Chem., 42, 3580. (2) McLaughlin, J.L., Freedman, B., Powell, R.G., and Smith, C.R. Jr. (1980) J. Econ. Entomol., 73, 398. (3) Reed, D.K., Freedman, B., and Ladd, T.L. Jr. (1982) J. Econ. Entomol., 75, 1093. (4) Voigtlaender, H.W. (1969) Arch. Pharm., 302, 538.

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(4)

712

Opender Koul

NEUROLENIN–A

C20H28O6 (364.44)

M.p. : 127–128° [α]25 D : –257.7° (CHCl3)

O O OH O CH2 O O

(1, 2)

(1, 2, 3)

SOURCE: Neurolaena lobata (L.) R.Br., golden rod (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk nochoice test

70 µg/1.5 cm2

Efficacy

Remarks

Feeding deterrence = 42.0%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 30 min only. (1)

(1) Passreiter, C.M. and Isman, M.B. (1997) Biochem. Syst. Ecol., 25, 371. (2) Passreiter, C.M., Wendisch, D., and Gondol, D. (1995) Phytochemistry, 39, 133. (3) Manchand, P.S. and Blount, J.F. (1978) J. Org. Chem., 43, 4352.

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Insect Antifeedants

NEUROLENIN–B

713

C22H30O8 (422.47) O

O

M.p. : 165–166° [α]25 D : –350° (CHCl3)

O O OH O CH2 O O

(1, 2)

(1, 2, 3)

SOURCE: Neurolaena lobata (L.) R.Br., golden rod (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk no-choice test

70 µg/1.5 cm2

Efficacy

Remarks

Feeding deterrence = 52.0%

Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 30 min only. (2)

(1) Manchand, P.S. and Blount, J.F. (1978) J. Org. Chem., 43, 4352. (2) Passreiter, C.M. and Isman, M.B. (1997) Biochem. Syst. Ecol., 25, 371. (3) Passreiter, C.M., Wendisch, D., and Gondol, D. (1995) Phytochemistry, 39, 133.

© 2005 by CRC Press LLC

714

Opender Koul

NICALBIN–A

C28H40O7 (488.62) O

M.p. : 241–243° [α]D : +37° (CHCl3)

H OH

O H O OH

OH

O

(1, 2)

(1)

SOURCE: Nicandra physaloides (L.) Gaertn. Var. albiflora, apple-of-Peru (Solanaceae)

(2)

ACTIVITY PROFILE Test Insect Epilachna varivestis (Muls.) (Mexican bean beetle)

Test Method Leaf residue test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding deterrence = 100%

0.05%

Feeding deterrence = 100%

Treatment to 4th instar larvae for 48 h. Data based on weight loss due to antifeedant effect. (2)

0.025%

Feeding deterrence = 100%

0.01%

Data calculated from Reference 2.

Feeding deterrence = 100%

(1) Kirson, I., Gottlieb, H.E., Greenberg, M., and Glotter, E. (1980) J. Chem. Res. (S), 69. (2) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197.

© 2005 by CRC Press LLC

Insect Antifeedants

NICALBIN–B

715

C28H38O6 (470.61) O

M.p. : 275–276° [α]D : +24.2° (CHCl3)

H O

O

H O

OH

O

(1, 2)

(1)

SOURCE: Nicandra physaloides (L.) Gaertn. Var. albiflora, apple-of-Peru (Solanaceae)

(2)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf residue test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding deterrence = 100%

0.05%

Feeding deterrence = 100%

Treatment to 4th instar larvae for 48 h. Data based on weight loss due to antifeedant effect. (2)

0.025%

Feeding deterrence = 80%

Data calculated from Reference 2.

(1) Kirson, I., Gottlieb, H.E., Greenberg, M., and Glotter, E. (1980) J. Chem. Res. (S), 69. (2) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197.

© 2005 by CRC Press LLC

716

Opender Koul

NICANDRENONE–1

C28H34O6 (466.57)

M.p. : 117°

H O H

O O

OH OH

O

(1, 2)

(1)

SOURCE: Physalis peruviana L., Peruvian groundcherry (Solanaceae)

(2)

ACTIVITY PROFILE Test Insect 1. Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf residue test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding deterrence = 100%

0.05%

Feeding deterrence = 100%

1. Treatment to 4th instar larvae for 48 h. Data based on weight loss due to antifeedant effect. (2) Data calculated from Reference 2.

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Styropor test

0.1%

Feeding deterrence = 44.3%

0.01%

Feeding deterrence = 16.3%

2.Treatment to larvae of 170–190 mg body weight. (3) Data calculated from Reference 3.

(1) Begley, M.J., Crombie, L., Ham, P.J., and Whiting, D.A. (1972) Chem. Commun., 1250. (2) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197. (3) Ascher, K.R.S., Nemny, N.E., Eliyahu, M., Kirson, I., Abraham, A., and Glotter, E. (1980) Experientia, 36, 998.

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Insect Antifeedants

NIMBANDIOL

717

C26H32O7 (456.53)

[α]20 D : +187.9° (CHCl3)

OCH3

O

M.p. : 121°

O

O

O HO

OH

(1, 2)

(1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Bean leaf choice assay

Conc. / Dose 0.01%

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 4th instar larvae for 24 h. Concentration = EC50 value. (2)

(1) Kraus, W. and Cramer, R. (1981) Chem. Ber., 114, 2375. (2) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC

718

Opender Koul

NIMBIN

C30H36O9 (540.61)

[α]D : +170° (CHCl3)

OCH3

O

M.p. : 205°

O

O

O H3COOC

OAc

(1, 2)

(1, 2) SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

2. Pericallia ricini (Fab.) (Tiger moth)

3. Oxya fuscovittata (Marsh.) (Grasshopper)

Test Method Leaf disk dual-choice test

Leaf disk dual-choice test

Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding deterrence = 62.9%

Treatment to 3rd instar larvae for 24 h. (3)

10 µg/cm2

Feeding deterrence = 65.8%

1 µg/cm2

Feeding deterrence = 67.5%

10 µg/cm2

Feeding deterrence = 69.8%

1 µg/cm2

Feeding deterrence = 73.8%

10 µg/cm2

Feeding deterrence = 81.8%

(1) Harris, M., Henderson, R., McCrindle, R., Overton, K.H., and Turner, D.W. (1968) Tetrahedron, 24, 1517. (2) Narayanan, C.R., Pachapurkar, R.V., Pradhan, S.K., Shah, V.R., and Narasimhan, N.S. (1964) Ind. J. Chem., 2, 108. (3) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., and Gopalakrishnan, G. (1996) J. Chem. Ecol., 22, 1453.

© 2005 by CRC Press LLC

Insect Antifeedants

NIMBINENE

719

C28H34O7 (482.57)

[α]20 D : +168° (CHCl3)

OCH3

O

M.p. : 134°

O

O

O

OAc

(1, 2)

(1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Epilachna varivestis (Mulsant) (Mexican bean beetle)

Bean leaf choice assay

Conc. / Dose 0.018%

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 4th instar larvae for 24 h. Concentration = EC50 value. (2)

(1) Kraus, W. and Cramer, R. (1981) Chem. Ber., 114, 2375. (2) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC

720

Opender Koul

NIMBOLIDIN–C

C37H50O12 (686.80)

Amorphous powder [α]23 D : +14° (MeOH)

OAc AcO H3COOC

O AcO

OCO O

(1)

(1) SOURCE: Melia toosendan Sieb. and Zucc., Chinese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Boisd.) (Southern armyworm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy

Remarks

Feeding deterrence = Threshold level

Treatment to 3rd instar larvae and visually compared for the treated and untreated leaves consumed by the larvae. (1)

(1) Nakatani, M., Zhou, J., Nakayama, N., Okamura, H., and Iwagawa, T. (1996) Phytochemistry, 41, 739.

© 2005 by CRC Press LLC

Insect Antifeedants

NIMBOLIDIN–D

721

C41H54O12 (738.87)

Amorphous powder [α]23 D : –55° (MeOH)

H3COOC

OAc

Tig O

O AcO

O Tig O

(1)

(1) SOURCE: Melia toosendan Sieb. & Zucc., Chinese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Boisd.) (Southern armyworm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy

Remarks

Feeding deterrence = Threshold level

Treatment to 3rd instar larvae and visually compared for the treated and untreated leaves consumed by the larvae. (1)

(1) Nakatani, M., Zhou, J., Nakayama, N., Okamura, H., and Iwagawa, T. (1996) Phytochemistry, 41, 739.

© 2005 by CRC Press LLC

722

Opender Koul

NIMBOLIDIN–E

C40H54O12 (726.86)

Amorphous powder [α]22 D : +4° (MeOH)

H3COOC

OAc

Tig O

O OCO

AcO O

; (1)

(1) SOURCE: Melia toosendan Sieb. and Zucc., Chinese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Boisd.) (Southern armyworm)

Test Method Leaf disk choice test

Conc. / Dose 10 µg/cm2

Efficacy

Remarks

Feeding deterrence = Threshold level

Treatment to 3rd instar larvae and visually compared for the treated and untreated leaves consumed by the larvae. (1)

(1) Nakatani, M., Zhou, J., Nakayama, N., Okamura, H., and Iwagawa, T. (1996) Phytochemistry, 41, 739.

© 2005 by CRC Press LLC

Insect Antifeedants

723

NIMBOLIDIN–F

C41H56O12 (740.89)

Amorphous powder [α]D : +4° (MeOH)

H3COOC

OAc

OCO

O AcO

O Tig O

(1)

(1) SOURCE: Melia toosendan Sieb. and Zucc., Chinese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Boisd.) (Southern armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

10 µg/cm2 (500 ppm)

Feeding deterrence = 50.0%

Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (1)

(1) Zhou, J., Minami, Y., Yagi, F., Tadera, K., and Nakatani, M. (1997) Phytochemistry, 46, 911.

© 2005 by CRC Press LLC

724

Opender Koul

NIMBOLININ–B

C35H46O10 (626.74) OH

Amorphous powder [α]20 D : –55.5° (CHCl3)

O OAc

O AcO

OOC O

(1)

(1, 2) SOURCE: Melia azedarach L., Chinaberry (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera eridania (Boisd.) (Southern armyworm)

Leaf disk choice test

1000 ppm

Feeding deterrence = Threshold level

1. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (2)

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice test

1000 ppm

Feeding deterrence = Threshold level

2. Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (2)

(1) Kraus, W. and Bokel, M. (1981) Chem. Ber., 114, 267. (2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11731.

© 2005 by CRC Press LLC

Insect Antifeedants

NOMILIN

725

C28H34O9 (514.57)

Only spectral data given

O

OAc O

O O

O O

O

(1, 2)

(1)

SOURCE: Citrus natsudaidai Hayati, Japanese citrus (Rutaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Helicoverpa zea (Boddie) (Corn earworm)

Leaf disk choice test

6.6 µg/disk

Feeding deterrence = 95.0%

1. Treatment to 3rd instar larvae for 48 h. (3)

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Leaf disk choice test

0.66 µg/disk

Feeding deterrence = 95.0%

2. Treatment to 3rd instar larvae for 48 h. (3)

3. Ostrinia nubilalis (Hubner) (European corn borer)

Leaf disk choice test

50 µg/g

Feeding deterrence = 71.0%

3. Treatment to neonate larvae for 48 h.

500 µg/g

87.0%

(4)

1387 ppm

50.0%

4475 ppm

95.0%

4. Treatment to 3rd instar larvae for 25 days. (5)

4. Reticulitermes speratus (Kolbe) (Subterranean termite)

Paper disk no-choice test

(1) Kubo, I. and Klocke, J.A. (1981) Colloques Inst. Nat. Recherches Agric., 7, 117. (2) Altieri, M.A., Lippmann, M., Schmidt, L.L., and Kubo, I. (1984) Protection Ecol., 6, 91. (3) Klocke, J.A. and Kubo, I. (1982) Entomol. Exp. Appl., 32, 299. (4) Arnason, J.T., Philogene, B.J.R., Donskov, N., and Kubo, I. (1987) Entomol. Exp. Appl., 43, 221. (5) Serit, M., Ishida, M., Hagiwara, N., Kim, M., Yamamoto, T., and Takahashi, S. (1992) J. Chem. Ecol., 18, 593.

© 2005 by CRC Press LLC

726

Opender Koul

NONADECANOIC ACID

C19H38O2 (298.51)

M.p. : 68.7° B.p. : 297–298°/100 mm

HOOC

(1, 2)

(1)

SOURCE: Synthetic (Found in many pine spp.)

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk test

Efficacy

Remarks

0.25 mg/cm2

Feeding deterrence = 79.0% after 7 days

Treatment to 10 to 13 mg body weight larvae. (2)

0.05 mg/cm2

Feeding deterrence = 39.4% after 6 days

Data calculated from Reference 2.

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC

Insect Antifeedants

NOOTKATONE

727

C15H22O (218.34)

M.p. : 36–37° [α]D : + 195.5° (CHCl3)

O

CH2

(2)

(1, 2) SOURCE: Chamaecyparis nootkatensis (D. Don.) Spach., yellow cedar (Cupressaceae) Also from grapefruit oil and juice

(1, 2)

ACTIVITY PROFILE Test Insect Coptotermes formosanus (Shiraki) (Formosan subterranean termite)

Test Method Tunneling assay choice test

Conc. / Dose 10 g/liter

Efficacy

Remarks

Feeding deterrence = 100.0%

Treatment to workers over a period of one year to investigate the longevity of the effect. Effects were similar to starvation effects. (1)

(1) Maistrello, L., Handerson, G., and Laine, R.A. (2003) Pest Manag. Sci, 59, 58. (2) MacLeod, W.D. (1965) Tetrahedron Lett., 4779.

© 2005 by CRC Press LLC

728

Opender Koul

NORDAMNACANTHAL

C15H8O5 (268.23)

O

M.p. : 220°

OH CHO

OH O

(1, 2)

(2)

SOURCE: Galium aparine L., bedstraw (Rubiaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk assay choice test

0.12 µmol/cm2

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 3rd instar larvae for 6 h. Concentration = EC50 value. (1)

(1) Morimoto, M., Tanimoto, K., Sakatani, A., and Komai, K. (2002) Phytochemistry, 60, 163. (2) Zhou, Z., Jiang, S.-H., Zhu, D.-Y., Lin, L.-Z., and Cordell, A.G. (1994) Phytochemistry, 36, 765,

© 2005 by CRC Press LLC

Insect Antifeedants

OBACUNONE

729

C26H30O7 (454.52) O

M.p. : 229–230° (209–211°) [α]D : –50° (CHCl3)

O

O O

O O

O

(1, 2)

(1, 2) SOURCE: Harrisonia abyssinica Oliv., East African shrub (Simaroubaceae) Citrus natsudaidai Hayata, Japanese citrus (Rutaceae)

(2) (3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose 100 µg/disk

Efficacy

Remarks

Feeding deterrence = 49.0 ± 13%

1. Treatment to early or mid 6th instar larvae. (2) 2. Treatment to 12–h pre-starved late 5th instar larvae. (2) 3. Treatment to late 5th instar larvae. (2)

1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Leaf disk test

2. Eldana saccharina (Walker) (Sugar cane borer)

Leaf disk test

3. Maruca testulalis (Geyer) (Bean pod borer)

Leaf disk test

4. Reticulitermes speratus (Kolbe) (Subterranean termite)

Paper disk no-choice test

5. Helicoverpa zea (Boddie) (Corn earworm)

Leaf disk choice test

6.5 µg/cm2

Feeding deterrence = 95.0%

6. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Leaf disk choice test

0.6 µg/cm2

Feeding deterrence = 95.0%

100 µg/disk 1 µg/disk

Feeding deterrence = 94.0 ± 4% 79.0 ± 9%

100 µg/disk 10 µg/disk 1 µg/disk

Feeding deterrence = 82.0 ± 9% 76.0 ± 12% 61.0 ± 9%

571 ppm 1133 ppm

Feeding deterrence = 50.0% 95.0%

4. Treatment to 3rd instar larvae based on size over 25 days. Concentrations = EC50 and EC95 respectively. (3) 5. Treatment to 3rd instar larvae for 48 h. (4) 6. Treatment to 3rd instar larvae for 48 h. (4)

(1) Kubota, T., Matsuura, T., Tokoroyama, T., Kamikawa, T., and Matsumoto, T. (1961) Tetrahedron Lett., 325. (2) Hassanali, A., Bentley, M.D., Sitayo, E.N.O., Njoroge, P.E.W., and Yatagai, M. (1986) Insect Sci. Applic., 7, 495. (3) Serit, M., Ishida, M., Hagiwara, N., Kim, M., Yamamoto, T., and Takahashi, S. (1992) J. Chem. Ecol., 18, 593. (4) Klocke, J.A. and Kubo, I. (1982) Entomol. Exp. Appl., 32, 299.

© 2005 by CRC Press LLC

730

Opender Koul

OCOTILLONE

C30H51O3 (459.74)

[α]D : + 50° (dioxane)

H OH O

O

(1, 2)

(1, 2)

SOURCE: Dysoxylum malabaricum Bedd. and ex CDC, white cidar (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dual-choice test

Conc. / Dose

Efficacy

Remarks

1 µg/cm2

Feeding deterrence = 55.5%

Treatment to 3rd instar larvae for 24 h. (2)

5 µg/cm2

Feeding deterrence = 56.8%

EC50 = 0.82 µg/cm2

10 µg/cm2

Feeding deterrence = 69.2%

Calculated from Reference 2.

50 µg/cm2

Feeding deterrence = 72.5%

(1) Govindachari, T.R., Suresh, G., and Krishna Kumari, G.N. (1994) Phytochemistry, 37, 1127. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari, G.N. (1995) J. Chem. Ecol., 21, 1586.

© 2005 by CRC Press LLC

Insect Antifeedants

1 – OCTADECENE

731

C18H36 (252.49)

M.p. : 17.5° B.p. : 144–146°/3 mm n20 D

: 1.4448

(1)

(1, 2) SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk test

0.05 mg/cm2

Efficacy

Remarks

Feeding deterrence = 7.2% after 6 days.

Treatment to 10- to 13-mg body weight larvae. (2) Data calculated from Reference 2.

(1) Niemann, C. and Wagner, C.D. (1942) J. Org. Chem., 7, 227. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC

732

Opender Koul

11 – OCTADECENOIC ACID

C18H34O2 (282.47)

M.p. : 10.5–12° (14.5–15.5°)

COOH

(1, 2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk test

0.05 mg/cm2

Efficacy

Remarks

Feeding deterrence = 11.8% after 6 days.

Treatment to 10- to 13-mg body weight larvae. (2) Data calculated from Reference 2.

(1) Ahmad, K., Bumpus, F.M., and Strong, F.M. (1948) J. Am. Chem. Soc., 70, 3391. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC

Insect Antifeedants

OCTANOIC ACID

733

C8H16O2 (144.21)

M.p. : 16° B.p. : 124°/10 mm

COOH

(1, 2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method Paper towel disk test

Conc. / Dose 0.05 mg/cm2

Efficacy

Remarks

Feeding deterrence = 12.7% after 6 days.

Treatment to 10- to 13-mg body weight larvae. (2) Data calculated from Reference 2.

LD50 (rats): 10,000 mg/kg (oral) (1) Langenbeck, W. and Richter, M. (1956) Chem. Ber., 89, 202. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. (3) Opdyke, D.L.J. (1981) Food Cosmet. Toxicol., 19, 237.

© 2005 by CRC Press LLC

(3)

734

Opender Koul

n – OCTYL GALLATE

C15H22O5 (282.34)

M.p. : 94–95°

COO

HO

OH OH

(1, 2)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

57 ppm

Feeding inhibition = 50.0%

1. Treatment to 50–75 aphids at random. Treatment duration = 24 h. (2)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

56 ppm

Feeding inhibition = 50.0%

2. Treatment to 50–75 aphids at random. Treatment duration = 8 h. (2)

3. Acyrthosiphon pisum (Harris) (Pea aphid)

Artificial diet feeding

182 ppm

Feeding inhibition = 50.0%

3. Treatment to aphids at random. (2)

(1) Van Der Kerk, G.J.M., Verbeek, J.H., and Cleton, J.C.F. (1951) Rec. Trav. Chim., 70, 277. (2) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.

© 2005 by CRC Press LLC

Insect Antifeedants

OHCHINOLIDE–C

735

C37H48O10 (652.78)

Amorphous powder [α]D : –23° (MeOH)

O O OAc

O OCO

O Tig O

(1)

(1)

SOURCE: Melia toosendan Sieb. and Zucc., Chinese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Boisd.) (Southern armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

20 µg/cm2 or 1000 ppm

Feeding deterrence = 50.0%

Treatment to 3rd instar larvae for 6 to 24 h, during which period 50% of one of the disks was consumed. (1)

(1) Zhou, J., Minami, Y., Yagi, F., Tadera, K., and Nakatani, M. (1997) Phytochemistry, 46, 911.

© 2005 by CRC Press LLC

736

Opender Koul

OLEIC ACID

C18H34O2 (262.47)

Oil B.p. : 286°/100 mm

COOH

n18 D

: 1.463

(1)

(1, 2) SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae) Hibiscus syriacus L., rose-of-sharon (Malvaceae)

(2) (3)

ACTIVITY PROFILE Test Insect 1. Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk assay

0.25 mg/cm2

Efficacy

Remarks

Feeding deterrence = 8.2% after 7 days.

1. Treatment to immature termites of 10–13 mg body weight. (2) Data calculated from Reference 2.

2. Anthonomus grandis (Bohem.) (Boll weevil)

Plate bioassay

100 µg/ feeding site

Feeding 36% of controls after 3 h and 32% after 6 h in males. Females could feed only 17 and 20% of controls, respectively

LD50 (mice): 230.0 ± 18.0 mg/kg (i.v.) (1) (2) (3) (4)

Robinson, G.M. and Robinson, R. (1925) J. Chem Soc., 175. Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) J. Chem. Ecol., 13, 1087. Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

© 2005 by CRC Press LLC

2. Treatment to adult weevils. (3)

(4)

Insect Antifeedants

ONOPORDOPICRIN

737

C19H24O6 (348.40)

M.p. : 55–56° [α]20 D : +166.8° (MeOH)

CH2

OCOC.CH2OH

CH2

CH2OH

O O

(1)

(1, 2) SOURCE: Onopordon acantium L. (Asteraceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

1. Treatment given to adults.

2. Tribolium confusum (Duv.) (Confused flour beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient: Adults = 51–100 Larvae = 51–100

2. Treatment given to both adults and larvae.

3. Trogoderma granarium (Everts) (Khapra beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 151–200

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (1)

(1) Drozdz, B., Grabarczyk, H., Samek, Z., Holub, M., Herout, V., and Sorm, F. (1968) Coll. Czech. Chem. Commun., 33, 1730; (1972) 37, 1546. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC

738

Opender Koul

OSMUNDALACTONE

C6H8O3 (128.13)

M.p. : 82–82.5° [α]22 D : –70.6° (H2O)

H HO H O

O

(1)

(1, 2) SOURCE: Osmunda japonica Thunb., flowering fern (Osmundaceae)

(2)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina (DelOrza) (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose 0.39%

Efficacy Feeding ratio = 13.0% (strong feeding inhibition)

Remarks Treatment to 5th instar larvae after 4 h of pre-starvation. (2)

(1) Hollenbeak, K.H. and Kuehne, M.E. (1974) Tetrahedron, 30, 2307. (2) Numata, A., Hokimoto, K., Takemura, T., and Fukui, S. (1983) Appl. Ent. Zool., 18, 129.

© 2005 by CRC Press LLC

Insect Antifeedants

O-OXALYLHOMOSERINE

739

C6H9O6N (191.14)

O

O

HO

O

Only spectral data given

NH2

HO

O

(1, 2)

(1)

SOURCE: Lathyrus latifolius L., everlasting pea (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Glass fiber disk test

Conc. / Dose

Efficacy

Remarks

0.125%

Feeding deterrence = 53.0%

0.25%

Feeding deterrence = 58.0%

Final stadium larvae treatment pre-starved for 4 h. Treatment given until 50% of the disk was consumed or 18 h, whichever came first. (2)

(1) Murooka, Y. and Harada, T. (1967) Agric. Biol. Chem., 31, 1035. (2) Bell, E.A., Perera, K.P.W.C., Nunn, P.B., Simmonds, M.S.J., and Blaney, W.M. (1996) Phytochemistry, 43, 1003.

© 2005 by CRC Press LLC

740

Opender Koul

2-OXO-3,13E-CLERODIEN-15-OIC ACID

C20H32O3 (320.47)

Oil

COOH O

(1, 2)

(1, 2)

SOURCE: Detarium microcarpum Guill. & Perr., African atokolo (Caesalpiniaceae)

(1)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe. (Subterranean termite)

Test Method Paper disk choice bioassay

Conc. / Dose 80 µg/cm2

Efficacy Feeding deterrence index = 5

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index below 20 highly deterrent. (1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1101. (2) Aquino, R., Ciavatla, M.L., DeTomassi, N., and Gacs-Baitz, E. (1992) Phytochemistry, 31, 1823.

© 2005 by CRC Press LLC

Insect Antifeedants

18-OXO-3,13E-CLERODIEN-15-OIC ACID

741

C20H30O3 (318.46)

Oil [α]D : + 7° (CHCl3)

COOH

CHO

(1)

(1)

SOURCE: Detarium microcarpum Guill. & Perr., African atokolo (Caesalpiniaceae)

(1)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe. (Subterranean termite)

Test Method Paper disk choice bioassay

Conc. / Dose 80 µg/cm2

Efficacy Feeding deterrence index = 5

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1101.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index below 20 highly deterrent. (1)

742

Opender Koul

3-OXOGRANDOLIDE

C15H20O4 (264.32)

M.p. : 143–144° [α]24 D : +50° (CHCl3)

CH2 OH

H

O

H

O

O

(1, 2)

(1)

SOURCE: Arctotis grandis Thunb., African daisy (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 67.3

1. Treatment given to adults.

2. Tribolium confusum (Duv.) (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient Adults = 102.7 Larvae = 99

2. Treatment given to both adults and larvae.

3. Trogoderma granarium (Everts) (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 88.4

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (1)

(1) Holub, M., Samek, Z., Le, V.N.P., Grabarczyk, H., and Drozdz, B. (1979) Conf. on Isoprenoids, Torun., p. 66. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk. Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC

Insect Antifeedants

5-OXO-1-(4-HYDROXY-3-METHOXY PHENYL)-DECAN-3-ONE

743

C17H24O4 (292.38)

Only spectral data given

O

O H3CO

HO

(1, 2)

(1, 2)

SOURCE: Aframomum melegueta (Roscoe) K. Schum., Cameroon cardamom (Zingiberaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Reticulitermes speratus Kolbe. (Subterranean termite)

Test Method Paper disk choice bioassay

Conc. / Dose

Efficacy

7500 ppm

Feeding deterrence index = 8.4

1000 ppm

Feeding deterrence index = 27.3

(1) Endo, K., Kanno, E., and Oshima, Y. (1990) Phytochemistry, 29, 797. (2) Escoubas, P., Lajide, L., and Mizutani, J. (1995) Phytochemistry, 40, 1097.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index below 20 highly deterrent. (2)

744

Opender Koul

15-OXO-(−)-KAUR-16-EN-19-OIC ACID

C20H28O3 (316.44) M.p. : 211–213° [α]20 D : –169° (MeOH) CH2

O COOH

(1, 2)

(1, 2) SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Reticulitermes speratus (Kolbe.) (Subterranean termite)

Test Method Paper disk choice bioassay

Conc. / Dose

Efficacy

5000 ppm

Feeding deterrence index = 0

2500 ppm

Feeding deterrence index = 14.1

(1) Murakami, T. (1981) Chem. Pharm. Bull., 29, 657. (2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC

Remarks Treatment to 3rd instar workers. Feeding duration = 14 days. Antifeedant index below 20 highly deterrent. (2)

Insect Antifeedants

PALMITIC ACID

745

C16H32O2 (256.43) M.p. : 62.5° (63–64°) B.p. : 268.5°/100 mm COOH

(1, 3)

(1, 2)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae)

(3)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk test

Efficacy

Remarks

0.25 mg/cm2

Feeding inhibition = 81.9%

Treatment to larvae of 10 to 13 mg body weight. Treatment duration = 7 days.

0.05 mg/cm2

Feeding inhibition = 33.2%

Treatment to larvae of 10 to 13 mg body weight. Treatment duration = 6 days. (3) Data calculated from Reference 3.

LD50 (mouse): 57 mg/kg (ivn.) (1) (2) (3) (4)

Bhattacharyya, S.C., Chakravarty, K.K., and Kumar, V. (1959) Chem & Indus., 1352. Kincl, F.A., Romo, J., Rosemkranz, G., and Sondheimer, F. (1956) J. Chem. Soc., 4163. Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

© 2005 by CRC Press LLC

(4)

746

Opender Koul

PALUSTRIC ACID

C20H30O2 (302.46)

M.p. : 162–167° [α]D : +71.6° (EtOH)

COOH

(1, 2)

(1, 2, 3) SOURCE: Pinus banksiana Lamb., jack pine (Pinaceae)

(3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Neodiprion dubiosus Schedl. (Brownhead jack pine sawfly)

Needles and twig application

2. N. rugifrons Midd. (Redhead jackpine sawfly)

3. N. lecontei (Fitch) (Redhead pine sawfly)

Test Insect

(1) (2) (3) (4)

Efficacy

Remarks

1.0 mg/ml

Feeding inhibition = 78.0%

1. Treatment to 3rd or 4th instar. Treatment duration = 4 h. (3)

Needles and twig application

1.0 mg/ml

Feeding inhibition = 99.0%

2. Treatment to 3rd or 4th instar. Treatment duration = 4 h. (3)

Needles and twig application

10.3 mg/ml

Feeding inhibition = >70.0 %

3. Treatment to 3rd or 4th instar larvae. Treatment duration = 4 h. (4)

Loeblich, V.M., Baldwin, D.E., and Lawrence, R.V. (1955) J. Am. Chem. Soc., 77, 2823. Schuller, W.H., Moore, R.N., and Lawrence, R.V. (1960) J. Am. Chem. Soc., 82, 1734. Schuh, B.A. and Benjamin, D.M. (1984) J. Chem. Ecol., 10, 1071. Schuh, B.A. and Benjamin, D.M. (1984) J. Econ. Entomol., 77, 802.

© 2005 by CRC Press LLC

Insect Antifeedants

PAPAVERINE

747

C20H21O4N (339.39)

M.p. : 146.5–147.5°

OCH3 OCH3

H3CO N

H3CO

(1, 2)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Phormia regina (Meigen) (Blow fly)

Test Method Sucrose solution feeding

Conc. / Dose 10 mM

Efficacy

Remarks

Feeding inhibition = 75.0%

Treatment to 2-, 4-, and 6-day-old adults, pre-starved for 24 h. Treatment duration = 6 and 24 h, respectively. (2)

Feeding inhibition = 81.0%

LD50 (rats): 750 mg/kg (oral) (1) Guthrie, D.A., Frank, A.W., and Purves, C.B. (1955) Can. J. Chem., 33, 729. (2) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299. (3) Merck Index (1983), p. 6881.

© 2005 by CRC Press LLC

(3)

748

Opender Koul

PARTHENIN

C15H18O4 (262.31)

M.p. : 163–166° [α]25 D : +7.02° (CHCl3)

HO

O

CH2

O

O

(1)

(1) SOURCE: Parthenium heterophorus L., carrot grass (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Dysdercus koenigii (Fab.) (Red cotton bug)

Oral sucrose solution feeding

0.01%

Feeding inhibition = 100%

1. Treatment to adults. Treatment duration = 24 h. (2)

2. Callosobruchus chinensis (L.) (Pulse beetle)

Oral sucrose solution feeding

0.01%

Feeding inhibition = 25.7%

0.03%

Feeding inhibition = 76.1%

2. Treatment to adults. Antifeedance calculated from Reference 2. (2)

0.04%

Feeding inhibition = 69.9 %

LD50 (rats): 42 mg/kg (ipr)

(3)

(1) Herz, W., Watanabe, H., Miyazaki, M., and Kishida, Y. (1962) J. Am. Chem. Soc., 84, 2601. (2) Sharma, R.N. and Joshi, V.N. (1977) Biovigyanum, 3, 225. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

PARTHENOLIDE

749

C15H20O3 (248.32)

M.p. : 116.5–117° [α]20 D : –81.4° (CHCl3)

CH2 O O O

(1, 2)

(1)

SOURCE: Chrysanthemum parthenium Bernh., fever few (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 148

1. Treatment given to adults.

2. Tribolium confusum (Duv.) (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient: Adults = 165.0 Larvae = 150.0

2. Treatment given to both adults and larvae.

3. Trogoderma granarium (Everts) (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 148.0

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (2)

4. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk no-choice assay

70 µg/1.5 cm2

Feeding deterrence = 77.7%

4. Treatment to 5th instar pre-starved for 3 h. Treatment duration = 30 min (3)

(1) Hendriks, H., Anderson-Wildeboer, Y., Engels, G., Bos, R., and Woerdenberg, H.J. (1997) Planta Medica, 63, 356. (2) Nawrot, J., Harmatha, J., and Bloszyk, E. (1986) In E. Donahaye and S. Navarro (eds.), Proc. 4th Int. Work. Conf. Stored Product Protection, Tel Aviv, Israel, pp. 591–597. (3) Passreiter, C.M. and Isman, M.B. (1997) Biochem. Syst. Ecol., 25, 371.

© 2005 by CRC Press LLC

750

Opender Koul

PEDONIN

C27H32O9 (500.54)

M.p. : 259–261°

O

O

OH

COOCH3 O O O

O

(1)

(1)

SOURCE: Harrisonia abyssinica Oliv., African harrisonia shrub (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Eldana saccharina (Walker) (Sugar cane borer)

2. Maruca testulalis (Geyer) (Bean pod borer)

Test Method

Conc. / Dose

Efficacy Potent antifeedant activity recorded against these two species.

Remarks No quantitative data has been reported.

Compound found to be inactive against the armyworm, Spodoptera exempta (Walker). (1)

(1) Hassanali, A., Bentley, M.D., Salwin, A.M.Z., Williams, D.J., Shephard, R.N., and Chapya, A.W. (1987) Phytochemistry, 26, 573.

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Insect Antifeedants

HO

PEDUNCULAGIN

C34H24O22 (784.55)

OH

O OH

H

OH

751

O

[α]25 D : +106° (MeOH)

OH

O

Amorphous sandy soil

O OH O

H

O

H O

O

OH

O OH

OH HO

OH OH OH

(1, 2)

(1, 3)

SOURCE: Casuarina stricta Aiton., drooping she-oak (Casuarinaceae); Stachyurus praecox Sieb. & Zucc., spiketail (Stachyuraceae), and many other species

(1, 2)

ACTIVITY PROFILE Test Insect 1. Schizaphis graminum (Rondani) (Wheat aphid)

Test Method Artificial diet feeding

Conc. / Dose 182 ppm

Efficacy Feeding inhibition = 50%

Remarks 1. Treatment to aphids at random. Concentration = EC50 (3)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

261 ppm

Feeding inhibition = 50%

2. Treatment to aphids at random. Concentration = EC50 (3)

(1) Schmidt, O.T., Wuertele, L., and Harreus, A. (1965) Ann. Chem., 690, 150 (2) Ishimatsu, M., Tanaka, T., Nonaka, G., and Nishioka, I. (1989) Phytochemistry, 28, 3179. (3) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.

© 2005 by CRC Press LLC

752

Opender Koul

PEPEROMIN–A

C22H22O8 (414.41) O

O

M.p. : 145–146° [α]27 D : +20.6° (CHCl3)

O O H3CO H

H3CO

O O

(1, 2)

(1, 2, 3)

SOURCE: Peperomia dindigulensis Miq., Indian endemic pepper (Piperaceae) P. japonica, Japanese pepper (Piperaceae)

(2) (1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk test

47.15 µg/cm2

Feeding inhibition index = 50.0%

1. Treatment to larvae. Concentration = FI50 value.

2. Rhaphidopalpa foveicollis (Lucas) (Red leaf beetle)

Leaf disk test

36.20 µg/cm2

Feeding inhibition index = 50.0%

2. Treatment to larvae. Concentration = FI50 value.

3. Atractomorpha crenulata (Fab.) (Tobacco grasshopper)

Leaf disk test

42.17 µg/cm2

Feeding inhibition index = 50.0%

3. Treatment to larvae. Concentration = FI50 value. (2)

Test Insect

Efficacy

Remarks

(1) Chen, C., Jan, F., Chen, M., and Lee, T. (1989) Heterocycles, 29, 411. (2) Govindachari, T.R., Krishna Kumari, G.N., and Partho, P.D. (1998) Phytochemistry, 49, 2129. (3) Delle Monache, F. and Compagnone, R.S. (1996) Phytochemistry, 43, 1097.

© 2005 by CRC Press LLC

Insect Antifeedants

PEPEROMIN–B

753

C23H26O8 (430.45) H3CO

O

M.p. : 143–145° [α]27 D : +28.9° (CHCl3)

H3CO O H3CO H

H3CO

O O

(1, 2)

(1, 2, 3)

SOURCE: Peperomia dindigulensis Miq., Indian endemic pepper (Piperaceae) P. japonica, Japanese pepper (Piperaceae)

(2) (1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk test

54.67 µg/cm2

Feeding inhibition index = 50.0%

1. Treatment to larvae. Concentration = FI50 value.

2. Rhaphidopalpa foveicollis (Lucas) (Red leaf beetle)

Leaf disk test

37.70 µg/cm2

Feeding inhibition index = 50.0%

2. Treatment to larvae. Concentration = FI50 value.

3. Atractomorpha crenulata (Fab.) (Tobacco grasshopper)

Leaf disk test

35.00 µg/cm2

Feeding inhibition index = 50.0%

3. Treatment to larvae. Concentration = FI50 value. (2)

Test Insect

Efficacy

Remarks

(1) Chen, C., Jan, F., Chen, M., and Lee, T. (1989) Heterocycles, 29, 411. (2) Govindachari, T.R., Krishna Kumari, G.N., and Partho, P.D. (1998) Phytochemistry, 49, 2129. (3) Delle Monache, F. and Compagnone, R.S. (1996) Phytochemistry, 43, 1097.

© 2005 by CRC Press LLC

754

Opender Koul

PEPEROMIN–E

C22H20O8 (412.12)

O

M.p. : 140°

O

O

[α]D : +2.7° (CHCl3) H 2C O

H3CO H

H3CO

O O

(1)

(1)

SOURCE: Peperomia dindigulensis Miq., Indian endemic pepper (Piperaceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk test

33.01 µg/cm2

Feeding inhibition index = 50.0%

1. Treatment to larvae. Concentration = FI50 value.

2. Rhaphidopalpa foveicollis (Lucas) (Red leaf beetle)

Leaf disk test

25.90 µg/cm2

Feeding inhibition index = 50.0%

2. Treatment to larvae. Concentration = FI50 value.

3. Atractomorpha crenulata (Fab.) (Tobacco grasshopper)

Leaf disk test

24.90 µg/cm2

Feeding inhibition index = 50.0%

3. Treatment to larvae. Concentration = FI50 value. (1)

Test Insect

Efficacy

Remarks

(1) Govindachari, T.R., Krishna Kumari, G.N., and Partho, P.D. (1998) Phytochemistry, 49, 2129.

© 2005 by CRC Press LLC

Insect Antifeedants

PERAMINE

755

C12H17ON5 (247.30)

M.p. : 242–243° (HBr)

O N N

NH

N H

NH2

(1, 2)

(3)

SOURCE: Lolium perenne L., ryegrass infected by an endophytic fungus Acremonium loliae Latch.

(2)

ACTIVITY PROFILE Test Insect Listronotus bonariensis (Kuschel) (Argentine stem weevil)

Test Method Artificial diet feeding

Conc. / Dose 1.3 ppm

Efficacy Threshold feeding inhibition level

Remarks Treatment to adults. (2)

(1) Rowan, D.D., Hunt, M.B., and Gaynor, D.L. (1986) J. Chem. Soc. Chem. Commun., 935. (2) Rowan, D.D. and Gaynor, D.L. (1986) J. Chem. Ecol., 12, 647. (3) Rowan, D.D. and Tapper, B.A. (1989) J. Nat. Prod., 52, 193.

© 2005 by CRC Press LLC

756

Opender Koul

(–) PERGULARININE (tylophorinine)

C23H25O4N (379.46)

H3CO

M.p. : 233–235° (dec.) (248–249°)

HO

[α]25 D : –16° (CHCl3)

H

N

H3CO OCH3

(1)

(1) SOURCE: Tylophora asthmatica Wight and Arn., tylophora (Asclepiadaceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Artificial diet feeding

Conc. / Dose 12.0 ppm

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to larvae of 60- to 70-mg body weight pre-starved for 4 h. (2)

(1) Mulchandani, N.B. and Venkatachalam, S.R. (1976) Phytochemistry, 15, 1561. (2) Verma, G.S., Ramakrishna, V., Mulchandani, N.B., and Chadha, M.S. (1986) Entomol. Exp. Appl., 40, 99.

© 2005 by CRC Press LLC

Insect Antifeedants

PERLOLINE

757

C20H17O3N2 (333.37)

Only spectral data given

NH

O N

OCH3 OCH3

(1)

(1)

SOURCE: Lolium perenne L., perennial rye grass (Gramineae)

(1)

ACTIVITY PROFILE Test Insect Locusta migratoria (L.) (Migratory locust)

Test Method

Conc. / Dose

Remarks Treatment at random. (2)

Wafer test

0.25%

Feeding inhibition = 76.0%

Leaf test

0.25%

Feeding inhibition = 25.0%

(1) Jeffreys, J.A.D. (1964) J. Chem. Soc., 4504. (2) Bernays, E.A. and Chapman, R.F. (1977) Ecol. Entomol., 2, 1.

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Efficacy

758

Opender Koul

PETASITOLIDE–B

C20H28O4 (332.44)

M.p. : 146° [α]20 D : +31.8° (CHCl3)

H O

O

O O

(1)

(1, 2) SOURCE: Petasites hybridus (L.) Gaertn., butter dock (Asteraceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 128

1. Treatment given to adults.

2. Tribolium confusum (Duv.) (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient: Adults = 98.0 Larvae = 85.0

2. Treatment given to both adults and larvae.

3. Trogoderma granarium (Everts) (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 106.0

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Novotny, L., Herout, V., and Sorm, F. (1961) Tetrahedron Lett., 697. (2) Nawrot, J., Harmatha, J., and Novotny, L. (1984) Biochem. Syst. Ecol., 12, 99.

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Insect Antifeedants

PEUCEDANIN

759

C15H14O4 (258.27)

M.p. : 109°

H3CO

O

O

O

(1, 2, 3)

(1, 2)

SOURCE: Peucedanum officinale L., brim stone-wort (Apiaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Efficacy

Remarks

Leaf disk test

1000 ppm

Feeding ratio = 12%

Treatment to 3rd instar larvae. Ratio of 0–20% strong inhibitory activity. (3)

(1) Spath, E. and Klajer, K. (1933) Ber, 66, 749. (2) Spath, E., Klajer, K., and Schlosser, C. (1931) Ber., 64, 2203. (3) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC

760

Opender Koul

(–) PHASEOLIN

C20H18O4 (322.36)

M.p. : 177–178° [α]D : –145° (EtOH)

HO

O

O O

(1, 2)

(1) SOURCE: Phaseolus vulgaris L., kidney bean (Fabaceae)

(2)

ACTIVITY PROFILE Test Insect 1. Costelytra zealandica (White) (Scarab beetle)

2. Heteronychus arator (Fab.) (Black beetle)

Test Method

Conc. / Dose

Synthetic diet feeding

Synthetic diet feeding

Efficacy

Remarks

1 µg/ml to 100 µg/ml

Feeding deterrence = 100%

1. Treatment to 3rd instar larvae after 24-h pre-starvation. (2)

0.03 µg/g

Feeding deterrence = 50.0%

Treatment to 24-h pre-starved 3rd instar larvae. (3)

200 µg/ml

Feeding deterrence = 100%

2. Treatment to 3rd instar larvae after 24-h pre-starvation.

100 µg/ml

Feeding deterrence = 36.1%

10 µg/ml

Feeding deterrence = 33.3%

Data calculated from Reference 2. (2)

(1) Perrin, D.R. (1964) Tetrahedron Lett., 29. (2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73. (3) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) J. Chem. Ecol., 11, 1713.

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Insect Antifeedants

(–) PHASEOLLIDIN

HO

761

C20H20O4 (324.38) O

M.p. : 67–69° [α]D : –150 to –250°

O OH

(1, 2)

(1)

SOURCE: Phaseolus vulgaris L., kidney bean (Fabaceae)

(2)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Synthetic diet feeding

Conc. / Dose 1.6 µg/g

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 3rd instar larvae after 24-h pre-starvation. Concentration = EC50 value. (2)

(1) Perrin, D.R., Whittle, C.P., and Batterham, T.J. (1972) Tetrahedron Lett., 1673. (2) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC

762

Opender Koul

(–) PHASEOLLINISOFLAVAN

HO

C20H20O4 (324.38)

[α]D : –9° (MeOH)

O

O

HO

(1)

(1, 2) SOURCE: Phaseolus vulgaris L., kidney bean (Fabaceae)

(2)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Synthetic diet feeding

Conc. / Dose

Efficacy

Remarks

10.0 µg/g

Feeding deterrence = 100.0%

1.0 µg/g

Feeding deterrence = 100.0%

Treatment to 3rd instar larvae after 24-h pre-starvation. Data calculated from Reference 2. (2)

0.02 µg/g

Feeding deterrence = 50.0%

Treatment to 3rd instar larvae after 24-h pre-starvation. Concentration = EC50 value. (3)

(1) Burden, R.S., Bailey, J.A., and Dawson, G.W. (1972) Tetrahedron Lett., 4175. (2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73. (3) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC

Insect Antifeedants

PHELLOPTERIN

763

C17H16O5 (300.31)

M.p. : 102°

OCH3

O

O

O

O

(1, 2)

(1)

SOURCE: Angelica silvestris L., angelica (Apiaceae)

(2)

ACTIVITY PROFILE Test Insect Peridroma saucia (Hubner) (Variegated cutworm)

Test Method

Conc. / Dose

Leaf disk choice test

Efficacy

Remarks

14.25 µg/cm2

Feeding deterrence = 45.4%

Treatment to 5th instar larvae for 5 h. (2)

28.5 µg/cm2

Feeding deterrence = 58.7%

57.0 µg/cm2

Feeding deterrence = 87.5%

(1) Chaterjee, A., Bose, P.K., and Saha, S.K. (1962) Arch. Pharm., 295, 248. (2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.

© 2005 by CRC Press LLC

FI50 = 18.2 µg/cm2 Calculated from Reference 2.

764

Opender Koul

PHENANTHRIDINE

C13H10N (180.22)

No physical data given

N

(1)

(1)

SOURCE: Commercial sample

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy Feeding deterrence index = 12.01

Remarks Treatment to 4-d-old larvae for 1 day. Antifeedant index value below 20 highly deterrent. (1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1993) J. Agric. Food Chem., 41, 2426.

© 2005 by CRC Press LLC

Insect Antifeedants

765

C8H11NHCl (121.18)

PHENETHYLAMINE HYDROCHLORIDE

M.p. : 159–160°

NH2 - HCl

(1)

(1)

SOURCE: Commercial sample

(1)

ACTIVITY PROFILE Test Insect 1. Nilaparvata lugens (Stal.) (Brown planthopper)

Test Method Sucrose solution sucking method

Conc. / Dose

Efficacy

Remarks Treatment to adult females. FI50 = 54.31 ppm

1000 ppm 500 ppm 50 ppm

Feeding deterrence = 90.0% 75.0% 51.0%

2. Sogatella furcifera (Horvath) (Planthopper)

1000 ppm 100 ppm 10 ppm

94.0% 71.0% 55.0%

FI50 = 38.72 ppm

3. Laodelphax striatella (Fallen) (Planthopper)

1000 ppm 100 ppm 10 ppm

76.0% 53.0% 41.0%

FI50 = 151.24 ppm

4. Nephotettix cincticeps (Uhler) (Fruit leaf hopper)

1000 ppm 100 ppm 10 ppm

97.0% 77.0% 47.0%

FI50 = 71.32 ppm

Calculated from Reference 1. (1)

(1) Kurata, S. and Sogawa, K. (1976) Appl. Ent. Zool., 11, 89.

© 2005 by CRC Press LLC

766

Opender Koul

PHENOL

C6H6O (94.11)

B.p. : 68–71°/0.5 mm n25 D : 1.5210

OH

(1)

(1, 2)

SOURCE: Naturally occurring in number of essential oils and resins

(1, 2)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk test

Conc. / Dose 0.5%

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to adult beetles and inhibition achieved in 3 h. (1)

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378. (2) Karrer, W. (1958) Konstitution und Vorkommen der Organischen Pflanzenstoffe, Vol. 1, Berkhauser Verlag, Basel, p. 72.

© 2005 by CRC Press LLC

Insect Antifeedants

1-PHENYL-4-(2-O-ALKYL-BENZOYL) PYRAZOLE–A

767

C20H18O4N2 (350.37)

M.p. : 105°

O COOC2H5 O

N

N

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding deterrence = 100% after 8 h

Treatment to larvae. (1)

Feeding deterrence = 75.0% after 24 h

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC

768

Opender Koul

1-PHENYL-4-(2-O-ALKYL-BENZOYL) PYRAZOLE–B

C21H20O4N2 (364.40)

M.p. : 118°

O COOC2H5 O

N

N

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding deterrence = 100% after 24 h

Treatment to larvae. Very active compound. (1)

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC

Insect Antifeedants

1-PHENYL-4-(2-O-ALKYL-BENZOYL) PYRAZOLE–C

769

C20H17O4N2Cl (384.82)

M.p. : 120°

O COOC2H5 O

Cl

N

N

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding deterrence = 100% after 24 h

Treatment to larvae. Very active compound. (1)

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC

770

Opender Koul

1-PHENYL-4-(2-O-ALKYL-BENZOYL) PYRAZOLE–D

C20H17O4N2Br (384.82)

M.p. : 111°

O COOC2H5 O

Br

N

N

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding deterrence = 100% after 4 h but followed by considerable reduction in activity

Treatment to larvae.

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC

Activity poor. (1)

Insect Antifeedants

1-PHENYL-4-(2-O-ALKYL-BENZOYL) PYRAZOLE–E

771

C22H22O4N2 (378.43)

M.p. : 114°

O COOC2H5 O

N

N

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding deterrence = 100% up to 8 h and subsequently reduced to 75.0% by 24 h

Treatment to larvae.

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC

Moderate activity. (1)

772

Opender Koul

1-PHENYL-1-BUTYNE

C10H10 (130.19)

B.p. : 201–203° n18 D : 1.537

(1, 2, 3)

(1, 2)

SOURCE: Commercial sample (purified)

(3)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora (Boisd.) (Cabbage butterfly)

Test Method

Conc. / Dose

Leaf disk test

10–1 mol/l

(1) Truchet, R. (1931) Ann. Chim., 16, 397. (2) Bergmann, E. and Bondi, A. (1933) Ber., 66, 286. (3) Yano, K. (1986) Insect Biochem., 16, 717.

© 2005 by CRC Press LLC

Efficacy

Remarks

Feeding inhibition = 83.0%

Treatment to 5th instar larvae for 24 h. (3)

Insect Antifeedants

1-PHENYL-1-ETHYNE

773

C8H6 (102.14)

Only spectral data given

CH

(1) SOURCE: Commercial sample (purified)

(1)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora (Boisd.) (Cabbage butterfly)

Test Method

Conc. / Dose

Leaf disk test

10–1 mol/l

Efficacy Feeding inhibition = 64.0% after 2 h

Remarks Treatment to 5th instar larvae. (1)

(1) Yano, K. (1986) Insect Biochem., 16, 717.

© 2005 by CRC Press LLC

774

Opender Koul

1-PHENYL-1-HEXYNE

C12H14 (158.24)

Only spectral data given

(1) SOURCE: Commercial sample (purified)

(1)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora (Boisd.) (Cabbage butterfly)

Test Method

Conc. / Dose

Leaf disk test

10–1 mol/l

Efficacy Feeding inhibition = 51.0% after 2 h

Remarks Treatment to 5th instar larvae. (1)

(1) Yano, K. (1986) Insect Biochem., 16, 717.

© 2005 by CRC Press LLC

Insect Antifeedants

1-PHENYL-2,4-PENTADIYNE

775

C11H8 (140.18)

B.p. : 45–50°/.001 mm

H

(1, 2)

(1)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora (Boisd.) (Cabbage butterfly)

Test Method

Conc. / Dose

Leaf disk test

0.3 mg per 2 cm diameter disk

(1) Bohlman, F. and Kleine, K.-M. (1962) Chem. Ber., 95, 39. (2) Yano, K. (1983) J. Agric. Food Chem., 31, 667.

© 2005 by CRC Press LLC

Efficacy Feeding inhibition = 100% after 24-h exposure

Remarks Treatment to 5th instar larvae. (2)

776

Opender Koul

1-PHENYL-1-PENTYNE

C11H12 (144.22)

Only spectral data given

(1)

(1)

SOURCE: Commercial sample (purified)

(1)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora (Boisd.) (Cabbage butterfly)

Test Method

Conc. / Dose

Leaf disk test

10–1 mol/l

Efficacy Feeding inhibition = 80.0% after 2 h

Remarks Treatment to 5th instar larvae. (1)

(1) Yano, K. (1986) Insect Biochem., 16, 717.

© 2005 by CRC Press LLC

Insect Antifeedants

PHENYL PROPANOID

777

C23H30O7 (418.49)

OCH3 OH

M.p. : 65.5–66.5°

H3CO

O

OCH3

OCH3

H3CO

CH2

(1)

(1)

SOURCE: Myristica fragrans Houtt., nutmeg (Myristicaceae)

(1)

ACTIVITY PROFILE Test Insect Bombyx mori (L.) (Silkworm)

Test Method Artificial diet feeding

Conc. / Dose 50.0 ppm

Efficacy Feeding inhibition = 100% resulting in inhibition of growth

Remarks Treatment to 4th instar larvae.

(1) Isogai, A., Murakoshi, S., Suzuki, A., and Tamura, S. (1973) Agric. Biol. Chem., 37, 889.

© 2005 by CRC Press LLC

(2)

778

Opender Koul

1-PHENYL-1-PROPYNE

C9H8 (116.16)

B.p. : 182–183° n18 D

: 1.561

(1, 2, 3)

(1, 2)

SOURCE: Commercial sample (purified)

(3)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora (Boisd.) (Cabbage butterfly)

Test Method

Conc. / Dose

Leaf disk test

10–1 mol/l

Efficacy Feeding inhibition = 96.0% after 2 h

Remarks Treatment to 5th instar larvae. (3)

(1) Wohl, A. and Jaschinowski, K. (1921) Ber., 54, 476. (2) Truchet, R. (1931) Ann. Chim., 16, 309. (3) Yano, K. (1986) Insect Biochem., 16, 717.

© 2005 by CRC Press LLC

Insect Antifeedants

3-(1-PHENYL-1H-PYRAZOL-4YL) BENZOFURAN-2-CARBOXYLIC ACID–A

O

779

C18H12O3N2 (304.31)

M.p. : 236°

COOH

N N

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding deterrence = 100% up to 8 h and subsequently reduced to 75.0% by 24 h

Treatment to larvae.

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC

Moderate activity. (1)

780

Opender Koul

3-(1-PHENYL-1H-PYRAZOL-4YL) BENZOFURAN-2-CARBOXYLIC ACID–B

O

C19H14O3N2 (318.33)

M.p. : 210°

COOH

N N

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding deterrence = 100% up to 24 h

Treatment to larvae. High activity. (1)

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC

Insect Antifeedants

3-(1-PHENYL-1H-PYRAZOL-4YL) BENZOFURAN-2-CARBOXYLIC ACID–C

O

781

C18H11O3N2Cl (338.75)

M.p. : 215°

COOH

Cl

N N

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding deterrence = 100% up to 24 h

Treatment to larvae. High activity. (1)

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC

782

Opender Koul

3-(1-PHENYL-1H-PYRAZOL-4YL) BENZOFURAN-2-CARBOXYLIC ACID–D

O

C18H11O3N2Br (383.20)

M.p. : 223°

COOH

Br N N

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding deterrence = 100% up to 8 h and subsequently reduced to 75.0% by 24 h

Treatment to larvae.

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC

Moderate activity. (1)

Insect Antifeedants

3-(1-PHENYL-1H-PYRAZOL-4YL) BENZOFURAN-2-CARBOXYLIC ACID–E

O

783

C20H16O3N2 (332.36)

M.p. : 213°

COOH

N N

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding deterrence = 100% up to 8 h and subsequently reduced to 75.0% by 24 h

Treatment to larvae.

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC

Moderate activity. (1)

784

Opender Koul

PHLORETIN

C15H14O5 (274.27)

M.p. : 262° (dec.)

OH

OH

HO

OH

O

(1)

(1)

SOURCE: Naturally occurring flavonoid in grasses and apple trees

(1)

ACTIVITY PROFILE Test Insect 1. Schizaphis graminum (Rondani) (Wheat aphid)

Test Method Artificial diet feeding

Conc. / Dose 0.04%

Efficacy Feeding inhibition = 50%

Remarks 1. Treatment to 50–75 aphids at random for 24 h. Concentration = EC50 (2)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

0.14%

Feeding inhibition = 50%

2. Treatment to 50–75 aphids at random for 8 h. Concentration = EC50 (2)

(1) Seshadri, T.R. (1951) Ann. Rev. Biochem., 20, 495. (2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC

Insect Antifeedants

PHLORETIN 4′-O-β-D-GLUCOPYRANOSIDE

785

C21H24O10 (436.41)

CH2OH O

O

HO

[α]25 D : –65° (EtOH)

O

HO

M.p. : 128–130°

H OH

H

O H OH

OH

(1)

(1)

SOURCE: Malus pumila var. dulcissima Mill., apple (Rosaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 200 ppm

Efficacy

Remarks

Feeding inhibition = 50%

Treatment to 50–75 aphids at random for 24 h. Concentration = EC50 (1)

(1) Kubo, I. and Matsumoto, A. (1985) Chem. Pharm. Bull., 33, 3817.

© 2005 by CRC Press LLC

786

Opender Koul

PHLORIZIN

C21H24O10 (436.41) OH

M.p. : 110° [α]25 D : –52° (EtOH)

OH

HO

HO

OH O

O

OH O OH

(1, 2)

(1)

SOURCE: Naturally occurring flavonoid in grasses and apple trees

(2)

ACTIVITY PROFILE Test Insect 1. Schizaphis graminum (Rondani) (Wheat aphid)

Test Method Artificial diet feeding

Conc. / Dose 0.02%

Efficacy Feeding inhibition = 50%

Remarks 1. Treatment to 50–75 aphids at random for 24 h. Concentration = EC50 (2)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

0.14%

Feeding inhibition = 50%

2. Treatment to 50–75 aphids at random for 8 h. Concentration = EC50 (2)

(1) Williams, A.H. (1961) J. Chem. Soc., 4133. (2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC

Insect Antifeedants

PHTHALIC ACID

787

C8H6O4 (166.13)

M.p. : 212–213° (210° dec.)

COOH COOH

(1, 2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Test Method

Conc. / Dose

Paper towel disk test

0.05 mg/cm2

Efficacy

Remarks

Feeding inhibition = 11.4%

Treatment to larvae of 10 to 13 mg body weight. Treatment duration = 6 days. (2) Data calculated from Reference 2.

LD50 (rats): 7.9 g/kg (oral)

(3)

(1) Cross, B.E., Galt, R.H.B., Hanson, J.R., Curtis, P.J., Grove, J.F., and Morrison, A. (1963) J. Chem. Soc., 2937. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. (3) Shaffer, C.B., Carpenter, C.P., and Smyth, H.F. Jr. (1945) J. Ind. Hyg. Toxicol., 27, 130.

© 2005 by CRC Press LLC

788

Opender Koul

PHYTOL

C20H40O (296.54)

B.p. : 150–151°/0.06 mm n25 D

: 1.4637

[α]18 D : +0.2° H

H OH

(1, 2, 3)

(1, 2)

SOURCE: Callicarpa japonica Thunb., beauty berry (Verbenaceae)

(3)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab,) (Tobacco armyworm))

LD50 (rats): >5000 mg/kg (oral) (1) (2) (3) (4)

Test Method

Conc. / Dose

Leaf disk test

5000 ppm

Efficacy

Remarks

Feeding inhibition = 100% within 2 h

Treatment to 3rd instar larvae. Activity retards after 6 h. Therefore, compound is termed as relative antifeedant. (3)

(4)

Fujisawa, T., Sato, T., Kawara, T., and Ohashi, K. (1981) Tetrahedron Lett., 22, 4823. von Bader, F . (1951) Helv. Chim. Acta, 34, 1632. Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045. Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

PICRASIN–B

789

C21H28O6 (376.45)

M.p. : 255–257° [α]D : +16.4° (CHCl3)

OCH3 O

O

HO

H O

O

H H

(1, 2)

(1, 2)

SOURCE: Picrasma quassioides Benn., Indian quassia (Simaroubaceae) Also found in Soulamea pancheri Brongn. & Griseb. (Simaroubaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Heliothis virescens (Fab.) (Tobacco budworm)

Leaf disk test

19.8 µg/cm2

Feeding inhibition = 30–60% after 2 days and 0–30% after 6 days

1. Treatment to 3rd instar larvae. (3)

2. Epilachna varivestis Mulsant (Mexican bean beetle)

Whole leaf application

500 ppm

Feeding inhibition = 85.9%

2. Treatment to 4th instar larvae for 24 h. Larvae pre-starved for 2 h. Data calculated from Reference 4.

3. Spodoptera eridania (Cramer) (Southern armyworm)

Whole leaf application

500 ppm

Feeding inhibition = 25.0%

3. Treatment to 5th instar larvae as above. (4)

(1) Hiniko, H., Ohta, T., and Takemoto, T. (1970) Chem. Pharm. Bull., 18, 219. (2) Viala, B. and Polonsky, J. (1970) Compt. Rend., 271C, 410. (3) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442. (4) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC

790

Opender Koul

PICROTOXININ

C15H16O6 (292.29)

M.p. : 209.5° [α]D : –5.85° (CHCl3)

O

O

O O

O

OH

(1, 2)

(1)

SOURCE: Anamirta cocculus (L.) Wight and Arn., fishberry (Menispermaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Diabrotica virgifera virgifera (LeConte) (Western corn rootworm)

Test Method

Conc. / Dose

Leaf disk test

115 µg/1.5 cm2

Feeding inhibition = 50.0%

1. Treatment to adults of resistant insects.

51.9 µg/1.5 cm2

Feeding inhibition = 50.0%

Treatment to adults of susceptible insects.

Efficacy

Remarks

Concentration = EC50 value. (2) 2. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk no-choice assay

70.0 µg/1.5 cm2

Feeding inhibition = 43.3%

2. Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 30 min. (3)

(1) Conroy, H. (1957) J. Am. Chem. Soc., 79, 5550. (2) Mullin, C.A., Mason, C.H., Chou, J., and Linderman, J.R. (1992) In C.A. Mullin and Scott, J.G. (eds.), Molecular Mechanisms of Insecticide Resistance: Diversity Among Insects, ACS Symp. Ser. 505, Washington, D.C., pp. 288–308. (3) Passreiter, C.M. and Isman, M.B. (1997) Biochem. Syst. Ecol., 25, 371.

© 2005 by CRC Press LLC

Insect Antifeedants

PIMPINELLIN

791

C13H10O5 (246.22)

M.p. : 119°

OCH3 H3CO

O

O

O

(1, 2, 3)

(1, 2)

SOURCE: Pimpinella saxifraga L., pimpinella (Apiaceae)

(1, 3)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Efficacy

Remarks

Leaf disk test

1000 ppm

Feeding ratio = 2.0%

100 ppm

Feeding ratio = 1.0%

Treatment to 3rd instar larvae. Ratio level between 0–20% considered to be highly active. (3)

(1) Heut, J. (1898) Arch. Pharm., 236, 162. (2) Wessely, F. and Kallab, F. (1908) Montash, 59, 161. (3) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC

792

Opender Koul

PINGUISONE

C15H20O2 (232.32)

M.p. : 63–63.5° [α]25 D : +64.3° (Benzene)

O

O

(1, 2)

(1)

SOURCE: Aneura pinguis L., liverwort (Metzgeriales)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

0.5%

Feeding inhibition = 100%

Treatment to 10- to 13-day-old larvae. (2)

0.25%

Feeding inhibition = 100%

0.125%

Feeding inhibition = 93.0%

(1) Benesova, V., Samek, Z., Herout, V., and Sorm, F. (1969) Collect. Czech. Chem. Commun., 34, 582. (2) Wada, K. and Munakata, K. (1971) Agric. Biol. Chem., 35, 115.

© 2005 by CRC Press LLC

Insect Antifeedants

PIPECOLIC ACID

793

C6H11O2N (129.16)

M.p. : 270° [α]25 D : +24.5°

H N

COOH

(1, 2)

(1, 2)

SOURCE: Acacia spp. (Fabaceae)

(2)

ACTIVITY PROFILE Test Insect 1. Anacridium melanorhodon arabafrum (Dirsh) (Tree locust)

2. Locusta migratoria migratoriodes (R and F) (Migratory locust)

Test Method Glass fiber disk test

Glass fiber disk test

Conc. / Dose

Efficacy

Remarks

1.0% of disk weight

Feeding inhibition = 30–60%

1. Treatment to nymphs at random. (2)

5.0% of disk weight

Feeding inhibition = 90–100%

0.5% of disk weight

Feeding inhibition = 30–60%

(1) Stevens, C.M. and Ellman, P.B. (1950) J. Biol. Chem., 182, 75. (2) Evans, C.S. and Bell, E.A. (1979) Phytochemistry, 18, 1807.

© 2005 by CRC Press LLC

2. Treatment to male 5th instar nymphs. (2)

794

Opender Koul

PIPERENONE

C22H28O6 (388.46)

M.p. : 86–88°

H3CO

[α]20 D : –129° (MeOH) H3CO

O OCH3

H3CO O

(1)

(1)

SOURCE: Piper futokadzura Sieb. et Zucc., Japanese piper (Piperaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

0.05%

Feeding inhibition = 90–100%

0.01%

Feeding inhibition = 90–100%

0.005%

Feeding inhibition = 90–100%

0.001%

No activity

Remarks Treatment to 3rd instar larvae. (1)

(1) Matsui, K., Wada, K., and Munakata, K. (1976) Agric. Biol. Chem., 40, 1045.

© 2005 by CRC Press LLC

Insect Antifeedants

(+) PISATIN

795

C17H14O6 (314.29)

H3CO

M.p. : 188–190°

O OH O O

O

(1, 2)

(1)

SOURCE: Pisum sativum L., green pea (Fabaceae)

(2, 3)

ACTIVITY PROFILE Test Insect 1. Costelytra zealandica (White) (Scarab beetle)

2. Heteronychus arator (Fab.) (Black beetle)

Test Method

Conc. / Dose

Artificial diet feeding

Artificial diet feeding

Efficacy

Remarks

200.0 µg/ml

Feeding inhibition = 100%

1. Treatment to 3rd instar larvae after 24-h pre-starvation.

100.0 µg/ml

Feeding inhibition = 100%

200.0 µg/ml

Feeding inhibition = 4.0%

Negative feeding response observed. (3) 2. Treatment to 3rd instar larvae after 24-h pre-starvation. (3)

(1) Bevan, C.W.L., Birch, A.J., Moore, B., and Mukerjee, S.K. (1964) J. Chem. Soc., 5991. (2) Keen, N.T. (1975) Phytopathology, 65, 91. (3) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

© 2005 by CRC Press LLC

796

Opender Koul

PISCIDINOL–C

C32H46O8 (558.71)

M.p. : 215°

OH

O

O

AcO HO

O

OH

(1, 2, 3)

(1, 2)

SOURCE: Walsura piscida Roxb., walasura (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Leaf disk dual-choice test

Efficacy

Remarks

1.0 µg/cm2

Feeding inhibition = 47.5%

Treatment to 3rd instar larvae for 24 h.

5.0 µg/cm2

Feeding inhibition = 51.5%

EC50 = 1.84 µg/cm2

10.0 µg/cm2

Feeding inhibition = 61.6%

50.0 µg/cm2

Feeding inhibition = 62.4%

Data calculated from Reference 3. (3)

(1) Purushothaman, K.K., Duraiswamy, K., Connolly, J.D., and Rycroft, D.S. (1985) Phytochemistry, 28, 2349. (2) Govindachari, T.R., Krishna Kumari, G.N., and Suresh, G. (1995) Phytochemistry, 39, 167. (3) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari, G.N. (1995) J. Chem. Ecol., 21, 1586.

© 2005 by CRC Press LLC

Insect Antifeedants

PLAGIOCHILINE–A

797

C19H26O6 (350.41)

Oil [α]D : +32.3° (CHCl3)

AcO H

O

O

H

H

AcO

(1, 2)

(1, 2) SOURCE: Plagiochila yokogurensis Inoue, liverwort (Fungi)

(1)

ACTIVITY PROFILE Test Insect Spodoptera exempta (Walker) (Nutgrass armyworm)

Test Method Leaf disk test

Conc. / Dose 1–10 ng/cm2

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to larvae for 2 h. (1)

(1) Asakawa, Y., Toyota, M., Takemoto, T., Kubo, I., and Nakanishi, K. (1980) Phytochemistry, 19, 2147. (2) Matsuo, A., Atsumi, K., and Nakayama, M. (1981) J. Chem. Soc. Perkin I, 2816.

© 2005 by CRC Press LLC

798

Opender Koul

PLICTRAN

C18H34OSn (385.16)

HO

M.p. : 195–198°

Sn

(1, 2)

(1)

SOURCE: Commercial material

(2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf dip test

Conc. / Dose 0.05%

Efficacy Feeding inhibition = 95.0%

Remarks 1. Treatment to larvae weighing 170–190 mg. (2)

2. Scolytus mediterraneus Eggers (Fruit bark beetle)

Twig dip test

3. Gnorimoschema operculella (Zell.) (Potato tuber moth)

Leaf dip test

0.05–0.2%

Feeding inhibition = 28–75%

2. Treatment to 0- to 1-day-old females. Observation based on twig penetration. (3)

Feeding inhibition = 67.4%

3. Treatment to 2nd instar larvae. Data based on larval mining calculated from Reference 4. (4)

0.05%

LD50 (rats): 540 mg/kg (oral) (1) The Agrochemicals Handbook (1986), Roy. Soc. Chem. (2) Ascher, K.R.S., Avdat, N., and Kamhi, J. (1970) Int. Pest Contr., 12, 11. (3) Ascher, K.R.S., Gurevitz, E., Renneh, S., and Nemny, N.E. (1975) Z. Pflkrankh. Pflschutz., 82, 378. (4) Ascher, K.R.S. and Meisner, J. (1969) Z. Pflkrankh. Pflpath. Pflschutz., 76, 564. (5) Farms Chem. Handbook (1982) Meister Publishing Co., C232.

© 2005 by CRC Press LLC

(5)

Insect Antifeedants

PODOPHYLLOTOXIN

799

C22H22O8 (414.41) OH

M.p. : 183.3–184.0° [α]20 D : –132.7° (CHCl3)

O O O O

H3CO

OCH3 OCH3

(1, 2)

(1)

SOURCE: Podophyllum peltatum L., may apple, mandrake (Berberidaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Peridroma saucia (Hubner) (Variegated cutworm)

LD50 (mouse): 100 mg/kg (oral)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

5.7 µg/cm2

Feeding inhibition = 51.7%

Treatment to 5th instar larvae for 5 h. (2)

11.4 µg/cm2

Feeding inhibition = 75.5%

28.5 µg/cm2

Feeding inhibition = 81.8%

(3)

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 184. (2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

800

Opender Koul

POLHOVOLIDE

C23H32O8 (436.50)

M.p. : 98–99° [α]20 D : –83.5° (CHCl3)

OAc

O OAc O O

O

(1, 2)

(1)

SOURCE: Laserpitium siler L., mountain lasser-wort (Apiaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

1.0%

Feeding deterrence coefficient = 121

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

1.0%

Feeding deterrence coefficient: Adults = 132 Larvae = 137

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

1.0%

Feeding deterrence coefficient = 54.0

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Holub, M., Motl, O., and Samek, Z. (1978) Collect. Czech. Chem. Commun., 43, 2471. (2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

© 2005 by CRC Press LLC

Insect Antifeedants

POLYGODIAL

801

C15H22O2 (234.34)

M.p. : 57° (50°) B.p. : 138–140°/0.8 mm

CHO

[α]24 D : –131° (EtOH) CHO

H

(1, 2)

(1, 2)

SOURCE: Warburgia stuhlmanni L., warburgia (Canellaceae) Polygonum hydropiper L., marsh pepper (Polygonaceae)

(1, 2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Leaf disk choice test

>0.1 ppm

Considered weaker antifeedant than warburganal

1. Treatment to larvae. Exact quantitative data not recorded. (2)

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk dual-choice assay

5 mM

Feeding inhibition = 92.0%

2. Treatment to larvae of 90–120 mg body weight for a period of 3 h. (3)

Test Insect

Efficacy

Remarks

(1) Barnes, C.S. and Loder, J.W. (1962) Aust. J. Chem., 15, 322. (2) Nakanishi, K. and Kubo, I. (1977) Israel J. Chem., 16, 28. (3) Gols, G.J.Z., van Loon, J.J.A., and Messchendorp, L. (1996) Entomol. Exp. Appl., 79, 69.

© 2005 by CRC Press LLC

802

Opender Koul

7-O-PRENYL FLAVONONE

C21H20O3 (320.37)

No physical data given

O O

O

(1)

(1)

SOURCE: Lonchocarpus neuroscapha Bentt., coroa piaca (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nutgrass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dualchoice test

Glass fiber disk dualchoice test

Efficacy

Remarks

100 ppm

Feeding inhibition = 74.0%

10 ppm

Feeding inhibition = 36.0%

1. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (1)

500 ppm

Feeding inhibition = 29.0%

2. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (1)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

Insect Antifeedants

8 – PRENYL FLAVANONE

HO

803

C21H22O8 (322.39)

No physical data given

O

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nutgrass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Glass fiber disk dualchoice test

Glass fiber disk dualchoice test

Efficacy

Remarks

100 ppm

Feeding inhibition = 79.0%

10 ppm

Feeding inhibition = 34.0%

1. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (1)

500 ppm

Feeding inhibition = 41.0%

2. Treatment to 24- to 36-h-old final stadium larvae for 5 h. Larvae prestarved for 4 h. (1)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC

804

Opender Koul

PRIEURIANIN

C38H50O16 (762.80)

OH

M.p. : 214–218° [α]D20 : +13.3° (CHCl3)

O O O AcO

COOH

O

OH CH2

O CH2OAc

O

COOCH3

(1, 2)

(2, 3)

SOURCE: Nymania capensis (Thunb.) Lindb., Chinese lantern (Meliaceae) Entandrophragma candolei Harms, candollei (Meliaceae)

(1, 2) (3)

ACTIVITY PROFILE Test Insect 1. Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

19.8 µg/cm2

Feeding inhibition = 60.0%

6.0 µg/cm2

Feeding inhibition = 30.0%

Remarks 1. Treatment to 3rd instar larvae for 2 days.

2. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

19.8 µg/cm2

Feeding inhibition = 30.0%

2. Treatment to 3rd instar larvae for 2 days.

3. Heliothis virescens (Fab.) (Tobacco budworm)

Leaf disk choice test

19.8 µg/cm2

Feeding inhibition = 60.0%

6.0 µg/cm2

Feeding inhibition = 30.0%

3. Treatment to 3rd instar larvae for 2 days. (1)

4. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 175.8

4. Treatment given to adults.

5. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient: Adults = 100 Larvae = 139.1

5. Treatment given to both adults and larvae.

6. Trogoderma granarium Everts (Khapra beetle)

Diet choice assay

10 mg/ml

Feeding deterrence coefficient = 166.7

6. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (3)

© 2005 by CRC Press LLC

Insect Antifeedants

7. Helicoverpa armigera (Hubner) (Gram pod borer)

Wafer disk test

91.4 ppm

Feeding deterrence = 50%

805

7. Treatment to 3rd instar larvae, prestarved for 4 h. (4)

(1) Lidert, Z., Taylor, D.A., and Thirugnanam, M. (1985) J. Nat. Prod., 48, 843. (2) Gullo, V.P., Miura, L., Nakanishi, K., Cameron, A.F., Connoly, J.D., Harding, A.E., McCrindle, R., and Taylor, D.A.H. (1975), J. Chem. Soc. Chem. Commun., 345. (3) Daniewski, W.M., Gumulka, M., Ancezewski, W., Truszewska, D., Bloszyk, E., and Drozdz, B. (1996) Polish J. Chem., 70, 1265. (4) Koul, O., Daniewski, W.M., Multani, J.S., Gumulka, M., and Singh, G. (2003) J. Agric. Food Chem., 51, 7271.

© 2005 by CRC Press LLC

806

Opender Koul

PRIEURIANIN ACETATE

C40H52O17 (804.84)

OAc O

M.p. : 183° [α]D25 : 56.4° (pyridine)

O O AcO

COOH

O

OH CH2

O CH2OAc

O

COOCH3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

1. Epilachna varivestis Mulsant (Mexican bean beetle)

Leaf disk choice test

2. Spodoptera eridania (Cramer) (Southern armyworm)

3. Heliothis virescens (Fab.) (Tobacco budworm)

Leaf disk choice test

Leaf disk choice test

Conc. / Dose

Efficacy

6.0 µg/cm2

Feeding inhibition = 90.0%

1.5 µg/cm2

Feeding inhibition = 30.0%

19.8 µg/cm2

Feeding inhibition = 90.0%

6.0 µg/cm2

Feeding inhibition = 60.0%

19.8 µg/cm2

Feeding inhibition = 60.0%

6.0 µg/cm2

Feeding inhibition = 60.0%

Remarks 1. Treatment to 3rd instar larvae for 2 days.

2. Treatment to 3rd instar larvae for 2 days.

3. Treatment to 3rd instar larvae for 2 days. (1)

4. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 164.5

4. Treatment given to adults.

5. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient. Adults = 168.4 Larvae = 140.8

5. Treatment given to both adults and larvae.

© 2005 by CRC Press LLC

Insect Antifeedants

807

6. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 167.8

6. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (2)

7. Helicoverpa armigera (Hubner) (Gram pod borer)

Diet choice assay

82.7 ppm

Feeding deterrence = 50%

7. Treatment to 3rd instar larvae, prestarved for 2 h. (3)

(1) Lidert, Z., Taylor, D.A., and Thirugnanam, M. (1985) J. Nat. Prod., 48, 843. (2) Daniewski, W.M., Gumulka, M., Ancezewski, W., Truszewska, D., Bloszyk, E., and Drozdz, B. (1996) Polish J. Chem., 70, 1265. (3) Koul, O., Daniewski, W.M., Multani, J.S., Gumulka, M., and Singh, G. (2003) J. Agric. Food Chem., 51, 7271.

© 2005 by CRC Press LLC

808

Opender Koul

epoxy-PRIEURIANIN

C38H50O15 (746.80)

OH

[α]D : +24.5° (CHCl3)

O O O

AcO

COOH O

O CH2

O CH2OAc

COOCH3

(1, 2)

(1)

SOURCE: Entandrophragma candolei Harms, candolei (Meliaceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 196.5

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient: Adults = 196.5 Larvae = 141.8

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 67.7

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (1)

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Diet choice assay

62.0 ppm

Feeding deterrence = 50%

4. Treatment to 3rd instar larvae, prestarved for 4 h. (3)

Test Insect

Efficacy

Remarks

(1) Lukacova, V., Polonsky, J., Moretti, C., Pettit, G.R., and Schmidt, J.M. (1982) J. Nat. Prod., 45, 288. (2) Daniewski, W.M., Gumulka, M., Ancezewski, W., Truszewska, D., Bloszyk, E., and Drozdz, B. (1996) Polish J. Chem., 70, 1265. (3) Koul, O., Daniewski, W.M., Multani, J.S., Gumulka, M., and Singh, G. (2003) J. Agric. Food Chem., 51, 7271.

© 2005 by CRC Press LLC

Insect Antifeedants

epoxy-PRIEURIANIN ACETATE

809

C40H52O16 (788.84)

OAc

Only spectral data given

O O O

AcO

COOH O

O CH2

O CH2OAc

COOCH3

(1, 2)

(2)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 187.0

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient: Adults = 167.6 Larvae = 163.4

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 200

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (1)

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Diet choice assay

48.3 ppm

Feeding deterrence = 50%

4. Treatment to 3rd instar larvae, prestarved for 4 h. (2)

Test Insect

Efficacy

Remarks

(1) Daniewski, W.M., Gumulka, M., Ancezewski, W., Truszewska, D., Bloszyk, E., and Drozdz, B. (1996) Polish J. Chem., 70, 1265. (2) Koul, O., Daniewski, W.M., Multani, J.S., Gumulka, M., and Singh, G. (2003) J. Agric. Food Chem., 51, 7271.

© 2005 by CRC Press LLC

810

Opender Koul

PRONAMIDE

C12H11ONCl2 (256.13)

Cl

CONHC

C

M.p. : 155–157°

CH

Cl

(1)

(1)

SOURCE: Commercial sample (a herbicide)

(2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf dip test

Conc. / Dose

Efficacy

Remarks

0.3% a.i. from WP 50%

Weight gain of 70.9 mg against 211.5 mg in controls

0.2% a.i. from WP 50%

Weight gain of 87.5 mg against 211.5 mg in controls

Treatment to larvae of 90–100 mg body weight. Antifeedant effect based on weight gain after 48 h. (2)

0.1% a.i. from WP 50%

Weight gain of 116.5 mg against 211.5 mg in controls

(1) Swithenbank, C., McNulty, P.J., and Viste, K.L. (1971) J. Agric. Food Chem., 19, 417. (2) Meisner, J., Lifshitz, N., and Ascher, K.R.S. (1987) J. Econ. Entomol., 80, 724.

© 2005 by CRC Press LLC

Insect Antifeedants

n-PROPYL GALLATE

811

C10H12O5 (212.20) M.p. : 150°

COO

OH

HO OH

(1)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect 1. Schizaphis graminum (Rondani) (Wheat aphid)

Test Method Artificial diet feeding

Conc. / Dose 96 ppm

Efficacy Feeding inhibition = 50.0%

Remarks 1. Treatment to aphids at random. Concentration = EC50 value.

2. Acyrthosiphon pisum (Harris) (Pea aphid)

Artificial diet feeding

304 ppm

Feeding inhibition = 50.0%

2. Treatment to aphids at random. Concentration = EC50 value.

3. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

198 ppm

Feeding inhibition = 50.0%

3. Treatment to aphids at random. Concentration = EC50 value. (2)

LD50 (rats): 3.8 g/kg (oral) (1) Jasim, F. (1970) Talanta, 17, 103. (2) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229. (3) Clayton, G.D. and Clayton, F.E. (1981) Patty’s Industrial Hygiene and Toxicology, 2A, 2326.

© 2005 by CRC Press LLC

(3)

812

Opender Koul

PROTOCATECHUIC ACID

C 7 H 6O 4 (154.12)

M.p. : ~200° (dec.) (195–196°, anhyd.)

COOH

OH

OH

(1, 2)

(1, 3)

SOURCE: Pteridium aquilinum L. Kuhn, bracken fern (Pteridophyta)

(2)

ACTIVITY PROFILE Test Insect Pieris brassicae (L.) (Large white butterfly)

Test Method Leaf disk no-choice test

Conc. / Dose

Efficacy

Remarks

6.5 × 10–2 M

Feeding ratio = 2.87

Treatment to 2nd day 5th instar larvae. Feeding ratio < 20 strong antifeedant effect. (2)

(1) Horhammer, L. and Scherm, A. (1955) Arch. Pharm., 288, 441. (2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187. (3) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC

Insect Antifeedants

PSORALEN

813

C11H6O3 (186.17)

O

O

M.p. : 171° (161–162°, 165°)

O

(1, 2)

(1, 2)

SOURCE: Commercial sample used for evaluation. However, compound occurs in Psoralea spp. and some plants of family Fabaceae.

(2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Artificial diet test

Conc. / Dose 170 ppm

Efficacy Feeding inhibition = 50.0%

Remarks Treatment to 4th instar larvae, prestarved for 4 h. Treatment duration = 48 h. Concentration = EC50 value. (2)

(1) Murray, R.D.H. (1982) The Natural Coumarins, John Wiley, New York. (2) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem., 37, 1435.

© 2005 by CRC Press LLC

814

Opender Koul

PTEROSIN–F

C14H17OCl (236.74)

M.p. : 66–67° [α]D : –9.2° (benzene)

O Cl

(1, 2)

(1, 2) SOURCE: Pteridium aquilinum L. Kuhn, bracken fern (Pteridophyta)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Pieris brassicae (L.) (Large white butterfly)

Leaf disk nochoice test

100 mg/kg fresh disk weight

Feeding ratio = 4.0

1. Treatment to 2nd day 5th instar unstarved larvae. (3)

2. Chilo partellus (Swinhoe) (Maize borer)

Leaf disk nochoice test

100 mg/kg fresh disk weight

Feeding ratio = 5.0

2. Treatment to 2nd day 5th instar unstarved larvae. (3) Feeding ratio < 20 very strong antifeedant effect.

Test Insect

Efficacy

Remarks

(1) Yoshihira, K., Fukuoka, M., Kuroyanagi, M., and Natori, S. (1971) Chem. Pharm. Bull., 19, 1491. (2) Yoshihira, K., Fukuoka, M., Kuroyanagi, M., and Natori, S. (1972) Chem. Pharm. Bull., 20, 426. (3) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 95.

© 2005 by CRC Press LLC

Insect Antifeedants

PUNGENIN

815

C14H18O8 (314.29)

O

M.p. : 198–199° (190–191) [α]D22 : –96.8° (H2O)

CH2OH O

O

HO HO

OH

OH

(1, 2)

(1)

SOURCE: Picea pungens Engelm., Colorado spruce P. glauca (Moench) Voss, white spruce (Pinaceae) Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect Choristoneura fumiferana (Clem.) (Spruce budworm)

Test Method Paper disk test

Conc. / Dose 5.0%

Efficacy Modest antifeedant effect

Remarks Treatment to 6th instar larvae. No quantitative data recorded. (2)

(1) Neish, A.C. (1957) Can. J. Biochem., 35, 161. (2) Strunz, G.M., Ciguere, P., and Thomas, A.W. (1986) J. Chem. Ecol., 12, 251.

© 2005 by CRC Press LLC

816

Opender Koul

PYROGALLOL

C6H6O3 (126.11)

M.p. : 133–134° B.p. : 171.5°/12 mm

OH

HO OH

(1)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

144 ppm

Feeding inhibition = 50.0%

1. Treatment to aphids at random. Concentration = EC50 value.

2. Acyrthosiphon pisum (Harris) (Pea aphid)

Artificial diet feeding

455 ppm

Feeding inhibition = 50.0%

2. Treatment to aphids at random. Concentration = EC50 value.

3. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

276 ppm

Feeding inhibition = 50.0%

3. Treatment to aphids at random. Concentration = EC50 value. (2)

LD50 (rats): 789 mg/kg (oral) (1) Rindrknecht, H. and Niemann, C. (1948) J. Am. Chem. Soc., 70, 2605. (2) Jones, K.C. and Klocke, J.A. (1987) Entomol Exp. Appl., 44, 229. (3) Lewis, R.J. and Tatken, R.L. (1980) RTECS, 2, 539.

© 2005 by CRC Press LLC

(3)

Insect Antifeedants

817

1-O-PYRUVYL-22,23-DIHYDROAZADIRACHTININ No physical data given COOCH3 pyruvate - O

O

OH

OH

O

O

O

OH

AcO H H3COOC

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to 24- to 36-h-old starved final stadium larvae. Bioassay terminated after the larvae had consumed about 50% of one of the disks. (1)

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 55.0%

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 52.0%

3. Heliothis virescens (Fab.) (Tobacco budworm)

Glass fiber disk choice test

1 ppm

Feeding inhibition = 63.0%

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Glass fiber disk choice Test

1 ppm

Feeding inhibition = 44.0%

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149.

© 2005 by CRC Press LLC

818

Opender Koul

QUADRANGOLIDE

C15H20O3 (248.32)

M.p. : 118–120° [α]D22 : +227° (neat)

O O

CH2

O

(1)

(1)

SOURCE: Eupatorium quadrangularae L., joe-pye-weed (Asteraceae)

(1)

ACTIVITY PROFILE Test insect Atta cephalotes (L.) (Leaf cutter ant)

Test Method

Conc. / Dose

Efficacy

Rye flake forcedchoice feeding

6 mg/ml or 120 µg/flake

Feeding inhibition = 94.1%

(1) Hubert, T.D., Okunade, A.L., and Wiemer, D.F. (1987) Phytochemistry, 26, 1751.

© 2005 by CRC Press LLC

Remarks Treatment to adult workers. Data calculated from Reference 1. (1)

Insect Antifeedants

QUASSIN

819

C22H28O6 (388.46)

M.p. : 221–222° [α]D20 : +34.5° (CHCl3)

OCH3 O

O

H3CO H O

O H

(1, 2)

(1)

SOURCE: Quassia amara L., Surinam quassia (Simaroubiceae)

(1,2)

ACTIVITY PROFILE Test insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Heliothis virescens (Fab.) (Tobacco budworm)

Leaf disk test

19.8 µg/cm2

Feeding inhibition = 30–60%

1. Treatment to 3rd instar larvae for 2 days. (2)

2. Epilachna varivestis Muls. (Mexican bean beetle)

Whole leaf application

250 ppm

Feeding deterrence = 90.0%

100 ppm

Feeding deterrence = 92.0%

2. Treatment to 4th instar larvae for 24 h. Larvae pre-starved for 2 h.

50 ppm

Feeding deterrence = 87.8%

Data calculated from Reference 3. (3)

(1) Valenta, Z., Papadopoulos, S., and Podesva, C. (1961) Tetrahedron, 15, 100. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

820

Opender Koul

QUERCETIN

C15H10O7 (302.23)

M.p. : 314° (dec.) (anhydrous)

OH OH

HO

O

OH OH

O

(1)

(1)

SOURCE: Rhodendron cinnabaricum Hook, rhododendron (Ericaceae) and many other plant species

(1, 2)

ACTIVITY PROFILE Test insect 1. Schizaphis graminum (Rondani) (Wheat aphid)

Test Method Artificial diet feeding

Conc. / Dose 0.08%

Efficacy Feeding inhibition = 50.0%

Remarks 1. Treatment to 50–75 aphids at random for 24 h. Concentration = EC50 value. (2)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

0.03%

Feeding deterrence = 50.0%

2. Treatment to 50–75 aphids at random for 8 h. Concentration = EC50 value. (2)

LD50 (mice): 180 mg/kg (oral) (1) Rangaswami, S., Sambamurthy, K., and Mallayya Sastry, K. (1962) Proc. Ind. Acad. Sci., 56A, 239. (2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489. (3) Sullivan, M., Folks, R.H. Jr., and Hilgartner, M. (1951) Proc. Soc. Exp. Biol. Med., 77, 269.

© 2005 by CRC Press LLC

(3)

Insect Antifeedants

QUERCITRIN

821

C21H20O11 (448.38) OH OH

HO

M.p. : 182–185° (250–252°) (anhydrous) [α]15 D : –158° (MeOH)

O

O

OH O

OH

O

HO

OH

(1)

(1, 2)

SOURCE: Semisynthetic and many plant species

(3)

ACTIVITY PROFILE Test insect 1. Schizaphis graminum (Rondani) (Wheat aphid)

Test Method Artificial diet feeding

Conc. / Dose 0.06%

Efficacy Feeding inhibition = 50.0%

Remarks 1. Treatment to 50–75 aphids at random for 24 h. Concentration = EC50 value. (3)

2. Myzus persicae (Sulzer) (Green peach aphid)

Artificial diet feeding

0.06%

Feeding deterrence = 50.0%

2. Treatment to 50–75 aphids at random for 8 h. Concentration = EC50 value. (3)

(1) Zemplen, G., Csuros, Z., Gerecs, A., and Aczel, S. (1928) Ber., 61, 2486. (2) Horhammer, L., Wagner, H., Arndt, H., Dirschrel, R., and Farkas, L. (1968) Chem. Ber., 101, 450. (3) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC

822

Opender Koul

QUININE

C20H24O2N2 (324.42)

M.p. : 177° (anhydrous) [α]15 D : –159° (EtOH)

CH2 HO N H

H3CO

N

(1, 2)

(1)

SOURCE: Commercial sample

(1)

ACTIVITY PROFILE Test insect Phormia regina (Meigen) (Blowfly)

Test Method Sucrose solution feeding

Conc. / Dose 10 mM

Efficacy

Remarks

Feeding inhibition = 93.0%

Treatment to 2-, 4-, and 6-day-old adults, pre-starved for 24 h. Treatment duration = 6–24 h. (2)

LD50 (mice): 115 mg/kg (ipr.) (1) Merck Index (1983) p. 7963. (2) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299. (3) Hahn, F.E. (1979) Antibiotics, 5, 353.

© 2005 by CRC Press LLC

(3)

Insect Antifeedants

RACEMOSIN

823

C16H16O5 (288.30)

M.p. : 126–127°

OCH3 O

O

O

OCH3

(1, 2)

(1)

SOURCE: Atalantia racemosa Wight and Arn., wild lime (Rutaceae)

(1, 2)

ACTIVITY PROFILE Test insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Artificial diet feeding

Conc. / Dose 778 ppm

Efficacy Feeding inhibition = 50.0%

Remarks Treatment to 4th instar larvae, prestarved for 4 h. Treatment duration = 48 h. Concentration = EC50 value. (2)

(1) Joshi, B.S., Gawad, D.H., and Ravindranath, K.R. (1978) Proc. Ind. Acad. Sci., 87A, 173–179. (2) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem., 37, 1435.

© 2005 by CRC Press LLC

824

Opender Koul

REMIROL

C14H16O4 (248.28)

M.p. : 76–77° [α]D25 : +66.5°

O

CH3O

OH

O

CH 2

(1)

(1) SOURCE: Cyperus nipponicus, C. distans L., sedge (Cyperaceae)

(1)

ACTIVITY PROFILE Test insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk assay

Conc. / Dose

Efficacy

1.3 × 10–7 mol/cm2

Feeding inhibition = 50.0%

Remarks Treatment to 3rd instar larvae up to 5 h. Concentration = EC50 value. (1)

(1) Morimoto, M., Fujii, Y., and Komai, K. (1999) Phytochemistry, 51, 605.

© 2005 by CRC Press LLC

Insect Antifeedants

RHODOJAPONIN–III

825

C20H32O6 (368.46)

M.p. : 274° (dec.) 285–287°

OH H OH

O

OH OH OH

(1, 2)

(1, 2)

SOURCE: Rhododendron molle (B.) G.Don, yellow azalea (Ericaceae)

(1)

ACTIVITY PROFILE Test insect 1. Leptinitarsa decemlineata (Say) (Colorado potato beetle)

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

Efficacy

Remarks

2.8 µg/50 mm2

Feeding inhibition = 95.0%

1. Treatment to 4th instar larvae until 95% of control disk was eaten.

Leaf disk nochoice test

1.1 µg/50 mm2

Feeding inhibition = 95.0%

Concentration = PC95 value. (1)

Leaf disk choice test

6.4 µg/50 mm2

Feeding inhibition = 95.0%

2. Treatment to 3rd instar larvae until 95% of control disk was eaten.

Leaf disk nochoice test

1.6 µg/50 mm2

Feeding inhibition = 95.0%

Concentration = PC95 value. (1)

(1) Klocke, J.A., Hu, M., Chiu, S., and Kubo, I. (1991) Phytochemistry, 30, 1797. (2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 95.

© 2005 by CRC Press LLC

826

Opender Koul

RIDDELLINE

C18H23O6N (349.38)

M.p. : 197–198° [α]25 D : –109.5° (CHCl3)

CH2

OH

C

C

H C

C

H2C

COO

CH2OH

CH2OCO

N

(1)

(1, 2) SOURCE: Senecio riddellii L., groundsel (Asteraceae)

(2)

ACTIVITY PROFILE Test insect Acyrthosiphon pisum (Harris) (Pea aphid)

Test Method

Conc. / Dose

Artificial diet feeding

0.03 ± 0.006%

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to aphids at random. Concentration = EC50 value. (2)

LD50 (mice): 105 mg/kg (ivn.) (1) Adams, R., Hanlin, K.E. Jr., Jelinck, C.F., and Phillips, R.F. (1942) J. Am. Chem. Soc., 64, 2760. (2) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045. (3) Mattocks, A.R. (1986) Chemistry and Toxicology of Pyrrolizidine Alkaloids, Academic Press, New York.

© 2005 by CRC Press LLC

(3)

Insect Antifeedants

ROHITIUKA–7

827

C35H44O13 (672.72)

OH O

M.p. : 239–242° [α]D : –32°

O O COOH

O

OH CH2

O

OAc

O

O

(1, 2)

(1, 2)

SOURCE: Aphanamixis polystacha Wall & Parker, tiktara (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Heliothis virescens (Fab.) (Tobacco budworm)

Leaf disk choice test

2. Epilachna varivestis Muls. (Mexican bean beetle)

Leaf disk choice test

Test insect

Efficacy

Remarks

19.8 µg/cm2

Feeding deterrence = 60–90%

1. Treatment to 3rd instar larvae for 2 days. (1)

19.8 µg/cm2

Feeding inhibition = No activity

2. Treatment to 3rd instar larvae for 6 days. (1)

(1) Lidert, Z., Taylor, D.A., and Thirugnanam, M. (1985) J. Nat. Prod., 48, 843. (2) Brown, D.A. and Taylor, D.A.H. (1978) Phytochemistry, 17, 1955.

© 2005 by CRC Press LLC

828

Opender Koul

ROTENONE

C23H22O6 (394.42) H

M.p. : 162.5–164° [α]25 D : –225° (benzene)

H2C

H O

O

O

H O

OCH3 OCH3

(1)

(1, 2) SOURCE: Isolated from various species of Derris and Lonchocarpus (Fabaceae) Commercial sample

(1) (2)

ACTIVITY PROFILE Test insect 1. Costelytra zealandica (White) (Scarab beetle)

Test Method

Conc. / Dose

Artificial diet feeding

0.06 µg/g

Efficacy

Remarks

Feeding inhibition = 50.0%

1. Treatment to 24-h starved 3rd instar larvae. Concentration = EC50 value. (2)

2. Sitophilus granarius (L.) (Grain weevil)

Wafer disk assay

10 mg/ml

Feeding deterrence coefficient = 200

2. Treatment to adults. Data on 0–200 greater deterrence scale. (3)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk assay

10 mg/ml

Feeding deterrence coefficient = 200

3. Treatment to adults. Data on 0–200 greater deterrence scale. (3)

4. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk assay

10 mg/ml

Feeding deterrence coefficient = 200

4. Treatment to adults and larvae. Data on 0–200 greater deterrence scale. (3)

5. Spodoptera exempta (Walker) (Nutgrass armyworm)

© 2005 by CRC Press LLC

Leaf disk choice test

10 µg/2 cm diameter disk

Feeding deterrence = 82.0%

10 µg/2 cm diameter disk

Feeding deterrence = 52.0%

5. Treatment to mid6th instar larvae for 2 h. Larvae prestarved for 2 h. (5)

Insect Antifeedants

6. Eldana saccharina Walker (Sugar cane borer)

7. Maruca testulalis (Geyer) (Bean pod borer)

LD50 (mice): 2.8 mg/kg (i.p.)

Leaf disk choice test

Leaf disk choice test

100 µg/1.8 cm disk

Feeding deterrence = 89.0%

10 µg/1.8 cm disk

Feeding deterrence = 92.0%

1 µg/1.8 cm disk

Feeding deterrence = 81.0%

100 µg/1.8 cm disk

Feeding deterrence = 97.0%

10 µg/1.8 cm disk

Feeding deterrence = 86.0%

1 µg/1.8 cm disk

Feeding deterrence = 45.0%

829

6. Treatment to 5th instar larvae, prestarved for 12 h and allowed to feed for 24 h in dark. (5)

7. Treatment to late 5th instar larvae for 6 h. (4)

(5)

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 207. (2) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell, D.J. (1985) J. Chem. Ecol., 11, 1713. (3) Nawrot, J., Harmatha, J., Kostova, I., and Ognyanov, I. (1989) Biochem. Syst. Ecol., 17, 55. (4) Bentley, M.D., Hassanali, A., Lwandi, W., Nijoroge, P.E.W., Sitayo, E.N.O., and Yatagai, M. (1987) Insect Sci. Applic., 8, 85. (5) Fukami, J., Yamamoto, I., and Casida, J.E. (1967) Science, 155, 713.

© 2005 by CRC Press LLC

830

Opender Koul

RUTAEVIN

C26H30O9 (486.52) O

M.p. : 300° [α]26 D : –130° (Me2CO)

O

O

O

O

O

O

OH O

(1, 2)

(1)

SOURCE: Evodia rutaecarpa Hook f. et Thoms., Chinese Wu-Chu-Yu (Rutaceae)

(1)

ACTIVITY PROFILE Test insect Helicoverpa zea (Boddie) (Corn earworm)

Test Method

Conc. / Dose

Leaf disk choice test

125 µg/disk

Efficacy

Remarks

Feeding deterrence = 95%

Treatment to larvae. (2)

(1) Dreyer, D.L., Bennett, R.D., and Basa, S.C. (1976) Tetrahedron, 32, 2367. (2) Kubo, I. and Klocke, J.A. (1981) Colloques Inst. Nat. Recherches Agric., 7, 117.

© 2005 by CRC Press LLC

Insect Antifeedants

RUTIN

831

C27H30O16 (610.52)

M.p. : 214–215° (dec.) (anhydrous)

OH

[α]23 D : +13.82° (EtOH) OH

HO

O

rutinose

O OH

O

(1)

(1)

SOURCE: Found in many plants; also semisynthetic

(2)

ACTIVITY PROFILE Test insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 0.02%

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 50–75 aphids at random for 24 h. Concentration = EC50 value. (2)

LD50 (mice): 950 mg/kg (i.v.) (1) Merck Index (1983). (2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489. (3) Harrison, G. (1950) J. Am. Pharm. Assoc., 39, 557.

© 2005 by CRC Press LLC

(3)

832

Opender Koul

RYANODINE

C25H35O9N (493.55)

M.p. : 219–220° [α]D : +26° (MeOH)

OH OH

OH O

HO O O

OH HO NH

(1, 2)

(1, 2)

SOURCE: Ryania speciosa Vahl, ryania (Flacourtiaceae) Persea indica Spreng., canary wood (Lauraceae)

(1) (2)

ACTIVITY PROFILE Test insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

LD50 (rats): 750 mg/kg (oral); (mice): 0.1 mg/kg (i.p.)

Efficacy

Remarks

Feeding inhibition = 100%

Treatment to 3rd instar larvae for 1 day. Data based on antifeedant index = 0. Index less than 23 considered highly deterrent. (2)

(3)

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 98. (2) Gonzalex-Coloma, A., Terrero, D., Perales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem., 44, 296. (3) Crosby, D.G. (1971) In M. Jacobson and D.G. Crosby (eds.), Naturally Occurring Insecticides, Marcel Dekker, New York, pp. 177–139.

© 2005 by CRC Press LLC

Insect Antifeedants

RYANODOL

833

C20H32O8 (400.47)

M.p. : 345–347°

OH OH

OH O

HO HO

OH HO

(1)

(1)

SOURCE: Persea indica spreng., canary wood (Lauraceae)

(1)

ACTIVITY PROFILE Test insect Spodoptera litura (Fab.) (Tobacco armyworm)

LD50 (mice): 17.92 mg/kg (i.p.)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding inhibition = Approx. 100%

Treatment to 3rd instar larvae for 1 day. Data based on antifeedant index = 0.51. Index less than 23 considered highly deterrent. (1)

(1)

(1) Gonzalex-Coloma, A., Terrero, D., Perales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem., 44, 296.

© 2005 by CRC Press LLC

834

Opender Koul

SAINFURAN

H3CO

C16H14O5 (286.28)

M.p. : 150–152°

OH

OH

O OCH3

(1)

(1)

SOURCE: Onobrychis viciifolia Scop., sainfoin (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect Costelytra zealandica (White) (Scarab beetle)

Test Method Artificial diet feeding

Conc. / Dose 2 µg/g

Efficacy Feeding of insect larvae significantly reduced (P < 0.05) within 24 h of assessment.

Remarks Treatment to 3rd instar larvae. (1)

(1) Russel, G.B., Shaw, G.J., Christmas, P.E., Yates, M.B., and Sutherland, O.R.W. (1984) Phytochemistry, 23, 1417.

© 2005 by CRC Press LLC

Insect Antifeedants

SALANNIC ACID

835

C26H34O7 (458.55)

M.p. : 228–230°

COOH O

OH

H

O HO H

O

(1)

(1)

SOURCE: Synthetic Occurs in Melia dubia Cav., M. volkensii Guerke, Azadirachta indica A. Juss. (Meliaceae)

(1) (2)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Conc. / Dose 50 µg/cm2

Efficacy

Remarks

Feeding inhibition = 95.0%.

Treatment to newly moulted 3rd instar larvae. Disks examined every 2 h until >95% of control disks were eaten. (1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118. (2) Handerson, R., McCrindle, R., Melera, A., and Overton, K.H. (1968) Tetrahedron, 24, 1525.

© 2005 by CRC Press LLC

836

Opender Koul

SALANNIN

C34H44O9 (596.72) O

M.p. : 167–170° [α]D : +167° (CHCl3)

O O

O O H

O AcO H

O

(1)

(2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) Melia azedarach L., china berry; M. dubia Cav., and M. volkensii Guerke (Meliaceae)

(1–5)

ACTIVITY PROFILE Test Insect 1. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method

Conc. / Dose

Leaf disk choice test

>400 µg/disk

Feeding inhibition = 95.0%

1. Treatment to newly moulted 3rd instar larvae.

150 µg/disk

Feeding inhibition = 50.0%

Disks examined every 2 h until > 95% of control disks were eaten.

Efficacy

Remarks

Concentrations denote protection levels. (1) 2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Styropor lemellar test

0.1%

62.6% protection against controls

0.01%

48.4% protection against controls

2. Treatment to larvae of 100–120 mg body weight for 48 h. Data calculated from Reference 6. (6)

3. Earias insulana (Boisd.) (Spotted bollworm)

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Styropor lemellar test

0.1%

78.6% protection against controls

0.01%

57.1% protection against controls

3. Treatment to larvae of 20 mg body weight for 48 h. Data calculated from Reference 6. (6)

Insect Antifeedants

4. Epilachna varivestis (Mulsant) (Mexican bean beetle)

Bean half leaf assay

0.0082%

Feeding inhibition = 50.0%

837

4. Treatment to 4th instar larvae for 12 h. Concentration = EC50 value. (7)

5. Diabrotica undecimpunctata howardi Barber (Spotted cucumber beetle)

Leaf disk choice test

0.1% 0.5% 1.0%

6. Acalymma vittatum (Fab.) (Striped cucumber beetle)

Leaf disk choice test

0.1% 0.5% 1.0%

7. Musca domestica L. (Housefly)

Solution feeding

0.1%

Feeding deterrence = 79.0% Feeding deterrence = 76.0% Feeding deterrence = 90.0%

5. Treatment to adult beetles for 24 h. Data calculated from Reference 8. (8)

Feeding deterrence = 86.0% Feeding deterrence = 98.0% Feeding deterrence = 100%

6. Treatment to adult beetles for 24 h.

Feeding deterrence = 100%

7. Treatment to adults.

Data calculated from Reference 8. (8)

(9) 8. Spodoptera litura (Fab.) (Tobacco armyworm)

9. Pericallia ricini (Fab.) (Tiger moth)

10. Oxya fuscovittata (Marsh.) (Grasshopper)

Leaf disk dualchoice test

1 µg/cm2 10 µg/cm2

Leaf disk dualchoice test

1 µg/cm2

Leaf disk dualchoice test

1 µg/cm2

10 µg/cm2

10 µg/cm2

Feeding deterrence = 63.5% Feeding deterrence = 69.8%

8. Treatment to 3rd instar larvae for 24 h. (10)

Feeding deterrence = 70.7% Feeding deterrence = 77.5%

9. Treatment to 3rd instar larvae for 24 h. (10)

Feeding deterrence = 71.2% Feeding deterrence = 84.6%

10. Treatment to 3rd instar larvae for 24 h. (10)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118. (2) Henderson, R., McCrindle, R., Melera, A., and Overton, K.H. (1968) Tetrahedron, 24, 1525. (3) Srivastava, S.D. (1986) J. Nat. Prod., 49, 56. (4) Srivastava, S.D. and Srivastava, S.K. (1996) Fitoterapia, LXVII, 113. (5) Rajab, M.S., Bentley, M.D., Alford, A.R., and Mendel, M.J. (1988) J. Nat. Prod., 51, 168. (6) Meisner, J., Ascher, K.R.S., Aly, R., and Warthen, J.D. Jr. (1981) Phytoparasitica, 9, 27. (7) Schwinger, M., Ehhammer, B., and Kraus, W. (1983) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd Int. Neem Conf., GTZ, Eschborn, Germany, pp. 181–198. (8) Reed, D.K., Jacobson, M., Warthen, J.D. Jr., Uebel, E.C., Tromley, N.J., Jurd, L., and Freedman, B. (1981) USDA, ESA Tech. Bull. 1641, 1–13. (9) Warthen, J.D. Jr., Uebel, E.C., Dutky, S.R., Lusby, W.R., and Finigold, H. (1978) USDA, SEA, ARS Northeastern Series 2, 1–11. (10) Govindachari, T., Narasimhan, N.S., Suresh, G., Partho, P.D., and Gopalakrishnan, G. (1996) J. Chem. Ecol., 22, 1453.

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838

Opender Koul

SALANNOL

C32H44O8 (556.70) O

M.p. : 208° [α]20 D : +108.7° (CHCl3)

O O

O O H

O HO

H

O

(1, 2)

(1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf disk choice test

Conc. / Dose 0.05%

Efficacy

Remarks

Activity comparable to azadirachtin

Treatment to 4th stadium larvae for up to 24 h. No quantitative data reported. (1)

10 ppm

Feeding inhibition = 50%

Concentration = EC50 value. (3)

(1) Kraus, W., Baumann, S., Bokel, M., Keller, U., Klenk, A., Klingele, M., Pohnl, H., and Schwinger, M. (1987) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 3rd Int. Neem Conf., Nairobi, Kenya, GTZ, Eschborn, Germany, pp. 111–125. (2) Kraus, W. and Cramer, R. (1981) Liebigs Ann. Chem., 2381. (3) Kraus, W., Bokel, M., Schwinger, M., Vogler, B., Soellner, R., Wendisch, D., Steffens, R., and Wachendorff, U. (1993) In T. van Beek and H. Breteler (eds.), Phytochemistry and Agriculture, Oxford University Press, pp. 18–39.

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Insect Antifeedants

839

SALANNOL ACETATE

C34H46O9 (598.73)

Gummy material [α]D : +118° (CHCl3)

O O O

O O H

O AcO H

O

(1, 2)

(1, 2) SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf disk choice test

Conc. / Dose 0.00085%

Efficacy

Remarks

Feeding inhibition = 50.0%

1. Treatment to 4th stadium larvae for up to 24 h. Data calculated from Reference 2. EC50 = 9 ppm (2)

2. Popillia japonica Newman (Japanese beetle)

Leaf disk choice test

260 ppm

Feeding inhibition = 50.0%

2. Treatment to larvae. Concentration = EC50 value. (3)

(1) Rajatkar, S.R., Bhat, V.S., Kulkarni, M.M., Joshi, V.S., and Nagasampagi, B.A. (1989) Phytochemistry, 28, 203. (2) Champagne, D.E., Koul, O., Isman, M.B., Scudder, G.G.E., and Towers, G.H.N. (1992) Phytochemistry, 31, 377. (3) Kraus, W. (2002) In H. Schmutterer (ed.), The Neem Tree, 2nd edition, Neem Foundation, Mumbai, India, pp. 39–111.

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840

Opender Koul

SALANNOLACTAM–I

C34H45O9N (611.73)

O

M.p. : 213° [α]20 D : 121.8° (CH2Cl2)

O

O

NH

O H

O O

AcO H

O

(1)

(1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf disk choice test

Conc. / Dose 0.01%

Efficacy

Remarks

Activity better than salannins

Treatment to 4th stadium larvae for up to 24 h.

Activity refers to about 95% inhibition

No quantitative data reported. (2)

(1) Kraus, W., Klenk, A., Bokel, M., and Vogler, B. (1987) Liebigs Ann. Chem., 337. (2) Kraus, W., Baumann, S., Bokel, M., Keller, U., Klenk, A., Klingele, M., Pohnl, H., and Schwinger, M. (1987) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 3rd Int. Neem Conf., Nairobi, Kenya, GTZ, Eschborn, Germany, pp. 111–125.

© 2005 by CRC Press LLC

Insect Antifeedants

SALANNOLACTAM–II

841

C34H45O9N (611.73)

[α]20 D : 126.3° (CH2Cl2)

O

O

O NH

O O H

O AcO H

O

(1)

(1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf disk choice test

Conc. / Dose 0.01%

Efficacy

Remarks

Activity better than salannins.

Treatment to 4th stadium larvae for up to 24 h.

Activity refers to about 95% inhibition

No quantitative data reported. (2)

(1) Kraus, W., Klenk, A., Bokel, M., and Vogler, B. (1987) Liebigs Ann. Chem., 337. (2) Kraus, W., Baumann, S., Bokel, M., Keller, U., Klenk, A., Klingele, M., Pohnl, H., and Schwinger, M. (1987) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 3rd Int. Neem Conf., Nairobi, Kenya, GTZ, Eschborn, Germany, pp. 111–125.

© 2005 by CRC Press LLC

842

Opender Koul

SALONITENOLIDE

C15H20O4 (264.32)

M.p. : 136° [α]20 D : 199.4° (MeOH)

OH

CH2

CH2OH

O O

(1, 2)

(1, 2)

SOURCE: Centaurea salonitana Vis., tumbleweed (Asteraceae)

(3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

2. Tribolium confusum Duv. (Confused flour beetle)

3. Trogoderma granarium Everts (Khapra beetle)

Test Insect

Efficacy

Remarks

8 mg/cm3

Feeding deterrence coefficient = 51–100

1. Treatment given to adults.

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient: Adults = 51–100 Larvae = 51–100

2. Treatment given to both adults and larvae.

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Suchy, M., Samek, Z., Herout, V., and Sorm, F. (1967) Collect. Czeck. Chem. Commun., 32, 2016. (2) Yoshioka, H., Renold, W., and Mabry, T.J. (1970) Chem. Commun., 148. (3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst., Ochr. Roslin, 24, 27.

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Insect Antifeedants

SAMADERINE–B

843

C19H22O7 (362.38)

M.p. : 235–240° [α]D : +67.5° (pyridine)

O HO

HO O

O

O H

O H

(1, 2)

(1)

SOURCE: Samadera indica Gaertn., niepa bark tree (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Leaf disk choice test

19.8 µg/cm2

12.0 µg/cm2

Efficacy Feeding deterrence = 60–90% after 2 days and 30–60% after 6 days of treatment

Remarks Treatment to 3rd instar larvae. (2)

Feeding deterrence = 60–90% after 2 days and 0–30% after 6 days of treatment

(1) Zylber, J. and Polonsky, J. (1964) Bull. Soc. Chim. Fr., 2016. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

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844

Opender Koul

SANDARACOPIMARIC ACID

C20H30O2 (302.46)

M.p. : 171–173° (softens at 163°) [α]D : –20° (CHCl3)

CH2

COOH

(1, 2)

(1)

SOURCE: Cryptomeria japonica D. Don., Japanese cedar (Taxodiaceae), also isolated from Pinus, Juniperus, Cupressus, and Calltris spp.

(1)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 0.1%

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to aphids at random. (2)

(1) Bohlmann, F. and le Van, N. (1976) Chem. Ber., 109, 1446. (2) Rose, A.F., Jones, K.C., Halden, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

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Insect Antifeedants

SANDORICIN

845

C31H40O11 (588.65) O

O

M.p. : 215–217°

O

O

O O

O O

CH2

OH

COOCH3

(1)

(1)

SOURCE: Sandoricum koetjape (Burm. F.) Merr., santol (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Artificial diet dual-choice assay

25 ppm

Feeding deterrence = 57.0%

1. Treatment to newly hatched larvae for 16–20 h.

2. Ostrinia nubilalis (Hubner) (European corn borer)

Artificial diet dual-choice assay

200 ppm

Feeding deterrence = 66.0%

2. Treatment to newly hatched larvae for 16–20 h. Data calculated from Reference 1. (1)

(1) Powell, R.G., Mikolajczak, K.L., Zilkowski, B.W., Mantus, E.K., Cherry, D., and Clardy, J. (1991) J. Nat. Prod., 54, 241.

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846

Opender Koul

SANTONIN

C15H18O3 (246.31)

M.p. : 174–176° [α]18 D : –173° (EtOH)

O O O

(1, 2)

(1)

SOURCE: Product of British drug houses Helianthus annuus L., sunflower (Asteraceae)

(2) (3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 51–100

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient: Adults = 51–100 Larvae = 51–100

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (2)

4. Diabrotica virgifera virgifera LeConte (Western corn rootworm)

Leaf disk choice test

40 µg/1.5 cm2

Feeding deterrence = 79.0%

4. Treatment to adults for 5 h.

LD50 (mice): 900 mg/kg (oral)

(3)

(4)

(1) Clemo, G.R. and Haworth, R.D. (1930) J. Chem. Soc., 2579. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst., Ochr. Roslin, 24, 27. (3) Mullin, C.A., Mason, C.H., Chou, J., and Linderman, J.R. (1992) In C.A. Mullin and J.G. Scott (eds.), Molecular Mechanism of Insecticidal Resistance: Diversity Among Insects, ACS Symp. Ser. 505, Washington, D.C., pp. 288–308. (4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

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Insect Antifeedants

8-β-SARRACINOYLOXYCUMAMBRANOLIDE

847

C20H26O6 (362.42) M.p. : 129–130°

OH OH

O

O CH2

O

O

(1, 2)

(1)

SOURCE: Helianthus maximillani Schrader, perennial sunflower (Asteraceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera eridania (Cramer) (Southern armyworm)

Test Method Leaf coating

Conc. / Dose 1.0%

Efficacy Feeding deterrence = 44.0%

Remarks 1. Treatment to starved 5th instar larvae. Data calculated from Reference 2. (2)

2. Melanoplus sanguinipes (Fab.) (Migratory grasshopper)

Filter disk test

0.25% per dry weight of disk

0.30 ± 0.46 cm2 of control disk eaten in excess of test disk

2.5% per dry weight of disk

1.19 ± 0.99 cm2 of control disk eaten in excess of test disk

2. Treatment to starved grasshoppers for 48 h. (2)

(1) Gershenzon, J. and Mabry, T.J. (1984) Phytochemistry, 23, 1959. (2) Gershenzon, J., Rossiter, M., Mabry, T.J., Rogers, C.E., Blust, M.H., and Hopkins, T.L. (1985) ACS Symp. Ser. 276, 433.

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848

Opender Koul

SCABEQUINONE

C15H16O4 (260.29)

M.p. : 108–110°

O

O

O O

(1)

(1)

SOURCE: Cyperus nipponicus, C. distans L., sedge (Cyperaceae)

(1)

ACTIVITY PROFILE Test Insectt Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk assay

Conc. / Dose

Efficacy

2.6 × 10–9 mol/cm2

Feeding inhibition = 50.0%

Remarks Treatment to 3rd instar larvae up to 5 h. Concentration = EC50 value. (1)

(1) Morimoto, M., Fujii, Y., and Komai, K. (1999) Phytochemistry, 51, 605.

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Insect Antifeedants

SCHKUHRIN–I

849

C22H28O8 (420.46)

M.p. : 59–61° [α]D : –121° (CHCl3)

O H O O

CH2

OH

(1, 2)

(1) SOURCE: Schkuhria pinnata (Lam.) O. Kuntze canchalagua (Asteraceae)

(1)

ACTIVITY PROFILE Test Insectt

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Leaf disk test

Absolute feeding deterrence

Treatment given to larvae.

2. Epilachna varivestis Muls. (Mexican bean beetle)

Leaf disk test

Absolute feeding deterrence

No quantitative data recorded. (1)

(1) Pettei, M.J., Miura, I., Kubo, I., and Nakanishi, K. (1978) Heterocycles, 11, 471. (2) Dictionary of Natural Products (1994) Chapman & Hall, London.

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850

Opender Koul

SCHKUHRIN–II

C25H34O9 (478.54)

M.p. : 65–66°

O

OC

H

AcO CH2OH

CH2OH CH2

O

O

(1)

(1)

SOURCE: Schkuhria pinnata (Lam.) O. Kuntze, canchalagua (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Leaf disk test

Absolute feeding deterrence

Treatment given to larvae.

2. Epilachna varivestis Muls. (Mexican bean beetle)

Leaf disk test

Absolute feeding deterrence

No quantitative data recorded. (1)

(1) Pettei, M.J., Miura, I., Kubo, I., and Nakanishi, K. (1978) Heterocycles, 11, 471.

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Insect Antifeedants

851

SCHKUHRIOLIDE

C15H18O4 (262.31)

M.p. : 155–157° [α]20 D : + 84.6° (MeOH)

O O OH

H

OC O H

CH2OH

CH2OH

O

CH2 O

(1, 2) (1) SOURCE: Schkuhria schkuhrioides (Link et Otto) Thell., mountain weed (Asteraceae)

(2)

ACTIVITY PROFILE Test Insectt

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 99.5

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient: Adults = 88.6 Larvae = 98.0

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 98.9

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Samek, Z., Holub, M., Bloszyk, E., and Drozdz, B. (1979) Z. Chem., 19, 449. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk. Inst., Ochr. Roslin, 25, 91

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852

Opender Koul

SCUTALBIN–C

C22H32O8 (424.49)

M.p. : 133–138°

OH

[α]20 D : –6.8° (MeOH) O

O

O O OAc OH

(1, 2)

(2)

SOURCE: Scutellaria rubicunda Hornem subsp. Linneana Carnel, skullcap (Labiatae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to starved final stadium larvae (24–36 h old). Bioassays terminated after the larvae had eaten approximately 50% of one of the disks. (1)

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk choice test

100 ppm

Feeding inhibition = 32.0%

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk choice test

100 ppm

Feeding inhibition = 32.0%

3. Mamestra brassicae (L.) (Cabbage moth)

Glass fiber disk choice test

100 ppm

Feeding inhibition = 41.0%

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Glass fiber disk choice test

100 ppm

Feeding inhibition = 14.0%

5. Pieris brassicae (L.) (Large white butterfly)

Glass fiber disk choice test

100 ppm

Feeding inhibition = 12.0%

(1) Bruno, M., Vassallo, N., and Simmonds, M.S.J. (1999) Phytochemistry, 50, 973. (2) Bruno, M., Piozzi, F., Rodriguez, B., de la Torre, M.C., Vassallo, N., and Servettaz, O. (1996) Phytochemistry, 42, 1059.

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Insect Antifeedants

SCUTALPIN–C

853

C27H38O9 (506.59)

M.p. : 156–158° [α]20 D : +5° (CHCl3)

O HO O O

O O

OH

O

O

(1)

(1)

SOURCE: Scutellaria alpina javalambrensis Pau. alpine skullcap (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Glass fiber disk choice test

Conc. / Dose 100 ppm

Efficacy

Remarks

Feeding inhibition = 96.8%

Treatment to 24- to 36-h-old final stadium larvae until 50% of the disks were eaten. Larvae pre-starved for 4 h. (2)

(1) De la Torre, M.C., Rodriguez, B., Bruno, M., Malakov, P.Y., Papanov, G.Y., Piozzi, F., and Savona, G. (1993) Phytochemistry, 34, 1589. (2) Munoz, D.M., de la Torre, M.C., Rodriguez, B., Simmonds, M.S.J., and Blaney, W.M. (1997) Phytochemistry, 44, 593.

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854

Opender Koul

SCUTECYPROL–B

C27H38O9 (506.59)

OH

Only spectral data given

O

O

O O OAc OCO

(1)

(1)

SOURCE: Scutellaria rubicunda Hornem subsp. Linneana Carnel., skullcap (Labiatae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to starved final stadium larvae (24–36 h old). Bioassays terminated after the larvae had eaten approximately 50% of one of the disks. (1)

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk choice test

100 ppm

Feeding inhibition = 100.0%

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk choice test

100 ppm

Feeding inhibition = 85.0%

3. Mamestra brassicae (L.) (Cabbage moth)

Glass fiber disk choice test

100 ppm

Feeding inhibition = 86.0%

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Glass fiber disk choice test

100 ppm

Feeding inhibition = 65.0%

5. Pieris brassicae (L.) (Large white butterfly)

Glass fiber disk choice test

100 ppm

Feeding inhibition = 75.0%

(1) Bruno, M., Vassallo, N., and Simmonds, M.S.J. (1999) Phytochemistry, 50, 973.

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Insect Antifeedants

SCUTEGALIN–A

855

C32H44O10 (588.69)

M.p. : 105–110° [α]23 D : +17° (CHCl3)

O

O O

O

O O O O

O

O

(1) (1) SOURCE: Scutellaria galericulata L., blue skullcap (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Glass fiber disk choice test

Conc. / Dose 100 ppm

Efficacy

Remarks

Feeding inhibition = 41%

Treatment to 24- to 36-h-old final stadium larvae until 50% of the disk was eaten. Larvae prestarved for 4 h. (1)

(1) Rodriguez, B., de la Torre, M.C., Rodriguez, M., Bruno, M., Piozzi, F., Savona, G., Simmonds, M.S.J., Blaney, W.M., and Perales, A. (1993) Phytochemistry, 33, 309.

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856

Opender Koul

SENECIOIC ACID

C5H8O2 (100.12)

M.p. : 70° B.p. : 199°

COOH

(1)

(1)

SOURCE: Alchornea triplinervia (Spreng.) Muell. Arg., tapia (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Anthonomus grandis Bohem. (Boll weevil)

LD50 (rats): 3560 mg/kg (oral)

Test Method Artificial diet feeding

Conc. / Dose

Efficacy

Remarks

10 mg/4 cm2

Feeding deterrence = 15%

15 mg/4 cm2

Feeding deterrence = 17%

40 mg/4 cm2

Feeding deterrence = 2%

Treatment given to freshly emerged boll weevils. Ratio value of 0 represents absolute antifeedant effect and >100 = attraction. (2)

(3)

(1) Dictionary of Organic Compounds (1994) Chapman & Hall, London. (2) Miles, D.H., Hankinson, B.L., and Randle, S.A. (1985) Proc. ACS Symp. Ser., 276, 469. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

SENECIONINE

857

C18H25O5N (335.40)

[α]D : –54.6° (CHCl3)

H

H2C

C

C

C C

C H O

M.p. : 232–233°

C

OH H

O

O

O CH2

N

(1, 2)

(1, 2)

SOURCE: Senecio anonymous, groundsel (Asteraceae) Senecio triangularis, groundsel (Asteraceae)

(3) (4)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Choristoneura fumiferana (Clemens) (Spruce budworm)

Paper penicillin disk assay

2. Acyrthosiphon pisum (Harris) (Pea aphid)

Artificial diet feeding

Test Insect

Efficacy

Remarks

1.6 × 103 M

Feeding deterrence = 36.0%

1. Treatment to 6th instar larvae. (3)

0.17 ± 0.05%

Feeding deterrence = 50.0%

2. Treatment to aphids at random.

LD50 (rats): 85.0 mg/kg (ipr.) (1) (2) (3) (4) (5)

Manske, R.H.F. (1931) Can. J. Res., 5, 651. Manske, R.H.F. (1939) Can. J. Res., 17B, 1. Bentley, M.D., Leonard, D.E., Stoddard, W.F., and Zalkow, L.H. (1984) An. Entomol. Soc. Am., 77, 393. Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045. Cordell, G.A. (1981) Introduction to Alkaloids, John Wiley & Sons, New York, p. 134.

© 2005 by CRC Press LLC

(4)

(5)

858

Opender Koul

6α-SENECIOYLOXY CHAPARRINONE (structure under review)

C25H32O9 (476.52) OH

M.p. : 255–257° [α]25 D : +213° (pyridine)

HO HO

O

O

O

H

O

H OOC

(1, 2) (1) SOURCE: Simaba multiflora A. Juss., cajurana (Simaroubaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Heliothis virescens (Fab.) (Tobacco budworm)

Test Method Leaf disk choice test

Conc. / Dose 15 µg/cm2

Efficacy Feeding deterrence = 95.0%

Remarks 1. Treatment to 3rd instar larvae. Concentration = 95% protection concentration. (2)

2. Spodoptera frugiperda (J. E. Smith) (Fall armyworm)

Leaf disk choice test

8 µg/cm2

Feeding deterrence = 95.0%

2. Treatment to 3rd instar larvae. Concentration = 95% protection concentration. (2)

(1) Arisawa, M., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1983) J. Nat. Prod., 46, 218. (2) Klocke, J.A., Arisawa, M., Handa, S.S., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1985) Experientia, 41, 7.

© 2005 by CRC Press LLC

Insect Antifeedants

SENECIPHYLLINE

859

C18H23O5N (333.38)

M.p. : 217–218° (dec.) [α]17 D : –139° (CHCl3)

OH O

O

O

H

CH2

O

N

(1, 2)

(1)

SOURCE: Senecio douglasii var. longilobus, groundsel (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Acyrthosiphon pisum (Harris) (Pea aphid)

Test Method

Conc. / Dose

Artificial diet feeding

0.04 ± 0.006%

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to aphids at random. Concentration = EC50 value. (2)

LD50 (rats): 77.0 mg/kg (ipr.) (1) Bradbury, R.B. and Culvenor, C.C.J. (1954) Aust. J. Chem., 7, 378. (2) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045. (3) Mattocks, A.R. (1986) Chemistry and Toxicology of Pyrrolizidine Alkaloids, Academic Press, New York.

© 2005 by CRC Press LLC

(3)

860

Opender Koul

SENKIRKINE

C19H27O6N (365.43) H

C

[α]25 D : –16° (MeOH) H2C

C

C C

C H

O

M.p. : 196.5–197.5°

C

OH

O

O

O CH2

O

N

(1, 2)

(1)

SOURCE: Tussilago farfara L., colts foot (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Choristoneura fumiferana (Clemens) (Spruce budworm)

LD50 (rats): 220 mg/kg (ipr.)

Test Method Paper penicillin disk assay

Conc. / Dose 0.2 × 103 M

Efficacy Feeding deterrence = 44.0%

Remarks Treatment to 6th instar larvae. (2)

1.0 × 103 M

Feeding deterrence = 68.0%

5.0 × 103 M

Feeding deterrence = 89.0%

FI50 = 0.31 × 103 M Calculated from Reference 2.

(3)

(1) Briggs, L.H., Cambie, R.C., Candy, B.J., Donovan, G.M., Russel, R.H., and Sedye, R.N. (1965) J. Chem. Soc., 2492. (2) Bentley, M.D., Leonard, D.E., Stoddard, W.F., and Zalkow, L.H. (1984) An. Entomol. Soc. Am., 77, 393. (3) Mattocks, A.R. (1986) Chemistry and Toxicology of Pyrrolizidine Alkaloids, Academic Press, New York.

© 2005 by CRC Press LLC

Insect Antifeedants

SERGEOLIDE

861

C25H28O11 (504.49)

M.p. : 202–206° [α]22 D : –103.3° (MeOH)

OH HO

COOCH3 O OCOCH3

O O

H O

O

H

(1, 2)

(1)

SOURCE: Picrolemma pseudocoffea Ducke (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Leaf disk choice test

12.0 µg/cm2

Efficacy Feeding deterrence = 90–100% after 6 days of treatment

6.0 µg/cm2

Feeding deterrence = 90–100% after 2 days and 60–90% after 6 days of treatment

3.0 µg/cm2

Feeding deterrence = 90–100% after 2 days and 30–60% after 6 days of treatment

Remarks Treatment to 3rd instar larvae. (2)

(1) Moretti, C., Polonsky, J., Vuilhorgne, M., and Prange, T. (1982) Tetrahedron Lett., 23, 647. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

862

Opender Koul

SEVERINOLIDE

C31H38O11 (586.63) O

M.p. : 219–221° [α]D : +53.08° (CHCl3)

O OCH3 O

O

O

O

OAc OAc

(1)

(1)

SOURCE: Severinia buxifolia (Poir.) Tenore., Chinese box orange (Rutaceae)

(1)

ACTIVITY PROFILE Test Insect Plutella xylostella (L.) (Diamondback moth)

Test Method

Conc. / Dose

Leaf disk choice test

0.0625%

Efficacy Feeding deterrence = 50.0%

Remarks Treatment to 3rd instar larvae. Concentration = EC50 value. (1)

(1) Wu, T.S., Leu, Y.L., Chan, Y.Y., Wu, P.L., Kuoh, C.S., Wu, S.J., and Wang, Y. (1997) Phytochemistry, 45, 1393.

© 2005 by CRC Press LLC

Insect Antifeedants

SHIROMODIOL DIACETATE

863

C19H30O5 (338.44)

M.p. : 109–112° [α]25 D : –61.9° (CHCl3)

OCOCH3

O OCOCH3

(2)

(1, 2) SOURCE: Parabenzoin trilobum Nakai, Japanese shiromoji (Lauraceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Trimeresia miranda Butler (Borneo moth)

Test Method Leaf disk choice test

Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

0.5%

Feeding deterrence = 94.0%

1. Treatment to 3rd instar larvae.

0.25%

Feeding deterrence = 86.0%

Data calculated from Reference 1. (1)

0.25%

Feeding deterrence = 100%

2. Treatment to 3rd instar larvae.

0.03%

Feeding deterrence = 70.0%

Data calculated from Reference 1. (1)

(1) Wada, K., Matsui, K., Enomoto, Y., Ogiso, O., and Munakata, K. (1970) Agric. Biol. Chem., 34, 941. (2) Wada, K., Enomoto, Y., and Munakata, K. (1970) Agric. Biol. Chem., 34, 946.

© 2005 by CRC Press LLC

864

Opender Koul

SHIROMODIOL MONOACETATE

C17H28O4 (296.41)

M.p. : 78–80° [α]25 D : –44.8° (CHCl3)

OCOCH3

O OH

(1, 2)

(2)

SOURCE: Parabenzoin trilobum Nakai, Japanese shiromoji (Lauraceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Trimeresia miranda Butler (Borneo moth)

Test Method Leaf disk choice test

Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

0.5%

Feeding deterrence = 100%

1. Treatment to 3rd instar larvae.

0.25%

Feeding deterrence = 70.0%

Data calculated from Reference 1. (1)

0.25%

Feeding deterrence = Approx. 70.0%

2. Treatment to 3rd instar larvae. Data calculated from Reference 1. (1)

(1) Wada, K., Matsui, K., Enomoto, Y., Ogiso, O., and Munakata, K. (1970) Agric. Biol. Chem., 34, 941. (2) Wada, K., Enomoto, Y., and Munakata, K. (1970) Agric. Biol. Chem., 34, 946.

© 2005 by CRC Press LLC

Insect Antifeedants

SHIROMOOL

865

C15H26O2 (238.37)

M.p. : 72–73° [α]25 D : +85.5° (CHCl3)

O OH

(1, 2)

(2)

SOURCE: Parabenzoin trilobum Nakai, Japanese shiromoji (Lauraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

0.5%

Feeding deterrence = 97.0%

Treatment to 3rd instar larvae.

0.25%

Feeding deterrence = 44.0%

Data calculated from Reference 1. (1)

(1) Wada, K., Matsui, K., Enomoto, Y., Ogiso, O., and Munakata, K. (1970) Agric. Biol. Chem., 34, 941. (2) Wada, K., Enomoto, Y., and Munakata, K. (1970) Agric. Biol. Chem., 34, 946.

© 2005 by CRC Press LLC

866

Opender Koul

SHOREIC ACID

C30H50O4 (474.72) M.p. : 92–94°

H OH

[α]D : +40° (Me ester) O

HOOC H2C

(1, 3)

(1, 2) SOURCE: Dysoxylum malabaricum Bedd. and ex C.DC. white cidar (Meliaceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk dualchoice test

Conc. / Dose

Efficacy

Remarks

1.0 µg/cm2

Feeding deterrence = 51.8%

Treatment to 3rd instar larvae for 24 h.

5.0 µg/cm2

Feeding deterrence = 55.8%

EC50 = 0.76 µg/cm2

10.0 µg/cm2

Feeding deterrence = 74.6%

50.0 µg/cm2

Feeding deterrence = 75.5%

Data calculated from Reference 2. (2)

(1) Govindachari, T.R., Suresh, G., and Krishna Kumari, G.N. (1994) Phytochemistry, 37, 1127. (2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari, G.N. (1995) J. Chem. Ecol., 21, 1586. (3) Lantz, J.-P. (1968) Bull. Soc. Chim. Fr., 2131

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Insect Antifeedants

SIDEROXOL

867

C20H32O3 (320.47)

M.p. : 245–246°

O OH OH

(1, 2)

(1, 2)

SOURCE: Sideritis akmanii L., iron-wort, also from S. niveotomentosa, S. rubiflora (Labiatae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera littoralis (Boisd.) (Tobacco armyworm)

Glass fiber disk test

100 ppm

Feeding deterrence = 50%

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk test

100 ppm

Feeding deterrence = 50%

Test Insect

Efficacy

Remarks Treatment to final instar larvae. (2)

(1) Piozzi, F., Venturella, P., Bellino, A.C., and Mendelli, R. (1968) Ric. Sci., 38, 462. (2) Bondi, M.L., Bruno, M., Piozzi, F., Husnu, K., Baser, C., and Simmonds, M.S.J. (2000) Biochem. Syst. Ecol., 28, 299.

© 2005 by CRC Press LLC

868

Opender Koul

SILPHINEN-3,5-DIONE

C15H20O2 (232.15)

Oil Only spectral data given

O

O

(1)

(1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Choice feeding assay

>100 nmol/cm2

Feeding deterrence = 50.0%

1. Treatment to 6th instar larvae.

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Choice feeding assay

4.82 nmol/cm2

Feeding deterrence = 50.0%

2. Treatment to adults.

3. Myzus persicae (Sulzer) (Green peach aphid)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

3. Treatment to apterous adult aphids.

4. Rhopalosiphum padi (L.) (Cereal aphid)

Choice feeding assay

>150 nmol/cm2

Feeding deterrence = 50.0%

4. Treatment to apterous adult aphids.

5. Sitobion avenae (Fab.) (Grass aphid)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

5. Treatment to apterous adult aphids.

6. Diuraphis noxia (Mordvilko) (Wheat aphid)

Choice feeding assay

25.6 nmol/cm2

Feeding deterrence = 50.0%

6. Treatment to apterous adult aphids.

Test Insect

Efficacy

Remarks

Concentrations = EC50 value. (1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.

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Insect Antifeedants

SILPHINEN-3,5,11-TRIONE

869

C15H18O3 (246.13)

Oil

O

O

O

(1)

(1)

SOURCE: Semisynthetic

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis Boisd. (Egyptian cotton leaf worm)

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

3. Diuraphis noxia (Mordvilko) (Wheat aphid)

Test Method

Conc. / Dose

Choice leaf disk feeding assay

42.4 nmol/cm2

Choice leaf disk feeding assay

>100 nmol/cm2

Choice feeding assay

>200 nmol/cm2

Efficacy

Remarks

Feeding deterrence = 50.0%

1. Treatment to 6th instar larvae for 24 h. Concentration = EC50 value.

Feeding deterrence = 50.0%

2. Treatment to adults for 24 h. Concentration = EC50 value.

Feeding deterrence = 50.0%

3. Treatment to adults for 24 h.

Feeding deterrence = 75.5%

Concentration = EC50 value. (1)

(1) Gonzalez-Coloma, A., Valencia, F., Martin, N., Hoffmann, J.J., Hutter, L., Marco, J.A., and Reina, M. (2002) J. Chem. Ecol., 28, 117.

© 2005 by CRC Press LLC

870

Opender Koul

SILYBIN

C25H22O10 (482.44)

M.p. : 167° [α]20 D : +11° (Me2CO)

OH

O OH

OH

O OCH3

O

HO

O

CH2OH

(1, 2)

(1, 2) SOURCE: Silybum marrianum (L.) Gaertn., blessed thistle (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Peridroma saucia (Hubner) (Variegated cutworm)

Test Method

Conc. / Dose

Leaf disk choice test

Efficacy

Remarks

28.5 µg/cm2

Feeding deterrence = 29.3%

Treatment to 5th instar larvae for 5 h. (2)

57.0 µg/cm2

Feeding deterrence = 58.9%

(1) Pelter, A. and Haensel, R. (1975) Chem. Ber., 108, 790. (2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.

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Insect Antifeedants

SIMALIKALACTONE–A

871

C22H32O6 (392.49)

M.p. : 278.5° [α]D : +17° (EtOH)

OCH3 HO O H3CO H O

O

(1, 2)

(1, 2) SOURCE: Picrasma ailanthoides Planchon., quassia (Simaroubaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Heliothis virescens Fab. (Tobacco budworm)

Test Method Leaf disk choice test

Conc. / Dose 19.8 µg/cm2

Efficacy Feeding deterrence = 60–90% after 2 days and 30–60% after 6 days of treatment

12.0 µg/cm2

Feeding deterrence = 60–90% after 2 days and 0–30% after 6 days of treatment

3.0 µg/cm2

Feeding deterrence = 60–90% after 2 days and 0–30% after 6 days of treatment

Remarks Treatment to 3rd instar larvae. (3)

(1) Murae, T., Tsuyuki, T., Ikeda, T., Nishihama, T., Masuda, S., and Takahashi, T. (1971) Tetrahedron, 27, 1545. (2) Tresca, J.-P., Alais, L., and Polonsky, J. (1971) Compt. Rend., 273C, 601. (3) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

872

Opender Koul

SIMALIKALACTONE–D

C25H34O9 (478.54)

M.p. : 228–230° [α]D : +53°

OH HO HO O OCO

O

H O

O

(1, 2)

(1)

SOURCE: Quassia africana Baillon, African otapaa (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Epilachna varivestis Muls. (Mexican bean beetle)

Test Method

Conc. / Dose

Whole leaf application

200 ppm

Efficacy

Remarks

Feeding deterrence = 85.5%

1. Treatment to 4th instar larvae for 24 h. Larvae pre-starved for 2 h. Data calculated from Reference 2. (2)

2. Spodoptera eridania (Cramer) (Southern armyworm)

Whole leaf application

200 ppm

Feeding deterrence = 89.2%

2. Treatment to 5th instar larvae for 24 h. Larvae pre-starved for 2 h. Data calculated from Reference 2. (2)

(1) Tresca, J.-P., Alais, L., and Polonsky, J. (1971) Compt. Rend., 273C, 601. (2) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

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Insect Antifeedants

SIMAROLIDE

873

C27H36O9 (504.58)

M.p. : 264–270° [α]D : +73.6° (CHCl3)

O H3CCOO O O HO O

H O

O

(1, 2)

(1, 2)

SOURCE: Simarouba amara Aubl., bitter damson (Simaroubaceae)

(1,3)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Heliothis virescens (Fab.) (Tobacco budworm)

Leaf disk choice test

2. Epilachna varivestis Muls. (Mexican bean beetle)

Whole leaf application

Test Insect

Efficacy

Remarks

19.8 µg/cm2

Feeding deterrence = 30–60% after 2 days and 0–30% after 6 days of treatment

1. Treatment to 3rd instar larvae. (3)

500 ppm

Feeding deterrence = 83.3%

2. Treatment to 4th instar larvae for 24 h. Larvae pre-starved for 2 h. Data calculated from Reference 4. (4)

(1) Polonsky, J. (1959) Bull. Soc. Chim. Fr., 1546. (2) Polonsky, J. (1964) Proc. Chem. Soc., 292. (3) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442. (4) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC

874

Opender Koul

SINAPIC ACID

C11H12O5 (224.21)

M.p. : 192°

COOH

H3CO

OCH3 OH

(1, 2, 3)

(1, 2)

SOURCE: Commercial sample

(3)

ACTIVITY PROFILE Test Insect Pieris brassicae (L.) (Large white butterfly)

Test Method

Conc. / Dose

Leaf disk no-choice test

4.4 × 10–2 M

Efficacy Feeding deterrence ratio = 2.36

Remarks Treatment to 2nd day 5th instar unstarved larvae. Ratio between 0 and 20 effective deterrence. (3)

(1) Spath, E. (1920) Monatsh. Chem., 41, 271. (2) Bate-Smith, E.C. (1956) Sci. Proc. R. Dublin Soc., 27, 165. (3) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.

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Insect Antifeedants

SINIGRIN

875

C10H17O9NS2 (359.38)

No physical data given

O

O S

M.p. : 125–127° (for potassium salt)

OH

O N

S HO O OH HO OH

(1, 2)

(1, 2)

SOURCE: Commercial sample Present in many crucifers (major glucosinolate in Brassica oleracea L., Brassicaceae)

(3)

ACTIVITY PROFILE Test Insect Locusta migratoria (L.) (Migratory locust)

Test Method Wafer disk choice test

Conc. / Dose

Efficacy

Remarks

0.05% dry weight

Feeding deterrence = 50%

Treatment to 3-dayold 5th instar nymphs for 3–4 h. (3)

(1) Benn, M.H. and Ettlinger, M.G. (1965) Chem. Commun., 445. (2) Matsuo, M. (1968) Tetrahedron Lett., 4101. (3) Bernays, E.A. and Chapman, R.F. (1977) Ecol. Entomol., 2, 1.

© 2005 by CRC Press LLC

876

Opender Koul

SOLANIDINE

C27H43ON (397.65)

M.p. : 218–219° [α]21 D : –29° (CHCl3)

N

HO

(1)

(1, 2) SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Choristoneura fumiferana (Clemens) (Spruce budworm)

Test Method Paper penicillin disk assay

Conc. / Dose 10–3 M

Efficacy Feeding deterrence = 94.0%

Remarks Treatment to 6th instar larvae. (2)

10–4 M

Feeding deterrence = 74.0%

(1) Reichstein, T. and Reich, H. (1946) Ann. Rev. Biochem., 15, 155. (2) Bentley, M.D., Leonard, D.E., and Bushway, R.J. (1984) Ann. Entomol. Soc. Am., 77, 401.

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Insect Antifeedants

α-SOLANINE

877

C45H73O15N (868.07)

M.p. : 285° (dec.) [α]20 D : –60° (pyridine)

N

Rham-glu-gal-O

(1, 2)

(1)

SOURCE: Solanum species (Solanaceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Choristoneura fumiferana (Clemens) (Spruce budworm)

Paper penicillin disk assay

10–3 M

Feeding deterrence = 59.0%

1. Treatment to 6th instar larvae. (2)

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Sensillum response recording

0.4% wet weight

Feeding deterrence = 50.0%

2. Treatment to adult beetles. Concentration = EC50 value. (3)

LD50 (mice): 42 mg/kg (i.p.) (1) Kuhn, R. and Low, I. (1954) Angew. Chem., 66, 639. (2) Bentley, M.D., Leonard, D.E., and Bushway, R.J. (1984) Ann. Entomol. Soc. Am., 77, 401. (3) Mitchell, B.K. and Harrison, G.D. (1985) J. Chem. Ecol., 11, 73.

© 2005 by CRC Press LLC

(3)

878

Opender Koul

SOULAMEANONE

C20H28O8 (396.44)

M.p. : 263–265° [α]22 D : +101° (MeOH/CHCl3, 2:1)

OH HO HO OH O

OH

O

O

(1, 2)

(1)

SOURCE: Soulamea muelleri Brongn. & Gris (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Epilachna varivestis Muls. (Mexican bean beetle)

Test Method

Conc. / Dose

Whole leaf application

500 ppm

Efficacy

Remarks

Feeding deterrence = 10.0%

1. Treatment to 4th instar larvae for 24 h. Larvae pre-starved for 2 h. Data calculated from Reference 2. (2)

2. Spodoptera eridania (Cramer) (Southern armyworm)

Whole leaf application

500 ppm

Feeding deterrence = 50.0% in one case only

2. Treatment to 5th instar larvae for 24 h. Larvae pre-starved for 2 h. Data calculated from Reference 2. (2)

(1) Polensky. J., Tri, M.V., Varon, Z., Prange, T., Pascard, C., Sevenet, T., and Pusset, J. (1980) Tetrahedron, 36, 2983. (2) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC

Insect Antifeedants

SOULAMEOLIDE

879

C25H32O8 (460.52)

M.p. : 261–263° [α]22 D : –72.6° (MeOH)

CH2OH

HO

O

HO

O H

O H O

O

H

(1, 2)

(1)

SOURCE: Soulamea tomentosa Brongn. & Gris (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method Leaf disk choice test

Conc. / Dose 19.8 µg/cm2

Efficacy Feeding deterrence = 30–60% after 2 days and 0–30% after 6 days of treatment

Remarks Treatment to 3rd instar larvae. (2)

(1) Polonsky, J., Tri, M.V., Prange, T., and Pascard, C. (1979) J. Chem. Soc. Chem. Commun., 641. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

880

Opender Koul

SPARTEINE

C15H26N2 (234.39)

B.p. : 173–174°/8 mm [α]21 D : –16.4° (EtOH)

H H N

N H H

(1, 2) (1, 2) SOURCE: Compound evaluated as a sulphate salt Lupinus polyphyllus Lindl., lupine (Fabaceae)

(3) (4)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose 1 mM

Efficacy

Remarks

Feeding deterrence = 42.9% Feeding deterrence = 100%

1. Treatment to 7- to 20-h-old 4th instar larvae. (3)

1. Entomoscelis americana Brown (Red turnip beetle)

Leaf disk dip test

2. Choristoneura fumiferana (Clemens) (Spruce budworm)

Paper penicillin disk assay

2.1 × 103 M

Feeding deterrence = Not active

2. Treatment to 6th instar larvae. (4)

3. Acyrthosiphon pisum (Harris) (Pea aphid)

Artificial diet feeding

0.00011 ± 0.00005%

Feeding deterrence = 50.0%

3. Treatment to aphids at random.

10 mM

(5) 4. Phormia regina (Meigen) (Blowfly)

LD50 (mouse): 26 mg/kg (ivn.)

Sucrose solution feeding

10 mM

Feeding deterrence = 91.0% after 6 h

4. Treatment to 2-, 4-, and 6-day-old adults after 24 h starvation. (6)

(7)

(1) Clemo, G.R., Leitch, G.C., and Raper, R. (1931) Ber., 64, 1520. (2) Clemo, G.R., Raper, R., and Short, W.S. (1949) J. Chem. Soc., 663. (3) Mitchell, B.K. and Sutcliffe, J.F. (1984) Physiol. Entomol., 9, 57. (4) Bentley, M.D., Leonard, D.E., Reynolds, E.K., Leach, S., Beck, A.B., and Murakoshi, I. (1984) Ann. Entomol. Soc. Am., 77, 398. (5) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045. (6) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299. (7) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

Insect Antifeedants

SPECIONIN

881

C20H26O8 (394.42)

Oil [α]D : –30.7° (CHCl3)

HO

COO OC2H5

O O CH2OH

OC2H5

(1, 2)

(1, 2)

SOURCE: Catalpa speciosa Warder ex Barney, catalpa (Bignoniaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Choristoneura fumiferana (Clemens) (Spruce budworm)

Test Method

Conc. / Dose

Artificial diet feeding

50–100 ppm

Efficacy

Remarks

Feeding deterrence = 100%

Treatment to larvae. (1)

(1) Chang, C.C. and Nakanishi, K. (1983) J. Chem. Soc. Chem. Commun., 605. (2) Vander Eycken, E., Bruyn, A. de, vander Eycken, J., Gallant, P., and Vandewalle, M. (1986) Tetrahedron, 19, 5385.

© 2005 by CRC Press LLC

882

Opender Koul

SPECIOSIDE

C24H28O12 (508.48)

M.p. : 244–245°

OH

[α]21 D : –203° (MeOH) OOC

H

O O H

HO O

HO

HO OH

O

OH

(1)

(1)

SOURCE: Catalpa speciosa Warder ex Barney, catalpa (Bignoniaceae)

(1)

ACTIVITY PROFILE Test Insect Lymantria dispar (L.) (Gypsy moth)

Test Method

Conc. / Dose

Artificial diet feeding

1.0 mg/ml

Efficacy Feeding deterrence = 27.0%

Remarks Treatment to 3rd instar larvae. (1)

(1) El-Naggar, S.F. and Doskotch, R.W. (1980) J. Nat. Prod., 43, 524.

© 2005 by CRC Press LLC

Insect Antifeedants

cis – SPIROENOL ETHER (Mycosinol)

883

C13H12O2 (200.23)

M.p. : 48.5–49.5° [α]D : –45.3° (EtOH)

O O

(1, 2)

(1, 2)

SOURCE: Chrysanthemum coronarium L., Japanese chrysanthemum (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Bombyx mori (L.) (Silkworm)

Test Method Artificial diet feeding

Conc. / Dose 4 µg/g

Efficacy

Remarks

Feeding deterrence = 100%

Treatment to male 5th instar larvae. (2)

(1) Bholmann, F., Arndt, C., Boronowski, H., Keine, K., and Herbst, P. (1964) Chem. Ber., 97, 1179. (2) Tada, M. and Chiba, K. (1984) Agric. Biol. Chem., 48, 1367.

© 2005 by CRC Press LLC

884

Opender Koul

25 RS-SPIROST-5EN-3β-OL,3-O [α-L-RHAMNOPYRANOSYL] [β-D-GLUCOPYRANOSYL,β-D-GLUCOPYRANOSYL] -13-D-GLUCOPYRANOSIDE

C51H83O22 (1048.20)

M.p. : 276–279° (dec.)

O

O

OH OH

OH

O O

O

O OH

O

OH

OH O

OH O

O OH HO

OH HO

(1)

OH

(1)

SOURCE: Balanites roxburghii Planch, date (Zygophyllaceae)

(1)

ACTIVITY PROFILE Test Insect Diacresia obliqua (Walker) (Hairy caterpillar)

Test Method Leaf disk test

(1) Jain, D.C. (1987) Phytochemistry, 26, 2223.

© 2005 by CRC Press LLC

Conc. / Dose 500 ppm

Efficacy

Remarks

Feeding deterrence = 68.0%

Treatment to larvae. (1)

Insect Antifeedants

STEARIC ACID

885

C18H36O2 (284.48)

M.p. : 69.7° B.p. : 386°

O

OH

(1, 2)

(1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae)

(2)

ACTIVITY PROFILE Test Method

Test Insect Incisitermes minor (Hagen) (Western drywood termite)

Paper towel disk test

Conc. / Dose

Efficacy

Remarks

0.25 mg/cm2

Feeding deterrence = 73.9% after 7-day exposure

0.05 mg/cm2

Feeding deterrence = 30.0% after 6-day exposure

Treatment to immature termites of 10–13 mg body weight. (2)

LD50 (rats): 21.5 ± 1.8 mg/kg (i.v.) (1) Dictionary of Natural Products (1994) Chapman & Hall, London. (2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. (3) Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

© 2005 by CRC Press LLC

(3)

886

Opender Koul

STEMOFOLINE

C22H29O5N (387.46)

M.p. : 87–89° [α]D : +273° (MeOH)

OCH3

N

O

O

O O

(2)

(1, 2) SOURCE: Stemona collinsae Craib (Stemonaceae)

(1)

ACTIVITY PROFILE Test Insect Plutella xylostella (L.) (Diamondback moth)

Test Method

Conc. / Dose

Leaf disk test

10 µg/cm2

Efficacy Feeding deterrence = 100%

Remarks Treatment to 3rd instar larvae for 4 days. (1)

(1) Jiwajinda, S., Hirai, N., Watanabe, K. Santisopasri, V., Chuengsamarnyart, N., Koshimizu, K., and Ohigashi, H. (2001) Phytochemistry, 56, 693. (2) Irie, H., Masaki, N., Ohno, K., Osaki, K., Taga, T., and Uyeo, S. (1970) Chem. Commun., 1066.

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Insect Antifeedants

16,17-DIDEHYDRO-16(E) – STEMOFOLINE

887

C22H27O5N (385.44)

M.p. : 172–174° [α]18 D : +230° (MeOH)

OCH3

N

O

O

O O

(1)

(1)

SOURCE: Stemona collinsae Craib (Stemonaceae)

(1)

ACTIVITY PROFILE Test Insect Plutella xylostella (L.) (Diamondback moth)

Test Method

Conc. / Dose

Leaf disk test

2.5 µg/cm2

Efficacy Feeding deterrence = 100%

Remarks Treatment to 3rd instar larvae for 4 days. (1)

(1) Jiwajinda, S., Hirai, N., Watanabe, K. Santisopasri, V., Chuengsamarnyart, N., Koshimizu, K., and Ohigashi, H. (2001) Phytochemistry, 56, 693.

© 2005 by CRC Press LLC

888

Opender Koul

STIGMAST-7-EN-3-OL

C29H50O (414.71)

M.p. : 145–146° (151–151.5°) [α]30 D : +9.1 (CHCl3)

H HO

(1, 2)

(1) SOURCE: Wedelia biflora (L.) DC, sami scandent shrub (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Anthonomus grandis Bohem. (Boll weevil)

Test Method

Conc. / Dose

Agar plug bioassay

1.0 mg/plug

Efficacy

Remarks

Feeding deterrence = 30.0%

Treatment to newly emerged boll weevils in the dark at 80°F for 4 h. Plug size: Diameter = 1.3 cm Length = 3.6 cm (1)

(1) Miles, D.H., Chittawong, V., Payne, A.M., Hedin, P.A., and Kokpol, U. (1990) J. Agric. Food Chem., 38, 1591. (2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC

Insect Antifeedants

STIZOLIN

889

C15H20O4 (264.32)

M.p. : 184.5–186.5° (dec.) [α]20 D : –30.46° (CHCl3)

OH

CH2 O O O

(1, 2)

(1, 2)

SOURCE: Stizolophus balsamita (Lam.) Cass. ex Takht (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Tribolium confusum Duv. (Confused flour beetle)

Test Method

Conc. / Dose

Wafer disk test

10 mg/ml

Efficacy Feeding deterrence coefficient = 162

Remarks Treatment to larvae. Data on 0–200 greater deterrence scale. (2)

(1) Mukhametzhanov, M.N., Shreter, A.I., and Pakalns, D. (1970) Khim. Prir. Soedin., 6, 505, (1971), 7, 405. (2) Nawrot, J., Harmatha, J., and Bloszyk, E. (1986) In E. Donahaye and S. Navarro (eds.), Proc. 4th Int. Conf. Stored Product Protection, Tel Aviv, Israel, pp. 591–597.

© 2005 by CRC Press LLC

890

Opender Koul

STRYCHNINE

C21H22O2N2 (334.42)

M.p. : 270–271° (275–285°) [α]18 D : –139° (CHCl3)

N H N

H O

O

(1, 2)

(1, 2,3) SOURCE: Commercial sample

(3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Phormia regina (Meigen) (Blowfly)

Sucrose solution feeding

10 mM

Feeding deterrence = 45.0% after 6 h and 49.0% after 24 h

1. Treatment to 2-, 4-, and 6-day-old adults, starved earlier for 24 h. (3)

2. Spodoptera litura (Fab.) (Tobacco armyworm)

Leaf disk no-choice assay

70 µg/1.5 cm2

Feeding deterrence = 60.7%

2. Treatment to 5th instar larvae, prestarved for 3 h. Treatment given for 30 m. (4)

LD50 (rats): 5.0 mg/kg (oral)

(5)

(1) Watson, E.R. and Sen, H.D. (1926) J. Ind. Chem. Soc., 3, 397. (2) Woodward, R.B., Cava, M.P., Ollis, W.D., Hunger, A., Daeniker, H.U., and Schenker, K. (1954) J. Am. Chem. Soc., 76, 4749. (3) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299. (4) Passreiter, C.M. and Isman, M.B. (1997) Biochem Syst. Ecol., 25, 371. (5) Amann, A., Jaeger, K.H., and Jarisch, A. (1943) Arch. Exp. Pathol. Pharmakol., 201, 161.

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Insect Antifeedants

SUCCINIC ACID

891

C4H6O4 (118.09)

M.p. : 184–185° B.p. : 235° (dec.)

O

OH OH

O

(1)

(1) SOURCE: Osmunda japonica (L.) Thunb., flowering fern (Osmundaceae)

(1)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina DeLorza (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose 0.8%

Efficacy Feeding deterrence = 7.2%

Remarks Treatment to 5th stadium larvae. (1)

Strong antifeedance 0.4%

Feeding deterrence = 18.8% Strong antifeedance

0.2%

Feeding deterrence = 34.1% Slight antifeedance

LD50 (rats): 8.53 g/kg (oral)

(2)

(1) Numata, A., Hokimoto, K., Takemura, T., Katsuno, T., and Yamamoto, K. (1984) Chem. Pharm. Bull., 32, 2815. (2) Smyth, H.F. Jr., Carpenter, C.P., and Weil, C.S. (1951) Arch. Ind. Hyg. Occup. Med., 4, 119.

© 2005 by CRC Press LLC

892

Opender Koul

18 – SUCCINYLOXYGRINDELIC ACID

C24H36O7 (436.54)

[α]D : –55° (CHCl3)

COOH

O

OCOCH2.CH2COOH

(1)

(1)

SOURCE: Chrysothamnus nauseosus (Pall.) Britt., rubber rabbitbush (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Schizaphis graminum (Rondani) (Wheat aphid)

Artificial diet feeding

Conc. / Dose 0.003%

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to aphids at random. Concentration = EC50 value. (2)

(1) Rose, A.F. (1980) Phytochemistry, 19, 2689. (2) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

© 2005 by CRC Press LLC

Insect Antifeedants

TAGITININ–A

893

C19H28O7 (368.43)

M.p. : 168–170° [α]D : –154° (EtOH)

OH O O O

HO

CH2

O O

(1, 2)

(1)

SOURCE: Tithonia diversifolia (Hemsl.) Gray, Mexican sunflower (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Philosamia ricini Hutt. (Eri silkworm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

1.0%

Feeding inhibition = 96.9%

Treatment to 0- to 12-h-old 4th instar larvae.

0.5%

Feeding inhibition = 88.5%

EC50 = 0.22%

0.25%

Feeding inhibition = 53.4%

Calculated from Reference 2.

0.05%

Feeding inhibition = 30.8%

0.02%

Feeding inhibition = 28.4%

(2)

(1) Pal, R., Kulshreshtha, D.K., and Rastogi, R.P. (1976) Ind. J. Chem., 14B, 259. (2) Dutta, P., Bhattacharyya, P.R., Rabha, L.C., Bordoloi, D.N., Barua, N.C., Chowdhury, P.K., Sharma, R.P., and Barua, J.N. (1986) Phytoparasitica, 14, 77.

© 2005 by CRC Press LLC

894

Opender Koul

TAGITININ–C

C19H24O6 (348.39)

Oil [α]D : –204° (EtOH)

O OH O

O

O

O

CH2

(1, 2)

(1)

SOURCE: Tithonia diversifolia (Hemsl.) Gray, Mexican sunflower (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Philosamia ricini Hutt. (Eri silkworm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

1.0%

Feeding inhibition = 97.2%

Treatment to 0- to 12–h-old 4th instar larvae.

0.5%

Feeding inhibition = 89.6%

EC50 = 0.041%

0.25%

Feeding inhibition = 81.0%

Calculated from Reference 2.

0.05%

Feeding inhibition = 58.5%

0.02%

Feeding inhibition = 33.8%

(2)

(1) Pal, R., Kulshreshtha, D.K., and Rastogi, R.P. (1977) Ind. J. Chem., 15B, 208. (2) Dutta, P., Bhattacharyya, P.R., Rabha, L.C., Bordoloi, D.N., Barua, N.C., Chowdhury, P.K., Sharma, R.P., and Barua, J.N. (1986) Phytoparasitica, 14, 77.

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Insect Antifeedants

TANGERETIN

895

C20H20O7 (372.35)

OCH3

OCH3 H3CO

M.p. : 152°

O

H3CO OCH3

O

(1)

(1)

SOURCE: Gnaphalium affine D. Don, cud weed (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

2.8 × 10–7 mol/cm2

Feeding inhibition = 50%

Treatment to 3rd instar larvae in the dark for 2 to 5 h. Concentration = EC50 value. (1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC

896

Opender Koul

TANGERETIN (5-DEMETHYL)

C19H18O7 (358.33)

OCH3

OCH3 H3CO

M.p. : 175°

O

H3CO OH

O

(1)

(1)

SOURCE: Gnaphalium affine D. Don, cud weed (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

1.8 × 10–7 mol/cm2

Feeding inhibition = 50%

Treatment to 3rd instar larvae in the dark for 2 to 5 h. Concentration = EC50 value. (1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC

Insect Antifeedants

TECLEANTHINE

897

C17H15O5N (313.31)

O

M.p. : 158°

OCH3 O

O

N OCH3

(1, 2)

(1, 2)

SOURCE: Teclea trichocarpa Engl., African evergreen techlea (Meliaceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera exempta (Walker) (Nutgrass armyworm)

Test Method Leaf disk choice test

Conc. / Dose 5000 ppm

Efficacy Feeding inhibition = 100% after 2 h

Remarks Treatment to 3rd instar larvae. (2)

(1) Pegel, K.H. and Wright, W.G. (1969) J. Chem. Soc., 2327. (2) Lwande, W., Gebreyesus, T., Chapaya, A., Macfoy, C., Hassanali, A., and Okech, M. (1983) Insect Sci. Applic., 4, 393.

© 2005 by CRC Press LLC

898

Opender Koul

TENULIN

C17H22O5 (306.36)

M.p. : 196–198° [α]20 D : –21.7° (EtOH)

H

O O O

O OH

(1, 2)

(1, 2)

SOURCE: Helenium amarum (Raf.) H. Koch, bitterweed (Asteraceae)

(1, 2)

ACTIVITY PROFILE Test Insect Ostrinia nubilalis (Hubner) (European corn borer)

Test Method Leaf disk test

Conc. / Dose 3 µmol/g

Efficacy

Remarks

Feeding inhibition = 72.0%

Treatment to larvae. Data calculated from Reference 2. (2)

(1) Herz, W. and Sharma, R.P. (1975) J. Org. Chem., 40, 2557. (2) Arnason, J.T., Isman, M.B., Philogene, B.J.R., and Waddel, T.G. (1987) J. Nat. Prod., 50, 690.

© 2005 by CRC Press LLC

Insect Antifeedants

TENULIN OXIDE

899

C17H22O6 (322.34)

H

Only spectral data given

H

O O

H

O O

O OH

(1)

(1)

SOURCE: Helenium amarum (Raf.) H. Koch, bitterweed (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect Ostrinia nubilalis (Hubner) (European corn borer)

Test Method Leaf disk test

Conc. / Dose 3 µmol/g

Efficacy

Remarks

Feeding inhibition = 77.9%

Treatment to larvae. Data calculated from Reference 2. (2)

(1) Herz, W. and Sharma, R.P. (1975) J. Org. Chem., 40, 2557. (2) Arnason, J.T., Isman, M.B., Philogene, B.J.R., and Waddel, T.G. (1987) J. Nat. Prod., 50, 690.

© 2005 by CRC Press LLC

900

Opender Koul

TEPHROSIN

C23H22O7 (410.42)

M.p. : (–) form amorphous (±) form 198°

OCH3

[α]23 D : –118° (benzene) OCH3

O OH

O O

O H

(1)

(1)

SOURCE: Tephrosia elata Deflers., African tephrosia, also isolated from other species of Tephrosia (Fabaceae)

(1, 2)

ACTIVITY PROFILE Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Leaf disk test

1 µg/2 cm diameter disk

Feeding inhibition = 89.0%

1. Treatment to mid 6th instar larvae for 2 h. Larvae prestarved for 2 h. (2)

2. Eldana saccharina Walker (Sugar cane borer)

Leaf disk test

Per 1.8 cm diameter disk: 100 µg

Feeding inhibition = 94.0%

2. Treatment to 5th instar larvae for 24 h in dark. Larvae prestarved for 12 h. (2)

Test Insect

10 µg

Feeding inhibition = 86.0%

1 µg

Feeding inhibition = 72.0%

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 211. (2) Bentley, M.D., Hassanali, A., Lwandi, W., Njoroge, P.E.W., Sitayo, E.N.O., and Yatagai, M. (1987) Insect Sci. Applic., 8, 85.

© 2005 by CRC Press LLC

Insect Antifeedants

γ-TERPINENE

901

C10H16 (136.23)

B.p. : 58–62.5°/10 mm [α]25 D : +36° (neat) n25 D

: 1.4696

(1, 2)

(1)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect Pieris rapae crucivora Boisd. (Cabbage butterfly)

Test Method

Conc. / Dose

Leaf disk test

10–1 mol/L

Efficacy Feeding inhibition = 61.0% after 2 h.

Remarks Treatment to 5th instar larvae. (2)

LD50 (rats): 1680 mg/kg (oral) (1) Briggs, L.H. and Sutherland, M.D. (1948) J. Org. Chem., 13, 1. (2) Yano, K. (1987) J. Agric. Food Chem., 35, 889. (3) Opdyke, D.L.J. (1976) Food Cosmet. Toxicol., 14, 873.

© 2005 by CRC Press LLC

(3)

902

Opender Koul

2′,3′,22,23-TETRAHYDROAZADIRACHTIN

C35H48O16 (724.76)

Only spectral data given

O COOCH3 OH

O

O

OH

O

O

O OH

AcO H H3COOC

H

O

(1, 2)

(1, 2)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Efficacy

Glass fiber disk test: Choice No-choice

1 ppm 1 ppm

Feeding inhibition = 79.0% 41.7%

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Glass fiber disk test: Choice No-choice

1 ppm 1 ppm

Feeding inhibition = 97.0% 44.0%

3. Heliothis virescens (Fab.) (Tobacco budworm)

Glass fiber disk test: Choice No-choice

4. Helicoverpa armigera (Hubner) (Gram pod borer)

Glass fiber disk choice test

1 ppm 1 ppm 1 ppm

Feeding inhibition = 98.0% 36.0%

Remarks Treatment to 24- to 36-h-old starved final stadium larvae. Bioassay terminated after the larvae had consumed about 50% of one of the disks. (1) Deterrence calculated from Reference 1 for nochoice assay run for 8 to 9 h.

Feeding inhibition = 64.0%

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149. (2) Ley, S.V., Anderson, J.C., Blaney, W.M., Lidert, Z., Morgan, E.D., Robinson, N.G., Santafianos, D., Simmonds, M.S.J., and Toogood, P.L. (1989) Tetrahedron Lett., 30, 5175.

© 2005 by CRC Press LLC

Insect Antifeedants

TETRAHYDRO-ACETYLISOMONTANOLIDE

903

C24H36O8 (452.51)

Only spectral data given

OCOCH3 H

OCO

H O

OCOCH3

O

(1, 2)

(1)

SOURCE: Synthetic

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

1.0%

Feeding deterrence coefficient = 30

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

1.0%

Feeding deterrence coefficient: Adults = 104.0 Larvae = 83.0

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

1.0%

Feeding deterrence coefficient = 80.0

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Holub, M., Motl, O., Samek, Z., and Herout, V. (1972) Collect. Czech. Chem. Commun., 37, 1186. (2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

© 2005 by CRC Press LLC

904

Opender Koul

TETRAHYDROISOPONGAFLAVONE

O

C21H22O4 (338.40)

M.p. : 167–168°

O

OCH3

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Leaf disk test

100 µg/2 cm diameter disk

Feeding inhibition = 25.0%

1. Treatment to mid 6th instar larvae for 2 h. Larvae prestarved for 2 h. (1)

2. Eldana saccharina Walker (Sugar cane borer)

Leaf disk test

Per 1.8 cm diameter disk: 100 µg

Feeding inhibition = 94.0%

2. Treatment to 5th instar larvae for 24 h in dark. Larvae prestarved for 12 h. (1)

10 µg

Feeding inhibition = 87.0%

Per 2 cm diameter disk: 100 µg

Feeding inhibition = 64.0%

3. Maruca testulalis (Geyer) (Bean pod borer)

Leaf disk test

Feeding inhibition = 86.0%

3. Treatment to late 5th instar larvae for 6 h. (1)

10 µg

(1) Bentley, M.D., Hassanali, A., Lwandi, W., Njoroge, P.E.W., Sitayo, E.N.O., and Yatagai, M. (1987) Insect Sci. Applic., 8, 85.

© 2005 by CRC Press LLC

Insect Antifeedants

TEUCJAPONIN–A

905

C22H28O7 (404.46) O

M.p. : 145–148° [α]20 D : +38.8° (CHCl3)

O

H

O

O OAc

OH

(1, 2)

(1)

SOURCE: Teucrium japonicum Houtt., Japanese germander (Labiatae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Prodenia litura (Fab.) (Tobacco armyworm)

Leaf disk choice test

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Glass fiber disk choice test

Test Insect

Efficacy

Remarks

400 ppm

Feeding inhibition = Threshold level, after 5h

1. Treatment to early 3rd instar larvae. (1)

100 ppm

Feeding inhibition = 12.9%

2. Treatment to final stadium larvae starved for 4 h. Treatment never longer than 18 h so that never more than 50% of any disk was consumed. (2)

(1) Miyase, T., Kawasaki, H., Noro, T., Ueno, A., Fukushima, S., and Takemoto, T. (1981) Chem. Pharm. Bull., 29, 3561. (2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry, 28, 1069.

© 2005 by CRC Press LLC

906

Opender Koul

TEUCJAPONIN–B

C22H28O7 (404.46) O

M.p. : 211–213° (255–258°) [α]20 D : +60° (CH2Cl2)

O

H

O

O OAc

OH

(1)

(1, 2) SOURCE: Teucrium japonicum Houtt., Japanese germander (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Helicoverpa armigera (Hubner) (Gram pod borer)

Test Method Glass fiber disk choice test

Glass fiber disk choice test

Conc. / Dose

Efficacy

Remarks

100 ppm

Feeding inhibition = 48.9%

10 ppm

Feeding inhibition = 43.0%

1. Treatment to final stadium larvae starved for 4 h. Treatment never longer than 18 h so that never more than 50% of any disk was consumed. (2)

100 ppm

Feeding inhibition = 29.8%

10 ppm

Feeding inhibition = 23.2%

2. Treatment to final stadium larvae as in S. littoralis above. (2)

(1) Miyase, T., Kawasaki, H., Noro, T., Ueno, A., Fukushima, S., and Takemoto, T. (1981) Chem. Pharm. Bull., 29, 3561. (2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry, 28, 1069.

© 2005 by CRC Press LLC

Insect Antifeedants

TEUCRIN–A

907

C19H20O6 (344.36) O

M.p. : 195–198° (acetate) [α]20 D : +96.2° (CHCl3) (acetate)

O

H

O

OH O O

(1)

(1, 2) SOURCE: Teucrium chamaedrys L., germander wall (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to newly emerged 4th instar larvae for 4 h in nochoice situation and up to 24 h or until 50% of the disks were consumed in choice situation. (2)

Leaf disk choice test

1000 ppm

Feeding inhibition = 34.0%

Leaf disk no-choice test

1000 ppm

Feeding inhibition = 75.0%

300 ppm

Feeding inhibition = 51.0%

100 ppm

Feeding inhibition = 35.6%

(1) Fernandez-Gadea, F., Pascual, C., Rodriguez, B., and Savona, G. (1983) Phytochemistry, 22, 723. (2) Ortego, F., Rodriguez, B., and Castanera, P. (1995) J. Chem. Ecol., 21, 1375.

© 2005 by CRC Press LLC

908

Opender Koul

TEUCVIN

C19H20O5 (328.36)

M.p. : 207–208°

O

[α]D : +88.4° (CHCl3)

O

H

O

O O

(1)

(1, 2) SOURCE: Teucrium viscidum Blm., germander sticky (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Leaf disk nochoice test

Conc. / Dose

Efficacy

Remarks

1000 ppm

Feeding inhibition = 25.1%

300 ppm

Feeding inhibition = 8.1%

1000 ppm

Feeding inhibition = 77.8%

Treatment to newly emerged 4th instar larvae for 4 h in nochoice situation and up to 24 h or until 50% of the disks were consumed in choice situation. (2)

300 ppm

Feeding inhibition = 59.4%

100 ppm

Feeding inhibition = 45.6%

EC50 = 94 ppm in nochoice test. (3)

(1) Fujita, E., Uchida, T., and Fujita, T. (1974) J. Chem. Soc. Perkin I, 1547. (2) Ortego, F., Rodriguez, B., and Castanera, P. (1995) J. Chem. Ecol., 21, 1375. (3) Lopez-Olguin, J., Maria, C.T., Ortego, F., Castanera, P., and Rodriguez, B. (1999) Phytochemistry, 50, 749–753.

© 2005 by CRC Press LLC

Insect Antifeedants

TEUFLIDIN

909

C19H20O6 (344.36)

M.p. : 178°

O

[α]20 D : –100° (CHCl3)

O

H

O

HO O O

(1, 2)

(1)

SOURCE: Teucrium viscidum Blm., sticky germander (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to newly emerged 4th instar larvae for 4 h in nochoice situation and up to 24 h or until 50% of the disks were consumed in choice situation.

Leaf disk choice test

1000 ppm

Feeding inhibition = 57.5%

Leaf disk no-choice test

1000 ppm

Feeding inhibition = 92.9%

EC50 = 53 ppm in nochoice test. (3)

(1) Fernandez-Gadea, F., Pascual, C., Rodriguez, B., and Savona, G. (1983) Phytochemistry, 22, 723. (2) Rodriguez, M.C., Barluenga, J., Savona, G., Piozzi, F., Servettaz, O., and Rodriguez, B. (1984) Phytochemistry, 23, 1465. (3) Lopez-Olguin, J., Maria, C.T., Ortego, F., Castanera, P., and Rodriguez, B. (1999) Phytochemistry, 50, 749–753.

© 2005 by CRC Press LLC

910

Opender Koul

TEUFLIN

C19H20O5 (328.36)

M.p. : 153°

O

[α]D : +12° (CHCl3)

O

H

O

O O

(1, 2)

(1, 2) SOURCE: Teucrium chamaedrys L., wall germander (Labiatae)

(1)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to newly emerged 4th instar larvae for 4 h in nochoice situation and up to 24 h or until 50% of the disks were consumed in choice situation.

Leaf disk choice test

1000 ppm

Feeding inhibition = 44.1%

Leaf disk nochoice test

1000 ppm

Feeding inhibition = 89.3%

EC50 = 91 ppm in nochoice test. (3)

(1) Fernandez-Gadea, F., Pascual, C., Rodriguez, B., and Savona, G. (1983) Phytochemistry, 22, 723. (2) Rodriguez, M.C., Barluenga, J., Savona, G., Piozzi, F., Servettaz, O., and Rodriguez, B. (1984) Phytochemistry, 23, 1465. (3) Lopez-Olguin, J., Maria, C.T., Ortego, F., Castanera, P., and Rodriguez, B. (1999) Phytochemistry, 50, 749–753.

© 2005 by CRC Press LLC

Insect Antifeedants

TEUMASSILENIN–A

911

C20H30O5 (350.46)

M.p. : 187–190°

O

[α]20 D : +2° (CHCl3/MeOH) H OH

H

H CHO

O OH

(1)

(1, 2) SOURCE: Teucrium massiliense, L., purple germander (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to newly emerged 4th instar larvae pre-starved for 6 h until 50% of the control disks were consumed in choice situation and 75% in no-choice assay.

Leaf disk choice test

1000 ppm

Feeding inhibition = 88.2%

Leaf disk nochoice test

1000 ppm

Feeding inhibition = 75.6%

Assayed against Spodoptera exigua as well, but found inactive against this species. (2)

(1) Fontana, G., Paternostro, M.P., Savona, G., Rodriguez, B., and de la Torre, M.C. (1998) J. Nat. Prod., 61, 1242. (2) Caballero, C., Castanera, P., Ortego, F., Fontana, G., Pierro, P., Savona, G., and Rodriguez, B. (2001) Phytochemistry, 58, 249.

© 2005 by CRC Press LLC

912

Opender Koul

TEUMASSILENIN–C

C20H30O5 (350.46) O

M.p. : 125–127° [α]20 D : –33.4° (CHCl3)

H OH

HO

O

OH

(1)

(1, 2) SOURCE: Teucrium massiliense, L., purple germander (Labiatae)

(1, 2)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method

Conc. / Dose

Efficacy

Remarks Treatment to newly emerged 4th instar larvae, pre-starved for 6 h until 50% of the control disks were consumed in choice situation and 75% in no-choice assay.

Leaf disk choice test

1000 ppm

Feeding inhibition = 73.7%

Leaf disk nochoice test

1000 ppm

Feeding inhibition = 67.6%

Assayed against Spodoptera exigua as well, but found inactive against this species. (2)

(1) Fontana, G., Paternostro, M.P., Savona, G., Rodriguez, B., and de la Torre, M.C. (1998) J. Nat. Prod., 61, 1242. (2) Caballero, C., Castanera, P., Ortego, F., Fontana, G., Pierro, P., Savona, G., and Rodriguez, B. (2001) Phytochemistry, 58, 249.

© 2005 by CRC Press LLC

Insect Antifeedants

TEUSCOROLIDE

913

C19H18O5 (326.35)

M.p. : 198–200°

O

[α]20 D : +13.5° (CHCl3) O

H

O

O O

(1, 2)

(1)

SOURCE: Teucrium scorodonia L., garlic sage (Labiatae)

(1, 3)

ACTIVITY PROFILE Test Insect Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Leaf disk choice test

Leaf disk nochoice test

Conc. / Dose

Efficacy

Remarks

1000 ppm

Feeding inhibition = 32.9%

300 ppm

Feeding inhibition = 25.2%

1000 ppm

Feeding inhibition = 39.0%

Treatment to newly emerged 4th instar larvae for 4 h in nochoice situation and up to 24 h or until 50% of the disks were consumed in choice situation. (2)

300 ppm

Feeding inhibition = 7.3%

EC50 = 394 ppm in no-choice test. (3)

(1) Marco, J.L., Rodriguez, B., Savona, G., and Piozzi, F. (1982) Phytochemistry, 21, 2567; (1983), 22, 727. (2) Ortego, F., Rodriguez, B., and Castanera, P. (1995) J. Chem. Ecol., 21, 1375. (3) Lopez-Olguin, J., Maria, C.T., Ortego, F., Castanera, P., and Rodriguez, B. (1999) Phytochemistry, 50, 749.

© 2005 by CRC Press LLC

914

Opender Koul

(+)-3-THUJONE

C10H16O (152.23)

B.p. : 40.9°/0.5 mm [α]25 D : +78.8° (neat)

O

(1)

(1) SOURCE: Thuja plicata Donn. ex Don, Western red cedar (Cupressaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Pissodes strobi Peck. (White pine weevil)

Agar disk procedure

5 µg/disk

Efficacy

Remarks

Feeding inhibition = 34.8% within 24 h.

Treatment to adult weevils. (2)

LD50 (mice): 87.5 mg/kg (sc.) (1) Hach, V., Lockhart, R.W., McDonald, E.C., and Cartlidge, D.M. (1971) Can. J. Chem., 49, 1762. (2) Alfaro, R.I., Pierce, H.D. Jr., Borden, J.H., Oehlschlager, A.C. (1981) J. Chem. Ecol., 7, 39. (3) Rice, K.C. and Wilson, R.S. (1976) J. Med. Chem., 19, 1054.

© 2005 by CRC Press LLC

(3)

Insect Antifeedants

3 – TIGLOYLAZADIRACHTOL (also see Azadirachtin–B)

915

C33H42O14 (662.68)

[α]20 D : –69.4° (CH2Cl2)

COOCH3 HO

H

O

M.p. : 204–206°

OH O

O O

O OH

O H

H3COOC

H

O

(1, 2)

(1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

2. Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

3. Heliothis virescens (Fab.) (Tobacco budworm) 4. Helicoverpa armigera (Hubner) (Gram pod borer)

Test Method Glass fiber disk choice test Glass fiber disk nochoice test Glass fiber disk choice test Glass fiber disk nochoice test Glass fiber disk choice test Glass fiber disk choice test

Conc. / Dose

Efficacy

Remarks

1 ppm

Feeding inhibition = 97.0%.

1 ppm

Feeding inhibition = 80.6%.

1 ppm

Feeding inhibition = 60.0%.

Treatment to 24- to 36-h-old starved final stadium larvae. Bioassay terminated after the larvae had consumed about 50% of one of the disks. (2)

1 ppm

Feeding inhibition = 66.2%.

1 ppm

Feeding inhibition = 43.0%.

1 ppm

Feeding inhibition = 41.0%.

Deterrence calculated from Reference 2 for nochoice assay run for 8 to 9 h.

(1) Klenk, A., Bokel, M., and Kraus, W. (1986) J. Chem. Soc. Chem. Commun., 523. (2) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl., 55, 149.

© 2005 by CRC Press LLC

916

Opender Koul

6 – TIGLOYL CHAPARRINONE

C25H32O9 (476.52)

M.p. : 229°

OH

[α]22 D : +195.7° (neat) HO HO

O

O

O

O

H OCO

(1)

(1, 2) SOURCE: Simaba cuspidata Spruce ex Engl., wasakusili (Scrophulariaceae) Ailanthus grandis Prain., ailanthus (Simaroubaceae)

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method

Conc. / Dose

Leaf disk choice test

12.0 µg/cm2

Feeding inhibition = 60–90% after 6 days.

6.0 µg/cm2

Feeding inhibition = 30–60% after 6 days.

3.0 µg/cm2

Feeding inhibition = 30–60% after 2 days and 0–30% after 6 days of treatment.

Efficacy

Remarks Treatment to 3rd instar larvae. (2)

(1) Polonsky, J., Varon, Z., Moretti, C., Pettit, G.R., Herald, C.L., Rideout, J., Saha, S.B., and Khastgir, H.N. (1980) J. Nat. Prod., 43, 503. (2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

Insect Antifeedants

13 – TIGLOYLOXYLUPANINE

917

C20H30O3N2 (346.47)

Oil B.p. : 180–200°/0.001 mm

H

N

N

O H

O

O

(1, 2)

(1)

SOURCE: Synthetic Also isolated from Lupinus polyphyllus Lindl., lupine (Fabaceae)

(2) (1)

ACTIVITY PROFILE Test Insect Choristoneura fumiferana (Clemens) (Spruce budworm)

Test Method Paper penicillin disk assay

Conc. / Dose 1.4 × 103 M

Efficacy Feeding deterrence = 89.0%

Remarks Treatment to 6th instar larvae. (2)

(1) Dictionary of Natural Products (1994) Chapman & Hall, London. (2) Bentley, M.D., Leonard, D.E., Reynolds, E.K., Leach, S., Beck, A.B., and Murakoshi, I. (1984) Ann. Entomol. Soc. Am., 77, 398.

© 2005 by CRC Press LLC

918

Opender Koul

5α-TIGLOYLOXYSILPHINEN-3-ONE

C20H28O3 (316.20)

Oil [α]D : –67.2° (CHCl3)

O

O

O

(1)

(1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae)

(1)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Choice feeding assay

>200 nmol/cm2

Feeding deterrence = 50.0%

1. Treatment to 6th instar larvae.

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Choice feeding assay

43.9 nmol/cm2

Feeding deterrence = 50.0%

2. Treatment to adults.

3. Myzus persicae (Sulzer) (Green peach aphid)

Choice feeding assay

29.1 nmol/cm2

Feeding deterrence = 50.0%

3. Treatment to apterous adult aphids.

4. Rhopalosiphum padi (L.) (Cereal aphid)

Choice feeding assay

39.8 nmol/cm2

Feeding deterrence = 50.0%

4. Treatment to apterous adult aphids.

5. Sitobion avenae (Fab.) (Grass aphid)

Choice feeding assay

>100 nmol/cm2

Feeding deterrence = 50.0%

5. Treatment to apterous adult aphids.

6. Diuraphis noxia (Mordvilko) (Wheat aphid)

Choice feeding assay

29.8 nmol/cm2

Feeding deterrence = 50.0%

6. Treatment to apterous adult aphids.

Test Insect

Efficacy

Remarks

Concentrations = EC50 values. (1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.

© 2005 by CRC Press LLC

Insect Antifeedants

TILIROSIDE

919

C30H26O13 (594.53) OH

HO

M.p. : 269–271° (267–269°)

O

[α]24 D : +69.9° (MeOH)

O OH

O

HO

OH

O O

HO OH

O

(1)

(1, 2) SOURCE: Pteridium aquilinum L. Kuhn, bracken fern (Pteridophyte)

(2)

ACTIVITY PROFILE Test Insect Pieris brassicae (L.) (Large white butterfly)

Test Method Leaf disk no-choice test

Conc. / Dose 1.7 × 10 –2 M

Efficacy Feeding deterrence ratio = 3.04 Very effective deterrence

(1) Vermes, B., Chari, V.M., and Wagner, H. (1981) Helv. Chim. Acta, 64, 1964. (2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.

© 2005 by CRC Press LLC

Remarks Treatment to 2nd day 5th instar unstarved larvae. (2)

920

Opender Koul

TOMATIDINE

C27H45O2N (415.66)

M.p. : 202–206° (210–211°) [α]25 D : +8° (CHCl3)

N H O

HO H

(1, 2)

(1)

SOURCE: Commercial material, commonly occurs in Solanum spp. (Solanaceae)

(2)

ACTIVITY PROFILE Test Insect Choristoneura fumiferana (Clemens) (Spruce budworm)

Test Method Paper penicillin disk assay

Conc. / Dose

Efficacy

10–3 M

Feeding deterrence = 64.0%

10–4 M

Feeding deterrence = 19.0%

Remarks Treatment to 6th instar larvae. (2)

(1) Brink, N.G. and Folkers, K. (1951) J. Am. Chem. Soc., 73, 4018. (2) Bentley, M.D., Leonard, D.E., and Bushway, R.J. (1984) Ann. Entomol. Soc. Am., 77, 401.

© 2005 by CRC Press LLC

Insect Antifeedants

TOMATINE

921

C50H83O21N (1034.20)

M.p. : 263–268° (dec.) [α]20 D : –18° (pyridine)

N H O

β-lycotetraose-O H

(1, 2)

(1)

SOURCE: Commercial material

(2, 3, 4)

ACTIVITY PROFILE Test Insect 1. Choristoneura fumiferana (Clemens) (Spruce budworm)

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Test Method Paper penicillin disk assay

Sensillum response recording

Conc. / Dose

Efficacy

Remarks

10–3 M

Feeding deterrence = 91.0%

1. Treatment to 6th instar larvae. (2)

10–4 M

Feeding deterrence = 48.0%

0.2% wet weight

Feeding deterrence = 50.0%

2. Treatment to adult beetles. Concentration = EC50 value. (3)

3. Phormia regina (Meigen) (Blowfly)

Sucrose solution feeding

10 mM

Feeding deterrence = 88.0% after 6 hours and 86.0% after 24 hours

3. Treatment to 2-, 4-, and 6-day-old adults after 24-hour pre-starvation. (4)

LD (rats): 900–1000 mg/kg (oral) (1) Kuhn, R., Low, I., and Gauke, A. (1950) Chem Ber., 83, 448. (2) Bentley, M.D., Leonard, D.E., and Bushway, R.J. (1984) Ann. Entomol. Soc. Am., 77, 401. (3) Mitchell, B.K. and Harrison, G.D. (1985) J. Chem. Ecol., 11, 73. (4) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299. (5) Wilson, R.H., Poley, G.W., and DeEds, F. (1961) Toxicol. Appl. Pharmacol., 3, 39.

© 2005 by CRC Press LLC

(5)

922

Opender Koul

TOONACILIN

C31H38O9 (554.64) O

M.p. : 118–119° [α]20 D : +69° (CHCl3)

OAc AcO

O

H

O

CH2

COOCH3

(1)

(1)

SOURCE: Toona ciliata M.J. Roem, red cedar (Meliaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Bean leaf assay

Conc. / Dose 0.2%

Efficacy

Remarks

Feeding deterrence = 100%

Treatment to adult beetles. (2)

(1) Kraus, W., Grimminger, W., and Sawitzki, G. (1978) Angew. Chemie, 17, 452. (2) Kraus, W. and Grimminger, W. (1980) Nouv. J. De Chim., 4, 651.

© 2005 by CRC Press LLC

Insect Antifeedants

TOOSENDANIN

923

C30H38O11 (574.62)

OH

[α]16 D : +4.3° (CHCl3)

O

OAc

M.p. : 251–252°

O

O

O AcO

OH

HO H

(1,2,3)

(1, 2)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae)

(3)

ACTIVITY PROFILE Test Insect

Test Method

1. Ostrinia furnacalis (Guenee) (Asiatic corn borer)

Artificial diet feeding

2. Helicoverpa armigera (Hubner) (Gram pod borer)

Artificial diet feeding

Conc. / Dose 20 ppm

56.6 ppm

Efficacy

Remarks

Feeding deterrence = Significant, determined by insect growth

1. Treatment to larvae.

Feeding deterrence = 50%

2. Treatment to 3rd instar larvae.

No quantitative data recorded. (3)

Concentration = FI50 value. (4)

(1) (2) (3) (4)

Shu, G.X. and Liang, X.T. (1980) Acta Chim. Cin., 38, 196. Ochi, M., Kotsuki, H., Hirotsu, K., and Tokoroyama, T. (1976) Tetrahedron Lett., 2877. Shin-Foon, C. (1984) Proc. 2nd Int. Neem Conf., Rauischholzhausen, Germany, p. 255. Koul, O., Multani, J.S., Singh, G., and Wahab, S. (2002) Curr. Sci., 83, 1387.

© 2005 by CRC Press LLC

924

Opender Koul

TR–A

C39H54O16 (778.84)

Amorphous

OH

O O

H HCOO O AcO H

O

OH

H CH2

O

OAc

H COOC2H5 HO

(1)

(1)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Agrotis segetum (Denis & Schiff.) (Turnip cutworm)

Test Method

Conc. / Dose

Leaf disk choice test

200 ppm

Efficacy

Remarks

Feeding deterrence = Strong antifeedant activity

Treatment to larvae. No quantitative data recorded. (1)

(1) Nakatani, M., Okamoto, M., Iwashita, T., Mizukawa, K., Naoki, H., and Hase, T. (1984) Heterocycles, 22, 2335.

© 2005 by CRC Press LLC

Insect Antifeedants

TR–B

925

C35H44O14 (688.72)

Amorphous

OH

[α]25 D : –18.3° (CHCl3)

O O

H HCOO O AcO H

O

OH

H CH2

O

O

O

O

(1)

(1, 2)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Agrotis segetum (Denis & Schiff.) (Turnip cutworm)

Test Method

Conc. / Dose

Leaf disk choice test

200 ppm

Efficacy

Remarks

Feeding deterrence = Strong antifeedant activity

Treatment to larvae. No quantitative data recorded. (1)

(1) Nakatani, M., Okamoto, M., Iwashita, T., Mizukawa, K., Naoki, H., and Hase, T. (1984) Heterocycles, 22, 2335. (2) Gunatikala, A.A.L., Bolzani, V.S., Dagne, E., Hofmann, G.A., Johnson, R.K., McCabe, F.L., Mattern, M.R., and Kingston, D.G. (1998) J. Nat. Prod., 61, 179.

© 2005 by CRC Press LLC

926

Opender Koul

TR–C

C38H52O16 (764.82)

Amorphous

OH

O O

H HCOO O AcO H

O

OH

O

CH2

OAc

COOCH3 HO

(1)

(1)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Agrotis segetum (Denis & Schiff.) (Turnip cutworm)

Test Method

Conc. / Dose

Leaf disk choice test

200 ppm

Efficacy

Remarks

Feeding deterrence = Strong antifeedant activity

Treatment to larvae. No quantitative data recorded. (1)

(1) Nakatani, M., Okamoto, M., Iwashita, T., Mizukawa, K., Naoki, H., and Hase, T. (1984) Heterocycles, 22, 2335.

© 2005 by CRC Press LLC

Insect Antifeedants

TREWIASINE

927

C37H52O11N3Cl (750.28)

O O

[α]23 D : –94° (CHCl3)

N O

Cl H3CO

M.p. : 182–185°

O O

N

O

N

H3CO

O

OH OCH3

(1, 2)

(1)

SOURCE: Trewia nudiflora Wight, false white teak (Euphorbiaceae)

(2)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk test

Conc. / Dose

Efficacy

Remarks

0.5%

Feeding deterrence = 84.6%

0.25%

Feeding deterrence = 91.9%

Treatment to female beetles of same age (1–2 weeks posteclosion).

0.015%

Feeding deterrence = 49.6%

(1) Powell, R.G., Weisleder, D., and Smith, C.R. Jr. (1981) J. Org. Chem., 46, 4398. (2) Reed, D.K., Kwolek, W.F., and Smith, C.R. Jr. (1983) J. Econ. Entomol., 76, 641.

© 2005 by CRC Press LLC

Data calculated from Reference 2. (2)

928

Opender Koul

TRICHILIN–A

C35H46O13 (674.74)

OH

[α]25 D : –36.7° (CHCl3)

O

OH

M.p. : 191–192° (dec.)

O

AcO O

H

AcO

O OH

O

H O

(1)

(1)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Cramer) (Southern armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

300 ppm

Efficacy

Remarks

Feeding deterrence = 100%

Treatment to larvae. Feeding of this compound over a 10day period to the 3rd instar larvae killed the insects. (1)

(1) Nakatani, M., James, J.C., and Nakanishi, K. (1981) J. Am. Chem. Soc., 103, 1228.

© 2005 by CRC Press LLC

Insect Antifeedants

TRICHILIN–B

929

C35H46O13 (674.74) O

OH

OH

[α]22 D : –10° (neat)

O

AcO O

H

AcO

O OH

O

H O

(1)

(1)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae) Melia azedarach L., chinaberry (Meliaceae)

(1) (2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice test

Test Insect

Efficacy

Remarks

200 ppm

Feeding deterrence = 100%

1. Treatment to 3rd instar larvae. (1)

200 ppm

Feeding deterrence = 100%

2. Treatment to 3rd instar larvae. (2)

(1) Nakatani, M., James, J.C., and Nakanishi, K. (1981) J. Am. Chem. Soc., 103, 1228. (2) Nakatani, M., Huang, R.C., Okamura, H., Naoki, H., and Iwagawa, T. (1994) Phytochemistry, 36, 39.

© 2005 by CRC Press LLC

930

Opender Koul

TRICHILIN–D

C35H46O12 (658.74)

[α]22 D : –72.6° (neat)

O

OH

Oil

O

AcO O

H

AcO

O OH

O

H O

(1)

(1)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae) Melia azedarach L., chinaberry (Meliaceae)

(1) (2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice test

Test Insect

Efficacy

Remarks

400 ppm

Feeding deterrence = 100%

1. Treatment to 3rd instar larvae. (1)

400 ppm

Feeding deterrence = 100%

2. Treatment to 3rd instar larvae. (2)

(1) Nakatani, M., James, J.C., and Nakanishi, K. (1981) J. Am. Chem. Soc., 103, 1228. (2) Nakatani, M., Huang, R.C., Okamura, H., Naoki, H., and Iwagawa, T. (1994) Phytochemistry, 36, 39.

© 2005 by CRC Press LLC

Insect Antifeedants

TRICHILIN–H

931

C36H46O14 (702.75) O

OAc

OH

[α]22 D : –20.2° (MeOH)

O

AcO O

H

AcO

O OH

O

H O

(1)

(1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae) Melia azedarach L., chinaberry (Meliaceae)

(1) (2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Spodoptera eridania (Cramer) (Southern armyworm)

Leaf disk choice test

2. Spodoptera exigua (Hubner) (Beet armyworm)

Leaf disk choice test

Test Insect

Efficacy

Remarks

400 ppm or 8 µg/cm2

Feeding deterrence = 50.0%

1. Treatment to 3rd instar larvae for 6–24 hours during which period 50% of one of the disks was consumed. (1, 2)

400 ppm or 8 µg/cm2

Feeding deterrence = 50.0%

2. Treatment to 3rd instar larvae for 6–24 hours during which period 50% of one of the disks was consumed. (1, 2)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117. (2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51, 11736.

© 2005 by CRC Press LLC

932

Opender Koul

TRICHILIN–I

C35H46O13 (674.74)

Amorphous powder

O OAc

OH

O

HO O

H

AcO

O OH

O

H O

(1)

(1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Cramer) (Southern armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

400 ppm or 8 µg/cm2

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 3rd instar larvae for 6–24 hours during which period 50% of one of the disks was consumed. (1)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117.

© 2005 by CRC Press LLC

Insect Antifeedants

TRICHILIN–J

933

C33H44O11 (616.70) Amorphous powder O

OH

[α]23 D : +20° (MeOH)

O

HO

O

H

AcO

O OH

O

H O

(1)

(1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Cramer) (Southern armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

400 ppm or 8 µg/cm2

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 3rd instar larvae for 6–24 hours during which period 50% of one of the disks was consumed. (1)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117.

© 2005 by CRC Press LLC

934

Opender Koul

TRICHILIN–K

C32H42O11 (602.68)

[α]22 D : –20° (MeOH)

O

OH

Amorphous powder

O

HO

O

H

AcO

O OH

O

H O

(1)

(1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Cramer) (Southern armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

400 ppm or 8 µg/cm2

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 3rd instar larvae for 6–24 hours during which period 50% of one of the disks was consumed. (1)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117.

© 2005 by CRC Press LLC

Insect Antifeedants

TRICHILIN–L

935

C33H44O11 (616.70) O

OH

Amorphous powder [α]22 D : –14° (MeOH)

O

AcO

O

H

O OH

HO O

H O

(1)

(1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Cramer) (Southern armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

400 ppm or 8 µg/cm2

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 3rd instar larvae for 6–24 hours during which period 50% of one of the disks was consumed. (1)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117.

© 2005 by CRC Press LLC

936

Opender Koul

TRICHILININ–B

C35H46O9 (610.74)

M.p. : 168–170° [α]19 D : +56° (MeOH)

O

O

OAc

O

H

AcO

OH O

(1)

(1) SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae) also isolated from M. volkensi Guerke

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Cramer) (Southern armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 3rd instar larvae for 6–24 hours during which period 50% of one of the disks was consumed. (1)

(1) Zhou, J., Okamura, H., Iwagawa, T., Nakamura, Y., Nakayama, N, Tadera, K., and Nakatani, M. (1995) Heterocycles, 41, 2795.

© 2005 by CRC Press LLC

Insect Antifeedants

937

TRICHILININ–C

C33H44O7 (552.71)

[α]19 D : +22° (MeOH)

O

H

Amorphous powder

OAc

O H O

OH O

(1)

(1) SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Cramer) (Southern armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to 3rd instar larvae for 6–24 hours during which period 50% of one of the disks was consumed. (1)

(1) Zhou, J., Okamura, H., Iwagawa, T., Nakamura, Y., Nakayama, N, Tadera, K., and Nakatani, M. (1995) Heterocycles, 41, 2795.

© 2005 by CRC Press LLC

938

Opender Koul

TRICHLOROMETHYLPHTHALAZINE

C13H11ON2Cl3 (317.60)

Only spectral data given

OC2H5

N N

CCl3

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera eridania (Cramer) (Southern armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

260 ppm

Efficacy

Remarks

Feeding deterrence = 100%

Treatment to larvae.

(1) Rothgery, E.F. and Schroeder, H.A. (1979) U.S. Patent 4139622, 5 pp.

© 2005 by CRC Press LLC

Insect Antifeedants

TRI (CYCLOHEXYL) – TRIAZOL-1-YL) TIN (Peropal)

939

C20H35N3Sn (436.21)

M.p. : 218.8°

N N

Sn

N

(1, 2)

(1)

SOURCE: Commercial sample

(2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

0.013%

Feeding deterrence = 50.0%

0.11%

Feeding deterrence = 95.0%

Treatment to 170–190 mg body weight larvae. (2)

(1) The Agrochemicals Handbook (1986) Roy. Soc. Chem., U.K. (2) Ascher, K.R.S. (1980) Naturwissenschaften, 67, 312.

© 2005 by CRC Press LLC

940

Opender Koul

3 – TRIFLUROMETHANE SULFONYL BRUCEANTIN

C29H35O13F3S (680.64)

M.p. : 255–257°

OH COOCH3

HO O O

OCO H

SO2F3CO

O

O

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Heliothis virescens (Fab.) (Tobacco budworm)

Test Method Leaf disk choice test

Conc. / Dose 12.0 µg/cm2

Efficacy Feeding inhibition = 30–60% after 2 days and 0–30% after 6 days of treatment.

Remarks Treatment to 3rd instar larvae. (2)

(1) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H. (1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC

Insect Antifeedants

TRILOBOLIDE

941

C27H38O10 (522.59)

M.p. : 191–192° [α]20 D : +73.3° (MeOH)

OCOCH3

COO

OCO OH OH

O

O

(1, 2)

(1, 2)

SOURCE: Laser trilobum (L.) Borkh., gladich (Apiaceae)

(3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

1.0%

Feeding deterrence coefficient = 98

1. Treatment given to adults. (3)

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

1.0%

Feeding deterrence coefficient: Adults = 143 Larvae = 200

2. Treatment given to both adults and larvae. (3)

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

1.0%

Feeding deterrence coefficient = 137

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (3)

(1) Holub, M., DeGroote, R., Herout, V., and Sorm, F. (1968) Collect. Czech. Chem. Commun., 33, 2911. (2) Holub, M., Samek, Z., DeGroote, R., Herout, V., and Sorm, F. (1973) Collect. Czech. Chem. Commun., 38, 1551. (3) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

© 2005 by CRC Press LLC

942

Opender Koul

3,4,5 – TRIMETHOXYPHENOL

C9H12O4 (184.19)

M.p. : 148°

OH

OCH3

H3CO OCH3

(1,3)

(1, 2)

SOURCE: Synthetic, also occurring naturally in the sap of Antiaris toxicaria Lesch., Javanese upas tree (Moraceae)

(1, 3)

ACTIVITY PROFILE Test Insect Acalymma vittatum (Fab.) (Striped cucumber beetle)

Test Method Leaf disk choice test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding deterrence = 100% up to 4 hours

Treatment to adult beetles. (1)

0.5%

Feeding deterrence = 100% up to 24 hours

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378. (2) Dictionary of Natural Products, (1994) Chapman & Hall, London. (3) Kiliani, H. (1896) Arch. Pharm., 234, 438.

© 2005 by CRC Press LLC

Insect Antifeedants

1-(2,4,6-TRIMETHOXYPHENYL) BUTTRANS-2EN-1-ONE

943

C13H16O4 (236.27) M.p. : 95° (91–92°)

OCH3

OCH3

H3CO

O

(1)

(1, 2)

SOURCE: Arachniodes standishii (Moore) Ohwi., Japanese ryomenshida (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect Eurema hecabe mandarina DeLorza (Yellow butterfly)

Test Method Artificial diet feeding

Conc. / Dose

Efficacy

0.1%

Feeding deterrence ratio = 36.2%

0.01%

Feeding deterrence ratio = 34.3%

0.001%

Feeding deterrence ratio = 81.6%

Remarks Treatment to 5th instar larvae. (1)

(1) Numata, A., Katsuno, T., Yamamoto, K., Nishida, T., Takemura, T., and Seto, K. (1984) Chem. Pharm. Bull., 32, 325. (2) Chakrabarti, A. and Chakraborty, D.P. (1988) Phytochemistry, 27, 3683.

© 2005 by CRC Press LLC

944

Opender Koul

TULIRINOL

C17H22O5 (306.36)

M.p. : 204–206° [α]23 D : –51° (MeOH)

HO

H

H

O

O OAc CH2

(1)

(1)

SOURCE: Liriodendron tulipifera L., tulip poplar (Magnoliaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Lymantria dispar (L.) (Gypsy moth)

Leaf disk choice test

Efficacy

Remarks

50 µg/ml

Feeding deterrence = 31.0%

Treatment to larvae. (1)

250 µg/ml

Feeding deterrence = 47.0%

(1) Doskotch, R.W., Fairchild, E.H., Huang, C., Wilton, J.H., Beno, M.A., and Christoph, G.G. (1980) J. Org. Chem., 45, 1441.

© 2005 by CRC Press LLC

Insect Antifeedants

TYLOPHORINE

945

C24H27O4N (393.48) OCH3

M.p. : 287–288° (dec.) [α]25 D : –21.45° (CHCl3)

H3CO H

N

H3CO OCH3

(1)

(1, 2) SOURCE: Tylophora asthmatica Wight & Arn, tylophora (Asclepiadaceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Artificial diet feeding

Conc. / Dose 2.9 ppm

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to larvae of 60 to 70 mg body weight pre-starved for 4 h. Concentration = EC50 value. (2)

(1) Mulchandani, N.B. and Venkatachalam, S.R. (1976) Phytochemistry, 15, 1561. (2) Verma, G.S., Ramakrishna, V., Mulchandani, N.B., and Chadha, M.S. (1986) Entomol. Exp. Appl., 40, 99.

© 2005 by CRC Press LLC

946

Opender Koul

(±)TYLOPHORININE

C23H25O4N (379.46)

H3CO

M.p. : 246° (dec.)

OH H

N

H3CO OCH3

(1, 2)

(1)

SOURCE: Tylophora asthmatica Wight & Arn, tylophora (Asclepiadaceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Artificial diet feeding

Conc. / Dose 8.6 ppm

Efficacy

Remarks

Feeding deterrence = 50.0%

Treatment to larvae of 60 to 70 mg body weight pre-starved for 4 h. Concentration = EC50 value. (2)

(1) Govindachari, T.R., Pai, B.R., Prabhakar, S., and Savitri, T.S. (1965) Tetrahedron, 21, 2573. (2) Verma, G.S., Ramakrishna, V., Mulchandani, N.B., and Chadha, M.S. (1986) Entomol. Exp. Appl., 40, 99.

© 2005 by CRC Press LLC

Insect Antifeedants

947

C8H11ON-HCl (173.64)

TYRAMINE – HYDROCHLORIDE

M.p. : 269° (HCl)

NH2.HCl

OH

(1)

(1)

SOURCE: Sample test

(1)

ACTIVITY PROFILE Test Insect 1. Nilaparvata lugens Stal. (Brown planthopper)

Test Method Sucrose solution feeding

Conc. / Dose

Efficacy

Remarks

1000 ppm 100 ppm 10 ppm

Feeding deterrence = 86.0% 73.0 % 27.0%

1. Treatment to adult females. (1) FI50 = 36.94 ppm 2. Treatment to adult females. (1) FI50 = 36.33 ppm

2. Sogatella furcifera (Horvath) (Plant hopper)

Sucrose solution feeding

1000 ppm 100 ppm 10 ppm

Feeding deterrence = 82.0% 63.0% 35.0%

3. Laodelphax striatella (Fallen) (Planthopper)

Sucrose solution feeding

1000 ppm 100 ppm 10 ppm

Feeding deterrence = 80.0% 71.0% 54.0%

3. Treatment to adult females. (1)

4. Nephotettix cincticeps (Uhler.) (Fruit leafhopper)

Sucrose solution feeding

1000 ppm 100 ppm 10 ppm

Feeding deterrence = 97.0% 77.0% 42.0%

4. Treatment to adult females. (1) FI50 = 17.7 ppm FI50 calculated from Reference 1

LD50 (mice): 229 mg/kg (ivn.)

(2)

(1) Kurata, S. and Sogawa, K. (1976) Appl. Ent. Zool., 11, 89. (2) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

948

Opender Koul

UGANDENSIDIAL

C17H24O5 (308.37)

M.p. : 141–143° (137–140°) [α]20 D : –421.5° (CHCl3)

CHO OH CHO

H OAc

(1, 2)

(1,3) SOURCE: Warburgia ugandensis Sprague, African muziga (Canellaceae)

(1, 3)

ACTIVITY PROFILE Test Insect Spodoptera exempta (Walker) (Nutgrass armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

>0.1 ppm

Efficacy

Remarks

Feeding inhibition = Weaker than warburganal

Treatment to larvae. Quantitative data not recorded. (3)

(1) Brooks, C.J. and Draffan, G.H. (1969) Tetrahedron, 25, 2887. (2) Canonica, L., Corbella, A., Gariboldi, P., Jommi, G., Krepinsky, J., Ferrari, G., and Casagrande, C. (1969) Tetrahedron, 25, 3895. (3) Nakanishi, K. and Kubo, I. (1977) Israel J. Chem., 16, 28.

© 2005 by CRC Press LLC

Insect Antifeedants

UNDECANOIC ACID

949

C11H22O2 (186.29)

M.p. : 28.2–28.6° B.p. : 212.5°/100 mm

OH

O

(1)

(1)

SOURCE: Synthetic Hibiscus syriacus L., rose-of-sharon (Malvaceae)

(2) (3)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

1. Incisitermes minor (Hagen) (Western dry wood termite)

Paper towel disk test

2. Anthonomus grandis Bohem. (Boll weevil)

Plate bioassay

LD50 (mouse): 140 mg/kg (ivn.) (1) (2) (3) (4)

Efficacy

Remarks

0.05 mg/cm2

Feeding inhibition = 11.6% after 6-day exposure

1. Treatment to immature termites. Data calculated from Reference 2. (2)

100 µg/ feeding site

Feeding inhibition = About 87.0% after 3 h and 80.0% after 6 h in males and 84.0 and 78.0% in females, respectively.

2. Treatment to adult weevils. (3)

(4)

Cason, J. and Winans, W.R. (1950) J. Org. Chem., 15, 139. Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) J. Chem. Ecol., 13, 1087. Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

950

Opender Koul

10 – UNDECENOIC ACID

C11H20O2 (184.28)

M.p. : 24.5° B.p. : 275°/100 mm

OH

O

(1, 2)

(1)

SOURCE: Synthetic

(2)

ACTIVITY PROFILE Test Insect Incisitermes minor (Hagen) (Western dry wood termite)

Test Method

Conc. / Dose

Paper towel disk test

0.05 mg/cm2

Efficacy

Remarks

Feeding inhibition = 12.1% after 6-day exposure

Treatment to immature termites. (2) Data calculated from Reference 2.

LD50 (rats): 2500 mg/kg (oral) (1) Nogueira, P.L. and Prista, H.R. (1954) Anais. Fac. Farm. Porta., 14, 19. (2) Scheffrahn, R. H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39. (3) Opdyke, D.L.J. (1978) Food Cosmet. Toxicol., 16, 883.

© 2005 by CRC Press LLC

(3)

Insect Antifeedants

UNEDOSIDE

951

C14H20O9 (332.30)

OH

M.p. : 232–234°

H

O

O H

O - glu

(1)

(1)

SOURCE: Canthium euroides (Rubiaceae) Arbutus unedo L., arbutus (Ericaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Test Method

Conc. / Dose

Leaf disk choice test

100 ppm

Efficacy Feeding inhibition = 100%

Remarks 1. Treatment to larvae. (2)

2. Epilachna varivestis Mulsant (Mexican bean beetle)

Leaf disk choice test

100 µg/cm2

Feeding inhibition = 100%

2. Treatment to beetles. (2)

(1) Geisman, T.A., Knaack, W.F. Jr., and Knight, J.O. (1966) Tetrahedron Lett., 1245. (2) Kubo, I. and Nakanishi, K. (1978) Adv. Pestic. Sci., 2, 284.

© 2005 by CRC Press LLC

952

Opender Koul

URSINIOLIDE–A

C22H28O7 (404.46)

M.p. : 140–142° [α]20 D : –237°

OCO O

AcO

CH2 O O

(1)

(1, 2) SOURCE: Ursinia anthemoides (L.) Poiret. (Asteraceae)

(2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 80.2

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient Adults = 160.2 Larvae = 133.4

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 96.2

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Samek, Z., Holub, M., Rychlewska, U., Grabarczyk, H., and Dordz, B. (1979) Tetrahedron Lett., 28, 2691. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H. Drozdz, B., Daniewski, W.M., and Holub, M.. (1983) Prace. Nauk. Inst. Ochr. Roslin, 25, 91.

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Insect Antifeedants

(+) USNIC ACID

953

C18H16O7 (344.32)

M.p. : 203–204° [α]D : + 500° (CHCl3)

OH

OH

O

O

HO

O

O

(1, 2)

(1, 2)

SOURCE: Usnea lapponica Vain, lichen (Pteridophyta) U. filipendula Stirton, lichen (Pteridopyhta)

(2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

LD50 (mice): 838 mg/kg (oral)

Test Method

Conc. / Dose

Artificial diet choice test

10 µmol/g

Efficacy

Remarks

Feeding inhibition = 70.0%

Treatment to 3rd instar larvae for 24 h. Data calculated from Reference 2. (2)

(3)

(1) Dean, F.M., Halewood, P., Mongkolsuk, S., Robertson, A., and Whalley, W.B. (1953) J. Chem. Soc., 1250. (2) Emmerich, R., Giez, I., Lange, O.L., and Proksch, P. (1993) Phytochemistry, 33, 1389. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

954

Opender Koul

(–) USNIC ACID

C18H16O7 (344.32)

M.p. : 203–204° [α]20 D : –494° (CHCl3)

OH

OH

O

HO

O

O

O

(1, 2)

(1, 2)

SOURCE: Cladonia convoluta (Lam.) P. Cout., lichen (Pteridophyta) C. stellaris (Opiz.) Pouzar et vezda, lichen (Pteridopyhta)

(2)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Artificial diet choice test

10 µmol/g

Efficacy

Remarks

Feeding inhibition = 82.0%

Treatment to 3rd instar larvae for 24 h. Data calculated from Reference 2. (2)

(1) Dean, F.M., Halewood, P., Mongkolsuk, S., Robertson, A., and Whalley, W.B. (1953) J. Chem. Soc., 1250. (2) Emmerich, R., Giez, I., Lange, O.L., and Proksch, P. (1993) Phytochemistry, 33, 1389.

© 2005 by CRC Press LLC

Insect Antifeedants

UVIDIN–A

955

C15H24O3 (252.35)

M.p. : 123–124° [α]20 D : +151.1° (CHCl3)

HO

O

O

(1, 2)

(1, 2)

SOURCE: Lactarius uvidus Fr., mushroom (Russulaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

100 ppm

Feeding inhibition ratio = 92.4%

20 ppm

Feeding inhibition ratio = 23.0%

100 ppm

Feeding inhibition ratio = 28.0%

Remarks 1. Treatment to larvae. (3)

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk test

2. Treatment to beetles. (3)

(1) DeBernardi, M., Mellerio, G., Vidari, G., Vita-Finzi, P., and Fronza, G. (1980) J. Chem. Soc. Perkin Trans. I, 221. (2) DeBernardi, M., Mellerio, G., Vidari, G., Vita-Finzi, P., and Fronza, G. (1983) J. Chem. Soc. Perkin Trans. I, 2739. (3) Garlaschelli, L., Mellerio, G., Vidari, G., and Vita-Finzi, P. (1994) J. Nat. Prod., 57, 905.

© 2005 by CRC Press LLC

956

Opender Koul

UVIDIN–B

C15H24O4 (268.35)

M.p. : 180–181° [α]20 D : +171° (Me2CO)

HO

O HO O

(1, 2)

(1, 2) SOURCE: Lactarius uvidus Fr., mushroom (Russulaceae)

(1, 2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk test

Conc. / Dose 100 ppm

Efficacy Feeding inhibition ratio = 41.0%

Remarks 1. Treatment to larvae. (3)

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk test

100 ppm

Feeding inhibition ratio = 6.0%

2. Treatment to beetles. (3)

(1) DeBernardi, M., Mellerio, G., Vidari, G., Vita-Finzi, P., and Fronza, G. (1980) J. Chem. Soc. Perkin Trans. I, 221. (2) DeBernardi, M., Mellerio, G., Vidari, G., Vita-Finzi, P., and Fronza, G. (1983) J. Chem. Soc. Perkin Trans. I, 2739. (3) Garlaschelli, L., Mellerio, G., Vidari, G., and Vita-Finzi, P. (1994) J. Nat. Prod., 57, 905.

© 2005 by CRC Press LLC

Insect Antifeedants

UVIDIN–A LACTARINATE

957

C33H56O5 (532.80)

Waxy solid M.p. : 52–53° [α]20 D : + 101.8° (CHCl3)

OCO

O O

O

(1)

(1)

SOURCE: Lactarius uvidus Fr., mushroom (Russulaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk test

Conc. / Dose

Efficacy

100 ppm

Feeding inhibition ratio = 68.0%

20 ppm

Feeding inhibition ratio = 7.0%

100 ppm

Feeding inhibition ratio = 4.0%

Remarks 1. Treatment to larvae. (1)

2. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk test

2. Treatment to beetles.

(1) Garlaschelli, L., Mellerio, G., Vidari, G., and Vita-Finzi, P. (1994) J. Nat. Prod., 57, 905.

© 2005 by CRC Press LLC

(1)

958

Opender Koul

VACHANIC ACID

C15H24O3 (252.35)

M.p. : 174–176° [α]20 D : –45.6° (CHCl3)

CH2 HO

COOH

H

(1)

(1) SOURCE: Dittrichia viscosa (L.) Grenter, inula (Asteraceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 115.1

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient Adults = 99.0 Larvae = 160.3

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/cm3

Feeding deterrence coefficient = 18.8

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (1)

(1) Daniewski, W.M., Kroszczynski, W., Bloszyk, E., Dordz, B., Nawrot, J., Rychlewska, U., Budesinsky, M., and Holub, M.. (1986) Collect. Czech. Chem. Commun., 51, 1710.

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Insect Antifeedants

VASICINE

959

C11H12ON2 (188.23)

M.p. : 212° [α]14 D : –254° (CHCl3)

N

N OH

(1, 2)

(1) SOURCE: Justicia adhatoda L., vasaka (Acanthaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Aulacophora foveicollis (Lucas) (Red leaf beetle)

2. Epilachna vijintioctopunctata (Fab.) (Brinjal beetle)

LD50 (rats): 640 mg/kg (oral)

Test Method Leaf spray test

Leaf spray test

Conc. / Dose

Efficacy

0.05%

Feeding inhibition ratio = 33.0%

0.1%

Feeding inhibition ratio = 56.2%

0.05%

Feeding inhibition ratio = 73.3%

0.1%

Feeding inhibition ratio = 77.0%

Remarks 1. Treatment to adult beetles. (1)

2. Treatment to adults. (1)

(3)

(1) Saxena, B.P., Tikku, K., Atal, C.K., and Koul, O. (1986) Insect Sci. Applic., 7, 489. (2) Mehta, D.R., Naravane, J.S., and Desai, R.M. (1963) J. Org. Chem., 28, 445. (3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC

960

Opender Koul

VASICINOL

C11H12O2N2 (204.23)

M.p. : 272–273° (260°- dec.) [α]25 D : +2.5° (AcOH)

HO N

N OH

(1)

(1, 2, 3)

SOURCE: Justicia adhatoda L., vasaka (Acanthaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Aulacophora foveicollis (Lucas) (Red leaf beetle)

2. Epilachna vijintioctopunctata (Fab.) (Brinjal beetle)

Test Method Leaf spray test

Leaf spray test

Conc. / Dose

Efficacy

0.05%

Feeding inhibition ratio = 37.2%

0.1%

Feeding inhibition ratio = 69.7%

0.05%

Feeding inhibition ratio = 35.9%

0.1%

Feeding inhibition ratio = 57.7%

1. Treatment to adult beetles. (1)

2. Treatment to adults. (1)

(1) Saxena, B.P., Tikku, K., Atal, C.K., and Koul, O. (1986) Insect Sci. Applic., 7, 489. (2) Spath, E., et al. (1960) Monatsh. Chem., 1150. (3) Ghosal, S., Ballav, R., Chauhan, P.S., and Mehta, R. (1975) Phytochemistry, 14, 830.

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Remarks

Insect Antifeedants

VASICINONE

961

C11H10O2N2 (202.21)

M.p. : 200–201° [α]D : –129° (CHCl3)

O

N

N OH

(1)

(1, 2)

SOURCE: Justicia adhatoda L., vasaka (Acanthaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Aulacophora foveicollis (Lucas) (Red leaf beetle)

2. Epilachna vijintioctopunctata (Fab.) (Brinjal beetle)

Test Method Leaf spray test

Leaf spray test

Conc. / Dose

Efficacy

0.05%

Feeding inhibition ratio = 17.6%

0.1%

Feeding inhibition ratio = 51.8%

0.05%

Feeding inhibition ratio = 30.2%

0.1%

Feeding inhibition ratio = 56.5%

1. Treatment to adult beetles. (1)

2. Treatment to adults. (1)

(1) Saxena, B.P., Tikku, K., Atal, C.K., and Koul, O. (1986) Insect Sci. Applic., 7, 489. (2) Ghosal, S., Ballav, R., Chauhan, P.S., and Mehta, R. (1975) Phytochemistry, 14, 830.

© 2005 by CRC Press LLC

Remarks

962

Opender Koul

VERBENONE

C10H14O (150.22)

M.p. : 6.5° B.p. : 227–228° [α]18 D : +249.6°

O

(1, 2)

(1, 2) SOURCE: Commercial sample

(1)

ACTIVITY PROFILE Test Insect 1. Hylobius pales (Herbst.) (Pales weevil)

Test Method Twig dip treatment choice test

Conc. / Dose 10%

Efficacy Feeding inhibition = 61.5%

Remarks 1. Treatment to 22–65 mg body weight weevils for 24 h. Data calculated from Reference 1. (1)

2. Hylobius abietis L. (Pine weevil)

Twig dip assay

10%

Feeding inhibition = 45% approx. in choice situation and about 38% in nochoice situation

2. Treatment to adult weevils for 48 h. Data calculated from Reference 3. (3)

(1) Salom, S.M., Carlson, J.A., Ang, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407. (2) Banthorpe, D.V. and Whittaker, D. (1966) Chem. Rev., 66, 643. (3) Klepzig, K.D. and Schlyter, F. (1999) J. Econ. Entomol., 92, 644.

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Insect Antifeedants

VESTITOL

963

C16H16O4 (272.30)

M.p. : 156° (144–145°) [α]D : +21.6° (MeOH)

HO

O

OCH3

HO

(1, 2)

(1, 2, 3)

SOURCE: Trifolium repens L., grassland huia (Fabaceae)

(1)

ACTIVITY PROFILE Test Insect Heteronychus arator (Fab.) (Black beetle)

Test Method Artificial diet feeding

Conc. / Dose

Efficacy

200 µg/g

Feeding inhibition = 68.0%

100 µg/g

Feeding inhibition = 75.0%

10 µg/g

Feeding inhibition = 55.0%

Remarks Treatment to 3rd instar larvae after 24-h starvation. Data calculated from Reference 1. (1)

(1) Kurosawa, K., Ollis, W.D., Redman, B.T., Sutherland, I.O., Braga deOliveira, A., Gottlieb, O.R., and Alves, H.M. (1968) J. Chem. Soc. Chem. Commun., 1263. (2) Russel, G.B., Sutherland, O.R.W., Christmas, P.E., and Wright, H. (1982) NZ. J. Zool., 9, 145. (3) Kurosawa, K., Ollis, W.D., Redman, B.T., Sutherland, I.O., and Gottlieb, O.R. (1978) Phytochemistry, 17, 1413.

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964

Opender Koul

VINBLASTINE

C46H58O9N4 (810.99) OH N

M.p. : 211–216° [α]26 D : +42° (CHCl3)

C2H5

N N

C2H5

H3COOC H3CO

N

OCOCH3 H

OH COOCH3

(1, 2)

(3)

SOURCE: Catharanthus roseus (L.) G.Don., madagascar periwinkle (Apocynaceae)

(4)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Lamellar disk feeding

Conc. / Dose 0.04%

Efficacy

Remarks

Feeding inhibition = 55.4%

Treatment to larvae. Data calculated from Reference 4. Other alkaloids like catharanthine, vindoline, leurocristine, and ajmalicine were also evaluated but were not significantly active. (4)

LD50 (mice): 17 mg/kg (i.v.) (1) (2) (3) (4) (5)

(5)

Gorman, M., Neuss, N., and Svoboda, G.H. (1959) J. Am. Chem. Soc., 81, 4745. Moncrief, J.W. and Lipscomb, W.N. (1965) J. Am. Chem. Soc., 87, 4963. Neuss, N., Gorman, M., Svoboda, G.H., Maciak, G., and Beer, C.T. (1959) J. Am. Chem. Soc., 81, 4754. Meisner, J., Weissenberg, M., Pelevitch, D., and Aharonson, N. (1981) J. Econ. Entomol., 74, 131. (1983) Merck Index, p. 1427.

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Insect Antifeedants

VISMIN

965

C25H28O4 (392.49)

OH

OH

M.p. : 161–164° (impure)

O

OH

(1, 2)

(1)

SOURCE: Fruits of Vismia spp. (Clusiaceae)

(1)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Glass fiber disk test

10–3 M

Feeding inhibition = 61.24%

1. Treatment to last instar larvae. (1)

2. Heliothis virescens (Fab.) (Tobacco budworm)

Glass fiber disk test

10–3 M

Feeding inhibition = 56.56%

2. Treatment to last instar larvae. (1)

3. Locusta migratoria (L.) (Migratory locust)

Glass fiber disk test

10–3 M

Feeding inhibition = 79.22%

3. Treatment to last instar larvae. (1)

(1) Delle Monache, F., Ferrari, F., Bettolo, G.B.M., and Cuca Suarez, L.E. (1980) Planta Medica, 40, 340. (2) Simmonds, M.S.J., Blaney, W.M., DelleMonache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem. Ecol., 11, 1593.

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966

Opender Koul

VISMINONE–A (vismione A)

C23H26O6 (398.46)

M.p. : 140–141° [α]D : +54° (CHCl3)

O

OH

OH

OCH3 OAc

(1)

(1, 2) SOURCE: Vismia baccifera (L.) Tr. and Planch, achiote tigre (Clusiaceae)

(1,2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Glass fiber disk test

10–3 M

Feeding inhibition = 51.47%

1. Treatment to last instar larvae. (2)

2. Heliothis virescens (Fab.) (Tobacco budworm)

Glass fiber disk test

10–3 M

Feeding inhibition = 67.47%

2. Treatment to last instar larvae. (2)

3. Locusta migratoria (L.) (Migratory locust)

Glass fiber disk test

10–3 M

Feeding inhibition = 80.14%

3. Treatment to last instar larvae. (2)

(1) DelleMonache, F., Ferrari, F., Bettolo, G.B.M., Peny, M., Silvio, C., Fedeli, W., Gavuzzo, E., and Vaciago, A. (1979) Gazz. Chim. Ital., 109, 301. (2) Simmonds, M.S.J., Blaney, W.M., DelleMonache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem. Ecol., 11, 1593.

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Insect Antifeedants

VISMINONE–B (vismione B)

967

C21H22O5 (354.40)

M.p. : 200–202° [α]D : +24° (CHCl3)

O

OH

O

OCH3 OH

(1, 2)

(1)

SOURCE: Vismia baccifera (L.) Tr. and Planch, achiote tigre (Clusiaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera exempta (Walker) (Nutgrass armyworm)

Glass fiber disk test

10–3 M

Feeding inhibition = 69.69%

1. Treatment to last instar larvae. (2)

2. Heliothis virescens (Fab.) (Tobacco budworm)

Glass fiber disk test

10–3 M

Feeding inhibition = 58.98%

2. Treatment to last instar larvae. (2)

3. Locusta migratoria (L.) (Migratory locust)

Glass fiber disk test

10–3 M

Feeding inhibition = 100%

3. Treatment to last instar larvae. (2)

(1) Pinheiro, R.M., Quhae, M.M., Bettolo, G.B.M., and Monache, F.D. (1984) Phytochemistry, 23,1737. (2) Simmonds, M.S.J., Blaney, W.M., DelleMonache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem. Ecol., 11, 1593.

© 2005 by CRC Press LLC

968

Opender Koul

VISNAGIN

C13H10O4 (230.22)

O

M.p. : 144–145° (138–140°)

O

O

OCH3

(1, 2)

(1, 2)

SOURCE: Pimpinella monica Dalz., pimpinella (Apiaceae)

(1, 2)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Artificial diet assay

Conc. / Dose 62.2 ppm

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 4th instar larvae prestarved for 4 h. Treatment until 48 h. Concentration = EC50. (2)

(1) Spath, E., et al. (1941) Chem. Ber., 74, 1492. (2) Luthria, D.L., Ramakrishnan, V., and Banerji, A. (1993) J. Nat. Prod., 56, 671.

© 2005 by CRC Press LLC

Insect Antifeedants

VITEXIN

969

C21H20O10 (432.38)

M.p. : 269–270° (dec.) [α]20 D : –14.5° (pyridine)

CH2OH OH

O HO HO

HO

OH

O

OH

O

(1, 2)

(1, 2)

SOURCE: Semisynthetic

(3)

ACTIVITY PROFILE Test Insect 1. Schizaphis graminum (Rondani) (wheat aphid)

Test Method Lamellar disk feeding

Conc. / Dose 0.25%

Efficacy Feeding inhibition = 50.0%

Remarks 1. Treatment to 50–75 aphids at random for 24 h. (3)

2. Myzus persicae (Sulzer) (green peach aphid)

Artificial diet feeding

0.1%

Feeding inhibition = 50.0%

2. Treatment to 50–75 aphids at random for 8 h. (3)

(1) Evans, W.H., McGookin, A., Jurd, L., Robertson, A., and Williamson, W.R.N. (1957) J. Chem. Soc., 3510. (2) Horowitz, R.M. and Gentili, B. (1964) Chem & Ind., 498. (3) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC

970

Opender Koul

VOLKENSIN

C33H44O9 (584.71) O

M.p. : 185–187°

OH O O

O AcO

OH O

(1)

(1)

SOURCE: Melia volkensii Gurke, East African melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method Leaf disk choice test

Conc. / Dose 3.5 µg/cm2

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 3rd instar larvae for 15 h. Concentration = EC50. (1)

(1) Rajab, M.S., Bentley, M.D., Alford, A.R., and Mendel, M.J. (1988) J. Nat. Prod., 51, 168.

© 2005 by CRC Press LLC

Insect Antifeedants

971

VOLKENSIN HYDROXYLACTONE

O

C33H42O9 (582.69)

M.p. : 240–244° (dec.)

O O O

O AcO

OH O

(1)

(1)

SOURCE: Melia volkensii Gurke, East African melia (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera frugiperda (J.E. Smith) (Fall armyworm)

Test Method Leaf disk choice test

Conc. / Dose 6.0 µg/cm2

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 3rd instar larvae for 15 h. Concentration = EC50. (1)

(1) Rajab, M.S., Bentley, M.D., Alford, A.R., and Mendel, M.J. (1988) J. Nat. Prod., 51, 168.

© 2005 by CRC Press LLC

972

Opender Koul

VULPINIC ACID

C19H14O5 (322.32)

M.p. : 145–146°

O OCH3 OH

O

O

(1)

(1)

SOURCE: Letheria vulpina (L.) Hue, lichen (Pteridophyta)

(1)

ACTIVITY PROFILE Test Insect Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method

Conc. / Dose

Artificial diet choice feeding

10 µmol/g

Efficacy

Remarks

Feeding inhibition = 60.0%

Treatment to 3rd instar larvae for 24 h. Data calculated from Reference 1. (1)

(1) Emmerich, R., Giez, I., Lange, O.L., and Proksch, P. (1993) Phytochemistry, 33, 1389. (2) Rao, Y.S. (1976) Chem. Rev., 76, 625.

© 2005 by CRC Press LLC

Insect Antifeedants

WARBURGANAL

973

C15H22O3 (250.34)

M.p. : 106–107° [α]22 D : +260° (CHCl3)

CHO OH CHO

H

(1)

(1, 2)

SOURCE: Warburgia ugandensis Sprague, African muziga (Canellaceae)

(1)

ACTIVITY PROFILE Test Insect 1. Spodoptera exempta (Walker) (Nutgrass armyworm)

2. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Leaf disk choice test

Leaf disk choice test

Conc. / Dose 0.1 ppm

10 ppm

Efficacy

Remarks

Feeding inhibition = Minimum level to show inhibition.

1. Treatment to larvae.

Feeding inhibition = Minimum level to show inhibition.

2. Treatment to larvae.

(2)

(2)

3. Schistocerca gregaria Forsk. (Desert locust)

Glass fiber disk test

0.01%

Feeding inhibition = 85–90%

3. Treatment to 5th instar larvae. (2)

4. Locusta migratoria (L.) (Migratory locust)

Glass fiber disk test

0.01%

Feeding inhibition = 85–90%

4. Treatment to 5th instars. (2)

5. Leptinotarsa decemlineata (Say) (Colorado potato beetle)

Leaf disk dual-choice assay

5 mM

Feeding inhibition = 79.0%

5. Treatment to larvae of 90–120 mg body weight for a period of 3 h. (3)

LD50 (mice): 20.4 mg/kg (s.c.)

(2)

(1) Kubo, I., Lee, Y., Pettei, M., Pilkiewicz, F, and Nakanishi, K. (1976) J. Chem. Soc. Chem. Commun., 1013. (2) Nakanishi, K. (1980) In Insect Biology in the Future, Academic Press, pp. 603–611. (3) Gols, G.J.Z., van Loon, J.J.A., and Messchendorp, L. (1996) Entomol. Exp. Appl., 79, 69.

© 2005 by CRC Press LLC

974

Opender Koul

WILFORINE

C43H49O18N (867.86) AcO

OAc OAc

M.p. : 169–170° [α]25 D : + 30° (Acetone)

BzO

OAc

O O OH O

O

OAc O

N

(1)

(1, 2) SOURCE: Maytenus rigida Mart. (Celastraceae)

(2)

ACTIVITY PROFILE Test Insect 1. Locusta migratoria (L.) (Migratory locust)

Test Method Filter paper disk test

Conc. / Dose

Efficacy

5 × 10–5% dry weight

Feeding deterrence = 50%

Remarks 1. Treatment to larvae. (2)

1 × 10–1% dry weight

2. Schistocerca gregaria (Forsk.) (Desert locust)

Filter paper disk test

3. Locustana paradalina (Walker) (Locust)

Filter paper disk test

4. Helicoverpa zea (Boddie) (Corn earworm)

Wet filter paper disk test

1 × 10–2%

5. Helicoverpa armigera (Hubner) (Grampod borer)

Wet filter paper disk test

2 × 10–2%

6. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Wet filter paper disk test

1 × 10–3%

Feeding deterrence = 50%

2. Treatment to larvae. (2)

5 × 10–4% dry weight

Feeding deterrence = 50%

3. Treatment to larvae. (2)

Feeding deterrence = 50%

4. Treatment to larvae. (2)

Feeding deterrence = 50%

5. Treatment to larvae. (2)

Feeding deterrence = 50%

6. Treatment to larvae.

(1) Beroza, M. (1951) J. Am. Chem. Soc., 73, 3656. (2) Monache, F.D., Bettolo, G.B.M., and Bernays, E.A. (1984) Z. Angew. Entomol., 97, 406.

© 2005 by CRC Press LLC

(2)

Insect Antifeedants

WITHAFERIN–A

975

C28H38O6 (470.61)

M.p. : 252–253° [α]28 D : + 125° (CHCl3)

CH2OH H O

O

H O

O OH

(1, 2)

(1, 2)

SOURCE: Withania somnifera (L.) Dunal., withania (Solanaceae)

(3)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf residue test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding inhibition = 98.8%

0.05%

Feeding inhibition = 57.7%

Treatment to 4th instar larvae for 48 h. Data calculated from Reference 3. (3)

0.025%

Feeding inhibition = 24.7%

FI50 = 0.039% Calculated from Reference 3.

LD50 (mouse): 54 mg/kg (ipr.) (1) Lavie, D., Glotter, E., and Shvo, Y. (1965) J. Chem. Soc., 7517. (2) Lavie, D., Glotter, E., and Shvo, Y. (1965) J. Org. Chem., 30, 1774. (3) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197. (4) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC

(4)

976

Opender Koul

WITHANICANDRIN

C28H36O6 (468.59)

M.p. : 267–269° [α]D : + 105° (CHCl3)

O

O

O

H O

OH

O

(1)

(1, 2) SOURCE: Nicandra physaloides (L.) Gaertn., apple-of-Peru (Solanaceae)

(1, 2)

ACTIVITY PROFILE Test Insect

Test Method

Conc. / Dose

Efficacy

Remarks

1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Styropor method

100 ppm

Feeding inhibition = 6.0%

1. Treatment to early 6th instar larvae for 48 h. Treatment given in a mixture with daturalactone. (2)

2. Epilachna varivestis Muls. (Mexican bean beetle)

Bean leaf test

100 ppm

Feeding inhibition = 100%

2. Treatment to 4th instar larvae for 48 h. (2)

10 ppm

Feeding inhibition = 100%

100 ppm

Feeding inhibition = 44.8%

3. Tribolium castaneum (Herbst.) (Red flour beetle)

Yeast diet feeding

3. Treatment to 0–3 hour old larvae for 14 days. (2) Data calculated from Reference 2.

(1) Kirson, I., Lavie, D., Subramanian, S.S., Sethi, P.D., and Glotter, E. (1972) J. Chem. Soc. Perkin Trans I, 2109. (2) Ascher, K.R.S., Eliyahu, M., Glotter, E., Goldman, A., Kirson, I., Abraham, A., Jacobson, M., and Schmutterer, H. (1987) Phytoparasitica, 15, 15.

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Insect Antifeedants

WITHANOLIDE–D

977

C28H38O6 (470.61)

M.p. : 253–255° [α]D : + 80° (CHCl3)

OH O

O

H O

O OH

(1, 2)

(1, 2, 3)

SOURCE: Withania somnifera (L.) Dunal., withania (Solanaceae)

(3)

ACTIVITY PROFILE Test Insect Epilachna varivestis Muls. (Mexican bean beetle)

Test Method Leaf residue test

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding inhibition = 77.8%

Treatment to 4th instar larvae for 48 h. (3)

0.05%

Feeding inhibition = 76.5%

FI50 = 0.036% Data calculated from Reference 3.

0.025%

Feeding inhibition = 28.9%

(1) Lavie, D., Kirson, I., and Glotter, E. (1968) Israel J. Chem., 6, 671. (2) Kirson, I., Glotter, E., Abraham, A., and Lavie, D (1970) Tetrahedron, 26, 2209. (3) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197.

© 2005 by CRC Press LLC

978

Opender Koul

WITHANOLIDE–E

C28H38O7 (486.60)

M.p. : 167–168° [α]D : + 103.5° (CHCl3)

OH O

O

OH O

OH O

(1, 2) (1, 2)

SOURCE: Physalis peruviana L., Peruvian groundcherry (Solanaceae)

(3)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Styropor method

Conc. / Dose 0.1% 0.005% 0.001% 0.0005%

2. Epilachna varivestis Muls. (Mexican bean beetle)

Leaf residue test

Efficacy Feeding 100% Feeding 95.9% Feeding 68.2% Feeding 14.4%

inhibition = inhibition =

Remarks 1. Treatment to larvae of 170–190 mg body weight. (3)

inhibition = inhibition =

0.1%

Feeding inhibition = 100%

0.05%

Feeding inhibition = 100%

FI50 = 0.0089% Data calculated from Reference 3. 2. Treatment to 4th instar larvae for 48 h. (4) Data calculated from Reference 4.

(1) Glotter, E., Abraham, A., Gunzberg, G., and Kirson, I. (1977) J. Chem. Soc. Perkin Trans I, 341. (2) Kirson, I., Abraham, A., Sethi, P.D., Subramanian, S.S., and Glotter, E. (1976) Phytochemistry, 15, 340. (3) Ascher, K.R.S., Nemny, N.E., Eliyahu, M., Kirson, I., Abraham, A., and Glotter, E. (1980) Experientia, 36, 998. (4) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197.

© 2005 by CRC Press LLC

Insect Antifeedants

WITHANOLIDE–S

979

C28H40O8 (504.62) M.p. : 272° (dec.) [α]D : + 95.5° (MeOH)

OH O

O

OH O

OH

OH OH

(1)

(1, 2) SOURCE: Physalis peruviana L., Peruvian groundcherry (Solanaceae)

(2)

ACTIVITY PROFILE Test Insect 1. Spodoptera littoralis (Boisd.) (Egyptian cotton leaf worm)

Test Method Styropor method

Conc. / Dose

Efficacy

Remarks

0.1%

Feeding inhibition = 41.1%

0.01%

Feeding inhibition = 44.2%

1. Treatment to larvae of 170–190 mg body weight. (2) Data calculated from Reference 2.

(1) Glotter, E., Abraham, A., Gunzberg, G., and Kirson, I. (1977) J. Chem. Soc. Perkin Trans I, 341. (2) Ascher, K.R.S., Nemny, N.E., Eliyahu, M., Kirson, I., Abraham, A., and Glotter, E. (1980) Experientia, 36, 998.

© 2005 by CRC Press LLC

980

Opender Koul

XANTHOTOXIN

C12H8O4 (216.19)

O

O

M.p. : 146°

O OCH3

(1, 2)

(2)

SOURCE: Oryxa japonica Thumb., Japanease kokusagi (Rutaceae) Also from Angelica silvestris L., angelica (Apiaceae) Atalantia recemosa Wight and Arn, wild lime (Rutaceae)

(1) (4) (5)

ACTIVITY PROFILE Test Insect 1. Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method

Conc. / Dose

Efficacy

Remarks 1. Treatment to 3rd instar larvae. (1) Treatment to 4th instar larvae starved for 4 h. Treatment duration = 48 h. (4)

Leaf disk test

100 ppm

Feeding inhibition = 50.0%

Artificial diet feeding

31.0 ppm

Feeding inhibition = 50.0%

2. Periplaneta americana (L.) (American cockroach)

Sugar pellet method

0.1 mg/1.5 g pellet

Feeding inhibition = 54.0%

2. Treatment to adult cockroach. (3)

3. Blatella germanica (L.) (German cockroach)

Sugar pellet method

0.1 mg/1.5 g pellet

Feeding inhibition = 43.0%

3. Treatment to adult cockroach. (3)

4. Stylopyga rhombifolia (Cockroach)

Sugar pellet method

0.1 mg/1.5 g pellet

Feeding inhibition = 88.0%

4. Treatment to adults.

Leaf disk choice test

14.25 µg/cm2

Feeding inhibition = 45.3%

57.0 µg/cm2

Feeding inhibition = 97.6

5. Peridroma saucia (Hubner) (Variegated cutworm)

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(3) 5. Treatment to 5th instar larvae for 5 h. (4)

Insect Antifeedants

6. Pieris rapae crucivora Boisd. (Cabbage butterfly)

Leaf disk dualchoice test

5 × 10–7 mol/cm2

Feeding inhibition = 28.1%

981

6. Treatment to 5th instar larvae prestarved for 3 h. Treatment duration = 2 h. (6)

LD50 (rats): 791 mg/kg (oral)

(7)

(1) Yajima, T., Kato, N., and Munakata, K. (1977) Agric. Biol. Chem., 41, 1263. (2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 204. (3) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701. (4) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194. (5) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem., 37, 1435. (6) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130. (7) (1981) IARC Monograph, 24, 101.

© 2005 by CRC Press LLC

982

Opender Koul

XANTHOTOXOL ETHYL ETHER

C13H10O4 (230.22)

M.p. : 104–106°

OC2H5 H

O

O

O

H

(1)

(1)

SOURCE: Synthetic

(1)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Artificial diet assay

Conc. / Dose 23.0 ppm

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 4th instar larvae prestarved for 4 h. Treatment duration = 48 h. Concentration = EC50 value. (1)

(1) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem., 37, 1435.

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Insect Antifeedants

XANTHOXYLETIN

O

983

C15H14O4 (258.27)

O

M.p. : 132.5–134°

O

OCH3

(1, 2)

(1, 2)

SOURCE: Clausena anisata Hook F., samanobere (Rutaceae)

(2)

ACTIVITY PROFILE Test Insect Spodoptera exempta (Walker) (Nutgrass armyworm)

Test Method Leaf disk test

Conc. / Dose 100 ppm 500 ppm

Efficacy

Remarks

Feeding inhibition = Effective deterrent

Treatment to larvae. No quantitative data recorded.

(1) Virkov, J. and Sednnera, P. (1972) Phytochemistry, 11, 2647. (2) Gebreyesus, T. and Chapya, A. (1983) In Natural Products for Innovative Pest Management, Current Themes in Tropical Science, T.R. Odhiambo (ed.), Pergamon Press, Oxford, 237–241.

© 2005 by CRC Press LLC

984

Opender Koul

XANTHYLETIN

C14H12O3 (228.24)

O

O

M.p. : 131.5° (127–129°)

O

(1, 2)

(2, 3)

SOURCE: Boenninghausenia albiflora (Hook.) Reichb., flea plant (Rutaceae) Atalantia racemosa Wight and Arn, wild lime (Rutaceae)

(2) (4)

ACTIVITY PROFILE Test Insect Spodoptera litura (Fab.) (Tobacco armyworm)

Test Method Artificial diet assay

Conc. / Dose 870 ppm

Efficacy

Remarks

Feeding inhibition = 50.0%

Treatment to 4th instar larvae prestarved for 4 h. Treatment duration = 48 h. Concentration = EC50 value. (2)

Leaf disk test

(1) (2) (3) (4)

2500 ppm

Feeding inhibition = 100% within 2 h.

Treatment to 3rd instar larvae. Compound termed as relative antifeedant as activity retards after 6 h. (4)

King, F.E., Housley, J.R., and King, T.J. (1954) J. Chem. Soc., 1392. Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045. Bowden, B.F., Cleaver, L., Ndalut, P.K., Ritchie, E., and Taylor, W.C. (1975) Aust. J. Chem., 28, 1393. Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem., 37, 1435.

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Insect Antifeedants

XERANTHOLIDE

985

C15H18O3 (246.31)

M.p. : 190–192° (183°) [α]20 D : +223.3° (CHCl3)

H

O

O

O CH2

(1)

(1)

SOURCE: Xeranthemum cylindraceum Sibth and Smith, lilac stars (Asteraceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

2. Tribolium confusum Duv. (Confused flour beetle)

3. Trogoderma granarium Everts (Khapra beetle)

Test Insect

Efficacy

Remarks

8 mg/cm3

Feeding deterrence coefficient = 51–100

1. Treatment given to adults.

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient Adults = 51–100 Larvae = 101–150

2. Treatment given to both adults and larvae.

Wafer disk test

8 mg/cm3

Feeding deterrence coefficient = 101–150

3. Treatment given to larvae. Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Samek, Z., Holub, M., Dordz, B., Grabarczyk, H., and Hladon, B. (1977) Collect. Czech. Chem. Commun., 42, 2441. (2) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC

986

Opender Koul

XYLOMOLLIN

C12H18O7 (274.27)

M.p. : 138–139°

COOCH3 H OCH3

O

O

O H OH

(1, 2)

(1, 2)

SOURCE: Xylocarpus molluscensis Roem. (Meliaceae)

(1)

ACTIVITY PROFILE Test Insect Spodoptera exempta (Walker) (Nutgrass armyworm)

Test Method Leaf disk choice test

Conc. / Dose 1000 ppm

Efficacy Feeding inhibition = Effective deterrent

Remarks Treatment to 3rd instar larvae. (3) No quantitative data given.

(1) Kubo, I., Miura, I., and Nakanishi, K. (1976) J. Am. Chem. Soc., 98, 6704. (2) Nakane, M., Hutchinson, C.R., van Engen, D., and Clardy, J. (1978) J. Am. Chem. Soc., 100, 7079. (3) Kubo, I. and Nakanishi, K. (1977) In Host Plant Resistance to Pests, ACS Symp. Ser., 62, 165.

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Insect Antifeedants

YATEIN

987

C22H24O7 (400.43)

[α]20 D : –28.4° (CHCl3)

H O O O H

H3CO

O

OCH3 OCH3

(1)

(1) SOURCE: Libocedrus yateensis Guill., South incense cedar (Cupressaceae)

(2)

ACTIVITY PROFILE Test Method

Conc. / Dose

1. Sitophilus granarius (L.) (Grain weevil)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 189

1. Treatment given to adults.

2. Tribolium confusum Duv. (Confused flour beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient Adults = 158 Larvae = 143

2. Treatment given to both adults and larvae.

3. Trogoderma granarium Everts (Khapra beetle)

Wafer disk test

10 mg/ml

Feeding deterrence coefficient = 177

3. Treatment given to larvae.

Test Insect

Efficacy

Remarks

Neutral value = 0 Absolute feeding deterrence value = 200 (2)

(1) Erdtman, H. and Harmatha, J. (1979) Phytochemistry, 18, 1495. (2) Harmatha, J. and Nawrot, J. (1984) Biochem. Syst. Ecol., 12, 95.

© 2005 by CRC Press LLC