Insecticides with Novel Modes of Action: Mechanisms and Application

304 Pages·1998·10.771 MB·English

by  I. Ishaaya, A. R. Horowitz (auth.), Prof. Dr. Isaac Ishaaya, Prof. Dr. Danny Degheele (eds.)

Applied Agriculture
Co-ordinating Editor:
B. Yaron
Editors:
B.L. McNeal, F. Tardieu
H. Van Keulen, D. Van Vleck
Springer-Verlag Berlin Heidelberg GmbH
Isaac Ishaaya Danny Degheele t (Eds.)
Insecticides
with Novel Modes
of Action
Mechanisms and Application
With 40 Figures and 48 Tables
t
Springer
Prof. Dr. I. Ishaaya
Dept. of Entomology
Agricultural Research Organization
The Volcani Center, Bet Dagan 50250
Israel
Prof. Dr. Danny Degheelet
ISSN 1433-7576
ISBN 978-3-642-08314-3 ISBN 978-3-662-03565-8 (eBook)
DOI 10.1007/978-3-662-03565-8
Librltry 0/ Congress Clttltloging-in'Publiclttion DMIt
Insecticides with novel modes of action: mechanisms and application/
Isaac Ishaaya, Danny Degheele, editors.
p. cm. - (Applied agriculture)
Includes bibliographical references and index.
1. Insecticides. 2. Insecticides-Mechanism of action.
1. Ishaaya. 1. H. Degheele, Danny, 1941-. III, Series.
SB951.5.166 1997 97-22924
632' .9517 -dc21 CIP
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Cl Springer-Verlag Berlin Heidelberg 1998
Originally published by Springer-Verlag Berlin Heidelberg New York in 1998.
Softcover reprint of the hardcover 1s t edition 1998
The use of registered names, trademarks, etc. in this publication does not imply, even in the absence of a
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Cover design: Design & Production, Hcidelberg
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Preface
The future of insect control looked very bright in the 1950s and 1960s with
new insecticides constantly coming onto the market. Today, however, whole
classes of pesticide chemistry have fallen by the wayside due to misuse which
generated resistance problems reaching crisis proportions, severe adverse effects
on the environment, and public outcry that has led to increasingly stricter
regulation and legislation. It is with this background, demanding the need for
safer, environmentally friendly pesticides and new strategies to reduce resistance
problems, that this book was written.
The authors of the various chapters have a wealth of experience in pesticide
chemistry, biochemical modes of action, mechanism of resistance and application,
and have presented concise reviews. Each is actively involved in thedevelopment
of new groups of pesticide chemistry which led to the development of novel
insecticides with special impact in controlling agricultural pests. Emphasis has
been given to insecticides with selective properties, such as insect growth regulators
(chitin synthesis inhibitors, juvenile hormone mimics, ecdysone agonists),
chloronicotinyl insecticides (imidacloprid, acetamiprid), botanical insecticides (neem,
plant oils), pymetrozine, diafenthiuron, pyrrole insecticides, and others. The
importance of these compounds, as components in integrated pest management
programs and in insecticide resistance management strategies, is discussed. The
data presented are essential in establishing new technologies and developing novel
groups of compounds which will have impact on our future agricultural practices.
This book is intended to serve as a text for researchers, university professors,
and graduate students involved in developing new groups of insecticides for
crop protection and field crop management, and as a guide or reference book
for farm advisors, pest control operators, and practical farmers.
In the preparation of the manuscript, the editors and the authors are indebted
to the reviewers of the various chapters for valuable suggestions and criticism:
KR.S. Ascher (Israel), M. Cahill (UK), B. Darvas (Hungary), D. Degheele
(Belgium), 1. Denholm (UK), A.R. Horowitz (Israel), 1. Ishaaya (Israel), A.
McCaffery (UK), H. Oberlander (USA), D.L. Silhacek (USA), G. Smagghe
(Belgium), P. Weintraub (Israel), and M.E. Whalon (USA). The editors are also
thankful to Mrs. Svetlana Kontsedalov (Israel) for her patience in typing and
organizing the various sections of this book and to Mrs. Eulalie Ishaaya-van
Hoye for assisting in organizing the subject index.
Isaac Ishaaya
Contents
Insecticides with Novel Modes of Action: An Overview
1. ISHAAYA and A.R. HORoWITz................................................................ 1
1 Introduction 1
2 Insect Growth Regulators 2
2.1 Chitin Synthesis Inhibitors 2
2.2 Juvenile Hormone Mimics 6
2.3 Ecdysone Agonists 8
3 Nicotinyl Insecticides 10
3.1 Imidacloprid and Acetamiprid 10
4 Miscellaneous 12
4.1 Diafenthiuron 12
4.2 Pymetrozine 14
4.3 Biological Insecticides 15
4.3.1 Avermectins 15
4.3.2 Bacillus thuringiensis 16
4.4 Neem Extract 17
5 Conclusions 17
References 18
Ecdysone Agonists: Mechanism and Biological Activity
G. SMAGGHE and D. DEGHEELE ................................................................ 25
1 Introduction 25
2 Ecdysteroid-Specific Mode of Action 25
2.1 Moulting and Feeding 25
2.2 Specificity for Insecta 27
2.3 Organ Culture and Cellular Effects 29
2.4 Molecular Biology Studies 30
2.5 Receptor Binding 31
2.6 Neurotoxic Mechanism 32
2.7 Action in Adult Insects 32
3 IGRs in Insect Control 33
References 36
VIII Contents
Pymetrozine: A Novel Insecticide Mfecting Aphids and Whiteflies
D. FUOG, S.J. FERGUSSON and C. FLÜCKIGER ............................................ 40
1 Introduction 40
2 Names and Physicochemical Properties 40
3 Mode of Action 41
4 Toxicology 42
5 Spectrum of Activity 42
6 Use Recommendations 45
7 Effects on Virus Transmission 45
8 Summary 47
References 49
Imidacloprid, a Novel Chloronicotinyl Insecticide: Biological Activity
and Agricultural Importance
A. ELBERT, R. NAUEN and W. LEICHT ...................................................... 50
1 Introduction 50
2 Biological Activity 51
2.1 Efficacy on Target Pests 51
2.1.1 Foliar Application 51
2.1.2 Soil Application and Seed Treatment 51
2.2 Systemicity 52
2.2.1 Translocation in Winter Wheat 53
2.2.2 Translocation in Cotton 53
2.3 Sublethal Effects 56
2.3.1 Antifeedant Effect 56
2.3.2 Reduction of Aphid Viability 57
2.4 Action on Resistant Pest Species 58
2.4.1 Aphids 58
2.4.2 Whiteflies 58
2.4.3 Leafhoppers and Planthoppers 60
2.4.4 Colorado Potato Beetle 60
3 Mode of Action and Selectivity 60
3.1 Mode of Action on Insects and Vertebrates 60
3.2 Selectivity on Arthropods 61
4 Agricultural Importance 62
4.1 Rice 64
4.2 Cotton 65
4.3 Vegetables 67
4.4 Cereals 68
5 Summary 70
References 71
Buprofezin: A Novel Chitin Synthesis Inhibitor Mfecting Specifica1ly
Planthoppers, Whiteflies and Scale Insects
A. DE COCK and D. DEGHEELE .... ............. ............ ........ ......... .................. 74
1 Introduction 74
Contents IX
2 Mode of Action 74
3 Fidds of Application 78
3.1 Planthoppers and Leathoppers 79
3.2 Whiteflies 79
3.3 Scales and Mealybugs 80
3.4 PsylHdae 82
3.5 Others 82
4 Residues 82
5 Environmental Fate 83
6 Resistance 83
7 Toxicity to Non-Target Organisms 84
8 Conclusions 87
References 87
New Perspectives on the Mode of Action of Benzoylphenyl
Urea Insecticides
H. OBERLANDER and D.L. SIUIACEK......................................................... 92
1 Introduction 92
2 Chitin Synthesis and Inhibition in J1itro 94
2.1 Cdl Lines 94
2.2 Organ Cultures 94
3 Transport Hypotheses 95
3.1 Dolichol 95
3.2 Precursor Uptake 96
3.3 Precursor Export 97
4 Ultrastructural Analysis 99
5 Protein Synthesis 100
6 Conclusions 102
References 103
Bacillus thuringiensis: Use and Resistance Management
M.E. WHALON and W.H. MCGAUGHEY .................................................... 106
1 Introduction 106
2 Mode of Action 107
3 Classification and Specificity of B.t. Toxins 109
4 B.t. Specificity 110
5 Insect Resistance to B.t. 111
5.1 E..esistance Reported to Date 111
5.2 Mechanisms of R;esistance 113
5.3 Behavioral Resistance 115
5.4 Resistance Genetics 116.
5.5 B.t. Resistance Stability 117
5.6 B.t. Resistance Costs 118
6 Resistance Management 118
6.1 General Considerations 118
6.2 Specific Strategies for Managing Resistance 121
6.2.1 Rotation or Alternation 121
x Contents
6.2.2 Mixtures 122
6.2.3 Refugia 124
6.2.4 Low Doses 124
6.2.5 High Doses 125
6.2.6 Specific Gene Promoters 126
6.3 Previous Resistance Management Programs 127
7 Conclusions 128
References 129
Pyrrole Insecticides: A New Class of Agriculturally
Important Insecticides Functioning as Uncouplers of
Oxidative Phosphorylation
D.A. HUNT and M.F. TREACY .................................................................. 138
1 Introduction 138
2 Relationship of Physicochemical Parameters to Uncoupling 139
3 Structure-Activity Relationships 139
3.1 Variation of Substitution at the Two-Position of the
Pyrrole Ring 139
3.2 Variation of Aryl Substitution for 2-Arylpyrroles 140
3.3 Variation of the Electron Withdrawing Group at
the Three-Position of the Pyrrole Ring 141
3.4 Variation of Substituents at the Four- and Five-Positions of
the Pyrrole Ring 141
3.5 Activity of 2-Arylpyrroles with Trifluoromethyl Substitution 142
4 Overview of Structure-Activity Trends 144
5 Bioactivity and Pharmacodynamics of CL 303,630 145
5.1 Pesticidal Properties and Target Spectrum 145
5.2 Mechanism of Action 145
5.3 Insect Age-Dependent Sensitivity and Insecticide Resistance 147
6 Conclusions 149
References 150
Avermectins: Biochemica1 Mode of Action, Biologica1 Activity and
Agricultural Importance
R.K. JANSSON and R.A. DYBAS .................................................................. 152
1 Introduction 152
l.1 Discovery 152
2 Biochemical Mode of Action 155
3 Biological Activity 157
3.1 Spectrum and Potency of Avermectins Against
Agricultural Pests 157
3.2 Photostability and Translaminar Movement 160
4 Application in Agriculture 161
4.1 Crop Applications 161
4.2 Selectivity/ IPM Compatibility 162
4.3 Resistance 164