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Green Trends in Insect Control RSC Green Chemistry Series Editors: James H Clark, Department of Chemistry, University of York, York, UK George A Kraus, Department of Chemistry, Iowa State University, Iowa, USA Andrzej Stankiewicz, Delft University of Technology, Delft, The Netherlands Titles in the Series: 1: The Future of Glycerol: New Uses of a Versatile Raw Material 2: Alternative Solvents for Green Chemistry 3: Eco-Friendly Synthesis of Fine Chemicals 4: Sustainable Solutions for Modern Economies 5: Chemical Reactions and Processes under Flow Conditions 6: Radical Reactions in Aqueous Media 7: Aqueous Microwave Chemistry 8: The Future of Glycerol: 2nd Edition 9: Transportation Biofuels: Novel Pathways for the Production of Ethanol, Biogas and Biodiesel 10: Alternatives to Conventional Food Processing 11: Green Trends in Insect Control How to obtain future titles on publication: A standing order plan is available for this series. A standing order will bring delivery of each new volume immediately on publication. For further information please contact: BookSalesDepartment,RoyalSocietyofChemistry,ThomasGrahamHouse, Science Park, Milton Road, Cambridge, CB4 0WF, UK Telephone: +44(0)1223 420066,Fax:+44(0)1223420247 Email:[email protected] Visit our website at http://www.rsc.org/Shop/Books/ Green Trends in Insect Control Edited By O´ scar Lo´pez and Jose´ G. Ferna´ndez-Bolan˜ os Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Spain RSC Green Chemistry No. 11 ISBN: 978-1-84973-149-2 ISSN: 1757-7039 A catalogue record for this book is available from the British Library r Royal Society of Chemistry 2011 All rights reserved Apart from fair dealing for the purposes of research for non-commercial purposes or for private study, criticism or review, as permitted under the Copyright, Designs and Patents Act 1988 and the Copyright and Related Rights Regulations 2003, this publication may not be reproduced, stored or transmitted, in any form or by any means, without the prior permission in writing of The Royal Society of Chemistry or the copyright owner, or in the case of reproduction in accordance with the terms of licences issued by the Copyright Licensing Agency in the UK, or in accordance with the terms of the licences issued by the appropriate Reproduction Rights Organization outside the UK. Enquiries concerning reproduction outside the terms stated here should be sent to The Royal Society of Chemistry at the address printed on this page. The RSC is not responsible for individual opinions expressed in this work. Published by The Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge CB4 0WF, UK Registered Charity Number 207890 For further information see our web site at www.rsc.org Preface This book is part of the Green Chemistry series published by the Royal Society of Chemistry, and is designed to provide a modern overview of the current status of insecticides. We present the current approaches for insect pest control as green alternatives to classical agrochemicals, which should be of interest to a vast group of researchers: agrochemists, biochemists, chemists, toxicologists, etc. Throughout the book, the different approaches to pest control which involve ‘‘greener chemicals’’ in particular are emphasized. In the literature there are numerous examples of texts making a comprehensive treatment of specific aspects of agrochemicals (such as toxicity, analytical measurements of pesticides and their derivatives in the environment and in living organisms or practical uses of insecticides), but there are few attempts of bringing together the wide variety of topics covered in this book. With this publication, we intend to provide a useful guide for a broadrange of readers, from students,to teachers or professionals inthe agrochemical sector. In each of the chapters, the following information is taken into account: a description of useful synthetic and biorational insecticides, which highlights environmentally-friendlyprocesses;themodeofaction,emphasizingselectivity towards targeted species and environmental effects (e.g. toxicity, bioaccumu- lation and metabolism and a comparison with classical insecticides); as well as human and environmental risk assessments. Furthermore, formulation, dispersal and persistence in the environment are covered as key aspects in developing greener agrochemicals. Therearenumerousinsectspeciesconsideredtobepestswhichcausehealth problems in humans, cattle and crops, and even affect some human construc- tions.Manyinsectsareknowntoactasvectorsinspreadingimportantdiseases suchasmalaria,dengueortyphus,whichcontinuetoberesponsibleforalarge number of deaths. Moreover, the crops devoted to human and cattle feeding RSCGreenChemistryNo.11 GreenTrendsinInsectControl EditedbyO´ scarLo´pezandJose´ G.Ferna´ndez-Bolan˜os rRoyalSocietyofChemistry2011 PublishedbytheRoyalSocietyofChemistry,www.rsc.org v vi Preface sufferfromimportantlossesinproductivityeveryseasonbecauseofinsectpests acting on them. Thecontrolofsuchpestshasbeenanarduoustaskthatcanbetracedbackto the establishment of the first known civilizations, with numerous techniques and approaches being employed over the centuries. Historically,thefirstattemptstofightnon-beneficialinsectsincludedtheuse ofnaturalsources,eithermineralsorbotanicalextracts,whichbecamethefirst availablechemicalsubstancesagainstinsects.Afterthat,anarsenalofsynthetic derivatives started to be commercially available in what seemed to be a chemicalpanaceaforcontrollingpests.Itbecameevidentquitesoon,however, that most of the compounds successfully applied to crops, cattle and even humans exerted severe effects on the environment. Many of the original chemicals, both natural and synthetic, were initially used indiscriminately, and proved to be highly toxic against living organ- isms, some of them acting indiscriminately on beneficial insects and other animals. Many other insecticides were found to be highly persistent in the environment, as a result of their slow environmental degradation and were bioaccumulated through the trophic chain. Acute toxicological and long- term effects included teratogenic damage, impairment of the central nervous system and malfunctioning of numerous biological processes, among others. Humanity slowly started to be conscious of the necessity of replacing the classical approaches for insect control with ‘‘greener’’ substitutes, with an increased selectivity and a reduced toxicity, as a way of minimising environ- mental impacts. Furthermore, a deeper knowledge of insect physiology has allowed the discovery of targets to which more selective insecticides can be aimed (e.g. sodium channel, chloride channel, acetylcholinesterase, nicotinic acetylcholine receptors, moulting processes, etc.). The first chapter of this book (S. Manguin et al.) is devoted to a general introductiontoentomology,withaspecialemphasisonthoseinsectsthatactas vectorsindiseasescausedbymicrobialpathogens.Thischaptercoversthekey biologicalaspectsofinsectvectors,suchastheirmorphology,habitats,feeding andreproduction.Themaininsectsactingasvectorofdiseasescoveredinthis sectionare:mosquitoes,bitingmidges,flies,fleasandlicewhichareresponsible for spreading severe diseases such as malaria, typhus, lymphatic filariasis, dengue, hemorrhagic fevers and certain encephalitis. The methods by which insects spread infection and the most efficient strategies for fighting against them are widely covered in Chapter 1. The information presented allows for a logical understanding of the mode of action of insecticides, for the design of novel, more efficient compounds. Thesecondchapter(O´ .Lo´pezetal.)providesahistoricalreviewofclassical insecticides,asexamplesofnon-greenagrochemicalsthatmustbereplacedand their use revised. The chapter is divided into two main sections In the first section, the approaches used for insect control before the development of synthetic insecticides are covered. The use of non-rational insecticides, developed from mainly mineral sources (e.g. sulfur, arsenicals, copper and boron derivatives) and, in most cases, lacking specificity is widely reviewed. Preface vii The second part of the chapter is focused on the three main families of synthetic insecticides that have dominated the agrochemical sector from the 1940s to today: organochlorine, organophosphorus and carbamate insecticides. The high efficiency and economic viability of such compounds allowed an indiscriminate use on crops, households and cattle. Throughout this chapter, however, it is strongly emphasized that many of these insecticides are bioaccumulated and can provoke severe toxicological effects in mammals, fish and beneficial insects, such as bees. The restric- tions and bans exerted by highly recognized organizations (such as the US EPA, the European Union Committees and the World Health Organization) for the reduction and even the elimination of the use of such insecticides are also discussed. The rest of this book is devoted to the different approaches for over- coming the adverse effects exerted by the classical insecticides. In this context, the third chapter (Schleier and Peterson) focuses on pyrethroids, a family of insecticides which emerged in the 1970s, inspired by natural pyrethrins (botanical extracts from the Chrysanthemum genus) but lacking their intrinsic photolability. Pyrethroids possess a series of features which have been shown to be greener than the precedent organochlorine, organophosphorous and carbamate insecticides; although pyrethroids are lipophilic molecules, they do not undergo biomagnification and exert no toxic effect on mammals. A critical overview of these compounds is covered, in which they are compared with the parent pyrethrins and clas- sical synthetic insecticides, in terms of toxicity, environmental stability and future expectations. Also inspired by botanical extracts, the neonicotinoids (Chapter 4, Nauen andJeschke)arearelativelynewfamilyofinsecticidesdevelopedinthe1990s. With a surprisingly fast growing market, the development of neonicotinoids has allowed for the controlofsome of the mostdestructive crop insectpests. Inthissection,thedifferentneonicotinoidgenerations,theirstrongspecificity against insect pests and their low mammal toxicity are discussed. The numerous advantages of this group of agrochemicals are reported, and they are proposed as being one of the most promising insecticides in the near future. Chapters 5 (Dripps et al.) and 6 (Gomez et al.) describe work in which DowAgrochemicalshasbeeninvolvedoverthelastfewyears.Thefirstofthese chapters is devoted to spinosyns, macrocyclic lactones resulting from the metabolism of the soil-dwelling bacteria of the Saccharopolyspora species, which were discovered in the late 1980s and firstly marketed in the 1990s. The authors highlight the green character of this kind of insecticide, not only in terms of the production process (fermentation or semi-synthesis), but also in terms of its environmental behaviour with regard to bioaccumulation and selectivity. Spinosad and spinetoram insecticides received the Presidential Green Chemistry Challenge Award in 1999 and 2008, respectively, and when spinosad received its crop registration in 1997, it was among one of the first insecticidestobeconsidered‘‘reduced-risk’’bytheUSEPA.Theauthorsgivea viii Preface detaileddescriptionofthemodeofaction,andQSARandbiologicalstudiesin both targeted and not-targeted species. An exampleof chemicals aimed atthe moulting process ofinsects,and thus atinsectgrowthanddevelopment,isthebisacylhydrazines,whicharereviewed in Chapter 6. The bisacylhydrazines are a non-steroidal family of Insect Growth Regulators (IGRs), for whose initial development Rohm & Haas was awarded the US EPA’s Presidential Green Chemistry Challenge Award in 1998.Structuralstudies,thedesignofnewexamples,environmentaleffectsand formulations are covered in this chapter. In Chapter 7 (Isman and Paluch) the use of botanical extracts as insec- ticides is described. Although, when compared to some other families of agrochemicals, the market of botanical insecticides is much more limited (approximately 1% of total market sales), compounds such as terpenes (from essential oils), or azadirachtin (from neem extracts), deserve attention because of their beneficial biological properties. Plants provide an arsenal of compounds which exert a variety of different insecticidal modes of action: from direct toxicity to insects, to inhibitory properties on growth, devel- opment, reproduction and feeding, as well as repellent activities. The chances of developing and marketing new botanical insecticides are also covered. Besides conventional insecticides (based on the use of natural or synthetic compounds), the use of living systems (e.g. viruses, bacteria, fungi, insect predatorsandengineered-plants)ashighlyselectiveinsectcontrolmechanisms is included in Chapter 8 (Sobero´n et al.). The mode of action, specificity, environmentalriskassessmentsandapplicationindicationsarewidelycovered in this chapter, with a particular emphasis on the most widely used bioinsec- ticides, the endotoxins produced by the bacteria Bacillus thuringiensis. In order to obtain more efficient insecticides from microbial sources, the use of genetically-modified organisms is also reviewed. Finally, the current philosophy in the agrochemical sector of the Integrated Pest Management programmes (IPM) is introduced in Chapter 9 (Castle and Prabhaker). IPMs attempt to reduce the use of synthetic pesticides while keeping pest populations to an acceptable level. The authors claim that a change in agricultural policies is needed for increasing crop production to the rate required while competing with predatory pests. They suggest that key aspectsinpestcontrolwhichareusuallydisregardedincludetheintensification of crops, the appropriate selection of plant species and the appropriate use of fertilizers. The main tactics of defence against pests from a green perspective are also reviewed: the combination of bioengineered crops (e.g. producing thebacterialendotoxinsdescribedinChapter8);anincreaseoftheplanttypes in cropping systems; semiochemicals (e.g. repellents, antifeedants, sex pher- omones, etc., usually in baits); and insect growth regulators. The authors describe how the development of more ecological crops would help reduce insect populations and at the same time our dependence on synthetic insecticides. Preface ix Finally, we would like to express our gratitude to Dr. Manguin, Schleier, Nauen, Dripps, Go´mez, Murray, Sobero´n and Castle, together with their co-workers, firstly for their valuable contributions and also for their con- structive discussions and suggestions for this book. O´ scar Lo´pez and Jose´ G. Ferna´ndez-Bolan˜os Seville

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This book presents the current approaches for insect pest control as a "green" alternative to classical and more toxaic agrochemicals. An overview of the recent advances in insecticide chemistry is also included, which will be of interest to a vast group of researchers - agrochemists, biochemists, c
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