ENCYCLOPEDIA OF AGROCHEMICALS VOLUME 1 ENCYCLOPEDIA OF AGROCHEMICALS Editor-in-Chief EditorialStaff JackR.Plimmer Vice-President,STMBooks:JanetBailey ExecutiveEditor:JacquelineI.Kroschwitz Director,BookProductionandManufacturing:Camille AssociateEditor P.Carter DerekW.Gammon CaliforniaEPA ManagingEditor:ShirleyThomas PublishingTechnologyAssociateManager,Books: DavidBlount AssociateEditor IllustrationManager:DeanGonzalez NancyR.Ragsdale AgriculturalResearchService,USDA EditorialAssistant:AudreyRoker ENCYCLOPEDIA OF AGROCHEMICALS VOLUME 1 Jack R. Plimmer Derek W. Gammon Nancy N. Ragsdale TheEncyclopediaofAgrochemicalsisavailableOnlineat www.mrw.interscience.wiley.com/eoa A John Wiley & Sons, Inc., Publication Copyright2003byJohnWiley&Sons,Inc.Allrightsreserved. PublishedbyJohnWiley&Sons,Inc.,Hoboken,NewJersey. PublishedsimultaneouslyinCanada. Nopartofthispublicationmaybereproduced,storedinaretrievalsystemortransmittedinanyformorbyanymeans,electronic, mechanical,photocopying,recording,scanning,orotherwise,exceptaspermittedunderSection107or108ofthe1976UnitedStates CopyrightAct,withouteitherthepriorwrittenpermissionofthePublisher,orauthorizationthroughpaymentoftheappropriate per-copyfeetotheCopyrightClearanceCenter,Inc.,222RosewoodDrive,Danvers,MA01923,978-750-8400,fax978-750-4470,oron thewebatwww.copyright.com.RequeststothePublisherforpermissionshouldbeaddressedtothePermissionsDepartment,John Wiley&Sons,Inc.,111RiverStreet,Hoboken,NJ07030,(201)748-6011,fax(201)748-6008,e-mail:[email protected]. LimitofLiability/DisclaimerofWarranty:Whilethepublisherandauthorhaveusedtheirbesteffortsinpreparingthisbook,theymake norepresentationsorwarrantieswithrespecttotheaccuracyorcompletenessofthecontentsofthisbookandspecificallydisclaimany impliedwarrantiesofmerchantabilityorfitnessforaparticularpurpose.Nowarrantymaybecreatedorextendedbysales representativesorwrittensalesmaterials.Theadviceandstrategiescontainedhereinmaynotbesuitableforyoursituation.Youshould consultwithaprofessionalwhereappropriate.Neitherthepublishernorauthorshallbeliableforanylossofprofitoranyother commercialdamages,includingbutnotlimitedtospecial,incidental,consequential,orotherdamages. ForgeneralinformationonourotherproductsandservicespleasecontactourCustomerCareDepartmentwithintheU.S.at 877-762-2974,outsidetheU.S.at317-572-3993orfax317-572-4002. Wileyalsopublishesitsbooksinavarietyofelectronicformats.Somecontentthatappearsinprint,however,maynotbeavailablein electronicformat. LibraryofCongressCataloginginPublicationData: ISBN0-471-19363-1 Encyclopediaofagrochemicals/JackR.Plimmer,editor-in-chief. p.cm. ISBN0-471-19363-1(cloth) 1.Agriculturalchemicals—Encyclopedias.I.Plimmer,JackR.,1927- S584.4.E532002 631.8(cid:1)03—dc21 2002027418 PrintedintheUnitedStatesofAmerica 10987654321 PREFACE The Encyclopedia of Agrochemicals covers chemical Council Committee on the Future Role of Pesticides in technology relating to pesticides, fertilizers, and other USAgriculturewhichconcludedthat‘‘chemicalpesticides chemicals germane to this topic. Because the scope will continue to play a role in pest management in the of this field has broadened considerably with deeper foreseeable future, in part because the environmental understanding of the environmental implications of compatibilityofproductsisincreasing—particularlywith chemicaluseanditsecologicalconsequences,theseaspects genes that protect crops, chemicals with new modes of have been included. Such knowledge has stimulated action, and non pesticide management techniques’’ (2). greater regulatory activity and increased the need AlthoughthepesticidemarkethasleveledoffinN.America for toxicological information, which we have included. andEurope,growthintheremainderoftheworldreflects However, manufacturing technology has been excluded thecontinueddemand.China,inparticular,hasincreased fromtheEncyclopedia.TheEncyclopediaisacompilation itsproductionofpesticidechemicalsandproductionofthe of many specially commissioned original articles. It also active ingredients of pesticides grew from 395 thousand includes definitions: The work is intended to serve metric tons in 1997 to 696 thousand metric tons in 2001 principally as a source of chemical information but (3).Thedegreeofsophisticationassociatedwithpesticide toxicology, metabolism, biotechnology, regulatory and useinEuropeandN.Americamustbematchedinthelesser environmentalaspectshavebeenincluded. developedcountriesbyincreasededucationandtrainingif The widespread use of synthetic pesticides began thefullbenefitsofthistechnologyaretoberealized. approximately50yearsagoandwehaveincludedarticles Thepreparationofthisworkreliedonthecooperation on classes of compounds which, although no longer of experts world wide. We would like to thank our many contributors who have devoted time to the preparation in use, have provided experience of the environmental of articles. This has been a particularly difficult time implications of the use of xenobiotics. Moreover in many for those who work in industrial research. During its cases, especially for some organochlorine insecticides, preparation there were many changes in industry that their persistence combined with widespread use has led resulted in consolidation of programs and redirection of tositesofcontaminatedlandandwater,continuingtothe research effort. Thanks are due to colleagues in industry present. However, it should also be borne in mind that who have prepared manuscripts as well as coping with many of these insecticides have played a major role in organizational changes and shifts in research emphasis. restrictingdiseasessuchasmalaria,yellowfever,dengue Our contributors in government and academia have also fever, plague, Chargas’ disease, African river blindness, felt the general pressures of reduced support for science. typhus, sleeping sickness etc. Such success could not We recognized that gaps in coverage were inevitable have been achieved had these agents not been initially because the exigencies of publication did not always developedasagrochemicals. harmonize with the schedules of the many experts who TheyearsimmediatelyfollowingthecloseofWorldWar wereconsultedduringthepreparationoftheEncyclopedia. IIwitnessed almostexplosive growth inthe development We acknowledge the help and advice of many and application of synthetic organic chemicals to the colleagues. Among them Dr. Terry Roberts of JSCN control of insect pests, plant-disease causing organisms, Internationalwasinvolvedintheconceptualandplanning andweeds.Thesubsequentchallengestopestmanagement stages, Dr. Steve Duke provided guidance and help with systems that relied predominantly on chemical control herbicideentries,Dr.IstvanUjvaryassistedinwritingor arose both from environmental concerns and from the commissioningarticles. developmentofresistanceamongpestspecies.Alternative Manydefinitionshavebeenincluded.Whereindicated strategies were needed and these developments were in the text these have been published by IUPAC in accompaniedbytheestablishmentofregulatoryagencies the IUPAC Report on Pesticides (36), Glossary of Terms whose major goal was to mitigate the harmful effects relating to Pesticides, Pure and Appl. Chem. 68:N06, pp. of pesticide use, whether real or perceived. Industry 1167–1193(1996). responded to this evolutionary process by seeking to (1) A.L.Aspelinand A.H. Grube,Pesticides Industry developmoleculesthatmetcriteriaofimprovedhumanand SalesandUsage:1996and1997MarketEstimates, environmental safety. In recent years biotechnology has Biological and Economic Analysis Division, Office providedsolutionsbymodifyingcropssothattheywould of Pesticide Programs, Office of Prevention, Pes- expressinsecticidaltoxinsorresisttheactionofherbicides ticides and Toxic Substances, U.S. Environmental thathadmettheapprovalofregulatoryauthorities. ProtectionAgency,Washington,DC20460,Novem- Thesechangeshavebeenreflectedinthemarketplace. ber1999,733-R-99-001. The acreage treated with pesticides remains high but amountsappliedhavedecreasedaschemicalsbecomemore (2) Committee on the Future Role of Pesticides in efficacious and application becomes more efficient. The US Agriculture, ‘‘The Future Role of Pesticides in USAgriculture’’,NationalResearchCouncil,Board pesticide market continues to flourish and in the United on Agriculture and Natural Resources, National States where over 1.2 billion pounds of active ingredient AcademyPress,Washington,D.C.p.2(2000). were used in 1997, pesticides account for about 4.5% of total farm production costs (1). The situation in the (3) ChemicalandEngineeringNews,80,82(2002). US was the subject of a report by a National Research JackR.Plimmer v CONTRIBUTORS Basil Acock, USDA-ARS, Beltsville, Maryland, USDA-ARS Pesticide Heinrich Dittmar, BASF Aktiengesellschaft, Ludwigshafen, Germany, PropertiesDatabase PlantNutrition ThomasAddiscott,RothamstedExperimentalStation,Harpenden,Herts, KelleyJ.Donham,,AgriculturalHygiene UnitedKingdom,NitrateinGroundwater ManfredDrach,BASFAktiengesellschaft,Limburgerhof,Germany,Plant David B. Alexander, University of Portland, Portland, Oregon, Soil Nutrition Bacteria Stephen O. Duke, USDA, ARS, Natural Products Utilization Res. RezaAsiaie,RocheMolecularSystems,Somerville,NewJersey,Capillary Unit, University, Mississippi, Herbicides, Biotechnology for Control Electrophoresis of Weeds; Herbicides, Carotenoid Biosynthesis Inhibitors; Herbicides, MichaelL.Avery,NationalWildlifeResearchCenter,Gainesville,Florida, Cinmethylin;Herbicides,ProtoporphyrinogenOxidaseInhibitors AvianRepellents Estrella Duque, Estacio´n Experimental del Zaid´ın, Granada, Spain, Joseph E. Bailey, Arlington, Virginia, Food Quality Protection Act of BiodegradationofXenobioticsbyEngineeredMicrobes 1996 CliveEdwards,TheOhioStateUniversity,Columbus,Ohio,Microcosms DavidL.Balkwill,FloridaStateUniversity,Tallahassee,Florida,Sub- Janice W. Edwards, MonsantoCompany, St.Louis,Missouri,Genetic surfaceMicrobialCommunities:DiversityofCulturableMicroorganisms Engineering,Plants Jerry J. Baron, Rutgers, The State University of New Jersey, North Brunswick,NewJersey,MinorUsePesticides,Registration Thomas Egli, Swiss Federal Institute for Environmental Science and Technology,Du¨bendorf,Switzerland,MetabolismofMixturesofOrganic Anton Baudoin, Virginia Polytechnic Institute and State University, Pollutants Blacksburg,Virginia,ChemotherapyofPlantDiseases Donald H. Beermann, University of Nebraska, Lincoln, Nebraska, MonicaElliott,MontanaStateUniversity,Bozeman,Montana,PCR GrowthRegulators,Animals Manuel Espinosa-Urbel, Estacio´n Experimental del Zaid´ın, Granada, G. Knauf-Beiter, Syngenta Crop Protection AG, Basel, Switzerland, Spain,BiodegradationofXenobioticsbyEngineeredMicrobes Fungicides,Phenylpyrroles Abraham Esteve-Nu´n˜ez,Estacio´nExperimental del Zaid´ın, Granada, RaviG.Bhat,UniversityofCalifornia,Davis,California,Tillage Spain,BiodegradationofXenobioticsbyEngineeredMicrobes EulaBingham, RegulationsandGuidelinesintheWorkplace MorifusaEto,Fukuoka,Japan,OrganophosphorusInsecticides Robert S. Boethling, Office of Pollution Prevention and Toxics, U.S. AllanFelsot,WashingtonStateUniversityTri-Cities,Richland,Washing- Environmental Protection Agency, Washington, District of Columbia, ton,LD50 ChemicalPropertiesEstimation Esther Forga´cs, Hungarian Academy of Sciences,Budapest, Hungary, Douglas Boyette, USDA, ARS, Southern Weed Science Res. Unit, Chromatography,HPLC;Chromatography,TLC Stoneville,Mississippi,Herbicides,BiotechnologyforControlofWeeds Peter Frenzel, Max-Planck-Institut fu¨r Terrestrische Mikrobiologie, Walter Bra¨ndlein, BASF Aktiengesellschaft, Ludwigshafen, Germany, Marburg,Germany,FloodedSoils PlantNutrition L. J. Shane Friesen, University of Guelph, Guelph, Ontario, Canada, KeithJ.Brent,Bristol,England,Fungicides,AnOverview Herbicides,PlantHormoneMimics—Auxins Richard Bromilow, Rothamsted, Harpenden, Herts, United Kingdom, DerekW.Gammon,CaliforniaEPA,Sacramento,California,Herbicides: SoilPersistence InhibitorsofGlutamineSynthetase;Insecticides,Organochlorines Matthew W. Brooks, AG-CHEM Consulting, LLC, Clifton, Virginia, B. Clifford Gerwick, Dow Agrosciences,Indianapolis, Indiana, Herbi- StandardEvaluationProcedures cides,IdentificationofBiologicallyActiveMaterials ThomasM.Brown,Gene´CTAr.com,LLC,Clemson,SouthCarolina,Insect ResistancetoInsecticides Ulrich Gisi, Syngenta Crop Protection, Basel, Switzerland, Fungicides, Phenylamides/Acycalanines CharlesT.Bryson,USDA-ARS,Stoneville,Mississippi,WeedSpecies Alan Buckle, (formerly Novartis Crop Protection, Basel), Hergiswill, David J. Glass, D. Glass Associates, Inc., Needham, Massachusetts, Switzerland,Rodenticides RegulationoftheCommercialUseofMicroorganisms CaroleeT.Bull,USDA–ARS,Salinas,California,BiologicalControlof DayanB.Goodenowe,YolBolsumInc.,Rycroft,Alberta,Canada,LC/MS, PlantDiseases PesticideResidueAnalysis H. Buschhaus,AventisCropScienceGmbH, RegulatoryAffairsEurope, L.FayeGrimsley, RegulationsandGuidelinesintheWorkplace FrankfurtamMain,Germany,Fungicides,Carbamates ReinholdGutser,Lehrstuhlfu¨rPflanzenerna¨hrung,TechnischeUniver- AntonioCaballero,Estacio´nExperimentaldelZaid´ın,Granada,Spain, sita¨tMu¨nchen-Weihenstephan,Freising,Germany,PlantNutrition BiodegradationofXenobioticsbyEngineeredMicrobes ReinhardtHa¨hndel,BASFAktiengesellschaft,Limburgerhof,Germany, Thomas M. Cahill, Canadian Environmental Modelling Centre, Trent PlantNutrition University,Peterborough,Ontario,Canada,FugacityModeling Christopher Hall, University of Guelph, Guelph, Ontario, Canada, C. Camara, University Complutense of Madrid, Madrid, Spain, Herbicides,PlantHormoneMimics—Auxins Ethylenebisthiocarbamates(Analysis) RaymondHammerschmidt,MichiganStateUniversity,EastLansing, D.A.Carlson,UniversityofFlorida,Gainesville,Florida,Repellents Michigan,Juglone;PreexistingDefenseChemicals DavidJ.Chitwood,USDA-ARS,Beltsville,Maryland,Nematicides Kriton Hatzios, Virginia Polytechnic Institute, Blacksburg, Virginia, J.MarshallClark,UniversityofMassachusetts,Amherst,Massachusetts, Herbicides,PlantResistancetoHerbicides TurfgrassPesticides:ManagementandEnvironmentalIssues MatthewJ.Henry,DowAgroSciences,Indianapolis,Indiana,Fungicides, RalfConrad,Max-Planck-Institutfu¨rTerrestrischeMikrobiologie,Mar- Quinoxyfen burg,Germany,FloodedSoils JoanM.Henson,MontanaStateUniversity,Bozeman,Montana,PCR Tibor Cserha´ti, Hungarian Academy of Sciences, Budapest, Hungary, Albert E.Herner,USDA-ARS,Beltsville,Maryland,USDA-ARSPesti- Chromatography,HPLC;Chromatography,TLC cidePropertiesDatabase Vilmos Czikkely, BASF Aktiengesellschaft, Ludwigshafen, Germany, PlantNutrition Abe Hiroshi, Tokyo Universityof Agriculture,Tokyo, Japan, Brassino- steroids Franck E. Dayan, USDA-ARS Natural Products Utilization Research Unit, University, Mississippi, Herbicides, Carotenoid Biosynthesis Robert E. Hoagland, USDA, ARS, SWSRU, Stoneville, Mississippi, Inhibitors; Herbicides, Cinmethylin; Herbicides, Protoporphyrinogen MetabolismofHerbicides OxidaseInhibitors Derek W. Hollomon, University of Bristol, Bristol, United Kingdom, A.J.Dewar,ArthurDewarAssociates,UnitedKingdom,EURegistration Fungicides, 2-Aminopyrimidines; Fungicides, Fungal Resistance to Directive ChemicalControls vii viii CONTRIBUTORS Robert E. Holm, Rutgers, The State University of New Jersey, North NeilMackay,CambridgeEnvironmentalAssessments,Boxworth,United Brunswick,NewJersey,MinorUsePesticides,Registration Kingdom,GroundwaterModelingTools WilliamR.Horwath,UniversityofCalifornia,Davis,California,Biomass: EugeneL.Madsen,CornellUniversity,Ithaca,NewYork,Biodegradabil- SoilMicrobialBiomass ity:Assessment Philip H. Howard, Syracuse Research Corporation, Environmental VolkerMagnus,InstitutRudjerBosˇkovic´,Zagreb,Croatia,Auxins,Indole Science Center, North Syracuse, New York, Chemical Properties Auxins Estimation Ashok Kumar Malik, G.N.D. University, Amritsar, Punjab, India, HideoIshii,NationalInstituteforAgro-EnvironmentalSciences,Tsukuba, Ethylenebisthiocarbamates(Analysis) Ibaraki,Japan,Fungicides,Tubulin-BindingCompounds Otis C. Maloy, Washington State University, Pullman, Washington, NicholasJarvis,SwedishUniversityofAgriculturalSciences,Uppsala, ChemotherapyofPlantDiseases;Disinfection;Disinfestation Sweden,MacroporeFlowModels;MacroporeandPreferentialFlow GeorgeM.Markle,Rutgers,TheStateUniversityofNewJersey,North Paul Jepson, Oregon State University, Corvallis, Oregon, Natural Brunswick,NewJersey,MinorUsePesticides,Registration Enemies AlbertusMartijn,CIPAC,Ruurlo,TheNetherlands,CIPAC PhilipJ.Jewess,IACR–Rothamsted,Harpenden,Hertfordshire,United Konrad Mengel, Justus-Liebig-Universita¨t Giessen, Institute for Plant Kingdom,AcetylcholineReceptors;Acetylcholinesterase;ChitinBiosyn- Nutrition,Giessen,Germany,PlantNutrition thesisInhibitors JuliusJ.Menn,Highland,Maryland,Biopesticides MadanM.Joshi,DuPontAgriculturalProducts,Wilmington,Delaware, RobertL.Metcalf,UniversityofIllinois,Urbana,Illinois,GeneticControl Fungicides,Cymoxanil ofInsects ShinzoKagabu,GifuUniversity,Gifu,Japan,Insecticides,Imidacloprid William M. Meylan, Syracuse Research Corporation, Environmental PhilipC.Kearney,USDA-ARS,Beltsville,Maryland,SoilChemistryof Science Center, North Syracuse, New York, Chemical Properties Pesticides Estimation IvanR.Kennedy,UniversityofSydney,Sydney,Australia,Immunoassays Carmen Micha´n, Estacio´n Experimental del Zaid´ın, Granada, Spain, AllenKerr,UniversityofAdelaide,Adelaide,Australia,Agrocin84 BiodegradationofXenobioticsbyEngineeredMicrobes SushilK.Khetan,NewDelhi,India,StorageStability CarolJ.Miller,WayneStateUniversity,Detroit,Michigan,Groundwater Ganesh M. Kishore, Monsanto Company, St. Louis, Missouri, Genetic Monitoring Engineering,Plants Pierre Mineau, National Wildlife Research Centre, Canadian Wildlife KimikoKlein,CaliforniaEnvironmentalProtectionAgency,Sacramento, Service,Ottawa,Ontario,Canada,AvianSpecies California,Remediation Amitava Mitra, University of Nebraska, Lincoln, Nebraska, Genetic William A. Kleschick, Dow AgroSciences LLC, Indianapolis, Indiana, Engineering CombinatorialChemistryasAppliedtoTheDiscoveryofAgrochemicals William T. Molin, USDA-ARS, Stoneville, Mississippi, Herbicides, Gu¨nterKluge,Bundesministeriumfu¨rErna¨hrung,Landwirtschaftund PyridineCarboxylate Forsten,Bonn,Germany,PlantNutrition Thomas B. Moorman, USDA Agricultural Research Service, National BiserkaKojic´-Prodic´,InstitutRudjerBosˇkovic´,Zagreb,Croatia,Auxins, SoilTilthLaboratory,Ames,Iowa,SoilDistributionofMicroorganisms IndoleAuxins TakayukiMotoyama,RIKEN(TheInstituteofPhysicalandChemical WolframKo¨ller,CornellUniversity,Ithaca,NewYork,Fungicides,Sterol Research),Wako,Japan,Fungicides,MelaninBiosynthesisInhibitors BiosynthesisInhibitors Hermann Mu¨hlfeld, Formerly Chemische Fabrik Kalk GmbH, Ko¨ln, William C. Koskinen, USDA-Agricultural Research Service, Soil Germany,PlantNutrition ChemistryofPesticides Franz Mu¨ller, (formerly Novartis Crop Protection, Basel), Hergiswill, SagarV.Krupa,UniversityofMinnesota,St.Paul,Minnesota,Ethylene Switzerland,GeneticControlofInsects;Rodenticides AlexanderJ. Krynitsky,U.S.EnvironmentalProtectionAgency,Fort DavidD.Myrold,OregonStateUniversity,Corvallis,Oregon,Nitrogen Meade,Maryland,LC/MS,PesticideResidueAnalysis CycleinSoil Friedrich Kuhlmann, Institut fu¨r Landwirtschaftliche Betriebslehre, WilliamE.Newton,VirginiaPolytechnicInstituteandStateUniversity, Giessen,Germany,PlantNutrition Blacksburg,Virginia,NitrogenFixation PaulJ.Kuhn,SyngentaCropProtection,VeroBeach,Florida,Fungicides, Ralph L. Nicholson, Purdue University, West Lafayette, Indiana, InhibitorsofMitochondrialEnergyProduction Phytoalexin Karl-FriedrichKummer,BASFAktiengesellschaft,Limburgerhof,Ger- Titus Niedermaier, Formerly BASF Aktiengesellschaft, Ludwigshafen, many,PlantNutrition Germany,PlantNutrition WalterKunz,SyngentaCropProtectionAG,Basel,Switzerland,Chemical Naoko Nishikawa-Koseki, Tokyo University of Agriculture, Tokyo, ActivatorsofDiseaseResistance Japan,Brassinosteroids NorioKurihara,Kyoto,Japan,ChiralityandChiralPesticides Patrick Noland, ABC Laboratories Europe, Coleraine, Ireland, Solid LeslieC.Lane,UniversityofNebraska,Lincoln,Nebraska,Electrophore- PhaseExtraction sis Walter Oettmeier, Ruhr—Universitaet Bochum, Bochum, Germany, BerndLennartz,UniversityRostock,Rostock,Germany,Soil,Movement Herbicides,InhibitorsofPhotosynthesisatPhotosystemII ofPesticidesIn Offiah O. Offiah, Maryland Department of Agriculture, Annapolis, PierreLeroux,InstitutNationaldelaRechercheAgronomique,Versailles, Maryland,Analysis—InstrumentationandTechniques France,Fungicides,Anilopyrimidines;Fungicides,Dicarboximides Anna Oliva, Second University of Naples, Caserta, Italy, Herbicides, Gavin B. Lewis, JSC International Ltd., Harrogate, North Yorkshire, BiotechnologyforControlofWeeds UnitedKingdom,NaturalEnemies MichaelO’Malley,UniversityofCalifornia,Davis,California,Epidemi- LeslieC.Lewis,AgriculturalResearchService,USDA,Ankeny,Iowa,and ologyofPesticideExposure IowaStateUniversity,Ames,Iowa,BiologicalControl,Survey MichaelOostendorp,SyngentaCropProtectionAG,Basel,Switzerland, Morton Lippmann, Pathways and Measuring Exposure to Toxic ChemicalActivatorsofDiseaseResistance Substances Ann B. Orth, FMC Corporation, Princeton, New Jersey, Fungicides, David A. Lipson, San Diego State University, San Diego, California, InhibitorsofMitochondrialEnergyProduction KineticsofMicrobialProcessesandPopulationGrowth CraigOsteen,EconomicResearchService,USDA,Washington,Districtof J. P. Little, Aventis CropScience, Ongar, Essex, United Kingdom, Columbia,EconomicIssuesofUSAgriculturalPesticideUse Herbicides,Inhibiting4-HydroxyphenylpyruvateDioxygenase(HPPD) MerrittPadgitt,EconomicResearchService,USDA,Washington,District JohnLydon,USDA,ARS,SustainableAgriculturalSystemsRes.Unit, ofColumbia,EconomicIssuesofUSAgriculturalPesticideUse Beltsville,Maryland,Herbicides,BiotechnologyforControlofWeeds Ken E. Pallett, Aventis CropScience, Frankfurt am Main, Germany, H.Lyr,Eberswalde,Germany,Fungicides,AromaticHydrocarbons Herbicides, Asulam; Herbicides, Inhibiting 4-Hydroxyphenylpyruvate Donald Mackay, Canadian Environmental Modelling Centre, Trent Dioxygenase(HPPD) University,Peterborough,Ontario,Canada,FugacityModeling La´szlo´Pap,Agro-ChemieLtd.,Budapest,Hungary,Pyrethroids CONTRIBUTORS ix Marshall H. Parker, Dow AgroSciences LLC, Indianapolis, Indiana, Hugo Steinhauser, Formerly Lehrstuhl fu¨r Wirtschaftslehre des, CombinatorialChemistryasAppliedtoTheDiscoveryofAgrochemicals Landbaues,TechnischeUniversita¨tMu¨nchen,Freising,Germany,Plant JuergenPauluhn,BayerAG,Wuppertal,Germany,InhalationToxicity Nutrition Mikael Pell, Swedish University of Agricultural Sciences, Uppsala, Steven J. Stout, BASF Corporation, Princeton, New Jersey, LC/MS, Sweden,ToxicityTestinginSoils PesticideResidueAnalysis WilfriedPestemer,FederalBiologicalResearchCentreofAgricultureand JamesStry,DupontCropProtection,Newark,Delaware,LC/MS,Pesticide Forestry,Berlin,Germany,Bioassays:PhytotoxicitytoSucceedingCrops ResidueAnalysis Ch. Pillonel, Syngenta Crop ProtectionAG, Basel,Switzerland,Fungi- KrishnaV.Subbarao,UniversityofCalifornia,Davis,California,Tillage cides,Phenylpyrroles GeorgeW.Sundin,MichiganStateUniversity,EastLansing,Michigan, JackR.Plimmer,Tampa,Florida,Insecticides,Organochlorines;Her- AntibioticResistance;Antibiotics;Streptomycin;Tetracycline bicides:InhibitorsofGlutamineSynthetase;Herbicides,AnOverview; Susan D. Sutton, Miami University, Oxford, Ohio, Quantification of InsecticidalCarbamates MicrobialBiomass ErnestL.Plummer,FMCCorporation,Princeton,NewJersey,QSAR M.AliTabatabai,IowaStateUniversity,Ames,Iowa,SoilEnzymes WilliamPopendorf, AgriculturalHygiene MichitoTagawa,NissanChemicalInd. Ltd.,Shiraoka,Japan,Fungi- HansPru¨n,FormerlyBASFAktiengesellschaft,Limburgerhof,Germany, cides,Antibiotics PlantNutrition MaxE.Tate,UniversityofAdelaide,Adelaide,Australia,Agrocin84 JosM.Raaijmakers,WageningenUniversity,Wageningen,TheNether- Alan W. Taylor, USDA-ARS, College Park, Maryland, Fertilizers; lands,Rhizosphere VolatilityofPesticides Marı´a-Isabel Ramos-Gonza´lez, Estacio´n Experimental del Zaid´ın, J.RichardM.Thacker,BiologicalSciences,UniversityofPaisley,Paisley, Granada,Spain,BiodegradationofXenobioticsbyEngineeredMicrobes Scotland,PesticideAdjuvants Juan L. Ramos, Estacio´n Experimental del Zaid´ın, Granada, Spain, Lennart Torstensson, Swedish University of Agricultural Sciences, BiodegradationofXenobioticsbyEngineeredMicrobes Uppsala,Sweden,ToxicityTestinginSoils P. T. Reeves, National Registration Authority for Agricultural and MartinE.Trenkel,Eusserthal,Germany,PlantNutrition VeterinaryChemicals,Kingston,Australia,AnimalHealthProducts RonTurco,PurdueUniversity,WestLafayette,Indiana,Biodegradation JonB.Reid, Dibenzo-p-Dioxins:2,3,7,8-Tetrachlorodibenzo-p-Dioxin inSoil WilliamA.Rickelton,CytecCanadaInc.,PhosphineandItsDerivatives James A. Turner, Dow AgroSciences LLC, Indianapolis, Indiana, CombinatorialChemistryasAppliedtoTheDiscoveryofAgrochemicals JoanneG.Romagni,USDA-ARSNaturalProductsUtilizationResearch Unit,University,Mississippi,Herbicides,Cinmethylin B. G. Tweedy, Jamestown, North Carolina, Fungicides, Copper Com- poundsandSulfur ErinN.Rosskopf,USDA–ARS,USHRL,FortPierce,Florida,Biological ControlofWeeds YasuhikoUesugi,Tokyo,Japan,Fungicides,MultisiteInhibitors—Broad SpectrumSurfaceProtectants RobertP.Sabba,USDA-ARS,Fargo,NorthDakota,Herbicides,Cellulose BiosynthesisInhibitors Istva´n Ujva´ry, Hungarian Academy of Sciences, Budapest, Hungary, NaturalProductPesticides;Propesticides HudanSafarpour,AmericanCyanamidCompany,Princeton,NewJersey, Karl-Heinz Ullrich,BASFAktiengesellschaft,Limburgerhof,Germany, Stephen H. Safe, Texas A&M University, College Station, Texas, PlantNutrition ChlorocarbonsandChlorohydrocarbons—ToxicAromatics MarilynUnderwood,CaliforniaDepartmentofHealthServices,Oakland, MitsuruSasaki,KobeUniversity,Kobe-shiHyogo-ken,Japan,Fungicides, California,Remediation OrganophosphorusCompounds DonValentine,Ridgefield,Connecticut,SoilConditioners:Agricultural BrianE.Scheffler,USDA,ARS,NaturalProductsUtilizationRes.Unit, Applications University,Mississippi,Herbicides,BiotechnologyforControlofWeeds Jan Roelof van der Meer, Swiss Federal Institute for Environmental HeinrichW.Scherer,Universita¨tBonn,AgrikulturchemischesInstitut, ScienceandTechnology(EAWAG),Du¨bendorf,Switzerland,Metabolic Bonn,Germany,PlantNutrition PathwaysEvolution StevenK.Schmidt,UniversityofColorado,Boulder,Colorado,Kinetics Laura L. Van Eerd, University of Guelph, Guelph, Ontario, Canada, ofMicrobialProcessesandPopulationGrowth Herbicides,PlantHormoneMimics—Auxins Mark R. Schmitt, Trenton, New Jersey, Fungicides, Inhibitors of Dick Van Elsas, Plant Research International B.V., Wageningen, The MitochondrialEnergyProduction Netherlands, Genetically Modified Microorganisms (GMM) in Soil Ana Segura, Estacio´n Experimental del Zaid´ın, Granada, Spain, Environments BiodegradationofXenobioticsbyEngineeredMicrobes Leo Van Overbeek, Plant Research International B.V., Wageningen, Dale Shaner, USDA-ARS, Colorado State University, Fort Collins, TheNetherlands,GeneticallyModifiedMicroorganisms(GMM)inSoil Colorado,Herbicides,Imidazolinone Environments DanielR.Shelton,USDA-AgriculturalResearchService,SoilChemistry Kevin C. Vaughn, USDA-ARS, Stoneville, Mississippi, Herbicides, ofPesticides PyridineCarboxylate;PhotosystemIEnergyDiverters Malcolm C. Shurtleff, University of Illinois, Urbana–Champaign, AnneK.Vidaver,UniversityofNebraska,Lincoln,Nebraska,Bacteriocins Illinois, Texas A&M University, College Station, Texas, Aflatoxin; RalfVosskamp,BASFAktiengesellschaft,Limburgerhof,Germany,Plant Fumonisins;MycotoxinandMycotoxicoses;Vomitoxin Nutrition JamesJ.Sims,UniversityofCalifornia,Riverside,California,Fungicides, ShuoWang,UniversityofSydney,Sydney,Australia,Immunoassays SoilFumigants MonteR.Weimer,DowAgrosciences,Indianapolis,Indiana,Herbicides, John H. Skerritt, Australian Centre for International Agricultural IdentificationofBiologicallyActiveMaterials Research,Canberra,Australia,Immunoassays Wilfried Werner, Agrikulturchemisches Institut der Universita¨t Bonn, Jeffrey L.Smith,USDA–ARS,WashingtonStateUniversity,Pullman, Bonn,Germany,PlantNutrition Washington,SoilQuality,TheRoleofMicroorganisms RichardWilkins,UniversityofNewcastle,NewcastleuponTyne,United David M. Stark, Monsanto Company, St. Louis, Missouri, Genetic Kingdom,ControlledReleaseFormulationsofPesticides Engineering,Plants M. F. Wilson, Central Science Laboratory, Sand Hutton, York, United J. R. Startin, Central Science Laboratory, Sand Hutton, York, United Kingdom,MALDI Kingdom,MALDI Thomas S. Woods, DuPont Agricultural Enterprise, Wilmington, PaulStaswick,UniversityofNebraska,Lincoln,Nebraska,JasmonicAcid Delaware,PesticideFormulations Theodor Staub, Syngenta Crop Protection AG, Basel, Switzerland, Isamu Yamaguchi, RIKEN (The Institute of Physical and Chemical ChemicalActivatorsofDiseaseResistance Research),Wako,Japan,Fungicides,MelaninBiosynthesisInhibitors; Gu¨nter Steffens, Landwirtschaftliche Untersuchungs- und Forschung- Fungicides,Antibiotics sanstalt,Oldenburg,Germany,PlantNutrition HendrikYpema,BASFCorporation,ResearchTrianglePark,NorthCar- A. Steinemann, Syngenta Crop Protection AG, Basel, Switzerland, olina, Fungicides, Dimethomorph; Fungicides, Ferimzone; Fungicides, Fungicides,Phenylpyrroles Hymexazol x CONTRIBUTORS BrianGeraldYoung,SouthernIllinoisUniversity,Carbondale,Illinois, Hugo Ziegler, Pentapharm, Basel, Switzerland, Fungicides, Pheny- HerbicideAdjuvants lamides/Acycalanines RobertM.Zablotowicz,USDA,ARS,SWSRU,Stoneville,Mississippi, Stephen H. Zinder, Cornell University, Ithaca, New York, Reductive MetabolismofHerbicides Dehalogenation