Modern Crop Protection Compounds (3 Volume set)

1348 Pages·2007·27.85 MB·English

by  Wolfgang Krämer

ModernCropProtection
Compounds
Editedby
WolfgangKra¨merand
UlrichSchirmer
ModernCropProtectionCompounds. EditedbyW.Kra¨merandU.Schirmer
Copyright82007WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim
ISBN:978-3-527-31496-6

Modern Crop Protection Compounds
Edited by
Wolfgang Kra¨mer and Ulrich Schirmer
Volumes 1 - 3
TheEditors 9 AllbookspublishedbyWiley-VCHare
carefullyproduced.Nevertheless,authors,
Dr.WolfgangKra¨mer editors,andpublisherdonotwarrantthe
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Germany Readersareadvisedtokeepinmindthat
statements,data,illustrations,procedural
Dr.UlrichSchirmer detailsorotheritemsmayinadvertentlybe
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82007WILEY-VCHVerlagGmbH&Co.
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ISBN 978-3-527-31496-6
V
Contents
Volume1
Preface XIX
ListofContributors XXI
I Herbicides 1
Overview 3
WolfgangKra¨merandUlrichSchirmer
1 HRACClassificationofHerbicidesandResistanceDevelopment 5
HubertMenneandHelmutKo¨cher
1.1 Introduction 5
1.2 HRACClassificationSystemofHerbicides 5
1.3 HerbicideResistance 9
1.3.1 BiochemistryofHerbicideResistance 13
1.3.1.1 Target-siteResistance 13
1.3.1.2 Nontarget-siteResistancebyEnhancedMetabolicDetoxification 19
1.3.1.3 Nontarget-siteResistancebyAlteredHerbicideDistribution 22
1.3.1.4 MultipleResistance 23
References 24
2 AcetohydroxyacidSynthaseInhibitors(AHAS/ALS) 27
2.1 BiochemistryoftheTargetandResistance 27
MarkE.Thompson
2.1.1 AcetohydroxyacidSynthase(AHAS) 27
2.1.2 HerbicidesthatTargetAHAS 32
2.1.3 BindingSiteforAHAS-inhibitingHerbicides 33
2.1.4 MolecularBasisforResistancetoAHASInhibitors 38
2.1.5 ResistancetoAHAS-inhibitingHerbicidesinWeeds 40
References 42
ModernCropProtectionCompounds. EditedbyW.Kra¨merandU.Schirmer
Copyright82007WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim
ISBN:978-3-527-31496-6
VI Contents
2.2 NewerSulfonylureas 45
OswaldOrt
2.2.1 Introduction 45
2.2.1.1 HistoryandDevelopment 48
2.2.1.2 Synthesis 51
2.2.2 AgriculturalUtility 52
2.2.2.1 Cereals 52
2.2.2.2 Rice 63
2.2.2.3 Maize 70
2.2.2.4 OtherCrops 73
2.2.3 MetabolicFateandBehaviorintheSoil 76
2.2.4 ConcludingRemarks 77
References 78
2.3 ImidazolinoneHerbicides 82
DaleL.Shaner,MarkStidham,andBijaySingh
2.3.1 Overview 82
2.3.2 HistoryofDiscovery 83
2.3.3 PhysicalChemicalProperties 84
2.3.4 StructuralFeaturesofHerbicidalImidazolinones 85
2.3.5 ModeofActionofImidazolinones 86
2.3.6 Imidazolinone-tolerantCrops 87
2.3.7 CommercialUsesoftheImidazolinoneHerbicides 88
2.3.8 MechanismsofSelectivity 89
2.3.9 Conclusion 91
References 91
2.4 Triazolopyrimidines 93
TimothyC.Johnson,RichardK.Mann,PaulR.Schmitzer,RogerE.Gast,
andGerritJ.deBoer
2.4.1 Introduction 93
2.4.2 N-Triazolo[1,5-c]pyrimidineSulfonanilides 93
2.4.2.1 Synthesis 93
2.4.2.2 Biology 95
2.4.2.3 MechanismofCropSelectivity 96
2.4.2.4 EnvironmentalDegradation,EcotoxandTox 98
2.4.3 N-Triazolo[1,5-c]pyrimidineSulfonamides 99
2.4.3.1 Synthesis 99
2.4.3.2 Biology 100
2.4.3.3 PenoxsulamCropUtility 102
2.4.3.4 PenoxsulamMechanismofCropSelectivity 103
2.4.3.5 PenoxsulamEnvironmentalDegradation,EcotoxandTox 103
Contents VII
2.4.4 N-Triazolo[1,5-a]pyrimidineSulfonamides 104
2.4.4.1 Synthesis 104
2.4.4.2 Biology 104
2.4.4.3 DE-742CropUtility 105
2.4.4.4 DE-742MechanismofCropSelectivity 106
2.4.4.5 DE-742EnvironmentalDegradation,EcotoxandTox 107
2.4.5 OtherSystems 108
2.4.5.1 Synthesis 108
2.4.5.2 Biology 109
2.4.6 Conclusion 112
References 112
2.5 Pyrimidinylcarboxylates 114
FumitakaYoshida,YukioNezu,RyoHanai,andTsutomuShimizu
2.5.1 Introduction 114
2.5.2 DiscoveryofthePyrimidinylcarboxylates 114
2.5.3 Structure–ActivityRelationships 117
2.5.3.1 EffectsofBenzeneRingSubstituentsintheO-Pyrimidinylsalicylic
Acids 117
2.5.3.2 EffectofaBridgeAtominthePyrimidinylsalicylates 118
2.5.3.3 Pyrimidinylglycolates 118
2.5.3.4 CommercializedPCHerbicides 121
2.5.4 ‘‘Pyrithiobac-sodium’’–CottonHerbicide 122
2.5.4.1 Discovery 122
2.5.4.2 Synthesis 123
2.5.4.3 Biology 123
2.5.5 ‘‘Bispyribac-sodium’’–HerbicideinDirect-seededRice 123
2.5.5.1 Discovery 123
2.5.5.2 Synthesis 125
2.5.5.3 Biology 125
2.5.6 ‘‘Pyriminobac-methyl’’–RiceHerbicide 126
2.5.6.1 Discovery 126
2.5.6.2 Synthesis 129
2.5.6.3 Biology 129
2.5.7 ‘‘PyribenzoximandPyriftalid’’–RiceHerbicides 130
2.5.8 ModeofActionofthePCHerbicides 131
2.5.9 ModeofSelectivityofthePCHerbicidesinCrops 132
2.5.10 PC-resistantPlantsandtheirMutatedALSGenes 132
2.5.11 UseoftheMutatedALSGenesforGeneticTransformation
ofPlants 134
2.5.12 UseoftheMutatedALSGenesforResistanceManagement
ofALS-inhibitingHerbicides 135
References 136
VIII Contents
2.6 Sulfonylaminocarbonyl-triazolinones 138
Klaus-HelmutMu¨ller
2.6.1 Introduction 138
2.6.2 DiscoveryoftheActiveIngredients 138
2.6.3 OptimizationoftheLeadStructure 140
2.6.4 Synthesis 143
2.6.4.1 SulfonylComponents 144
2.6.4.2 TriazolinoneSynthesis 145
2.6.5 Biology 147
2.6.6 Conclusion 148
References 148
3 Protoporphyrinogen-IX-oxidaseInhibitors 153
GeorgeTheodoridis
3.1 Introduction 153
3.2 HistoricalDevelopment 154
3.2.1 DiphenylEther 154
3.2.2 PhenylRingAttachedtoHeterocycle 157
3.2.3 PhenylTetrahydrophthalimide 159
3.3 Non-classicalProtoxChemistries 162
3.3.1 N-PhenylHeterocycle–NewHeterocyclicSystems 163
3.3.2 PhenoxyphenylandBenzyloxyphenylAttachedtoHeterocycle 166
3.3.3 BenzoheterocyclicAttachedtoHeterocycle 169
3.3.4 BenzylAttachedtoHeterocycle 172
3.3.5 ReplacementofPhenylRingwithPyrazole 173
3.4 RecentDevelopments 174
3.5 Toxicology 181
3.6 Summary 182
References 182
4 HerbicideswithBleachingProperties 187
4.1 PhytoeneDesaturaseInhibitors 187
GerhardHamprechtandMatthiasWitschel
4.1.1 Introduction 187
4.1.2 CarotenoidBiosynthesisandPhytotoxicEffectsofBleaching
Herbicides 187
4.1.2.1 TargetsforBleachingHerbicides 187
4.1.2.2 Carotenoids–PropertiesandFunction 188
4.1.2.3 CarotenoidBiosynthesisinHigherPlants 189
4.1.3 PrimaryTargets 191
4.1.3.1 InhibitionofPhytoeneDesaturaseandz-CaroteneDesaturase 191
4.1.3.2 InhibitionofLycopeneCyclase(LCC) 191
Contents IX
4.1.3.3 GeneticEngineeringofHerbicideResistancebyModification
oftheCarotenogenicPathway 193
4.1.4 ChemicalStructureandActivitiesofPDSInhibitors 193
4.1.4.1 EnzymeActivity,PhysicalDataandAcuteOralToxicity
ofCommercialPDSHerbicides 193
4.1.4.2 Phenoxybenzamides 193
4.1.4.3 Phenoxypyridincarbonamides 193
4.1.4.4 PhenoxypyridineEthers 196
4.1.4.5 Phenylfuranones 196
4.1.4.6 Phenylpyridazinones 196
4.1.4.7 Phenylpyridinones 198
4.1.4.8 Phenylpyrrolidinones 199
4.1.4.9 Phenyltetrahydropyrimidinones 199
4.1.4.10 StructuralOverlayforDiarylHeterocyclePDSInhibitorsand
NewerDevelopments 200
4.1.4.11 ModelsoftheActiveSite–StructuralRequirements 201
4.1.5 BiologyandUsePattern 205
4.1.6 MajorSyntheticRoutesforPhytoeneDesaturaseInhibitors 208
References 208
4.2 HydroxyphenylpyruvateDioxygenase(HPPD)–theHerbicideTarget 211
TimothyR.Hawkes
References 220
4.3 HydroxyphenylpyruvateDioxygenase(HPPD)Inhibitors:Triketones 221
AndrewJ.F.Edmunds
4.3.1 Introduction 221
4.3.2 Discovery 222
4.3.3 ModeofAction 223
4.3.4 SynthesisofTriketones 224
4.3.5 Structure–ActivityRelationships 225
4.3.6 ReviewofthePatentLiterature 227
4.3.7 CommercializedTriketoneHerbicides 234
4.3.8 Summary 239
References 240
4.4 HydroxyphenylpyruvateDioxygenase(HPPD)Inhibitors:
Heterocycles 243
AndreasvanAlmsick
4.4.1 Introduction 243
4.4.2 MarketProducts 245
4.4.2.1 Pyrazolynate(Pyrazolate) 245
4.4.2.2 Pyrazoxyfen 247