Bioactive Heterocyclic Compound Classes: Agrochemicals

287 Pages·2012·2.51 MB·English

EditedbyClemensLamberthand
Ju¨rgenDinges
BioactiveHeterocyclicCompoundClasses
RelatedTitles
Jeschke,P.,Kra¨mer,W.,Schirmer,U., Majumdar,K.C.,Chattopadhyay,S.K.
Witschel,M.(eds.) (eds.)
ModernMethodsinCrop HeterocyclesinNatural Product
Protection Research Synthesis
2012 2011
Hardcover Hardcover
ISBN:978-3-527-33175-8 ISBN:978-3-527-32706-5
Dinges,J.,Lamberth,C.(eds.) Royer,J.(ed.)
Bioactive Heterocyclic AsymmetricSynthesisof
CompoundClasses Nitrogen Heterocycles
Pharmaceuticals
2009
2012 Hardcover
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Kra¨mer,W.,Schirmer,U.,Jeschke,P.,
Witschel,M.(eds.)
Modern CropProtection
Compounds
2012
Hardcover
ISBN:978-3-527-32965-6
Edited by Clemens Lamberth and Ju¨rgen Dinges
Bioactive Heterocyclic Compound Classes
Agrochemicals
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V
Contents
Preface XI
ListofContributors XIII
Introduction 1
1 TheSignificanceofHeterocyclesforPharmaceuticals
andAgrochemicals 3
ClemensLamberthandJu¨rgenDinges
1.1 Introduction 3
1.2 HeterocyclesasFrameworkofBiologicallyActiveCompounds 4
1.3 Fine-TuningthePhysicochemicalPropertieswithHeterocycles 6
1.4 HeterocyclesasProdrugs 6
1.5 HeterocyclesasPeptidomimetics 7
1.6 HeterocyclesasIsostericReplacementofFunctionalGroups 8
1.7 HeterocyclesasIsostericReplacementofAlicyclicRings 11
1.8 HeterocyclesasIsostericReplacementofotherHeterocyclicRings 13
References 16
PartI Herbicides 21
2 TriazineHerbicides 23
AndrewJ.F.Edmunds
2.1 Introduction 23
2.2 History 23
2.3 Synthesis 27
2.4 ModeofAction 31
2.4.1 PointMutationinpsbAGene 33
2.4.2 GlutathioneConjugation 33
2.4.3 MetabolicResistance 34
2.5 BiologicalActivity 34
2.6 Structure–ActivityRelationships 34
References 37
VI Contents
3 PyrimidinylandTriazinylsulfonylureaHerbicides 39
MaryAnnHanaganandAtulPuri
3.1 Introduction 39
3.2 History 39
3.2.1 Propyrisulfuron 41
3.2.2 Metazosulfuron 41
3.3 Synthesis 41
3.4 ModeofAction 45
3.5 BiologicalActivity 46
3.6 Structure–ActivityRelationship 47
References 48
4 AcetohydroxyacidSynthaseInhibitingTriazolopyrimidine
Herbicides 51
TimothyC.Johnson,RichardK.Mann,PaulR.Schmitzer,and
RogerE.Gast
4.1 Introduction 51
4.2 History 51
4.3 Synthesis 53
4.4 ModeofAction 55
4.5 BiologicalActivity 56
4.6 Structure–ActivityRelationship 57
References 59
5 HPPD-InhibitingBenzoylpyrazoleHerbicides 61
MatthiasWitschel
5.1 Introduction 61
5.2 History 61
5.3 Synthesis 62
5.4 ModeofAction 64
5.5 BiologicalActivity 66
5.6 Structure–ActivityRelationship 66
References 68
6 PyridyloxyphenoxypropionateHerbicides:InhibitorsofAcetyl-CoA
Carboxylase 69
WilliamG.Whittingham
6.1 Introduction 69
6.2 History 69
6.3 Synthesis 71
6.4 ModeofAction 73
6.5 BiologicalActivity 75
6.6 Structure–ActivityRelationships 76
References 80
Contents VII
7 ImidazolinoneHerbicides 83
DaleShaner
7.1 Introduction 83
7.2 History 83
7.3 Synthesis 85
7.4 ModeofAction 86
7.5 BiologicalActivity 86
7.6 Structure–ActivityRelationship 88
References 89
8 Protoporphyrinogen-IX-Oxidase-InhibitingUracilHerbicides 91
GeorgeTheodoridis
8.1 Introduction 91
8.2 History 91
8.3 Synthesis 92
8.4 ModeofAction 94
8.5 BiologicalActivity 94
8.6 Structure–ActivityRelationship 97
References 100
PartII Fungicides 103
9 BenzimidazoleFungicides 105
LauraQuaranta
9.1 Introduction 105
9.2 History 105
9.3 Synthesis 108
9.4 ModeofAction 110
9.5 BiologicalActivity 112
9.6 Structure–ActivityRelationship 114
References 116
10 MorpholineFungicidesfortheTreatmentofPowderyMildew 119
ClemensLamberth
10.1 Introduction 119
10.2 History 119
10.3 Synthesis 120
10.4 ModeofAction 122
10.5 BiologicalActivity 123
10.6 Structure–ActivityRelationship 124
References 126
11 SterolBiosynthesisInhibitingTriazoleFungicides 129
PaulWorthington
11.1 Introduction 129
VIII Contents
11.2 History 129
11.3 Synthesis 134
11.4 ModeofAction 138
11.5 BiologicalActivity 140
11.6 Structure–ActivityRelationship 141
References 143
12 MethionineBiosynthesis-InhibitingAnilinopyrimidineFungicides 147
ClemensLamberth
12.1 Introduction 147
12.2 History 147
12.3 Synthesis 148
12.4 ModeofAction 150
12.5 BiologicalActivity 151
12.6 Structure–ActivityRelationship 151
References 153
13 PhenylpyrroleFungicides 155
ClemensLamberth
13.1 Introduction 155
13.2 History 155
13.3 Synthesis 156
13.4 ModeofAction 158
13.5 BiologicalActivity 158
13.6 Structure–ActivityRelationship 160
References 161
14 Broad-SpectrumFungicidallyActivePyrimidinyldioxyStrobilurins
InhibitingtheRespiratoryChain 163
ClemensLamberth
14.1 Introduction 163
14.2 History 163
14.3 Synthesis 165
14.4 ModeofAction 165
14.5 BiologicalActivity 168
14.6 Structure–ActivityRelationship 169
References 173
15 PyrazoleCarboxamideFungicidesInhibitingSuccinate
Dehydrogenase 175
HaraldWalter
15.1 Introduction 175
15.2 History 175
15.3 Synthesis 177
15.4 ModeofAction 183
Contents IX
15.5 BiologicalActivity 185
15.5.1 TheFoliarPyrazoleCarboxamides 185
15.5.2 TheSeedTreatmentPyrazoleCarboxamides 186
15.6 Structure–ActivityRelationships 187
Acknowledgements 191
References 191
PartIII Insecticides 195
16 AvermectinInsecticidesandAcaricides 197
ThomasPitterna
16.1 Introduction 197
16.2 History 197
16.3 Synthesis 199
16.4 ModeofAction 201
16.5 BiologicalActivity 202
16.6 Structure–ActivityRelationship 204
References 206
17 PyridineandThiazole-ContainingInsecticidesasPotentAgonistson
InsectNicotinicAcetylcholineReceptors 209
PeterJeschke
17.1 Introduction 209
17.2 History 209
17.3 Synthesis 211
17.4 ModeofAction 214
17.5 BiologicalActivity 215
17.6 Structure–ActivityRelationship 217
References 221
18 PyrazoleandPyrimidineAcaricidesandInsecticidesActingasInhibitors
ofMitochondrialElectronTransportatComplexI 225
OttmarFranzHu¨ter
18.1 Introduction 225
18.2 History 225
18.3 Synthesis 227
18.4 ModeofAction 229
18.5 BiologicalActivity 230
18.6 Structure–ActivityRelationship 230
References 236
19 Phenylpyrazole-ContainingFiproleInsecticides 239
StefanSchnatterer
19.1 Introduction 239
19.2 History 239
X Contents
19.3 Synthesis 241
19.4 ModeofAction 244
19.5 BiologicalActivity 244
19.6 Structure–ActivityRelationship 246
References 248
20 PyrazolylpyridineActivatorsoftheInsectRyanodineReceptor 251
GeorgeP.Lahm,ThomasP.Selby,ThomasM.Stevenson,DanielCordova,
I.BillyAnnan,andJohnT.Andaloro
20.1 Introduction 251
20.2 History 251
20.3 Synthesis 253
20.4 ModeofAction 254
20.5 BiologicalActivity 255
20.6 Structure–ActivityRelationships 256
®
20.6.1 Rynaxypyr 256
20.6.2 R1(6-SubstituentoftheAnthranilicRing) 257
20.6.3 R2(4-SubstituentoftheAnthranilicRing) 257
20.6.4 R3(AmideResidue) 257
20.6.5 R4(3-PyrazoleSubstituent) 258
20.6.6 R5andA(N-SubstitutedArylorHeteroarylGroup) 258
20.6.7 Cyazypyr™ 258
References 262
21 TetronicAcidInsecticidesandAcaricidesInhibitingAcetyl-CoA
Carboxylase 265
ThomasBretschneider,ReinerFischer,andRalfNauen
21.1 Introduction 265
21.2 History 265
21.3 Synthesis 268
21.4 ModeofAction 269
21.5 BiologicalActivity 271
21.6 Structure–ActivityRelationship 274
References 277
Index 279