Bioactive Heterocyclic Compound Classes: AgrochemicalsISBN: 978-3-527-33396-7
Hardcover
302 pages
October 2012
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Contents
Preface XI
List of Contributors XIII
Introduction 1
1 The Significance of Heterocycles for Pharmaceuticals and Agrochemicals 3
Clemens Lamberth and Jürgen Dinges
1.1 Introduction 3
1.2 Heterocycles as Framework of Biologically Active Compounds 4
1.3 Fine-Tuning the Physicochemical Properties with Heterocycles 6
1.4 Heterocycles as Prodrugs 6
1.5 Heterocycles as Peptidomimetics 7
1.6 Heterocycles as Isosteric Replacement of Functional Groups 8
1.7 Heterocycles as Isosteric Replacement of Alicyclic Rings 11
1.8 Heterocycles as Isosteric Replacement of other Heterocyclic Rings 13
References 16
Part I Herbicides 21
2 Triazine Herbicides 23
Andrew J.F. Edmunds
2.1 Introduction 23
2.2 History 23
2.3 Synthesis 27
2.4 Mode of Action 31
2.5 Biological Activity 34
2.6 Structure–Activity Relationships 34
References 37
3 Pyrimidinyl and Triazinylsulfonylurea Herbicides 39
Mary Ann Hanagan and Atul Puri
3.1 Introduction 39
3.2 History 39
3.3 Synthesis 41
3.4 Mode of Action 45
3.5 Biological Activity 46
3.6 Structure–Activity Relationship 47
References 48
4 Acetohydroxyacid Synthase Inhibiting Triazolopyrimidine Herbicides 51
Timothy C. Johnson, Richard K. Mann, Paul R. Schmitzer, and Roger E. Gast
4.1 Introduction 51
4.2 History 51
4.3 Synthesis 53
4.4 Mode of Action 55
4.5 Biological Activity 56
4.6 Structure–Activity Relationship 57
References 59
5 HPPD-Inhibiting Benzoylpyrazole Herbicides 61
Matthias Witschel
5.1 Introduction 61
5.2 History 61
5.3 Synthesis 62
5.4 Mode of Action 64
5.5 Biological Activity 66
5.6 Structure–Activity Relationship 66
References 68
6 Pyridyloxyphenoxypropionate Herbicides: Inhibitors of Acetyl-CoA Carboxylase 69
William G. Whittingham
6.1 Introduction 69
6.2 History 69
6.3 Synthesis 71
6.4 Mode of Action 73
6.5 Biological Activity 75
6.6 Structure–Activity Relationships 76
References 80
7 Imidazolinone Herbicides 83
Dale Shaner
7.1 Introduction 83
7.2 History 83
7.3 Synthesis 85
7.4 Mode of Action 86
7.5 Biological Activity 86
7.6 Structure–Activity Relationship 88
References 89
8 Protoporphyrinogen-IX-Oxidase-Inhibiting Uracil Herbicides 91
George Theodoridis
8.1 Introduction 91
8.2 History 91
8.3 Synthesis 92
8.4 Mode of Action 94
8.5 Biological Activity 94
8.6 Structure–Activity Relationship 97
References 100
Part II Fungicides 103
9 Benzimidazole Fungicides 105
Laura Quaranta
9.1 Introduction 105
9.2 History 105
9.3 Synthesis 108
9.4 Mode of Action 110
9.5 Biological Activity 112
9.6 Structure–Activity Relationship 114
References 116
10 Morpholine Fungicides for the Treatment of Powdery Mildew 119
Clemens Lamberth
10.1 Introduction 119
10.2 History 119
10.3 Synthesis 120
10.4 Mode of Action 122
10.5 Biological Activity 123
10.6 Structure–Activity Relationship 124
References 126
11 Sterol Biosynthesis Inhibiting Triazole Fungicides 129
Paul Worthington
11.1 Introduction 129
11.2 History 129
11.3 Synthesis 134
11.4 Mode of Action 138
11.5 Biological Activity 140
11.6 Structure–Activity Relationship 141
References 143
12 Methionine Biosynthesis-Inhibiting Anilinopyrimidine Fungicides 147
Clemens Lamberth
12.1 Introduction 147
12.2 History 147
12.3 Synthesis 148
12.4 Mode of Action 150
12.5 Biological Activity 151
12.6 Structure–Activity Relationship 151
References 153
13 Phenylpyrrole Fungicides 155
Clemens Lamberth
13.1 Introduction 155
13.2 History 155
13.3 Synthesis 156
13.4 Mode of Action 158
13.5 Biological Activity 158
13.6 Structure–Activity Relationship 160
References 161
14 Broad-Spectrum Fungicidally Active Pyrimidinyldioxy Strobilurins Inhibiting the Respiratory Chain 163
Clemens Lamberth
14.1 Introduction 163
14.2 History 163
14.3 Synthesis 165
14.4 Mode of Action 165
14.5 Biological Activity 168
14.6 Structure–Activity Relationship 169
References 173
15 Pyrazole Carboxamide Fungicides Inhibiting Succinate Dehydrogenase 175
Harald Walter
15.1 Introduction 175
15.2 History 175
15.3 Synthesis 177
15.4 Mode of Action 183
15.5 Biological Activity 185
15.6 Structure–Activity Relationships 187
Acknowledgements 191
References 191
Part III Insecticides 195
16 Avermectin Insecticides and Acaricides 197
Thomas Pitterna
16.1 Introduction 197
16.2 History 197
16.3 Synthesis 199
16.4 Mode of Action 201
16.5 Biological Activity 202
16.6 Structure–Activity Relationship 204
References 206
17 Pyridine and Thiazole-Containing Insecticides as Potent Agonists on Insect Nicotinic Acetylcholine Receptors 209
Peter Jeschke
17.1 Introduction 209
17.2 History 209
17.3 Synthesis 211
17.4 Mode of Action 214
17.5 Biological Activity 215
17.6 Structure–Activity Relationship 217
References 221
18 Pyrazole and Pyrimidine Acaricides and Insecticides Acting as Inhibitors of Mitochondrial Electron Transport at Complex I 225
Ottmar Franz Hüter
18.1 Introduction 225
18.2 History 225
18.3 Synthesis 227
18.4 Mode of Action 229
18.5 Biological Activity 230
18.6 Structure–Activity Relationship 230
References 236
19 Phenylpyrazole-Containing Fiprole Insecticides 239
Stefan Schnatterer
19.1 Introduction 239
19.2 History 239
19.3 Synthesis 241
19.4 Mode of Action 244
19.5 Biological Activity 244
19.6 Structure–Activity Relationship 246
References 248
20 Pyrazolylpyridine Activators of the Insect Ryanodine Receptor 251
George P. Lahm, Thomas P. Selby, Thomas M. Stevenson, Daniel Cordova, I. Billy Annan, and John T. Andaloro
20.1 Introduction 251
20.2 History 251
20.3 Synthesis 253
20.4 Mode of Action 254
20.5 Biological Activity 255
20.6 Structure–Activity Relationships 256
References 262
21 Tetronic Acid Insecticides and Acaricides Inhibiting Acetyl-CoA Carboxylase 265
Thomas Bretschneider, Reiner Fischer, and Ralf Nauen
21.1 Introduction 265
21.2 History 265
21.3 Synthesis 268
21.4 Mode of Action 269
21.5 Biological Activity 271
21.6 Structure–Activity Relationship 274
References 277
Index 279
