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
2.4.1 Point Mutation in psbA Gene ..................... 33
2.4.2 Glutathione Conjugation ......................... 33
2.4.3 Metabolic Resistance ............................ 34
2.5 Biological Activity .................................... 34
2.6 Structure-Activity Relationships ....................... 34
References .................................................. 37
3 Pyrimidinyl and Triazinylsulfonylurea Herbicides ............ 39
Maty Ann Hanagan and Atul Puri
3.1 Introduction ........................................... 39
3.2 History ................................................ 39
3.2.1 Propyrisulfuron ................................. 41
3.2.2 Metazosulfuron .................................. 41
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-lnhibiting 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-lnhibiting 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
Gemens 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 ................................................. 261
14 Broad-Spectrum Fungicidally Active Pyrimidinyldioxy
Strobilurins Inhibiting the Respiratory Chain .............. 263
Clemens Lamberth
14.1 Introduction .......................................... 163
14.2 History ............................................... 163
14.3 Synthesis ............................................. 165
14.4 Mode of Action ........................................ 265
14.5 Biological Activity ................................... 268
14.6 Structure-Activity Relationship ....................... 269
References ................................................. 173
15 Pyrazole Carboxamide Fungicides Inhibiting Succinate
Dehydrogenase .............................................. 175
Harald Walter
15.1 Introduction .......................................... 275
15.2 History ............................................... 275
15.3 Synthesis ............................................. 177
15.4 Mode of Action ........................................ 183
15.5 Biological Activity ................................... 285
15.5.1 The Foliar Pyrazole Carboxamides ............... 285
15.5.2 The Seed Treatment Pyrazole Carboxamides ....... 286
15.6 Structure-Activity Relationships ...................... 187
Acknowledgements ........................................... 292
References ................................................. 292
Part III Insecticides ........................................ 295
16 Avermectin Insecticides and Acaricides ..................... 297
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 ........................................ 224
17.5 Biological Activity ................................... 225
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
20.6.1 Rynaxypyr® ..................................... 256
20.6.2 R1 (6-Substituent of the Anthranilic Ring) ..... 257
20.6.3 R2 (4-Substituent of the Anthranilic Ring) ..... 257
20.6.4 R3 (Amide Residue) ............................. 257
20.6.5 R4 (3-Pyrazole Substituent) .................... 258
20.6.6 R5 and A (N-Substituted Aryl or Heteroaryl
Group) ......................................... 258
20.6.7 CyazypyrTM ..................................... 258
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
|
