Modern crop protection compounds: 1 [Herbicides]
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| Format: | Buch |
| Sprache: | Englisch |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2012
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| Ausgabe: | 2., rev. and enl. ed. |
| Links: | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=024630554&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| Umfang: | XXXVII, 534 S. Ill., graph. Darst. |
| ISBN: | 9783527329656 |
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| 049 | |a DE-1028 |a DE-11 |a DE-20 |a DE-1029 | ||
| 245 | 1 | 0 | |a Modern crop protection compounds |n 1 |p [Herbicides] |c edited by Wolfgang Krämer [und weiteren] |
| 250 | |a 2., rev. and enl. ed. | ||
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2012 | |
| 300 | |a XXXVII, 534 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 700 | 1 | |a Kraemer, Wolfgang |4 edt | |
| 700 | 1 | |a Jeschke, Peter |d 1956- |0 (DE-588)1181831407 |4 edt | |
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| adam_text | IMAGE 1
CONTENTS
VOLUME 1
PREFACE XXIII
LIST OF CONTRIBUTORS XXV
I HERBICIDES 1
OVERVIEW 3
MATTHIAS WITSCHET
1 HRAC CLASSIFICATION OF HERBICIDES AND RESISTANCE DEVELOPMENT 5 HUBERT
MENNE AND HELMUT KOECHER
1.1 INTRODUCTION 5
1.2 HRAC CLASSIFICATION SYSTEM OF HERBICIDES 7 1.3 HERBICIDE RESISTANCE
7
1.3.1 BIOCHEMISTRY OF HERBICIDE RESISTANCE 13 1.3.1.1 TARGET-SITE
RESISTANCE 14 1.3.1.2 NON-TARGET-SITE RESISTANCE BY ENHANCED METABOLIC
DETOXIFICATION 21 1.3.1.3 NON-TARGET-SITE RESISTANCE BY ALTERED
HERBICIDE DISTRIBUTION 24 1.3.1.4 MULTIPLE RESISTANCE 25
REFERENCES 26
2 ACETOHYDROXYACID SYNTHASE INHIBITORS (AHAS/ALS) 29
2.1 BIOCHEMISTRY OF THE TARGET AND RESISTANCE 29 STEVEN GUTTERIDGE AND
MARK E. THOMPSON
2.1.1 ACETOHYDROXYACID SYNTHASE (AHAS) 29 2.1.2 HIGHER-ORDER SUBUNIT
STRUCTURE 33 2.1.3 HERBICIDES THAT TARGET AHAS 35 2.1.4 BINDING SITE FOR
AHAS-INHIBITING HERBICIDES 36 2.1.5 MOLECULAR BASIS FOR RESISTANCE TO
AHAS INHIBITORS 41 2.1.6 RESISTANCE TO AHAS-INHIBITING HERBICIDES IN
WEEDS 43
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/1011200562
DIGITALISIERT DURCH
IMAGE 2
VI CONTENTS
2.1.7 ENGINEERED RESISTANCE TO AHAS-INHIBITING HERBICIDES IN CROPS 46
ACKNOWLEDGMENTS 46 REFERENCES 47
2.2 NEWER SULFONYLUREAS 50 OSWALD ORT
2.2.1 INTRODUCTION 50
2.2.1.1 HISTORY AND DEVELOPMENT 52 2.2.1.2 SYNTHESIS 56
2.2.2 AGRICULTURAL UTILITY 56
2.2.2.1 CEREALS 57
2.2.2.2 RICE 67
2.2.2.3 MAIZE 75
2.2.2.4 OTHER CROPS 78
2.2.3 SULFONYLUREA HERBICIDES: METABOLIC FATE AND BEHAVIOR IN THE SOIL
81 2.2.4 CONCLUDING REMARKS 83
ACKNOWLEDGMENTS 83 REFERENCES 83
2.3 IMIDAZOLINONE HERBICIDES 88 DALE L. SHANER, MARK STIDHAM, BIJAY
SINGH, AND SIYUAN TAN
2.3.1 OVERVIEW 88
2.3.2 HISTORY OF DISCOVERY 90
2.3.3 PHYSICO-CHEMICAL PROPERTIES 91 2.3 A STRUCTURAL FEATURES OF
HERBICIDAL IMIDAZOLINONES 92 2.3.5 IMIDAZOLINONES: THE MODE OF ACTION 93
2.3.6 IMIDAZOLINONE-TOLERANT CROPS 94 2.3.7 IMIDAZOLINONES: MECHANISMS
OF SELECTIVITY 95 2.3.8 COMMERCIAL USES OF THE IMIDAZOLINONE HERBICIDES
96 2.3.9 CONCLUSION 98
REFERENCES 98
2.4 TRIAZOLOPYRIMIDINES 99 TIMOTHY C. JOHNSON, RICHARD K. MANN, PAUL R.
SCHMITZER, ROGER E. GAST, AND GERRIT J. DEBOER
2.4.1 INTRODUCTION 99
2.4.2 N-TRIAZOLO[L,5-C]PYRIMIDINE SULFONANILIDE 100 2.4.2.1 SYNTHESIS
200
2.4.2.2 BIOLOGY 100
2.4.2.3 CLORANSULAM-METHYL AND DICLOSULAM CROP UTILITY 202 2.4.2.4
MECHANISM OF CROP SELECTIVITY 203 2.4.2.5 ENVIRONMENTAL DEGRADATION,
ECOTOXICOLOGY, AND TOXICOLOGY 204 2.4.3 N-TRIAZOLO[L,5-C]PYRIMIDINE
SULFONAMIDES 205
IMAGE 3
CONTENTS VII
2.4.3.1 SYNTHESIS 206
2.4.3.2 BIOLOGY 207 2.4.3.3 PENOXSULAM CROP UTILITY 209 2.4.3.4
PENOXSULAM: MECHANISM OF CROP SELECTIVITY 209 2.4.3.5 PENOXSULAM:
ENVIRONMENTAL DEGRADATION, ECOTOXICOLOGY, AND
TOXICOLOGY 220
2.4.4 N-TRIAZOLO[L,5-A]PYRIMIDINE SULFONAMIDES 222 2.4.4.1 SYNTHESIS 222
2.4.4.2 BIOLOGY 222 2.4.4.3 PYROXSULAM: CROP UTILITY 222 2.4.4.4
PYROXSULAM: MECHANISM OF CROP SELECTIVITY 222 2.4.4.5 PYROXSULAM:
ENVIRONMENTAL DEGRADATION, ECOTOXICOLOGY, AND
TOXICOLOGY 223
2.4.5 AHAS INHIBITION 2 14
2.4.6 CONCLUSIONS 225
REFERENCES 225
2.5 PYRIMIDINYLCARBOXYLATES AND SULFONANILIDES 227 TAKUMI YOSHIMURA, RYO
HANAI, AND TSUTOMU SHIMIZU
2.5.1 INTRODUCTION 227
2.5.2 DISCOVERY OF THE PCS HERBICIDES 228 2.5.3 STRUCTURE-ACTIVITY
RELATIONSHIPS OF PCS HERBICIDES 220 2.5.3.1 EFFECTS OF BENZENE RING
SUBSTITUENTS IN THE O-PYRIMIDINYLSALICYLIC ACIDS 222 2.5.3.2 EFFECT OF A
BRIDGE ATOM IN THE PYRIMIDINYLSALICYLATES 223 2.5.3.3
PYRIMIDINYLGLYCOLATES 223 2.5.4 PYRITHIOBAC-SODIUM : COTTON HERBICIDE
225 2.5.4.1 DISCOVERY 225 2.5.4.2 BIOLOGY 226
2.5.5 BISPYRIBAC-SODIUM : HERBICIDE IN DIRECT-SEEDED RICE 228 2.5.5.1
DISCOVERY 228 2.5.5.2 BIOLOGY 228 2.5.6 PYRIMINOBAC-METHYL : RICE
HERBICIDE 229
2.5.6.1 DISCOVERY 229 2.5.6.2 BIOLOGY 232 2.5.7 MODE OF ACTION OF THE
PCS HERBICIDES 232 2.5.8 MODE OF SELECTIVITY OF THE PCS HERBICIDES IN
CROPS 233
2.5.9 DISCOVERY OF THE SULFONANILIDES 234 2.5.10 STRUCTURE-ACTIVITY
RELATIONSHIPS 235 2.5.10.1 EFFECT OF THE SULFONAMIDE MOIETY IN THE
SULFONANILIDES I36 2.5.10.2 EFFECTS OF THE BRIDGE MOIETY IN THE
SULFONANILIDES 236 2.5.10.3 EFFECTS OF BENZENE RING SUBSTITUTION IN THE
SULFONANILIDES 237
2.5.11 PYRIMISULFAN : RICE HERBICIDE 239
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VIII CONTENTS
2.5.11.1 BIOLOGY 239
ABBREVIATIONS 240 REFERENCES 140
2.6 SULFONYLAMINOCARBONYL-TRIAZOLINONES 242 KLAUS-HELMUT MUELLER,
ERNST-RUDOLF F. GESING, AND HANS-JOACHIM SANTA
2.6.1 INTRODUCTION 242
2.6.2 DISCOVERY OF THE LEAD STRUCTURE 243 2.6.3 OPTIMIZATION OF THE LEAD
STRUCTURE 243 2.6.4 DISCOVERY OF THIENCARBAZONE-METHYL (TCM) 246 2.6.5
SYNTHESIS 248
2.6.5.1 SULFONYL COMPONENTS 249 2.6.5.2 TRIAZOLINONE SYNTHESIS 250 2.6.6
BIOLOGY 252
2.6.7 CONCLUSIONS 258
REFERENCES 258
3 PROTOPORPHYRINOGEN IX OXIDASE INHIBITORS 163 GEORGE THEODORIDIS, REX
LIEBL, AND CYRILL ZAGAR
3.1 INTRODUCTION 263
3.2 HISTORICAL DEVELOPMENT 265
3.2.1 DIPHENYL ETHER 265
3.2.2 PHENYL RING ATTACHED TO HETEROCYCLE 266 3.2.3 PHENYL
TETRAHYDROPHTHALIMIDE 268 3.3 NON-CLASSICAL PROTOX CHEMISTRIES 172 3.3.1
N-PHENYL HETEROCYDES: NEW HETEROCYCLIC SYSTEMS 272 3.3.2 PHENOXYPHENYL
AND BENZYLOXYPHENYL ATTACHED TO HETEROCYCLE 276 3.3.3 BENZOHETEROCYCLIC
ATTACHED TO HETEROCYCLE 278 3.3.4 BENZYL ATTACHED TO HETEROCYCLE 282
3.3.5 REPLACEMENT OF PHENYL RING WITH PYRAZOLE 282 3.4 RECENT
DEVELOPMENTS 282
3.5 TOXICOLOGY 290
3.6 SUMMARY 290
REFERENCES 292
4 HERBICIDES WITH BLEACHING PROPERTIES 297
4.1 PHYTOENE DESATURASE INHIBITORS 297 GERHARD HAMPRECHT AND MATTHIAS
WITSCHET
4.1.1 INTRODUCTION 297
4.1.2 CAROTENOID BIOSYNTHESIS AND PHYTOTOXIC EFFECTS OF BLEACHING
HERBICIDES 297 4.1.2.1 TARGETS FOR BLEACHING HERBICIDES 297
IMAGE 5
CONTENTS IX
4.1.2.2 CAROTENOIDS: PROPERTIES AND FUNCTIONS 198
4.1.2.3 CAROTENOID BIOSYNTHESIS IN HIGHER PLANTS 299 4.1.3 PRIMARY
TARGETS 202
4.1.3.1 INHIBITION OF PDS AND C -CAROTENE DESATURASE 202 4.1.3.2
INHIBITION OF LYCOPENE CYCLASE (LCC) 202 4.1.3.3 GENETIC ENGINEERING OF
HERBICIDE RESISTANCE BY MODIFICATION OF THE CAROTENOGENIC PATHWAY 203
4.1.4 CHEMICAL STRUCTURE AND ACTIVITIES OF PDS INHIBITORS 203 4.1.4.1
ENZYME ACTIVITY, PHYSICAL DATA, AND ACUTE ORAL TOXICITY OF COMMERCIAL
PDS HERBICIDES 203 4.1.4.2 PHENOXYBENZAMIDES 203
4.1.4.3 PHENOXYPYRIDINECARBONAMIDES 206 4.1.4.4 PHENOXYPYRIDINE ETHERS
207 4.1.4.5 PHENYLFURANONES 207 4.1.4.6 PHENYLPYRIDAZINONES 209 4.1.4.7
PHENYLPYRIDINONES 220 4.1.4.8 PHENYLPYRROLIDINONES 220 4.1.4.9
PHENYLTETRAHYDROPYRIMIDINONES 222 4.1.4.10 STRUCTURAL OVERLAY FOR DIARYL
HETEROCYCLE PDS INHIBITORS, AND NEWER
DEVELOPMENTS 222
4.1.4.11 MODELS OF THE ACTIVE SITE: STRUCTURAL REQUIREMENTS 212 4.1.5
BIOLOGY AND USE PATTERN 217 4.1.6 MAJOR SYNTHETIC ROUTES FOR PSD
INHIBITORS 228 REFERENCES 222
4.2 HYDROXYPHENYLPYRUVATE DIOXYGENASE (HPPD): THE HERBICIDE TARGET 225
TIMOTHY R. HAWKES
4.2.1 HERBICIDAL MODE OF ACTION 225 4.2.2 SELECTIVITY 228
4.2.3 STRUCTURE AND MECHANISM 229 4.2.4 INHIBITION 232
REFERENCES 234
4.3 TRIKETONES 235
ANDREW J.F. EDMUNDS AND JAMES A. MORRIS
4.3.1 INTRODUCTION 235
4.3.2 DISCOVERY 236
4.3.3 MODE OF ACTION 237
4.3.4 SYNTHESIS OF TRIKETONES 237 4.3.5 STRUCTURE-ACTIVITY RELATIONSHIPS
(SARS) 239 4.3.6 REVIEW OF THE PATENT LITERATURE 241 4.3.7
COMMERCIALIZED TRIKETONE HERBICIDES 249
IMAGE 6
X CONTENTS
4.3.7.1 SULCOTRIONE 249
4.3.7.2 MESOTRIONE 250
4.3.7.3 TEMBOTRIONE AND TEFURYLTRIONE 254 4.3.7.4 BENZOBICYCLON 256
4.3.8 SUMMARY 258
REFERENCES 258
4.4 HYDROXYPHENYLPYRUVATE DIOXYGENASE (HPPD) INHIBITORS: HETEROCYCLES
262 ANDREAS VAN ALMSICK
4.4.1 INTRODUCTION 262
4.4.2 MARKET PRODUCTS 263
4.4.2.1 PYRAZOLYNATE (PYRAZOLATE) 263 4.4.2.2 PYRAZOXYFEN 266 4.4.2.3
BENZOFENAP 267 4.4.2.4 ISOXAFLUTOLE 269 4.4.2.5 TOPRAMEZONE 271 4.4.2.6
PYRASULFOTOLE 272 4.4.3 CONCLUSIONS 274
REFERENCES 275
5 NEW AUXIN MIMICS AND HERBICIDES 277
5.1 THE MOLECULAR MODE OF ACTION OF AUXIN HERBICIDES 277 TERENCE. A.
WALSH AND PAUL R. SCHMITZER
5.1.1 INTRODUCTION 277
5.1.2 TIR1/AFB PROTEINS AS AUXIN HERBICIDE RECEPTORS 277 5.1.3 THE AFB5
CLASS OF PICOLINATE AUXIN HERBICIDE RECEPTORS 282 5.1.4 TIR1/AFB AUXIN
RECEPTORS IN OTHER PLANTS 282 5.1.5 ARE THERE OTHER AUXIN HERBICIDE
RECEPTORS? 282 5.1.6 DOWNSTREAM EFFECTS OF AUXIN HERBICIDES 283
5.1.7 WEED SELECTIVITIES AT THE SITE OF AUXIN ACTION 283 5.1.8 FIELD
RESISTANCE TO AUXIN HERBICIDES 285 5.1.9 CONCLUSIONS 285
REFERENCES 286
5.2 AMINOPYRALID 287
ROBERT A. MASTERS, WILLIAM C. LO, AND ROGER E. GAST
5.2.1 INTRODUCTION 287
5.2.2 AMINOPYRALID SYNTHESIS 288 5.2.3 BIOLOGY 288
5.2.4 AMINOPYRALID UTILITY 290 5.2.5 AMINOPYRALID MECHANISM OF CROP
SELECTIVITY 292 5.2.6 AMINOPYRALID ENVIRONMENTAL DEGRADATION 292
IMAGE 7
CONTENTS XI
5.2.6.1 ANIMAL TOXICITY 293
5.2.6.2 CARCINOGENICITY/TERATOGENICITY 294 5.2.7 CONCLUSIONS 294
REFERENCES 294
5.3 PYRIMIDINE CARBOXYLIC ACIDS, AMINOCYCLOPYRACHLOR 295 JON S. CLAUS
AND BRUCE L. FINKELSTEIN
5.3.1 INTRODUCTION 295
5.3.2 DISCOVERY OF AMINOCYCLOPYRACHLOR 295 5.3.3 HERBICIDAL ACTIVITY AND
THE PROPERTIES OF AMINOCYCLOPYRACHLOR 300 5.3.4 MODE OF ACTION AND SITE
OF ACTION 302 5.3.5 RESISTANCE MANAGEMENT 303
5.3.6 CONCLUSIONS 303
REFERENCES 304
6 HERBICIDES DISTURBING THE SYNTHESIS OF VERY LONG-CHAIN FATTY ACIDS 305
6.1 INHIBITORS OF THE SYNTHESIS OF VERY LONG-CHAIN FATTY ACIDS (VLCFAS)
305 PETER BABCZINSKI
6.1.1 BIOCHEMISTRY 305
6.1.1.1 INTRODUCTION 305 6.1.1.2 HRAC CLASSIFICATION 305 6.1.1.3
BIOSYNTHESIS OF VLCFAS 306 REFERENCES 324
6.2 CHEMISTRY AND BIOLOGY OF OXYACETAMIDES, TETRAZOLINONES, AND
TRIAZOLINONES 326 YUKIYOSHI WATANABE
6.2.1 INTRODUCTION 326
6.2.2 MEFENACET AND FLUFENACET (OXYACETAMIDES) 316 6.2.3 FENTRAZAMIDE
(TETRAZOLINONE) 328 6.2.4 IPFENCARBAZON (TRIAZOLINONE) 322 6.2.5
CONCLUSIONS 324
ACKNOWLEDGMENTS 324 REFERENCES 325
6.3 ISOXAZOLINES 326
MASAO NAKATANI, TAKUMI YOSHIMURA, RYO HANAI, YOSHITAKA TANETANI, AND
TSUTOMU SHIMIZU
6.3.1 INTRODUCTION 326
6.3.2 CHEMISTRY OF PYROXASULFONE 326
IMAGE 8
XII I CONTENTS
6.3.3 BIOLOGICAL ACTIVITIES OF PYROXASULFONE 328
6.3.4 BIOLOGICAL ACTIVITIES OF FENOXASULFONE 330 6.3.5 MODE OF ACTION OF
PYROXASULFONE 330 6.3.6 MODE OF ACTION OF FENOXASULFONE 334
ABBREVIATIONS 335
REFERENCES 335
7 INHIBITORS OF CELLULOSE BIOSYNTHESIS 339 HANSJOERG DIETRICH AND BERND
LABER
7.1 7.1.1 7.2
7.2.1 7.2.1.1 7.2.1.2 7.2.2 7.2.2.1
7.2.2.2 7.2.3 7.2.3.1
7.2.3.2 7.2.4 7.2.4.1 7.2.4.2
7.2.5 7.2.5.1 7.2.5.2 7.2.6 7.2.6.1 7.2.6.2 7.2.7 7.2.8
7.3 7.3.1 7.3.2 7.3.3
INTRODUCTION 339 CELLULOSE BIOSYNTHESIS 339 CELLULOSE BIOSYNTHESIS
INHIBITORS FROM DIFFERENT CHEMICAL SUBSTANCE CLASSES 344 NITRILES 345
CHEMISTRY OF BENZONITRILES 345
BIOLOGICAL ACTIVITY OF BENZONITRILES 346 BENZAMIDES 348 CHEMISTRY OF
BENZAMIDES 348 BIOLOGY OF ISOXABEN 349 TRIAZOLOCARBOXAMIDES 352
CHEMISTRY OF TRIAZOLOCARBOXAMIDES 352 BIOLOGY OF TRIAZOLOCARBOXAMIDES:
FLUPOXAM 352 ALKYLAZINES 353 CHEMISTRY OF ALKYLAZINES 353
BIOLOGY OF ALKYLAZINES 354 THIARRIAZINES 356 CHEMISTRY OF THIATRIAZINES
356
BIOLOGY OF CGA 325615 357 JV-ARYL LACTAMS 359 CHEMISTRY OF N-ARYL
LACTAMS 359 BIOLOGY OF N-ARYL LACTAMS 359 COUMARINS 360
PROPERTIES OF COMMERCIALIZED INHIBITORS OF CELLULOSE BIOSYNTHESIS 362
CELLULOSE BIOSYNTHESIS INHIBITORS FROM NATURAL SOURCES 362 THAXTOMINS
362 INTHOMYCINS 364 EPOPROMYCINS 365 REFERENCES 365
8 SAFENERS FOR HERBICIDES 372
CHRIS ROSINGER, KLAUS BARTSCH, AND WOLFGANG SCHULTE
8.1 INTRODUCTION 372
8.2 OVERVIEW OF SELECTED SAFENERS 372
IMAGE 9
CONTENTS XIII
8.2.1 DICHLOROACETAMIDE SAFENERS 372
8.2.1.1 BENOXACOR 375 8.2.1.2 DICHLORMID 377 8.2.1.3 FURILAZOLE 378
8.2.2 OXIME ETHERS 379
8.2.3 CLOQUINTOCET-MEXYL 379 8.2.4 MEFENYPR-DIETHYL 380 8.2.5
ISOXADIFEN-ETHYL 382 8.2.6 CYPROSULFAMIDE 383
8.3 MECHANISMS OF HERBICIDE SAFENER ACTION 385 8.3.1 EFFECTS OF SAFENERS
ON HERBICIDE METABOLISM 385 8.3.2 GENE INDUCTION AND SIGNALING PATHWAYS
387 8.3.3 INFLUENCE ON HERBICIDE UPTAKE 388 8.3.4 INFLUENCE ON HERBICIDE
TRANSLOCATION 388 8.4 MODE OF ACTION OF SAFENERS IN AGRICULTURAL
PRACTICE 389 8.4.1 1,8-NAPHTHALIC ANHYDRIDE (NA), FLURAZOLE, AND
FLUXOFENIM 389
8.4.2 DICHLOROACETAMIDES 390 8.4.3 FENCLORIM 392
8.4.4 FENCHLORAZOLE-ETHYL, CLOQUINTOCET-MEXYL 392 8.4.5 MEFENPYR-DIETHYL
392 8.4.6 ISOXADIFEN-ETHYL 393 8.4.7 CYPROSULFAMIDE 394
8.5 CONCLUDING REMARKS 394
REFERENCES 395
9 GENETICALLY MODIFIED HERBICIDE-RESISTANT CROPS 399
9.1 OVERVIEW 399
SUSAN J. MARTINO-CATL, PAUL C.C. FENG, AND STEPHEN R. PADGETTE
9.1.1 INTRODUCTION 399
9.1.2 MECHANISMS FOR ENGINEERING HERBICIDE RESISTANCE 400 9.1.2.1
DETOXIFICATION OF HERBICIDES 400 9.1.2.2 EXPRESSION OF AN INSENSITIVE
HERBICIDE TARGET 401 9.1.3 COMMERCIALIZED HERBICIDE-RESISTANT CROPS 402
9.1.3.1 HERBICIDE-RESISTANT SOYBEANS 401 9.1.3.2 HERBICIDE-RESISTANT
COTTON 402 9.1.3.3 HERBICIDE-RESISTANT CORN 403
9.1.3.4 HERBICIDE-RESISTANT CANOLA 404 REFERENCES 406
IMAGE 10
XIV CONTENTS
9.2 INHIBITORS OF 5-ENOLPYRUVYL SHIKIMATE 3-PHOSPHATE SYNTHASE
(EPSPS) 406 PAUL C.C. FENG, SUSAN MARTINO-CATT, AND STEPHEN R. PADGEIIE
9.2.1 INTRODUCTION 406
9.2.2 FACTORS THAT IMPACT GLYPHOSATE EFFICACY 407 9.2.2.1 FOLIAR
ABSORPTION 407 9.2.2.2 SYSTEMIC TRANSLOCATION 409 9.2.3 DEVELOPMENT OF
GLYPHOSATE-RESISTANT CROPS 422
9.2.3.1 ALTERNATIVE MECHANISMS FOR ENGINEERING GLYPHOSATE RESISTANCE 412
9.2.3.2 DISEASE CONTROL BENEFITS OF GLYPHOSATE-RESISTANT CROPS 412 9.2.4
EFFECTS OF CP4 EXPRESSION ON PLANT RESISTANCE 424 9.2.4.1 ROUNDUP READY
COTTON 425 9.2.4.2 ROUNDUP READY CORN 426 9.2.4.3 ROUNDUP READY SOYBEAN
426 9.2.5 STACKING TRAITS IN ROUNDUP READY CROPS 426 9.2.5.1 ENGINEERING
CROP RESISTANCE TO DICAMBA 427 9.2.5.2 ENGINEERING CROP RESISTANCE TO
GLUFOSINATE 428
REFERENCES 420
9.3 CLUTAMINE SYNTHETASE INHIBITORS 423 GUENTER DONN
9.3.1 INTRODUCTION 423
9.3.2 ROLE OF GLUTAMINE SYNTHETASE IN PLANT NITROGEN METABOLISM 424
9.3.3 PHOSPHINOTHRICIN, A POTENT GS INHIBITOR 426 9.3.4 DISCOVERY OF THE
HERBICIDAL ACTIVITY OF PHOSPHINOTHRICIN 427 9.3.5 MODE OF GLUTAMINE
SYNTHETASE INHIBITION 428
9.3.6 PHYSIOLOGY OF THE HERBICIDAL ACTIVITY OF PHOSPHINOTHRICIN 429
9.3.6.1 HERBICIDAL SYMPTOMS OF PHOSPHINOTHRICIN 429 9.3.6.2
PHYSIOLOGICAL EFFECTS OF GS INHIBITION IN PLANTS 429 9.3.6.3 MODULATION
OF HERBICIDAL ACTIVITY OF GLUFOSINATE BY ENVIRONMENTAL
CONDITIONS 430
9.3.6.4 UPTAKE AND TRANSLOCATION OF GLUFOSINATE-AMMONIUM 430 9.3.7 USE
OF PHOSPHINOTHRICIN-CONTAINING HERBICIDES IN AGRICULTURE AND
HORTICULTURE 431 9.3.8 ATTEMPTS TO GENERATE CROP SELECTIVITY FOR
GLUFOSINATE 432 9.3.8.1 GENETIC APPROACHES TO GENERATE
GLUFOSINATE-SELECTIVITY IN CROPS:
TARGET-BASED APPROACHES 431 9.3.8.2 CROP SELECTIVITY BY EXPRESSION OF
PHOSPHINOTHRICIN ACETYL TRANSFERASE 432 9.3.8.3 BAR AND PAT GENES IN
PLANT BREEDING 433 9.3.9 THE USE OF N-ACETYL-PHOSPHINOTHRICIN AS A
PROHERBICIDE 434 9.3.10 CONCLUSIONS 435
REFERENCES 435
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CONTENTS XV
10 MICROTUBULIN ASSEMBLY INHIBITORS (PYRIDINES) 439
DARIN W. LICKFELDT, DENISE P. CUDWORTH, DANIEL D. LOUGHNER, AND LOWELL
D. MARKLEY
10.1 INTRODUCTION 439
10.2 BIOLOGY OF THE MICROTUBULIN ASSEMBLY INHIBITORS (PYRIDINES) 439
10.2.1 DITHIOPYR 439
10.2.2 THIAZOPYR 440
10.3 ENVIRONMENTAL FATE OF MICROTUBULIN ASSEMBLY INHIBITORS (PYRIDINES)
442 10.3.1 DITHIOPYR 442
10.3.2 THIAZOPYR 441
10.4 TOXICOLOGY OF MICROTUBULIN ASSEMBLY INHIBITORS (PYRIDINES) 442 10.5
MODE OF ACTION OF MICROTUBULIN ASSEMBLY INHIBITORS (PYRIDINES) 442 10.6
SYNTHESIS OF DITHIOPYR AND THIAZOPYR 443
REFERENCES 445
11 ACETYL-COA CARBOXYLASE INHIBITORS 447 JEAN WENGER, THIERRY NIDERMAN,
AND CHRIS MATHEWS
11.1 INTRODUCTION 447
11.2 BIOCHEMISTRY 447
11.2.1 OVERVIEW 447
11.2.2 MODE OF ACTION OF ACCASE INHIBITORS 450 11.2.3 RESISTANCE 453
11.2.4 DETECTION OF RESISTANCE 454 11.3 CHEMISTRY OF ACCASE INHIBITORS
455 11.3.1 ARYLOXYPHENOXYPROPIONATES (AOPPS OR FOPS) 455 11.3.2
CYCLOHEXANEDIONES (CHDS OR DIMS) 455 11.3.3 ARYL-L,3-DIONES(DENS) 460
11.3.3.1 DISCOVERY OF 2-ARYL-L,3-DIONES 460 11.3.3.2 SYNTHESES 461 11.4
STRUCTURE-ACTIVITY RELATIONSHIPS 465 11.4.1 PROCIDE STRUCTURE-ACTIVITY
RELATIONSHIPS 466 11.4.2 DIONE STRUCTURE-ACTIVITY RELATIONSHIPS 466
11.4.3 PHENYL STRUCTURE-ACTIVITY RELATIONSHIPS 467 11.4.3.1
2,4,6-TRISUBSTITUTED PHENYL STRUCTURE-ACTIVITY RELATIONSHIPS 467
11.4.3.2 2,5-DISUBSTITUTED PHENYL STRUCTURE-ACTIVITY RELATIONSHIPS 468
11.5 PINOXADEN 469
11.5.1 CHARACTERISTICS 469 11.5.2 TECHNICAL SYNTHESIS 470 11.5.3 BIOLOGY
470
11.5.4 METABOLISM AND SELECTIVITY 471 11.6 SUMMARY AND OUTLOOK 473
IMAGE 12
XVI CONTENTS
ACKNOWLEDGMENTS 474
REFERENCES 474
12 PHOTOSYNTHESIS INHIBITORS: REGULATORY ASPECTS, RE-REGISTRATION IN
EUROPE, MARKET TRENDS, AND NEW PRODUCTS 479 MARTYN GRIFFITHS,
KARL-WILHELM MUENKS, AND KLAUS-HELMUT MUELLER
12.1 INTRODUCTION 479
12.2 THE RE-REGISTRATION PROCESS IN THE EUROPEAN UNION 482 12.3 MAIN
CHANGES IN GUIDELINES REGARDING EU RE-REGISTRATION 488 12.3.1 GOOD
LABORATORY PRACTICE 488 12.3.2 PHYSICAL AND CHEMICAL PROPERTIES OF
ACTIVE SUBSTANCES 489 12.3.3 STORAGE STABILITY 489 12.3.4 PHYSICAL AND
CHEMICAL CHARACTERISTICS OF PREPARATION 489 12.3.5 OPERATOR EXPOSURE
DATA REQUIREMENTS 490 12.3.6 RESIDUE DATA REQUIREMENTS 490 12.3.7
ESTIMATION OF DIETARY INTAKES OF PESTICIDES RESIDUES 490 12.3.8 FATE AND
BEHAVIOR OF AGRICULTURAL PESTICIDES IN THE ENVIRONMENT 492 12.3.8.1
CONCENTRATION OF CHEMICAL IN THE RELEVANT ENVIRONMENTAL
COMPARTMENT 492
12.3.8.2 BIOAVAILABILITY OF THE CHEMICAL 491 12.3.8.3 NATURE OF THE
SYSTEM OR ORGANISM 492 12.3.9 SPECIFIC GUIDANCE REGARDING WATER LIMITS
ACCORDING TO ANNEXES OF THE AUTHORIZATIONS DIRECTIVE 492
12.3.10 ECOTOXICOLOGY REQUIREMENTS 492 12.3.10.1 EPPO RISK-ASSESSMENT
SCHEMES 493 12.3.10.2 BUFFER ZONES AND LERAPS 494 12.3.10.3 HONEYBEE
RISK ASSESSMENT 494 12.3.10.4 RISK TO NONTARGET ARTHROPODS 494 12.3.10.5
RISK FOR SOIL NONTARGET MICROORGANISMS 494
12.4 NEW REGULATIONS IN EUROPE 494
12.4.1 MRL REGULATION 494 12.4.2 NEW PPP REGULATION (TO REPLACE
DIRECTIVE 91/414) 495 12.4.2.1 DOSSIER 495 12.4.2.2 EFFICACY 495
12.4.2.3 METABOLITES 496 12.4.2.4 COMPOSITION 496 12.4.2.5 METHODS OF
ANALYSIS 496 12.4.2.6 IMPACT ON HUMAN HEALTH 496 12.4.2.7 FATE AND
BEHAVIOR IN THE ENVIRONMENT 497 12.4.2.8 ECOTOXICOLOGY 497 12.4.2.9
RESIDUE DEFINITION 498 12.4.2.10 FATE AND BEHAVIOR CONCERNING
GROUNDWATER 498 12.4.2.11 CANDIDATE FOR SUBSTITUTION 498 12.4.2.12
LOW-RISK ACTIVE SUBSTANCES 498
IMAGE 13
CONTENTS XVII
12.5 SITUATION OF PS II INHIBITORS IN THE EC MARKETS 499
12.6 CURRENT MARKET SHARE OF PS II COMPOUND GROUPS 500 12.7 A NEW
HERBICIDE FOR CORN AND SUGARCANE: AMICARBAZONE * BAY MKH 3586 510 12.7.1
INTRODUCTION 510
12.7.2 PHYSICO-CHEMICAL PROPERTIES OF AMICARBAZONE 521 12.7.3 DISCOVERY
OF THE ACTIVE INGREDIENT 512 12.7.4 SYNTHESIS 514
12.7.4.1 FINAL PRODUCT 514 12.7.5 BIOLOGICAL BEHAVIOR 515 12.7.6
METABOLITES 516 12.8 CONCLUSIONS 527
REFERENCES 527
13 NEW ASPECTS OF PLANT REGULATORS 523 HANS ULRICH HAAS
13.1 INTRODUCTION 523
13.2 PLANT GROWTH REGULATORS 523 13.3 PGRS IN MODERN AGRICULTURE 526
13.3.1 GROWTH INHIBITION 526 13.3.2 FRUITING AND GROWTH 528 13.3.3 FRUIT
STORAGE AND RIPENING 528
13.3.4 SPROUT INHIBITION 529 13.3.5 STRESS DEFENSE 530 13.4 CONCLUSIONS
AND DEVELOPMENTS 532 REFERENCES 532
|
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| id | DE-604.BV039769537 |
| illustrated | Illustrated |
| indexdate | 2024-12-20T16:02:09Z |
| institution | BVB |
| isbn | 9783527329656 |
| language | English |
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| spellingShingle | Modern crop protection compounds |
| title | Modern crop protection compounds |
| title_auth | Modern crop protection compounds |
| title_exact_search | Modern crop protection compounds |
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| title_fullStr | Modern crop protection compounds 1 [Herbicides] edited by Wolfgang Krämer [und weiteren] |
| title_full_unstemmed | Modern crop protection compounds 1 [Herbicides] edited by Wolfgang Krämer [und weiteren] |
| title_short | Modern crop protection compounds |
| title_sort | modern crop protection compounds herbicides |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=024630554&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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