Holdings: Herbicide classes in development

Herbicide classes in development: mode of action, targets, genetic engineering, chemistry

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Bibliographic Details
Format:	Book
Language:	English
Published:	Berlin ; Heidelberg ; New York ; Barcelona ; Hong Kong ; London Springer 2002
Subjects:	Cultures résistantes aux herbicides Herbicides Herbicide-resistant crops Herbizid Klassifikation
Online Access:	Inhaltsverzeichnis
Item Description:	Literaturangaben
Physical Description:	XXI, 364 S. Ill., graph. Darst. : 24 cm
ISBN:	3540431470

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245	1	0	\|a Herbicide classes in development \|b mode of action, targets, genetic engineering, chemistry \|c Peter Böger ... (ed.)
264		1	\|a Berlin ; Heidelberg ; New York ; Barcelona ; Hong Kong ; London \|b Springer \|c 2002
300			\|a XXI, 364 S. \|b Ill., graph. Darst. : 24 cm
336			\|b txt \|2 rdacontent
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500			\|a Literaturangaben
650		4	\|a Cultures résistantes aux herbicides
650		4	\|a Herbicides
650		4	\|a Herbicide-resistant crops
650		4	\|a Herbicides
650	0	7	\|a Herbizid \|0 (DE-588)4113887-9 \|2 gnd \|9 rswk-swf
650	0	7	\|a Klassifikation \|0 (DE-588)4030958-7 \|2 gnd \|9 rswk-swf
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700	1		\|a Böger, Peter \|d 1935-2015 \|e Sonstige \|0 (DE-588)120378760 \|4 oth
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999			\|a oai:aleph.bib-bvb.de:BVB01-009852320

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adam_text	1 ACETOLACTATE SYNTHASE INHIBITORS T SUTOMU S HIMIZU ,I SHIZUE N AKAYAMA ,K OZO N AGAYAMA , T AKESHIGE M IYAZAWA , AND Y UKIO N EZU 1.1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 1.2 ACETOLACTATE SYNTHASE-INHIBITING HERBICIDES ACTIVELY DEVELOPED IN THE LATE 1990S . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2 1.3 DISCOVERY OF PYRIMIDINYL CARBOXY HERBICIDES (PYRIMIDINYLSALICYLATE CLASS HERBICIDES) . . . . . . . . . . . . . . . . . . 5 1.3.1 DISCOVERY OF THE LEAD STRUCTURES . . . . . . . . . . . . . . . . . . . . 5 1.3.2 DISCOVERY AND OPTIMIZATIONS OF THE SECONDARY LEAD STRUCTURE. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7 1.3.3 FURTHER OPTIMIZATIONS OF THE PYRIMIDINYL CARBOXY HERBICIDES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9 1.4 HERBICIDAL ACTIVITY OF PYRIMIDINYL CARBOXY HERBICIDES . . . . . . 10 1.4.1 PYRITHIOBAC-SODIUM FOR USE IN COTTON . . . . . . . . . . . . . . . 10 1.4.2 BISPYRIBAC-SODIUM FOR USE IN RICE . . . . . . . . . . . . . . . . . . 10 1.4.3 BISPYRIBAC-SODIUM FOR VEGETATION MANAGEMENT . . . . . . . . 11 1.4.4 PYRIMINOBAC-METHYL FOR USE IN RICE . . . . . . . . . . . . . . . . . 11 1.5 PHYSIOLOGICAL PLANT RESPONSE TO PYRIMIDINYL CARBOXY HERBICIDES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12 1.6 MODE OF ACTION AND SELECTIVITY OF PYRIMIDINYL CARBOXY HERBICIDES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13 1.6.1 PRIMARY TARGET . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13 1.6.2 INHIBITION OF BACTERIAL ACETOLACTATE SYNTHASE . . . . . . . . . . 14 1.6.3 SELECTIVITY . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15 1.7 BIOLOGICAL CHARACTERISTICS OF THE TARGET ENZYME . . . . . . . . . . . . 16 1.7.1 KINETIC STUDIES OF PLANT ACETOLACTATE SYNTHASE . . . . . . . . . 16 1.7.2 SUBUNIT COMPOSITIONS OF PLANT ACETOLACTATE SYNTHASE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17 1.7.3 RECOMBINANT SYSTEMS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 18 1.8 INHIBITION MECHANISM OF THE TARGET ENZYME BY PYRIMIDINYL CARBOXY HERBICIDES. . . . . . . . . . . . . . . . . . . . . . . 19 1.8.1 INHIBITION KINETICS WITH PLANT ACETOLACTATE SYNTHASE . . . . 19 1.8.2 INHIBITION KINETICS WITH BACTERIAL ACETOLACTATE SYNTHASE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22 CONTENTS X CONTENTS 1.9 MOLECULAR GENETICS OF TARGET ENZYME . . . . . . . . . . . . . . . . . . . . 22 1.9.1 ACETOLACTATE SYNTHASE GENES OF PLANTS . . . . . . . . . . . . . . . . 22 1.9.2 ACETOLACTATE SYNTHASE-INHIBITING HERBICIDE-RESISTANT CROPS (INCLUDING ARABIDOPSIS THALIANA ) AND THEIR ACETOLACTATE SYNTHASE GENES . . . . . . . . . . . . . . . . . . . . . . . 24 1.9.3 ACETOLACTATE SYNTHASE-INHIBITING HERBICIDE-RESISTANT WEEDS AND THEIR ACETOLACTATE SYNTHASE GENES . . . . . . . . . 28 1.9.4 GENETIC ENGINEERING . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31 REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 32 2 BLEACHING HERBICIDES: ACTION MECHANISM IN CAROTENOID BIOSYNTHESIS, STRUCTURAL REQUIREMENTS AND ENGINEERING OF RESISTANCE G ERHARD S ANDMANN 2.1 HERBICIDAL EFFECT AND MODE OF ACTION . . . . . . . . . . . . . . . . . . . . 43 2.2 INTERACTION OF INHIBITORS WITH CAROTENE DESATURATION . . . . . . . . 44 2.3 STRUCTURAL REQUIREMENTS FOR AN INHIBITOR OF PHYTOENE DESATURASE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 47 2.4 STRATEGIES FOR GENETIC ENGINEERING OF HERBICIDE RESISTANCE BY MODIFICATION OF THE CAROTENOGENIC PATHWAY . . . . . . . . . . . . . 50 2.4.1 OVEREXPRESSION OF A SUSCEPTIBLE LYCOPENE CYCLASE IN SYNECHOCOCCUS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 50 2.4.2 SELECTION OF MUTANTS WITH RESISTANT PHYTOENE DESATURASE AND GENE TRANSFER INTO TOBACCO . . . . . . . . . . . 51 2.4.3 NATURALLY RESISTANT PHYTOENE DESATURASE FROM BACTERIA AND GENETIC ENGINEERING OF A RESISTANT TOBACCO. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 52 2.5 CONCLUSION AND PERSPECTIVES . . . . . . . . . . . . . . . . . . . . . . . . . . . . 54 REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55 3 INHIBITORS OF AROMATIC AMINO ACID BIOSYNTHESIS (GLYPHOSATE) D ONALD R. G EIGER AND M ARK A. F UCHS 3.1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59 3.2 SYMPTOMS OF HERBICIDAL ACTIVITY . . . . . . . . . . . . . . . . . . . . . . . . 60 3.3 MODE OF ACTION OF GLYPHOSATE . . . . . . . . . . . . . . . . . . . . . . . . . . 62 3.3.1 OVERVIEW OF THE MODE OF ACTION . . . . . . . . . . . . . . . . . . . . 62 3.3.2 PRIMARY MODE OF ACTION . . . . . . . . . . . . . . . . . . . . . . . . . . 64 3.3.2.1 BIOCHEMICAL CHARACTERISTICS OF THE TARGET ENZYME . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64 3.3.2.2 STRUCTURAL CHARACTERISTICS OF THE TARGET ENZYME . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 65 3.3.2.3 INTERACTION BETWEEN 5-ENOLPYRUVYLSHIKIMATE 3-PHOSPHATE SYNTHASE AND GLYPHOSATE . . . . . . . . . 66 3.3.2.4 MOLECULAR REQUIREMENTS FOR HERBICIDAL ACTIVITY OF GLYPHOSATE . . . . . . . . . . . . . . . . . . . . . . 69 CONTENTS XI 3.3.3 SECONDARY PHYSIOLOGICAL CONSEQUENCES OF INHIBITION OF 5-ENOLPYRUVYLSHIKIMATE 3-PHOSPHATE SYNTHASE . . . . . . 70 3.3.3.1 INHIBITION OF CHORISMATE SYNTHESIS . . . . . . . . . . . . 70 3.3.3.2 DEPLETION OF PHOTOSYNTHETIC CARBON REDUCTION CYCLE INTERMEDIATE METABOLITES . . . . . . 71 3.3.3.3 DEVELOPMENT OF SECONDARY DAMAGE SYMPTOMS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 72 3.3.3.4 BASES OF DEVELOPMENT OF LETHAL SYMPTOMS AMONG SPECIES . . . . . . . . . . . . . . . . . . . . . . . . . . . 72 3.4 MECHANISMS FOR RESISTANCE AND TOLERANCE TO GLYPHOSATE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75 3.4.1 DEVELOPMENT OF COMMERCIALLY VALUABLE GLYPHOSATE- RESISTANT PLANTS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75 3.4.2 TOLERANCE TO FIELD DOSES OF GLYPHOSATE IN FIELD-GROWN PLANTS . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77 3.5 SUMMARY . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 79 REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 80 4 INHIBITORS OF GLUTAMINE SYNTHETASE G UENTER D ONN AND H ELMUT K OECHER 4.1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 87 4.2 PLANT GLUTAMINE SYNTHETASE ISOFORMS AND THEIR FUNCTION . . . . 87 4.3 GLUTAMINE SYNTHETASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . 90 4.4 DISCOVERY OF THE HERBICIDAL ACTIVITY OF PHOSPHINOTHRICIN AND BIALAPHOS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 91 4.5 MODE OF GLUTAMINE SYNTHETASE INHIBITION . . . . . . . . . . . . . . . . . 92 4.6 EFFECTS OF GLUTAMINE SYNTHETASE INHIBITORS IN PLANTS . . . . . . . . . 94 4.6.1 VISIBLE SYMPTOMS OF HERBICIDAL ACTION . . . . . . . . . . . . . . 94 4.6.2 PHYSIOLOGICAL EFFECTS OF GLUTAMINE SYNTHETASE INHIBITION IN PLANTS BY PHOSPHINOTHRICIN . . . . . . . . . . . . . 94 4.7 ATTEMPTS TO GENERATE SELECTIVITY FOR GLUFOSINATE . . . . . . . . . . . . 96 4.7.1 ATTEMPTS TO SELECT GLUFOSINATE TOLERANT MUTANTS . . . . . . . 97 4.7.2 METABOLIC INACTIVATION OF GLUFOSINATE BY BAR AND PAT ENZYMES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 98 REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 99 5 ACETYL-COA CARBOXYLASE INHIBITORS M ALCOLM D. D EVINE 5.1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 103 5.2 SYMPTOMS OF HERBICIDAL ACTIVITY . . . . . . . . . . . . . . . . . . . . . . . . 103 5.3 BIOCHEMICAL CHARACTERISTICS OF THE TARGET ENZYME . . . . . . . . . . 104 5.4 MODE OF ACTION OF CYCLOHEXANEDIONE AND ARYLOXYPHENOXYPROPANOATE HERBICIDES . . . . . . . . . . . . . . . . 105 5.5 ASSAYS FOR ACETYL-COA CARBOXYLASE ACTIVITY . . . . . . . . . . . . . . . 106 5.6 MOLECULAR GENETICS OF RESISTANCE TO ACETYL-COA CARBOXYLASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 107 REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 110 6 INHIBITORS OF BIOSYNTHESIS OF VERY-LONG-CHAIN FATTY ACIDS P ETER B OEGER AND B ERND M ATTHES 6.1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 115 6.2 THE MODEL SYSTEM . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 119 6.3 VERY LONG-CHAIN FATTY ACID BIOSYNTHESIS INHIBITION IN INTACT LEAVES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 123 6.4 THE CELL-FREE ELONGASE SYSTEM . . . . . . . . . . . . . . . . . . . . . . . . . . 127 6.5 ASSUMPTIONS OF THE REACTION MECHANISM . . . . . . . . . . . . . . . . . 131 6.6 CONSIDERATIONS ON RESISTANCE . . . . . . . . . . . . . . . . . . . . . . . . . . . 133 REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 135 7 CELLULOSE BIOSYNTHESIS INHIBITOR HERBICIDES K EVIN C. V AUGHN 7.1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 139 7.2 MODE OF ACTION STUDIES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 140 7.2.1 CELL PLATES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 140 7.2.2 DEVELOPING COTTON FIBERS . . . . . . . . . . . . . . . . . . . . . . . . . 142 7.2.3 AZIDO-DICHLOBENIL DERIVATIVES . . . . . . . . . . . . . . . . . . . . . . 144 7.3 RESISTANT BIOTYPES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 145 7.4 HABITUATION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 146 7.5 THE UNUSUAL CASE OF QUINCLORAC . . . . . . . . . . . . . . . . . . . . . . . . . 148 7.6 CONSPECTUS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 148 REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 148 8 INHIBITORS OF PROTOPORPHYRINOGEN OXIDASE: A BRIEF UPDATE H IROSHI M ATSUMOTO 8.1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 151 8.2 PROTOPORPHYRINOGEN OXIDASE INHIBITORS AND THEIR MODE OF ACTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 152 8.3 BIOCHEMICAL CHARACTERIZATION OF PROTOPORPHYRINOGEN OXIDASE . . . . . . . . . . . . . . . . . . . . . . . . . 154 8.4 PROTOPORPHYRINOGEN OXIDASE GENES AND TRANSGENIC HERBICIDE-RESISTANT PLANTS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 154 8.5 RECENT ADVANCES IN QSAR STUDIES . . . . . . . . . . . . . . . . . . . . . . . 156 8.6 ANTIOXIDATIVE STRESS RESPONSES OF PLANTS TO PROTOPORPHYRINOGEN OXIDASE INHIBITORS . . . . . . . . . . . . . . . . . 157 REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 158 XII CONTENTS 9 GENETIC ENGINEERING OF HERBICIDE-RESISTANT PLANTS M AMORU H ORIKOSHI 9.1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 163 9.2 STRATEGY . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 164 9.2.1 THE GENE ENCODING THE HERBICIDE-INACTIVATING ENZYME . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 164 9.2.2 MUTANT OR FOREIGN GENE ENCODING THE TARGET ENZYME WITH LOW AFFINITY TO THE HERBICIDE . . . . . . . . . . . 165 9.3 CLONING OF THE GENES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 166 9.3.1 GENETIC RESOURCE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 166 9.3.1.1 MICROORGANISM . . . . . . . . . . . . . . . . . . . . . . . . . . . 167 9.3.1.2 PLANT TISSUE CULTURE . . . . . . . . . . . . . . . . . . . . . . . . 167 9.3.1.3 MUTANT PLANTS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 168 9.3.2 CLONING METHODS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 168 9.3.2.1 THE INFORMATION OF PROTEIN . . . . . . . . . . . . . . . . . . 168 9.3.2.2 THE INFORMATION OF NUCLEIC ACID . . . . . . . . . . . . . 169 9.3.2.3 BACTERIAL GENETICS . . . . . . . . . . . . . . . . . . . . . . . . . 169 9.4 GENE TRANSFER . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 169 9.4.1 PEG-MEDIATED GENE TRANSFER AND ELECTROPORATION . . . . . . 170 9.4.2 PARTICLE BOMBARDMENT . . . . . . . . . . . . . . . . . . . . . . . . . . . . 170 9.4.3 AGROBACTERIUM -MEDIATED GENE TRANSFER . . . . . . . . . . . . . . 170 9.5 VECTOR CONSTRUCTS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 171 9.5.1 EXPRESSION CASSETTES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 171 9.5.1.1 PROMOTER AND TERMINATOR . . . . . . . . . . . . . . . . . . . 171 9.5.1.2 SELECTION MARKER GENE . . . . . . . . . . . . . . . . . . . . . 172 9.5.1.3 ENHANCER SEQUENCE . . . . . . . . . . . . . . . . . . . . . . . . 172 9.5.1.4 TRANSIT PEPTIDE SEQUENCE . . . . . . . . . . . . . . . . . . . . 172 9.5.2 TYPE OF VECTORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 172 9.5.2.1 VECTOR FOR DIRECT GENE TRANSFER . . . . . . . . . . . . . . 172 9.5.2.2 VECTORS FOR AGROBACTERIUM -MEDIATED GENE TRANSFER . . . . . . . . . . . . . . . . . . . . . . . . . . . . 173 9.5.2.3 OTHER VECTORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 173 9.6 CONCLUSIONS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 173 REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 174 10 MAJOR SYNTHETIC ROUTES FOR MODERN HERBICIDE CLASSES AND AGROCHEMICAL CHARACTERISTICS K ENJI H IRAI ,A TSUSHI U CHIDA , AND R YUTA O HNO 10.1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 179 10.2 ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . 179 10.2.1 SULFONYLUREA ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . 180 10.2.1.1 PRACTICAL SULFONYLUREA ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . 180 CONTENTS XIII 10.2.1.2 STRUCTURAL EVOLUTION OF SULFONYLUREA ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . 186 10.2.1.3 MAJOR SYNTHETIC ROUTES FOR SULFONYLUREAS . . . . 193 10.2.2 TRIAZOLINONE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . 196 10.2.2.1 PRACTICAL TRIAZOLINONE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . 196 10.2.2.2 STRUCTURAL EVOLUTION OF TRIAZOLINONE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . 197 10.2.2.3 MAJOR SYNTHETIC ROUTES FOR TRIAZOLINONE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . 197 10.2.3 TRIAZOLOPYRIMIDINE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 197 10.2.3.1 PRACTICAL TRIAZOLOPYRIMIDINE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . 199 10.2.3.2 STRUCTURAL EVOLUTION OF TRIAZOLOPYRIMIDINE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . 201 10.2.3.3 MAJOR SYNTHETIC ROUTES FOR TRIAZOLOPYRIMIDINE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . 202 10.2.4 ACETOLACTATE SYNTHASE INHIBITOR-LIKE MISCELLANEOUS PYRIMIDINES AND RELATED COMPOUNDS . . . . . . . . . . . . . . 202 10.2.5 PYRIMIDYL(THIO)OXYBENZOATE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 202 10.2.5.1 PRACTICAL PYRIMIDYL(THIO)OXYBENZOATE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . 202 10.2.5.2 STRUCTURAL EVOLUTION OF PYRIMIDYL(THIO)OXYBENZOATE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . 204 10.2.5.3 MAJOR SYNTHETIC ROUTES FOR PYRIMIDYL(THIO)OXYBENZOATE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . 209 10.2.6 IMIDAZOLINONE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . 210 10.2.6.1 PRACTICAL IMIDAZOLINONE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . 210 10.2.6.2 STRUCTURAL EVOLUTION OF IMIDAZOLINONE ALS INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . 212 10.2.6.3 MAJOR SYNTHETIC ROUTES FOR IMIDAZOLINONE ACETOLACTATE SYNTHASE INHIBITORS . . . . . . . . . . . 212 10.3 CAROTENOGENESIS INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . 213 10.3.1 PHYTOENE DESATURASE INHIBITORS . . . . . . . . . . . . . . . . . . . 213 10.3.1.1 PRACTICAL PHYTOENE DESATURASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 213 10.3.1.2 STRUCTURAL EVOLUTION OF PHYTOENE DESATURASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 216 XIV CONTENTS 10.3.1.3 MAJOR SYNTHETIC ROUTES FOR PHYTOENE DESATURASE INHIBITORS . . . . . . . . . . . . . . . . . . . . 218 10.3.2 4-HYDROXYPHENYLPYRUVATE DIOXYGENASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 221 10.3.2.1 PRACTICAL 4-HYDROXYPHENYLPYRUVATE DIOXYGENASE INHIBITORS . . . . . . . . . . . . . . . . . . 221 10.3.2.2 STRUCTURAL EVOLUTION OF 4-HYDROXYPHENYLPYRUVATE DIOXYGENASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 223 10.3.2.3 MAJOR SYNTHETIC ROUTES FOR 4-HYDROXYPHENYLPYRUVATE DIOXYGENASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 229 10.3.3 OTHER CAROTENOGENESIS INHIBITORS . . . . . . . . . . . . . . . . . 229 10.4 AROMATIC AMINO ACID BIOSYNTHESIS INHIBITORS . . . . . . . . . . . . . 232 10.5 GLUTAMINE SYNTHETASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . 234 10.6 ACETYL COA CARBOXYLASE (ACCASE) INHIBITORS . . . . . . . . . . . . . 234 10.6.1 PRACTICAL ACETYL COA CARBOXYLASE INHIBITORS . . . . . . . . 235 10.6.2 STRUCTURAL EVOLUTION OF ACETYL COA CARBOXYLASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 238 10.6.3 MAJOR SYNTHETIC ROUTES FOR ACETYL COA CARBOXYLASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . 238 10.7 VERY LONG-CHAIN FATTY ACIDS BIOSYNTHESIS INHIBITORS . . . . . . . . 243 10.7.1 PRACTICAL CHLOROACETAMIDE VERY LONG-CHAIN FATTY ACIDS BIOSYNTHESIS INHIBITORS . . . . . . . . . . . . . . . . . . . . . 244 10.7.2 OTHER VERY LONG-CHAIN FATTY ACIDS BIOSYNTHESIS INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 246 10.8 CELLULOSE BIOSYNTHESIS INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . 249 10.8.1 PRACTICAL CELLULOSE BIOSYNTHESIS INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 249 10.8.2 STRUCTURAL EVOLUTION OF CELLULOSE BIOSYNTHESIS INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 253 10.8.3 MAJOR SYNTHETIC ROUTES FOR CELLULOSE BIOSYNTHESIS INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . 253 10.9 PROTOPORPHYRINOGEN-IX OXIDASE INHIBITORS. . . . . . . . . . . . . . . . 255 10.9.1 HETEROCYCLE PROTOPORPHYRINOGEN-IX OXIDASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 256 10.9.1.1 FIRST-GENERATION HETEROCYCLE PROTOPORPHYRINOGEN-IX OXIDASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 259 10.9.1.2 SECOND-GENERATION HETEROCYCLE PROTOPORPHYRINOGEN-IX OXIDASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 260 10.9.2 STRUCTURAL EVOLUTION OF PROTOPORPHYRINOGEN-IX OXIDASE INHIBITORS SINCE 1995 . . . . . . . . . . . . . . . . . . . . 262 CONTENTS XV 10.9.2.1 STRUCTURAL EVOLUTION OF FIRST-GENERATION HETEROCYCLE PROTOPORPHYRINOGEN-IX OXIDASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . 263 10.9.2.2 STRUCTURAL EVOLUTION OF SECOND-GENERATION HETEROCYCLE PROTOPORPHYRINOGEN-IX OXIDASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 263 10.9.2.3 NEXT-GENERATION HETEROCYCLE PROTOPORPHYRINOGEN-IX OXIDASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 271 10.9.3 MAJOR SYNTHETIC ROUTES FOR PROTOPORPHYRINOGEN-IX OXIDASE INHIBITORS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 274 10.10 NOTES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 278 PATENT LITERATURE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 280 11 DIVERSE RESPONSE OF PLANTS TOWARDS CHIRAL PHYTOTOXIC CHEMICALS H IROYOSHI O MOKAWA 11.1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 291 11.2 DIVERSE RESPONSE OF OPTICALLY ACTIVE HERBICIDES . . . . . . . . . . . 292 11.2.1 QUALITATIVELY SIMILAR ENANTIOSELECTIVE ACTION . . . . . . . . 294 11.2.2 ENANTIOMERIC METABOLISM . . . . . . . . . . . . . . . . . . . . . . . 295 11.2.3 CHIRAL INVERSION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 296 11.3 DIVERSE RESPONSE OF PLANTS THROUGH CHIRALITY . . . . . . . . . . . . . 297 11.3.1 CHIRAL S -TRIAZINES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 298 11.3.1.1 LIGHT-DEPENDENT AND LIGHT-INDEPENDENT GROWTH INHIBITION . . . . . . . . . . . . . . . . . . . . . . 298 11.3.1.2 CYTOKININ-LIKE ACTIVITY . . . . . . . . . . . . . . . . . . 300 11.3.2 CHIRAL UREAS. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 302 11.3.2.1 ENANTIOSELECTIVE PHYTOTOXICITY . . . . . . . . . . . . . 302 11.3.2.2 STRESS-RELIEVING ACTIVITY . . . . . . . . . . . . . . . . . 304 11.3.2.3 CROSS INTERGENUS SELECTIVE PHYTOTOXICITY AMONG GRAMINEAE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 306 11.4 CHIRALITY AND ACTIVITY RELATIONSHIP . . . . . . . . . . . . . . . . . . . . . . 307 11.4.1 BINDING DIRECTION OF S -TRIAZINES AT THE PHOTOSYSTEM II REACTION CENTER . . . . . . . . . . . . . 308 11.4.2 EUDISMIC ANALYSIS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 311 11.4.2.1 PHOTOSYSTEM II INHIBITION . . . . . . . . . . . . . . . . 311 11.4.2.2 LIGHT-INDEPENDENT INHIBITION . . . . . . . . . . . . . 313 11.4.2.3 STRESS RELIEF . . . . . . . . . . . . . . . . . . . . . . . . . . . 313 REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 314 XVI CONTENTS 12 TRANSCUTICULAR PENETRATION OF FOLIAR-APPLIED PESTICIDES * ITS ANALYSIS BY A LOGISTIC-KINETIC PENETRATION MODEL T ADAKAZU W ATANABE 12.1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 319 12.2 OVERVIEW . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 320 12.3 LOGISTIC-KINETIC TRANSCUTICULAR PENETRATION MODEL OF FOLIAR-APPLIED PESTICIDES . . . . . . . . . . . . . . . . . . . . . . . . . . . 323 12.3.1 SCENARIO . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 323 12.3.2 TRANSCUTICULAR PENETRATION-MEASURING CELL . . . . . . . . . 326 12.4 PARAMETERS AND FACTORS GOVERNING TRANSCUTICULAR PENETRATION KINETICS OF FOLIAR-APPLIED PESTICIDES . . . . . . . . . . 327 12.4.1 ADAPTABILITY OF THE LOGISTIC-KINETIC PENETRATION MODEL . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 327 12.4.2 FACTORS INFLUENCING TRANSCUTICULAR PENETRATION KINETICS . . . . . . . . . . . . . . . . . . . . . . . . . . . . 328 12.4.3 EFFECT OF MOLECULAR PARAMETERS OF PESTICIDES ON TRANSCUTICULAR PENETRATION KINETICS . . . . . . . . . . . . . 328 12.5 EFFECTS OF ADJUVANTS ON TRANSCUTICULAR PENETRATION KINETICS OF FOLIAR-APPLIED PESTICIDES . . . . . . . . . . . . . . . . . . . . 330 12.5.1 ANALYSIS OF ADJUVANT ACTION (ADJUVANCY) . . . . . . . . . . . 330 12.5.2 EFFECT OF TRITON SURFACTANTS . . . . . . . . . . . . . . . . . . . . . . 331 12.5.3 EFFECT OF EMULSIFIABLE OILS . . . . . . . . . . . . . . . . . . . . . . . 332 12.5.4 EFFECT OF HUMECTANTS . . . . . . . . . . . . . . . . . . . . . . . . . . . 332 12.5.5 EFFECT OF AMINE SURFACTANTS ON GLYPHOSATE PENETRATION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 333 12.6 DISCUSSION AND CONCLUSIONS . . . . . . . . . . . . . . . . . . . . . . . . . . . 334 REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 337 13 STRUCTURE-ACTIVITY CORRELATION OF VERY LONG-CHAIN FATTY ACID BIOSYNTHESIS INHIBITORS K O W AKABAYASHI AND P ETER B OEGER 13.1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 341 13.2 VERY LONG-CHAIN FATTY ACID BIOSYNTHESIS INHIBITION BY HERBICIDES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 341 13.3 VERY LONG-CHAIN FATTY ACID BIOSYNTHESIS INHIBITION BY THENYLCHLOR AND ITS ANALOGS . . . . . . . . . . . . . . . . . . . . . . . . 345 13.4 ACTION OF CAFENSTROLE AND ITS ANALOGS . . . . . . . . . . . . . . . . . . . 349 13.5 ACTION OF INDANOFAN AND ITS ANALOGS . . . . . . . . . . . . . . . . . . . . 351 13.6 OUTLOOK . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 353 REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 356 INDEX . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 359 CONTENTS XVII
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publisher	Springer
record_format	marc
spelling	Herbicide classes in development mode of action, targets, genetic engineering, chemistry Peter Böger ... (ed.) Berlin ; Heidelberg ; New York ; Barcelona ; Hong Kong ; London Springer 2002 XXI, 364 S. Ill., graph. Darst. : 24 cm txt rdacontent n rdamedia nc rdacarrier Literaturangaben Cultures résistantes aux herbicides Herbicides Herbicide-resistant crops Herbizid (DE-588)4113887-9 gnd rswk-swf Klassifikation (DE-588)4030958-7 gnd rswk-swf Herbizid (DE-588)4113887-9 s DE-604 Klassifikation (DE-588)4030958-7 s Böger, Peter 1935-2015 Sonstige (DE-588)120378760 oth SWB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009852320&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis
spellingShingle	Herbicide classes in development mode of action, targets, genetic engineering, chemistry Cultures résistantes aux herbicides Herbicides Herbicide-resistant crops Herbizid (DE-588)4113887-9 gnd Klassifikation (DE-588)4030958-7 gnd
subject_GND	(DE-588)4113887-9 (DE-588)4030958-7
title	Herbicide classes in development mode of action, targets, genetic engineering, chemistry
title_auth	Herbicide classes in development mode of action, targets, genetic engineering, chemistry
title_exact_search	Herbicide classes in development mode of action, targets, genetic engineering, chemistry
title_full	Herbicide classes in development mode of action, targets, genetic engineering, chemistry Peter Böger ... (ed.)
title_fullStr	Herbicide classes in development mode of action, targets, genetic engineering, chemistry Peter Böger ... (ed.)
title_full_unstemmed	Herbicide classes in development mode of action, targets, genetic engineering, chemistry Peter Böger ... (ed.)
title_short	Herbicide classes in development
title_sort	herbicide classes in development mode of action targets genetic engineering chemistry
title_sub	mode of action, targets, genetic engineering, chemistry
topic	Cultures résistantes aux herbicides Herbicides Herbicide-resistant crops Herbizid (DE-588)4113887-9 gnd Klassifikation (DE-588)4030958-7 gnd
topic_facet	Cultures résistantes aux herbicides Herbicides Herbicide-resistant crops Herbizid Klassifikation
url	http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009852320&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA
work_keys_str_mv	AT bogerpeter herbicideclassesindevelopmentmodeofactiontargetsgeneticengineeringchemistry

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