Modern Crop Protection Compounds, Volume 1
portes grátis
Modern Crop Protection Compounds, Volume 1
Herbicides
Jeschke, Peter; Lorsbach, Beth; Lamberth, Clemens
Wiley-VCH Verlag GmbH
04/2026
720
Dura
Inglês
9783527352708
Pré-lançamento - envio 15 a 20 dias após a sua edição
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Volume 1
Preface to the Fourth Edition xxxi
Part I Herbicides 1
Overview 3
Beth Lorsbach
1 Herbicide Resistance Action Committee (HRAC): Herbicide Classification, Resistance Evolution, Survey, and Resistance Mitigation Activities 5
Roland Beffa, Hubert Menne, and Helmut Koecher
1.1 Introduction 5
1.2 HRAC Herbicide Classification System 7
1.3 Herbicide Resistance Survey 9
2 Acetohydroxyacid Synthase Structure and Inhibitors (AHAS/ALS) 31
2.1 Biochemistry, Structure, Regulation, Mechanism, Inhibition of the Target, and Resistance 31
Ryan P. Emptage and Steven Gutteridge
2.2 Newer Sulfonylureas 50
Oswald Ort and David M. Barber
2.3 Imidazolinone Herbicides 90
Dale L. Shaner, Mark Stidham, Bijay Singh, and Siyuan Tan
2.4 Triazolopyrimidines 101
Timothy C. Johnson, Richard K. Mann, Paul R. Schmitzer, Roger E. Gast, and Gerrit J. de Boer
2.5 Triazolopyrmidine Addendum 119
Paul R. Schmitzer and Jossian Oppenheimer
2.6 Pyrimidinyl Carboxylates and Sulfonanilides 124
Atsushi Shibayama, Osamu Watanabe, and Tsutomu Shimizu
2.7 Sulfonylaminocarbonyl-Triazolinones 150
Klaus-Helmut Mueller, Hans-Joachim Santel, Ernst Rudolf F. Gesing, and Gilbert Besong
3 Protoporphyrinogen IX Oxidase Inhibitors 175
3.1 Protoporphyrinogen IX Oxidase Inhibitors 175
Tobias Seiser, Jared Bell, Dustin Lewis, Cyrill Zagar, Rex Liebl, George Theodoridis, and Matthias Witschel
3.2 The PPO Target Site, Resistance Evolution, and Herbicide Tolerance Trait Discovery 215
Jared Bell, Aimone Porri, and Carla Yerkes
4 Herbicides with Bleaching Properties 247
4.1 Phytoene Desaturase Inhibitors 247
Matthias Witschel and Gerhard Hamprecht
4.2 Hydroxyphenylpyruvate Dioxygenase (HPPD): The Herbicide Target 272
John P. Evans and Timothy R. Hawkes
4.3 Triketones 283
Andrew J.F. Edmunds and James A. Morris
4.4 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Inhibitors: Heterocycles 314
Andreas van Almsick and Paul M. Burton
5 New Auxin Mimics and Herbicides 337
5.1 The Molecular Mode of Action of Auxin Herbicides 337
Jared L. Bell, Paul R. Schmitzer, and Hudson Takano
5.2 New Auxin Mimic Herbicides: Aminopyralid 352
Jeffrey B. Epp, Roger E. Gast, Jeff A. Nelson, and William C. Lo
5.3 Pyrimidine Carboxylic Acids: Aminocyclopyrachlor 361
Hansjoerg Kraehmer, Harry J. Strek, Jon S. Claus, David M. Barber, and Bruce L. Finkelstein
5.4 6-Arylpicolinates: Halauxifen-Methyl and Florpyrauxifen-Benzyl 378
Roger E. Gast, Mauricio Morell, Monte R. Weimer, and Paul R. Schmitzer
6 Herbicides Disturbing the Synthesis of Very-Long-Chain Fatty Acids 385
6.1 Inhibitors of the Synthesis of Very-Long-Chain Fatty Acids (VLCFAs) 385
Rebecka Duecker, Hansjoerg Kraehmer, Peter Babczinski, and Roland Beffa
6.2 Chemistry and Biology of Oxyacetamides, Tetrazolinones, and Triazolinones 398
Hansjoerg Kraehmer and Roland Beffa
6.3 Isoxazolines 408
Masao Nakatani, Masaru Shibata, Atsushi Sato, Hisashi Honda, Yoshitaka Tanetani, Kiyoshi Kawai, Ryo Hanai, Takumi Yoshimura, and Tsutomu Shimizu
7 Inhibitors of Cellulose Biosynthesis 421
Bernd Laber and Hansjoerg Dietrich
7.1 Introduction 421
7.2 Cellulose Biosynthesis 421
7.3 Cellulose Biosynthesis Inhibitors from Different Chemical Classes 426
7.4 Cellulose Biosynthesis Inhibitors from Natural Sources 451
8 Safeners for Herbicides 463
Graham Collier, Beth Lorsbach, Chris Rosinger, and Wolfgang Schulte
8.1 Introduction 463
8.2 Overview of Selected Safeners 467
8.3 Mechanisms of Herbicide Safener Action 475
8.4 Mode of Action of Safeners in Agricultural Practice 480
8.5 Concluding Remarks 485
9 Genetically Modified Herbicide Tolerant Crops 489
9.1 Genetically Modified Herbicide-Resistant Crops: A Future Beyond Glyphosate 489
Chandrima Shyam, Clayton T. Larue, Neha Rana, and Alejandro Perez-Jones
9.2 Glutamine Synthetase Inhibitors 505
Wolfgang Schulte and Clayton T. Larue
10 Microtubulin Assembly Inhibitors (Pyridines) 523
Joshua J. Roth, Jeffrey B. Epp, Darin W. Lickfeldt, Denise P. Cudworth, Daniel D. Loughner, and Lowell D. Markley
10.1 Introduction 523
10.2 Biology of the Microtubulin Assembly Inhibitors (Pyridines) 524
10.3 Environmental Fate of Microtubulin Assembly Inhibitors (Pyridines) 525
10.4 Toxicology of Microtubulin Assembly Inhibitors (Pyridines) 526
10.5 Mode of Action of Microtubulin Assembly Inhibitors (Pyridines) 526
10.6 Synthesis of Dithiopyr and Thiazopyr 527
11 Acetyl-CoA Carboxylase Inhibitors 531
Yunas Bhonoah, Vikas Sikervar, Danielle Sayer, Jean Wenger, Thierry Niderman, Chris Mathews, Steve Wailes, and Christopher M. Baker
11.1 Introduction 531
11.2 Biochemistry and Mode of Action 531
11.3 Commercialized ACCase Inhibitors 535
11.4 The Need for New ACCase-Inhibiting Herbicides 541
11.5 The Challenge of Bringing New ACCase Compounds to Market 542
11.6 New Approaches in ACCase Chemistry 545
11.7 Summary and Conclusions 551
12 Homogentisate Solanesyltransferase (HST) Inhibitors: Cyclopyrimorate 559
Mamiko Shino, Takahiro Hamada, and Shinichi Banba
12.1 Introduction 559
12.2 Discover of Cyclopyrimorate 559
12.3 Mode of Action of Cyclopyrimorate 561
12.4 Biological Spectrum and Activity of Cyclopyrimorate 567
12.5 Other HST Inhibitors 568
12.6 Summary and Conclusions 568
13 Solanesyl Diphosphate Synthase Inhibitors: Aclonifen 571
Gudrun Lange, Mohan Padmanaban, and Bernd Laber
13.1 Introduction 571
13.2 Synthesis of Aclonifen 571
13.3 Elucidation of the Aclonifen Site of Action 572
13.4 Mechanism of Solanesyl Diphosphate Synthase Inhibition 574
13.5 Molecular Basis of Aclonifen Binding to Solanesyl Diphosphate Synthase 575
13.6 Species and Isoform Selectivity 577
13.7 Solanesyl Diphosphate Synthase Inhibitors: Recent Developments 579
14 Inhibitors of the Deoxy-D-Xylulose Phosphate Synthase (DOXP Synthase) 589
Saptarshi De, Ryan Emptage, and Il-Ho Kang
14.1 Introduction 589
14.2 Mode of Action 589
14.3 Chemical Synthesis 592
14.4 Clomazone 593
14.5 Bixlozone 595
14.6 Other Known Isoxazolidinone Herbicides 595
14.7 Summary 598
15 Fatty Acid Thioesterase Inhibitors 603
Matthias Witschel
15.1 Introduction 603
15.2 Fatty Acid Thioesterases in Plants 603
15.3 Biochemical Validation of Fatty Acid Thioesterase Inhibition by Commercial Herbicides 604
15.4 Crystal Structure of Cinmethylin- and Cumyluron-Bound Fatty Acid Thioesterase A 605
15.5 Chemical Structure Types and Activities of Fatty Acid Thioesterase Inhibitors 606
15.6 Synthetic Routes for Fatty Acid Thioesterase Inhibitors 609
16 Validation of Dihydroorotate Dehydrogenase as a Herbicide Target: Discovery of Tetflupyrolimet 613
Thomas P. Selby, Alison M. Levens, IL-Ho Kang, Ryan P. Emptage, and John L. Andreassi
16.1 Introduction 613
16.2 Pyrimidine Biosynthesis Pathway 613
16.3 DHODH as an Agrochemical Target 615
16.4 Search for a New Mode of Action Herbicide 616
16.5 Conclusion 620
17 Photosynthesis Inhibitors: Regulatory Aspects, Reregistration in Europe, Market Trends, and New Products 623
Martyn Griffiths
17.1 Introduction 623
17.2 The Approval Process for Active Substances in the World and Especially the European Union 626
17.3 Main Changes in Guidelines Regarding EU Reapproval 631
17.4 New Regulations in Europe 638
17.5 Situation of PS II Inhibitors in the EU Markets 642
17.6 Current Market Share of PS II Compound Groups 643
17.7 A Relatively New Herbicide for Corn and Sugarcane: Amicarbazone 650
17.8 Conclusions 653
18 New Aspects of Plant Regulators 659
Hans Ulrich Haas
18.1 Introduction 659
18.2 Plant Growth Regulators 659
18.3 Plant Growth Regulators in Modern Agriculture 661
18.4 Conclusions and Developments 667
References 667
Index 671
Preface to the Fourth Edition xxxi
Part I Herbicides 1
Overview 3
Beth Lorsbach
1 Herbicide Resistance Action Committee (HRAC): Herbicide Classification, Resistance Evolution, Survey, and Resistance Mitigation Activities 5
Roland Beffa, Hubert Menne, and Helmut Koecher
1.1 Introduction 5
1.2 HRAC Herbicide Classification System 7
1.3 Herbicide Resistance Survey 9
2 Acetohydroxyacid Synthase Structure and Inhibitors (AHAS/ALS) 31
2.1 Biochemistry, Structure, Regulation, Mechanism, Inhibition of the Target, and Resistance 31
Ryan P. Emptage and Steven Gutteridge
2.2 Newer Sulfonylureas 50
Oswald Ort and David M. Barber
2.3 Imidazolinone Herbicides 90
Dale L. Shaner, Mark Stidham, Bijay Singh, and Siyuan Tan
2.4 Triazolopyrimidines 101
Timothy C. Johnson, Richard K. Mann, Paul R. Schmitzer, Roger E. Gast, and Gerrit J. de Boer
2.5 Triazolopyrmidine Addendum 119
Paul R. Schmitzer and Jossian Oppenheimer
2.6 Pyrimidinyl Carboxylates and Sulfonanilides 124
Atsushi Shibayama, Osamu Watanabe, and Tsutomu Shimizu
2.7 Sulfonylaminocarbonyl-Triazolinones 150
Klaus-Helmut Mueller, Hans-Joachim Santel, Ernst Rudolf F. Gesing, and Gilbert Besong
3 Protoporphyrinogen IX Oxidase Inhibitors 175
3.1 Protoporphyrinogen IX Oxidase Inhibitors 175
Tobias Seiser, Jared Bell, Dustin Lewis, Cyrill Zagar, Rex Liebl, George Theodoridis, and Matthias Witschel
3.2 The PPO Target Site, Resistance Evolution, and Herbicide Tolerance Trait Discovery 215
Jared Bell, Aimone Porri, and Carla Yerkes
4 Herbicides with Bleaching Properties 247
4.1 Phytoene Desaturase Inhibitors 247
Matthias Witschel and Gerhard Hamprecht
4.2 Hydroxyphenylpyruvate Dioxygenase (HPPD): The Herbicide Target 272
John P. Evans and Timothy R. Hawkes
4.3 Triketones 283
Andrew J.F. Edmunds and James A. Morris
4.4 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Inhibitors: Heterocycles 314
Andreas van Almsick and Paul M. Burton
5 New Auxin Mimics and Herbicides 337
5.1 The Molecular Mode of Action of Auxin Herbicides 337
Jared L. Bell, Paul R. Schmitzer, and Hudson Takano
5.2 New Auxin Mimic Herbicides: Aminopyralid 352
Jeffrey B. Epp, Roger E. Gast, Jeff A. Nelson, and William C. Lo
5.3 Pyrimidine Carboxylic Acids: Aminocyclopyrachlor 361
Hansjoerg Kraehmer, Harry J. Strek, Jon S. Claus, David M. Barber, and Bruce L. Finkelstein
5.4 6-Arylpicolinates: Halauxifen-Methyl and Florpyrauxifen-Benzyl 378
Roger E. Gast, Mauricio Morell, Monte R. Weimer, and Paul R. Schmitzer
6 Herbicides Disturbing the Synthesis of Very-Long-Chain Fatty Acids 385
6.1 Inhibitors of the Synthesis of Very-Long-Chain Fatty Acids (VLCFAs) 385
Rebecka Duecker, Hansjoerg Kraehmer, Peter Babczinski, and Roland Beffa
6.2 Chemistry and Biology of Oxyacetamides, Tetrazolinones, and Triazolinones 398
Hansjoerg Kraehmer and Roland Beffa
6.3 Isoxazolines 408
Masao Nakatani, Masaru Shibata, Atsushi Sato, Hisashi Honda, Yoshitaka Tanetani, Kiyoshi Kawai, Ryo Hanai, Takumi Yoshimura, and Tsutomu Shimizu
7 Inhibitors of Cellulose Biosynthesis 421
Bernd Laber and Hansjoerg Dietrich
7.1 Introduction 421
7.2 Cellulose Biosynthesis 421
7.3 Cellulose Biosynthesis Inhibitors from Different Chemical Classes 426
7.4 Cellulose Biosynthesis Inhibitors from Natural Sources 451
8 Safeners for Herbicides 463
Graham Collier, Beth Lorsbach, Chris Rosinger, and Wolfgang Schulte
8.1 Introduction 463
8.2 Overview of Selected Safeners 467
8.3 Mechanisms of Herbicide Safener Action 475
8.4 Mode of Action of Safeners in Agricultural Practice 480
8.5 Concluding Remarks 485
9 Genetically Modified Herbicide Tolerant Crops 489
9.1 Genetically Modified Herbicide-Resistant Crops: A Future Beyond Glyphosate 489
Chandrima Shyam, Clayton T. Larue, Neha Rana, and Alejandro Perez-Jones
9.2 Glutamine Synthetase Inhibitors 505
Wolfgang Schulte and Clayton T. Larue
10 Microtubulin Assembly Inhibitors (Pyridines) 523
Joshua J. Roth, Jeffrey B. Epp, Darin W. Lickfeldt, Denise P. Cudworth, Daniel D. Loughner, and Lowell D. Markley
10.1 Introduction 523
10.2 Biology of the Microtubulin Assembly Inhibitors (Pyridines) 524
10.3 Environmental Fate of Microtubulin Assembly Inhibitors (Pyridines) 525
10.4 Toxicology of Microtubulin Assembly Inhibitors (Pyridines) 526
10.5 Mode of Action of Microtubulin Assembly Inhibitors (Pyridines) 526
10.6 Synthesis of Dithiopyr and Thiazopyr 527
11 Acetyl-CoA Carboxylase Inhibitors 531
Yunas Bhonoah, Vikas Sikervar, Danielle Sayer, Jean Wenger, Thierry Niderman, Chris Mathews, Steve Wailes, and Christopher M. Baker
11.1 Introduction 531
11.2 Biochemistry and Mode of Action 531
11.3 Commercialized ACCase Inhibitors 535
11.4 The Need for New ACCase-Inhibiting Herbicides 541
11.5 The Challenge of Bringing New ACCase Compounds to Market 542
11.6 New Approaches in ACCase Chemistry 545
11.7 Summary and Conclusions 551
12 Homogentisate Solanesyltransferase (HST) Inhibitors: Cyclopyrimorate 559
Mamiko Shino, Takahiro Hamada, and Shinichi Banba
12.1 Introduction 559
12.2 Discover of Cyclopyrimorate 559
12.3 Mode of Action of Cyclopyrimorate 561
12.4 Biological Spectrum and Activity of Cyclopyrimorate 567
12.5 Other HST Inhibitors 568
12.6 Summary and Conclusions 568
13 Solanesyl Diphosphate Synthase Inhibitors: Aclonifen 571
Gudrun Lange, Mohan Padmanaban, and Bernd Laber
13.1 Introduction 571
13.2 Synthesis of Aclonifen 571
13.3 Elucidation of the Aclonifen Site of Action 572
13.4 Mechanism of Solanesyl Diphosphate Synthase Inhibition 574
13.5 Molecular Basis of Aclonifen Binding to Solanesyl Diphosphate Synthase 575
13.6 Species and Isoform Selectivity 577
13.7 Solanesyl Diphosphate Synthase Inhibitors: Recent Developments 579
14 Inhibitors of the Deoxy-D-Xylulose Phosphate Synthase (DOXP Synthase) 589
Saptarshi De, Ryan Emptage, and Il-Ho Kang
14.1 Introduction 589
14.2 Mode of Action 589
14.3 Chemical Synthesis 592
14.4 Clomazone 593
14.5 Bixlozone 595
14.6 Other Known Isoxazolidinone Herbicides 595
14.7 Summary 598
15 Fatty Acid Thioesterase Inhibitors 603
Matthias Witschel
15.1 Introduction 603
15.2 Fatty Acid Thioesterases in Plants 603
15.3 Biochemical Validation of Fatty Acid Thioesterase Inhibition by Commercial Herbicides 604
15.4 Crystal Structure of Cinmethylin- and Cumyluron-Bound Fatty Acid Thioesterase A 605
15.5 Chemical Structure Types and Activities of Fatty Acid Thioesterase Inhibitors 606
15.6 Synthetic Routes for Fatty Acid Thioesterase Inhibitors 609
16 Validation of Dihydroorotate Dehydrogenase as a Herbicide Target: Discovery of Tetflupyrolimet 613
Thomas P. Selby, Alison M. Levens, IL-Ho Kang, Ryan P. Emptage, and John L. Andreassi
16.1 Introduction 613
16.2 Pyrimidine Biosynthesis Pathway 613
16.3 DHODH as an Agrochemical Target 615
16.4 Search for a New Mode of Action Herbicide 616
16.5 Conclusion 620
17 Photosynthesis Inhibitors: Regulatory Aspects, Reregistration in Europe, Market Trends, and New Products 623
Martyn Griffiths
17.1 Introduction 623
17.2 The Approval Process for Active Substances in the World and Especially the European Union 626
17.3 Main Changes in Guidelines Regarding EU Reapproval 631
17.4 New Regulations in Europe 638
17.5 Situation of PS II Inhibitors in the EU Markets 642
17.6 Current Market Share of PS II Compound Groups 643
17.7 A Relatively New Herbicide for Corn and Sugarcane: Amicarbazone 650
17.8 Conclusions 653
18 New Aspects of Plant Regulators 659
Hans Ulrich Haas
18.1 Introduction 659
18.2 Plant Growth Regulators 659
18.3 Plant Growth Regulators in Modern Agriculture 661
18.4 Conclusions and Developments 667
References 667
Index 671
Este título pertence ao(s) assunto(s) indicados(s). Para ver outros títulos clique no assunto desejado.
Agrochemicals; herbicides; biochemistry; crop protection compounds; chemical synthesis; physicochemical properties; structure-activity relationship; mode of action; auxin mimics; safener; HRAC; safety profile; weed management; resistance management; herbicide-resistant crops; seed treatment; agrochemical industry; industrial chemistry
Volume 1
Preface to the Fourth Edition xxxi
Part I Herbicides 1
Overview 3
Beth Lorsbach
1 Herbicide Resistance Action Committee (HRAC): Herbicide Classification, Resistance Evolution, Survey, and Resistance Mitigation Activities 5
Roland Beffa, Hubert Menne, and Helmut Koecher
1.1 Introduction 5
1.2 HRAC Herbicide Classification System 7
1.3 Herbicide Resistance Survey 9
2 Acetohydroxyacid Synthase Structure and Inhibitors (AHAS/ALS) 31
2.1 Biochemistry, Structure, Regulation, Mechanism, Inhibition of the Target, and Resistance 31
Ryan P. Emptage and Steven Gutteridge
2.2 Newer Sulfonylureas 50
Oswald Ort and David M. Barber
2.3 Imidazolinone Herbicides 90
Dale L. Shaner, Mark Stidham, Bijay Singh, and Siyuan Tan
2.4 Triazolopyrimidines 101
Timothy C. Johnson, Richard K. Mann, Paul R. Schmitzer, Roger E. Gast, and Gerrit J. de Boer
2.5 Triazolopyrmidine Addendum 119
Paul R. Schmitzer and Jossian Oppenheimer
2.6 Pyrimidinyl Carboxylates and Sulfonanilides 124
Atsushi Shibayama, Osamu Watanabe, and Tsutomu Shimizu
2.7 Sulfonylaminocarbonyl-Triazolinones 150
Klaus-Helmut Mueller, Hans-Joachim Santel, Ernst Rudolf F. Gesing, and Gilbert Besong
3 Protoporphyrinogen IX Oxidase Inhibitors 175
3.1 Protoporphyrinogen IX Oxidase Inhibitors 175
Tobias Seiser, Jared Bell, Dustin Lewis, Cyrill Zagar, Rex Liebl, George Theodoridis, and Matthias Witschel
3.2 The PPO Target Site, Resistance Evolution, and Herbicide Tolerance Trait Discovery 215
Jared Bell, Aimone Porri, and Carla Yerkes
4 Herbicides with Bleaching Properties 247
4.1 Phytoene Desaturase Inhibitors 247
Matthias Witschel and Gerhard Hamprecht
4.2 Hydroxyphenylpyruvate Dioxygenase (HPPD): The Herbicide Target 272
John P. Evans and Timothy R. Hawkes
4.3 Triketones 283
Andrew J.F. Edmunds and James A. Morris
4.4 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Inhibitors: Heterocycles 314
Andreas van Almsick and Paul M. Burton
5 New Auxin Mimics and Herbicides 337
5.1 The Molecular Mode of Action of Auxin Herbicides 337
Jared L. Bell, Paul R. Schmitzer, and Hudson Takano
5.2 New Auxin Mimic Herbicides: Aminopyralid 352
Jeffrey B. Epp, Roger E. Gast, Jeff A. Nelson, and William C. Lo
5.3 Pyrimidine Carboxylic Acids: Aminocyclopyrachlor 361
Hansjoerg Kraehmer, Harry J. Strek, Jon S. Claus, David M. Barber, and Bruce L. Finkelstein
5.4 6-Arylpicolinates: Halauxifen-Methyl and Florpyrauxifen-Benzyl 378
Roger E. Gast, Mauricio Morell, Monte R. Weimer, and Paul R. Schmitzer
6 Herbicides Disturbing the Synthesis of Very-Long-Chain Fatty Acids 385
6.1 Inhibitors of the Synthesis of Very-Long-Chain Fatty Acids (VLCFAs) 385
Rebecka Duecker, Hansjoerg Kraehmer, Peter Babczinski, and Roland Beffa
6.2 Chemistry and Biology of Oxyacetamides, Tetrazolinones, and Triazolinones 398
Hansjoerg Kraehmer and Roland Beffa
6.3 Isoxazolines 408
Masao Nakatani, Masaru Shibata, Atsushi Sato, Hisashi Honda, Yoshitaka Tanetani, Kiyoshi Kawai, Ryo Hanai, Takumi Yoshimura, and Tsutomu Shimizu
7 Inhibitors of Cellulose Biosynthesis 421
Bernd Laber and Hansjoerg Dietrich
7.1 Introduction 421
7.2 Cellulose Biosynthesis 421
7.3 Cellulose Biosynthesis Inhibitors from Different Chemical Classes 426
7.4 Cellulose Biosynthesis Inhibitors from Natural Sources 451
8 Safeners for Herbicides 463
Graham Collier, Beth Lorsbach, Chris Rosinger, and Wolfgang Schulte
8.1 Introduction 463
8.2 Overview of Selected Safeners 467
8.3 Mechanisms of Herbicide Safener Action 475
8.4 Mode of Action of Safeners in Agricultural Practice 480
8.5 Concluding Remarks 485
9 Genetically Modified Herbicide Tolerant Crops 489
9.1 Genetically Modified Herbicide-Resistant Crops: A Future Beyond Glyphosate 489
Chandrima Shyam, Clayton T. Larue, Neha Rana, and Alejandro Perez-Jones
9.2 Glutamine Synthetase Inhibitors 505
Wolfgang Schulte and Clayton T. Larue
10 Microtubulin Assembly Inhibitors (Pyridines) 523
Joshua J. Roth, Jeffrey B. Epp, Darin W. Lickfeldt, Denise P. Cudworth, Daniel D. Loughner, and Lowell D. Markley
10.1 Introduction 523
10.2 Biology of the Microtubulin Assembly Inhibitors (Pyridines) 524
10.3 Environmental Fate of Microtubulin Assembly Inhibitors (Pyridines) 525
10.4 Toxicology of Microtubulin Assembly Inhibitors (Pyridines) 526
10.5 Mode of Action of Microtubulin Assembly Inhibitors (Pyridines) 526
10.6 Synthesis of Dithiopyr and Thiazopyr 527
11 Acetyl-CoA Carboxylase Inhibitors 531
Yunas Bhonoah, Vikas Sikervar, Danielle Sayer, Jean Wenger, Thierry Niderman, Chris Mathews, Steve Wailes, and Christopher M. Baker
11.1 Introduction 531
11.2 Biochemistry and Mode of Action 531
11.3 Commercialized ACCase Inhibitors 535
11.4 The Need for New ACCase-Inhibiting Herbicides 541
11.5 The Challenge of Bringing New ACCase Compounds to Market 542
11.6 New Approaches in ACCase Chemistry 545
11.7 Summary and Conclusions 551
12 Homogentisate Solanesyltransferase (HST) Inhibitors: Cyclopyrimorate 559
Mamiko Shino, Takahiro Hamada, and Shinichi Banba
12.1 Introduction 559
12.2 Discover of Cyclopyrimorate 559
12.3 Mode of Action of Cyclopyrimorate 561
12.4 Biological Spectrum and Activity of Cyclopyrimorate 567
12.5 Other HST Inhibitors 568
12.6 Summary and Conclusions 568
13 Solanesyl Diphosphate Synthase Inhibitors: Aclonifen 571
Gudrun Lange, Mohan Padmanaban, and Bernd Laber
13.1 Introduction 571
13.2 Synthesis of Aclonifen 571
13.3 Elucidation of the Aclonifen Site of Action 572
13.4 Mechanism of Solanesyl Diphosphate Synthase Inhibition 574
13.5 Molecular Basis of Aclonifen Binding to Solanesyl Diphosphate Synthase 575
13.6 Species and Isoform Selectivity 577
13.7 Solanesyl Diphosphate Synthase Inhibitors: Recent Developments 579
14 Inhibitors of the Deoxy-D-Xylulose Phosphate Synthase (DOXP Synthase) 589
Saptarshi De, Ryan Emptage, and Il-Ho Kang
14.1 Introduction 589
14.2 Mode of Action 589
14.3 Chemical Synthesis 592
14.4 Clomazone 593
14.5 Bixlozone 595
14.6 Other Known Isoxazolidinone Herbicides 595
14.7 Summary 598
15 Fatty Acid Thioesterase Inhibitors 603
Matthias Witschel
15.1 Introduction 603
15.2 Fatty Acid Thioesterases in Plants 603
15.3 Biochemical Validation of Fatty Acid Thioesterase Inhibition by Commercial Herbicides 604
15.4 Crystal Structure of Cinmethylin- and Cumyluron-Bound Fatty Acid Thioesterase A 605
15.5 Chemical Structure Types and Activities of Fatty Acid Thioesterase Inhibitors 606
15.6 Synthetic Routes for Fatty Acid Thioesterase Inhibitors 609
16 Validation of Dihydroorotate Dehydrogenase as a Herbicide Target: Discovery of Tetflupyrolimet 613
Thomas P. Selby, Alison M. Levens, IL-Ho Kang, Ryan P. Emptage, and John L. Andreassi
16.1 Introduction 613
16.2 Pyrimidine Biosynthesis Pathway 613
16.3 DHODH as an Agrochemical Target 615
16.4 Search for a New Mode of Action Herbicide 616
16.5 Conclusion 620
17 Photosynthesis Inhibitors: Regulatory Aspects, Reregistration in Europe, Market Trends, and New Products 623
Martyn Griffiths
17.1 Introduction 623
17.2 The Approval Process for Active Substances in the World and Especially the European Union 626
17.3 Main Changes in Guidelines Regarding EU Reapproval 631
17.4 New Regulations in Europe 638
17.5 Situation of PS II Inhibitors in the EU Markets 642
17.6 Current Market Share of PS II Compound Groups 643
17.7 A Relatively New Herbicide for Corn and Sugarcane: Amicarbazone 650
17.8 Conclusions 653
18 New Aspects of Plant Regulators 659
Hans Ulrich Haas
18.1 Introduction 659
18.2 Plant Growth Regulators 659
18.3 Plant Growth Regulators in Modern Agriculture 661
18.4 Conclusions and Developments 667
References 667
Index 671
Preface to the Fourth Edition xxxi
Part I Herbicides 1
Overview 3
Beth Lorsbach
1 Herbicide Resistance Action Committee (HRAC): Herbicide Classification, Resistance Evolution, Survey, and Resistance Mitigation Activities 5
Roland Beffa, Hubert Menne, and Helmut Koecher
1.1 Introduction 5
1.2 HRAC Herbicide Classification System 7
1.3 Herbicide Resistance Survey 9
2 Acetohydroxyacid Synthase Structure and Inhibitors (AHAS/ALS) 31
2.1 Biochemistry, Structure, Regulation, Mechanism, Inhibition of the Target, and Resistance 31
Ryan P. Emptage and Steven Gutteridge
2.2 Newer Sulfonylureas 50
Oswald Ort and David M. Barber
2.3 Imidazolinone Herbicides 90
Dale L. Shaner, Mark Stidham, Bijay Singh, and Siyuan Tan
2.4 Triazolopyrimidines 101
Timothy C. Johnson, Richard K. Mann, Paul R. Schmitzer, Roger E. Gast, and Gerrit J. de Boer
2.5 Triazolopyrmidine Addendum 119
Paul R. Schmitzer and Jossian Oppenheimer
2.6 Pyrimidinyl Carboxylates and Sulfonanilides 124
Atsushi Shibayama, Osamu Watanabe, and Tsutomu Shimizu
2.7 Sulfonylaminocarbonyl-Triazolinones 150
Klaus-Helmut Mueller, Hans-Joachim Santel, Ernst Rudolf F. Gesing, and Gilbert Besong
3 Protoporphyrinogen IX Oxidase Inhibitors 175
3.1 Protoporphyrinogen IX Oxidase Inhibitors 175
Tobias Seiser, Jared Bell, Dustin Lewis, Cyrill Zagar, Rex Liebl, George Theodoridis, and Matthias Witschel
3.2 The PPO Target Site, Resistance Evolution, and Herbicide Tolerance Trait Discovery 215
Jared Bell, Aimone Porri, and Carla Yerkes
4 Herbicides with Bleaching Properties 247
4.1 Phytoene Desaturase Inhibitors 247
Matthias Witschel and Gerhard Hamprecht
4.2 Hydroxyphenylpyruvate Dioxygenase (HPPD): The Herbicide Target 272
John P. Evans and Timothy R. Hawkes
4.3 Triketones 283
Andrew J.F. Edmunds and James A. Morris
4.4 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Inhibitors: Heterocycles 314
Andreas van Almsick and Paul M. Burton
5 New Auxin Mimics and Herbicides 337
5.1 The Molecular Mode of Action of Auxin Herbicides 337
Jared L. Bell, Paul R. Schmitzer, and Hudson Takano
5.2 New Auxin Mimic Herbicides: Aminopyralid 352
Jeffrey B. Epp, Roger E. Gast, Jeff A. Nelson, and William C. Lo
5.3 Pyrimidine Carboxylic Acids: Aminocyclopyrachlor 361
Hansjoerg Kraehmer, Harry J. Strek, Jon S. Claus, David M. Barber, and Bruce L. Finkelstein
5.4 6-Arylpicolinates: Halauxifen-Methyl and Florpyrauxifen-Benzyl 378
Roger E. Gast, Mauricio Morell, Monte R. Weimer, and Paul R. Schmitzer
6 Herbicides Disturbing the Synthesis of Very-Long-Chain Fatty Acids 385
6.1 Inhibitors of the Synthesis of Very-Long-Chain Fatty Acids (VLCFAs) 385
Rebecka Duecker, Hansjoerg Kraehmer, Peter Babczinski, and Roland Beffa
6.2 Chemistry and Biology of Oxyacetamides, Tetrazolinones, and Triazolinones 398
Hansjoerg Kraehmer and Roland Beffa
6.3 Isoxazolines 408
Masao Nakatani, Masaru Shibata, Atsushi Sato, Hisashi Honda, Yoshitaka Tanetani, Kiyoshi Kawai, Ryo Hanai, Takumi Yoshimura, and Tsutomu Shimizu
7 Inhibitors of Cellulose Biosynthesis 421
Bernd Laber and Hansjoerg Dietrich
7.1 Introduction 421
7.2 Cellulose Biosynthesis 421
7.3 Cellulose Biosynthesis Inhibitors from Different Chemical Classes 426
7.4 Cellulose Biosynthesis Inhibitors from Natural Sources 451
8 Safeners for Herbicides 463
Graham Collier, Beth Lorsbach, Chris Rosinger, and Wolfgang Schulte
8.1 Introduction 463
8.2 Overview of Selected Safeners 467
8.3 Mechanisms of Herbicide Safener Action 475
8.4 Mode of Action of Safeners in Agricultural Practice 480
8.5 Concluding Remarks 485
9 Genetically Modified Herbicide Tolerant Crops 489
9.1 Genetically Modified Herbicide-Resistant Crops: A Future Beyond Glyphosate 489
Chandrima Shyam, Clayton T. Larue, Neha Rana, and Alejandro Perez-Jones
9.2 Glutamine Synthetase Inhibitors 505
Wolfgang Schulte and Clayton T. Larue
10 Microtubulin Assembly Inhibitors (Pyridines) 523
Joshua J. Roth, Jeffrey B. Epp, Darin W. Lickfeldt, Denise P. Cudworth, Daniel D. Loughner, and Lowell D. Markley
10.1 Introduction 523
10.2 Biology of the Microtubulin Assembly Inhibitors (Pyridines) 524
10.3 Environmental Fate of Microtubulin Assembly Inhibitors (Pyridines) 525
10.4 Toxicology of Microtubulin Assembly Inhibitors (Pyridines) 526
10.5 Mode of Action of Microtubulin Assembly Inhibitors (Pyridines) 526
10.6 Synthesis of Dithiopyr and Thiazopyr 527
11 Acetyl-CoA Carboxylase Inhibitors 531
Yunas Bhonoah, Vikas Sikervar, Danielle Sayer, Jean Wenger, Thierry Niderman, Chris Mathews, Steve Wailes, and Christopher M. Baker
11.1 Introduction 531
11.2 Biochemistry and Mode of Action 531
11.3 Commercialized ACCase Inhibitors 535
11.4 The Need for New ACCase-Inhibiting Herbicides 541
11.5 The Challenge of Bringing New ACCase Compounds to Market 542
11.6 New Approaches in ACCase Chemistry 545
11.7 Summary and Conclusions 551
12 Homogentisate Solanesyltransferase (HST) Inhibitors: Cyclopyrimorate 559
Mamiko Shino, Takahiro Hamada, and Shinichi Banba
12.1 Introduction 559
12.2 Discover of Cyclopyrimorate 559
12.3 Mode of Action of Cyclopyrimorate 561
12.4 Biological Spectrum and Activity of Cyclopyrimorate 567
12.5 Other HST Inhibitors 568
12.6 Summary and Conclusions 568
13 Solanesyl Diphosphate Synthase Inhibitors: Aclonifen 571
Gudrun Lange, Mohan Padmanaban, and Bernd Laber
13.1 Introduction 571
13.2 Synthesis of Aclonifen 571
13.3 Elucidation of the Aclonifen Site of Action 572
13.4 Mechanism of Solanesyl Diphosphate Synthase Inhibition 574
13.5 Molecular Basis of Aclonifen Binding to Solanesyl Diphosphate Synthase 575
13.6 Species and Isoform Selectivity 577
13.7 Solanesyl Diphosphate Synthase Inhibitors: Recent Developments 579
14 Inhibitors of the Deoxy-D-Xylulose Phosphate Synthase (DOXP Synthase) 589
Saptarshi De, Ryan Emptage, and Il-Ho Kang
14.1 Introduction 589
14.2 Mode of Action 589
14.3 Chemical Synthesis 592
14.4 Clomazone 593
14.5 Bixlozone 595
14.6 Other Known Isoxazolidinone Herbicides 595
14.7 Summary 598
15 Fatty Acid Thioesterase Inhibitors 603
Matthias Witschel
15.1 Introduction 603
15.2 Fatty Acid Thioesterases in Plants 603
15.3 Biochemical Validation of Fatty Acid Thioesterase Inhibition by Commercial Herbicides 604
15.4 Crystal Structure of Cinmethylin- and Cumyluron-Bound Fatty Acid Thioesterase A 605
15.5 Chemical Structure Types and Activities of Fatty Acid Thioesterase Inhibitors 606
15.6 Synthetic Routes for Fatty Acid Thioesterase Inhibitors 609
16 Validation of Dihydroorotate Dehydrogenase as a Herbicide Target: Discovery of Tetflupyrolimet 613
Thomas P. Selby, Alison M. Levens, IL-Ho Kang, Ryan P. Emptage, and John L. Andreassi
16.1 Introduction 613
16.2 Pyrimidine Biosynthesis Pathway 613
16.3 DHODH as an Agrochemical Target 615
16.4 Search for a New Mode of Action Herbicide 616
16.5 Conclusion 620
17 Photosynthesis Inhibitors: Regulatory Aspects, Reregistration in Europe, Market Trends, and New Products 623
Martyn Griffiths
17.1 Introduction 623
17.2 The Approval Process for Active Substances in the World and Especially the European Union 626
17.3 Main Changes in Guidelines Regarding EU Reapproval 631
17.4 New Regulations in Europe 638
17.5 Situation of PS II Inhibitors in the EU Markets 642
17.6 Current Market Share of PS II Compound Groups 643
17.7 A Relatively New Herbicide for Corn and Sugarcane: Amicarbazone 650
17.8 Conclusions 653
18 New Aspects of Plant Regulators 659
Hans Ulrich Haas
18.1 Introduction 659
18.2 Plant Growth Regulators 659
18.3 Plant Growth Regulators in Modern Agriculture 661
18.4 Conclusions and Developments 667
References 667
Index 671
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Agrochemicals; herbicides; biochemistry; crop protection compounds; chemical synthesis; physicochemical properties; structure-activity relationship; mode of action; auxin mimics; safener; HRAC; safety profile; weed management; resistance management; herbicide-resistant crops; seed treatment; agrochemical industry; industrial chemistry
