Modern Crop Protection Compounds, Volume 1

Peter Jeschke was a senior fellow in research and development in Pest Control Chemistry at Bayer AG Crop Science in Germany, from 1997 until his retirement in 2022. He is also an honorary professor at the Heinrich Heine University Düsseldorf, Germany.Clemens Lamberth retired in 2024 after more than 30 years as a senior principal scientist in the chemical research department of Syngenta Crop Protection AG in Switzerland. He is specialized in the discovery of fungicides.Beth Lorsbach is the Global Head of Innovation and Development at Nufarm in Indianapolis, USA. She is responsible for delivering innovative and disruptive solutions to solve farmers' needs as Nufarm pivots to become an agriculture innovator.

• Volume 1Preface to the Fourth Edition xxxiPart I Herbicides 1Overview 3Beth Lorsbach1 Herbicide Resistance Action Committee (HRAC): Herbicide Classification, Resistance Evolution, Survey, and Resistance Mitigation Activities 5Roland Beffa, Hubert Menne, and Helmut Köcher1.1 Introduction 51.2 HRAC Herbicide Classification System 71.3 Herbicide Resistance Survey 92 Acetohydroxyacid Synthase Structure and Inhibitors (AHAS/ALS) 312.1 Biochemistry, Structure, Regulation, Mechanism, Inhibition of the Target, and Resistance 31Ryan P. Emptage and Steven Gutteridge2.2 Newer Sulfonylureas 50Oswald Ort and David M. Barber2.3 Imidazolinone Herbicides 90Dale L. Shaner, Mark Stidham, Bijay Singh, and Siyuan Tan2.4 Triazolopyrimidines 101Timothy C. Johnson, Richard K. Mann, Paul R. Schmitzer, Roger E. Gast, and Gerrit J. de Boer2.5 Triazolopyrmidine Addendum 119Paul R. Schmitzer and Jossian Oppenheimer2.6 Pyrimidinyl Carboxylates and Sulfonanilides 124Atsushi Shibayama, Osamu Watanabe, and Tsutomu Shimizu2.7 Sulfonylaminocarbonyl-Triazolinones 150Klaus-Helmut Müller, Hans-Joachim Santel, Ernst Rudolf F. Gesing, and Gilbert Besong3 Protoporphyrinogen IX Oxidase Inhibitors 1753.1 Protoporphyrinogen IX Oxidase Inhibitors 175Tobias Seiser, Jared Bell, Dustin Lewis, Cyrill Zagar, Rex Liebl, George Theodoridis, and Matthias Witschel3.2 The PPO Target Site, Resistance Evolution, and Herbicide Tolerance Trait Discovery 215Jared Bell, Aimone Porri, and Carla Yerkes4 Herbicides with Bleaching Properties 2474.1 Phytoene Desaturase Inhibitors 247Matthias Witschel and Gerhard Hamprecht4.2 Hydroxyphenylpyruvate Dioxygenase (HPPD): The Herbicide Target 272John P. Evans and Timothy R. Hawkes4.3 Triketones 283Andrew J.F. Edmunds and James A. Morris4.4 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Inhibitors: Heterocycles 314Andreas van Almsick and Paul M. Burton5 New Auxin Mimics and Herbicides 3375.1 The Molecular Mode of Action of Auxin Herbicides 337Jared L. Bell, Paul R. Schmitzer, and Hudson Takano5.2 New Auxin Mimic Herbicides: Aminopyralid 352Jeffrey B. Epp, Roger E. Gast, Jeff A. Nelson, and William C. Lo5.3 Pyrimidine Carboxylic Acids: Aminocyclopyrachlor 361Hansjörg Krähmer, Harry J. Strek, Jon S. Claus, David M. Barber, and Bruce L. Finkelstein5.4 6-Arylpicolinates: Halauxifen-Methyl and Florpyrauxifen-Benzyl 378Roger E. Gast, Mauricio Morell, Monte R. Weimer, and Paul R. Schmitzer6 Herbicides Disturbing the Synthesis of Very-Long-Chain Fatty Acids 3856.1 Inhibitors of the Synthesis of Very-Long-Chain Fatty Acids (VLCFAs) 385Rebecka Dücker, Hansjörg Krähmer, Peter Babczinski, and Roland Beffa6.2 Chemistry and Biology of Oxyacetamides, Tetrazolinones, and Triazolinones 398Hansjörg Krähmer and Roland Beffa6.3 Isoxazolines 408Masao Nakatani, Masaru Shibata, Atsushi Sato, Hisashi Honda, Yoshitaka Tanetani, Kiyoshi Kawai, Ryo Hanai, Takumi Yoshimura, and Tsutomu Shimizu7 Inhibitors of Cellulose Biosynthesis 421Bernd Laber and Hansjörg Dietrich7.1 Introduction 4217.2 Cellulose Biosynthesis 4217.3 Cellulose Biosynthesis Inhibitors from Different Chemical Classes 4267.4 Cellulose Biosynthesis Inhibitors from Natural Sources 4518 Safeners for Herbicides 463Graham Collier, Beth Lorsbach, Chris Rosinger, and Wolfgang Schulte8.1 Introduction 4638.2 Overview of Selected Safeners 4678.3 Mechanisms of Herbicide Safener Action 4758.4 Mode of Action of Safeners in Agricultural Practice 4808.5 Concluding Remarks 4859 Genetically Modified Herbicide Tolerant Crops 4899.1 Genetically Modified Herbicide-Resistant Crops: A Future Beyond Glyphosate 489Chandrima Shyam, Clayton T. Larue, Neha Rana, and Alejandro Perez-Jones9.2 Glutamine Synthetase Inhibitors 505Wolfgang Schulte and Clayton T. Larue10 Microtubulin Assembly Inhibitors (Pyridines) 523Joshua J. Roth, Jeffrey B. Epp, Darin W. Lickfeldt, Denise P. Cudworth, Daniel D. Loughner, and Lowell D. Markley10.1 Introduction 52310.2 Biology of the Microtubulin Assembly Inhibitors (Pyridines) 52410.3 Environmental Fate of Microtubulin Assembly Inhibitors (Pyridines) 52510.4 Toxicology of Microtubulin Assembly Inhibitors (Pyridines) 52610.5 Mode of Action of Microtubulin Assembly Inhibitors (Pyridines) 52610.6 Synthesis of Dithiopyr and Thiazopyr 52711 Acetyl-CoA Carboxylase Inhibitors 531Yunas Bhonoah, Vikas Sikervar, Danielle Sayer, Jean Wenger, Thierry Niderman, Chris Mathews, Steve Wailes, and Christopher M. Baker11.1 Introduction 53111.2 Biochemistry and Mode of Action 53111.3 Commercialized ACCase Inhibitors 53511.4 The Need for New ACCase-Inhibiting Herbicides 54111.5 The Challenge of Bringing New ACCase Compounds to Market 54211.6 New Approaches in ACCase Chemistry 54511.7 Summary and Conclusions 55112 Homogentisate Solanesyltransferase (HST) Inhibitors: Cyclopyrimorate 559Mamiko Shino, Takahiro Hamada, and Shinichi Banba12.1 Introduction 55912.2 Discover of Cyclopyrimorate 55912.3 Mode of Action of Cyclopyrimorate 56112.4 Biological Spectrum and Activity of Cyclopyrimorate 56712.5 Other HST Inhibitors 56812.6 Summary and Conclusions 56813 Solanesyl Diphosphate Synthase Inhibitors: Aclonifen 571Gudrun Lange, Mohan Padmanaban, and Bernd Laber13.1 Introduction 57113.2 Synthesis of Aclonifen 57113.3 Elucidation of the Aclonifen Site of Action 57213.4 Mechanism of Solanesyl Diphosphate Synthase Inhibition 57413.5 Molecular Basis of Aclonifen Binding to Solanesyl Diphosphate Synthase 57513.6 Species and Isoform Selectivity 57713.7 Solanesyl Diphosphate Synthase Inhibitors: Recent Developments 57914 Inhibitors of the Deoxy-D-Xylulose Phosphate Synthase (DOXP Synthase) 589Saptarshi De, Ryan Emptage, and Il-Ho Kang14.1 Introduction 58914.2 Mode of Action 58914.3 Chemical Synthesis 59214.4 Clomazone 59314.5 Bixlozone 59514.6 Other Known Isoxazolidinone Herbicides 59514.7 Summary 59815 Fatty Acid Thioesterase Inhibitors 603Matthias Witschel15.1 Introduction 60315.2 Fatty Acid Thioesterases in Plants 60315.3 Biochemical Validation of Fatty Acid Thioesterase Inhibition by Commercial Herbicides 60415.4 Crystal Structure of Cinmethylin- and Cumyluron-Bound Fatty Acid Thioesterase A 60515.5 Chemical Structure Types and Activities of Fatty Acid Thioesterase Inhibitors 60615.6 Synthetic Routes for Fatty Acid Thioesterase Inhibitors 60916 Validation of Dihydroorotate Dehydrogenase as a Herbicide Target: Discovery of Tetflupyrolimet 613Thomas P. Selby, Alison M. Levens, IL-Ho Kang, Ryan P. Emptage, and John L. Andreassi16.1 Introduction 61316.2 Pyrimidine Biosynthesis Pathway 61316.3 DHODH as an Agrochemical Target 61516.4 Search for a New Mode of Action Herbicide 61616.5 Conclusion 62017 Photosynthesis Inhibitors: Regulatory Aspects, Reregistration in Europe, Market Trends, and New Products 623Martyn Griffiths17.1 Introduction 62317.2 The Approval Process for Active Substances in the World and Especially the European Union 62617.3 Main Changes in Guidelines Regarding EU Reapproval 63117.4 New Regulations in Europe 63817.5 Situation of PS II Inhibitors in the EU Markets 64217.6 Current Market Share of PS II Compound Groups 64317.7 A Relatively New Herbicide for Corn and Sugarcane: Amicarbazone 65017.8 Conclusions 65318 New Aspects of Plant Regulators 659Hans Ulrich Haas18.1 Introduction 65918.2 Plant Growth Regulators 65918.3 Plant Growth Regulators in Modern Agriculture 66118.4 Conclusions and Developments 667References 667Index 671