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 Köcher 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 Müller, 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 Hansjörg Krähmer, 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 Dücker, Hansjörg Krähmer, Peter Babczinski, and Roland Beffa 6.2 Chemistry and Biology of Oxyacetamides, Tetrazolinones, and Triazolinones 398 Hansjörg Krähmer 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 Hansjörg 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 Volume 2 Preface to the Fourth Edition xxv Part II Fungicides 687 Overview 689 Clemens Lamberth 19 FRAC Mode-of-Action Classification and Resistance Risk of Fungicides 691 Andreas Goertz, Dietrich Hermann, and Klaus Stenzel 20 Fungicides Acting on Oxidative Phosphorylation 715 20.1 The Biochemistry of Oxidative Phosphorylation 715 Urvashi Thacker, Stefano Rendine, and Fergus Earley 20.2 Inhibitors of Complex III 742 20.2.
1 Strobilurins and Other Qo Inhibitors 742 Markus Gewehr, Ian Craig, and Hubert Sauter 20.2.2 Picolinamides and Other Qi Inhibitors 789 Kevin G. Meyer and Chenglin Yao 20.3 Inhibitors of Complex II (Succinate Dehydrogenase) 803 20.3.1 Succinate Dehydrogenase Inhibitors: Anilides 803 Joachim Rheinheimer and Christian Winter 20.3.
2 Succinate Dehydrogenase Inhibitors: N-Benzyl-N-cyclopropylamides 818 Michael Maue, Philippe Desbordes, Jochen Kleemann, and Andreas Mehl 20.3.3 Succinate Dehydrogenase.