Modern Crop Protection Compounds, 4 Volume Set
portes grátis
Modern Crop Protection Compounds, 4 Volume Set
Lorsbach, Beth; Jeschke, Peter; Lamberth, Clemens
Wiley-VCH Verlag GmbH
04/2026
2208
Dura
Inglês
9783527352500
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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
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 Inhibitors: N-Phenethylamides 827
Clemens Lamberth
20.3.4 Succinate Dehydrogenase Inhibitors: N-Pyridinylethylamides 837
Andreas Mehl, Jochen Kleemann, Heiko Rieck, and Pierre-Yves Coqueron
20.4 Uncouplers of Oxidative Phosphorylation 847
William G. Whittingham
21 Fungicides Acting on Amino Acids and Protein Synthesis: Anilinopyrimidines - Assumed Methionine Biosynthesis Inhibitors 869
Ulrich Gisi, Urs Mueller, and Samantha Hall
22 Fungicides Acting on Signal Transduction 881
22.1 Mode of Action of Fludioxonil, Fenpiclonil, and Quinoxyfen 881
Andrew Corran
22.2 Chemistry and Biology of Fludioxonil, Fenpiclonil, and Quinoxyfen 888
Gertrude Knauf-Beiter, Ronald Zeun, and Clemens Lamberth
23 Fungicides Acting on Mitosis and Cell Division: Zoxamide, an Antitubulin Fungicide for Control of Oomycete Pathogens 907
David H. Young
24 Sterol Biosynthesis Inhibitors 917
Andreas Mehl, Klaus Stenzel, David Bernier, and Jean-Pierre Vors
25 Carboxylic Acid Amide (CAA) Fungicides 973
Mathias Blum, Ulrich Gisi, Clemens Lamberth, Andreas Mehl, and Thomas Seitz
26 Fluopicolide: Anti-oomycete Fungicide with a Unique Mode of Action 995
Bernd Essigmann, Jochen Kleemann, Marie-Pascale Latorse, Valerie Toquin, Emilia Hilz, Roland Beffa, and Luigi Di Vietro
27 Melanin Biosynthesis Inhibitors 1003
Hiroyuki Hagiwara, Takahiro Hamada, and Shinichi Banba
28 Modern Powdery Mildew Fungicides 1023
Jochen Dietz and Christian Winter
29 Newest Aspects of Nucleic Acid Synthesis Inhibitors - Metalaxyl-M 1039
Helge Sierotzki, Laura Quaranta, Stefano Torriani, Ulrich Gisi, and Urs Mueller
30 Host Defense Inducers 1051
Valerie Toquin, Christoph A. Braun, Catherine Sirven, Lutz Assmann, Jeremy Dufour, Stefan Hillebrand, and Emilia Hilz
31 Oxysterol-Binding Protein Inhibitors 1075
Clemens Lamberth
32 Quinofumelin and Other Dihydroorotate Dehydrogenase Inhibitors 1085
Shinichi Banba, Hiroyuki Ito, and Norikazu Higashimura
33 Pyridachlometyl and Other Tubulin Dynamics Modulators 1099
Yuichi Matsuzaki, Hiroshi Ikegami, Tadafumi Matsunaga, and Akio Manabe
34 Aminopyrifen and Other GPI-anchored Wall Transfer Protein Inhibitors 1111
Masahiro Hatamoto and Ryo Aizawa
35 Fungicides with Unknown Mode of Action 1125
Clemens Lamberth
Index 1135
Volume 3a
Preface to the Fourth Edition xxv
Part III Insecticides 1147
Overview 1149
Peter Jeschke
36 IRAC: Insecticide Resistance and Mode of Action Classification of Insecticides 1155
Ralf Nauen, Russell Slater, Thomas C. Sparks, Alfred Elbert, and Alan McCaffery
37 Insect Molting and Metamorphosis 1173
37.1 Molting Disruptors, Dipteran: Cyromazine 1173
Yeshua Sempere Molina and Sven Geibel
37.2 Ecdysone Receptor Agonists: Diacylhydrazines 1178
Luis E. Gomez, Tarlochan Singh Dhadialla, and Ronald Ross Jr
37.3 Juvenil Hormone Receptor Modulators: Pyriproxyfen 1221
Makoto Hatakoshi and Katsuya Natsuhara
38 Chitin Biosynthesis 1237
38.1 Chitin Structure and Biosynthesis 1237
Sven Geibel, Neil A. Spomer, Joel J. Sheets, and Yeshua Sempere
38.2 Inhibitors of Chitin Biosynthesis Affecting CHS1 1243
Yeshua Sempere Molina, Neil A. Spomer, Joel J. Sheets, and Sven Geibel
38.3 Inhibitors of Chitin Biosynthesis, Type 1: Buprofezin 1252
Yeshua Sempere and Sven Geibel
38.4 Mite Growth Inhibitors Affecting CHS1: Clofentezine, Hexythiazox, and Etoxazole 1257
Ralf Nauen and Thomas Bretschneider
39 Microbial Disruptors of Insect Midgut Membranes 1275
Jeroen Van Rie
40 Metabolic Processes 1313
40.1 Inhibitors of Oxidative Phosphorylation 1313
Fergus Earley
40.1.1 Inhibitors of Mitochondrial ATP Synthase 1314
Fergus Earley, Roger Hall, and Josef Ehrenfreund
40.2 Uncouplers of Oxidative Phosphorylation via Disruption of the Proton the Gradient 1326
David Kuhn, Nigel Armes, and Catia Sazaki
40.3 Inhibitors of Mitochondrial Electron Transport: Acaricides and Insecticides 1333
Peter Luemmen, Thomas C. Sparks, Carl V. DeAmicis, Mark A. Dekeyser, Takashi Furuya, Motofumi Nakano, Shinsuke Fujioka, and Kozo Machiya
40.3.1 Introduction: The Mitochondrial Respiratory Chain 1333
40.3.2 Mitochondrial Complex I Electron Transport Inhibitors 1335
40.3.3 Mitochondrial Complex II Electron Transport Inhibitors 1344
40.3.3.4 Pyflubumide 1350
Takashi Furuya, Motofumi Nakano, Shinsuke Fujioka, and Kozo Machiya
40.3.3.5 Binding Modes, Target-Site Mutations, and Species Selectivity of Complex II Inhibitors 1361
40.3.4 Mitochondrial Complex III Electron Transport Inhibitors 1363
40.3.5 Mitochondrial Complex III Electron Transport Inhibitors - Qi site: Flometoquin 1372
Takeru Kobayashi, Ryo Horikoshi, and Andrew J. Crossthwaite
40.4 Inhibitors of Acetyl-CoA-Carboxylase 1379
Peter Jeschke, Reiner Fischer, and Ralf Nauen
40.4.1 Introduction 1379
40.4.2 Taget Site Mutations of Acetyl-CoA-Carboxylase 1380
40.4.3 Tetronic Acid Derivatives: Spirodiclofen and Spiromesifen 1383
Peter Jeschke, Reiner Fischer, and Ralf Nauen
40.4.4 Tetramic Acid Derivatives: Spirotetramat 1397
Peter Jeschke, Reiner Fischer, and Ralf Nauen
40.4.5 Tetramic Acid Derivatives: Spiropidion 1408
Anke Buchholz and Michel Muehlebach
40.4.6 Tetramic Acid Derivatives: Spidoxamat 1421
Reiner Fischer, Christian Marienhagen, and Ralf Nauen
41 Nervous System 1429
41.1 Nicotinic Acetylcholine Receptor Competitive Modulators, Allosteric Modulators, and Channel Blockers: Target and Selectivity Aspects 1429
Peter Jeschke, Ralf Nauen, and Michael Edmund Beck
41.2 Chemical Structural Features of Nicotinic Acetylcholine Receptor Competitive Modulators 1481
Peter Jeschke
41.2.1 Introduction 1481
41.2.2 Active Ingredients of the IRAC MoA Subgroup 4A 1482
41.2.3 Active Ingredients of the IRAC MoA Subgroups 4C to 4E 1485
41.2.4 Neonicotinoids 1487
41.2.4.1 Noncyclic Neonicotinoids 1487
Peter Jeschke
41.2.4.2 Five-Membered Heterocycles: Imidacloprid and Thiacloprid 1517
Peter Jeschke and Koichi Moriya
41.2.4.3 Six-Membered Heterocycles: Thiamethoxam and AKD 1022 1537
Peter Maienfisch
41.2.5 Sulfoximines: Sulfoxaflor 1566
Thomas C. Sparks, Michael R. Loso, Trent Perry, Frank J. Wessels, Ann M. Buysse, Benjamin M. Nugent, Vincent J. Kramer, Luis E. Gomez, Imre Mezei, David G.J. Mann, Nick X. Wang, and Gerald B. Watson
Volume 3b
Preface to the Fourth Edition xxvii
41.2.6 Butenolides: Flupyradifurone 1599
Peter Jeschke, Ralf Nauen, Robert Velten, Michael E. Beck, Matthias Haas, Christian Funke, and Georg Raupach
41.2.7 Mesoionics 1626
41.2.7.1 Triflumezopyrim 1626
Daniel Cordova, Wenming Zhang, Caleb W. Holyoke Jr, James D. Barry, Vineet Singh, Isaac B. Annan, Luis A.F. Teixeira, and John L. Andreassi
41.2.7.2 Fenmezoditiaz 1642
Joachim Dickhaut, Martin Weisel, Huazhang Huang, Lixin Mao, Barbara Wedel, Colin Ehnes, and Kai Ristau
41.2.8 Pyridinylidenes: Flupyrimin 1651
Ryo Horikoshi, Takehito Terajima, Kenji Shimomura, and Motohiro Tomizawa
41.3 Nicotinic Acetylcholine Receptor Allosteric Modulators - Site I: Spinosyns 1659
Thomas C. Sparks, Natalie C. Giampietro, Trent Perry, Frank Wessels, David G.J. Mann, Babu Raman, John Daeuble, M. Paige Oliver, Gary D. Crouse, Gerald B. Watson, James E. Dripps, and Imre Mezei
41.4 Nicotinic Acetylcholine Receptor Allosteric Modulators - Site II: GS-Omega/Kappa HxTx-Hv1a Peptide 1687
Dara G. Stockton
41.5 Sodium Channel Modulators 1702
Peter Jeschke
41.6 Voltage-dependent Sodium Channel Blockers 1718
41.6.1 Oxadiazines: Indoxacarb 1718
Stephen F. McCann, Daniel Cordova, John T. Andaloro, and George P. Lahm
41.6.2 Semicarbazone: Metaflumizone 1734
David Kuhn, Kazuhiro Takagi, Tomokazu Hino, Nigel Armes, and Desiree Hodges
41.7 GABA-gated Chloride Channel Blockers 1744
41.7.1 Phenylpyrazoles: Ethiprole and Fipronil 1744
Vincent L. Salgado, Keith A. Holmes, Lixin Mao, and Stefan Schnatterer
41.8 GABA-gated Chloride Channel Allosteric Modulators 1782
41.8.1 Meta-diamides: Broflanilide 1782
Toshifumi Nakao and Shinichi Banba
41.8.2 Isoxazolines: Fluxametamide 1791
Takeshi Mita, Yuki Furukawa, Motoyoshi Iwasa, Takamasa Kikuchi, Miho Asahi, and Mitsuaki Komoda
41.8.3 Isoxazolines: Isocycloseram 1801
Jerome Cassayre and Myriem El Qacemi
41.9 Glutamate-gated Chloride Channel Allosteric Modulators: Avermectins and Milbemycins 1815
Ottmar Franz Hueter and Thomas Pitterna
42 Chordotonal Organ TRPV Channel Modulators 1839
42.1 Pyridine Azomethine Derivatives: Pymetrozine and Pyrifluquinazon 1839
Peter Maienfisch
42.2 Pyropenes: Afidopyropen 1856
Desiree M. Hodges, Anna K. Hoffarth, Ryo Horikoshi, Christopher Koradin, James Machamer, Christoph Schissler, Toshiaki Sunazuka, Robert R. Svadlenak, and Siddharth Tiwari
42.3 Indazapyroxamet 1868
Wenming Zhang, Daniel Cordova, Jason Hamm, Billy Annan, David Clark, and Suobao Rong
43 Chordotonal Organ Modulators 1879
43.1 Chordotonal Organ Nicotinamidase Inhibitors: Flonicamid 1879
Peter Maienfisch
43.2 Chordotonal Organ Modulators - Undefined Target Site: Dimpropyridaz 1890
Barbara Wedel, Desiree Hodges, and Karsten Koerber
44 New Unknown Mode of Action 1899
44.1 Pyridalyl 1899
Shigeru Saito and Noriyasu Sakamoto
44.2 Benzpyrimoxan 1906
Eikoh Satoh
45 Insecticides Affecting Calcium Homeostasis 1913
45.1 Ryanodine Receptor Modulators: Diamides 1913
Peter Luemmen, Ulrich Ebbinghaus-Kintscher, Takao Masaki, Hiroshi Hamaguchi, and Takashi Hirooka
45.2 Phthalic Acid Diamide: Flubendiamide 1923
Ulrich Ebbinghaus-Kintscher, Peter Luemmen, Takao Masaki, Hiroshi Hamaguchi, and Takashi Hirooka
45.3 Anthranilic Diamides: Chlorantraniliprole and Cyantraniliprole 1929
George P. Lahm, Daniel Cordova, James D. Barry, John T. Andaloro, Isaac B. Annan, Paula C. Marcon, Hector E. Portillo, Luis A. Teixeira, Thomas M. Stevenson, and Thomas P. Selby
45.4 Anthranilic Diamide: Cyclaniliprole 1949
Masamitsu Tsukamoto, Taku Hamamoto, Satoko Fujii, Chiaki Takeda, Yusuke Kumakura, and Masayuki Morita
45.5 Anthranilic Diamide: Tetraniliprole 1960
Ruediger Fischer, Christian Funke, Sergii Pazenok, and Matthieu Willot
46 Vesicular Acetylcholine Transporter Inhibitors 1975
46.1 Oxazosulfyl 1975
Mai Ito, Shinya Nishimura, and Yoshihiko Nokura
47 Nematicides 1979
47.1 IRAC: Nematicide Mode of Action Classification 1979
Peter Maienfisch
47.2 Mitochondrial Complex II Electron Transport Inhibitors - Succinate-coenzyme Q Reductase 2010
47.2.1 Fluopyram 2010
Peter Luemmen, Svenja Bellof, and Helmut Fuersch
47.2.2 Cyclobutrifluram 2023
Olivier Loiseleur, Anthony Flemming, Torsten Luksch, Brigitte Slaats, Matthias Gaberthueel, Marcus Guest, and Richard Currie
47.3 Compounds of Unknown or Uncertain Mode of Action 2037
47.3.1 Fluazaindolizine 2037
George P. Lahm, John A. Wiles, Daniel Cordova, Tim Thoden, Johan Desaeger, Ben K. Smith, Thomas F. Pahutski, Michel A. Rivera, Tony Meloro, Roman Kucharczyk, Renee M. Lett, Anne Daly, and Brenton T. Smith
47.3.2 Fluazaindolizine (Addendum) 2047
Tim Thoden, John A. Wiles, Chaoxian Geng, and Timothy Wilson
Index 2051
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
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 Inhibitors: N-Phenethylamides 827
Clemens Lamberth
20.3.4 Succinate Dehydrogenase Inhibitors: N-Pyridinylethylamides 837
Andreas Mehl, Jochen Kleemann, Heiko Rieck, and Pierre-Yves Coqueron
20.4 Uncouplers of Oxidative Phosphorylation 847
William G. Whittingham
21 Fungicides Acting on Amino Acids and Protein Synthesis: Anilinopyrimidines - Assumed Methionine Biosynthesis Inhibitors 869
Ulrich Gisi, Urs Mueller, and Samantha Hall
22 Fungicides Acting on Signal Transduction 881
22.1 Mode of Action of Fludioxonil, Fenpiclonil, and Quinoxyfen 881
Andrew Corran
22.2 Chemistry and Biology of Fludioxonil, Fenpiclonil, and Quinoxyfen 888
Gertrude Knauf-Beiter, Ronald Zeun, and Clemens Lamberth
23 Fungicides Acting on Mitosis and Cell Division: Zoxamide, an Antitubulin Fungicide for Control of Oomycete Pathogens 907
David H. Young
24 Sterol Biosynthesis Inhibitors 917
Andreas Mehl, Klaus Stenzel, David Bernier, and Jean-Pierre Vors
25 Carboxylic Acid Amide (CAA) Fungicides 973
Mathias Blum, Ulrich Gisi, Clemens Lamberth, Andreas Mehl, and Thomas Seitz
26 Fluopicolide: Anti-oomycete Fungicide with a Unique Mode of Action 995
Bernd Essigmann, Jochen Kleemann, Marie-Pascale Latorse, Valerie Toquin, Emilia Hilz, Roland Beffa, and Luigi Di Vietro
27 Melanin Biosynthesis Inhibitors 1003
Hiroyuki Hagiwara, Takahiro Hamada, and Shinichi Banba
28 Modern Powdery Mildew Fungicides 1023
Jochen Dietz and Christian Winter
29 Newest Aspects of Nucleic Acid Synthesis Inhibitors - Metalaxyl-M 1039
Helge Sierotzki, Laura Quaranta, Stefano Torriani, Ulrich Gisi, and Urs Mueller
30 Host Defense Inducers 1051
Valerie Toquin, Christoph A. Braun, Catherine Sirven, Lutz Assmann, Jeremy Dufour, Stefan Hillebrand, and Emilia Hilz
31 Oxysterol-Binding Protein Inhibitors 1075
Clemens Lamberth
32 Quinofumelin and Other Dihydroorotate Dehydrogenase Inhibitors 1085
Shinichi Banba, Hiroyuki Ito, and Norikazu Higashimura
33 Pyridachlometyl and Other Tubulin Dynamics Modulators 1099
Yuichi Matsuzaki, Hiroshi Ikegami, Tadafumi Matsunaga, and Akio Manabe
34 Aminopyrifen and Other GPI-anchored Wall Transfer Protein Inhibitors 1111
Masahiro Hatamoto and Ryo Aizawa
35 Fungicides with Unknown Mode of Action 1125
Clemens Lamberth
Index 1135
Volume 3a
Preface to the Fourth Edition xxv
Part III Insecticides 1147
Overview 1149
Peter Jeschke
36 IRAC: Insecticide Resistance and Mode of Action Classification of Insecticides 1155
Ralf Nauen, Russell Slater, Thomas C. Sparks, Alfred Elbert, and Alan McCaffery
37 Insect Molting and Metamorphosis 1173
37.1 Molting Disruptors, Dipteran: Cyromazine 1173
Yeshua Sempere Molina and Sven Geibel
37.2 Ecdysone Receptor Agonists: Diacylhydrazines 1178
Luis E. Gomez, Tarlochan Singh Dhadialla, and Ronald Ross Jr
37.3 Juvenil Hormone Receptor Modulators: Pyriproxyfen 1221
Makoto Hatakoshi and Katsuya Natsuhara
38 Chitin Biosynthesis 1237
38.1 Chitin Structure and Biosynthesis 1237
Sven Geibel, Neil A. Spomer, Joel J. Sheets, and Yeshua Sempere
38.2 Inhibitors of Chitin Biosynthesis Affecting CHS1 1243
Yeshua Sempere Molina, Neil A. Spomer, Joel J. Sheets, and Sven Geibel
38.3 Inhibitors of Chitin Biosynthesis, Type 1: Buprofezin 1252
Yeshua Sempere and Sven Geibel
38.4 Mite Growth Inhibitors Affecting CHS1: Clofentezine, Hexythiazox, and Etoxazole 1257
Ralf Nauen and Thomas Bretschneider
39 Microbial Disruptors of Insect Midgut Membranes 1275
Jeroen Van Rie
40 Metabolic Processes 1313
40.1 Inhibitors of Oxidative Phosphorylation 1313
Fergus Earley
40.1.1 Inhibitors of Mitochondrial ATP Synthase 1314
Fergus Earley, Roger Hall, and Josef Ehrenfreund
40.2 Uncouplers of Oxidative Phosphorylation via Disruption of the Proton the Gradient 1326
David Kuhn, Nigel Armes, and Catia Sazaki
40.3 Inhibitors of Mitochondrial Electron Transport: Acaricides and Insecticides 1333
Peter Luemmen, Thomas C. Sparks, Carl V. DeAmicis, Mark A. Dekeyser, Takashi Furuya, Motofumi Nakano, Shinsuke Fujioka, and Kozo Machiya
40.3.1 Introduction: The Mitochondrial Respiratory Chain 1333
40.3.2 Mitochondrial Complex I Electron Transport Inhibitors 1335
40.3.3 Mitochondrial Complex II Electron Transport Inhibitors 1344
40.3.3.4 Pyflubumide 1350
Takashi Furuya, Motofumi Nakano, Shinsuke Fujioka, and Kozo Machiya
40.3.3.5 Binding Modes, Target-Site Mutations, and Species Selectivity of Complex II Inhibitors 1361
40.3.4 Mitochondrial Complex III Electron Transport Inhibitors 1363
40.3.5 Mitochondrial Complex III Electron Transport Inhibitors - Qi site: Flometoquin 1372
Takeru Kobayashi, Ryo Horikoshi, and Andrew J. Crossthwaite
40.4 Inhibitors of Acetyl-CoA-Carboxylase 1379
Peter Jeschke, Reiner Fischer, and Ralf Nauen
40.4.1 Introduction 1379
40.4.2 Taget Site Mutations of Acetyl-CoA-Carboxylase 1380
40.4.3 Tetronic Acid Derivatives: Spirodiclofen and Spiromesifen 1383
Peter Jeschke, Reiner Fischer, and Ralf Nauen
40.4.4 Tetramic Acid Derivatives: Spirotetramat 1397
Peter Jeschke, Reiner Fischer, and Ralf Nauen
40.4.5 Tetramic Acid Derivatives: Spiropidion 1408
Anke Buchholz and Michel Muehlebach
40.4.6 Tetramic Acid Derivatives: Spidoxamat 1421
Reiner Fischer, Christian Marienhagen, and Ralf Nauen
41 Nervous System 1429
41.1 Nicotinic Acetylcholine Receptor Competitive Modulators, Allosteric Modulators, and Channel Blockers: Target and Selectivity Aspects 1429
Peter Jeschke, Ralf Nauen, and Michael Edmund Beck
41.2 Chemical Structural Features of Nicotinic Acetylcholine Receptor Competitive Modulators 1481
Peter Jeschke
41.2.1 Introduction 1481
41.2.2 Active Ingredients of the IRAC MoA Subgroup 4A 1482
41.2.3 Active Ingredients of the IRAC MoA Subgroups 4C to 4E 1485
41.2.4 Neonicotinoids 1487
41.2.4.1 Noncyclic Neonicotinoids 1487
Peter Jeschke
41.2.4.2 Five-Membered Heterocycles: Imidacloprid and Thiacloprid 1517
Peter Jeschke and Koichi Moriya
41.2.4.3 Six-Membered Heterocycles: Thiamethoxam and AKD 1022 1537
Peter Maienfisch
41.2.5 Sulfoximines: Sulfoxaflor 1566
Thomas C. Sparks, Michael R. Loso, Trent Perry, Frank J. Wessels, Ann M. Buysse, Benjamin M. Nugent, Vincent J. Kramer, Luis E. Gomez, Imre Mezei, David G.J. Mann, Nick X. Wang, and Gerald B. Watson
Volume 3b
Preface to the Fourth Edition xxvii
41.2.6 Butenolides: Flupyradifurone 1599
Peter Jeschke, Ralf Nauen, Robert Velten, Michael E. Beck, Matthias Haas, Christian Funke, and Georg Raupach
41.2.7 Mesoionics 1626
41.2.7.1 Triflumezopyrim 1626
Daniel Cordova, Wenming Zhang, Caleb W. Holyoke Jr, James D. Barry, Vineet Singh, Isaac B. Annan, Luis A.F. Teixeira, and John L. Andreassi
41.2.7.2 Fenmezoditiaz 1642
Joachim Dickhaut, Martin Weisel, Huazhang Huang, Lixin Mao, Barbara Wedel, Colin Ehnes, and Kai Ristau
41.2.8 Pyridinylidenes: Flupyrimin 1651
Ryo Horikoshi, Takehito Terajima, Kenji Shimomura, and Motohiro Tomizawa
41.3 Nicotinic Acetylcholine Receptor Allosteric Modulators - Site I: Spinosyns 1659
Thomas C. Sparks, Natalie C. Giampietro, Trent Perry, Frank Wessels, David G.J. Mann, Babu Raman, John Daeuble, M. Paige Oliver, Gary D. Crouse, Gerald B. Watson, James E. Dripps, and Imre Mezei
41.4 Nicotinic Acetylcholine Receptor Allosteric Modulators - Site II: GS-Omega/Kappa HxTx-Hv1a Peptide 1687
Dara G. Stockton
41.5 Sodium Channel Modulators 1702
Peter Jeschke
41.6 Voltage-dependent Sodium Channel Blockers 1718
41.6.1 Oxadiazines: Indoxacarb 1718
Stephen F. McCann, Daniel Cordova, John T. Andaloro, and George P. Lahm
41.6.2 Semicarbazone: Metaflumizone 1734
David Kuhn, Kazuhiro Takagi, Tomokazu Hino, Nigel Armes, and Desiree Hodges
41.7 GABA-gated Chloride Channel Blockers 1744
41.7.1 Phenylpyrazoles: Ethiprole and Fipronil 1744
Vincent L. Salgado, Keith A. Holmes, Lixin Mao, and Stefan Schnatterer
41.8 GABA-gated Chloride Channel Allosteric Modulators 1782
41.8.1 Meta-diamides: Broflanilide 1782
Toshifumi Nakao and Shinichi Banba
41.8.2 Isoxazolines: Fluxametamide 1791
Takeshi Mita, Yuki Furukawa, Motoyoshi Iwasa, Takamasa Kikuchi, Miho Asahi, and Mitsuaki Komoda
41.8.3 Isoxazolines: Isocycloseram 1801
Jerome Cassayre and Myriem El Qacemi
41.9 Glutamate-gated Chloride Channel Allosteric Modulators: Avermectins and Milbemycins 1815
Ottmar Franz Hueter and Thomas Pitterna
42 Chordotonal Organ TRPV Channel Modulators 1839
42.1 Pyridine Azomethine Derivatives: Pymetrozine and Pyrifluquinazon 1839
Peter Maienfisch
42.2 Pyropenes: Afidopyropen 1856
Desiree M. Hodges, Anna K. Hoffarth, Ryo Horikoshi, Christopher Koradin, James Machamer, Christoph Schissler, Toshiaki Sunazuka, Robert R. Svadlenak, and Siddharth Tiwari
42.3 Indazapyroxamet 1868
Wenming Zhang, Daniel Cordova, Jason Hamm, Billy Annan, David Clark, and Suobao Rong
43 Chordotonal Organ Modulators 1879
43.1 Chordotonal Organ Nicotinamidase Inhibitors: Flonicamid 1879
Peter Maienfisch
43.2 Chordotonal Organ Modulators - Undefined Target Site: Dimpropyridaz 1890
Barbara Wedel, Desiree Hodges, and Karsten Koerber
44 New Unknown Mode of Action 1899
44.1 Pyridalyl 1899
Shigeru Saito and Noriyasu Sakamoto
44.2 Benzpyrimoxan 1906
Eikoh Satoh
45 Insecticides Affecting Calcium Homeostasis 1913
45.1 Ryanodine Receptor Modulators: Diamides 1913
Peter Luemmen, Ulrich Ebbinghaus-Kintscher, Takao Masaki, Hiroshi Hamaguchi, and Takashi Hirooka
45.2 Phthalic Acid Diamide: Flubendiamide 1923
Ulrich Ebbinghaus-Kintscher, Peter Luemmen, Takao Masaki, Hiroshi Hamaguchi, and Takashi Hirooka
45.3 Anthranilic Diamides: Chlorantraniliprole and Cyantraniliprole 1929
George P. Lahm, Daniel Cordova, James D. Barry, John T. Andaloro, Isaac B. Annan, Paula C. Marcon, Hector E. Portillo, Luis A. Teixeira, Thomas M. Stevenson, and Thomas P. Selby
45.4 Anthranilic Diamide: Cyclaniliprole 1949
Masamitsu Tsukamoto, Taku Hamamoto, Satoko Fujii, Chiaki Takeda, Yusuke Kumakura, and Masayuki Morita
45.5 Anthranilic Diamide: Tetraniliprole 1960
Ruediger Fischer, Christian Funke, Sergii Pazenok, and Matthieu Willot
46 Vesicular Acetylcholine Transporter Inhibitors 1975
46.1 Oxazosulfyl 1975
Mai Ito, Shinya Nishimura, and Yoshihiko Nokura
47 Nematicides 1979
47.1 IRAC: Nematicide Mode of Action Classification 1979
Peter Maienfisch
47.2 Mitochondrial Complex II Electron Transport Inhibitors - Succinate-coenzyme Q Reductase 2010
47.2.1 Fluopyram 2010
Peter Luemmen, Svenja Bellof, and Helmut Fuersch
47.2.2 Cyclobutrifluram 2023
Olivier Loiseleur, Anthony Flemming, Torsten Luksch, Brigitte Slaats, Matthias Gaberthueel, Marcus Guest, and Richard Currie
47.3 Compounds of Unknown or Uncertain Mode of Action 2037
47.3.1 Fluazaindolizine 2037
George P. Lahm, John A. Wiles, Daniel Cordova, Tim Thoden, Johan Desaeger, Ben K. Smith, Thomas F. Pahutski, Michel A. Rivera, Tony Meloro, Roman Kucharczyk, Renee M. Lett, Anne Daly, and Brenton T. Smith
47.3.2 Fluazaindolizine (Addendum) 2047
Tim Thoden, John A. Wiles, Chaoxian Geng, and Timothy Wilson
Index 2051
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Agrochemicals; herbicides; fungicides; insecticides; crop protection compounds; chemical synthesis; physicochemical properties; structure-activity relationship; mode of action; safety profile; resistance management; 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
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 Inhibitors: N-Phenethylamides 827
Clemens Lamberth
20.3.4 Succinate Dehydrogenase Inhibitors: N-Pyridinylethylamides 837
Andreas Mehl, Jochen Kleemann, Heiko Rieck, and Pierre-Yves Coqueron
20.4 Uncouplers of Oxidative Phosphorylation 847
William G. Whittingham
21 Fungicides Acting on Amino Acids and Protein Synthesis: Anilinopyrimidines - Assumed Methionine Biosynthesis Inhibitors 869
Ulrich Gisi, Urs Mueller, and Samantha Hall
22 Fungicides Acting on Signal Transduction 881
22.1 Mode of Action of Fludioxonil, Fenpiclonil, and Quinoxyfen 881
Andrew Corran
22.2 Chemistry and Biology of Fludioxonil, Fenpiclonil, and Quinoxyfen 888
Gertrude Knauf-Beiter, Ronald Zeun, and Clemens Lamberth
23 Fungicides Acting on Mitosis and Cell Division: Zoxamide, an Antitubulin Fungicide for Control of Oomycete Pathogens 907
David H. Young
24 Sterol Biosynthesis Inhibitors 917
Andreas Mehl, Klaus Stenzel, David Bernier, and Jean-Pierre Vors
25 Carboxylic Acid Amide (CAA) Fungicides 973
Mathias Blum, Ulrich Gisi, Clemens Lamberth, Andreas Mehl, and Thomas Seitz
26 Fluopicolide: Anti-oomycete Fungicide with a Unique Mode of Action 995
Bernd Essigmann, Jochen Kleemann, Marie-Pascale Latorse, Valerie Toquin, Emilia Hilz, Roland Beffa, and Luigi Di Vietro
27 Melanin Biosynthesis Inhibitors 1003
Hiroyuki Hagiwara, Takahiro Hamada, and Shinichi Banba
28 Modern Powdery Mildew Fungicides 1023
Jochen Dietz and Christian Winter
29 Newest Aspects of Nucleic Acid Synthesis Inhibitors - Metalaxyl-M 1039
Helge Sierotzki, Laura Quaranta, Stefano Torriani, Ulrich Gisi, and Urs Mueller
30 Host Defense Inducers 1051
Valerie Toquin, Christoph A. Braun, Catherine Sirven, Lutz Assmann, Jeremy Dufour, Stefan Hillebrand, and Emilia Hilz
31 Oxysterol-Binding Protein Inhibitors 1075
Clemens Lamberth
32 Quinofumelin and Other Dihydroorotate Dehydrogenase Inhibitors 1085
Shinichi Banba, Hiroyuki Ito, and Norikazu Higashimura
33 Pyridachlometyl and Other Tubulin Dynamics Modulators 1099
Yuichi Matsuzaki, Hiroshi Ikegami, Tadafumi Matsunaga, and Akio Manabe
34 Aminopyrifen and Other GPI-anchored Wall Transfer Protein Inhibitors 1111
Masahiro Hatamoto and Ryo Aizawa
35 Fungicides with Unknown Mode of Action 1125
Clemens Lamberth
Index 1135
Volume 3a
Preface to the Fourth Edition xxv
Part III Insecticides 1147
Overview 1149
Peter Jeschke
36 IRAC: Insecticide Resistance and Mode of Action Classification of Insecticides 1155
Ralf Nauen, Russell Slater, Thomas C. Sparks, Alfred Elbert, and Alan McCaffery
37 Insect Molting and Metamorphosis 1173
37.1 Molting Disruptors, Dipteran: Cyromazine 1173
Yeshua Sempere Molina and Sven Geibel
37.2 Ecdysone Receptor Agonists: Diacylhydrazines 1178
Luis E. Gomez, Tarlochan Singh Dhadialla, and Ronald Ross Jr
37.3 Juvenil Hormone Receptor Modulators: Pyriproxyfen 1221
Makoto Hatakoshi and Katsuya Natsuhara
38 Chitin Biosynthesis 1237
38.1 Chitin Structure and Biosynthesis 1237
Sven Geibel, Neil A. Spomer, Joel J. Sheets, and Yeshua Sempere
38.2 Inhibitors of Chitin Biosynthesis Affecting CHS1 1243
Yeshua Sempere Molina, Neil A. Spomer, Joel J. Sheets, and Sven Geibel
38.3 Inhibitors of Chitin Biosynthesis, Type 1: Buprofezin 1252
Yeshua Sempere and Sven Geibel
38.4 Mite Growth Inhibitors Affecting CHS1: Clofentezine, Hexythiazox, and Etoxazole 1257
Ralf Nauen and Thomas Bretschneider
39 Microbial Disruptors of Insect Midgut Membranes 1275
Jeroen Van Rie
40 Metabolic Processes 1313
40.1 Inhibitors of Oxidative Phosphorylation 1313
Fergus Earley
40.1.1 Inhibitors of Mitochondrial ATP Synthase 1314
Fergus Earley, Roger Hall, and Josef Ehrenfreund
40.2 Uncouplers of Oxidative Phosphorylation via Disruption of the Proton the Gradient 1326
David Kuhn, Nigel Armes, and Catia Sazaki
40.3 Inhibitors of Mitochondrial Electron Transport: Acaricides and Insecticides 1333
Peter Luemmen, Thomas C. Sparks, Carl V. DeAmicis, Mark A. Dekeyser, Takashi Furuya, Motofumi Nakano, Shinsuke Fujioka, and Kozo Machiya
40.3.1 Introduction: The Mitochondrial Respiratory Chain 1333
40.3.2 Mitochondrial Complex I Electron Transport Inhibitors 1335
40.3.3 Mitochondrial Complex II Electron Transport Inhibitors 1344
40.3.3.4 Pyflubumide 1350
Takashi Furuya, Motofumi Nakano, Shinsuke Fujioka, and Kozo Machiya
40.3.3.5 Binding Modes, Target-Site Mutations, and Species Selectivity of Complex II Inhibitors 1361
40.3.4 Mitochondrial Complex III Electron Transport Inhibitors 1363
40.3.5 Mitochondrial Complex III Electron Transport Inhibitors - Qi site: Flometoquin 1372
Takeru Kobayashi, Ryo Horikoshi, and Andrew J. Crossthwaite
40.4 Inhibitors of Acetyl-CoA-Carboxylase 1379
Peter Jeschke, Reiner Fischer, and Ralf Nauen
40.4.1 Introduction 1379
40.4.2 Taget Site Mutations of Acetyl-CoA-Carboxylase 1380
40.4.3 Tetronic Acid Derivatives: Spirodiclofen and Spiromesifen 1383
Peter Jeschke, Reiner Fischer, and Ralf Nauen
40.4.4 Tetramic Acid Derivatives: Spirotetramat 1397
Peter Jeschke, Reiner Fischer, and Ralf Nauen
40.4.5 Tetramic Acid Derivatives: Spiropidion 1408
Anke Buchholz and Michel Muehlebach
40.4.6 Tetramic Acid Derivatives: Spidoxamat 1421
Reiner Fischer, Christian Marienhagen, and Ralf Nauen
41 Nervous System 1429
41.1 Nicotinic Acetylcholine Receptor Competitive Modulators, Allosteric Modulators, and Channel Blockers: Target and Selectivity Aspects 1429
Peter Jeschke, Ralf Nauen, and Michael Edmund Beck
41.2 Chemical Structural Features of Nicotinic Acetylcholine Receptor Competitive Modulators 1481
Peter Jeschke
41.2.1 Introduction 1481
41.2.2 Active Ingredients of the IRAC MoA Subgroup 4A 1482
41.2.3 Active Ingredients of the IRAC MoA Subgroups 4C to 4E 1485
41.2.4 Neonicotinoids 1487
41.2.4.1 Noncyclic Neonicotinoids 1487
Peter Jeschke
41.2.4.2 Five-Membered Heterocycles: Imidacloprid and Thiacloprid 1517
Peter Jeschke and Koichi Moriya
41.2.4.3 Six-Membered Heterocycles: Thiamethoxam and AKD 1022 1537
Peter Maienfisch
41.2.5 Sulfoximines: Sulfoxaflor 1566
Thomas C. Sparks, Michael R. Loso, Trent Perry, Frank J. Wessels, Ann M. Buysse, Benjamin M. Nugent, Vincent J. Kramer, Luis E. Gomez, Imre Mezei, David G.J. Mann, Nick X. Wang, and Gerald B. Watson
Volume 3b
Preface to the Fourth Edition xxvii
41.2.6 Butenolides: Flupyradifurone 1599
Peter Jeschke, Ralf Nauen, Robert Velten, Michael E. Beck, Matthias Haas, Christian Funke, and Georg Raupach
41.2.7 Mesoionics 1626
41.2.7.1 Triflumezopyrim 1626
Daniel Cordova, Wenming Zhang, Caleb W. Holyoke Jr, James D. Barry, Vineet Singh, Isaac B. Annan, Luis A.F. Teixeira, and John L. Andreassi
41.2.7.2 Fenmezoditiaz 1642
Joachim Dickhaut, Martin Weisel, Huazhang Huang, Lixin Mao, Barbara Wedel, Colin Ehnes, and Kai Ristau
41.2.8 Pyridinylidenes: Flupyrimin 1651
Ryo Horikoshi, Takehito Terajima, Kenji Shimomura, and Motohiro Tomizawa
41.3 Nicotinic Acetylcholine Receptor Allosteric Modulators - Site I: Spinosyns 1659
Thomas C. Sparks, Natalie C. Giampietro, Trent Perry, Frank Wessels, David G.J. Mann, Babu Raman, John Daeuble, M. Paige Oliver, Gary D. Crouse, Gerald B. Watson, James E. Dripps, and Imre Mezei
41.4 Nicotinic Acetylcholine Receptor Allosteric Modulators - Site II: GS-Omega/Kappa HxTx-Hv1a Peptide 1687
Dara G. Stockton
41.5 Sodium Channel Modulators 1702
Peter Jeschke
41.6 Voltage-dependent Sodium Channel Blockers 1718
41.6.1 Oxadiazines: Indoxacarb 1718
Stephen F. McCann, Daniel Cordova, John T. Andaloro, and George P. Lahm
41.6.2 Semicarbazone: Metaflumizone 1734
David Kuhn, Kazuhiro Takagi, Tomokazu Hino, Nigel Armes, and Desiree Hodges
41.7 GABA-gated Chloride Channel Blockers 1744
41.7.1 Phenylpyrazoles: Ethiprole and Fipronil 1744
Vincent L. Salgado, Keith A. Holmes, Lixin Mao, and Stefan Schnatterer
41.8 GABA-gated Chloride Channel Allosteric Modulators 1782
41.8.1 Meta-diamides: Broflanilide 1782
Toshifumi Nakao and Shinichi Banba
41.8.2 Isoxazolines: Fluxametamide 1791
Takeshi Mita, Yuki Furukawa, Motoyoshi Iwasa, Takamasa Kikuchi, Miho Asahi, and Mitsuaki Komoda
41.8.3 Isoxazolines: Isocycloseram 1801
Jerome Cassayre and Myriem El Qacemi
41.9 Glutamate-gated Chloride Channel Allosteric Modulators: Avermectins and Milbemycins 1815
Ottmar Franz Hueter and Thomas Pitterna
42 Chordotonal Organ TRPV Channel Modulators 1839
42.1 Pyridine Azomethine Derivatives: Pymetrozine and Pyrifluquinazon 1839
Peter Maienfisch
42.2 Pyropenes: Afidopyropen 1856
Desiree M. Hodges, Anna K. Hoffarth, Ryo Horikoshi, Christopher Koradin, James Machamer, Christoph Schissler, Toshiaki Sunazuka, Robert R. Svadlenak, and Siddharth Tiwari
42.3 Indazapyroxamet 1868
Wenming Zhang, Daniel Cordova, Jason Hamm, Billy Annan, David Clark, and Suobao Rong
43 Chordotonal Organ Modulators 1879
43.1 Chordotonal Organ Nicotinamidase Inhibitors: Flonicamid 1879
Peter Maienfisch
43.2 Chordotonal Organ Modulators - Undefined Target Site: Dimpropyridaz 1890
Barbara Wedel, Desiree Hodges, and Karsten Koerber
44 New Unknown Mode of Action 1899
44.1 Pyridalyl 1899
Shigeru Saito and Noriyasu Sakamoto
44.2 Benzpyrimoxan 1906
Eikoh Satoh
45 Insecticides Affecting Calcium Homeostasis 1913
45.1 Ryanodine Receptor Modulators: Diamides 1913
Peter Luemmen, Ulrich Ebbinghaus-Kintscher, Takao Masaki, Hiroshi Hamaguchi, and Takashi Hirooka
45.2 Phthalic Acid Diamide: Flubendiamide 1923
Ulrich Ebbinghaus-Kintscher, Peter Luemmen, Takao Masaki, Hiroshi Hamaguchi, and Takashi Hirooka
45.3 Anthranilic Diamides: Chlorantraniliprole and Cyantraniliprole 1929
George P. Lahm, Daniel Cordova, James D. Barry, John T. Andaloro, Isaac B. Annan, Paula C. Marcon, Hector E. Portillo, Luis A. Teixeira, Thomas M. Stevenson, and Thomas P. Selby
45.4 Anthranilic Diamide: Cyclaniliprole 1949
Masamitsu Tsukamoto, Taku Hamamoto, Satoko Fujii, Chiaki Takeda, Yusuke Kumakura, and Masayuki Morita
45.5 Anthranilic Diamide: Tetraniliprole 1960
Ruediger Fischer, Christian Funke, Sergii Pazenok, and Matthieu Willot
46 Vesicular Acetylcholine Transporter Inhibitors 1975
46.1 Oxazosulfyl 1975
Mai Ito, Shinya Nishimura, and Yoshihiko Nokura
47 Nematicides 1979
47.1 IRAC: Nematicide Mode of Action Classification 1979
Peter Maienfisch
47.2 Mitochondrial Complex II Electron Transport Inhibitors - Succinate-coenzyme Q Reductase 2010
47.2.1 Fluopyram 2010
Peter Luemmen, Svenja Bellof, and Helmut Fuersch
47.2.2 Cyclobutrifluram 2023
Olivier Loiseleur, Anthony Flemming, Torsten Luksch, Brigitte Slaats, Matthias Gaberthueel, Marcus Guest, and Richard Currie
47.3 Compounds of Unknown or Uncertain Mode of Action 2037
47.3.1 Fluazaindolizine 2037
George P. Lahm, John A. Wiles, Daniel Cordova, Tim Thoden, Johan Desaeger, Ben K. Smith, Thomas F. Pahutski, Michel A. Rivera, Tony Meloro, Roman Kucharczyk, Renee M. Lett, Anne Daly, and Brenton T. Smith
47.3.2 Fluazaindolizine (Addendum) 2047
Tim Thoden, John A. Wiles, Chaoxian Geng, and Timothy Wilson
Index 2051
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
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 Inhibitors: N-Phenethylamides 827
Clemens Lamberth
20.3.4 Succinate Dehydrogenase Inhibitors: N-Pyridinylethylamides 837
Andreas Mehl, Jochen Kleemann, Heiko Rieck, and Pierre-Yves Coqueron
20.4 Uncouplers of Oxidative Phosphorylation 847
William G. Whittingham
21 Fungicides Acting on Amino Acids and Protein Synthesis: Anilinopyrimidines - Assumed Methionine Biosynthesis Inhibitors 869
Ulrich Gisi, Urs Mueller, and Samantha Hall
22 Fungicides Acting on Signal Transduction 881
22.1 Mode of Action of Fludioxonil, Fenpiclonil, and Quinoxyfen 881
Andrew Corran
22.2 Chemistry and Biology of Fludioxonil, Fenpiclonil, and Quinoxyfen 888
Gertrude Knauf-Beiter, Ronald Zeun, and Clemens Lamberth
23 Fungicides Acting on Mitosis and Cell Division: Zoxamide, an Antitubulin Fungicide for Control of Oomycete Pathogens 907
David H. Young
24 Sterol Biosynthesis Inhibitors 917
Andreas Mehl, Klaus Stenzel, David Bernier, and Jean-Pierre Vors
25 Carboxylic Acid Amide (CAA) Fungicides 973
Mathias Blum, Ulrich Gisi, Clemens Lamberth, Andreas Mehl, and Thomas Seitz
26 Fluopicolide: Anti-oomycete Fungicide with a Unique Mode of Action 995
Bernd Essigmann, Jochen Kleemann, Marie-Pascale Latorse, Valerie Toquin, Emilia Hilz, Roland Beffa, and Luigi Di Vietro
27 Melanin Biosynthesis Inhibitors 1003
Hiroyuki Hagiwara, Takahiro Hamada, and Shinichi Banba
28 Modern Powdery Mildew Fungicides 1023
Jochen Dietz and Christian Winter
29 Newest Aspects of Nucleic Acid Synthesis Inhibitors - Metalaxyl-M 1039
Helge Sierotzki, Laura Quaranta, Stefano Torriani, Ulrich Gisi, and Urs Mueller
30 Host Defense Inducers 1051
Valerie Toquin, Christoph A. Braun, Catherine Sirven, Lutz Assmann, Jeremy Dufour, Stefan Hillebrand, and Emilia Hilz
31 Oxysterol-Binding Protein Inhibitors 1075
Clemens Lamberth
32 Quinofumelin and Other Dihydroorotate Dehydrogenase Inhibitors 1085
Shinichi Banba, Hiroyuki Ito, and Norikazu Higashimura
33 Pyridachlometyl and Other Tubulin Dynamics Modulators 1099
Yuichi Matsuzaki, Hiroshi Ikegami, Tadafumi Matsunaga, and Akio Manabe
34 Aminopyrifen and Other GPI-anchored Wall Transfer Protein Inhibitors 1111
Masahiro Hatamoto and Ryo Aizawa
35 Fungicides with Unknown Mode of Action 1125
Clemens Lamberth
Index 1135
Volume 3a
Preface to the Fourth Edition xxv
Part III Insecticides 1147
Overview 1149
Peter Jeschke
36 IRAC: Insecticide Resistance and Mode of Action Classification of Insecticides 1155
Ralf Nauen, Russell Slater, Thomas C. Sparks, Alfred Elbert, and Alan McCaffery
37 Insect Molting and Metamorphosis 1173
37.1 Molting Disruptors, Dipteran: Cyromazine 1173
Yeshua Sempere Molina and Sven Geibel
37.2 Ecdysone Receptor Agonists: Diacylhydrazines 1178
Luis E. Gomez, Tarlochan Singh Dhadialla, and Ronald Ross Jr
37.3 Juvenil Hormone Receptor Modulators: Pyriproxyfen 1221
Makoto Hatakoshi and Katsuya Natsuhara
38 Chitin Biosynthesis 1237
38.1 Chitin Structure and Biosynthesis 1237
Sven Geibel, Neil A. Spomer, Joel J. Sheets, and Yeshua Sempere
38.2 Inhibitors of Chitin Biosynthesis Affecting CHS1 1243
Yeshua Sempere Molina, Neil A. Spomer, Joel J. Sheets, and Sven Geibel
38.3 Inhibitors of Chitin Biosynthesis, Type 1: Buprofezin 1252
Yeshua Sempere and Sven Geibel
38.4 Mite Growth Inhibitors Affecting CHS1: Clofentezine, Hexythiazox, and Etoxazole 1257
Ralf Nauen and Thomas Bretschneider
39 Microbial Disruptors of Insect Midgut Membranes 1275
Jeroen Van Rie
40 Metabolic Processes 1313
40.1 Inhibitors of Oxidative Phosphorylation 1313
Fergus Earley
40.1.1 Inhibitors of Mitochondrial ATP Synthase 1314
Fergus Earley, Roger Hall, and Josef Ehrenfreund
40.2 Uncouplers of Oxidative Phosphorylation via Disruption of the Proton the Gradient 1326
David Kuhn, Nigel Armes, and Catia Sazaki
40.3 Inhibitors of Mitochondrial Electron Transport: Acaricides and Insecticides 1333
Peter Luemmen, Thomas C. Sparks, Carl V. DeAmicis, Mark A. Dekeyser, Takashi Furuya, Motofumi Nakano, Shinsuke Fujioka, and Kozo Machiya
40.3.1 Introduction: The Mitochondrial Respiratory Chain 1333
40.3.2 Mitochondrial Complex I Electron Transport Inhibitors 1335
40.3.3 Mitochondrial Complex II Electron Transport Inhibitors 1344
40.3.3.4 Pyflubumide 1350
Takashi Furuya, Motofumi Nakano, Shinsuke Fujioka, and Kozo Machiya
40.3.3.5 Binding Modes, Target-Site Mutations, and Species Selectivity of Complex II Inhibitors 1361
40.3.4 Mitochondrial Complex III Electron Transport Inhibitors 1363
40.3.5 Mitochondrial Complex III Electron Transport Inhibitors - Qi site: Flometoquin 1372
Takeru Kobayashi, Ryo Horikoshi, and Andrew J. Crossthwaite
40.4 Inhibitors of Acetyl-CoA-Carboxylase 1379
Peter Jeschke, Reiner Fischer, and Ralf Nauen
40.4.1 Introduction 1379
40.4.2 Taget Site Mutations of Acetyl-CoA-Carboxylase 1380
40.4.3 Tetronic Acid Derivatives: Spirodiclofen and Spiromesifen 1383
Peter Jeschke, Reiner Fischer, and Ralf Nauen
40.4.4 Tetramic Acid Derivatives: Spirotetramat 1397
Peter Jeschke, Reiner Fischer, and Ralf Nauen
40.4.5 Tetramic Acid Derivatives: Spiropidion 1408
Anke Buchholz and Michel Muehlebach
40.4.6 Tetramic Acid Derivatives: Spidoxamat 1421
Reiner Fischer, Christian Marienhagen, and Ralf Nauen
41 Nervous System 1429
41.1 Nicotinic Acetylcholine Receptor Competitive Modulators, Allosteric Modulators, and Channel Blockers: Target and Selectivity Aspects 1429
Peter Jeschke, Ralf Nauen, and Michael Edmund Beck
41.2 Chemical Structural Features of Nicotinic Acetylcholine Receptor Competitive Modulators 1481
Peter Jeschke
41.2.1 Introduction 1481
41.2.2 Active Ingredients of the IRAC MoA Subgroup 4A 1482
41.2.3 Active Ingredients of the IRAC MoA Subgroups 4C to 4E 1485
41.2.4 Neonicotinoids 1487
41.2.4.1 Noncyclic Neonicotinoids 1487
Peter Jeschke
41.2.4.2 Five-Membered Heterocycles: Imidacloprid and Thiacloprid 1517
Peter Jeschke and Koichi Moriya
41.2.4.3 Six-Membered Heterocycles: Thiamethoxam and AKD 1022 1537
Peter Maienfisch
41.2.5 Sulfoximines: Sulfoxaflor 1566
Thomas C. Sparks, Michael R. Loso, Trent Perry, Frank J. Wessels, Ann M. Buysse, Benjamin M. Nugent, Vincent J. Kramer, Luis E. Gomez, Imre Mezei, David G.J. Mann, Nick X. Wang, and Gerald B. Watson
Volume 3b
Preface to the Fourth Edition xxvii
41.2.6 Butenolides: Flupyradifurone 1599
Peter Jeschke, Ralf Nauen, Robert Velten, Michael E. Beck, Matthias Haas, Christian Funke, and Georg Raupach
41.2.7 Mesoionics 1626
41.2.7.1 Triflumezopyrim 1626
Daniel Cordova, Wenming Zhang, Caleb W. Holyoke Jr, James D. Barry, Vineet Singh, Isaac B. Annan, Luis A.F. Teixeira, and John L. Andreassi
41.2.7.2 Fenmezoditiaz 1642
Joachim Dickhaut, Martin Weisel, Huazhang Huang, Lixin Mao, Barbara Wedel, Colin Ehnes, and Kai Ristau
41.2.8 Pyridinylidenes: Flupyrimin 1651
Ryo Horikoshi, Takehito Terajima, Kenji Shimomura, and Motohiro Tomizawa
41.3 Nicotinic Acetylcholine Receptor Allosteric Modulators - Site I: Spinosyns 1659
Thomas C. Sparks, Natalie C. Giampietro, Trent Perry, Frank Wessels, David G.J. Mann, Babu Raman, John Daeuble, M. Paige Oliver, Gary D. Crouse, Gerald B. Watson, James E. Dripps, and Imre Mezei
41.4 Nicotinic Acetylcholine Receptor Allosteric Modulators - Site II: GS-Omega/Kappa HxTx-Hv1a Peptide 1687
Dara G. Stockton
41.5 Sodium Channel Modulators 1702
Peter Jeschke
41.6 Voltage-dependent Sodium Channel Blockers 1718
41.6.1 Oxadiazines: Indoxacarb 1718
Stephen F. McCann, Daniel Cordova, John T. Andaloro, and George P. Lahm
41.6.2 Semicarbazone: Metaflumizone 1734
David Kuhn, Kazuhiro Takagi, Tomokazu Hino, Nigel Armes, and Desiree Hodges
41.7 GABA-gated Chloride Channel Blockers 1744
41.7.1 Phenylpyrazoles: Ethiprole and Fipronil 1744
Vincent L. Salgado, Keith A. Holmes, Lixin Mao, and Stefan Schnatterer
41.8 GABA-gated Chloride Channel Allosteric Modulators 1782
41.8.1 Meta-diamides: Broflanilide 1782
Toshifumi Nakao and Shinichi Banba
41.8.2 Isoxazolines: Fluxametamide 1791
Takeshi Mita, Yuki Furukawa, Motoyoshi Iwasa, Takamasa Kikuchi, Miho Asahi, and Mitsuaki Komoda
41.8.3 Isoxazolines: Isocycloseram 1801
Jerome Cassayre and Myriem El Qacemi
41.9 Glutamate-gated Chloride Channel Allosteric Modulators: Avermectins and Milbemycins 1815
Ottmar Franz Hueter and Thomas Pitterna
42 Chordotonal Organ TRPV Channel Modulators 1839
42.1 Pyridine Azomethine Derivatives: Pymetrozine and Pyrifluquinazon 1839
Peter Maienfisch
42.2 Pyropenes: Afidopyropen 1856
Desiree M. Hodges, Anna K. Hoffarth, Ryo Horikoshi, Christopher Koradin, James Machamer, Christoph Schissler, Toshiaki Sunazuka, Robert R. Svadlenak, and Siddharth Tiwari
42.3 Indazapyroxamet 1868
Wenming Zhang, Daniel Cordova, Jason Hamm, Billy Annan, David Clark, and Suobao Rong
43 Chordotonal Organ Modulators 1879
43.1 Chordotonal Organ Nicotinamidase Inhibitors: Flonicamid 1879
Peter Maienfisch
43.2 Chordotonal Organ Modulators - Undefined Target Site: Dimpropyridaz 1890
Barbara Wedel, Desiree Hodges, and Karsten Koerber
44 New Unknown Mode of Action 1899
44.1 Pyridalyl 1899
Shigeru Saito and Noriyasu Sakamoto
44.2 Benzpyrimoxan 1906
Eikoh Satoh
45 Insecticides Affecting Calcium Homeostasis 1913
45.1 Ryanodine Receptor Modulators: Diamides 1913
Peter Luemmen, Ulrich Ebbinghaus-Kintscher, Takao Masaki, Hiroshi Hamaguchi, and Takashi Hirooka
45.2 Phthalic Acid Diamide: Flubendiamide 1923
Ulrich Ebbinghaus-Kintscher, Peter Luemmen, Takao Masaki, Hiroshi Hamaguchi, and Takashi Hirooka
45.3 Anthranilic Diamides: Chlorantraniliprole and Cyantraniliprole 1929
George P. Lahm, Daniel Cordova, James D. Barry, John T. Andaloro, Isaac B. Annan, Paula C. Marcon, Hector E. Portillo, Luis A. Teixeira, Thomas M. Stevenson, and Thomas P. Selby
45.4 Anthranilic Diamide: Cyclaniliprole 1949
Masamitsu Tsukamoto, Taku Hamamoto, Satoko Fujii, Chiaki Takeda, Yusuke Kumakura, and Masayuki Morita
45.5 Anthranilic Diamide: Tetraniliprole 1960
Ruediger Fischer, Christian Funke, Sergii Pazenok, and Matthieu Willot
46 Vesicular Acetylcholine Transporter Inhibitors 1975
46.1 Oxazosulfyl 1975
Mai Ito, Shinya Nishimura, and Yoshihiko Nokura
47 Nematicides 1979
47.1 IRAC: Nematicide Mode of Action Classification 1979
Peter Maienfisch
47.2 Mitochondrial Complex II Electron Transport Inhibitors - Succinate-coenzyme Q Reductase 2010
47.2.1 Fluopyram 2010
Peter Luemmen, Svenja Bellof, and Helmut Fuersch
47.2.2 Cyclobutrifluram 2023
Olivier Loiseleur, Anthony Flemming, Torsten Luksch, Brigitte Slaats, Matthias Gaberthueel, Marcus Guest, and Richard Currie
47.3 Compounds of Unknown or Uncertain Mode of Action 2037
47.3.1 Fluazaindolizine 2037
George P. Lahm, John A. Wiles, Daniel Cordova, Tim Thoden, Johan Desaeger, Ben K. Smith, Thomas F. Pahutski, Michel A. Rivera, Tony Meloro, Roman Kucharczyk, Renee M. Lett, Anne Daly, and Brenton T. Smith
47.3.2 Fluazaindolizine (Addendum) 2047
Tim Thoden, John A. Wiles, Chaoxian Geng, and Timothy Wilson
Index 2051
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