Modern Crop Protection Compounds, Volumes 3a and 3b

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 3aPreface to the Fourth Edition xxvPart III Insecticides 1147Overview 1149Peter Jeschke36 IRAC: Insecticide Resistance and Mode of Action Classification of Insecticides 1155Ralf Nauen, Russell Slater, Thomas C. Sparks, Alfred Elbert, and Alan McCaffery37 Insect Molting and Metamorphosis 117337.1 Molting Disruptors, Dipteran: Cyromazine 1173Yeshua Sempere Molina and Sven Geibel37.2 Ecdysone Receptor Agonists: Diacylhydrazines 1178Luis E. Gomez, Tarlochan Singh Dhadialla, and Ronald Ross Jr37.3 Juvenil Hormone Receptor Modulators: Pyriproxyfen 1221Makoto Hatakoshi and Katsuya Natsuhara38 Chitin Biosynthesis 123738.1 Chitin Structure and Biosynthesis 1237Sven Geibel, Neil A. Spomer, Joel J. Sheets, and Yeshua Sempere38.2 Inhibitors of Chitin Biosynthesis Affecting CHS1 1243Yeshua Sempere Molina, Neil A. Spomer, Joel J. Sheets, and Sven Geibel38.3 Inhibitors of Chitin Biosynthesis, Type 1: Buprofezin 1252Yeshua Sempere and Sven Geibel38.4 Mite Growth Inhibitors Affecting CHS1: Clofentezine, Hexythiazox, and Etoxazole 1257Ralf Nauen and Thomas Bretschneider39 Microbial Disruptors of Insect Midgut Membranes 1275Jeroen Van Rie40 Metabolic Processes 131340.1 Inhibitors of Oxidative Phosphorylation 1313Fergus Earley40.1.1 Inhibitors of Mitochondrial ATP Synthase 1314Fergus Earley, Roger Hall, and Josef Ehrenfreund40.2 Uncouplers of Oxidative Phosphorylation via Disruption of the Proton the Gradient 1326David Kuhn, Nigel Armes, and Catia Sazaki40.3 Inhibitors of Mitochondrial Electron Transport: Acaricides and Insecticides 1333Peter Lümmen, Thomas C. Sparks, Carl V. DeAmicis, Mark A. Dekeyser, Takashi Furuya, Motofumi Nakano, Shinsuke Fujioka, and Kozo Machiya40.3.1 Introduction: The Mitochondrial Respiratory Chain 133340.3.2 Mitochondrial Complex I Electron Transport Inhibitors 133540.3.3 Mitochondrial Complex II Electron Transport Inhibitors 134440.3.3.4 Pyflubumide 1350Takashi Furuya, Motofumi Nakano, Shinsuke Fujioka, and Kozo Machiya40.3.3.5 Binding Modes, Target-Site Mutations, and Species Selectivity of Complex II Inhibitors 136140.3.4 Mitochondrial Complex III Electron Transport Inhibitors 136340.3.5 Mitochondrial Complex III Electron Transport Inhibitors – Qi site: Flometoquin 1372Takeru Kobayashi, Ryo Horikoshi, and Andrew J. Crossthwaite40.4 Inhibitors of Acetyl-CoA-Carboxylase 1379Peter Jeschke, Reiner Fischer, and Ralf Nauen40.4.1 Introduction 137940.4.2 Taget Site Mutations of Acetyl-CoA-Carboxylase 138040.4.3 Tetronic Acid Derivatives: Spirodiclofen and Spiromesifen 1383Peter Jeschke, Reiner Fischer, and Ralf Nauen40.4.4 Tetramic Acid Derivatives: Spirotetramat 1397Peter Jeschke, Reiner Fischer, and Ralf Nauen40.4.5 Tetramic Acid Derivatives: Spiropidion 1408Anke Buchholz and Michel Muehlebach40.4.6 Tetramic Acid Derivatives: Spidoxamat 1421Reiner Fischer, Christian Marienhagen, and Ralf Nauen41 Nervous System 142941.1 Nicotinic Acetylcholine Receptor Competitive Modulators, Allosteric Modulators, and Channel Blockers: Target and Selectivity Aspects 1429Peter Jeschke, Ralf Nauen, and Michael Edmund Beck41.2 Chemical Structural Features of Nicotinic Acetylcholine Receptor Competitive Modulators 1481Peter Jeschke41.2.1 Introduction 148141.2.2 Active Ingredients of the IRAC MoA Subgroup 4A 148241.2.3 Active Ingredients of the IRAC MoA Subgroups 4C to 4E 148541.2.4 Neonicotinoids 148741.2.4.1 Noncyclic Neonicotinoids 1487Peter Jeschke41.2.4.2 Five-Membered Heterocycles: Imidacloprid and Thiacloprid 1517Peter Jeschke and Koichi Moriya41.2.4.3 Six-Membered Heterocycles: Thiamethoxam and AKD 1022 1537Peter Maienfisch41.2.5 Sulfoximines: Sulfoxaflor 1566Thomas 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. WatsonVolume 3bPreface to the Fourth Edition xxvii41.2.6 Butenolides: Flupyradifurone 1599Peter Jeschke, Ralf Nauen, Robert Velten, Michael E. Beck, Matthias Haas, Christian Funke, and Georg Raupach41.2.7 Mesoionics 162641.2.7.1 Triflumezopyrim 1626Daniel Cordova, Wenming Zhang, Caleb W. Holyoke Jr, James D. Barry, Vineet Singh, Isaac B. Annan, Luis A.F. Teixeira, and John L. Andreassi41.2.7.2 Fenmezoditiaz 1642Joachim Dickhaut, Martin Weisel, Huazhang Huang, Lixin Mao, Barbara Wedel, Colin Ehnes, and Kai Ristau41.2.8 Pyridinylidenes: Flupyrimin 1651Ryo Horikoshi, Takehito Terajima, Kenji Shimomura, and Motohiro Tomizawa41.3 Nicotinic Acetylcholine Receptor Allosteric Modulators – Site I: Spinosyns 1659Thomas 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 Mezei41.4 Nicotinic Acetylcholine Receptor Allosteric Modulators – Site II: GS-Omega/Kappa HxTx-Hv1a Peptide 1687Dara G. Stockton41.5 Sodium Channel Modulators 1702Peter Jeschke41.6 Voltage-dependent Sodium Channel Blockers 171841.6.1 Oxadiazines: Indoxacarb 1718Stephen F. McCann, Daniel Cordova, John T. Andaloro, and George P. Lahm41.6.2 Semicarbazone: Metaflumizone 1734David Kuhn, Kazuhiro Takagi, Tomokazu Hino, Nigel Armes, and Desirée Hodges41.7 GABA-gated Chloride Channel Blockers 174441.7.1 Phenylpyrazoles: Ethiprole and Fipronil 1744Vincent L. Salgado, Keith A. Holmes, Lixin Mao, and Stefan Schnatterer41.8 GABA-gated Chloride Channel Allosteric Modulators 178241.8.1 Meta-diamides: Broflanilide 1782Toshifumi Nakao and Shinichi Banba41.8.2 Isoxazolines: Fluxametamide 1791Takeshi Mita, Yuki Furukawa, Motoyoshi Iwasa, Takamasa Kikuchi, Miho Asahi, and Mitsuaki Komoda41.8.3 Isoxazolines: Isocycloseram 1801Jérôme Cassayre and Myriem El Qacemi41.9 Glutamate-gated Chloride Channel Allosteric Modulators: Avermectins and Milbemycins 1815Ottmar Franz Hüter and Thomas Pitterna42 Chordotonal Organ TRPV Channel Modulators 183942.1 Pyridine Azomethine Derivatives: Pymetrozine and Pyrifluquinazon 1839Peter Maienfisch42.2 Pyropenes: Afidopyropen 1856Desirée M. Hodges, Anna K. Hoffarth, Ryo Horikoshi, Christopher Koradin, James Machamer, Christoph Schissler, Toshiaki Sunazuka, Robert R. Svadlenak, and Siddharth Tiwari42.3 Indazapyroxamet 1868Wenming Zhang, Daniel Cordova, Jason Hamm, Billy Annan, David Clark, and Suobao Rong43 Chordotonal Organ Modulators 187943.1 Chordotonal Organ Nicotinamidase Inhibitors: Flonicamid 1879Peter Maienfisch43.2 Chordotonal Organ Modulators – Undefined Target Site: Dimpropyridaz 1890Barbara Wedel, Desirée Hodges, and Karsten Koerber44 New Unknown Mode of Action 189944.1 Pyridalyl 1899Shigeru Saito and Noriyasu Sakamoto44.2 Benzpyrimoxan 1906Eikoh Satoh45 Insecticides Affecting Calcium Homeostasis 191345.1 Ryanodine Receptor Modulators: Diamides 1913Peter Lümmen, Ulrich Ebbinghaus-Kintscher, Takao Masaki, Hiroshi Hamaguchi, and Takashi Hirooka45.2 Phthalic Acid Diamide: Flubendiamide 1923Ulrich Ebbinghaus-Kintscher, Peter Lümmen, Takao Masaki, Hiroshi Hamaguchi, and Takashi Hirooka45.3 Anthranilic Diamides: Chlorantraniliprole and Cyantraniliprole 1929George 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. Selby45.4 Anthranilic Diamide: Cyclaniliprole 1949Masamitsu Tsukamoto, Taku Hamamoto, Satoko Fujii, Chiaki Takeda, Yusuke Kumakura, and Masayuki Morita45.5 Anthranilic Diamide: Tetraniliprole 1960Rüdiger Fischer, Christian Funke, Sergii Pazenok, and Matthieu Willot46 Vesicular Acetylcholine Transporter Inhibitors 197546.1 Oxazosulfyl 1975Mai Ito, Shinya Nishimura, and Yoshihiko Nokura47 Nematicides 197947.1 IRAC: Nematicide Mode of Action Classification 1979Peter Maienfisch47.2 Mitochondrial Complex II Electron Transport Inhibitors – Succinate-coenzyme Q Reductase 201047.2.1 Fluopyram 2010Peter Lümmen, Svenja Bellof, and Helmut Fürsch47.2.2 Cyclobutrifluram 2023Olivier Loiseleur, Anthony Flemming, Torsten Luksch, Brigitte Slaats, Matthias Gaberthueel, Marcus Guest, and Richard Currie47.3 Compounds of Unknown or Uncertain Mode of Action 203747.3.1 Fluazaindolizine 2037George 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. Smith47.3.2 Fluazaindolizine (Addendum) 2047Tim Thoden, John A. Wiles, Chaoxian Geng, and Timothy WilsonIndex 2051