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Full Description
The gold-standard reference on the discovery, development, and use of crop protection compounds
In the newly revised fourth edition of Modern Crop Protection Compounds, a team of distinguished researchers provides an exhaustive overview of today's most important crop protection compounds. Divided into four volumes, dedicated to herbicides, fungicides, and insecticides, the authors explain the invention and development of agrochemicals, their chemistry, mode of action, physicochemical properties, structure-activity relationships, biological and safety profile, industrial synthesis, commercial use, and resistance management, bringing together the most important agrochemical information in a single, comprehensive source.
Building on the success of the previous editions, Volume 3 on insecticides covers:
A thorough introduction to the individual modes of action and resistance evolution of insecticides, classified by the Insecticide Resistance Action Committee (IRAC)
Comprehensive discussions of the newest insecticides, up to those released in 2024
Brand-new material, including entirely new chapters, with revised and updated content reflecting the latest research advances
Contributions by some of the leading names in the international agrochemical industry
Perfect for researchers in industry working in the area of agrochemical research and development, mainly in the plant protection industry, Modern Crop Protection Compounds will also benefit organic chemists at universities, as well as professionals on advisory boards, and with societies and governmental authorities.
Contents
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 Lümmen, 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 Desirée 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
Jérôme Cassayre and Myriem El Qacemi
41.9 Glutamate-gated Chloride Channel Allosteric Modulators: Avermectins and Milbemycins 1815
Ottmar Franz Hüter 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
Desirée 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, Desirée 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 Lümmen, Ulrich Ebbinghaus-Kintscher, Takao Masaki, Hiroshi Hamaguchi, and Takashi Hirooka
45.2 Phthalic Acid Diamide: Flubendiamide 1923
Ulrich Ebbinghaus-Kintscher, Peter Lümmen, 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
Rüdiger 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 Lümmen, Svenja Bellof, and Helmut Fürsch
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
