Design, Synthesis, and Insecticidal Evaluation of New Pyrazole Derivatives Containing Imine, Oxime Ether, Oxime Ester, and Dihydroisoxazoline Groups Based on the Inhibitor Binding Pocket of Respiratory Complex I

• Published in: Journal of agricultural and food chemistry Vol. 61; no. 37; pp. 8730 - 8736
• Main Authors: Song, Hongjian, Liu, Yuxiu, Xiong, Lixia, Li, Yongqiang, Yang, Na, Wang, Qingmin
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 18.09.2013; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Animals; antagonists & inhibitors; Aphis craccivora; Aphis fabae; Binding Sites; bioassays; Biological and medical sciences; chemical synthesis; Chemistry; Chemistry, Applied; Culex pipiens pallens; Drug Design; drug effects; Electron Transport Complex I; Electron Transport Complex I - antagonists & inhibitors; Electron Transport Complex I - chemistry; Esters; Esters - chemical synthesis; Esters - chemistry; Esters - pharmacology; Ethers; Ethers - chemical synthesis; Ethers - chemistry; Ethers - pharmacology; Food industries; Food Science & Technology; Fundamental and applied biological sciences. Psychology; Helicoverpa armigera; Imines; Imines - chemical synthesis; Imines - chemistry; Imines - pharmacology; Insect Proteins; Insect Proteins - antagonists & inhibitors; Insect Proteins - chemistry; Insecta; Insecta - drug effects; insecticidal properties; Insecticides; Insecticides - chemical synthesis; Insecticides - chemistry; Insecticides - pharmacology; Life Sciences & Biomedicine; mites; Molecular Structure; nuclear magnetic resonance spectroscopy; Oximes; Oximes - chemical synthesis; Oximes - chemistry; Oximes - pharmacology; pharmacology; Physical Sciences; protein binding; Pyrazoles; Pyrazoles - chemical synthesis; Pyrazoles - chemistry; Pyrazoles - pharmacology; Science & Technology; stomach; Structure-Activity Relationship; Tetranychus cinnabarinus; oxime ether; imine; oxime ester; pyrazole-5-carboxamide; complex I; dihydroisoxazoline; insecticidal activity; BENZOYLPHENYLUREAS; SAR; pyrazole-S-carboxamide; Binding; Evaluation; Insecticide; Ether; Pesticides; Oxime; Complexes; Design; Ester; Synthesis; Carboxamide; Inhibitor; Respiration

On the basis of complex I receptor protein binding site and commercial tebufenpyrad and tolfenpyrad, four series of novel pyrazole-5-carboxamides containing imine, oxime ether, oxime ester, and dihydroisoxazoline were designed and synthesized via the key intermediate 4-chloro-3-ethyl-N-(4-formylbenz...