title: 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.
abstract: 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-formylbenzyl)-1-methyl-1H-pyrazole-5-carboxamide. The structures of target compounds were confirmed by ¹H NMR and high-resolution mass spectrum (HRMS). The results of bioassays indicated that the target compounds possessed good-to-excellent activities against a broad spectrum of insects such as cotton bollworm (Helicoverpa armigera), spider mite (Tetranychus cinnabarinus), bean aphid (Aphis craccivora), and mosquito (Culex pipiens pallens), but gave different structure-activity relationships for each species. Compounds containing imine showed high insecticidal activity against cotton bollworm. Especially, stomach activity of compounds 5-1c was 60% at 11 mg kg⁻¹. The compounds also had good activities against bean aphid and mosquito. The foliar contact activity of compounds 5-1a, 5-1b, 5-1e, 5-3c, and 5-3d against bean aphid were 90, 100, 90, 90, and 90%, respectively, at 200 mg kg⁻¹. The activity of compound containing dihydroisoxazoline moiety (5-4) against mosquito was 60% at 1 mg kg⁻¹, which was near that of tebufenpyrad. The introduction of dihydroisoxazoline structure (5-4) was advantageous to improve the activity of the compound against adult mites compared with other structures; the miticidal activity of 5-4- against adult mites was 60% at 50 mg kg⁻¹.
authors: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, People's Republic of China.
authors: Hongjian
authors: H
authors: Song
authors: Yuxiu
authors: Y
authors: Liu
authors: Lixia
authors: L
authors: Xiong
authors: Yongqiang
authors: Y
authors: Li
authors: Na
authors: N
authors: Yang
authors: Qingmin
authors: Q
authors: Wang
mesh_terms: D000818:Animals; D001665:Binding Sites; D015195:Drug Design; D042967:Electron Transport Complex I / Q000037:antagonists & inhibitors* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D019476:Insect Proteins / Q000037:antagonists & inhibitors* / Q000737:chemistry; D007313:Insecta / Q000187:drug effects; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D004952:Esters; D004987:Ethers; D007097:Imines; D019476:Insect Proteins; D007306:Insecticides; D010091:Oximes; D011720:Pyrazoles; D042967:Electron Transport Complex I