稠环缩氨基脲衍生物的合成与杀虫活性研究

Synthesis and insecticidal activity of condensed-cyclic semicarbazone derivatives

摘要:

以4-氯苯乙酸为原料，经环化、氧化、缩合、加氢、酰化等反应合成了一系列新的具有茚结构的稠环缩氨基脲衍生物，总收率7%-9%。其结构经核磁共振氢谱和高分辨质谱确认正确。初步生物活性测试表明：大多数化合物对多种害虫具有很好的杀虫活性。7-氯-2,3,4a,5-四氢-2-[N-甲氧羰基-N-(4-三氟甲基苯基)氨基甲酰基]茚戊[1,2-e][1,3,4]噁二嗪-4a-甲酸甲酯（12b）的活性略高于已商品化杀虫剂茚虫威。

Abstract:

Several new aromatic condensed-cyclic semicarbazone derivatives with the structure of indene were prepared from 4-chlorophenylacetic acid in 7%-9% yield, through cyclization, oxidation, condensation, hydrogenation, acylation etc.. Their structures were confirmed through 1H NMR and HRMS. Preliminary bioassay showed that most of them exhibited good activities toward various insects. Methyl 7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-(trifluoromethyl)- phenyl]amino]carbonyl] indeno[1,2-][1,3,4]oxadiazine-4a(3H)-carboxylate (12b) even shows higher activity than Indoxacarb.