Design, Synthesis, and Biological Activity Study of Novel Tetrahydrothiophene-Substituted Diamides

To discover novel, highly active, and eco-friendly insecticides, 20 unreported diamide compounds were designed via active substructure splicing strategy using cyproflanilide as the lead.Their structures were confirmed by 1 H NMR, 13 C NMR, and HRMS.Preliminary bioassays showed that although the target compounds did not exhibit significant activity against lepidopteran pests including Plutella xylostella and Mythimna separata, they showed promising activity against hemipteran pests.Some compounds exhibited good activity against Aphis craccivora and Nilaparvata lugens.Notably, N-(3-((2-bromo-6-(difluoromethoxy)-4-(perfluoropropan-2-yl)phenyl)carbamoyl)-2-fluorophenyl)-N-(1,1-dioxidotetrahydrothiophen-3-yl)-6-(trifluoromethyl)nicotinamide (8e) showed outstanding efficacy, with 100.0%insecticidal activity against Aphis craccivora at 10 mg/L and 97.6% against Nilaparvata lugens at 40 mg/L, significantly outperforming the control cyproflanilide.This study provides lead candidates for developing novel diamide insecticides and offers new solutions for managing hemipteran pests.Keywords tetrahydrothiophene; diamide; insecticidal activity; lead compound; hemipteran pests 以氯虫苯甲酰胺(Chlorantraniliprole, 1) [1] 、溴氰虫酰 胺(Cyantraniliprole, 2) [2] (图 1)等为代表的第 28 组双酰胺 类杀虫剂属于鱼尼丁受体调节剂, 主要作用于昆虫鱼尼 丁受体, 导致钙离子异常释放, 从而引起昆虫死亡.因 其具有对鳞翅目害虫高活性、无交互抗性、选择性强等 特点, 已成为全球农作物害虫防治的核心药剂 [3][4][5][6] .