新型四氢噻吩取代类双酰胺化合物的设计、合成及生物活性研究

doi:10.6023/cjoc202603012

摘要/Abstract

为发现结构新颖、活性优异、环境友好的新型杀虫剂, 本研究采用活性亚结构拼接策略, 以环丙氟虫胺为先导化合物, 设计并合成了两个系列共20个未见文献报道的新型双酰胺化合物, 其结构经过¹H NMR、¹³C NMR和HRMS确证. 初步的生物活性测试结果表明, 目标化合物对鳞翅目害虫小菜蛾和粘虫未表现出显著的杀虫活性, 但在半翅目害虫防治方面取得了一定进展. 部分化合物对苜蓿蚜和褐飞虱表现出良好的杀虫活性, 特别是N-(3-((2-溴-6-(二氟甲氧基)-4-(全氟丙烷)苯基)氨甲酰基)-2-氟苯基)-N-(1,1-二氧化四氢噻吩-3-基)-6-(三氟甲基)烟酰胺(8e)表现尤为突出, 在10 mg/L测试浓度下对苜蓿蚜的杀虫活性为100.0%, 在40 mg/L下对褐飞虱的杀虫活性为97.6%, 显著优于对照药剂环丙氟虫胺. 本研究为开发新型双酰胺杀虫剂提供了候选先导分子, 也为防治半翅目害虫提供了新的解决方案.

关键词: 四氢噻吩, 双酰胺, 杀虫活性, 先导化合物, 半翅目害虫

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 ¹H NMR, ¹³C 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.

Key words: tetrahydrothiophene, diamide, insecticidal activity, lead compound, hemipteran pests

引用此文

夏姣云, 刘畅, 胡乐天, 相君成, 吕亮, 庞怀林, 刘吉永. 新型四氢噻吩取代类双酰胺化合物的设计、合成及生物活性研究[J]. 有机化学, 2026, 46(10): 4056-4066.

Jiaoyun Xia, Chang Liu, Letian Hu, Juncheng Xiang, Liang Lü, Huailin Pang, Jiyong Liu. Design, Synthesis, and Biological Activity Study of Novel Tetrahydrothiophene-Substituted Diamides[J]. Chinese Journal of Organic Chemistry, 2026, 46(10): 4056-4066.

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