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

研究论文

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

夏姣云^*,a, 刘畅^a, 胡乐天^b, 相君成^b, 吕亮^b, 庞怀林^b, 刘吉永^*,b

^a长沙理工大学化学与医药工程学院长沙 410081
^b南通泰禾化工股份有限公司南通 226407

收稿日期:2026-04-15 修回日期:2026-06-09
基金资助:
生态友好无公害创制产品环丙氟虫胺研发及产业化(No.XA2024017)资助项目.

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

Xia Jiaoyun^*,a, Liu Chang^a, Hu Letian^b, Xiang Juncheng^b, Lv Liang^b, Pang huailin^b, Liu Jiyong^*,b

^aSchool of Chemistry and Pharmaceutical Engineering, Changsha University ofScience and Technology, Changsha 410114, China
^bCAC Nantong Chemical Co., Ltd., Nantong 226407, China

Received:2026-04-15 Revised:2026-06-09
Contact: *E-mail: xiajy625@163.com; jiyong_liu@cacch.com
Supported by:
Research, Development, and Industrialization of the Eco-Friendly and Non-Polluting Innovative ProductCyproflanilide (No.XA2024017).

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摘要/Abstract

为发现结构新颖、活性优异、环境友好的新型杀虫剂,本文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计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, 目标化合物虽未显著提升对鳞翅目害虫小菜蛾和粘虫的杀虫活性,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,特别是化合物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, 先导分子, 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 significantly improve activity against lepidopteran pests including Plutella xylostella and Mythimna separata, progress was made against hemipteran pests. Some compounds exhibited good activity against Aphis craccivora and Nilaparvata lugens. Notably, compound 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, insecticide, 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, doi: 10.6023/cjoc202603012.

Xia Jiaoyun, Liu Chang, Hu Letian, Xiang Juncheng, Lv Liang, Pang huailin, Liu Jiyong. Design, Synthesis, and Biological Activity Study of Novel Tetrahydrothiophene-Substituted Diamidesle[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202603012.

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