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| Diamide derivatives containing a trifluoromethylpyridine skeleton: Design,
synthesis, and insecticidal activity |
| XU Fang-zhou*, WANG Yan-yan*, GUO Sheng-xin, DAI A-li, WU Jian |
| State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering/Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education/Guizhou University, Guiyang 550025, P.R.China |
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摘要 双酰胺衍生物近年来在农药（特别是杀虫剂）的研究中被广泛关注。本文通过简单、环保的合成路线，设计、合成了一系列含有三氟甲基吡啶骨架的新型双酰胺衍生物，通过1H、19F和13C
NMR以及HR-MS进行了确证。并测定了它们对小菜蛾（Plutella xylostella）和棉铃虫（Helicoverpa
armigera）的杀虫活性，讨论了构效关系。部分化合物（D2、D5、D10、D21、D28、D29、D30和D33）在500
mg·L-1时对小菜蛾具有100%杀虫活性。其中，化合物D33在100
mg·L-1时对具有100%的杀虫活性，其LC50值（致死中浓度）为3.7 mg
L-1，为该类化合物中最低值。分子对接结果表明，D33可嵌入鱼尼丁受体的活性口袋中，与商业杀虫剂氯虫苯甲酰胺类似，通过多个氢键与鱼尼丁受体相互作用。
Abstract
Diamide derivatives are biologically active molecules that have been widely applied in recent years in research on pesticides, especially insecticides. Using a simple and environmentally friendly scheme, a series of new diamide derivatives containing a trifluoromethylpyridine skeleton was designed, synthesized, and confirmed by 1H, 19F and 13C NMR, and HR-MS. Their insecticidal activities against Plutella xylostella and Helicoverpa armigera were measured and the relationship between structure and activity was investigated. Eight of the title compounds (D2, D5, D10, D21, D28, D29, D30 and D33) showed 100% activity against P. xylostella at 500 mg L–1. One compound, D33, still showed 100% activity against P. xylostella at 100 mg L–1 and had the lowest LC50 (lethal concentration 50%, 3.7 mg L–1) among the synthesized compounds. Molecular docking analysis revealed that D33 could be thoroughly embedded in the active pocket of the ryanodine receptor via hydrogen bonding in a manner similar to the commercial insecticide chlorantraniliprole.
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Received: 31 August 2021
Accepted: 20 October 2021
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| Fund: his work was supported by the National Natural Science Foundation of China (21762012, 32072445 and 21562012), the Program of Introducing Talents to Chinese Universities (D20023) and the S&T Planning Project of Guizhou Province, China ([2017]1402 and [2017]5788). |
| About author: Correspondence WU Jian, Tel: +86-851-88292090, E-mail: wujian2691@126.com
* These authors contributed equally to this study. |
Cite this article:
XU Fang-zhou, WANG Yan-yan, GUO Sheng-xin, DAI A-li, WU Jian.
2022.
Diamide derivatives containing a trifluoromethylpyridine skeleton: Design,
synthesis, and insecticidal activity. Journal of Integrative Agriculture, 21(10): 2995-3003.
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