文献类型：期刊文献

英文题名：Novel Synthetic Method and Insecticidal Evaluation of CF3-Containing Polycyclic Neonicotinoid Derivatives

作者：Zeng, Xiaoqin[1];Zhou, Cong[1];Xu, Qian[1];Shao, Xusheng[1];Xu, Xiaoyong[1];Cheng, Jiagao[1];Yang, Wu-Lin[1];Li, Zhong[1]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

年份：2025

卷号：73

期号：9

起止页码：5033

外文期刊名：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

收录：;EI(收录号：20250917937840);WOS:【SCI-EXPANDED(收录号:WOS:001428477300001)，CCR-EXPANDED(收录号:WOS:001428477300001)】；

基金：This work was supported by the Shanghai Agricultural Science and Technology Innovation Project (K2023020), National Natural Science Foundation of China (22171081 and 22477027), Shanghai Rising-Star Program (23QA1402600), Natural Science Foundation of Shanghai Municipality (23ZR1416700), and Shanghai Agriculture Applied Technology Development Program (T2023309). The authors thank the Research Center of Analysis and Test of East China University of Science and Technology for the help with HRMS and NMR analyses.

语种：英文

外文关键词：neonicotinoid insecticides; insecticidal activity; trifluoromethyl group; annulation reaction; molecular docking

摘要：The modification of active ingredients with a trifluoromethyl group represents a significant approach for the discovery of highly active pesticides. Herein, we developed a novel [3 + 3] annulation reaction of neonicotinoid precursors and trifluoromethyl-alpha,beta-ynones and synthesized a series of CF3-containing polycyclic neonicotinoid derivatives in high efficiency. The insecticidal activity results indicated that most of the target compounds showed good insecticidal activities against Aphis craccivora and Nilaparvata lugens at a concentration of 100 mg/L. In particular, compounds 3o and 4k had LC50 values of 1.53 and 1.47 mg/L against A. craccivora, respectively, which were comparable to that of imidacloprid (LC50 = 1.30 mg/L). The honeybee toxicity predictive model also indicated the potential low honeybee toxicity of target compounds 3o and 4k. The molecular docking study revealed that the target compounds 3o and 4k exhibited a favorable binding mode with the Lymnaea stagnalis acetylcholine-binding protein and the R55T-mutated resistant model.