Novel Fluorinated Aniline Anthranilic Diamides Improved Insecticidal Activity Targeting the Ryanodine Receptor

作者：Jinzhou Ren, Haolin Yuan, Xiaoyu Liu, Zhenwu Yu, Fanfei Meng, Lixia Xiong, Na Yang, Yuxin Li, Zhengming Li, Zhijin Fan · 发表于：Journal of Agricultural and Food Chemistry · 年份：2022 · DOI：10.1021/acs.jafc.2c03134 · 被引用次数：30 · 研究领域：Insect-Plant Interactions and Control、Insect Resistance and Genetics、Insect and Pesticide Research

The diamide insecticides show exceptional activity against Lepidoptera insects via activation of ryanodine receptors (RyRs). In the present study, a series of anthranilic diamides containing a fluoroaniline moiety were designed, synthesized, and evaluated for insecticidal potency. Most titled compounds exerted moderate to remarkably high activity against Mythimna separata, Plutella xylostella, and Spodoptera frugiperda . The insecticidal activity of compound II l and II ac against M. separata was 26.7 and 26.7% at 0.1 mg L –1, respectively, equivalent to that of chlorantraniliprole (0.1 mg L –1, 30.0%). Compounds II l, II y, and II z exhibited 8.0-, 1.8-, and 4.7-fold higher potency than chlorantraniliprole against P. xylostella, respectively, as compared with their LC 50 s. Compounds II k and II aa showed good insecticidal activity against S. frugiperda with LC 50 of 0.56 and 0.46 mg L –1, respectively, comparable to that of the commercial insecticide chlorantraniliprole with LC 50 of 0.31 mg L –1 . Calcium imaging experiments indicated RyRs as the action target. Molecular docking suggested a higher binding energy of 8.647 kcal/mol between II l and the M. separata RyR than the 7.820 kcal/mol between chlorantraniliprole and the M. separata RyR. Meanwhile, the docking results of II l with mutated P. xylostella RyR at site G4946E showed that II l could have a good inhibition effect on the resistant P. xylostella . The density functional theory calculations suggested the importa...