文献类型：期刊文献

英文题名：Anthranilic Diamides Containing Monofluoroalkene Amide Linkers as Potential Insect RyR Activators: Design, Synthesis, Bio-evaluation, and Computational Study

作者：Yang, Guantian[1];Zhou, Cong[1];Wang, Yutong[1];Li, Yuxin[2];Gu, Yucheng[3];Li, Zhong[1];Cheng, Jiagao[1];Xu, Xiaoyong[1]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China;[2]Nankai Univ, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China;[3]Syngenta, Jealotts Hill Int Res Ctr, Warfield RG42 6EY, England

年份：2023

卷号：71

期号：6

起止页码：2827

外文期刊名：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

收录：;EI(收录号：20230613561261);WOS:【SCI-EXPANDED(收录号:WOS:000937123700001)】；

基金：This work was financially supported by Innovation Program of Shanghai Municipal Education Commission (201701070002E00037) , National Key Research Program of China (2017YFD0200505) , and Syngenta Ph.D. fellowship to Guantian Yang. The authors thank Juncheng Xiang of Shanghai GreenTech Laboratory Co., Ltd and Li Cui of Institute of Plant Protection, Chinese Academy of Agricultural Sciences, for their help in insecticidal bioassays.

语种：英文

外文关键词：anthranilic diamides; ryanodine receptor; insecticidal activity; acrylamide; monofluoroalkene

摘要：In order to develop anthranilic diamides with novel chemotypes, a series of anthranilic diamides with acrylamide linkers were designed and synthesized. The results of preliminary bioassays indicated that compounds with a monofluoroalkene amide linker (Z-isomer) exhibited good larvicidal activity against lepidopteran pests. The LC50 values of compound A23 against Mythimna separata and Plutella xylostella were 1.44 and 3.48 mg-L-1, respectively, while those of chlorantraniliprole were 0.08 and 0.06 mg-L-1, respectively. Compound A23 also exhibited the same level of lethal potency against resistant and susceptible strains of Spodoptera frugiperda at 50 mg-L-1. Compound A23 exhibited similar symptoms as chlorantraniliprole in test larvae. Comparative molecular field analysis was conducted to demonstrate the structure-activity relationship. Central neuron calcium imaging experiments indicated that monofluoroalkene compounds were potential ryanodine receptor (RyR) activators and activated calcium channels in both the endoplasmic reticulum and the cell membrane. Molecular docking suggested that A23 had a better binding potency to P. xylostella RyR than chlorantraniliprole. The MM|GBSA dG bind value of A23 with P. xylostella RyR was 117.611 kcalmol(-1). Monofluoroalkene was introduced into anthranilic diamide insecticides for the first time and brought a novel chemotype for insect RyR activators. The feasibility of fluoroalkenes as insecticide fragments was explored.