文献类型：期刊文献

英文题名：Discovery of Novel Diamides Scaffold Containing Monofluoro-acrylamides Activating the Insect Ryanodine Receptor

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

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

年份：2023

卷号：71

期号：39

起止页码：14137

外文期刊名：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

收录：;EI(收录号：20234314971004);WOS:【SCI-EXPANDED(收录号:WOS:001070268500001)】；

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

语种：英文

外文关键词：diamide insecticide; ryanodine receptor; acrylamide; monofluoroalkene; 3D-QSAR; calcium imaging; molecular docking

摘要：The research and development of organofluorine chemistry has flourished; in particular, monofluoroalkene has aroused considerable interest from medicinal and organic chemists. It is a significant attempt to introduce monofluoroalkene into agrochemicals. In this study, monofluoroalkene was introduced into diamide molecules and inserted between the aliphatic amide and benzene ring, and 44 compounds have been successfully synthesized. The bioassay results showed that compounds with monofluoroacrylamide moiety (Z-isomers) had excellent larvicidal activity against lepidopteran pests at 5 mg center dot L-1. The LC50 values of compounds B16, B18, and B21 against Mythimna separata were 1.02, 1.32, and 0.78 mg center dot L-1, respectively. 3D-QSAR analysis including the CoMFA model and the CoMSIA model was conducted to illustrate the contributions of steric, electrostatic, hydrophobic, and hydrogen bond fields on the bioactivity. Moreover, typical symptoms caused by chlorantraniliprole including dehydration, shrinkage, and blackening were also observed on the test larvae treated with monofluoro-acrylamide diamide compounds. M. separata central neurons calcium imaging experiment of compound B18 indicated that the monofluoro-acrylamide diamide compounds were potential insect ryanodine receptor activators. The molecular docking was performed in the CHL binding domain of Plutella xylostella RyR and revealed that the predicted binding mode of compound B21 was slightly different from that of CHL. The MM|GBSA dG Bind values of B21 and CHL with P. xylostella RyR were respectively -85.797 and -95.641 kcal center dot mol(-1). The present work explored the insecticidal properties of a new diamide scaffold containing a monofluoro-acrylamide fragment and extended the application of monofluoroalkene in the agrochemical field.