文献类型：期刊文献

英文题名：Design, Synthesis, and Biological Activities of Novel Phenylpyrazole Derivatives Containing a Trifluoromethylselenyl Moiety

作者：Dong, Lefeng[1];Chang, Wenning[1];Yang, Wulin[1];Xu, Zhiping[1];Cheng, Jiagao[1];Shao, Xusheng[1];Xu, Xiaoyong[1];Li, Zhong[1,2]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China;[2]Shanghai Collaborat Innovat Ctr Biomfg Technol, Shanghai 200237, Peoples R China

年份：2023

卷号：71

期号：30

起止页码：11396

外文期刊名：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

收录：;EI(收录号：20233214485115);WOS:【SCI-EXPANDED(收录号:WOS:001030158100001)】；

基金：This research was supported by the National Key Research and Development Program of China (2017YFD0200500) and the Innovation Program of Shanghai Municipal Education Commission (2017-01-07-00-02-E00037).

语种：英文

外文关键词：phenylpyrazole; trifluoromethylselenyl; insecticidalactivity; molecular docking; toxicity on zebrafishembryos

摘要：Phenylpyrazole insecticides are widely used for cropprotectionand public sanitation by blocking gamma-aminobutyric acid (GABA)-gatedchloride channels and glutamate-gated chloride (GluCl) channels. Herein,36 novel phenylpyrazole derivatives containing a trifluoromethylselenylmoiety were designed and synthesized based on the strategy of introducinga selenium element. All derivative structures were characterized bynuclear magnetic resonance (NMR) and high-resolution mass spectrometry(HRMS). The insecticidal activity results indicated that some derivativeshad good insecticidal activities against Aedes albopictus (A. albopictus) and Plutella xylostella (P. xylostella). The larvicidal activity against mosquitos of compounds 5, 5a, 5k, and 5l at 0.5 mg/Lwas 60-80%. At a concentration of 500 mg/L, compounds 5, 5a, 5h, 5k, 5l, 5r, 6, 6j, 6k, and 7 showed a 70-100% mortality against P. xylostella. Among them, derivatives 5 and 6 had a better insecticidal effect with mortalityrates of 87 and 93% at 50 mg/L, respectively. It was summarized thatthe different binding poses of fipronil and compounds 5 and 6 in the Musca domestica (M. domestica) GABARs might leadto the disparity in bioactivity from docking studies. Toxicity testson zebrafish suggested that compound 6 may be slightlyless toxic to the embryos than fipronil on hatching rate.