文献类型：期刊文献

英文题名：Design, Synthesis, and Bioactivity of Trifluoroethylthio-Substituted Phenylpyrazole Derivatives

作者：Dong, Lefeng[1];Wang, Weiguo[1];Zhou, Liqi[2];Yang, Wulin[1];Xu, Zhiping[1];Cheng, Jiagao[1];Shao, Xusheng[1];Xu, Xiaoyong[1];Li, Zhong[1,3]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China;[2]Shanghai GreenTech Lab Co Ltd, Shanghai 100093, Peoples R China;[3]Shanghai Collaborat Innovat Ctr Biomfg Technol, Shanghai 200237, Peoples R China

年份：2024

卷号：72

期号：21

起止页码：11949

外文期刊名：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

收录：;EI(收录号：20242116133303);WOS:【SCI-EXPANDED(收录号:WOS:001227295700001)】；

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; trifluoroethylthio group; insecticidalactivity; molecular docking; toxicity on zebrafish

摘要：As the first marketed phenylpyrazole insecticide, fipronil exhibited remarkable broad-spectrum insecticidal activity. However, it poses a significant threat to aquatic organisms and bees due to its high toxicity. Herein, 35 phenylpyrazole derivatives containing a trifluoroethylthio group on the 4 position of the pyrazole ring were designed and synthesized. The predicted physicochemical properties of all of the compounds were within a reasonable range. The biological assay results revealed that compound 7 showed 69.7% lethality against Aedes albopictus (A. albopictus) at the concentration of 0.125 mg/L. Compounds 7, 7g, 8d, and 10j showed superior insecticidal activity for the control of Plutella xylostella (P. xylostella). Notably, compound 7 showed similar insecticidal activity against Aphis craccivora (A. craccivora) compared with fipronil. Potential surface calculation and molecular docking suggested that different lipophilicity and binding models to the Musca domestica (M. domestica) gamma-aminobutyric acid receptors may be responsible for the decreased activity of the tested derivatives. Toxicity tests indicated that compound 8d (LC50 = 14.28 mg/L) induced obviously 14-fold lower toxicity than fipronil (LC50 = 1.05 mg/L) on embryonic-juvenile zebrafish development.