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.

中文翻译：

---

三氟乙硫基取代的苯基吡唑衍生物的设计、合成及生物活性


氟虫腈作为第一个上市的苯基吡唑类杀虫剂，表现出显着的广谱杀虫活性。然而，由于其高毒性，对水生生物和蜜蜂构成重大威胁。本文设计并合成了35种吡唑环4位上含有三氟乙硫基的苯基吡唑衍生物。所有化合物的预测理化性质均在合理范围内。生物学测定结果表明，化合物7在0.125 mg/L浓度下对白纹伊蚊（A. albopictus）的致死率达69.7%。化合物7、7g、8d和10j对于防治小菜蛾(P. xylostella)表现出优异的杀虫活性。值得注意的是，与氟虫腈相比，化合物 7 对蚜虫 (A. craccivora) 显示出相似的杀虫活性。电势表面计算和分子对接表明，不同的亲脂性和与家蝇（M. Domestica）γ-氨基丁酸受体的结合模型可能是测试衍生物活性降低的原因。毒性试验表明，化合物8d（LC ₅₀ = 14.28 mg/L）对胚胎幼年斑马鱼的毒性明显低于氟虫腈（LC ₅₀ = 1.05 mg/L）14倍。发展。