Using nicofluprole as the lead compound, we designed and synthesized a series of new phenylpyrazole analogues through substituting the methyl group on the nitrogen atom of the amide with an acyl group. Bioassay results showed that compounds A12–A17 with a 1-cyanocyclopropimide group exhibited outstanding insecticidal activity. The LC₅₀ values for compounds A12–A17 against Tetranychus cinnabarinus ranged from 0.58 to 0.91 mg/L. Compound A15 showed an LC₅₀ value of 0.29 and 3.10 mg/L against Plutella xylostella and Myzus persicae, respectively. Molecular docking indicated the potential binding interactions of compound A15 with a gamma-aminobutyric acid receptor. Additionally, density functional theory calculations implied that the 1-cyanocyclopropimide structure might be essential for its biological activity. Phenylpyrazole derivatives, containing a 1-cyanocyclopropimide fragment, have the potential for further development as potential insecticides.

中文翻译：

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包含酰亚胺部分的新型苯基吡唑衍生物的设计、合成和杀螨/杀虫活性


以烟氟虫酰胺为先导化合物，通过酰基取代酰胺氮原子上的甲基，设计合成了一系列新型苯基吡唑类似物。生物测定结果表明，具有1-氰基环丙酰亚胺基团的化合物A12 - A17表现出优异的杀虫活性。化合物A12 – A17对朱砂叶螨的 LC ₅₀值范围为 0.58 至 0.91 mg/L。化合物A15对小菜蛾和桃蚜的LC ₅₀值分别为0.29和3.10mg/L。分子对接表明化合物A15与 γ-氨基丁酸受体存在潜在的结合相互作用。此外，密度泛函理论计算表明1-氰基环丙酰亚胺结构可能对其生物活性至关重要。含有1-氰基环丙酰亚胺片段的苯基吡唑衍生物具有作为潜在杀虫剂进一步开发的潜力。