Institute of Functional Molecules, Shenyang University of Chemical Technology, Liaoning Province Key Laboratory of Green Functional Molecular Design and Development, Shenyang Key Laboratory of Targeted Pesticides, Shenyang 110142, China.
School of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, Liaoning, China.
J Agric Food Chem. 2024 Jul 10;72(27):15276-15283. doi: 10.1021/acs.jafc.4c02841. Epub 2024 Jun 29.
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 - with a 1-cyanocyclopropimide group exhibited outstanding insecticidal activity. The LC values for compounds - against ranged from 0.58 to 0.91 mg/L. Compound showed an LC value of 0.29 and 3.10 mg/L against and , respectively. Molecular docking indicated the potential binding interactions of compound 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.
以nicofluprole 为先导化合物，我们通过将酰胺氮原子上的甲基用酰基取代，设计并合成了一系列新的苯基吡唑类化合物。生物测定结果表明，具有 1-氰基环丙基亚胺基团的化合物表现出优异的杀虫活性。化合物 - 的 LC 值范围为 0.58 至 0.91 mg/L。化合物 - 对 和 分别表现出 LC 值为 0.29 和 3.10 mg/L。分子对接表明，化合物 - 与γ-氨基丁酸受体具有潜在的结合相互作用。此外，密度泛函理论计算表明，1-氰基环丙基亚胺结构可能是其生物活性所必需的。含有 1-氰基环丙基亚胺片段的苯基吡唑衍生物具有进一步开发为潜在杀虫剂的潜力。
