Design, Synthesis, and Acaricidal/Insecticidal Activities of New Phenylpyrazole Derivatives Comprising an Imide Moiety.

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.