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

• Published in: Journal of agricultural and food chemistry Vol. 72; no. 27; pp. 15276 - 15283
• Main Authors: Liu, Dongdong, Ye, Jialin, Gao, Yixing, Pei, Hongyan, Luo, Chunfeng, Tian, Huan, He, Juan, Zhang, Jing, Zhang, Lixin
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 10.07.2024
• Subjects: Bioactive Constituents, Metabolites, and Functions; synthesis; molecular docking; DFT; phenylpyrazole; imide; insecticidal activity
• ISSN: 0021-8561; 1520-5118; 1520-5118
• DOI: 10.1021/acs.jafc.4c02841

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.