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

  • J Agric Food Chem. 2024 Jul 10;72(27):15276-15283. doi: 10.1021/acs.jafc.4c02841.
Dongdong Liu  1  2 ,  Jialin Ye  1 ,  Yixing Gao  1 ,  Hongyan Pei  1 ,  Chunfeng Luo  3 ,  Huan Tian  1 ,  Juan He  1 ,  Jing Zhang  1  2  3 ,  Lixin Zhang  1  2  3
Affiliations
  • 1. 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.
  • 2. School of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, Liaoning, China.
  • 3. Metisa Biotechnology Co., Ltd., Nanning 530000, China.
PMID: 38943575 DOI: 10.1021/acs.jafc.4c02841
Abstract

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.

Keywords
DFT; imide; insecticidal activity; molecular docking; phenylpyrazole; synthesis.
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