Design, Synthesis, and Insecticidal Activity of Mesoionic Pyrido[1,2- a]pyrimidinone Containing Isoxazole/Isoxazoline Moiety as a Potential Insecticide

J Agric Food Chem. 2023 Jun 7;71(22):8381-8390. doi: 10.1021/acs.jafc.3c01132. Epub 2023 May 23.

Abstract

Bean aphid (Aphis craccivora) resistance to commonly used insecticides has made controlling these pests increasingly difficult. In this study, we introduced isoxazole and isoxazoline, which possess insecticidal activity, into pyrido[1,2-a]pyrimidinone through a scaffold hopping strategy. We designed and synthesized a series of novel mesoionic compounds that exhibited a range of insecticidal activities against A. craccivora. The LC50 values of compounds E1 and E2 were 0.73 and 0.88 μg/mL, respectively, better than triflumezopyrim (LC50 = 2.43 μg/mL). Proteomics and molecular docking analyses showed that E1 might influence the A. craccivora nervous system by interacting with neuronal nicotinic acetylcholine receptors (nAChRs). This research offers a new approach to the advancement of novel mesoionic insecticides.

Keywords: insecticidal activity; isoxazole/isoxazoline; mesoionic pyrimidinone; molecular docking; proteomics.

MeSH terms

  • Animals
  • Aphids
  • Insecticides* / chemical synthesis
  • Insecticides* / chemistry
  • Insecticides* / pharmacology
  • Isoxazoles / chemistry
  • Molecular Structure
  • Proteomics
  • Pyrimidinones* / chemical synthesis
  • Pyrimidinones* / chemistry
  • Pyrimidinones* / pharmacology
  • Structure-Activity Relationship

Substances

  • Pyrimidinones
  • Insecticides
  • Isoxazoles