Synthesis, DFT, and eco-friendly insecticidal activity of some N-heterocycles derived from 4-((2-oxo-1,2-dihydroquinolin-3-yl)methylene)-2-phenyloxazol-5(4H)-one

Bioorg Chem. 2021 Jul:112:104945. doi: 10.1016/j.bioorg.2021.104945. Epub 2021 Apr 26.

Abstract

A new series of nitrogen heterocycles encompassing a quinoline scaffold such as imidazolone, benzimidazole, triazinone, triazole, and thiazole derivatives was synthesized utilizing the readily obtainable building block synthon, 4-((2-oxo-1,2-dihydroquinolin-3-yl)methylene)-2-phenyloxazol-5(4H)-one (3). It was interesting that the fused heterocycle, pyranoquinoline derivative 15 was successfully synthesized by different routes of reactions. The synthesized compounds were evaluated for their insecticidal activity and compounds 6, 17, and 20 were the most potent against both Mythimna separata and Nilaparvata lugens. The DFT study was performed for the most potent compounds.

Keywords: Benzimidazole; Insecticidal; Oxazolone; Quinolone; Triazinone.

MeSH terms

  • Animals
  • Density Functional Theory*
  • Dose-Response Relationship, Drug
  • Hemiptera / drug effects
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / pharmacology*
  • Insecticides / chemical synthesis
  • Insecticides / chemistry
  • Insecticides / pharmacology*
  • Molecular Structure
  • Moths / drug effects
  • Structure-Activity Relationship

Substances

  • Heterocyclic Compounds
  • Insecticides