Synthesis and insecticidal activity of benzoheterocyclic analogues of N'-benzoyl-N-(tert-butyl)benzohydrazide: Part 1. Design of benzoheterocyclic analogues

Pest Manag Sci. 2003 Jan;59(1):25-35. doi: 10.1002/ps.604.

Abstract

The N'-benzoyl group of N-tert-butyl-N'-benzoyl-3,5-dimethylbenzohydrazide (1) was converted to a series of benzoheterocyclecarbonyl groups in order to investigate the potential usefulness of superimposing a hydrazine insecticide on 20-hydroxyecdysone. A series of analogues with benzodioxole, benzodioxane, benzodioxapine, indole, benzoxazole, benzoxazine or benzothiazole instead of the phenyl group of (1) were synthesized and tested for their insecticidal activity against the common cutworm (Spodoptera litura F). N-tert-Butyl-N'-(3,5-dimethylbenzoyl)-1,3-benzodioxole-5-carbohydrazide and N-tert-butyl-N'-(3,5-dimethylbenzoyl)-2,3-dihydro-1,4-benzodioxine-6-carbohydrazide showed high insecticidal activities, superior to that of (1) and equal to that of the commercial insecticide tebufenozide (RH-5992).

MeSH terms

  • Animals
  • Drug Design*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / pharmacology*
  • Heterocyclic Compounds / toxicity
  • Hydrazines / chemistry*
  • Hydrazines / pharmacology
  • Hydrazines / toxicity
  • Insecticides / chemical synthesis*
  • Insecticides / chemistry
  • Insecticides / pharmacology*
  • Insecticides / toxicity
  • Larva / drug effects
  • Molecular Structure
  • Spodoptera / drug effects

Substances

  • Heterocyclic Compounds
  • Hydrazines
  • Insecticides
  • 1,2-dibenzoyl-tert-butylhydrazine
  • tebufenozide