Synthesis and Biological Activity of Benzamides Substituted with Pyridine-Linked 1,2,4-Oxadiazole

Molecules. 2020 Jul 31;25(15):3500. doi: 10.3390/molecules25153500.

Abstract

To find pesticidal lead compounds with high activity, a series of novel benzamides substituted with pyridine-linked 1,2,4-oxadiazole were designed by bioisosterism, and synthesized easily via esterification, cyanation, cyclization and aminolysis reactions. The structures of the target compounds were confirmed by 1H-NMR, 13C-NMR and HRMS. The preliminary bioassay showed that most compounds had good larvicidal activities against mosquito larvae at 10 mg/L, especially compound 7a, with a larvicidal activity as high as 100%, and even at 1 mg/L was still 40%; at 50 mg/L, all the target compounds showed good fungicidal activities against the eight tested fungi. Moreover, compound 7h exhibited better inhibitory activity (90.5%) than fluxapyroxad (63.6%) against Botrytis cinereal. Therefore, this type of compound can be further studied.

Keywords: 1,2,4-oxadiazole; amide compound; fungicidal activity; insecticidal activity; synthesis.

MeSH terms

  • Animals
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Benzamides / chemistry*
  • Botrytis / drug effects
  • Drug Design
  • Insecticides / chemical synthesis*
  • Insecticides / chemistry
  • Insecticides / pharmacology
  • Larva / drug effects
  • Moths / drug effects
  • Moths / growth & development
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / chemistry*
  • Oxadiazoles / pharmacology
  • Pyridines / chemistry*
  • Structure-Activity Relationship

Substances

  • Antifungal Agents
  • Benzamides
  • Insecticides
  • Oxadiazoles
  • Pyridines
  • pyridine

Supplementary concepts

  • Botrytis cinerea