Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4-oxadiazole derivatives

J Agric Food Chem. 2012 Nov 28;60(47):11649-56. doi: 10.1021/jf303807a. Epub 2012 Nov 15.

Abstract

A novel series of 1,3,4-oxadiazole derivatives containing a 5-phenyl-2-furan moiety were synthesized from the intermediates diacylhydrazine 3 and acylhydrazone 5 via an efficient approach under microwave irradiation in good yields. Their structures were characterized by IR, (1)H NMR, and elemental analysis. The antifungal tests indicated that the title compounds showed in vivo fungicidal activity against Botrytis cinerea and Rhizoctonia solanii at 500 μg/mL obviously. Some tested compounds even had a superiority effect over the commercial fungicides 40% Pyrimethanil SC and 3% Validamycin AS. The activity between the title compound and their precursors diacylhydrazine 3 and acylhydrazone 5 was also compared and discussed.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Botrytis / drug effects
  • Fungicides, Industrial / chemical synthesis*
  • Fungicides, Industrial / pharmacology*
  • Hydrazines / chemistry
  • Hydrazones / chemistry
  • Microwaves
  • Molecular Structure
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / chemistry
  • Oxadiazoles / pharmacology*
  • Rhizoctonia / drug effects

Substances

  • Fungicides, Industrial
  • Hydrazines
  • Hydrazones
  • Oxadiazoles
  • hydrazine