Synthesis and antifungal activity of 1,2,3-triazole phenylhydrazone derivatives

Org Biomol Chem. 2015 Jan 14;13(2):477-86. doi: 10.1039/c4ob01758g. Epub 2014 Nov 6.

Abstract

A series of 1,2,3-triazole phenylhydrazone derivatives were designed and synthesized as antifungal agents. Their structures were determined based on (1)H-NMR spectroscopy, MS, elemental analysis and X-ray single-crystal diffraction. The antifungal activities were evaluated against four phytopathogenic fungi including Rhizoctonia solani, Sclerotinia sclerotiorum, Fusarium graminearum and Phytophthora capsici, by the mycelium growth inhibition method in vitro. Compound 5p exhibited significant anti-phytopathogenic activity, with the EC50 values of 0.18, 2.28, 1.01, and 1.85 μg mL(-1), respectively. In vivo testing demonstrated that 5p was effective in the control of rice sheath blight, rape sclerotinia rot and fusarium head blight. A 3D-QSAR model was built for a systematic SAR profile to explore more potent 1,2,3-triazole phenylhydrazone analogs as novel fungicides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Crystallography, X-Ray
  • Fungi / drug effects
  • Hydrazones / chemical synthesis*
  • Hydrazones / chemistry
  • Hydrazones / pharmacology*
  • Mass Spectrometry
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Proton Magnetic Resonance Spectroscopy
  • Quantitative Structure-Activity Relationship
  • Triazoles / chemistry*

Substances

  • Antifungal Agents
  • Hydrazones
  • Triazoles
  • phenylhydrazone