Synthesis and antifungal activity of N-(substituted pyridinyl)-1-methyl(phenyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives

Molecules. 2012 Nov 30;17(12):14205-18. doi: 10.3390/molecules171214205.

Abstract

A series of N-(substituted pyridinyl)-1-methyl(phenyl)-3-trifluoromethyl-1H-pyrazole-4-carboxamide derivatives were synthesized. All target compounds were characterized by spectral data (¹H-NMR, ¹³C-NMR, IR, MS) and elemental analysis and were bioassayed in vitro against three kinds of phytopathogenic fungi (Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica). The results showed that some of the synthesized N-(substituted pyridinyl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamides exhibited moderate antifungal activities, among which compounds 6a, 6b and 6c displayed more than 50% inhibition activities against G. zeae at 100 µg/mL, which was better than that of the commercial fungicides carboxin and boscalid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoimidazole Carboxamide* / analogs & derivatives
  • Aminoimidazole Carboxamide* / chemical synthesis
  • Aminoimidazole Carboxamide* / chemistry
  • Aminoimidazole Carboxamide* / pharmacology
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Fungi / drug effects*
  • Fungi / pathogenicity
  • Fungicides, Industrial* / chemical synthesis
  • Fungicides, Industrial* / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Pyrazoles* / chemical synthesis
  • Pyrazoles* / chemistry
  • Pyrazoles* / pharmacology
  • Structure-Activity Relationship

Substances

  • Antifungal Agents
  • Fungicides, Industrial
  • Pyrazoles
  • Aminoimidazole Carboxamide