Synthesis and antifungal activity of carvacrol and thymol esters with heteroaromatic carboxylic acids

Nat Prod Res. 2019 Jul;33(13):1924-1930. doi: 10.1080/14786419.2018.1480618. Epub 2018 Jun 6.

Abstract

Aiming to obtain the more effective pathogen inhibitive ingredients and explore the influence of introducing different heterocyclic units to carvacrol and thymol esters, twenty ester derivatives with different heterocyclic units were synthesized. And the in vitro antifungal activity of title compounds against five plant pathogenic fungi was evaluated by mycelium growth rate method. The results showed that some carvacrol and thymol esters showed good to excellent antifungal activity, and compound 9d (4-bromo-5-isopropyl-2-methylphenyl picolinate) exhibited a broad antifungal spectrum. Preliminary study indicated that the introduction of furan, thiophene and pyridine unit could enhance the antifungal activity of carvacrol and thymol esters against Botrytis cinerea and a bromine atom on the para position of benzene moiety could enhance their antifungal activity.

Keywords: Carvacrol; antifungal activity; ester derivatives; heterocyclic compound; thymol.

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / pharmacology*
  • Botrytis / drug effects
  • Botrytis / pathogenicity
  • Carboxylic Acids / chemistry
  • Cymenes
  • Drug Evaluation, Preclinical / methods
  • Esters / chemistry
  • Fungicides, Industrial / chemical synthesis
  • Fungicides, Industrial / chemistry
  • Fungicides, Industrial / pharmacology
  • Microbial Sensitivity Tests
  • Monoterpenes / chemical synthesis
  • Monoterpenes / chemistry*
  • Monoterpenes / pharmacology
  • Mycelium / drug effects
  • Structure-Activity Relationship
  • Thymol / chemical synthesis
  • Thymol / chemistry*

Substances

  • Antifungal Agents
  • Carboxylic Acids
  • Cymenes
  • Esters
  • Fungicides, Industrial
  • Monoterpenes
  • Thymol
  • carvacrol