Design, synthesis and structure-activity relationship of novel coumarin derivatives

Pest Manag Sci. 2011 Jun;67(6):647-55. doi: 10.1002/ps.2103. Epub 2011 Feb 9.

Abstract

Background: The lead coumarin derivative (E)-methyl 3-methoxy-2-[2-(4-methylcoumarin-7-yloxymethyl)phenyl]acrylate was discovered by using an intermediate derivatisation method. To discover new coumarin derivatives with improved activity, a series of substituted coumarins were synthesised and bioassayed.

Results: The compounds were identified by ¹H NMR, IR, MS and elemental analysis. Bioassays demonstrated that some of the title compounds exhibited excellent fungicidal activity against cucumber downy mildew at 25 mg L⁻¹. The relationship between structure and fungicidal activity is reported.

Conclusion: The present work demonstrates that coumarin derivatives containing methoxyacrylate moieties can be used as possible lead compounds for developing novel fungicides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemical synthesis
  • Acrylates / chemistry
  • Acrylates / pharmacology
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology*
  • Ascomycota / drug effects*
  • Biological Assay
  • Coumarins / chemical synthesis
  • Coumarins / chemistry*
  • Coumarins / pharmacology*
  • Microbial Sensitivity Tests
  • Oomycetes / drug effects*
  • Structure-Activity Relationship

Substances

  • Acrylates
  • Antifungal Agents
  • Coumarins
  • methyl 2-(2-(3-n-butyl-4-methylcoumarin-7-yloxymethyl)phenyl)-3-methoxyacrylate