Synthesis and antifeedant activity of novel alpha-asarone derivatives against stored-product pests

Pest Manag Sci. 2013 Aug;69(8):964-74. doi: 10.1002/ps.3461. Epub 2013 Jan 28.

Abstract

Background: Alpha-asarone (2,4,5-trimethoxypropenylbenzene) derivatives represent a new series of compounds that possess good antifeedant activity against different stored-product pests.

Results: A total of 23 novel alpha-asarone derivatives were synthesised and identified by (1) H NMR, (13) C NMR and IR, and their feeding deterrent activities were tested against Sitophilus granarius L., Trogoderma granarium Ev. and Tribolium confusum Duv. Ten compounds showed strong antifeedant activities.

Conclusion: Some of the title compounds displayed very good and broad-spectrum activities against adult and larval Coleoptera. The results indicate that the presence of a double bond in the side chain and three methoxy groups is important for antifeedant activity.

Keywords: alpha-asarone derivatives; antifeedant activity; stored-product pests; synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allylbenzene Derivatives
  • Animals
  • Anisoles / chemical synthesis
  • Anisoles / chemistry
  • Anisoles / pharmacology*
  • Coleoptera / drug effects*
  • Coleoptera / physiology*
  • Feeding Behavior / drug effects
  • Food Parasitology
  • Insecticides / chemical synthesis
  • Insecticides / chemistry
  • Insecticides / pharmacology*
  • Molecular Structure

Substances

  • Allylbenzene Derivatives
  • Anisoles
  • Insecticides
  • asarone