Structure-activity Relationships of Larvicidal Monoterpenes and Derivatives Against Aedes Aegypti Linn

Chemosphere. 2011 Jun;84(1):150-3. doi: 10.1016/j.chemosphere.2011.02.018. Epub 2011 Mar 3.

Abstract

In the search for larvicidal compounds against Aedes aegypti L. (Diptera: Culicidae), a collection of monoterpenes were selected and evaluated. R- and S-limonene exhibited the highest larvicidal potency (LC(50)=27 and 30 ppm, respectively), followed by γ-terpinene (LC(50)=56 ppm) and RS-carvone (LC(50)=118 ppm). Structural characteristics which may contribute to the understanding of the larvicidal activity of monoterpenes were empirically identified. The presence of heteroatoms in the basic hydrocarbon structure decreases larvicidal potency. Conjugated and exo double bonds appear to increase larvicidal potency. Replacement of double bonds by more reactive epoxides decreases the larvicidal potency. The presence of hydroxyls in the cyclic structure resulted in decreased potency, probably due to increased polarity indicanting that lipophilicity seems to play an important role in increasing the larvicidal potency in this set of compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aedes / drug effects*
  • Animals
  • Cyclohexenes / toxicity
  • Insecticides / chemistry
  • Insecticides / toxicity*
  • Larva / drug effects
  • Limonene
  • Monoterpenes / chemistry
  • Monoterpenes / toxicity*
  • Structure-Activity Relationship
  • Terpenes / toxicity

Substances

  • Cyclohexenes
  • Insecticides
  • Monoterpenes
  • Terpenes
  • Limonene