β-Thujone and Its Derivatives Modify the Probing Behavior of the Peach Potato Aphid

Molecules. 2019 May 14;24(10):1847. doi: 10.3390/molecules24101847.

Abstract

Thujone is a natural biologically active monoterpene ketone component of essential oils of numerous plants. The aim of the study was to evaluate the effect of β-thujone and β-thujone derivatives bisulfite adduct, lactone, oxime, and lactam application on behavior of Myzus persicae (Sulz.) (Hemiptera: Aphididae) during probing and settling. The choice and no-choice tests (aphid settling and Electrical Penetration Graph (EPG), respectively) revealed that stereochemistry of thujone was important for biological activity (β-thujone caused changes in aphid behavior while α-thujone did not) and that cyclopentane ring modifications and functional groups addition gave derivatives that possessed stronger and more durable deterrent effects. The most effective modification was the incorporation of a lactam moiety into the β-thujone molecule. Application of β-thujone lactam limited aphid settling for at least 24 h, caused restlessness in aphids and a delay or failure in reaching phloem phase by M. persicae. β-Thujone lactam can be considered a deterrent of medium potency with activity expressed at preingestive phase of aphid probing. Other compounds did not restrain aphid stylet penetration in non-phloem tissues but slightly limited sap ingestion (lactone, oxime), and restrained aphid settling for a period of less than 24 h (β-Thujone, bisulphite adduct, lactone).

Keywords: Beckmann rearrangement; Myzus persicae; antifeedants; α-thujone; β-thujone.

MeSH terms

  • Animals
  • Aphids / drug effects*
  • Bicyclic Monoterpenes
  • Cyclopentanes / chemistry
  • Insect Control
  • Lactams / chemistry*
  • Molecular Structure
  • Monoterpenes / chemistry
  • Monoterpenes / pharmacology*
  • Solanum tuberosum / parasitology*

Substances

  • Bicyclic Monoterpenes
  • Cyclopentanes
  • Lactams
  • Monoterpenes
  • beta-thujone