The Rare North American Cerambycid Beetle Dryobius sexnotatus Shares a Novel Pyrrole Pheromone Component with Species in Asia and South America

J Chem Ecol. 2017 Aug;43(8):739-744. doi: 10.1007/s10886-017-0875-3. Epub 2017 Aug 5.

Abstract

The compound 1-(1H-pyrrol-2-yl)-1,2-propanedione ("pyrrole") is an important pheromone component of several Asian and South American species of longhorned beetles in the subfamily Cerambycinae. Here, we report the first confirmed identification of this compound as a pheromone component of a cerambycine species native to North America, the rare beetle Dryobius sexnotatus Linsley. Headspace volatiles from males contained (R)-3-hydroxyhexan-2-one and pyrrole (ratio 1:0.13), neither of which were detected in samples from a female. A field bioassay confirmed that adults of both sexes were attracted only to the binary blend of racemic 3-hydroxyhexan-2-one plus pyrrole, and not by either compound alone. Adults of another cerambycine, Xylotrechus colonus (F.), were attracted by 3-hydroxyhexan-2-one, consistent with this compound being the primary component of the pheromone of this species; attraction was not influenced by the presence of pyrrole. This study attests to the effectiveness of pheromone-baited traps in capturing rarely encountered species of cerambycids. It also provides further evidence that pyrrole represents another conserved pheromone motif within the Cerambycinae, now having been found in representatives of five cerambycid tribes from three continents.

Keywords: Aggregation-sex pheromone; Cerambycidae; Invasive species; Longhorned beetle; Reproductive isolation; Sex pheromone.

MeSH terms

  • Animals
  • Asia
  • Coleoptera / physiology*
  • Female
  • Hexanones / chemistry
  • Hexanones / pharmacology
  • Introduced Species
  • Male
  • Mass Spectrometry
  • North America
  • Pyrroles / chemistry
  • Pyrroles / pharmacology
  • Sex Attractants / chemistry
  • Sex Attractants / pharmacology*
  • Sexual Behavior, Animal / drug effects
  • South America

Substances

  • 3-hydroxyhexan-2-one
  • Hexanones
  • Pyrroles
  • Sex Attractants