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Journal of Chemical Ecology

, Volume 41, Issue 3, pp 294–302 | Cite as

A Biologically Active Analog of the Sex Pheromone of the Emerald Ash Borer, Agrilus planipennis

  • P. J. SilkEmail author
  • K. Ryall
  • P. Mayo
  • D. I. MaGee
  • G. Leclair
  • J. Fidgen
  • R. Lavallee
  • J. Price
  • J. McConaghy
Article

Abstract

The emerald ash borer, Agrilus planipennis (Coleoptera: Buprestidae) (EAB), is an invasive species causing unprecedented levels of mortality to ash trees in its introduced range. The female-produced sex pheromone of EAB has been shown to contain the macrocyclic lactone (3Z)-dodecen-12-olide. This compound and its geometrical isomer, (3E)-dodecen-12-olide, have been demonstrated previously to be EAG active and, in combination with a host-derived green leaf volatile, (3Z)-hexenol, to be attractive to male EAB in green prism traps deployed in the ash tree canopy. In the current study, we show that the saturated analog, dodecan-12-olide, is similarly active, eliciting an antennal response and significant attraction of EAB in both olfactometer and trapping bioassays in green traps with (3Z)-hexenol. Conformational modeling of the three lactones reveals that their energies and shapes are very similar, suggesting they might share a common receptor in EAB antennae. These findings provide new insight into the pheromone ecology of this species, highlighting the apparent plasticity in response of adults to the pheromone and its analog. Both of the unsaturated isomers are costly to synthesize, involving multistep, low-yielding processes. The saturated analog can be made cheaply, in high yield, and on large scale via Mitsunobu esterification of a saturated ω-hydroxy acid or more simply by Baeyer-Villiger oxidation of commercially available cyclododecanone. The analog can thus provide an inexpensive option as a lure for detection surveys as well as for possible mitigation purposes, such as mating disruption.

Keywords

Dodecan-12-olide (3Z)-dodecen-12-olide Lactone pheromone Agrilus planipennis Analog Buprestidae Invasive insect 

Notes

Acknowledgments

We thank Matt Brophy, Isabelle Ochoa, Sarah Crispell, and David Nisbet for technical help. We also thank the cities of Sault Ste. Marie and Milton, Ontario, and Montreal, Quebec. Specifically, we thank Anthony Daniel of the City of Montreal. We thank Jon Sweeney for a helpful review of an earlier draft of the manuscript. We thank Prof. Ghislain Deslongchamps (UNB) for his advice on the molecular modeling. This project was funded by Natural Resources Canada, Canadian Forest Service and SERG-I (FPL, OMNR). All experiments reported here comply with the laws of Canada.

Conflict of Interest

The authors declare that they have no conflict of interest.

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Copyright information

© Her Majesty the Queen in Right of Canada 2015

Authors and Affiliations

  • P. J. Silk
    • 1
    Email author
  • K. Ryall
    • 2
  • P. Mayo
    • 1
  • D. I. MaGee
    • 3
  • G. Leclair
    • 1
  • J. Fidgen
    • 2
  • R. Lavallee
    • 4
  • J. Price
    • 1
  • J. McConaghy
    • 1
  1. 1.Canadian Forest Service - Atlantic Forestry CentreNatural Resources CanadaFrederictonCanada
  2. 2.Canadian Forest Service - Great Lakes Forestry CentreNatural Resources CanadaSault Ste. MarieCanada
  3. 3.Department of ChemistryUniversity of New BrunswickFrederictonCanada
  4. 4.Ressources Naturelles Canada/ Natural Resources Canada, Service Canadien des Forêts/Canadian Forest ServiceQuébecCanada

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