A Biologically Active Analog of the Sex Pheromone of the Emerald Ash Borer, Agrilus planipennis
- 539 Downloads
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.
KeywordsDodecan-12-olide (3Z)-dodecen-12-olide Lactone pheromone Agrilus planipennis Analog Buprestidae Invasive insect
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.
- Domingue MJ, Baker TC (2012) A multi-disciplinary approach for developing tools to monitor invasive buprestid beetle species. In: Blanco JJ, Fernandes AT (eds) Invasive species: threats, ecological impact and control methods. Nova, Hauppauge, pp 77–100Google Scholar
- EAB (2014) Emerald ash borer information website. http://www.emeraldashborer.info/faq.cfm#sthash.w6BvEr0c.dpbs. Accessed May 2014
- Fãrcasiu D, Jähme J, Rüchardt C (1985) Relative reactivity at bridgehead adamantyl and homoadamantyl substrates from solvolysis with heptafluorobutyrate as a highly reactive carbohydrate leaving group. Absence of SN2 character of solvolysis of tert-butyl derivatives. J Am Chem Soc 107:5717–5722CrossRefGoogle Scholar
- Francese JA, Mastro VC, Oliver JB, Lance DR, Youseff N, Lavalee SG (2005) Evaluation of colors for trapping Agrilus planipennis (Coleoptera: Buprestidae). J Entomol Sci 40:93–95Google Scholar
- Haack RA, Jendek E, Lui H, Marchant KR, Petrice T, Poland TM, Ye H (2002) The emerald ash borer: a new exotic pest in North America. Newsl Mich Entomol Soc 47:1–5Google Scholar
- Lelito JP, Fraser I, Mastro V, Tumlinson JH, BöröczkY K, Baker TC (2007) Visually mediated ‘paratrooper copulations’ in the mating behaviour of Agrilus planipennis (Coleoptera: Buprestidae), a highly destructive invasive pest of North American ash trees. J Insect Behav 20:537–552CrossRefGoogle Scholar
- R Development Core Team (2013) R: a language and environment for statistical computing. R Foundation for Statistical Computing, Vienna, Austria. ISBN 3-900051-07-0. Available from http://www.R-project.org. Accessed 2014
- Rodriguez-Saona C, Poland TM, Miller JR, Stelinski LL, Grant GG, De Groot P, Buchan L, MacDonald L (2006) Behavioural and electrophysiological responses of the emerald ash borer, Agrilus planipennis, to induced volatiles of Manchurian Ash, Fraxinus mandshurica. Chemoecology 16:75–86CrossRefGoogle Scholar
- Silk PJ, Ryall K, Mayo P, Lemay M, Grant G, Crook D, Cossé A, Fraser I, Sweeney JD, Lyons DB, Pitt D, Scarr T, Magee D (2011) Evidence for a volatile pheromone in Agrilus planipennis Fairmaire (Coleoptera: Buprestidae) that increases attraction to a host foliar volatile. Environ Entomol 40:904–916CrossRefPubMedGoogle Scholar
- van der Mee L, Helmich F, De Bruijn R, Vekemans JAJM, Palmans ARA, Meijer EW (2006) Investigation of lipase-catalysed ring-opening polymerization of lactones with various ring sizes. Kin Evaluat Macromol 39:5021–5027Google Scholar