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

Journal of Chemical Ecology
P J SilkJ McConaghy

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. T...Continue Reading

References

Apr 18, 1997·The Journal of Organic Chemistry·Takashi MinoMasakazu Yamashita
Nov 25, 2003·Journal of Chemical Information and Computer Sciences·Rozália VanyúrJudit Jakus
Sep 14, 2006·Annual Review of Entomology·Samantha M CookJohn A Pickett
Jun 16, 2009·The Journal of Experimental Biology·Joelle Lemmen, Maya Evenden
Jan 29, 2010·Journal of Chemical Ecology·Damon J Crook, Victor C Mastro
Sep 23, 2010·Journal of Economic Entomology·Joseph A FranceseVictor C Mastro

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