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

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.

Propagation, synchrony, and impact of introduced and native Laricobius spp. (Coleoptera: Derodontidae) on hemlock woolly adelgid in Virginia.

Synchrony and impact of the predators Laricobius nigrinus Fender and Laricobius rubidus LeConte, on hemlock woolly adelgid, Adelges tsugae Annand, were studied in an eastern hemlock field insectary in Virginia. First, a field insectary for propagation of the introduced L. nigrinus was established by planting hemlocks in 2001, infesting them with hemlock woolly adelgid in 2002 and 2003, followed by releasing 258 L. nigrinus in 2003. Initial sampling showed that the native L. rubidus was present in the area. Hemlock woolly adelgid and both Laricobius species populations increased annually, from which 305 F3 L. nigrinus adults were collected and redistributed to forests in 2007. Second, the phenology of hemlock woolly adelgid and Laricobius spp. life cycles were monitored in 2005 and 2006. Adult L. nigrinus (F2) and L. rubidus were active on hemlock from fall through mid-spring and overlapped with second-instar sistentes nymphs through progredientes eggs. The predators' eggs were oviposited and larvae developed (i.e., F3 L. nigrinus) from late winter to mid-spring on progredientes eggs, indicating synchrony with suitable prey life stages. Third, a predator exclusion experiment was used to examine the relationships between the predators and prey in 2005 and 2006. When exposed to L. nigrinus (F2 adults and F3 larvae) and L. rubidus, hemlock woolly adelgid survival and ovisac density were lower and ovisac disturbance was higher than hemlock woolly adelgid protected in cages. The establishment and production of L. nigrinus at a field insectary, synchronization with, and impacts on hemlock woolly adelgid after a small release 2 yr earlier makes it an important potential biological control agent of hemlock woolly adelgid.