Submitted to: Journal of Chemical Ecology
Publication Type: Peer reviewed journal
Publication Acceptance Date: 6/17/2003
Publication Date: 10/20/2003
Citation: Gries, R., Khaskin, G., Khaskin, E., Foltz, J.L., Schaefer, P.W., Gries, G. 2003. Enantiomers of (Z,Z)-6,9-Heneicosadien-11-01: Sex pheromone components of Orgyia detrita. Journal of Chemical Ecology. 29(10):2201-2212 Interpretive Summary: Threatened and endangered species present special problems for land managers and regulatory officials. Areas where they occur need to be managed carefully, whereas areas where they have already been extirpated might be better used for commercial development or other purposes. In addition, such species might actually have wider distributions than those based on known sightings. A rather rare tussock moth, Orgyia detrita, occurs along the east and gulf coasts of the United States and is associated mainly with live oak, Quercus virginiana, upon which the caterpillars feed. Populations in Gainesville, Florida, in recent years permitted collection, laboratory rearing, and analyses of the sex pheromone gland extract from females moths. Using coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC mass spectrometry, scientists from USDA Agricultural Research Service, Simon Fraser University (Burnaby, BC), and the University of Florida have identified the sex pheromone as (Z,Z)-6,9-heniosadien-11-ol. Field testing with synthetic standards revealed that a 1:1 ratio of Z6Z9-11S-ol-C21 and Z6Z9-11R-ol-C21 captured most male moths under field conditions. Scientists responsible for environmental monitoring now have a usable synthetic lure (although further development of a proper dispenser must be addressed), and sampling O. detrita males for population monitoring or distributional studies is now possible. Because females are the critical gender for population replacement, this strategy could be used safely for studies on other moth species.
Technical Abstract: (Z,Z)-6,9-(S)-11-Heneicosadienol (Z6Z9-11S-o1-C21) and (Z,Z)-6,9-(R)-11-heneicosadienol (Z6Z9-11R-o1-C21) are major sex pheromone components of female tussock moths, Orgyia detrita Guerin-Meneville (Lepidoptera: Lymantriidae). This conclusion is based on: 1) analyses of pheromone glad extracts of female O. detrita by coupled gas chromatographic-electroantennopgraphic detection (GC-EAD) and GC mass spectrometry, and 2) field trapping experiment with synthetic standards. In these experiments, Z6Z9-11S-o1-C21 and Z6Z9-11R-o1-C21 in combination, but not singly, attracted significant numbers of male moths. A 1:1 ratio of Z6Z9-11S-o1-C21 and Z6Z9-11R-o1-C21 was more attractive than the 1:3.5 (R:S) blend ratio determined in pheromone extracts. Lower and higher homologues of Z6Z9-11-o1-C21 were also detected in GC-EAD recordings of pheromone extracts, and enhanced attractiveness of Z6Z9-o1-C21 in field experiments. Whether their enantiomer composition is equivalent to that of Z6Z9-11-o1-C21 is yet to be determined. This is the first report of secondary alcohols as pheromone components in the ditrysian (advanced) Lepidoptera.