Sex Pheromone of the Pine False Webworm Acantholyda erythrocephala Joseph K. Staples & Robert J. Bartelt & Allard A. Cossé & Douglas W. Whitman Received: 24 September 2009 / Revised: 16 December 2009 / Accepted: 16 December 2009 / Published online: 12 January 2010 # Springer Science+Business Media, LLC 2010 Abstract Females of the pine false webworm Acantholyda erythrocephala (L) produce the sex pheromone (Z)-6, 14-pentadecadienal, which attracts flying males in the field. By using gas chromatography coupled with electroantenno- graphic detection (GC-EAD) and mass spectrometry (GC-MS), we detected (Z)-6,14-pentadecadienal in volatile collec- tions and in whole body extracts of female A. erythroce- phala. Females, but not males, also exhibited a 25-carbon cuticular hydrocarbon, ( Z,Z)-1,9,15-pentacosatriene, which can oxidize to (Z)-6,14-pentadecadienal upon exposure to air and sunlight. (Z,Z)-1,9,15-Pentacosatriene and (Z)-6,14-pentadecadienal identifications were corrob- orated by comparison with synthetic standards. (Z)-6, 14-Pentadecadienal is the second pheromone identified for pamphilliid sawflies, and the first to elicit strong field attraction, and thus offer potential as a pheromone lure to aid in control of this forest pest. Keywords Sex pheromone . Pine false webworm . Sawfly . Acantholyda erythrocephala . Cuticular hydrocarbon . Abitotic oxidation . Nonanal . Decanal . (Z)-6,14- pentadecadienal . Pentacosane . (Z)-9-pentacosene . (Z)-1,9-pentacosadiene . (Z,Z)-1,9,15-pentacosatriene . Hymenoptera . Pamphiliidae Introduction Acantholyda erythrocephala (L) (Hymenoptera: Pamphilii- dae), the pine false webworm (PFW), is common to northern Europe and Asia (MiddleKauff 1958). It was reported in North America during the early 1900’ s where it has become a significant pest of white pine (Pinus strobus L.), red pine (P. resinosa Ait), and Scots pine (P. sylvestris L) in both forests and plantations (Syme 1981; Johnson and Lyon 1991; Allen 2000). Outbreaks in the U.S. and Canada can encompass thousands of hectares and persist for 20 yr or more (Asaro and Allen 1999; Allen 2000, personal observa- tion), resulting in a growth reduction and increased mortality of host trees (MiddleKauff 1958; Syme 1981; Moody 1990; Lyons 1994; Asaro and Allen 2001; Mayfield et al. 2005). Numerous strategies considered as a means of control for this pest have met with variable success including: applica- tion of synthetic pesticides (Lyons et al. 1993), natural toxins such as neem extracts (Helson et al. 1999; Lyons et al. 1996, 1998, 2003), biological control (Wilson 1984; Lyons 1999; Kenis and Kloosterman 2001; Thompson et al. 2003). However, many of these strategies require precise knowledge of the distribution and phenology of PFW over large tracts of forest. As such, a pheromone lure could be valuable for monitoring, trapping, or disrupting A. erythrocephala. J. K. Staples (*) Department of Environmental Science, University of Southern Maine, 37 College Avenue, Gorham, ME 04038, USA e-mail: jstaples@usm.maine.edu R. J. Bartelt : A. A. Cossé Crop Bioprotection Research Unit, USDA, ARS National Center for Agricultural Utilization Research, Peoria, IL 61604, USA D. W. Whitman 4120 School of Biological Sciences, Illinois State University, Normal, IL 61790, USA J Chem Ecol (2009) 35:1448–1460 DOI 10.1007/s10886-009-9736-z