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 electroantennographic detection (GC-EAD) and mass spectrometry (GC-MS), we detected (Z)-6,14-pentadecadienal in volatile collections and in whole body extracts of female A. erythrocephala. 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 corroborated 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.
Similar content being viewed by others
References
Ahlgren, G., Bergström, G., Löfqvist, J., Jansson, A., and Norin, T. 1979. Trans-perillenal A furanoid monoterpene from pine Saw-Fly, Neodiprion sertifer (Hymenoptera: Diprionidae). J. Chem. Ecol. 5: 309–319.
Allen, D. C. 2000. The pine false webworm in New York. pp. 30–32 in: LYONS, D. B., JONES G. C., AND SCARR, T. A. (eds.) Proceedings of a Workshop on the Pine False Webworm, Acantholyda erythrocephala (Hymenoptera: Pamphiliidae); 16 February 1998; Faculty of Forestry, University of Toronto. Ontario Ministry of Natural Resources of Ontario, Natural Resources Canada, Canadian Forest Service.
Anderbrant, O., Bengtsson, M., Löfqvist, J., and Baeckström, P. 1992. Field response of the pine sawfly Neodiprion sertifer to controlled release of diprionyl acetate, diprionyl propionate and trans-perillenal. J. Chem. Ecol. 18: 1707–1725.
Anderbrant, O., Löfqvist, J., Högberg, H.-E., Hedenström, E., Baldassari, N., Baronio, P., Kolmakova, G., Lyons, B., Naito, T., Odinokov, V., Simand, J., SupatashviLi, A., Tai, A., and Tourianov, R. 2000. Geographic variation in the field response of male European pine sawflies, Neodiprion sertifer, to different pheromone stereoisomers and esters. Entomol. Exp. Appl. 95: 229–239.
Anderbrant, O., Östrand, F., Bergström, G., Wassgren, A.-B., Auger-Rozenberg, M.-A., Geri, C., Hedenström, E., Högberg, H. E., Herz, A., and Heitland, W. 2005. Release of sex pheromone and its precursor in the pine sawfly Diprion pini (Hym., Diprionidae). Chemoecology. 15: 147–151.
Asaro, C., and Allen, D. C. 1999. Biology of pine false webworm (Hymenoptera: Pamphiliidae) during an outbreak. Canad. Entomologist. 131: 729–742
Asaro, C., and Allen, D. C. 2001. History of a pine false webworm (Hymenoptera: Pamphiliidae) outbreak in northern New York. Can. J. For. Res. 31: 181–185
Baker, R., Longhurst, C., Selwood, D., and Billany, D. 1983. Ortho-aminoacetophenone: a component of the sex pheromone system of the web-spinning larch sawfly, Cephalcia lariciphila wachtl. Experientia. 39: 993–994.
Bartelt, R. J., and Jones, R. L. 1983. (Z)-10-Nonadecenal: A Pheromonally Active Air Oxidation Product of (Z,Z) -9, 19 Dienes in Yellowheaded Spruce Sawfly. J. Chem. Ecol. 9, 1333–1341.
Bartelt, R. J., Jones, R. L., and Kulman, H. M. 1982a. Evidence for a multicomponent sex pheromone in the yellowheaded spruce sawfly. J. Chem. Ecol. 8, 83–94.
Bartelt, R. J., Jones, R. L., and Kulman, H. M. 1982b. Hydrocarbon components of the yellowheaded spruce saw fly sex pheromone: A Series of (Z, Z)-9, 19 Dienes. J. Chem. Ecol. 8, 95–114.
Bartelt, R. J., Jones, R. L., and Krick, T. P. 1983. (Z)-5-Tetradecen-1-ol: A Secondary Pheromone of the Yellowheaded Spruce Sawfly, and Its Relationship to (Z)-10-Nonadecenal. J. Chem. Ecol. 9, 1343–1352.
Bartelt, R.J., Cossé, A. A., Petroski, R.J., and Weaver, D.K. 2002. Cuticular hydrocarbons and novel alkenediol diacetates from wheat stem sawfly (Cephus cinctus): natural oxidation to pheromone components. J. Chem. Ecol. 28: 385–405.
Bergström, G., Wassgren, A.-B., Anderbrant, O., Fagerhag, J., Edlund, H., Hedenström, E., Högberg, H. -E., Geri, C., Auger, M. A., Varama, M., Hansson, B. S., and Löfqvist, J. 1995. Sex pheromone of the pine sawfly Diprion pini (Hymenoptera: Diprionidae): chemical identification, synthesis and biological activity. Experientia. 51: 370–380.
Bergström, G., Wassgren, A.-B., Anderbrant, O., Ochieng, S.A., Ostrand, F., Hansson, B. S., Hedenström, E., and Högberg, H. -E. 1998. The sex pheromone of the pine sawfly Microdiprion pallipes (Hymenoptera: Diprionidae). Naturwissenschaften. 85: 244–248.
Blomquist, G. J., Tillmanwall, J. A., Guo L, Quilici, D. R., Gu PD, and Schal C. 1993. Hydrocarbons and hydrocarbon derived sex-pheromones in insects – Biochemicstry and Endocrine Regulation. pp. 317–351 in Insect Lipids: Chemistry, Biochemistry and Biology D. W. Stanley-Samuelson and D. R. Nelson, eds. University of Nebraska Press, Lincoln.
Borden J. H., Billany, D. J. Bradshaw, J. W. S., Edwards, R. B., Baker, R., and Evans, D.A. 1978. Pheromone response and sexual behavior of Cephacia lariciphila Wachtl (Hymenoptera: Pamphiliidae). Ecol. Entom. 3: 13-23
Carlson, D. A., Roan, C.-S., Yost, R. A., and Hector, J. 1989. Dimethyl disulfide derivatives of long chain alkenes, alkadienes, and alkatrienes for gas chromatography/mass spectrometry. Anal. Chem. 61: 1564–1571.
Chen, G.F., Zhang, Q. H., Li, Z. Y., Miao, Z. W., Wang, L. Z., and Anderbrant, O. 1997. A preliminary study on the sex pheromone of Diprion jingyuanensis Xiao et Zhang. Chin. J. Biol. Control. 13: 61–64.
Claus, R. E., and Schreiber, S. L. 1986. Ozonolytic cleavage of cyclohexene to terminally differentiated products: Methyl 6-oxohexanoate, 6,6-dimethoxyhexanal, methyl 6,6-dimethoxyhexanoate. Org. Synth. 64: 150–156.
Corey, E. J., and Schmidt, G. 1979. Useful procedures for the oxidation of alcohols involving pyridium dichromate in aprotic media. Tetrahed. Lett. 5: 399–402
Cossé A. A, and Bartelt R. J. 2000. Male-produced aggregation pheromone of Colopterus truncatus: Structure, electrophysiological, and behavioral activity. J. Chem. Ecol. 26: 1735–1748.
Cossé A. A., Bartelt R. J., James, D. G, and Petroski R.J. 2001. Identification of a female-specific, antennally active volatile compound of the currant stem girdler. J. Chem. Ecol. 27: 1841–1853.
Cossé, A. A., Bartelt, R. J., Weaver, D. K., and Zilkowski, B. W. 2002. Pheromone components of the wheat stem sawfly: identification, electrophysiology, and field bioassay. J. Chem. Ecol. 28: 407–423
Ellison, R. A., Lukenbach, E. R., and Chiu, C.-W. 1975. Cyclopenenone synthesis via aldol condensation: Synthesis of a key prostaglandin intermediate. Tetrahedron Lett. 1975: 499–502.
FRANKEL, E. N. 1998. Lipid Oxidation. Oily Press, Dundee, Scotland.
Hedenström, E., Edlund, H., Wassgren, A.-B., Bergström, G., Anderbrant, O., Östrand, F., Sierpinski, A., Auger-Rozenberg, M. A., Herz, A., Heitland, W., and Varama, M. 2006. Sex pheromone of the pine sawfly, Gilpinia pallida: chemical identification, synthesis, and biological activity. J. Chem. Ecol. 32: 2525-2541.
Helson, B., Lyons, B., and De Groot, P. 1999. Evaluation of neem EC formulations containing azadirachtin for forest insect pest management in Canada. Azadirachta Indica a. Juss. 79–89.
Howard, R.W., 1993, Cuticular hydrocarbons and chemical communication, pp. 179–226 in: Insect Lipids: Chemistry, Biochemistry and Biology, D. W. Stanley-Samuelson and D. R. Nelson, eds. University of Nebraska. Press, Lincoln.
Howard R, W, and Blomquist G, J. 2005. Ecological, behavioral, and biochemical aspects of insect hydrocarbons. Annu. Rev.Entomol. 50: 371–393.
Jahn, E. 1967. On a population outbreak of the pine false webworm, Acantholyda erythrocephala Chr. in the Steinfeld, Lower Austria in the years 1964–1967. Anz. Schaedingskd. 39: 145–152.
Jewett, D. M., Matsumura, F., and Coppel, H. C. 1976. Sex pheromone specificity in the pine sawflies: interchange of acid moieties in an ester. Science. 192: 51–53.
Johnson, W. T., and Lyon, H H. 1991. Insects that Feed on Trees and Shrubs. Comstock Pub. Associates, Ithaca. NY.
Johnson, D. K., Donohoe, J., and Kang, J. 1994. Dilithium tetrarchlorocuprate catalyzed coupling of allylmagnesium bromide with α,ω-dihaloalkanes. Synth. Comm. 24: 1557–1564.
Kenis, M., and Kloosterman, K. 2001. European Parasitoids of the Pine False Webworm (Acantholyda erythrocephala (L.) and Their Potential for Biological Control in North America.
Lyons. D. B. 1994. Development of the aboreal stages of the pine false webworm (Hymenoptera: Pamphiliidae). Env. Entomol. 23: 846–854
Lyons, D. B. 1999. Phenology of the native parasitoid Sinophorus megalodontis (Hymenoptera: Ichneumonidae) relative to its introduced host, the pine false webworm (Hymenoptera: Pamphiliidae). Canad. Entomologist. 131: 787–800.
Lyons D. B., Helson B. V., Jones G. C., and McFarlane J. W. 1993. Development of a chemical control strategy for the Pine False Webworm, Acantholyda erythrocephala (L.) (Hymenoptera: Phamphiliidae) Canad. Entomologist. 125: 499–511
Lyons, D. B., Helson B.V, Jones, G.C., Mcfarlane, J,W., and Scarr, T. 1996. Systemic activity of neem seed extracts containing azadirachtin in pine foliage for control of the pine false webworm, Acantholyda erythrocephala (Hymenoptera: Pamphiliidae). Proc. Entomol. Soc.Ontario 127: 45–55.
Lyons, D. B., Helson, B.V, Jones G. C, and Mcfarlane J.W. 1998. Effectiveness of Neem- and diflubenzuron-based insecticides for control of the pine false webworm, Acantholyda erythrocephala (L.) (Hymenoptera: Pamphiliidae). Proc. Entomol. Soc.Ontario 129: 115–126.
Lyons D. B., Helson B.V., Thompson D. G., McFarlane J.W., Robinson A. G., and Mickle R. E. 2003. Efficacy of ultra-low volume aerial application of an azadirachtin-based insecticide for control of the pine false webworm, Acantholyda erythrocephala (L.) (Hymenoptera : Pamphiliidae), in Ontario, Canada. Intl, J. Pest Manag. 49: 1–8,
Mayfield A. E., Allen D. C., and Briggs R. D. 2005. Radial growth impact of pine false webworm defoliation on eastern white pine. Canad. J. Forest Res.-Revue Canadienne De Recherche Forestiere 35: 1071–1086.
McGuire, M.R., Behle, R.W., Goebel, H.N., and Fry, T.C. 2000. Calibration of a sunlight simulator for determining solar stability of Bacillus thuringiensis and Anagrapha falcifera nuclear polyhedrovirus Environm. Entomol. 29: 1070–1074
MiddleKauff, W. W. 1938. Occurrence of a European sawfly Acantholyda. erythrocephala (L.) in New York State. J. Entomol. Soc. New York, 46: 438.
MiddleKauff, W. W. 1958. North American sawflies of the genera Acantholyda, Cephalcia, Neurotoma (Hymenoptera Pamphiliidae) Univ. Calif. Publ. Entomol. 14: 51–174
Miyashita, N., Yoshikoshi, A., and Grieco, P. A. 1977. Pyridinium p-toluenesulfonate: a mild and efficient catalyst for the tetrahydropyranylation of alcohols. J. Org. Chem. 42: 3772–3774.
Moody, B. H. 1990. Forest insect and disease conditions in Canada, 1988. Forest Insect and Disease Survey. Forestry Canada Ottawa, Ont.
Ostrand, F., Anderbrant, O., Wassgren, A.B., Bergström, G., Hedenström, E., Högberg, H.E., Ba Vu, N., and Larsson, M. 2003. Stereoisomeric composition of the sex pheromone of the pine sawfly Microdiprion pallipes (Hym., Diprionidae). Chemoecology. 13: 155–162.
Siegel, S. and Castellan, N. J. 1988. Nonparametric Statistics for the Behavioural Sciences. New York. McGraw-Hill.
Smith, D. R. 1993. Systematics, life history, and distribution of sawflies. pp. 3–32 in Sawfly Life History Adaptations to Woody Plants. Wagner, M. R.; Raffa, K. F (eds).
Sonnet, P. E. 1974. cis-Olefins from the Wittig reaction. Org. Prep. Proced. Int. 6: 269–273.
Staples, J. K., 1999. Semiochemicals of the Pine False Webowrm Acantholyda erythrocephala (L.) (Hymenoptera: Pamphiliidae). M.S. thesis State University of New York College of Environmental Science and Forestry. Syracuse New York.
StatSoft, Inc. (2001). STATISTICA (data analysis software system), version 6. www.statsoft.com.
Steiner, S., Mumm, R., and Ruther, J. 2007. Courtship Pheromones in parasitic wasps: Comparison of bioactive and inactive hydrocarbon profiles by multivariate statistical methods. J. Chem. Ecol. 33: 825–838.
Swedenborg, P.D., and Jones, R.L. 1992. (Z)-4-tridecenal, a pheromonally active air oxidation product from a series of (Z,Z)-9,13-dienes in Macrocentrus grandii Goidanich (Hymenoptera: Braconidae). J. Chem. Ecol. 18: 1913–1931.
Syme, P. D. 1981. Occurrence of the introduced sawfly Anantholyda erythrocephala (L.) in Ontario. Dept. of the Env. Can. For. Servc, Attawa, Ont. Res. Notes 1: 4–5
Tai, A., Higashiura, Y., Kakizaki, M., Naito, T., Tanaka, K., Fujita, M., Sugimura, T., Hara, H., and Hayashi N. 1998. Field and electroantennogram responses of the pine sawfly, Diprion nipponica, to chiral synthetic pheromone candidates. Biosci. Biotechnol. Biochem. 62: 607–608.
TAI, A., SYOUNO, E., TANAKA, K., FUJITA, M., SUGIMURA, T., HIGASHIURA, Y., KAKIZAKI, M. HARA, H., NAITO, T. 2002. Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica. Bull Chem Soc Jpn. 75: 111–121.
Thompson, D.G., Mickle, R.E., Lyons, D.B., Helson, B.V., Robinson, A.G., Chartrand, D.T., and Buscarini, T.M., 2003 Deposition of azadirachtin following ultra-low volume aerial applications to red pine plantations for control of pine false webworm, Acantholyda erythrocephala (L.) (Hymenoptera: Pamphiliidae), in Ontario, Canada. Intl. J. Pest Manag. 49: 9–15
Wassgren, A.B., Bergström, G., Sierpinski, A., Anderbrant, O., Högberg, H.E., and Hedenström, E. 2000. Sex pheromone of the pine sawfly Macrodiprion nemoralis (Hymenoptera: Diprionidae): Identification of (2S,3R,7R,9S)-3,7,9-trimethyl-2-tridecanol as the precursor for the active pheromone acetate. Naturwissenschaften. 87: 24–29.
WILEY SPECTRAL LIBRARY [CD-Rom], 6th ed 1995, Wiley New York.
Wilson, G.G. 1984. Infection of the pine false webworm by Pleistophora schubergi (Microsporida). Canad. For. Service Res. Notes. 4: 7–8.
Acknowledgments
We thank Robert Behle of the USDA-ARS-NCAUR in Peoria, Illinois for use of the solar simulator, and the Illinois Department of Natural Resources for access to Sand Ridge State Forest.
Author information
Authors and Affiliations
Corresponding author
Additional information
An erratum to this article can be found at http://dx.doi.org/10.1007/s10886-010-9759-5
Rights and permissions
About this article
Cite this article
Staples, J.K., Bartelt, R.J., Cossé, A.A. et al. Sex Pheromone of the Pine False Webworm Acantholyda erythrocephala . J Chem Ecol 35, 1448–1460 (2009). https://doi.org/10.1007/s10886-009-9736-z
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10886-009-9736-z