Journal of Chemical Ecology

, Volume 29, Issue 10, pp 2201–2212 | Cite as

Enantiomers of (Z,Z)-6,9-Heneicosadien-11-OL: Sex Pheromone Components of Orgyia detrita

  • Regine Gries
  • Grigori Khaskin
  • Eugene Khaskin
  • John L. Foltz
  • Paul W. Schaefer
  • Gerhard GriesEmail author


(6Z,9Z,11S)-6,9-Heneicosadien-11-ol (Z6Z9-11S-ol-C21) and (6Z,9Z,11R)-6,9-heneicosadien-11-ol (Z6Z9-11R-ol-C21) were identified as major sex pheromone components of female tussock moths, Orgyia detritaGuérin-Méneville (Lepidoptera: Lymantriidae), on the basis of (1) analyses of pheromone gland extracts of female O. detrita by coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC mass spectrometry, and (2) field trapping experiments with synthetic standards. Z6Z9-11S-ol-C21 and Z6Z9-11R-ol-C21 in combination, but not singly, attracted significant numbers of male moths. Racemic Z6Z9-11-ol-C21 was more attractive than the 1:3.5 (R:S) blend ratio found in pheromone gland extracts from female moths. Lower and higher homologues of Z6Z9-11-ol-C21 were also detected in GC-EAD recordings of pheromone extracts, and the racemic compounds enhanced attractiveness of Z6Z9-11-ol-C21 in field experiments. Because of trace amounts of these homologues in extracts, their enantiomeric composition could not be determined. This is the first report of secondary alcohols as pheromone components in the ditrysian (advanced) Lepidoptera.

Ditrysian Lepidoptera Lymantriidae Orgyia detrita sex pheromone (6Z,9Z,11S)-6 9-heneicosadien-11-ol (6Z,9Z,11R)-6,9-henei-cosadien-11-ol,(6Z,9Z)-6,9-eicosadien-11-ol,(6Z,9Z)-6,9-docosadien-11-ol 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Ando, T., Ohtani, K., Yamamoto, M., Miyamoto, T., Qin, X. R., and Witjaksono. 1997. Sex pheromone of Japanese giant looper, Ascotis selenaria cretacea: Identification and field tests. J. Chem. Ecol. 23:2413–2423.Google Scholar
  2. Arn, H., Städler, E., and Rauscher, S. 1975. The electroantennographic detector—A selective and sensitive tool in the gas chromatographic analysis of insect pheromones. Z. Naturforsch. 30c:722–725.Google Scholar
  3. Bell, R. A., Owens, C. D., Shapiro, M., and Tardif, J. R. 1981. Mass rearing and virus production, pp. 599–655, in C. C. Doane and M. L. McManus (Eds.). The Gypsy Moth: Research Toward Integrated Pest Management. U. S. Dept. Agric. Tech. Bull. 1584, 757 pp.Google Scholar
  4. Brown, A. L. and Ahuja, V. K. 1973. “P-2 nickel” catalyst with ethylenediamine, a novel system for highly stereospecific reduction of alkynes to cis-olefins. J. Chem. Soc., Chem. Commun. 553–554.Google Scholar
  5. Chow, Y. S., Tsai, R. S., Gries, G., Gries, R., and Khaskin, G. 2001. Preliminary identification of the sex pheromone of Orgyia postica (Walker) (Lepidoptera: Lymantriidae). Entomol. Sin. 8:13–20.Google Scholar
  6. Drooz, A. T., Smith, T. F., and Doggett, C. A. 1986. Outbreak of a rare lymantriid, Orgyia detrita, in coastal North Carolina. U. S. Dept. Agric., Forest Service, Southeastern For. Exp. Stn., Res. Note, SE-340, 3 pp.Google Scholar
  7. Ferguson, D. C. 1978. The Moths of America North of Mexico, Fasc. 22.2, Noctuoidea (in Part): Lymantriidae. E. W. Classey Ltd., Oxfordshire, England, 110 p.Google Scholar
  8. Gray, T. G., Slessor, K. N., Shepherd, R. F., Grant, G. G., and Manville, J. F. 1984. European pine shoot moth, Rhyacionia buoliana (Lepidoptera: Tortricidae): Identification of additional pheromone components resulting in an improved lure. Can. Entomol. 116:1525–1532.Google Scholar
  9. Gries, G., Clearwater, J., Gries, R., Khaskin, G., King, S., and Schaefer, P. 1999a. Synergistic sex pheromone components of white-spotted tussock moth, Orgyia thyellina. J. Chem. Ecol. 25:1091–1104.Google Scholar
  10. Gries, G., Gries, R., Schaefer, P. W., Gotoh, T., and Higashiura, Y. 1999b. Sex pheromone components of pink gypsy moth, Lymantria mathura. Naturwissenschaften 86:235–238.Google Scholar
  11. Gries, G., Slessor, K. N., Gries, R., Khaskin, G., Wimalaratne, P. D. C., Gray, T. G., Grant, G. G., Tracey, A. S., and Hulme, M. 1997. (Z)-6,(E)-8–Heneicosadien-11–one: Synergistic sex pheromone component of Douglas-fir tussock moth, Orgyia pseudotsugata (McDunnough) (Lepidoptera: Lymantriidae). J. Chem. Ecol. 23:19–34.Google Scholar
  12. König, W. A., Gehrcke, B., Icheln, D., Evers, P., Dönnecke, J., and Wang, W. 1992. New selectively substituted cyclodextrins as stationary phases for the analysis of chiral constituents of essential oils. J. High Resolut. Chromatogr. 15:367–372.Google Scholar
  13. Kozlov, M. V., Zhu, J., Philipp, P., Francke, W., Zvereva, E. L., Hansson, B. S., and Löfstedt, C. 1996. Pheromone specificity in Eriocrania semipurpurella (Stephens) and E. sangii (Wood) (Lepidoptera: Eriocraniidae) based on chirality of semiochemicals. J. Chem. Ecol. 22:431–454.Google Scholar
  14. Little, E. L., Jr. 1971. Atlas of United States Trees, Vol. 1. Conifers and Important Hardwoods. U.S. Dept. Agric., Forest Service, Misc. Publ. No. 1146, 9 pp., 94 maps.Google Scholar
  15. Liu, W. 1999. Semiochemistry of Orgyia and Diatraea lepidopteran species and affinity labelling of 2,3–oxidosqualene cyclase. PhD Thesis, Department of Chemistry, Simon Fraser University.Google Scholar
  16. Löfstedt, C., Hansson, B. S., Petersson, E., Valeur, P., and Richards, A. 1994. Pheromonal secretions from glands on the Vth abdominal sternite of hydropsychid and rhyacophilid caddisflies (Trichoptera). J. Chem. Ecol. 20:153–170.Google Scholar
  17. Millar, J. G., Giblin, M., Barton, D., Morrison, A., and Underhill, E. W. 1990. Synthesis and field testing of enantiomers of 6Z,9Z-cis-epoxydienes as sex attractants for geometrid moths. Interaction of enantiomers and regioisomers. J. Chem. Ecol. 16:2317–2339.Google Scholar
  18. Millar, J. G., Giblin, M., Barton, D., and Underhill, E. W. 1991. Chiral lepidopteran sex attractants: Blends of optically active C20 and C21 diene epoxides as sex attractants for geometrid and noctuid moths (Lepidoptera). Environ. Entomol. 20:450–457.Google Scholar
  19. Pietruszka, J., Hochmut, D. H., Gehrcke, B., Icheln, D., Runge, T., and König, W. A. 1992. Gas chromatographic enantioseparation of allenes. Tetrahedron Asymm. 3:661–670.Google Scholar
  20. Rodriguez, A. R. and Spur, B. W. 2001. Total synthesis of aspirin triggered 15–lipoxin A4. Tetrahedron Lett. 42:6057–6060.Google Scholar
  21. Sas/Stat. 1988. User's Guide, release 6.03 edition. SAS Institute, Cary, North Carolina.Google Scholar
  22. Smith, R. G., Daterman, G. E., and Daites, G. D., Jr. 1975. Douglas-fir tussock moth: Sex pheromone identification and synthesis. Science 188:63–64.Google Scholar
  23. Takano, S., Samizu, K., Sugihara, T., and Ogasawara, K. 1989. Asymmetric construction of optically active 3–hydroxyalkyne functionalities. J. Chem. Soc., Chem. Commun. 1344–1345.Google Scholar
  24. Tóth, M., Szöcs, G., Van Nieukerken, E., Philipp, P., Schmidt, F., and Francke, W. 1995. Novel type of sex pheromone structure identified from Stigmella malella (Stainton) (Lepidoptera: Nepticulidae). J. Chem. Ecol. 21:13–27.Google Scholar
  25. Van Den Dool, H. and Kratz, P. D. 1963. A generalization of the retention index system including linear temperature programmed gas–liquid partition chromatography. J. Chromatogr. 2:463–471.Google Scholar
  26. Wakamura, S., Arakaki, N., Yamamoto, M., Hiradate, S., Yasui, H., Yasuda, T., and Ando, T. 2001. Posticlure: A novel trans-epoxide as a sex pheromone component of the tussock moth, Orgyia postica (Walker). Tetrahedron Lett. 42:687–689.Google Scholar
  27. Winter, W. D., Jr. 2000. Basic techniques for observing and studying moths and butterflies. The Lepidopterists' Society, Memoir No. 5, Los Angeles, California, 444 pp.Google Scholar
  28. Xiao, L. and Kitazume, T. 1997. Optically active propargylic and allylic alcohols with a difluoromethyl group at the terminal carbon. Tetrahedron Asymm. 8:3597–3601.Google Scholar
  29. Zar, J. H. 1984. Biostatistical Analysis. Prentice-Hall, Englewood Cliffs, New Jersey.Google Scholar
  30. Zhu, J., Kozlov, M. V., Philipp, P., Francke, W., and Löfstedt, C. 1995. Identification of a novel moth sex pheromone in Eriocrania cicatricella (Zett.) (Lepidoptera: Eriocraniidae) and its phylogenetic implications. J. Chem. Ecol. 21:29–43.Google Scholar

Copyright information

© Plenum Publishing Corporation 2003

Authors and Affiliations

  • Regine Gries
    • 1
  • Grigori Khaskin
    • 1
  • Eugene Khaskin
    • 1
  • John L. Foltz
    • 2
  • Paul W. Schaefer
    • 3
  • Gerhard Gries
    • 1
    Email author
  1. 1.Department of Biological SciencesSimon Fraser UniversityBurnabyCanada
  2. 2.Department of Entomology & NematologyUniversity of FloridaGainesvilleUSA
  3. 3.United States Department of AgricultureAgricultural Research Service, Beneficial Insects Introduction Research LaboratoryNewarkUSA

Personalised recommendations