Journal of Chemical Ecology

, Volume 19, Issue 6, pp 1057–1062 | Cite as

Chirality of 5,11-dimethylheptadecane, the major sex pheromone component of the hemlock looper,Lambdina fiscellaria (Lepidoptera: Geometridae)

  • Jianxiong Li 
  • R. Gries
  • G. Gries
  • K. N. Slessor
  • G. G. S. King
  • W. W. Bowers
  • R. J. West
Article

Abstract

Of the four possible stereoisomers of 5,11-dimethylheptadecane, the major sex pheromone component of the eastern hemlock looper (EHL),Lambdina fiscellaria fiscellaria Guen., and the western hemlock looper (WHL),Lambdina fiscellaria lugubrosa Hulst, (5R,11S)-5,11-dimethylheptadecane was the only stereoisomer eliciting electrophysiological responses by male EHL and WHL antennae. In field bioassays with EHL and WHL populations, traps baited with (5R,11S)-5, 11-dimethylheptadecane caught as many males as did traps baited with all four stereoisomers combined or a synthetic mixture of 5,11-dimethylheptadecanes. Catches in traps baited with the other three stereoisomers did not significantly differ from those in the unbaited control traps. We conclude that male antennae lack chemoreceptors for the other three stereoisomers of 5,11-dimethylheptadecane and hypothesize that only (5R,115)-5,11-dimethylheptadecane is produced by female EHLs and WHLs.

Key words

Lepidoptera Geometridae eastern hemlock looper western hemlock looper sex pheromone pheromone chirality dimethylated hydrocarbons field trapping electrophysiological recordings (5R, 11S)-5 11-di-methylheptadecane (55,11R-5 11-dimethylheptadecane (5R, 11R-5 11-di-methylheptadecane (5S,11S)-5 11-dimethyIheptadecane 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Arn, H., Städler, E., andRauscher, 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
  2. Borden, J.H. 1985. Aggregation pheromones, pp. 257–285,in G.A. Kerkut and L.I. Gilbert (eds.). Comprehensive Insect Physiology, Biochemistry, and Pharmacology, Vol. 9. Pergamon Press, New York.Google Scholar
  3. Carpita, A., De Magistris, E., andRossi, R. 1989. The racemic form and the two enantiomers of 4-methyl-1-nonanol, a sex attractant of the yellow mealworm,Tenebrio molitor L.Gazz. Chim. Ital. 119:99–105.Google Scholar
  4. Gries, G., Gries, R., Borden, J.H., Jianxiong Li, Slessor, K.N., King, G.G.S., Bowers, W.W., West, R.J., andUnderhill, E.W. 1991a. 5,11-Dimethylheptadecane and 2,5-dimethylhep-tadecane: Sex pheromone components of the geometrid moth,Lambdina fiscellaria fiscellaria. Naturwissenschaften 78:315–317.Google Scholar
  5. Gries, G.,Jianxiong Li., Gries, R.,Slessor, K.N.,Bowers, W.W.,West, R.J.,King, G.G.S.,Underhill, E.W., andBorden, J.H. 1991b. Method and composition for attracting and controlling hemlock looper. Canadian Patent Application #2,041,529-1.Google Scholar
  6. Gries, G.,Gries, R.,Krannitz, S.H.,Li, J.,King, G.G.S.,Slessor, K.N.,Borden, J.H.,Bowers, W.W.,West, R.J., andUnderhill, E.W. 1993. Sex pheromone of the western hemlock looper,Lambdina fiscellaria lugubrosa (Hulst).J. Chem. Ecol. in press.Google Scholar
  7. Li, J. 1993. Identification and chiral synthesis of sex pheromone components in geometrid moths (Lepidoptera: geometridae). PhD thesis. Simon Fraser University, Burnaby, British Columbia, Canada.Google Scholar
  8. Mayer, M.S., andMcLaughlin, J.R. 1991. Handbook of Insect Pheromones and Sex Attractants. CRC Press, Boca Raton, Florida.Google Scholar
  9. McDowell, P.G., Hassanali, A., andDransfield, R. 1985. Activity of diastereoisomers of 13,23-dimethylpentatriacontane, the sex pheromone ofGlossina pallidipes, and comparison with the natural pheromone.Physiol. Entomol. 10:183–190.Google Scholar
  10. Millar, J.G., Giblin, M., Barton, D., andUnderhill, E.W. 1990a. (3Z,6Z,9Z)-Nonadecatriene and enantiomers of (3Z,9Z)-cis-6,7-epoxy-nonadecadiene as sex attractants for two geometrid and one noctuid moth species.J. Chem. Ecol. 16:2153–2166.Google Scholar
  11. Millar, J.G., Giblin, M., Barton, D., Morrison, A., andUnderhill, E.W. 1990b. Synthesis and field testing of enantiomers of 6Z,9Z-cis-3,4-epoxydienes as sex attractants for geometrid moth. Interactions of enantiomers and regioisomers.J. Chem. Ecol. 16:2317–2339.Google Scholar
  12. Millar, J.G., Giblin, M., Barton, D., andUnderhill, 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
  13. Tóth, M., Helmchen, G., Leikauf, U., Szöcs, G., andSzöcs, G. 1989. Behavioral activity of optical isomers of 5,9-dimethylheptadecane, the sex pheromone ofLeucoptera scitella L. (Lepidoptera: Lyonetiidae).J. Chem. Ecol. 15:1535–1543.Google Scholar
  14. Vanderwel, D., andOehlschlager, A.C. 1987. Biosynthesis of pheromones and endocrine reg-ulation of pheromone production in Coleoptera, pp. 175–215,in G.D. Prestwich and G.J. Blomquist (eds.). Pheromone Biochemistry. Academic Press, Orlando, Florida.Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • Jianxiong Li 
    • 1
  • R. Gries
    • 2
  • G. Gries
    • 2
  • K. N. Slessor
    • 1
  • G. G. S. King
    • 1
  • W. W. Bowers
    • 3
  • R. J. West
    • 3
  1. 1.Department of ChemistrySimon Fraser UniversityBurnabyCanada
  2. 2.Centre for Pest Management, Department of Biological SciencesSimon Fraser UniversityBurnabyCanada
  3. 3.Newfoundland and Labrador RegionForestry CanadaSt. John'sCanada

Personalised recommendations