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Journal of Chemical Ecology

, Volume 15, Issue 1, pp 399–411 | Cite as

Aggregation pheromone components inDrosophila mulleri

A chiral ester and an unsaturated ketone
  • Robert J. Bartelt
  • Angela M. Schaner
  • Larry L. Jackson
Article

Abstract

Existence of an aggregation pheromone was demonstrated inDrosophila mulleri. Mature males produce at least two compounds that are lacking from females and newly emerged males and that attract both males and females in a wind-tunnel bioassay. These compounds are (S)-(+)-2-tridecanol acetate and (Z)-10-heptadecen-2-one. Both were synthesized, and the flies responded to the synthetic compounds as well as to fly-derived preparations. The flies also responded to racemic 2-tridecanol acetate but not to the pureR enantiomer. A more polar, very volatile attractant was also extracted from both sexes ofD. mulleri but was not identified.

Key Words

Drosophila mulleri Diptera Drosophilidae aggregation pheromone chirality enantiomers ester ketone (S)-(+)-2-tridecanol acetate (Z)-10-heptadecen-2-one 

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References

  1. Bartelt, R.J., andJackson, L.L. 1984. Hydrocarbon component of theDrosophila virilis (Diptera: Drosophilidae) aggregation pheromone: (Z)-10-heneicosene.Ann. Entomol. Soc. Am. 77:364–371.Google Scholar
  2. Bartelt, R.J., Schaner, A.M., andJackson, L.L. 1986. Aggregation pheromones in five taxa of theDrosophila virilis species group.Physiol. Entomol. 11:367–376.Google Scholar
  3. Bartelt, R.J., Schaner, A.M., andJackson, L.L. 1988. Aggregation pheromones inDrosophila borealis andDrosophila littoralis.J. Chem. Ecol. 14:1319–1327.CrossRefGoogle Scholar
  4. Heath, R.R., andSonnet, P.E. 1980. Technique for in situ coating of Ag+ onto silica gel in HPLC columns for the separation of geometrical isomers.J. Liq. Chromatogr. 3:1129–1135.Google Scholar
  5. Miyashita, M., Yoshikoshi, A., andGrieco, P.A. 1977. Pyridiniump-toluenesulfonate: A mild and efficient catalyst for the tetrahydropyranylation of alcohols.J. Org. Chem. 42:3772–3774.CrossRefGoogle Scholar
  6. Moats, R.A., Bartelt, R.J., Jackson, L.L., andSchaner, A.M. 1987. Ester and ketone components of the aggregation pheromone ofDrosophila hydei.J. Chem. Ecol. 13:451–462.CrossRefGoogle Scholar
  7. Mori, K. 1976. Synthesis of optically active forms of ipsenol, the pheromone ofIps bark beetles.Tetrahedron 32:1101–1106.CrossRefGoogle Scholar
  8. Mori, K. 1985. Chiral synthesis: Examples in the pheromone field, pp. 293–306,in N.F. Janes (ed.). Recent Advances in the Chemistry of Insect Control. Royal Society of Chemists, London.Google Scholar
  9. Pickard, R.H., andKenyon, J. 1914. Investigations on the dependence of rotatory power on chemical constitution. Part V. The simpler esters of the carbinols CH3-CH(OH)-R.J. Chem. Soc. 105:830–898.Google Scholar
  10. Schaner, A.M., Bartelt, R.J., andJackson, L.L. 1987. (Z)-11-Octadecenyl acetate as an aggregation pheromone inDrosophila simulans.J. Chem. Ecol. 13:1777–1786.CrossRefGoogle Scholar
  11. Slessor, K.N., King, G.G.S., Miller, D.R., Winston, M.L., andCutforth, T.L. 1985. Determination of chirality of alcohol or latent alcohol semiochemicals in individual insects.J. Chem. Ecol. 11:1659–1667.CrossRefGoogle Scholar
  12. Suguro, T., andMori, K. 1979. Synthesis of optically active forms of 10-methylododecyl acetate, a minor component of the pheromone complex of the smaller tea tortrix moth.Agric. Biol. Chem. 43:869–870.Google Scholar
  13. Yates, F. 1940. The recovery of interblock information in balanced incomplete block designs.Ann. Eugen. 10:317–325.Google Scholar

Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • Robert J. Bartelt
    • 1
  • Angela M. Schaner
    • 1
  • Larry L. Jackson
    • 1
  1. 1.Department of ChemistryMontana State UniversityBozeman

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