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Sex-specific activity of (R)-(−)- and (S)- (+)-1,7-dioxaspiro[5.5]undecane, the major pheromone ofDacus oleae

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Abstract

1,7-Dioxaspiro[5.5]undecane (olean), the major component of the female sex attractant pheromone blend of the olive fruit flyDacus oleae (Gmelin) was shown to be released as a racemate. The response of males and females to pure (R)-(−) and (S)-(+)-enantiomers was tested under laboratory and field conditions. Males in laboratory and field tests responded only to (R)-(−)-olean, which functions as a sex attractant. Females responded only to (S)-(+)-olean in laboratory tests but not in the field. There are indications that the latter enantiomer fuctions as a short-range arrestant throughout the day and as an aphrodisiac in the process of mating.

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References

  • Baker, R., Herbert, R., Howse, P.E., Jones, O.T., Francke, W., andReith, W. 1980. Identification and synthesis of the major sex pheromones of the olive fly (Dacus oleae).J. Chem. Soc. D. 1106:52–53.

    Google Scholar 

  • Boland, W.,Ney, P.,Jaenicke, L., andGassmann, G. 1984. A closed loop stripping technique as a versatile tool for metabolic studies of volatiles, pp. 371–380,in Analysis of Volatiles. P. Schreier, (ed.).

  • Delrio, G.,Economopoulos, A.P.,Haniotakis, G., andProta, R. 1982. Comparative field studies on food, sex and visual attractants for the olive fruit fly. Proceedings International Symposium of CEC/IOBC on Fruit Flies of Economic Importance. Athens, Greece, November, 16–19, 1982, pp. 465–472.

  • DeMarzo, L., Nuzzaci, G., andSolinas, M. 1978. Studio anatomico, istologico, ultrastrutturale e fisiologico del retto ed osservazioni etologiche in relazione alla possibile produzione di feromoni sessuali nel maschio diDacus oleae Gmel.Entomologica 14:203–266.

    Google Scholar 

  • Feron, M. 1959. Attraction chimique du male deCeratitis capitata pour la femelle.C.R. Acad. Sci. Paris 248:2403–2404.

    Google Scholar 

  • Francke, W., Hermann, V., Gerken, B., Renwick, J.A.A., andVité, J.P. 1977. 2-Ethyl-1,6-dioxaspiro[4.4]nonane, principal aggregation pheromone ofPityogenes chalcographus (L.)Naturwissenschaften 64:590.

    Google Scholar 

  • Grob, K., andZurcher, F. 1976. Stripping of trace organic substances from water; equipment and procedure.J. Chromatogr. 117:285–294.

    Google Scholar 

  • Haniotakis, G.E. 1974. Sexual attraction in the olive fruit fly,Dacus oleae (Gmelin).Environ. Entomol. 3(1):82–86.

    Google Scholar 

  • Haniotakis, G.E. 1979. Pheromone studies of the olive fruit fly,Dacus oleae (Gmel.). Final Report, NATO Reasearch Grant No. 1352, 69 pp.

  • Haniotakis, G.E. 1985. Attraction ofDacus oleae flies to food and sex attractants and their combinations.Entomol. Exp. Appl. In press.

  • Haniotakis, G.H., Mazomenos, B.E., andTumlinson, J.H. 1977. A sex attractant of the olive fruit fly,Dacus oleae, and its biological activity under laboratory and field conditions.Entomol. Exp. Appl. 21:81–87.

    Google Scholar 

  • Haniotakis, G.E.,Kozyrakis, M., andHardakis, I. 1983. Applications of pheromones for the control of the olive fruit fly. Proceedings International Conference on Integrated Plant Protection. Budapest, Hungary, July 4–9, 1983. In press.

  • Mazomenos, B.E., andHaniotakis, G.E. 1981. A multicomponent female sex pher none ofDacus oleae (Gmelin). Isolation bioassay.J. Chem. Ecol. 7(2):137–144.

    Google Scholar 

  • Mazomenos, B.E., andHaniotakis, G.E. 1984. Male olive fruit fly attraction to the synthetic sex pheromone components in laboratory and field tests.J. Chem Ecol. In press.

  • Mazomenos, B.E., andPomonis, G.J. 1983. Male olive fruit fly pheromone: Isolation, identification and lab biassays. Proceedings International Symposium of CBC/IOBC on Fruit Flies of Economic Importance. Athens, Greece, November 16–19, pp. 96–103.

  • Mazomenos, B.E.,Haniotakis, G.E.Tumlinson, J.H., andRagousis, N. 1981. Isolation, identification, synthesis and bioassays ofDacus oleae pheromones. Panhellenic Congress of Agricultural Research. Kallithea, Chalkidiki, Greece, May 5–6, 1981. Abstract pp. 96–97.

  • Mori, K., Urmatsu, T., Watanabe, H., Yanagi, K., andMinobe, M. 1984. Synthesis of the enantiomers of 1,7-dioxaspiro[5.5]undecane, the components of the olive fly pheromone.Tetrahedron Lett. 25:3875–3878.

    Google Scholar 

  • Nakagawa, S., Farias, G.J., Suda, D., andChambers, D.L. 1972. Mating behavior of the Mediterranean fruit fly following excision of the antennae.J. Econ. Entomol. 66(2):583–584.

    Google Scholar 

  • Prokopy, R.J., andRoitberg, B.D. 1984. Foraging behavior of true fruit flies.Am. Sci., 72:41–49.

    Google Scholar 

  • Redlich, H., andFrancke, W. 1984. Synthesis of enantiomericaily pure 1,7-dioxaspiro[5.5] undecanes, pheromone components of the olive fly (Dacus oleae).Angew. Chem. Int. Ed. Engl. 23:519–520.

    Google Scholar 

  • Tsitsipis, J.A. 1977. An improved method for the mass rearing of the olive fruit fly,Dacus oleae (Gmel.) (Diptera: Tephritidae).Z. Angew. Entomol. 83:96–105.

    Google Scholar 

  • Van der Pers, J.N.C.,Haniotakis, G.E., andKing, B.M. 1984. Electroantennogram responses from olfactory system inDacus oleae. Entomol. Hell. In press.

  • Weber, R., andSchurig, V. 1984. Complexation gas chromatography, a valuable tool for the stereochemical analysis of pheromones.Naturwissenschaften 71:408–412.

    Google Scholar 

  • Zervas, G.A. 1982. Reproductive physiology ofDacus oleae (Gmelin) (Diptera: Tephritidae). Comparison of wild and laboratory reared flies.Geoponika 282:10–14.

    Google Scholar 

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Diptera: Tephritidae.

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Haniotakis, G., Francke, W., Mori, K. et al. Sex-specific activity of (R)-(−)- and (S)- (+)-1,7-dioxaspiro[5.5]undecane, the major pheromone ofDacus oleae . J Chem Ecol 12, 1559–1568 (1986). https://doi.org/10.1007/BF01012372

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