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Sex pheromone components of fall cankerworm moth,Alsophila pometaria

Synthesis and field trapping

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Abstract

(Z,Z,Z,E)-3,6,9,11-Nonadecatetraene and (Z,Z,Z,Z)-3,6,9,11-nonadecatetraene, sex pheromone components ofAlsophila pometaria, were synthesized by stereoselective Wittig reactions and found to be spectroscopically and chromatographically identical to isolated natural material. Flight-tunnel bioassays and field-trapping experiments confirmed that the two tetraenes together with (Z,Z,Z)-3,6,9-nonadecatriene are sex pheromone components. While traps baited with either tetraene individually captured conspecific males in field-trapping experiments, addition of the triene, which captured no males by itself, to either tetraene resulted in synergistic responses.

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References

  • Battiste, M.A., Strekowski, L., Vanderbjlt, D.P., Visnick, M., King, R.W., andNation, J.L. 1983. Anastrephin and epianastrephin, novel lactone components isolated from the sex pheromone blend of male Caribbean and Mexican fruit flies.Tetrahedron Lett. 24:2611–2614.

    Google Scholar 

  • Becker, D., Kimmel, T., Cyjon, R., Moore, I., Wysoki, M., Bestmann, H.J., Platz, H., Roth, K., andVostrowsky, O. 1983. (3Z,6Z,9Z)-3,6,9-Nonadecatriene-a component of the sex pheromonal system of the giant looper,Boarmia (Ascotis) selenaria Schiffer-müller (Lepidoptera: Geometridae).Tetrahedron Lett. 24:5505–5508.

    Google Scholar 

  • Bestmann, H.J., Stransky, W., andVostrowsky, O. 1976. Reactions of alkylidenetriphenyl-phosphoranes. XXXIII. Preparation of lithium salt free ylid solutions with sodium bis (trimethylsilyl) amide as base.Chem. Ber. 109:1694–1700.

    Google Scholar 

  • Brown, H.C., Mandal, A.K., andKulkarni, S.U. 1977. Hydroboration. 45. New, convenient preparations of representative borane reagents utilizing borane-methyl sulfide.J. Org. Chem. 42:1392–1398.

    Google Scholar 

  • Camps, F., Coll, J., Guerrero, A., andRiba, M. 1983. Simple and stereoselective synthesis of sex pheromone of processionary mothThaumetopoea pityocampa (Denis and Schiff).J. Chem. Ecol. 9:869–875.

    Google Scholar 

  • Conner, W.E., Eisner, T., Vander Meer, R.L., Guerrero, A., Ghiringelli, D., andMeinwald, J. 1980. Sex attractant of an arctiid moth(Utethesia ornatrix): A pulsed chemical signal.Behav. Ecol. Sociobiol. 7:55–63.

    Google Scholar 

  • Gosney, I.A., andRowley, A.G. 1979. Pages 17–153,in J.I.G. Cadogan (ed.). Organophos-phorus Reagents in Organic Synthesis. Academic Press, London.

    Google Scholar 

  • Heath, R.R., Tumlinson, J.H., Leppla, N.C., McLaughlin, J.R., Dueben, B., Dundulis, E., andGuy, R.H. 1983. Identification of a sex pheromone produced by female velvetbean caterpillar moth.J. Chem. Ecol. 9:645–656.

    Google Scholar 

  • Hooz, J., andGilani, S.S.H. 1968. A rapid, mild procedure for the preparation of alkyl chlorides and bromides.Can. J. Chem. 46:86–87.

    Google Scholar 

  • Kajiwara, T., Odake, Y., andHatanaka, A. 1975. Synthesis of 3Z-nonenal and 3Z.6Z-nonadienal.Agr. Biol. Chem. 39:1617–1621.

    Google Scholar 

  • Merritt, M.V., andBronson, G.E. 1977. High-performance liquid chromatography ofp- nitrophenacyl esters of selected prostaglandins on silver ion-loaded microparticulate cation-exchange resin.Anal. Biochem. 80:392–400.

    Google Scholar 

  • Palaniswamy, P., Underbill, E.W., Steck, W.F., andChisholm, M.D. 1983. Responses of male red backed cutworm,Euxoa ochrogaster(Lepidoptera: Noctuidae) to sex pheromone components in a flight tunnel.Environ. Entomol. 12:748–752.

    Google Scholar 

  • Parham, W.E., andAnderson, E.L. 1948. The protection of hydroxyl groups.J. Am. Chem. Soc. 70:4187–4189.

    Google Scholar 

  • Schneider, J.C. 1980. The role of parthenogenesis and female aptery in microgeographic, ecological adaptation in the fall cankerworm,Alsophila pometaria Harris (Lepidoptera: Geometridae).Ecology 61:1082–1090.

    Google Scholar 

  • Sendega, R.V., Prib, O.Z., andVizgert, R.V.. 1968. Synthesis and alkylating properties of some unsaturated esters of arene sulfonic acids.Zh. Org. Khim. 4:1907–1909.

    Google Scholar 

  • Steck, W., andBailey, B.K. 1978. Pheromone traps for moths: Evaluation of cone trap designs and design parameters.Environ. Entomol. 7:449–455.

    Google Scholar 

  • Still, W.C., Kahn, M., andMitra, A. 1978. Rapid Chromatographic technique for preparative separations with moderate resolution.J. Org. Chem. 43:2923–2925.

    Google Scholar 

  • Underbill, E.W., Palaniswamy, P., Abrams, S.R., Bailey, B.K., Steck, W.F., andChisholm, M.D. 1983. Triunsaturated hydrocarbons, sex pheromone components ofCaenurgina erechtea.J. Chem. Ecol. 9:1413–1423.

    Google Scholar 

  • Verkruijsse, H.D., andHasselaar, M. 1979. An improved synthesis of 1,4-diynes.Synthesis 292–293.

  • Wong, J.W., Palaniswamy, P., Underbill, E.W., Steck, W.F., andChisholm, M.D. 1984. Novel sex pheromone components from the fall cankerworm moth,Alsophila pometaria.J. Chem. Ecol. 10:463–473.

    Google Scholar 

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Lepidoptera: Geometridae.

Issued as NRCC No. 23462.

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Wong, J.W., Palaniswamy, P., Underhill, E.W. et al. Sex pheromone components of fall cankerworm moth,Alsophila pometaria . J Chem Ecol 10, 1579–1596 (1984). https://doi.org/10.1007/BF00988426

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  • DOI: https://doi.org/10.1007/BF00988426

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