Abstract
A male-produced sex pheromone of the papaya fruit fly,Toxotrypana curvicauda Gerstaecker, was isolated from volatiles collected from air passed over calling males and was identified as 2-methyl-6-vinylpyrazine by comparative gas-liquid chromatographic and spectroscopic evidence. Synthetic 2-methyl-6-vinylpyrazine elicited typical pheromonal responses from unmated mature female flies such as walking, running, and flying in an arena bioassay; flying upwind with a zigzag flight pattern; and hovering in the pheromone plume in a wind-tunnel bioassay. These responses were similar quantitatively and qualitatively to responses to naturally occurring pheromone from calling male papaya fruit flies.
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References
Attygalle, A.B., andMorgan, E.D. 1984. Identification of trail pheromone of the antTetramorium caespitum L. (Hymenoptera: Myrmicinae).J. Chem. Ecol. 10:1453–1468.
Baker, R., Herbert, R.H., andLomer, R.A. 1982. Chemical components of the rectal gland secretions of maleDacus cucurbitae, the melon fly.Experientia 38:232.
Baker, R.,Herbert, R.H., andGrant, G.G. 1985. Isolation and identification of the sex pheromone of the Mediterranean fruit fly,Ceratitis capitata (Wied).J. Chem. Soc. Chem. Commum. 824–825.
Bondarovich, H.A., Friedel, P., Krampl, V., Renner, J.A., Shephard, F.W., andGianturco, M.A. 1967. Volatile constituents of coffee. Pyrazines and other compounds.J. Agric. Food. Chem. 15:1093–1343.
Brownlee R.G., andSilverstein, R.M. 1968. A micropreparative gas chromatograph and a modified carbon skeleton determinator.Anal. Chem. 40:2077–2079.
Goldman, I.M., Seibl, J., Flament, I., Gautschi, F., Winter, M., Willhalm, B., andStoll, M. 1967. Recherches sur les aromes. Sur l'arome de cafe, II pyrazines et pyridines.Helv. Chim. Acta 69:694–705.
Grob, K., andZürcher, F. 1976. Stripping of trace organic substances from water. Equipment and Procedures.J. Chromatogr. 117:285–294.
Kamal, M.R., Neubert, M., andLevine, R. 1962. The chemistry of pyrazine and its derivatives VII. The synthesis of vinylpyrazine and substituted vinylpyrazines.J. Org. Chem. 27:1363–1366.
Kinlin, T.E., Muralidhara, R., Pittet, A.O., Sanderson, A., andWalradt, J.P. 1972. Volatile components of roasted filberts.J. Agric. Food. Chem. 20:1021–1028.
Kovats, E. 1965. A retention index system.Adv. Chromatogr. 1:229–235.
Landolt, P.J. 1984. Reproductive maturation and premating period of the papaya fruit fly,Toxotrypana curvicauda Gerstaecker (Diptera: Tephritidae).Fla. Entomol. 67:240–244.
Landolt, P.J., Heath, R.R., andKing, J.R. 1985. Behavioral responses of female papaya fruit flies,Toxotrypana curvicauda Gerstaecker (Diptra: Tephritidae), to male-produced sex pheromones.Ann. Entomol. Soc. Am. 78:751–755.
Schram, S.B. 1980. The LDC Basic Book on Liquid Chromatography. Milton Roy Co., St. Petersburg, Florida. 114 p.
Sharp, J.L., andLandolt, P.J. 1984. Gustatory and olfactory behavior of the papaya fruit fly,Toxotrypana curvicauda Gerstaecker, (Diptera: Tephritidae) in the laboratory with notes on longevity.J. Ga. Entomol. Soc. 19:176–182.
Tumlinson, J.H., Heath, R.R., andTeal, P.E.A. 1982. Analysis of chemical communication systems in Lepidoptera, pp. 1–25,in B.A. Leonhardt and M. Beroza (eds.). Insect Pheromone Technology: Chemistry and Applications. ACS Symposium Series No. 190. American Chemical Society, Washington, D.C.
Wheeler, J.W., Avery, J., Olubajo, O., Shamim, M.T., Storm, C.B., andDuffield, R.M. 1982. Alkylpyrazines from Hymenoptera, isolation, identification and synthesis of 5-methyl-3-n-propyl-2-(1-butenyl)pyrazine fromAphaenogaster ants (Formicidae).Tetrahedron 38:1939–1948.
Wolfenbarger, D.O., andWalker, S.D. 1974. Two major pest problems of papayas.Proc. Fla. Hortic. Soc. 85:384–385.
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Chuman, T., Landolt, P.J., Heath, R.R. et al. Isolation, identification, and synthesis of male-produced sex pheromone of papaya fruit fly,Toxotrypana curvicauda Gerstaecker (Diptera: Tephritidae). J Chem Ecol 13, 1979–1992 (1987). https://doi.org/10.1007/BF01014680
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DOI: https://doi.org/10.1007/BF01014680