Abstract
An alarm pheromone, C15H24, was isolated from the spotted alfalfa aphid,Therioaphis maculata. The IR, PMR, and [13C]NMR data showed that this alarm pheromone is germacrene A (structure IIIa). The negative plain curve in the ORD of the alarm pheromone implies that the pheromone is (−)-germacrene A (structure IIIb).
Similar content being viewed by others
References
Bowers, W.S., Nault, L.R., Webb, R.E.,andDutky, S.R. 1972. Aphid alarm pheromone: Isolation, identification, synthesis.Science 177:1121–1122.
Bowers, W.S.,Nishino, C.,Montgomery, M.E.,Nault, L.R., andNielson, M.W. 1977. Sesquiterpene progenitor, germacrene A: An alarm pheromone in aphids.Science In press.
Dixon, A.F.G. 1958. Escape responses shown by certain aphids to the presence of the coccinellidAdalia decempunctata (L.).Trans. R. Entomol. Soc. London 110:319–334.
DixoN, A.F.G., andStewart, W.A. 1975. Function of the siphunculi in aphids with particular reference to the sycamore aphid,Drepanosiphum platanoides.J. Zool. London 175:279–289.
Edwards, L.J., Siddall, J.B., Dunham, L.L., Uden, P., andKislow, C.J. 1973.trans-β- Farnesene, alarm pheromone of the green peach aphid.Myzus persicae (Sulzer).Nature 241:126–127.
Jautelat, M., Grutzner, J.B., andRoberts, J.D. 1970. Natural-abundance13C nuclear magnetic resonance spectra of terpenes and carotenes.Proc. Natl. Acad. Sci. U.S.A. 65:288–292.
Kislow, C.J., andEdwards, L.J. 1972. Repellent odour in aphids.Nature 235:108–109.
Kulkarni, G.H., Kelkar, G.R., andBhattacharyya, S.C. 1964. Terpenoids-L, transformation products of costunolide.Tetrahedron 20:1301–1315.
Morikawa, K., andHirose, Y. 1969. Germacrene C, precursor of δ-elemene.Tetrahedron Lett. 1969:1799–1801.
Nault, L.R., andBowers, W.S. 1974. Multiple alarm pheromones in aphids.Entomol. Exp. Appl. 17:455–457.
Nault, L.R., Edwards, L.J., andStyer, W.E. 1973. Aphid alarm pheromones: Secretion and reception.Environ. Entomol. 2:101–105.
Nishino, C., andBowers, W.S. 1976. The stereoisomers of 3,7,11-trimethyldodeca-2,6,10-triene.Tetrahedron. 32:2875–2877.
Nishino, C., Bowers, W.S., Montgomery, M.E., andNault, L.R. 1976a. Aphid alarm pheromone mimics: Thenor-farnesenes.Appl. Entomol. Zool. 11:340–343.
Nishino, C., Bowers, W.S., Montgomery, M.E., andNault, L.R. 1976b. Aphid alarm pheromone mimics: Sesquiterpene hydrocarbons.Agr. Biol. Chem. 40:2303–2304.
Tori, K., Horibe, I., Tamura, Y., Kuriyama, K., Tada, H., andTakeda, K. 1976. Reinvestigation of the conformation of laurenobiolide, a ten-membered ring sesquiterpene lactone by variable-temperature carbon-13 NMR spectroscopy. Evidence for the presence of four conformational isomers in solution.Tetrahedron Lett. 1976:387–390.
Washio, H., Nishino, C., andBowers, W.S. 1976. Antennal receptor response to sex pheromone mimics in the American cockroach.Nature 262:487–489.
Weinheimer, A.J., Youngblood, W.W., Washecheck, P.H., Karns, T.K.B., andCiereszko, L.S. 1970. Isolation of the elusive (−)-germacrene A from the gorgonian,Eunicea mammosa, Chemistry of coelenterales. XVIII.Tetrahedron Lett. 1970:497–500.
Wientjens, W.H.J.M., Lakwijk, A.C., andVan Der Marel, T. 1973. Alarm pheromones of grain aphids.Experientia 29:658–660.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Nishino, C., Bowers, W.S., Montgomery, M.E. et al. Alarm pheromone of the spotted alfalfa aphid,Therioaphis maculata buckton (Homoptera: Aphididae). J Chem Ecol 3, 349–357 (1977). https://doi.org/10.1007/BF00988450
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00988450