Abstract
The novel pyrazines, (E)- and (Z)-5-methyl-3-(2-methylbutyl)-2-(3-methylbut-1-enyl)pyrazine, (E)- and (Z)-5-methyl-3-isopentyl-2-(3-methylbut-1-enyl) pyrazine, (E)- and (Z)-5-methyl-3-(2-methylbutyl)-2-(3-methylpent-1-enyl)pyrazine, (E)- and (Z)-5-methyl-3-isopentyl-2-(3-methylpentl-enyl) pyrazine, together with the known pyrazines, 2,5-dimethyl-3-(2-methylbutyl)pyrazine and 2,5-dimethyl-3-isopentylpyrazine, have been identified from the head of the Australian ponerine antRhytidoponera metallica. Alkanes and alkenes, in small amounts, were also detected.
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References
Attygale, A.B., andMorgan, E.D. 1984. Chemicals from the glands of ants.Chem. Soc. Rev. 13:245–278.
Brophy, J.J., andCavill, G.W.K. 1980. Naturally occurring pyrazines and their mass spectral characterization.Heterocycles 14:477–504.
Brophy, J.J., andNelson, D. 1985. 2,5-Dimethyl-3-n-propylpyrazine from the head of the bull antMyrmecia gulosa (Fabr.)Insect Biochem. 15:363–365.
Brophy, J.J., Nelson, D., Goldsack, R.J., Lidgard, R.O., andMelley, D.P. 1979. Elemental compositions from low resolution magnetic mass spectrometers.Lab. Pract. 28:615–619.
Brophy, J.J., Cavill, G.W.K., andPlant, W.D. 1981. Volatile constituents of an Australian ponerine antRhytidoponera chalybaea.Insect Biochem. 11:307–310. (species correction,Insect Biochem. 1984. 14:738).
Brophy, J.J., Cavill, G.W.K., andDuke, R.K. 1983. Volatile constituents in a methylene chloride extract of a ponerine antRhytidoponera aciculata (Smith).Insect Biochem. 13:503–505.
Brown, W.L., Jr. 1960. The release of alarm and attack behavior in some New World army ants.Psyche 66:25–27.
Brown, W.V., andMoore, B.P. 1979. Volatile secretory products from an Australian formicine ant of the genusCalomyrmex.Insect Kochem. 9:451–460.
Casnati, G., Ricca, A., andPavan, M. 1967. Sulla secrezione difensiva glandole mandibolari diPaltothyreus tarsatus (Fabr). (Hymenoptera Formicidae).Chim. Ind. 49:57–58.
Cavill, G.W.K., andHoughton, E. 1974. Some pyrazine derivatives from the Argentine antIridomyrmex humilis.Aust. J. Chem. 27:879–889.
Crew, R.M., andFletcher, D.J.C. 1974. Ponerine ant secretions: The mandibular gland secretion ofPaltothyreus tarsatus Fabr.J. Entomol. Soc. S. Afr. 37:291–298.
Duffield, R.M., Blum, M.S., andWheeler, J.W. 1976. Alkylpyrazine alarm pheromones in primitive ants with small colonial units.Comp. Biochem. Physiol. 54B:439–440.
Fales, H.M., Blum, M.S., Bain, Z., Jones, T.S., andDon, W. 1984. Volatile compounds from ponerine ants of the genusMesoponera.J. Chem. Ecol. 10:651–665.
Herman, H.R., Blum, M.S., Wheeler, J.W., Overal, W.L., Schmidt, J.O., andChao, J.T. 1984. Comparative anatomy and chemistry of the venom apparatus and mandibular glands inDinoponera grandis (Guerin) andParaponera clavata.Ann. Entomol. Soc. Am. 77:272–279.
Howard, D.F., Blum, M.S., Jones, T.H., andTomalski, M.D. 1982. Behavioral responses to an alkylpyrazine from the mandibular gland ofWasmannia auropunctata.Insectes Soc. 29:369–374.
Klein, B., andSpoerri, P. 1951. The action of organolithium compounds on 2,5-dimethylpyrazine II.J. Am. Chem. Soc. 73:2949–2951.
Longhurst, C., Baker, R., House, P.E., andSpeed, W. 1978. Alkylpyrazines in ponerine ants: Their presence in three genera, and cast specific behavioral responses to them inOdontomachus troglodytes.J. Insect Physiol. 24:833–837.
Longhurst, C., Baker, R., andHouse, P.E. 1980. A multicomponent mandibular gland secretion in the ponerine antBothroponera soror (Emery).J. Insect Physiol. 26:551–555.
Meinwald, J., andWiemer, D.F. 1983. Pygidial gland secretions of the ponerine antRhytidoponera metallica.Naturwissenschaften 70:46–47.
Wheeler, J.W., andBlum, M.S. 1973. Alkylpyrazine alarm pheromones in ponerine ants.Science 182:501–503.
Wheeler, J.W., andBlum, M.S. 1973. Alkylpyrazine alarm pheremones in ponerine ants.Science 182:501–503.
Wheeler, J.W., Avery, J., Olubajo, O., Shamim, M.T., Storm, C.B., andDuffield, R.M. 1982. Alkyl pyrazines from Hymenoptera: Isolation, identification and synthesis of 5-methyl 3-n-propyl-2-(1-butenyl)pyrazine fromAphaenogaster ants (Formicidae).Tetrahedron 38:1939–1948.
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Tecle, B., Sun, C.M., Brophy, J.J. et al. Novel pyrazines from the head of Australian ponerine antRhytidoponera metallica . J Chem Ecol 13, 1811–1822 (1987). https://doi.org/10.1007/BF01013230
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DOI: https://doi.org/10.1007/BF01013230