Abstract
A study to identify the acidic components ofCladophora glomeata active againstAedes triseriatus larvae was extended to a mixture obtained by extracting the dried powdered alga in aqueous suspension at pH 8.5. The presence of 1,9-nonanedioic, 1,10-decanedioic, 1,11-undecanedioic and 4-ketononanoic acids was determined by GC-EIMS and GC-CIMS and confirmed by analytical coinjection GC. The presence of 5-pentyldihydro-2(3H)-furanone, a minor component, was also indicated. The group of major acidic constituents is different from those obtained by extracting driedCladophora with methanol. In contrast to the C10–C14 monocarboxylic acids, which hadLD 50 values<20 ppm againstA. triseriatus, none of the dicarboxylic acids of the series G4–C14, C16, and C22 were active; nor were 4-ketononanoic acid and 5-pentyldihydro-2(3H)-furanone active.
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References
Budzikiewicz, H., Djerassi, C., andWilliams, D.H. 1967. Mass Spectrometry of Organic. Compounds, pp. 175–176. Holden-Day, San Francisco.
Friedman, L., andLong, F.A. 1953. Mass spectra of six lactones.J. Am. Chem. Soc. 75:2832.
Hansch, C., andFuji, T. 1964. ϱ-σ-π Analysis. A method for the correlation of biological activity and chemical structure.J. Am. Chem. Soc. 86:1616.
Honkanen, E., Moisio, T., andKarvonen, P. 1965. The mass spectra of some aliphatic lactones.Acta Chem. Scand. 19:370.
LaLonde, R.T., Morris, C.D., Wong, D.F., Gardner, L.C., Eckert, D.J., King, D.R., andZimmerman, R.H. 1979. Response ofAedes triseriatus larvae to fatty acids ofCladophora.J. Chem. Ecol. 5:371–381.
McFadden, W.H., Day, E.A., andDiamond, M.J. 1965. Correlations and anomalies in mass spectra. Lactones.Anal. Chem. 37:89.
McLafferty, F.W. 1966. Interpretation of Mass Spectra. An Introduction, p. 123. W.A. Benjamin, New York.
Mills, E.L., andForney, J.L. 1977. Page 25,in J.W. Geis (ed.). Primary and Secondary Production in the St. Lawrence River. State University College of Environmental Science and Forestry, Institute of Environmental Program Affairs, Syracuse, New York.
Obrien, R.D. 1967. Insecticidal Action and Metabolism, pp. 22–31. Academic Press, New York.
Rhoades, D.F., andCates, R.G. 1976. A general theory of plant antiherbivore chemistry, page 184,in J.E. Wallace and R.L. Mansell (eds.). Recent Advances in Phytochemistry, Vol. 10. Plenum Press, New York.
Takeda, A., Takahashi, K., Torii, S., andMoriwake, T. 1966. A convenient preparation of γ-keto acids.J. Org. Chem. 31:616–618.
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Lalonde, R.T., Slayback, J.R.B., Hofstead, S.J. et al. GC-MS detected difunctional carboxylic acids released by driedCladophora at the pH of lake ontario and the st. lawrence river. J Chem Ecol 6, 27–33 (1980). https://doi.org/10.1007/BF00987524
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DOI: https://doi.org/10.1007/BF00987524