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Science 16 May 1975:
Vol. 188. no. 4189, pp. 734 - 736
DOI: 10.1126/science.1124395
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Articles

Science, Vol 188, Issue 4189, 734-736
Copyright © 1975 by American Association for the Advancement of Science

articles

Polyzonimine: A novel terpenoid insect repellent produced by a milliped

J Smolanoff, AF Kluge, J Meinwald, A McPhail, Hicks K Miller RW, and T Eisner

A nitrogen-containing terpene 6,6-dimethyl-2-azaspiro[4.4]non-1-ene (polyzonimine) was isolated from the defensive secretion of the milliped Polyzonium rosalbum. Polyzonimine, which is repellent to such natural enemies of the milliped as ants, acts as a topical irritant to insects (10-4 M induces scratching in cockroaches). Its structure was confirmed by a five-step synthesis starting from 2,2-dimethyl-7-oxabicyclo[4.1.0]heptane.


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
Convergent evolution of chemical defense in poison frogs and arthropod prey between Madagascar and the Neotropics.
V. C. Clark, C. J. Raxworthy, V. Rakotomalala, P. Sierwald, and B. L. Fisher (2005)
PNAS 102, 11617-11622
   Abstract »    Full Text »    PDF »
Bioactive alkaloids of frog skin: Combinatorial bioprospecting reveals that pumiliotoxins have an arthropod source.
J. W. Daly, T. Kaneko, J. Wilham, H. M. Garraffo, T. F. Spande, A. Espinosa, and M. A. Donnelly (2002)
PNAS 99, 13996-14001
   Abstract »    Full Text »    PDF »


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Science. ISSN 0036-8075 (print), 1095-9203 (online)