Publications [#233550] of Andrew T. McPhail

Journal Articles

  1. Smolanoff, J; Kluge, AF; Meinwald, J; McPhail, AT; Miller, RW; Hicks, K; Eisner, T, "Polyzonimine: a Novel Terpenoid Insect Repellant Produced by a Milliped", Science, 1975, 188(4189), 734-736 [doi].
    (last updated on 2026/01/21)

    Abstract:
    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.