Long chain electrophilic contact poisons from the Dufour's gland of the ant Crematogasterscutellaris (Hymenoptera, Myrmicinae)

Abstract

The Dufour's gland secretion of C. scutellaris contains a series of C23 long chain derivatives characterized by the presence of a cross-conjugated dienone linked to either a primary acetate, an aldehyde, or a carboxylic acid function. These compounds further differ from each other by the degree of unsaturation and (or) the position of an isolated double bond in the carbon atom chain. A combination of spectroscopic data and chemical degradations led to structures 1a–c, 2a–c, and 5a–c for the major components of the secretion. The highly electrophilic character of these compounds accounts for their efficiency as contact poisons.