(9Z)-9,13-Tetradecadien-11-ynal, the sex pheromone of the avocado seed moth, Stenoma catenifer

The highly unsaturated aldehyde (9Z)-9,13-tetradecadien-11-ynal and the corresponding alcohol were identified as possible sex pheromone components of the avocado seed moth, Stenoma catenifer. The aldehyde as a single component attracted more male moths than caged virgin female moths, and addition of the analogous alcohol and/or acetate decreased attraction. A stereospecific synthesis of the pheromone is described.

The terminal dienyne of the title compound constitutes the first example of a new class of lepidopteran pheromone structures.