Identification of novel inhibitors of calling and in vitro [14C]acetate incorporation by pheromone glands of Plodia interpunctella

Some octopamine agonists were found to suppress in vitro biosynthesis of the calling pheromone of the Indian meal moth, Plodia interpunctella. Isolated pheromone‐gland preparations incorporated sodium [14C]acetate at a linear rate for 3 h when incubated with the pheromone biosynthesis activating neuropeptide (PBAN). This incorporation was dependent on the dose of PBAN (up to 0.5 µM). Thin‐layer chromatography of a pheromone‐gland extract revealed quantitative incorporation of radioactivity into a product exhibiting the same mobility as (Z,E)‐9,12‐tetradecadienyl acetate, the main component of the calling pheromone of P interpunctella. Twenty‐seven octopamine agonists were initially screened using a calling behaviour bioassay of female P interpunctella. Four derivatives with activity in the nanomolar range were identified which were, in order of decreasing pheromonostatic activity: 2‐(2,6‐diethylphenylimino)thiazolidine > 2‐(2,6‐diethylphenylimino)oxazolidine > 2‐(2,6‐dimethylphenylimino)thiazolidine > 2‐(2‐ethylphenylimino)oxazolidine. These compounds also showed in vitro inhibitory activity in intracellular de novo pheromone biosynthesis. The results of the present study indicate that these derivatives could provide useful information in the characterization and differentiation of octopaminergic receptor types and subtypes. © 2001 Society of Chemical Industry