Implication of SAR of male medfly attractants in insect olfaction.

Medfly (Ceratitis capitata) males are strongly attracted by different compounds, not described as pheromones. The best attractants reported are (+)-alpha-copaene, a sesquiterpene of natural source and (-)-ceralure-B1, a non-natural iodinated cyclohexane ester. Although their origin, atomic composition, chemical and physical properties are rather different, they show similar attraction to medflies. The question of why these compounds, act behaviorally in the same way, has been never addressed in research papers. We show here for the first time that these compounds have quite similar stereochemistry, water accessible surfaces, certain local dipole moments and, to some extent, similar octanol/water partition coefficient (log P). When seven carbons, one oxygen and one iodine belonging to (-)-ceralure-B1 are selectively chosen based on topological homology with (+)-alpha-copaene and are overlaid with nine corresponding carbons of (+)-alpha-copaene, the RMS is 0.367 A. This represents a high degree of steric resemblance. Local dipole moments and charges are similar in those regions where the molecules show topological homologies. Thus, we hypothesize that these two molecules could interact with the same male medfly's odorant receptor(s). The implications of this result in future research in insect olfaction is discussed.

Attractiveness of 79 compounds and mixtures to wild Ceratitis capitata (Diptera: Tephritidae) in field trials.

Seventy-nine volatile compounds chosen from those emitted by Mediterranean fruit fly males, fruits and food baits, were tested for their attractiveness to females of Ceratitis capitata (Wiedemann) in field trials with a wild population. To correct for density fluctuations, the results were presented as a percentage of males caught in the same type of traps baited with trimedlure, a known male attractant. The mixtures of corn steep liquor with ammonia compounds and amines were the most effective attractants for females. Other compounds exhibiting C. capitata attraction were a mixture ethyl acetate+acetic acid+ethanol for both sexes, and p-cymene, 1,3-diethylbenzene and borneol for females.