Sex pheromone of the oleander scale, Aspidiotus nerii: Structural characterization and absolute configuration of an unusual functionalized cyclobutane

The sex pheromone emitted by the female oleander scale, Aspidiotus nerii (Homoptera, Diaspididae), has been isolated and characterized as (1R,2S)-cis-2-isopropenyl-1-(4′-methyl-4′-penten-1′-yl)cyclobutaneethanol acetate by using advanced MS and NMR spectroscopic methods, as well as a variety of microderivatization sequences. The structure has been confirmed by stereo- and enantioselective synthesis of the four possible stereoisomers. The absolute configuration has been determined by comparison of the activity of the cis (1S,2R) and (1R,2S) enantiomers with that exhibited by the natural material in greenhouse bioassays and field tests. The structure of this sesquiterpenoid pheromone is new in the coccids and in the pheromone field in general.