SEX-PHEROMONE OF THE OLEANDER SCALE, ASPIDIOTUS-NERII - STRUCTURAL CHARACTERIZATION AND ABSOLUTE-CONFIGURATION OF AN UNUSUAL FUNCTIONALIZEDCYCLOBUTANE

The sex pheromone emitted by the female oleander scale, Aspidiotus ner ii (Homoptera, Diaspididae), has been isolated and characterized as (1 R,2S)-cis-2-isopropenyl-1-(4'-methyl-4' -penten-1'-yl)cyclobutaneethan ol 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 possi ble stereoisomers. The absolute configuration has been determined by c omparison of the activity of the cis (1S,2R) and (1R,2S) enantiomers w ith that exhibited by the natural material in greenhouse bioassays and field tests. The structure of this sesquiterpenoid pheromone is new i n the coccids and in the pheromone field in general.