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Chirality of macrolide pheromones of grain beetles in the generaOryzaephilusandCryptolestes and its implications for species specificity

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Abstract

The chiralities of macrolide lactone aggregation pheromones of five species of economically important grain beetles have been determined by capillary gas chromatographic separation of the diastereomeric (S)-O-acetyllactate derivatives of the hydroxy methyl esters derived from boron trifluoride-catalyzed cleavage of the macrolides in methanol. Chirally pure (Z)-3-dodecen-11-olide (I) is produced in theS configuration byCryptolestes ferrugineus (Stephens) and in theR configuration byOryzaephilus mercator (Fauvel). (Z,Z)-3,6-Dodecadien-11-olide (II) is produced in theR configuration by bothO. mercator andO. surinamensis (L.). (Z,Z)-5,8-Tetradecadien-13-olide (IV) is produced in theR configuration byO. surinamensis and as a 85∶15 mixture ofR andS isomers byC. turcicus. (Z)-5-Tetradecen-13-olide (V) is produced in the S configuration byC. pusillus (Schönherr) and as a 33∶67 mixture of theR andS isomers byC. turcicus (Grouvelle). The results indicate that in these cucujids, species specificity in pheromone response is maintained at least in part by pheromone chirality.

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Research supported by the Natural Sciences and Engineering Reseach Council of Canada, Operating Grants A3881, A0851 and A3785, and Strategic Grant G0958.

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Oehlschlager, A.C., King, G.G.S., Pierce, H.D. et al. Chirality of macrolide pheromones of grain beetles in the generaOryzaephilusandCryptolestes and its implications for species specificity. J Chem Ecol 13, 1543–1554 (1987). https://doi.org/10.1007/BF01012296

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  • DOI: https://doi.org/10.1007/BF01012296

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