Collect. Czech. Chem. Commun. 2001, 66, 1682-1690

Chemical Characterization and Synthesis of the Major Component of the Sex Pheromone of the Sugarcane Borer Diatraea saccharalis

Aleš Svatoša,*, Blanka Kalinováa, Jiří Kindla, Jelena Kuldováa, Oldřich Hovorkaa, Ruth Rufino Do Nascimentob and Neil J. Oldhamc

a Department of Natural Products, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
b Departamento de Química, Centro de Ciencias Exatas e Naturais, Universidade Federal de Alagoas, BR 104 Norte Km 14 - Campus A. C. Simoes Tabuleiro do Martins, Maceió, AL 57072970, Brazil
c The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford OX1 3QY, U.K.


(9Z,11E)-Hexadeca-9,11-dienal (1) was identified as a major component of the sex pheromone of the sugarcane borer Diatraea saccharalis. The identification is based on mass spectral examination of the extracts prepared from calling females, derivatization experiments with 4-methyl-3,5-dihydro-1,2,4-triazole-3,5-dione (2), stereospecific synthesis of dienal 1, and gas chromatography (GC) with electroantennographic detection (GC-EAD). In GC analysis, the antennaly active component and synthetic dienal 1 show identical retention times on several GC phases. However, the behavioral activity of synthetic 1 was much weaker than that of natural extracts. This suggests that an additional component(s) might be involved in sexual communication of this species.

Keywords: Sex pheromones; Diatraea saccharalis; Isolation and identification; Conjugated dienals; Aldehydes; Dienes; Stereoselective synthesis.

References: 15 live references.