Identification of male-specific chiral compound from the sugarcane weevil Sphenophorus levis.
Comparative gas chromatographic analyses of airborne volatiles produced by males and females of the sugarcane weevil Sphenophorus levis, showed one male-specific compound. Gas chromatography-mass spectrometry data indicated an aliphatic alcohol that was identified as 2-methyl-4-octanol. Both optical isomers were synthesized in five steps by employing commercially available (R)- and (S)-2.2-dimethyl-1,3-dioxolane-4-methanol as starting material. Enantiomeric resolution by gas chromatography with a chiral column demonstrated that the natural alcohol possessed the S configuration. Preliminary indoor observations suggested that the alcohol elicited aggregation behavior among adults. The same compound has been previously described as an aggregation pheromone in several other curculionid species.
Departamento de Química, Universidade Federal do Paraná, Laboratório de Ecologia Química e Síntese Orgânica, CP 19081 CEP 81531-990 Curitiba-PR, Brazil. pzarbin@quimica.ufpr.br
Paulo H G
PH
Zarbin
Enrico de Beni
Ede B
Arrigoni
Aurélia
A
Reckziegel
Jardel A
JA
Moreira
Patrícia T
PT
Baraldi
Paulo C
PC
Vieira
D000818:Animals; D002849:Chromatography, Gas; D001517:Coleoptera / Q000737:chemistry*; D005260:Female; D005426:Flight, Animal; D008297:Male; D009068:Movement; D010675:Pheromones / Q000032:analysis / Q000737:chemistry*; D011157:Population Dynamics; D014835:Volatilization
D010675:Pheromones