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.
Zarbin
Paulo H G
PH
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
Arrigoni
Enrico de Beni
Ede B
Reckziegel
Aurélia
A
Moreira
Jardel A
JA
Baraldi
Patrícia T
PT
Vieira
Paulo C
PC
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