Sex Attractant Pheromone from the Rice Stalk Stink Bug, Tibraca limbativentris Stal

• Published in: Journal of chemical ecology Vol. 32; no. 12; pp. 2749 - 2761
• Main Authors: Borges, M, Birkett, M, Aldrich, J.R, Oliver, J.E, Chiba, M, Murata, Y, Laumann, R.A, Barrigossi, J.A, Pickett, J.A, Moraes, M.C.B
• Format: Journal Article
• Language: English
• Published: New York, NY Springer 01.12.2006; Springer Nature B.V
• Subjects: Animal and plant ecology; Animal reproduction; Animal, plant and microbial ecology; Animals; Autoecology; Biological and medical sciences; chemical composition; chemical structure; Coleoptera - chemistry; Coleoptera - physiology; Female; Fundamental and applied biological sciences. Psychology; Gas Chromatography-Mass Spectrometry; Male; Males; Mass spectrometry; olfactometry; Oryza; Oryza sativa; Pheromones; Protozoa. Invertebrata; Sesquiterpenes; sex attractants; Sex Attractants - chemistry; sex pheromones; Stereoisomerism; stereoisomers; synthesis; Tibraca limbativentris; zingiberenol; Attractant; Sex pheromone; Chemical analysis; Pentatomidae; Insecta; Chemical structure; Male; zingiberenol; Allomone; Heteroptera; (1RS, 4RS, 1'5)-4-(1', 5'-dimethylhex-4'-enyl)- 1-methylcyclohex-2-en-1-ol; Arthropoda; Semiochemical; Invertebrata; Semiochemicals
• ISSN: 0098-0331; 1573-1561
• DOI: 10.1007/s10886-006-9197-6

The male-produced sex pheromone from the Brazilian rice stalk stink bug Tibraca limbativentris is reported. Olfactometer bioassays with sexually mature males and females showed that males attracted females, which suggests that males release a sex pheromone. Males were not attracted to either sex, nor were females attractive to conspecific females. Attraction of the females to males was highest at night. The headspace volatiles collected from male and female bugs were analyzed by gas chromatography (GC) and GC-mass spectrometry. Two male-specific compounds were identified as isomers of 1'S-zingiberenol, whereas a series of defensive compounds were identified in extracts from both sexes. Zingiberenol has three chiral centers, and the nonselective syntheses used produced two groups of isomers, zingiberenol I containing four isomers, namely (1RS,4RS,1'R)-4-(1',5'-dimethylhex-4'-enyl)-1-methylcyclohex-2-en-1-ol, and zingiberenol II containing the other four isomers, namely (1RS,4RS,1'S)-4-(1',5'-dimethylhex-4'-enyl)-1-methylcyclohex-2-en-1-ol. Both groups of stereoisomers were more attractive than hexane controls. The absolute configuration of the insect-produced pheromonal components remains to be elucidated, but the 1'S stereochemistry was established for at least one of the isomers.