Queen Sex Pheromone of the Slave-making Ant, Polyergus breviceps

• Published in: Journal of chemical ecology Vol. 33; no. 5; pp. 935 - 945
• Main Authors: Greenberg, Les, Tröger, Armin G, Francke, Wittko, McElfresh, J. Steven, Topoff, Howard, Aliabadi, Ali, Millar, Jocelyn G
• Format: Journal Article
• Language: English
• Published: New York, NY New York : Springer-Verlag 01-05-2007; Springer; Springer Nature B.V
• Subjects: Animal and plant ecology; Animal, plant and microbial ecology; Animals; Ants; Ants - physiology; Autoecology; Bioassays; Biological activity; Biological and medical sciences; chemical composition; Enantiomers; ethyl-4-methylpentan-1-ol; Female; Formica; Formicidae; Fundamental and applied biological sciences. Psychology; Male; methyl 6-methylsalicylate; Nests; Pentanols - chemical synthesis; Pentanols - isolation & purification; Pentanols - pharmacology; pheromone blends; Pheromones; Polyergus; Polyergus breviceps; Protozoa. Invertebrata; queen insects; Queens; Salicylates - chemical synthesis; Salicylates - isolation & purification; Salicylates - pharmacology; Sex; sex attractants; Sex Attractants - chemical synthesis; Sex Attractants - isolation & purification; Sex Attractants - pharmacology; Sex pheromone; sex pheromones; Sexual Behavior, Animal - drug effects; social parasitism; synthesis; Workers; Workers (insect caste); Formicidae; Sex pheromone; Chemical analysis; Insecta; Polyergus breviceps, Queen sex pheromone, Methyl 6-methylsalicylate; Social insect; Formicoidea; Slave making; (R)-3-ethyl-4-methylpentan-1-ol, Ant; Queen insect; Arthropoda; Hymenoptera; Invertebrata; Aculeata; Semiochemicals
• ISSN: 0098-0331; 1573-1561
• DOI: 10.1007/s10886-007-9269-2

Workers of the slave-making ant, Polyergus breviceps, raid nests of Formica ants and return with Formica pupae that mature into worker ants in the slave-makers' colony. These Formica workers then tend the Polyergus brood, workers, and reproductives. During raids in the mating season, winged virgin Polyergus queens accompany the workers in the raiding columns. During the raid, the virgin queens release a pheromone that attracts males that quickly mate with the queens. We report the identification, synthesis, and bioassay of the sex attractant pheromone of the queens as an approximately 1:6 ratio of (R)-3-ethyl-4-methylpentan-1-ol and methyl 6-methylsalicylate. The ants produce exclusively the (R)-enantiomer of the alcohol, and the (S)-enantiomer has no biological activity, neither inhibiting nor increasing attraction to blends of methyl 6-methylsalicylate with the (R)-enantiomer.