Differential field responses of the little fire ant, Wasmannia auropunctata (Roger), to alarm pheromone enantiomers.

The little fire ant, Wasmannia auropunctata (Roger) (Hymenoptera: Formicidae), is an invasive ant with negative impacts on both biodiversity and agriculture throughout the tropics and subtropics. Field experiments were conducted in order to elucidate the relative attractiveness of the enantiomers of the alarm pheromones, 2,5-dimethyl-3-(2-methylbutyl)pyrazine and 3-methyl-2-(2-methylbutyl)pyrazine. The enantiomers tested were synthesized from commercially available (S)-2-methylbutan-1-ol or kinetically resolved (R)-2-methylbutan-1-ol, prepared using Pseudomonas cepacia lipase (PCL). Bioassays conducted in a macadamia orchard on the island of Hawaii demonstrated that W. auropunctata were preferentially attracted to the (S)-enantiomers of both alkyl pyrazines over the racemic mixtures in all experiments. To our knowledge, this is the first instance of differential attraction of ants to the enantiomers of chiral pyrazine pheromones despite many examples of these compounds in the literature. In addition, using a chiral column it was determined that (S)-2,5-dimethyl-3-(2-methylbutyl)pyrazine and (S)-3-methyl-2-(2-methylbutyl)pyrazine are the only enantiomers produced by W. auropunctata.