Biological activity of (3R,5S,6R)- and (3S,5R,6S)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one, a...

In a previous study we reported identification of (3R*,5S*,6R*)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one as a component of the pheromone ofMacrocentrus grandii Goidanich. The lactone was present in male and female wasps, and laboratory and field bioassays demonstrated that both sources of the lactone elicit flight initiation, upwind anemotaxis, and casting in male wasps. In the present study, the synthetic (3R,5S,6R)- and (3S,5R,6S)-lactone enantiomers (RSR andSRS, respectively) were bioassayed for biological activity. In wind tunnel studies theSRS enantiomer elicited flight initiation, upwind anemotaxis, and casting by male wasps comparable to lactone derived from male and female wasps. Flight response to theRSR enantiomer averaged 14 percent of theSRS enantiomer. No specific ratio of the stereoisomers was found more attractive than theSRS enantiomer alone. Field studies demonstrated theSRS enantiomer was active alone in attracting male wasps. When paired with (Z)-4-tridecenal (a previously identified female-derived sex pheromone), theSRS enantiomer yielded a synergistic response comparable to (Z)-4-tridecenal plus female-derived lactone.