Synthesis and Field Test of a Pheromone Mimic of the Pine Sawfly (Neodiprion sertifer)

A stereochemically pure mimic of the sex pheromone components of the pine sawfly was synthesized. Acetates of (2S,3S)- and (2S,3R)-3-methylpentadecan-2-ol were prepared, and the pheromone activity of their mixture was compared with that of a true pheromone mixture of the acetates of (2S,3S,7S)- and (2S,3R,7R)-3,7-dimethylpentadecan-2-ol. Although the potency of the true pheromone system was 50 times as high as that of the pheromone mimic, the mimic could attract a sufficient number of male sawflies in the field test.