Pheromone-dependent species recognition mechanisms betweenNeodiprion pinetum andDiprion similis on white pine

Abstract

The sex pheromones ofNeodiprion pinetum (Norton) andDiprion similis (Hartig) consist of two isomers, 2S,3S,7S and 2S,3R,7R, in either the acetate orpropionate forms of 3,7-dimethylpentadecan-2-ol, respectively. The 2S,3S,7S acetate isomer is utilized byN. pinetum as the major pheromone component and the 2S,3R,7R acetate as a Synergist. ConverselyD. similis utilizes 2S,3R,7R as propionate the major pheromone component and 2S,3S,7S propionate as a Synergist. This was confirmed in the field in both Michigan and Wisconsin. Capillary gas-liquid chromatographie analyses revealed that these two isomers are present in the natural pheromones of both species at the ratios close to those predicted by artificial blending of the two optical isomers.

Field response of the pine sawfly Neodiprion sertifer to the pheromone (2S, 3S, 7S)‐diprionyl acetate and its stereoisomers

“…sertifer and other North American diprionids has been extensively studied by Coppel and coworkers (e.g. Coppel et al, 1960;Jewett et al, 1976;Olaifa et al, 1987Olaifa et al, , 1988. In all species studied so far, the acetate or propionate of 3,7-dimethyl-2pentadecanol (diprionol) is the main component of the female produced sex pheromone.…”

Synthesis of the Insect Pheromone (2S,3S,7RS)-Diprionyl Acetate by Diastereoselective Protonation

“…Thus, the absolute and relative configuration at C-2 and C-3 is highly important for the biological activity whereas the configuration at C-7 is of little relevance. [4] (S,S,S)-3,7-Dimethyl-2-pentadecanyl acetate is also the most active isomer of Neodiprion namulus namulus, N. lecontei and N. pinetum; [5] in contrast, (2S,3R,7R)-diprionyl propionate was identified as most active pheromone of Diprion similis. [6] Due to the strong dependence of the pheromone activity on the absolute and relative configuration, the stereoselective synthesis of diprionyl acetate is of great interest and should allow its use as a pest control agent in pheromone traps.…”

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

“…7 ) In the case of D. similis, (2S,3S,7R)-t as well as (2S,3S,7S)-1 functioned as a synergist. 9) To clarify the role of the methyl group at the 7-position of 1 in the pheromone activity, compounds without a 7 -position methyl group, (2S,3S)-and (2S,3R)-2-methylpentadecan-2-01 (2), were prepared and their acetates (2A) were evaluated by a field bioassay with N. sertifer in Japan.…”