Stereoselective synthesis of (Z,E)-3,5-tetradecadienyl acetate: Sex attractant for carpenterworm moth,Prionoxystus robiniae (Peck) (Lepidoptera: Cossidae) and effect of isomers and monounsaturated acetates on its attractiveness

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Abstract
A new efficient stereoselective synthesis for (Z,E)-3,5-tetradecadienyl acetate (Z3,E5–14∶Ac) a potent male sex attractant for the carpenterworm,Prionoxystus robiniae (Peck), was developed. The effects of the other three isomers (Z,Z; E,Z; E,E) on the field attractiveness of theZ,E isomer toward maleP. robiniae were determined. TheZ, Z isomer inhibited attraction, theE, E isomer synergized attraction, and theE,Z isomer had no effect on attraction. Seven monounsaturated 14-carbon acetates were evaluated for their effect on the attractiveness ofZ3,E5–14∶Ac. (E)-3-Tetradecenyl acetate enhanced attraction and (Z)-9- and (E)-5-tetradecenyl acetate reduced trap captures. (Z,E)-3,5-Tetradecadien-1-ol also reduced the attractiveness ofZ3,E5–14∶Ac.