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

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 the Z,E isomer toward ma...

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Bibliographic Details
Published in:Journal of chemical ecology 1986-03, Vol.12 (3), p.619-633
Main Authors: Doolittle, R.E, Solomon, J.D
Format: Article
Language:English
Subjects:
ACETATE
ACETATES
ACETATOS
ACIDE MYRISTIQUE
ACIDO MIRISTICO
ATRAYENTES SEXUALES
ATTRACTIF SEXUEL
LEPIDOPTERA
MYRISTIC ACID
SEX ATTRACTANTS
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Summary: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 the Z,E isomer toward male P. robiniae were determined. The Z, Z isomer inhibited attraction, the E, 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 of Z3,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 of Z3,E5-14∶Ac.
ISSN:0098-0331
1573-1561
DOI:10.1007/BF01012097