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Syntheses, Characterizations, and Biological Activities of Tetradeca‐4,8‐dien‐1‐yl Acetates as Sex Attractants of Leaf‐Mining Moth of the Genus Phyllonorycter (Lepidoptera: Gracillariidae)
Author(s) -
Liblikas Ilme,
Mozūraitis Raimondas,
Santangelo Ellen M.,
Noreika Remigijus,
BorgKarlson AnnaKarin
Publication year - 2009
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200800210
Subject(s) - chemistry , stereochemistry , sex pheromone , botany , biology
The four possible isomers of tetradeca‐4,8‐dien‐1‐yl acetate and corresponding alcohols were synthesized stereoselectively by synthetic routes employing Wittig coupling reaction for the preparation of ( Z , E )‐ and ( Z , Z )‐isomers, and alkylation of terminal alkynes for the preparation of ( E , E )‐ and ( E , Z )‐isomers as the key steps. Synthetic products were characterized by 13 C‐ and 1 H‐NMR spectroscopy as well as mass‐spectrometric methods. All four isomers gave distinctive mass spectra where m / z 81 fragments clearly dominated. Elution order, followed by retention index presented in parenthesis, of tetradeca‐4,8‐dien‐1‐ols was determined as ( Z , Z ) (2082.1), ( Z , E ) (2082.8), ( E , E ) (2083.1), and ( E , Z ) (2083.2) from unpolar SPB‐1 column, and as ( E , E ) (2210.2), ( Z , E ) (2222.1), ( E , Z ) (2223.4), and ( Z , Z ) (2224.7) from polar DB‐WAX column. The isomers of tetradeca‐4,8‐dien‐1‐yl acetates eluted in the order of ( Z , Z ) (2176.1), ( Z , E ) (2178.4), ( E , Z ) (2185.9), and ( E , E ) (2186.4) from SPB‐1 , and ( Z , E ) (2124.3), ( E , E ) (2157.7), ( Z , Z ) (2128.9), and ( E , Z ) (2135.9) from DB‐WAX columns. Field‐screening tests for attractiveness of tetradeca‐4,8‐dien‐1‐yl acetates revealed that (4 Z ,8 E )‐tetradeca‐4,8‐dien‐1‐yl acetate significantly attracted Phyllonorycter coryli and Chrysoesthia drurella males. (4 E ,8 E )‐Tetradeca‐4,8‐dien‐1‐yl acetate was the most efficient attractant for Ph. esperella and Ph. saportella males, and (4 E ,8 Z )‐tetradeca‐4,8‐dien‐1‐yl acetate was attractive to Ph. cerasicolella males.