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Synthesis and Biological Activity of Point ‐ Fluorinated Pheromone Analogues of Eldana saccharina
Author(s) -
Itoh Toshiyuki,
Kudo Kazutoshi,
Yokota Kazuhisa,
Tanaka Naoko,
Hayase Shuichi,
Renou Michel
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300541
Subject(s) - chemistry , pheromone , fluorine , stereochemistry , sex pheromone , optically active , biological activity , organic chemistry , botany , biochemistry , in vitro , biology
Substitution of fluorine atoms on an organic molecule makes it possible to modify the molecular orbital and electron density of the surface without changing its molecular shape. Point‐fluorinated analogues of the sex pheromone of the male African sugarcane borer were synthesized in optically active forms and their pheromone activities were investigated using an EAG test. The EAG activity of these point‐fluorinated pheromone analogues indicates that the point of fluorination has a critical influence on the pheromone activity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)