Female sex pheromone of Cameraria ohridella Desch. and Dim. (Lepidoptera: Gracillariidae): structure confirmation, synthesis and biological activity of (8E,10Z)-8,10-tetradecadienal and some analogues.
Mass spectrometric investigations confirmed the structure of the female produced sex pheromone of the horse-chestnut leafminer Cameraria ohridella Desch. and Dim. to be (8E,IOZ)-8,10-tetradecadienal. Pure samples, prepared in a straightforward synthesis, were highly attractive in field tests and proved to be suitable for monitoring of flight activities and population dynamics. In mixtures with the synthetic pheromone, analogues like 9-tridecynal and 7-dodecynyl formate were shown to reduce trap catches. In electroantennographic experiments, pheromone analogues were less active than the pheromone. 9-Tridecynal was the most EAG active analogue tested, followed by 7-dodecyn-1-yl formate and 7-undecyn-1-yl formate.
Francke
Wittko
W
Institute of Organic Chemistry, Hamburg University, Germany. francke@chemie.uni-hamburg.de
Franke
Stephan
S
Bergmann
Jan
J
Tolasch
Till
T
Subchev
Mitko
M
Mircheva
Albena
A
Toshova
Teodora
T
Svatos
Ales
A
Kalinová
Blanka
B
Kárpáti
Zsoltan
Z
Szöcs
Gábor
G
Tóth
Miklos
M
D000447:Aldehydes / Q000494:pharmacology*; D000818:Animals; D002849:Chromatography, Gas; D005260:Female; D008958:Models, Molecular; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects / Q000502:physiology*; D018515:Plant Leaves / Q000469:parasitology; D012724:Sex Attractants / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship
C466771:8,10-tetradecadienal; D000447:Aldehydes; D012724:Sex Attractants