scholarly journals Sex Pheromone of the Apple Leafminer Moth, Phyllonorycter ringoniella (MATSUMURA)(Lepidoptera : Gracillariidae) : Activity of Geometrical Isomers of Tetradecadienyl Acetates

1986 ◽  
Vol 21 (4) ◽  
pp. 578-581 ◽  
Author(s):  
Hajime SUGIE ◽  
Yoshio TAMAKI ◽  
Kenjiro KAWASAKI ◽  
Masayosi WAKOU ◽  
Tosio OKU ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Geometrical Isomers

Syntheses and NMR analyses of eight geometrical isomers of 10,12,14-hexadecatrienyl acetate, sex pheromone candidates of the mulberry pyralid.

1988 ◽  
Vol 52 (10) ◽  
pp. 2459-2468 ◽  
Author(s):  
Tetsu ANDO ◽  
Yasushi OGURA ◽  
Motoaki KOYAMA ◽  
Michiko KURANE ◽  
Masaaki UCHIYAMA ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Geometrical Isomers

Sex Pheromone of the Female Squash Vine Borer (Lepidoptera: Sesiidae)

1990 ◽  
Vol 25 (1) ◽  
pp. 64-72 ◽  
Author(s):  
J. A. Klun ◽  
M. Schwarz ◽  
B. A. Leonhardt ◽  
W. W. Cantelo
Keyword(s):  
Sex Pheromone ◽  
Binary Mixture ◽  
Trace Level ◽  
Geometrical Isomers ◽  
Physical Chemical ◽  
Melittia Cucurbitae ◽  
Natural Element ◽  
Behavioral Evidence ◽  
Squash Vine Borer ◽  
Chemical Evidence

Analysis of ovipositor extracts of the squash vine borer Melittia cucurbitae showed that a major component in the extracts was (E,Z)-2,13-octadecadien-l-ol acetate along with traces of (Z,Z)-and (Z,E)-isomers. The extracts probably also contained (E,Z)-2,13-octadecadien-l-ol, geometrical isomers of 3,13-octadecadien-l-ol acetate, (Z)-9-hexadecen-l-ol, (Z)-9-hexadecen-l-ol acetate, (Z)-11-hexadecen-l-ol acetate, hexadecan-l-ol acetate, (Z)-13-octadecen-l-ol acetate, and (Z)-13-octadecen-l-ol. Trapping tests with permutations of these compounds showed that a binary mixture of (E,Z)-2,13-octadecadien-l-ol acetate and (Z,Z)-3,13-octadecadien-l-ol acetate (99.7:0.3) was required to effectively cause capture of males. The binary mixture proved to be more effective as a lure for squash vine borer males than (E,Z)-2,13-octadecadien-l-ol acetate alone. Thus, behavioral evidence indicated that a 2,13- plus 3,13-isomeric combination of octadecadien-l-ol acetates quite likely is a natural element in the female sex pheromone of this moth. Physical chemical evidence for the 3,13 isomer in the female extracts was equivocal because its purported occurrence was at a trace level and absolute verification of the compound's structure was not possible.

Syntheses and NMR Analyses of Eight Geometrical Isomers of 10,12,14-Hexadecatrienyl Acetate, Sex Pheromone Candidates of the Mulberry Pyralid

1988 ◽  
Vol 52 (10) ◽  
pp. 2459-2468 ◽  
Author(s):  
Tetsu Ando ◽  
Yasushi Ogura ◽  
Motoaki Koyama ◽  
Michiko Kurane ◽  
Masaaki Uchiyama ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Geometrical Isomers

Synthesis of (8E,10Z)-Tetradeca-8,10-dienal, Sex Pheromone of Horse Chestnut Leafminer (Cameraria ohridella), and All Its Geometrical Isomers

2000 ◽  
Vol 65 (4) ◽  
pp. 511-523 ◽  
Author(s):  
Michal Hoskovec ◽  
David Šaman ◽  
Aleš Svatoš
Keyword(s):  
Sex Pheromone ◽  
Cross Coupling ◽  
Horse Chestnut ◽  
Coupling Reactions ◽  
Geometrical Isomers ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
Vinyl Iodides

(8E,10Z)-Tetradeca-8,10-dienal (1a), sex pheromone of the horse chestnut leafminer (Cameraria ohridella; Lepidoptera, Gracillariidae), and its geometrical isomers (1b-1d) were efficiently synthesized using tetrakis(triphenylphosphine)palladium catalyzed cross-coupling reactions of alk-1-ynes or alkenyl alanes with corresponding vinyl iodides. The stereoisomeric purity of obtained tetradecadienals 1a-1d was higher than 95% (GC). Relative electroantennographic (EAG) activities of the prepared compounds 1a-1d elicited on male antennae supported the previously published identification of the C. ohridella sex pheromone.

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