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

ChemInform ◽  
2000 ◽  
Vol 31 (38) ◽  
pp. no-no
Author(s):  
Michal Hoskovec ◽  
David Saman ◽  
Ales Svatos
Keyword(s):  
Sex Pheromone ◽  
Horse Chestnut ◽  
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.

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

Cameraria gaultheriella and C. lobatiella attracted in Canada to (E,Z)-8,10-tetradecadienal, the sex pheromone of the European C. ohridella

2006 ◽  
Vol 138 (2) ◽  
pp. 263-268 ◽  
Author(s):  
Gábor Szöcs ◽  
Imre S. Otvos ◽  
Andrea J. Schiller ◽  
Jan Bergmann ◽  
Wittko Francke
Keyword(s):  
British Columbia ◽  
Sex Pheromone ◽  
Field Trapping ◽  
Horse Chestnut ◽  
Pheromone Traps ◽  
Quercus Garryana ◽  
Gaultheria Shallon ◽  
Sticky Traps ◽  
Oak Trees ◽  
Trapping Trials

AbstractField trapping trials showed that Cameraria gaultheriella Walsingham and C. lobatiella Opler and Davis (Lepidoptera: Gracillariidae) were attracted in significant numbers in British Columbia, Canada, to sticky traps baited with 10 µg of (E,Z)-8,10-tetradecadienal (E8Z10-14Ald), the sex pheromone of the European horse chestnut leafminer, C. ohridella Deschka and Dimic. There was perfect specificity in captures at habitats located only about 8 km apart from each other: C. gaultheriella was captured exclusively at a humid habitat covered by the shrub salal, Gaultheria shallon Pursh (Ericaceae), whereas C. lobatiella was trapped at an arid location with Garry oak trees, Quercus garryana Dougl. (Fagaceae). Seasonal flight patterns of these two Canadian Cameraria species, as monitored by pheromone traps, indicated differences in their respective flight periods. The possibility of additional cryptic components in the respective pheromones of these three Cameraria species attracted to E8Z10-14Ald is discussed.

Morphology of female sex pheromone gland in the horse chestnut leafminer Cameraria ohridella (Lep., Gracillariidae)

2003 ◽  
Vol 127 (3) ◽  
pp. 121-126 ◽  
Author(s):  
G. Raspotnig ◽  
R. Schicho ◽  
E. Stabentheiner ◽  
C. Magnes ◽  
M. Stelzl
Keyword(s):  
Sex Pheromone ◽  
Horse Chestnut ◽  
Pheromone Gland ◽  
Female Sex Pheromone ◽  
Female Sex ◽  
Sex Pheromone Gland

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.

scholarly journals Chemical communication in horse-chestnut leafminer Cameraria ohridella Deschka & Dimić.

1999 ◽  
Vol 35 (No. 1) ◽  
pp. 10-13 ◽  
Author(s):  
A. Svatoš ◽  
B. Kalinová ◽  
M. Hoskovec ◽  
J. Kindl ◽  
i. Hrdý
Keyword(s):  
Sex Pheromone ◽  
Wind Tunnel ◽  
Chemical Communication ◽  
Horse Chestnut ◽  
Active Components ◽  
Behavioural Bioassay ◽  
Hexane Extracts

Females of the horse-chestnut leafminer Cameraria ohridella Deschka & Dimić (Lepidoptera: Gracillariidae) produce a highly attractive sex pheromone in the early photophase. The pheromone, luring conspecific males into Delta traps baited with females, is produced in the female abdominal tip (ca 10–50 pg per calling female) and the active components can be extracted with hexane. Both dissected tips and their hexane extracts show high attractiveness for C. ohridella males in a wind tunnel behavioural bioassay. According to electrophysiologic recordings the male antennae are notably sensitive to both dissected female abdomens and extracts from them. The strong attractiveness of the pheromone may be useful in control of this pest. 

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

2002 ◽  
Vol 57 (7-8) ◽  
pp. 739-752 ◽  
Author(s):  
Wittko Francke ◽  
Stephan Franke ◽  
Jan Bergmann ◽  
Till Tolasch ◽  
Mitko Subchev ◽  
...  
Keyword(s):  
Population Dynamics ◽  
Biological Activity ◽  
Sex Pheromone ◽  
Field Tests ◽  
Mass Spectrometric ◽  
Horse Chestnut ◽  
Female Sex Pheromone ◽  
Synthetic Pheromone ◽  
Trap Catches ◽  
Structure Confirmation

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,10Z)-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.

Sign in / Sign up

Export Citation Format

Share Document