Synthetic investigations in the field of attractive substances (sex attractants) of insects XI. Convenient synthesis of nonadec-cis-7-en-11-one and eicos-cis-7-en-11-one ? Components of the sex pheromone of Carposina niponensis

1988 ◽  
Vol 24 (1) ◽  
pp. 110-112
Author(s):  
B. G. Kovalev ◽  
A. M. Sorochinskaya ◽  
L. A. Avdeeva
Keyword(s):  
Sex Pheromone ◽  
Sex Attractants ◽  
Convenient Synthesis

Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

2017 ◽  
Vol 68 (1) ◽  
pp. 180-185
Author(s):  
Adriana Maria Andreica ◽  
Lucia Gansca ◽  
Irina Ciotlaus ◽  
Ioan Oprean
Keyword(s):  
Sex Pheromone ◽  
Coupling Reaction ◽  
Coupling Scheme ◽  
Lithium Aluminium Hydride ◽  
Terminal Alkyne ◽  
Mercury Derivative ◽  
Lithium Aluminium ◽  
Convenient Synthesis ◽  
Practical Synthesis ◽  
Insect Sex

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

A Convenient Synthesis of (Z)-6-Heneicosen-11-one — A Sex Pheromone of the Douglas-Fir Tussock Moth

1983 ◽  
Vol 13 (5) ◽  
pp. 379-385 ◽  
Author(s):  
P. Satyanarayana Reddy ◽  
A. B. Sahasrabudhe ◽  
J. S. Yadav
Keyword(s):  
Sex Pheromone ◽  
Douglas Fir ◽  
Tussock Moth ◽  
Convenient Synthesis

Field testing of synthetic attractants for male Grapholita libertina (Lepidoptera: Tortricidae)

2002 ◽  
Vol 134 (5) ◽  
pp. 657-665 ◽  
Author(s):  
N.K. Hillier ◽  
P.L. Dixon ◽  
W.D. Seabrook ◽  
D.J. Larson
Keyword(s):  
Sex Pheromone ◽  
Field Testing ◽  
Field Trials ◽  
Female Sex Pheromone ◽  
Sex Attractants ◽  
Monitoring Method ◽  
Female Sex ◽  
Naturally Occurring ◽  
Important Pest

AbstractIn an effort to develop an efficient monitoring method for the lingonberry fruitworm, Grapholita libertina Heinrich, an economically important pest of lingonberries, Vaccinium vitis-idaea L. var. minus Lodd. (Ericaceae), in Newfoundland, various known sex attractants for other species of the genus Grapholita Treitschke were evaluated for their ability to attract G. libertina moths in field trials in eastern Newfoundland. The chemicals tested were (E,E)-8,10-dodecadien-1-ol acetate (EE8,10-12:Ac), (E)-8-dodecen-1-ol acetate (E8-12:Ac), (Z)-8-dodecen-1-ol acetate (Z8-12:Ac), and (Z)-8-dodecen-1-ol (Z8-12:OH). Field trials in 1996 showed highest attraction to E8-12:Ac, with Z8-12:Ac and Z8-12:OH also being attractive. Trials in 1997 demonstrated that a blend of E8-12:Ac, Z8-12:Ac, and Z8-12:OH at a ratio of 85:10:5, respectively, was attractive to G. libertina males. All chemicals captured significantly more moths than did controls and all moths examined were males indicating these chemicals may be constituents of the naturally occurring female sex pheromone.

Convenient Synthesis of Muscalure, the Housefly Sex Pheromone

1981 ◽  
Vol 45 (7) ◽  
pp. 1723-1724 ◽  
Author(s):  
Yoshinobu Naoshima ◽  
Hiroshi Ozawa ◽  
Yasuyuki Takenami ◽  
Shoji Wakabayashi ◽  
Shûichi Hayashi
Keyword(s):  
Sex Pheromone ◽  
Convenient Synthesis

A convenient synthesis of 2,13- and 3,13-octadecadienyl acetates, sex pheromone components of the Synanthedon species

1990 ◽  
Vol 55 (9) ◽  
pp. 2270-2281 ◽  
Author(s):  
Michal Hoskovec ◽  
David Šaman ◽  
Bohumír Koutek
Keyword(s):  
Sex Pheromone ◽  
Triple Bond ◽  
Chain Elongation ◽  
Ni Catalyst ◽  
Nmr Data ◽  
Sex Pheromone Components ◽  
Convenient Synthesis ◽  
Pheromone Components ◽  
C Nmr

The sex pheromone components of several Synanthedon species, 2,13- and 3,13-octadecadienyl acetates (Ic, Id, IIc, IId), have been synthesized following the acetylenic route of chain elongation. Starting from ω-alkyn-1-ols III, the final compounds were constructed in five steps in about 30% overall yields. Transformation of triple bond containing intermediates into the corresponding (Z)- and (E)-olefins was achieved either by hydrogenation over the P2-Ni catalyst or by using a dispersion of sodium in toluene. The title pheromones were generated in more than 97% stereoisomeric purity. 1H and 13C NMR data of all derivatives are included.

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