Insect pheromones and their analogues XLVIII. A convenient synthesis of the 10E,12Z- and 10E,12E- isomers of hexadecadien-1-ol and of hexadeca-10E,12Z-dienal — Components of the sex pheromone of the silkworm moth

1993 ◽  
Vol 29 (5) ◽  
pp. 668-673
Author(s):  
V. N. Odinokov ◽  
G. Yu. Ishmuratov ◽  
I. M. Ladenkova ◽  
O. V. Sokol'skaya ◽  
R. R. Muslukhov ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Insect Pheromones ◽  
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.

scholarly journals Latest Developments in Insect Sex Pheromone Research and Its Application in Agricultural Pest Management

Insects ◽  
2021 ◽  
Vol 12 (6) ◽  
pp. 484
Author(s):  
Syed Arif Hussain Rizvi ◽  
Justin George ◽  
Gadi V. P. Reddy ◽  
Xinnian Zeng ◽  
Angel Guerrero
Keyword(s):  
Sex Pheromone ◽  
Pest Management ◽  
Interdisciplinary Approach ◽  
Pheromone Biosynthesis ◽  
Insect Pheromones ◽  
Agricultural Pest ◽  
Practical Applications ◽  
The Past ◽  
Significant Research ◽  
Recent Developments

Since the first identification of the silkworm moth sex pheromone in 1959, significant research has been reported on identifying and unravelling the sex pheromone mechanisms of hundreds of insect species. In the past two decades, the number of research studies on new insect pheromones, pheromone biosynthesis, mode of action, peripheral olfactory and neural mechanisms, and their practical applications in Integrated Pest Management has increased dramatically. An interdisciplinary approach that uses the advances and new techniques in analytical chemistry, chemical ecology, neurophysiology, genetics, and evolutionary and molecular biology has helped us to better understand the pheromone perception mechanisms and its practical application in agricultural pest management. In this review, we present the most recent developments in pheromone research and its application in the past two decades.

Insect pheromones and their analogues. XVI. Practical synthesis of hexadec-9Z-enal ? A component of the sex pheromone of the cotton bollwormHeliothis armigera

1987 ◽  
Vol 23 (2) ◽  
pp. 242-244
Author(s):  
V. N. Odinolov ◽  
U. M. Dzhemilev ◽  
G. Yu. Ishmuratov ◽  
L. P. Botsman ◽  
O. S. Vostrikova ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Insect Pheromones ◽  
Practical Synthesis

scholarly journals Synthetic Applications of theBaylis–Hillman Reaction: Simple and Convenient Synthesis of Five Important Insect Pheromones

2006 ◽  
Vol 89 (6) ◽  
pp. 1265-1265 ◽  
Author(s):  
Biswanath Das ◽  
Joydeep Banerjee ◽  
Nikhil Chowdhury ◽  
Anjoy Majhi ◽  
Gurram Mahender
Keyword(s):  
Insect Pheromones ◽  
Convenient Synthesis

Insect pheromones and their analogues XLIII. Chiral pheromones from (S)-(+)-3,7-dimethylocta-1,6-diene 3. Synthesis of (4R)-4-methylnonan-1-OL — Sex pheromone of Tenebrio molitor and its racemic analogue

1992 ◽  
Vol 28 (6) ◽  
pp. 618-621
Author(s):  
V. N. Odinokov ◽  
G. Yu. Ishmuratov ◽  
M. P. Yakovleva ◽  
O. V. Sokol'skaya ◽  
R. Ya. Kharisov ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Tenebrio Molitor ◽  
Insect Pheromones

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
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