20711-10-8Relevant articles and documents
Behavioral responses of Spodoptera littoralis males to sex pheromone components and virgin females in wind tunnel
Quero, Carmen,Lucas, Philippe,Renou, Michel,Guerrero, Angel
, p. 1087 - 1102 (1996)
The major component of the sex pheromone of female Spodoptera littoralis, (Z,E)-9,11-tetradecadienyl acetate (1), elicited all steps of the male behavioral sequence, i.e., wing fanning and taking flight, oriented upwind flight and arrival to the middle of the tunnel, close approach and contact with the source. The activity was equivalent to that elicited by virgin females. In the range of doses tested, the dosage of 1 had no significant effect on the number of source contacts. Male response was significantly affected by light intensity, being optimum at 3 lux. Activity of the minor components (Z)-9-tetradecenyl acetate (2), (E)-11-tetradecenyl acetate (3), tetradecyl acetate (4), (Z)-11-tetradecenyl acetate (5), and (Z,E)-9,12-tetradecadienyl acetate (6) was significantly lower than that of the major component when assayed individually. In multicomponent blends compound 4 appeared to strongly decrease the number of males arrested at the source, the effect being particularly important when compound 5 was present in the blend. Results of single sensillum experiments confirmed the existence of two main physiologically distinct sensillar types. The most common type of sensilla contained a neuron that responded specifically to compound 1. A second type of sensilla, located laterally on the ventral sensory surface, contained two receptor neurons responding to compound 6 and to (Z)-9-tetradecenol. Among short sensilla, one hair responded to compound 4 and could represent a minor sensillar type. No sensory neuron was found to detect the other minor pheromone compounds 2, 3, and 5,.
A "TUNABLE" STEREOSELECTIVE ALKENE SYNTHESIS BY IODODESILYLATION OF VINYLSILANES
Chan, T. H.,Koumaglo, K.
, p. 883 - 886 (1986)
The stereoselectivity of iododesilylation of terminal E-vinylsilanes varies with changing amount of Lewis acid.The use of this "tunable" stereoselective reaction was demonstrated by the syntheses of two insect sex pheromones with defined E/Z isomeric rations.
SYNTHESIS OF PHEROMONE DERIVATIVES VIA Z-SELECTIVE OLEFIN METATHESIS
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Paragraph 0254-0258, (2021/12/28)
Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.
SYNTHESIS OF STRAIGHT-CHAIN LEPIDOPTERAN PHEROMONES THROUGH ONE- OR TWO- CARBON HOMOLOGATION OF FATTY ALKENES
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, (2020/02/14)
Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.
SYNTHESIS OF PHEROMONES AND RELATED MATERIALS VIA OLEFIN METATHESIS
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, (2018/09/12)
Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.
Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones
Zubrytski,Kananovich,Matiushenkov
, p. 813 - 823 (2017/08/02)
Oxidative cleavage of exo- and endo-alkyl- and hydroxyalkyl-substituted bicyclo[n.1.0]alkan-1-ols with (diacetoxy-λ3-iodanyl)benzene gave the corresponding methyl alkenoates exclusively with E or Z configuration of the double bond. This reaction was used as the key stage in the syntheses of stereoisomerically pure components of pest insect pheromones: (E)-dodec-9-en-1-yl acetate (European pine shoot moth Rhyacionia buoliana), (Z)-tetradec-11-en-1-yl acetate (European oak leafroller Tortrix viridana), and (3E,8Z,11Z)-tetradeca-3,8,11-trien-1-yl acetate (tomato leafminer Tuta absoluta).
SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES
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Paragraph 0191; 0192, (2013/09/12)
The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.
Concise syntheses of insect pheromones using Z-Selective cross metathesis
Herbert, Myles B.,Marx, Vanessa M.,Pederson, Richard L.,Grubbs, Robert H.
supporting information, p. 310 - 314 (2013/02/23)
Very short synthetic routes to nine cisolefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported (see scheme). These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.
Exo- and endohormones. XXIV. 1 a convenient synthesis of (Z)-11-tetradecen-1-YL acetate, component of lepidoptera insect sex pheromone
Gansca, Lucia,Andreica, Adriana,Ciotlaus, Irina,Maxim, Sanda,Oprean, Ioan
experimental part, p. 705 - 709 (2012/04/17)
A new and practical synthesis of (Z)-11-tetradecene-1-yl acetate was developed using commercially raw material. The synthesis was based on a C 10+C2=C12 and C12+C 2=C14 coupling scheme, starting from 1,10-decane-diol. The route involves, as the key step, the use of the mercury derivative of the terminal alkyne ω-functionalised as intermediate, which is lithiated and then alkylated. The first coupling reaction took place between monosodium acetylene obtained in situ and 1-tert-butoxy-10-bromo-decane. The second coupling reaction consisted in directly lithiated of di (t-butoxy-dodec-11-yne) mercury and then alkylated with ethyl bromide obtaining 1-tert-butoxy-tetradec- 11-yne. After acetylation and stereoselective reduction in the presence of NiP-2 catalyst of 1-tertbutoxy- tetradec-11-yne gave (Z)-11-tetradecene-1-yl acetate with 99% isomeric purity.
Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates
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Page/Page column 4, (2010/05/13)
Compounds of the formula (I) wherein R2 is a branched or unbranched, saturated or ethylenically mono or di unsaturated aliphatic radical, Z is —CH2OH, —CH2OAc or —CHO, m is a whole positive integer of one or more, and Ac is an acetyl group are synthesized by a process wherein a 1-alken-3-yl alkylate, is reacted with a halo alkanol Grignard reagent.