The geometric isomers of methyl-2,4,6-decatrienoate, including pheromones of at least two species of stink bugs

@article{Khrimian2005TheGI,
  title={The geometric isomers of methyl-2,4,6-decatrienoate, including pheromones of at least two species of stink bugs},
  author={Ashot Khrimian},
  journal={Tetrahedron},
  year={2005},
  volume={61},
  pages={3651-3657}
}
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Improved synthesis of (3E,6Z,9Z)-1,3,6,9-nonadecatetraene, attraction inhibitor of bruce spanworm, Operophtera bruceata, to pheromone traps for monitoring winter moth, Operophtera brumata.
TLDR
Two new syntheses of the inhibitor (3E,6Z,9Z)-1,3,6,9-nonadecatetraene based on the intermediate (3Z, 6Z)-3, 6-hexadecadien-1-ol (4), which has been utilized in the synthesis of the pheromone, combine traditional acetylenic chemistry and Wittig olefination reactions.
Analysis of 2,4,6-nonatrienal geometrical isomers from male flea beetles, Epitrix hirtipennis and E. fuscula.
TLDR
The most abundant, new compound from E. hirtipennis was concluded to be (2 E,4 Z,6 Z)-2,4,6-nonatrienal, and patterns in emission and response suggest a pheromonal function.
Synergy of Aggregation Pheromone with Methyl (E,E,Z)-2,4,6-Decatrienoate in Attraction of Halyomorpha halys (Hemiptera: Pentatomidae)
TLDR
A combination of semiochemicals that is attractive season-long for detection, monitoring, and potential control of this polyphagous invasive pest of North America and Europe is identified.
Highly selective synthesis of conjugated dienoic and trienoic esters via alkyne elementometalation–Pd-catalyzed cross-coupling
TLDR
All four stereoisomers of ethyl undeca-2,4-dienoate were prepared in ≥98% isomeric purity by Pd-catalyzed alkenylation (Negishi coupling) using ethyl (E)- and (Z)-β-bromoacrylates, and the use of CsF or nBu4NF as a promoter base has now been found to give all of 7–10 in ≥ 98% selectivity.
Methyl 2,4,6-decatrienoates Attract Stink Bugs and Tachinid Parasitoids
TLDR
The first captures of adult and nymph BMSBs are reported and data verifying that the tachinid, Euclytia flava (Townsend), exploits methyl (E,Z,Z)-2,4,6-decatrienoate as a kairomone are presented, which indicates there are Heteroptera in North America in addition to Thyanta spp.
Tumor-Promoting Diterpene Esters from Latex of Euphorbia cauducifolia L.
Tumor-promoting characteristics of seven esters, 1–7, obtained from the latex of Euphorbia cauducifolia L. was appraised by carrying out NMRI mice back skin. The structures of 1–7 were elucidated by…
Field trapping of the invasive brown marmorated stink bug, Halyomorpha halys, with geometric isomers of methyl 2,4,6-decatrienoate.
TLDR
The field data suggest that the presence of the EEZ but not ZEZ isomer in the lure is essential for attraction of H. halys, and that other isomers are not antagonistic and may even be needed for maximum attraction.
The chemical volatiles (semiochemicals) produced by neotropical stink bugs (Hemiptera: Pentatomidae).
TLDR
Advances obtained on the behaviour and identification of sex and defensive compound of stink bugs from Brazilian crops and the application of this knowledge to manage the stink bugs are discussed.
Optimization of blends of synthetic sex pheromone components for attraction of the sorghum plant bug Stenotus rubrovittatus (Matsumura) (Heteroptera: Miridae)
TLDR
The attractiveness of lures impregnated with female extracts did not differ from optimized blend lures, suggesting that minor components at the amounts contained in the female extract do not strongly enhance its attractiveness.
Enhanced Response of Halyomorpha halys (Hemiptera: Pentatomidae) to Its Aggregation Pheromone with Ethyl Decatrienoate
TLDR
It is reported that an analogous trienoate, ethyl (2E,4E,6Z)-decatrienoate (EDT), enhances H. halys captures when combined with PHER and the addition of EDT to lures for attracting H. Halys to traps may further improve monitoring efficiency and management strategies for this invasive species.
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References

SHOWING 1-10 OF 26 REFERENCES
Syntheses of (Z,E)-5,7-dodecadienol and (E,Z)-10,12-hexadecadienol, lepidoptera pheromone components, via zinc reduction of enyne precursors. test of pheromone efficacy against the Siberian moth.
TLDR
If rubber septa are used as pheromone dispensers in Siberian moth traps monitoring, they should be replaced biweekly with fresh septa for optimal trap effectiveness.
Methyl (2E,4Z,6Z)-Deca-2,4,6-trienoate, a Thermally Unstable, Sex-Specific Compound from the Stink Bug Thyanta pallidovirens
(2E)-4,4-Dimethoxy-2-butenal in the Synthesis of Conjugated Dienes and Dienals
Using (2E)-4,4-dimethoxy-2-butenal as starting compound, methods were developed for synthesis of (2E,4E)- and (2E,4Z)-dimethoxyalkadienes. Deacetalization of the latter gives with high yield the…
The Wittig reaction: comments on the mechanism and application as a tool in the synthesis of conjugated dienes
Olefinierungen mit Phosphor‐Yliden, I. Mechanismus und Stereochemie der Wittig‐Reaktion
Unstabilized P ylides and their betaines added Li salts, losing most of their reactivity, and were reactivated with tert-BuOK, making thus possible the retardation or the acceleration of the Wittig…
Applications of Crotonyldiisopinocampheylboranes in Synthesis: Total Synthesis of Restrictinol.
The total synthesis of restrictinol, the hydrolysis product of the antifungal natural product restricticin, starting from commercially available methyl (S)-(+)-3-hydroxy-2-methylpropionate is…
Eine neue Synthese von Cyclohexadien‐Derivaten
Die Reaktion α,β-ungesattigter Carbonylverbindungen mit Phosphoranen vom Typ 3.14, 21, 27 oder 29 fuhrt an Stelle der zu erwartenden Trienester zu 1.3-Cyclohexadien-Derivaten (5, 9, 11, 13, 15, 17,…
Stereospecific diene synthesis using acetylene carbocupration; preparation of navel orangeworm pheromone and leukotriene analogues
Experimental conditions are described for the conversion of lithium dialkylcuprates into the corresponding doubly vinylogous 1Z,3Z-dienylcuprates using acetylene carbocupration. These dienylcuprates…
Deca-2, 4, 6-trienoic acid, a new conjugated fatty acid, isolated from the latex ofEuphorbia pulcherrima willd
From the latex ofEuphorbia pulcherrima, a new conjugated trienoic fatty acid was isolated and identified as deca-trans-2,trans-4,cis-6-trienoic acid. Four other isomers of this acid were also present…
Sex Attractant Pheromone of the Red-Shouldered Stink Bug Thyanta pallidovirens: A Pheromone Blend with Multiple Redundant Components
TLDR
Female extract was as attractive as a blend reconstructed from synthesized compounds, indicating all biologically active components had been identified, and females were attracted to synthetic pheromone lures.
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