(6Z,9Z,12Z)-6,9,12-Octadecatriene and (3Z,6Z,9Z,12Z)-3,6,9,12-icosatetraene, the novel sex pheromones produced by emerald moths

@article{Yamakawa20096Z9Z12Z6912OctadecatrieneA,
  title={(6Z,9Z,12Z)-6,9,12-Octadecatriene and (3Z,6Z,9Z,12Z)-3,6,9,12-icosatetraene, the novel sex pheromones produced by emerald moths},
  author={Rei Yamakawa and Nguyen Duc Do and Yasushi Adachi and Masakatsu Kinjo and Tetsu Ando},
  journal={Tetrahedron Letters},
  year={2009},
  volume={50},
  pages={4738-4740}
}
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11 Citations
Highly Influential Citations
1
Background Citations
3
Methods Citations
1
Results Citations
3

11 Citations

Characterization of Epoxytrienes Derived from (3Z,6Z,9Z)-1,3,6,9-Tetraenes, Sex Pheromone Components of Arctiid Moths and Related Compounds
TLDR
Since the diversity of lepidopteran species suggests that structurally related compounds of the 9,10-epoxide are also utilized as a sex pheromone components, epoxytrienes derived from (3Z,6Z,9Z)-1,3,6,9-tetraenes with a C19–C21 chain were systematically synthesized and characterized.
Characterization of posticlure and the structure-related sex pheromone candidates prepared by epoxidation of (6Z,9Z,11E)-6,9,11-trienes and (3Z,6Z,9Z,11E)-3,6,9,11-tetraenes
Abstracttrans-11,12-Epoxy-(6Z,9Z)-6,9-henicosadiene (posticlure) has been identified from a pheromone gland of the lymantriid species, Orgyia postica. Since the diversity of Lepidoptera suggests that…
GC/FT-IR Analysis of Novel 4,6,9-Triene and 2,4,6,9-Tetraene Occurring in a Female Pheromone Gland of Arctia plantaginis (Erebidae: Arctiinae)
Fifteen subspecies of the wood tiger moth, Arctia plantaginis (Lepidoptera: Erebidae: Arctiinae), have been recorded in the Northern Hemisphere. An analysis of crude pheromone extracts by GC…
Novel Components of the Sex Pheromones Produced by Emerald Moths: Identification, Synthesis, and Field Evaluation
TLDR
The field evaluation of the synthetic polyenes in a mixed forest of Tokyo revealed the following new male attractants for emerald moths: Idiochlora ussuriaria by a C17 6,9,12-triene and Jodis lactearia by a 2,3,6,9-tetraene, indicating the characteristic chemical structures of Geometrinae pheromones.
A practical synthesis of (all-Z)-eicosa-3,6,9,12-tetraene, a pheromone component isolated from emerald moths
Identification of the Female-Produced Sex Pheromone of Tischeria ekebladella, an Oak Leafmining Moth
TLDR
While the triene was present in both sexes, the tetraene was female-specific, and the latter is a new structure for a pheromone component of Lepidoptera and a novel natural product.
Identification and field and laboratory tests of the sex pheromone of Cerconota anonella Sepp. (Lepidoptera: Oecophoridae)
TLDR
The ternary mixture of Z9‐18:Ac, Z9-18:Ald and Z9•18:OH was identified as attractant to C. anonella males and can be used to detect and control populations of this insect in Annonaceae plantations.
A nine carbon homologating system for skip-conjugated polyenes.
Analyses of lepidopteran sex pheromones by mass spectrometry
MACE - An Open Access Data Repository of Mass Spectra for Chemical Ecology.
MACE is an open access collection of electron impact (EI) mass spectra for coupled gas chromatography-mass spectrometry (GC/MS) that serves as an add-on database, comprising curated spectra not…
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References

SHOWING 1-10 OF 10 REFERENCES
Synthesis and Chemical Characterization of Hydrocarbons with a 6,9,11-, 3,6,9,11-, or 1,3,6,9-Polyene System, Pheromone Candidates in Lepidoptera
TLDR
This work synthesized polyunsaturated hydrocarbons with a C17–C21 chain, which included an extra double bond to investigate further structural modifications on this theme of Lepidopteran Type II sex pheromones.
Synthesis and Characterization of 2,13- and 3,13-Octadecadienals for the Identification of the Sex Pheromone Secreted by a Clearwing Moth
TLDR
A pheromone extract of a sesiid moth was examined and it was confirmed that the octadecadienal tentatively identified by a previous GC-MS analysis did indeed have the 2E,13Z configuration, and field evaluation of four synthetic geometric isomers of the 2,13-dienal revealed specific attraction to a lure with the (2E, 13Z)-isomer as a main component.
(3Z,6Z,9Z,12Z,15Z)-Pentacosapentaene, a Key Pheromone Component of the Fir Coneworm Moth, Dioryctria abietivorella
TLDR
The sex pheromone of the fir coneworm moth consists of a blend of (3Z,6Z, 9Z,12Z,15Z)-pentacosapentaene and (9Z,11E)-tetradecadienyl acetate, which may represent an important and widespread new phersomone blend motif within the Lepidoptera.
Hydrocarbons with a homoconjugated polyene system and their monoepoxy derivatives: Sex attractants of geometrid and noctuid moths distributed in Japan
TLDR
It was concluded that hydrocarbons with a homoconjugated polyene system and the monoepoxy derivatives are important components of sex pheromones produced by Japanese lepidopterous insects, particularly the geometrid moths.
Highly Efficient One‐Pot Double‐Wittig Approach to Unsymmetrical (1Z,4Z,7Z)‐Homoconjugated Trienes
We describe a novel one-pot double-Wittig approach towards unsymmetrically substituted skipped trienes using the symmetrical (Z)-hex-3-ene-1,6-bis(triphenylphosphonium iodide) (2) as key reagent.…
Unusual pheromone chemistry in the navel orangeworm: novel sex attractants and a behavioral antagonist
TLDR
The navel orangeworm sex pheromone is also an attractant for the meal moth, Pyralis farinalis L. (Pyralidae), but (Z,Z)-11,13-hexadecadien-1-yl acetate is a behavioral antagonist, which may be highly effective in mating disruption and monitoring programs.
Polyene hydrocarbons and epoxides: a second major class of lepidopteran sex attractant pheromones.
  • J. Millar
  • Biology
    Annual review of entomology
  • 2000
TLDR
Pheromone blends are created from components with different chain lengths, numbers of double bonds, and functional groups, or from mixtures of epoxide regioisomers or enantiomer, with several examples of synergism between enantiomers.
Mating Communication Systems of Four Plusiinae Species Distributed in Japan: Identification of the Sex Pheromones and Field Evaluation
TLDR
The sex pheromones of four Plusiinae species in the family Noctuidae, Ctenoplusia albostriata (CA), Macdunnoughia purissima (MP), Syngrapha ain (SA), and Diachrysia stenochrysis (DS) were identified by GC-EAD and GC-MS analyses and a classification is proposed.
Lepidopteran sex pheromones.
TLDR
This chapter deals with current methods for the identification of sex pheromones of Lepidoptera, and an actual application of the synthetic peromones for pest control is briefly introduced.
Determination of double bond position in mono-unsaturated acetates by mass spectrometry of dimethyl disulfide adducts