Novel Components of the Sex Pheromones Produced by Emerald Moths: Identification, Synthesis, and Field Evaluation

@article{Yamakawa2010NovelCO,
  title={Novel Components of the Sex Pheromones Produced by Emerald Moths: Identification, Synthesis, and Field Evaluation},
  author={Rei Yamakawa and Nguyen Duc Do and Masakatsu Kinjo and Yoshie Terashima and Tetsu Ando},
  journal={Journal of Chemical Ecology},
  year={2010},
  volume={37},
  pages={105-113}
}
The subfamily Geometrinae (Lepidoptera: Geometridae) includes many species called emerald moths. Based on our recent finding of novel polyenyl compounds, including a double bond at the 12-position from two geometrine species, Hemithea tritonaria and Thalassodes immissaria intaminata, (6Z,9Z,12Z)-6,9,12-trienes and (3Z,6Z,9Z,12Z)-3,6,9,12-tetraenes with a C17–C20 straight chain were synthesized and analyzed by GC-MS. The 6,9,12-trienes, which were prepared by a double Wittig reaction between two… 
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References

SHOWING 1-10 OF 27 REFERENCES
Sex attractants of geometrid and noctuid moths: Chemical characterization and field test of monoepoxides of 6,9-dienes and related compounds
TLDR
Seven dienes with straight C18–C23 chains were synthesized from linoleic acid, and a C17 chain was synthesized by hydrogenation of the corresponding 6,9-diyne prepared from propargyl alcohol, observing attraction of six geometrid species and five noctuid species for the first time.
Male pheromone of swift moth,Hepialus hecta L. (Lepidoptera: Hepialidae)
TLDR
Electrophysiological and behavioral experiments with natural material and synthetic samples clearly showed the three heterocyclic compounds to act as pheromones.
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.
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.
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.
Sex pheromone of the saltmarsh caterpillar moth,Estigmene acrea
TLDR
Three compounds have been identified as components of the sex pheromone emitted by females of the saltmarsh caterpillar moth, Estigmene acrea, and there is evidence that the antennal acceptor site for III is chiral.
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.
Sex pheromone components of fall cankerworm moth,Alsophila pometaria
TLDR
Flight-tunnel bioassays and field-trapping experiments confirmed that the two tetraenes together with (Z,Z, Z)-3,6,9-nonadecatriene are sex pheromone components.
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