Literature DB >> 14682506

Enantiomers of (Z,Z)-6,9-heneicosadien-11-ol: sex pheromone components of Orgyia detrita.

Regine Gries1, Grigori Khaskin, Eugene Khaskin, John L Foltz, Paul W Schaefer, Gerhard Gries.   

Abstract

(6Z,9Z,11S)-6,9-Heneicosadien-11-ol (Z6Z9-11S-ol-C21) and (6Z,9Z,11R)-6,9-heneicosadien-11-ol (Z6Z9-11R-ol-C21) were identified as major sex pheromone components of female tussock moths, Orgyia detrita Guérin-Méneville (Lepidoptera: Lymantriidae), on the basis of (1) analyses of pheromone gland extracts of female O. detrita by coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC mass spectrometry, and (2) field trapping experiments with synthetic standards. Z6Z9-11S-ol-C21 and Z6Z9-11R-ol-C21 in combination, but not singly, attracted significant numbers of male moths. Racemic Z6Z9-11-ol-C21 was more attractive than the 1:3.5 (R:S) blend ratio found in pheromone gland extracts from female moths. Lower and higher homologues of Z6Z9-11-ol-C21 were also detected in GC-EAD recordings of pheromone extracts, and the racemic compounds enhanced attractiveness of Z6Z9-11-ol-C21 in field experiments. Because of trace amounts of these homologues in extracts, their enantiomeric composition could not be determined. This is the first report of secondary alcohols as pheromone components in the ditrysian (advanced) Lepidoptera.

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Year:  2003        PMID： 14682506     DOI： 10.1023/a:1026262028172

Source DB:  PubMed          Journal:  J Chem Ecol        ISSN： 0098-0331            Impact factor:   2.626


  7 in total

1.  A GENERALIZATION OF THE RETENTION INDEX SYSTEM INCLUDING LINEAR TEMPERATURE PROGRAMMED GAS-LIQUID PARTITION CHROMATOGRAPHY.

Authors:  H VANDENDOOL; P D KRATZ
Journal:  J Chromatogr       Date:  1963-08

2.  Douglas-fir tussock moth: sex pheromone identification and synthesis.

Authors:  R G Smith; G E Daterman; G D Daves
Journal:  Science       Date:  1975-04-04       Impact factor: 47.728

3.  Identification of a novel moth sex pheromone inEriocrania cicatricella (Zett.) (Lepidoptera: Eriocraniidae) and its phylogenetic implications.

Authors:  J Zhu; M V Kozlov; P Philipp; W Francke; C Löfstedt
Journal:  J Chem Ecol       Date:  1995-01       Impact factor: 2.626

4.  Novel type of sex pheromone structure identified fromStigmella malella (Stainton) (Lepidoptera: Nepticulidae).

Authors:  M Tóth; G Szöcs; E J van Nieukerken; P Philipp; F Schmidt; W Francke
Journal:  J Chem Ecol       Date:  1995-01       Impact factor: 2.626

5.  Synthesis and field testing of enantiomers of 6Z,9Z-cis-3,4-epoxydienes as sex attractants for geometrid moths : Interactions of enantiomers and regioisomers.

Authors:  J G Millar; M Giblin; D Barton; A Morrison; E W Underhill
Journal:  J Chem Ecol       Date:  1990-07       Impact factor: 2.626

6.  Pheromone specificity inEriocrania semipurpurella (Stephens) andE. sangii (Wood) (Lepidoptera: Eriocraniidae) based on chirality of semiochemicals.

Authors:  M V Kozlov; J Zhu; P Philipp; W Francke; E L Zvereva; B S Hansson; C Löfstedt
Journal:  J Chem Ecol       Date:  1996-03       Impact factor: 2.626

7.  Pheromonal secretions from glands on the 5th abdominal sternite of hydropsychid and rhyacophilid caddisflies (Trichoptera).

Authors:  C Löfstedt; B S Hansson; E Petersson; P Valeur; A Richards
Journal:  J Chem Ecol       Date:  1994-01       Impact factor: 2.626
  7 in total
  7 in total

1.  (7E,11E)-3,5,9,11-Tetramethyltridecadienal: Sex Pheromone of the Strepsipteran Xenos peckii.

Authors:  Michael Hrabar; Huimin Zhai; Regine Gries; Paul W Schaefer; Jason Draper; Robert Britton; Gerhard Gries
Journal:  J Chem Ecol       Date:  2015-08-14       Impact factor: 2.626

2.  Populations of the gall midge Dasineura oxycoccana on cranberry and blueberry produce and respond to different sex pheromones.

Authors:  Sheila M Fitzpatrick; Regine Gries; Grigori Khaskin; Daniel A H Peach; Jessika Iwanski; Gerhard Gries
Journal:  J Chem Ecol       Date:  2013-01-08       Impact factor: 2.626

3.  Identification of sex pheromone components of the painted apple moth: a tussock moth with a thermally labile pheromone component.

Authors:  A M El-Sayed; A R Gibb; D M Suckling; B Bunn; S Fielder; D Comeskey; L A Manning; S P Foster; B D Morris; T Ando; K Mori
Journal:  J Chem Ecol       Date:  2005-03       Impact factor: 2.626

4.  (Z,Z)-6,9-Heneicosadien-11-one: major sex pheromone component of painted apple moth, Teia anartoides.

Authors:  Regine Gries; Grigori Khaskin; John Clearwater; David Hasman; Paul W Schaefer; Eugene Khaskin; Oleksandr Miroshnychenko; Gordon Hosking; Gerhard Gries
Journal:  J Chem Ecol       Date:  2005-03       Impact factor: 2.626

5.  (2S,12Z)-2-Acetoxy-12-heptadecene: major sex pheromone component of pistachio twig borer, Kermania pistaciella.

Authors:  Regine Gries; Grigori Khaskin; Hassan Daroogheh; Cafer Mart; Serpil Karadag; M Kubilay Er; Robert Britton; Gerhard Gries
Journal:  J Chem Ecol       Date:  2006-12       Impact factor: 2.626

6.  Propionates and acetates of chiral secondary alcohols: novel sex pheromone components produced by a lichen moth Barsine expressa (Arctiidae: Lithosiinae).

Authors:  Toru Fujii; Rei Yamakawa; Yoshie Terashima; Shinya Imura; Keiichi Ishigaki; Masakatsu Kinjo; Tetsu Ando
Journal:  J Chem Ecol       Date:  2012-12-19       Impact factor: 2.626

7.  Does the stereochemistry of methylated cuticular hydrocarbons contribute to mate recognition in the egg parasitoid wasp Ooencyrtus kuvanae?

Authors:  Kelly Ablard; Regine Gries; Grigori Khaskin; Paul W Schaefer; Gerhard Gries
Journal:  J Chem Ecol       Date:  2012-09-25       Impact factor: 2.626
  7 in total

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