Pheromonal Production of and Response to Optically Active Epoxydienes in Some Ceometrid Moths (Lepidoptera: Geometridae)
(1994) In Zeitschrift fur Naturforschung - Section C Journal of Biosciences 49(7-8). p.516-521- Abstract
In, pheromone extracts of calling female Chiasma clathrata, L. (Lepidoptera: Geometridae), a defoliator pest of alfalfa, (Z,Z,Z)-3,6,9–heptadecatriene and (Z,Z)-6,9–cis-3,4–epoxyhepta-decadiene was identified. Chiral gas chromatography using a modified cyclodextrin and synthetic reference samples proved the natural epoxide to show (3 R.4 S)-configuration. In field trapping tests, only the pure (3/R,4S)-enantiomer of the epoxide attracted males. The addition of the triene component was synergistic. Males of the sympatric species Tephrina arenaceciria Hbn. (Lepidoptera: Geometridae) were caught only in traps with baits containing the (3S,4R)-enantiomer [together with a previously described minor component,... (More)
In, pheromone extracts of calling female Chiasma clathrata, L. (Lepidoptera: Geometridae), a defoliator pest of alfalfa, (Z,Z,Z)-3,6,9–heptadecatriene and (Z,Z)-6,9–cis-3,4–epoxyhepta-decadiene was identified. Chiral gas chromatography using a modified cyclodextrin and synthetic reference samples proved the natural epoxide to show (3 R.4 S)-configuration. In field trapping tests, only the pure (3/R,4S)-enantiomer of the epoxide attracted males. The addition of the triene component was synergistic. Males of the sympatric species Tephrina arenaceciria Hbn. (Lepidoptera: Geometridae) were caught only in traps with baits containing the (3S,4R)-enantiomer [together with a previously described minor component, (Z,Z)-3,9–cis-6,7–epoxyheptadecadiene], In trapping tests conducted iNADifferent biotope Abraxas grossu-lariata, L. (Lepidoptera: Geometridae) males were attracted by the (3S,4R)-enantiomer, whereas the (3/L4S)-enantiomer attracted a close relative. Abraxas sylvata Scop. (Lepidoptera: Geometridae). The present results suggest that one of the key mechanisms responsible for pheromone specificity among both the two alfalfa geometrids and the two Abraxas species in their respective biotops, may be the use of different enantiomers of the same polyene-derived epoxide as a sex pheromone component. It is probable that this discrimination mechanism is widespread among moth species utilizing epoxide pheromone components.
(Less)
- author
- Tóth, Miklos ; Szöcs, Gabor ; Francke, Wittko ; Schmidt, F. ; Philipp, P. ; Lofstedt, C. LU ; Hansson, Bill S. and Farag, A. I.
- organization
- publishing date
- 1994-08-01
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- (Z,Z)-69-ds-3, 4-Epoxyheptadecadiene (ZZZ)-3,6,9-Heptadecatriene, Enantiomers, Isolation, Reproductive, Sex Pheromone
- in
- Zeitschrift fur Naturforschung - Section C Journal of Biosciences
- volume
- 49
- issue
- 7-8
- pages
- 516 - 521
- publisher
- Verlag der Zeitschrift für Naturforschung
- external identifiers
-
- scopus:0028002723
- ISSN
- 0939-5075
- DOI
- 10.1515/znc-1994-7-819
- project
- Evolutionary mechanisms of pheromone divergence in Lepidoptera
- language
- English
- LU publication?
- yes
- id
- 7911d043-8053-4803-b1b3-7dbd8beac245
- date added to LUP
- 2020-05-26 16:48:37
- date last changed
- 2024-01-02 11:43:29
@article{7911d043-8053-4803-b1b3-7dbd8beac245,
abstract = {{<p>In, pheromone extracts of calling female Chiasma clathrata, L. (Lepidoptera: Geometridae), a defoliator pest of alfalfa, (Z,Z,Z)-3,6,9–heptadecatriene and (Z,Z)-6,9–cis-3,4–epoxyhepta-decadiene was identified. Chiral gas chromatography using a modified cyclodextrin and synthetic reference samples proved the natural epoxide to show (3 R.4 S)-configuration. In field trapping tests, only the pure (3/R,4S)-enantiomer of the epoxide attracted males. The addition of the triene component was synergistic. Males of the sympatric species Tephrina arenaceciria Hbn. (Lepidoptera: Geometridae) were caught only in traps with baits containing the (3S,4R)-enantiomer [together with a previously described minor component, (Z,Z)-3,9–cis-6,7–epoxyheptadecadiene], In trapping tests conducted iNADifferent biotope Abraxas grossu-lariata, L. (Lepidoptera: Geometridae) males were attracted by the (3S,4R)-enantiomer, whereas the (3/L4S)-enantiomer attracted a close relative. Abraxas sylvata Scop. (Lepidoptera: Geometridae). The present results suggest that one of the key mechanisms responsible for pheromone specificity among both the two alfalfa geometrids and the two Abraxas species in their respective biotops, may be the use of different enantiomers of the same polyene-derived epoxide as a sex pheromone component. It is probable that this discrimination mechanism is widespread among moth species utilizing epoxide pheromone components.</p>}},
author = {{Tóth, Miklos and Szöcs, Gabor and Francke, Wittko and Schmidt, F. and Philipp, P. and Lofstedt, C. and Hansson, Bill S. and Farag, A. I.}},
issn = {{0939-5075}},
keywords = {{(Z,Z)-69-ds-3; 4-Epoxyheptadecadiene (ZZZ)-3,6,9-Heptadecatriene; Enantiomers; Isolation; Reproductive; Sex Pheromone}},
language = {{eng}},
month = {{08}},
number = {{7-8}},
pages = {{516--521}},
publisher = {{Verlag der Zeitschrift für Naturforschung}},
series = {{Zeitschrift fur Naturforschung - Section C Journal of Biosciences}},
title = {{Pheromonal Production of and Response to Optically Active Epoxydienes in Some Ceometrid Moths (Lepidoptera: Geometridae)}},
url = {{http://dx.doi.org/10.1515/znc-1994-7-819}},
doi = {{10.1515/znc-1994-7-819}},
volume = {{49}},
year = {{1994}},
}