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Electrophysiological and behavioral responses of turnip moth males, Agrotis segetum to fluorinated pheromone analogs

Wu, Wen-Qi ; Bengtsson, Marie LU ; Hansson, Bill S. ; Liljefors, Tommy ; Löfstedt, Christer LU ; Prestwich, Glenn D. ; Sun, Wei Chuan and Svensson, Mats LU (1993) In Journal of Chemical Ecology 19(1). p.143-157
Abstract

The electrophysiological and behavioral responses of male Agrotis segetum to fluorinated analogs of (Z)-5-decenyl acetate (Z5-10:OAc) were investigated. The single sensillum recordings showed that 4,4-difluoro-(Z)-5-decenyl acetate (4,4-F2), 7,7-difluoro-(Z)-5-decenyl acetate (7,7-F2), 10,10,10-trifluoro-(Z)-5-decenyl acetate (10,10,10-F3) and 7,7,8,8-tetrafluoro-(Z)-5-decenyl acetate (7,7,8,8-F4) were each 100-fold less active than the natural Z5-10 : OAc, whereas the 7,7,8,8,9,9,10,10,10-nonafluoro-(Z)-5-decenyl acetate (F9) analog was essentially inactive. A mixture of Z5-10 : OAc, Z7-12 : OAc, and Z9-14 : OAc on a filter paper dispenser was as attractive as female gland extracts when tested in a flight tunnel. With Z5-10:OAc... (More)

The electrophysiological and behavioral responses of male Agrotis segetum to fluorinated analogs of (Z)-5-decenyl acetate (Z5-10:OAc) were investigated. The single sensillum recordings showed that 4,4-difluoro-(Z)-5-decenyl acetate (4,4-F2), 7,7-difluoro-(Z)-5-decenyl acetate (7,7-F2), 10,10,10-trifluoro-(Z)-5-decenyl acetate (10,10,10-F3) and 7,7,8,8-tetrafluoro-(Z)-5-decenyl acetate (7,7,8,8-F4) were each 100-fold less active than the natural Z5-10 : OAc, whereas the 7,7,8,8,9,9,10,10,10-nonafluoro-(Z)-5-decenyl acetate (F9) analog was essentially inactive. A mixture of Z5-10 : OAc, Z7-12 : OAc, and Z9-14 : OAc on a filter paper dispenser was as attractive as female gland extracts when tested in a flight tunnel. With Z5-10:OAc omitted, the two-component mixture elicited a significantly lower male response. Four analogs, 7,7-F2, 10,10,10-F3, 7,7,8,8-F4, and F9, were added separately to the two-component mixture to replace Z5-10:OAc. The responses elicited by the mixtures containing the 7,7-F2, 10,10,10-F3, and 7,7,8,8-F4 analogs did not differ significantly from that of the natural three-component mixture and the two-component mixture, whereas the mixture containing F9 elicited a significantly lower male response, as low as the response to the two-component mixture. In a field test the mixtures containing 10,10,10-F3 and 7,7,8,8-F4 were significantly more active than the two-component mixture, but still less active than the natural three-component mixture. It appears that field tests provided greater discrimination among pheromone analogs in assessing their behavioral activity than the flight-tunnel test did. Structure-activity analyses demonstrate the importance of the lipophilic interaction between the terminal alkyl chain and the receptor site for the activity of the stimulus. The lipophobicity of the fluorinated analogs impedes a productive receptor interaction.

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organization
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Contribution to journal
publication status
published
subject
keywords
(Z)-5-decenyl acetate, Agrotis segetum, behavioral activity, electrophysiological activity, field test, flight tunnel, fluorinated analogs, Lepidoptera, lipid solubility, lipophobicity, Noctuidae, pheromone, single sensillum recording, structure-activity analysis
in
Journal of Chemical Ecology
volume
19
issue
1
pages
143 - 157
publisher
Springer
external identifiers
  • scopus:34250075447
ISSN
0098-0331
DOI
10.1007/BF00987479
project
Evolutionary mechanisms of pheromone divergence in Lepidoptera
language
English
LU publication?
yes
id
ef4d5753-1057-44d6-aa90-e18d486281c4
date added to LUP
2020-07-23 13:49:51
date last changed
2020-09-23 15:07:18
@article{ef4d5753-1057-44d6-aa90-e18d486281c4,
  abstract     = {<p>The electrophysiological and behavioral responses of male Agrotis segetum to fluorinated analogs of (Z)-5-decenyl acetate (Z5-10:OAc) were investigated. The single sensillum recordings showed that 4,4-difluoro-(Z)-5-decenyl acetate (4,4-F2), 7,7-difluoro-(Z)-5-decenyl acetate (7,7-F2), 10,10,10-trifluoro-(Z)-5-decenyl acetate (10,10,10-F3) and 7,7,8,8-tetrafluoro-(Z)-5-decenyl acetate (7,7,8,8-F4) were each 100-fold less active than the natural Z5-10 : OAc, whereas the 7,7,8,8,9,9,10,10,10-nonafluoro-(Z)-5-decenyl acetate (F9) analog was essentially inactive. A mixture of Z5-10 : OAc, Z7-12 : OAc, and Z9-14 : OAc on a filter paper dispenser was as attractive as female gland extracts when tested in a flight tunnel. With Z5-10:OAc omitted, the two-component mixture elicited a significantly lower male response. Four analogs, 7,7-F2, 10,10,10-F3, 7,7,8,8-F4, and F9, were added separately to the two-component mixture to replace Z5-10:OAc. The responses elicited by the mixtures containing the 7,7-F2, 10,10,10-F3, and 7,7,8,8-F4 analogs did not differ significantly from that of the natural three-component mixture and the two-component mixture, whereas the mixture containing F9 elicited a significantly lower male response, as low as the response to the two-component mixture. In a field test the mixtures containing 10,10,10-F3 and 7,7,8,8-F4 were significantly more active than the two-component mixture, but still less active than the natural three-component mixture. It appears that field tests provided greater discrimination among pheromone analogs in assessing their behavioral activity than the flight-tunnel test did. Structure-activity analyses demonstrate the importance of the lipophilic interaction between the terminal alkyl chain and the receptor site for the activity of the stimulus. The lipophobicity of the fluorinated analogs impedes a productive receptor interaction.</p>},
  author       = {Wu, Wen-Qi and Bengtsson, Marie and Hansson, Bill S. and Liljefors, Tommy and Löfstedt, Christer and Prestwich, Glenn D. and Sun, Wei Chuan and Svensson, Mats},
  issn         = {0098-0331},
  language     = {eng},
  month        = {01},
  number       = {1},
  pages        = {143--157},
  publisher    = {Springer},
  series       = {Journal of Chemical Ecology},
  title        = {Electrophysiological and behavioral responses of turnip moth males, Agrotis segetum to fluorinated pheromone analogs},
  url          = {http://dx.doi.org/10.1007/BF00987479},
  doi          = {10.1007/BF00987479},
  volume       = {19},
  year         = {1993},
}