(2S,12Z)-2-Acetoxy-12-heptadecene: Major Sex Pheromone Component of Pistachio Twig Borer, Kermania pistaciella

Gries, Regine; Khaskin, Grigori; Daroogheh, H.; Mart, Cafer; Karadağ, S.; Er, Mehmet Kubilay; Britton, Robert; Gries, Gerhard

doi:10.1007/s10886-006-9190-0

Cited by 14 publications

(11 citation statements)

References 22 publications

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“…(Z)-2-Butyroxy-8-heptadecene was synthesized and found to have identical RIs and mass spectra to those of the major EAG-active compound in volatiles from female R. longicauda. The RIs were different from those of the corresponding E-isomer, present as an impurity in the Zisomer, and those of (Z)-2-butyroxy-12-heptadecene, derived from (Z)-2-acetoxy-12-heptadecene, the pheromone of the pistachio twig borer, Kermania pistaciella (Gries et al 2006) (Table 1).…”

Section: Resultsmentioning

confidence: 95%

“…2-Butyroxyheptadecane was prepared from 2-heptadecanone synthesized previously at NRI by addition of methyl lithium to hexadecanoic acid in ether (Jorgenson 1970 (2S,12Z)-2-Acetoxy-12-heptadecene, the pheromone of the pistachio twig borer, Kermania pistaciella (Gries et al 2006), was kindly provided by Professor Gerhard Gries. A sample was hydrolyzed with potassium carbonate in methanol to give (2S,12Z)-8-heptadecen-2-ol, and this was reacted with butyryl chloride and pyridine in dichloromethane to give a sample of (2S,12Z)-2-butyroxy-12-heptadecene.…”

Section: Micro-analytical Reactionsmentioning

confidence: 99%

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(2S,8Z)-2-Butyroxy-8-heptadecene: Major Component of the Sex Pheromone of Chrysanthemum Gall Midge, Rhopalomyia longicauda

et al. 2009

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The sex pheromone of the chrysanthemum gall midge, Rhopalomyia longicauda (Diptera: Cecidomyiidae), the most important insect pest in commercial plantations of chrysanthemum, Dendranthema morifolium (Ramat.) Tzvel., in China, was identified, synthesized, and field-tested. Volatile chemicals from virgin females and males were collected on Porapak in China and sent to the United Kingdom for analysis. Coupled gas chromatographic-electroantennographic detection (GC-EAG) analysis of volatile collections from females revealed two compounds that elicited responses from antennae of males. These compounds were not present in collections from males. The major EAG-active compound was identified as 2-butyroxy-8-heptadecene by gas chromatographic (GC) retention indices, mass spectra, in both electron impact and chemical ionization modes, hydrogenation, epoxidation, and derivatization with dimethyldisulfide. The lesser EAG-active compound was identified as the corresponding alcohol. The ratio of butyrate to alcohol in the collections was 1:0.26. Racemic (Z)-8-heptadecen-2-ol and the corresponding butyrate ester were synthesized from (Z)-7-hexadecenyl acetate, and the synthetic compounds found to have identical GC retention indices and mass spectra to those of the natural, female-specific components. Analysis of the volatile collections on an enantioselective cyclodextrin GC column showed the natural pheromone contained (2S,8Z)-2-butyroxy-8-heptadecene. Field tests showed that rubber septa containing racemic (Z)-2-butyroxy-8-heptadecene were attractive to R. longicauda males. The (naturally occurring) S-enantiomer was equally as attractive as the racemate, while the R-enantiomer was not attractive to males, and did not inhibit the activity of the S-enantiomer. The attractiveness of the butyrate was significantly reduced by the presence of even small amounts of the corresponding alcohol.

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Section: Resultsmentioning

confidence: 95%

Section: Micro-analytical Reactionsmentioning

confidence: 99%

(2S,8Z)-2-Butyroxy-8-heptadecene: Major Component of the Sex Pheromone of Chrysanthemum Gall Midge, Rhopalomyia longicauda

et al. 2009

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“…It is of interest to note that D. gleditchiae produces the (R)-enantiomer, whereas the (S)-enantiomer has so far been found more commonly in other midge species, and even in a moth species, Kermania pistaciella Ams. (Lepidoptera: Oinophilidae) (Gries et al 2006). …”

Section: Discussionmentioning

confidence: 99%

“…(2S,12Z)-2-Acetoxy-12-heptadecene, the pheromone of the pistachio twig borer, Kermania pistaciella (Gries et al 2006), was kindly provided by Prof. Gerhard Gries.…”

Section: Methodsmentioning

confidence: 99%

“…4; retention times (S)-19.74 min, (R)-20.15 min). The individual enantiomers were prepared in high enantiomeric excess by kinetic resolution with the lipase from Candida antarctica, which selectively hydrolyses or acetylates the (R)-enantiomer (e.g., Xiao and Kitazume 1997;Gries et al 2006). Analysis of a collection of volatiles from female D. gleditchiae showed a peak at the retention time of the (R)-enantiomer and essentially none (< 1%) of the (S)-enantiomer.…”

Section: Electrophysiological Analysis Of Collected Volatilesmentioning

confidence: 99%

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Identification of Female-produced Sex Pheromone of the Honey Locust Gall Midge, Dasineura gleditchiae

et al. 2009

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The honey locust gall midge, Dasineura gleditchiae Osten Sacken 1866 (Diptera: Cecidomyiidae) is the main pest of ornamental varieties of the honey locust tree, Gleditsia triacanthos L., in North America, and is now becoming a pest of concern in Europe. Female midges were observed to emerge in the early morning with their ovipositor extended until they mated. Volatiles were collected from virgin females in a closed-loop stripping apparatus and analyzed by gas chromatography (GC) coupled to electroantennographic (EAG) recording from the antenna of a male midge. A single EAG response was observed, which was assumed to be to the major component of the female sex pheromone. This was identified as (Z)-2-acetoxy-8-heptadecene by comparison of its mass spectrum and GC retention times on different columns with those of synthetic standards and by micro-analytical reactions. This compound was synthesized, and the individual enantiomers were produced by kinetic resolution with lipase from Candida antarctica. Analysis of the naturally-produced compound on a cyclodextrin GC column indicated it was the (R)-enantiomer. In EAG dose-response measurements, the (R)-enantiomer alone or in the racemic mixture evoked significant responses from the antennae of male D. gleditchiae, whereas the (S)-enantiomer did not. In field trapping tests, the (R)-enantiomer attracted male D. gleditchiae. The racemic compound was equally attractive, but the (S)-enantiomer was not attractive. Both the pure (R)-enantiomer or racemic (Z)-2-acetoxy-8-heptadecene, applied to red rubber septa in a dose range of 3-30 microg, constitute a strongly attractive bait in sticky traps for monitoring the flight of D. gleditchiae.

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(S)-2-Acetoxy-5-Undecanone, Female Sex Pheromone of the Raspberry Cane Midge, Resseliella theobaldi (Barnes)

et al. 2009

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The raspberry cane midge, Resseliella theobaldi, is a widespread pest of cultivated red raspberry in Europe. Pheromone-baited traps could provide a much-needed, accurate means to monitor the pest. Volatiles collected separately from virgin female and male midges were analyzed by gas chromatography (GC) coupled to mass spectrometry (MS) to reveal four female-specific components. In analyses by GC coupled to electroantennographic (EAG) recording from the antennae of a male midge, at least three of these components elicited responses. Based on its GC retention indices and mass spectrum, we propose that the major component is 2-acetoxy-5-undecanone and confirm this by synthesis of the racemic compound in seven steps and 63% yield from 4-pentenoic acid. The three minor components were each present at approximately 30% of the major component and were identified as 2-undecanone, (S)-2-acetoxyundecane, and (S)-2-undecanol by comparison of GC retention times and mass spectra with those of synthetic standards. GC analyses of the female-produced volatiles on an enantioselective column showed that only one enantiomer of 2-acetoxy-5-undecanone was present, and this was found to be the S-enantiomer by hydrolytic kinetic resolution of an epoxide intermediate in the synthesis and also by enantioselective hydrolysis of the racemic acetate with a lipase enzyme. The two enantiomers were also separated by high-performance liquid chromatography on an enantioselective column for field tests. In two field trapping tests, (S)-2-acetoxy-5-undecanone was highly attractive to male R. theobaldi; the R-enantiomer was not attractive. The racemic compound was just as attractive as the S-enantiomer, and addition of the three minor components in racemic form at two different loads did not affect catches. The pheromone could be dispensed from both rubber septa and polyethylene vials for at least 1 month under field conditions, but the former was preferred as it gave more uniform release. 2-Acetoxy-5-undecanone belongs to a new group of pheromone structures in the Cecidomyiidae, most others being mono- or diesters.

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(2S,12Z)-2-Acetoxy-12-heptadecene: Major Sex Pheromone Component of Pistachio Twig Borer, Kermania pistaciella

Cited by 14 publications

References 22 publications

(2S,8Z)-2-Butyroxy-8-heptadecene: Major Component of the Sex Pheromone of Chrysanthemum Gall Midge, Rhopalomyia longicauda

(2S,8Z)-2-Butyroxy-8-heptadecene: Major Component of the Sex Pheromone of Chrysanthemum Gall Midge, Rhopalomyia longicauda

Identification of Female-produced Sex Pheromone of the Honey Locust Gall Midge, Dasineura gleditchiae

(S)-2-Acetoxy-5-Undecanone, Female Sex Pheromone of the Raspberry Cane Midge, Resseliella theobaldi (Barnes)

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