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Chiral-Phase Capillary Gas Chromatography and Mosquito Repellent Activity of Some Oxazolidine Derivatives of (+)- and (−)-Citronello1

Taylor, Wesley G.; Schreck, Carl E.

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  <identifier identifierType="URL"></identifier>
      <creatorName>Taylor, Wesley G.</creatorName>
      <givenName>Wesley G.</givenName>
      <creatorName>Schreck, Carl E.</creatorName>
      <givenName>Carl E.</givenName>
    <title>Chiral-Phase Capillary Gas Chromatography and Mosquito Repellent Activity of Some Oxazolidine Derivatives of (+)- and (−)-Citronello1</title>
    <date dateType="Issued">1985-05-01</date>
  <resourceType resourceTypeGeneral="JournalArticle"/>
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    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1002/jps.2600740508</relatedIdentifier>
    <rights rightsURI="">Creative Commons Zero v1.0 Universal</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
    <description descriptionType="Abstract">Fourteen stereoisomeric mixtures of six oxazolidine heterocycles and one amino alcohol were obtained from commercial samples of (+)−, (−)−, or (±)-citronellol (2) and evaluated in a cloth test system as mosquito repellents. A technical sample of 3-acetyl-2-(2′, 6′-dimethyl-5′-heptenyl)oxazolidine (1), evaluated initially as a mixture of two pairs of enantiomers, was an effective repellent against two of the three species of mosquitoes. To study repellency-stereochemistry relationships, 1 was isolated as fractions G-1, G-2, I-1, and I-2, corresponding to representative samples of the four possible stereoisomers. The enantiomeric composition of 1, but not of the other derivatives, could be determined by chiral-phase capillary gas chromatography with Chirasil-Val. Two chiral phases showed that experimental samples of 1, and hence the commercial samples of 2, were composed of not more than 90% of one enantiomer. Differences in repellency of isomerically enriched samples were generally small. Fraction G, a mixture of diastereoisomers readily prepared from (+)−2, was considerably more effective than standard insect repellents in bioassays with three mosquito species.</description>
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