Journal article Open Access
Taylor, Wesley G.; Schreck, Carl E.
<?xml version='1.0' encoding='utf-8'?> <resource xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns="http://datacite.org/schema/kernel-4" xsi:schemaLocation="http://datacite.org/schema/kernel-4 http://schema.datacite.org/meta/kernel-4.1/metadata.xsd"> <identifier identifierType="URL">https://zenodo.org/record/1229253</identifier> <creators> <creator> <creatorName>Taylor, Wesley G.</creatorName> <givenName>Wesley G.</givenName> <familyName>Taylor</familyName> </creator> <creator> <creatorName>Schreck, Carl E.</creatorName> <givenName>Carl E.</givenName> <familyName>Schreck</familyName> </creator> </creators> <titles> <title>Chiral-Phase Capillary Gas Chromatography and Mosquito Repellent Activity of Some Oxazolidine Derivatives of (+)- and (−)-Citronello1</title> </titles> <publisher>Zenodo</publisher> <publicationYear>1985</publicationYear> <dates> <date dateType="Issued">1985-05-01</date> </dates> <resourceType resourceTypeGeneral="JournalArticle"/> <alternateIdentifiers> <alternateIdentifier alternateIdentifierType="url">https://zenodo.org/record/1229253</alternateIdentifier> </alternateIdentifiers> <relatedIdentifiers> <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1002/jps.2600740508</relatedIdentifier> </relatedIdentifiers> <rightsList> <rights rightsURI="https://creativecommons.org/publicdomain/zero/1.0/legalcode">Creative Commons Zero v1.0 Universal</rights> <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights> </rightsList> <descriptions> <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> </descriptions> </resource>