Fenarimol solar degradation pathways and photoproducts in aqueous solution.
Identifieur interne : 000087 ( Ncbi/Checkpoint ); précédent : 000086; suivant : 000088Fenarimol solar degradation pathways and photoproducts in aqueous solution.
Auteurs : M Conceiça D A. Mateus [Portugal] ; Abílio M. Da Silva ; Hugh D. BurrowsSource :
- Chemosphere [ 0045-6535 ] ; 2002.
Mots-clés :
- MESH :
- chemical, analysis : Water Pollutants.
- chemical, chemistry : Fungicides, Industrial, Pyrimidines.
- Gas Chromatography-Mass Spectrometry, Photochemistry, Sunlight.
- Keywords (en) : Fungicides, Industrial (chemistry), Gas Chromatography-Mass Spectrometry, Photochemistry, Pyrimidines (chemistry), Sunlight, Water Pollutants (analysis).
Abstract
The degradation photoproducts of the fungicide fenarimol obtained from irradiation of aqueous solutions with sunlight were characterised. The photoproducts resulting from samples with different exposure times were extracted and separated using chromatographic techniques. Seven main photoproducts were detected using high performance liquid chromatography with a photodiode array detector, gas chromatography with mass spectrometry detector and Fourier transform infrared spectroscopy. Structures are suggested for possible photoproducts based on the characterisation results, minimum energy geometry of the parent compound, and the mass spectral behaviour of fenarimol. These correspond to the compounds with m/z 328 (three structural isomers (a), (b) and (c)), m/z 294 (two structural isomers (a) and (b)), m/z 292, 278 and 190. Of the various major products detected, the isomer 328(a) is seen to be particularly unstable under the action of sunlight. The most stable photoproducts are found to be those with m/z 294(a), 278 and 190. However, upon prolonged solar irradiation all of these break down to produce polar, low molecular weight compounds. Comparison with our own and other results on fenarimol photolysis indicate significant solvent effects on the process. The combination of these structural characterisation results and previous data from spectroscopic and photodegradation kinetics studies allows us to suggest some possible mechanisms for the photodegradation of fenarimol under sunlight.
Affiliations:
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pubmed:12146625Le document en format XML
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Da Silva</name></author><author><name sortKey="Burrows, Hugh D" sort="Burrows, Hugh D" uniqKey="Burrows H" first="Hugh D" last="Burrows">Hugh D. Burrows</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2002">2002</date><idno type="RBID">pubmed:12146625</idno><idno type="pmid">12146625</idno><idno type="wicri:Area/PubMed/Corpus">000209</idno><idno type="wicri:Area/PubMed/Curation">000209</idno><idno type="wicri:Area/PubMed/Checkpoint">000200</idno><idno type="wicri:Area/Ncbi/Merge">000087</idno><idno type="wicri:Area/Ncbi/Curation">000087</idno><idno type="wicri:Area/Ncbi/Checkpoint">000087</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Fenarimol solar degradation pathways and photoproducts in aqueous solution.</title><author><name sortKey="Mateus, M Conceica D A" sort="Mateus, M Conceica D A" uniqKey="Mateus M" first="M Conceiça D A" last="Mateus">M Conceiça D A. Mateus</name><affiliation wicri:level="1"><nlm:affiliation>Faculdade de Ciências e Tecnologia, Area Departamental de Química, Universidade do Algarve, Faro, Portugal. mcmateus@mozart.si.ualg.pt</nlm:affiliation><country xml:lang="fr">Portugal</country><wicri:regionArea>Faculdade de Ciências e Tecnologia, Area Departamental de Química, Universidade do Algarve, Faro</wicri:regionArea><wicri:noRegion>Faro</wicri:noRegion></affiliation></author><author><name sortKey="Da Silva, Abilio M" sort="Da Silva, Abilio M" uniqKey="Da Silva A" first="Abílio M" last="Da Silva">Abílio M. Da Silva</name></author><author><name sortKey="Burrows, Hugh D" sort="Burrows, Hugh D" uniqKey="Burrows H" first="Hugh D" last="Burrows">Hugh D. Burrows</name></author></analytic><series><title level="j">Chemosphere</title><idno type="ISSN">0045-6535</idno><imprint><date when="2002" type="published">2002</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Fungicides, Industrial (chemistry)</term><term>Gas Chromatography-Mass Spectrometry</term><term>Photochemistry</term><term>Pyrimidines (chemistry)</term><term>Sunlight</term><term>Water Pollutants (analysis)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analysis" xml:lang="en"><term>Water Pollutants</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Fungicides, Industrial</term><term>Pyrimidines</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Gas Chromatography-Mass Spectrometry</term><term>Photochemistry</term><term>Sunlight</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The degradation photoproducts of the fungicide fenarimol obtained from irradiation of aqueous solutions with sunlight were characterised. The photoproducts resulting from samples with different exposure times were extracted and separated using chromatographic techniques. Seven main photoproducts were detected using high performance liquid chromatography with a photodiode array detector, gas chromatography with mass spectrometry detector and Fourier transform infrared spectroscopy. Structures are suggested for possible photoproducts based on the characterisation results, minimum energy geometry of the parent compound, and the mass spectral behaviour of fenarimol. These correspond to the compounds with m/z 328 (three structural isomers (a), (b) and (c)), m/z 294 (two structural isomers (a) and (b)), m/z 292, 278 and 190. Of the various major products detected, the isomer 328(a) is seen to be particularly unstable under the action of sunlight. The most stable photoproducts are found to be those with m/z 294(a), 278 and 190. However, upon prolonged solar irradiation all of these break down to produce polar, low molecular weight compounds. Comparison with our own and other results on fenarimol photolysis indicate significant solvent effects on the process. The combination of these structural characterisation results and previous data from spectroscopic and photodegradation kinetics studies allows us to suggest some possible mechanisms for the photodegradation of fenarimol under sunlight.</div></front></TEI><affiliations><list><country><li>Portugal</li></country></list><tree><noCountry><name sortKey="Burrows, Hugh D" sort="Burrows, Hugh D" uniqKey="Burrows H" first="Hugh D" last="Burrows">Hugh D. Burrows</name><name sortKey="Da Silva, Abilio M" sort="Da Silva, Abilio M" uniqKey="Da Silva A" first="Abílio M" last="Da Silva">Abílio M. Da Silva</name></noCountry><country name="Portugal"><noRegion><name sortKey="Mateus, M Conceica D A" sort="Mateus, M Conceica D A" uniqKey="Mateus M" first="M Conceiça D A" last="Mateus">M Conceiça D A. Mateus</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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