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Article: A mechanistic study on the photodegradation of Irgarol-1051 in natural seawater

TitleA mechanistic study on the photodegradation of Irgarol-1051 in natural seawater
Authors
KeywordsAntifouling booster biocide
Degradation intermediates
Degradation kinetics
Irgarol-1051
Mechanistic studies
Photodegradation
Issue Date2009
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/marpolbul
Citation
Marine Pollution Bulletin, 2009, v. 58 n. 2, p. 272-279 How to Cite?
AbstractThe kinetics of the photoinduced degradation and transformation of the antifouling booster biocide, Irgarol-1051, in natural coastal seawater was studied. The measured first-order rate constant for the degradation of Irgarol-1051 was 4.02 ± 0.1 × 10-4 h-1, while the rate constant for the formation of 2-methylthio-4-tert-butylamino-6-amino-s-triazine (M1), the most dominant degradation product of Irgarol-1051, was 4.6 ± 0.1 × 10-5 h-1. This considerably slower rate suggested that the transformation of Irgarol-1051 to M1 may not be the predominant pathway of the photodegradation process. During the photodegradation study, a new s-triazine species was observed in the degradation mixtures which, together with M1, appeared immediately upon photolysis and continued to accumulate in the degradation mixture throughout the entire study duration. This is in contrast to the behaviour of the recently identified degradation product of Irgarol-1051, 3-[4-tert-butylamino-6-methylthiol-s-triazin-2-ylamino]- propionaldehyde (M2), which was only detected in the degradation mixture after a long induction period. High-resolution tandem mass spectrometric analysis hinted that the new degradation product (M4) may possess a terminal alcohol and is likely to be an N-allylic alcohol derivative of M1. This suggests that M4 may, indeed, be a precursor of M2 via redox transformation at its N-allylic alcohol functionality. © 2008 Elsevier Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/60653
ISSN
2023 Impact Factor: 5.3
2023 SCImago Journal Rankings: 1.445
ISI Accession Number ID
Funding AgencyGrant Number
Council of Hong Kong SAR, China1445/05M
Funding Information:

The work described in this paper was supported by a grant from the Research Grants Council of Hong Kong SAR, China (CityU 1445/05M).

References

 

DC FieldValueLanguage
dc.contributor.authorLam, KHen_HK
dc.contributor.authorLei, NYen_HK
dc.contributor.authorTsang, VWHen_HK
dc.contributor.authorCai, Zen_HK
dc.contributor.authorLeung, KMYen_HK
dc.contributor.authorLam, MHWen_HK
dc.date.accessioned2010-05-31T04:15:54Z-
dc.date.available2010-05-31T04:15:54Z-
dc.date.issued2009en_HK
dc.identifier.citationMarine Pollution Bulletin, 2009, v. 58 n. 2, p. 272-279en_HK
dc.identifier.issn0025-326Xen_HK
dc.identifier.urihttp://hdl.handle.net/10722/60653-
dc.description.abstractThe kinetics of the photoinduced degradation and transformation of the antifouling booster biocide, Irgarol-1051, in natural coastal seawater was studied. The measured first-order rate constant for the degradation of Irgarol-1051 was 4.02 ± 0.1 × 10-4 h-1, while the rate constant for the formation of 2-methylthio-4-tert-butylamino-6-amino-s-triazine (M1), the most dominant degradation product of Irgarol-1051, was 4.6 ± 0.1 × 10-5 h-1. This considerably slower rate suggested that the transformation of Irgarol-1051 to M1 may not be the predominant pathway of the photodegradation process. During the photodegradation study, a new s-triazine species was observed in the degradation mixtures which, together with M1, appeared immediately upon photolysis and continued to accumulate in the degradation mixture throughout the entire study duration. This is in contrast to the behaviour of the recently identified degradation product of Irgarol-1051, 3-[4-tert-butylamino-6-methylthiol-s-triazin-2-ylamino]- propionaldehyde (M2), which was only detected in the degradation mixture after a long induction period. High-resolution tandem mass spectrometric analysis hinted that the new degradation product (M4) may possess a terminal alcohol and is likely to be an N-allylic alcohol derivative of M1. This suggests that M4 may, indeed, be a precursor of M2 via redox transformation at its N-allylic alcohol functionality. © 2008 Elsevier Ltd. All rights reserved.en_HK
dc.languageengen_HK
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/marpolbulen_HK
dc.relation.ispartofMarine Pollution Bulletinen_HK
dc.subjectAntifouling booster biocideen_HK
dc.subjectDegradation intermediatesen_HK
dc.subjectDegradation kineticsen_HK
dc.subjectIrgarol-1051en_HK
dc.subjectMechanistic studiesen_HK
dc.subjectPhotodegradationen_HK
dc.titleA mechanistic study on the photodegradation of Irgarol-1051 in natural seawateren_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0025-326X&volume=58&spage=272&epage=279&date=2009&atitle=A+mechanistic+study+on+the+photodegradation+of+Irgarol-1051+in+natural+seawater+en_HK
dc.identifier.emailLeung, KMY: kmyleung@hku.hken_HK
dc.identifier.authorityLeung, KMY=rp00733en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/j.marpolbul.2008.09.009en_HK
dc.identifier.pmid18977497-
dc.identifier.scopuseid_2-s2.0-59849113726en_HK
dc.identifier.hkuros155374en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-59849113726&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume58en_HK
dc.identifier.issue2en_HK
dc.identifier.spage272en_HK
dc.identifier.epage279en_HK
dc.identifier.isiWOS:000264421400024-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridLam, KH=8404299800en_HK
dc.identifier.scopusauthoridLei, NY=25224506700en_HK
dc.identifier.scopusauthoridTsang, VWH=8404299300en_HK
dc.identifier.scopusauthoridCai, Z=7402904946en_HK
dc.identifier.scopusauthoridLeung, KMY=7401860738en_HK
dc.identifier.scopusauthoridLam, MHW=7202630175en_HK
dc.identifier.issnl0025-326X-

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