Monitoring of Photodegradation Process of Various Benzothiazoles by HPLC and UV Spectrometry: Application of LC-MS in Photoproduct Identification

REFERENCES

• Reddy , C.M. ; Quinn , J.G. Environmental chemistry of benzothiazoles derived from rubber . Environ. Sci. Technol. 1997 , 31 ( 10 ), 2847 – 2853 .
   Web of Science ®Google Scholar
• Vogt , S. F. 2-Mercaptobenzothiazole; Final Test Rule . Fed. Reg. 1988 , 53 ( 173 ), 34514 – 34532 .
   Google Scholar
• Liska , I. ; Brouwer , E.R. ; Ostheimer , A.G.L. ; Lingeman , H. ; Brinkman , U.Th.A.T. ; Geerdink , R.B. ; Mulder , W.H. Rapid screening of a large group of polar pesticides in river water by on-line trace enrichment and column liquid chromatography . Intl. J. Environ. Anal. Chem. 1992 , 47 ( 4 ), 267 – 291 .
   Web of Science ®Google Scholar
• Besse , P. ; Combourieu , B. ; Boyse , G. ; Sancelme , M. ; De Wever , H. ; Delort , A. Long-range 1H-15 N heteronuclear shift correlation at natural abundance: A tool to study benzothiazole biodegradation by two Rhodococcus strains . Appl. Environ. Microbiol. 2001 , 67 ( 4 ), 1412 – 1417 .
   PubMed Web of Science ®Google Scholar
• Kloepfer , A. ; Jekel , M. ; Reemtsma , T. Occurrence, sources, and fate of benzothiazoles in municipal wastewater treatment plants . Environ. Sci. Technol. 2005 , 39 ( 10 ), 3792 – 3798 .
   PubMed Web of Science ®Google Scholar
• Bujdakova , H. ; Kuchta , T. ; Sidoova , E. ; Gvozdjakova , A. Anti-Candida activity of four antifungal benzothiazoles . FEMS Microbiol. Lett. 1993 , 112 ( 3 ), 329 – 333 .
   PubMed Web of Science ®Google Scholar
• Rennie , P.J. Determination of 2-mercaptobenzothiazole in river water by HPLC . Chromatographia. 1988 , 26 , 297 – 299 .
   Web of Science ®Google Scholar
• www.epa.gov/pesticides/foia/reviews/051704
   Google Scholar
• Fiehn , O. ; Reemtsma , T. ; Jekel , M. Extraction and analysis of various benzothiazoles from industrial wastewater . Anal. Chim. Acta. 1994 , 295 ( 3 ), 297 – 305 .
   Web of Science ®Google Scholar
• www.pesticideinfo.org (PAN Pesticide Database, Version 8.1, Sept. 16, 2008)
   Google Scholar
• De Vos , D. ; De Wever , H. ; Verachtert , H. Parameters affecting the degradation of benzothiazoles and benzimidazoles in activated sludge systems . Appl. Microbiol. Biotechnol. 1993 , 39 ( 4–5 ), 622 – 626 .
   PubMed Web of Science ®Google Scholar
• De Wever , H. ; Verachtert , H. 2-mercaptobenzothiazole degradation in laboratory fed-batch systems . Appl. Microbiol. Biotechnol. 1994 , 42 ( 4 ), 623 – 630 .
   PubMed Web of Science ®Google Scholar
• Reemtsma , T. ; Fiehn , O. ; Kalnowski , G. ; Jekel , M. Microbial transformations and biological effects of fungicide-derived benzothiazoles determined in industrial wastewater . Environ. Sci. Technol. 1995 , 29 ( 2 ), 478 – 485 .
   PubMed Web of Science ®Google Scholar
• Nawrocki , S.T. ; Drake , K.D. ; Watson , C.F. ; Foster , G.D. ; Maier , K.J. Comparative aquatic toxicity evaluation of 2-(thiocyanomethylthio)benzothiazole and selected degradation products using ceriodaphnia dubia . Arch. Environ. Contam. Toxicol. 2005 , 48 ( 3 ), 344 – 350 .
   PubMed Web of Science ®Google Scholar
• Warner , J.S. ; Engel , T.M. ; Mondron , P.J. Determination of MBTS and TCMTB in industrial and municipal wastewaters . Report. 1985 , ( EPA/600/4–85/028; Order No. PB85–189025 ), 46 pp.
   Google Scholar
• Warner , J.S. ; Engel , T.M. ; Mondron , P.J. Determination of mercaptobenzothiazole in industrial and municipal wastewaters . Report 1985 , ( EPA/600/4–85/026; Order No. PB85–191120 ), 45 pp.
   Google Scholar
• Knepper , T.P. ; Barcelo , D. ; Lindner , K. ; Seel , P. ; Reemtsma , T. ; Ventura , F. ; de Wever , H. Removal of persistent polar pollutants through improved treatment of wastewater effluents (P-THREE). Water Sci. Technol.: A J. Intl. Assoc. Water Pollut. Res. 2004, 50 (5), 195–202.
   PubMed Web of Science ®Google Scholar
• Malouki , M.A. ; Richard , C. ; Zertal , A. Photolysis of 2-mercaptobenzothiazole in aqueous medium . Laboratory and field experiments. J. Photochem. Photobiol. A Chem. 2004 , 167 ( 2–3 ), 121 – 126 .
   Web of Science ®Google Scholar
• Andreozzi , R. ; Caprio , V. ; Marotta , R. Oxidation of Benzothiazole, 2-mercaptobenzothiazole and 2-hydroxybenzothiazole in aqueous solution by H2O2/UV or photoassisted fenton systems . J. Chem. Technol. Biotechnol. 2001 , 76 ( 2 ), 196 – 202 .
   Web of Science ®Google Scholar
• Valdes , H. ; Zaror , C.A. ; Jekel , M. Kinetic study of reactions between ozone and benzothiazole in water . Water Sci. Technol.: A. J. Intl. Assoc. Water Pollut. Res. 2003 , 48 ( 11–12 ), 505 – 510 .
   PubMed Web of Science ®Google Scholar
• Fiehn , O. ; Wegener , G. ; Jochimsen , J. ; Jekel , M. Analysis of the ozonation of 2-mercaptobenzothiazole in water and tannery wastewater using sum parameters, liquid- and gas chromatography and capillary electrophoresis . Water Res. 1998 , 32 ( 4 ), 1075 – 1084 .
   Web of Science ®Google Scholar
• Barnes , K.A. ; Castle , L. ; Damant , A.P. ; Read , W.A. ; Speck , D.R. Development and application of an LC-MS method to determine possible migration of mercaptobenzothiazole, benzothiazole and related vulcanization residues from rubber used in contact with food and drink . Food Addit. Contam. 2003 , 20 ( 2 ), 196 – 205 .
   PubMed Web of Science ®Google Scholar
• Martinez , K. ; Ferrer , I. ; Barcelo , D. Part-per-trillion level determination of antifouling pesticides and their byproducts in seawater samples by off-line solid-phase extraction followed by high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry . J. Chromatogr. A. 2000 , 879 ( 1 ), 27 – 37 .
   PubMed Web of Science ®Google Scholar
• Reemtsma , T. Determination of 2-substituted benzothiazoles of industrial use from water by liquid chromatography/electrospray ionization tandem mass spectrometry . Rapid Commun. Mass Spectrom. 2000 , 14 ( 17 ), 1612 – 1618 .
   PubMed Web of Science ®Google Scholar
• Zajíčková , Z. ; Párkányi , C. Photodegradation of 2-Mercaptobenzothiazole disulfide and related benzothiazoles . J. Heterocycl. Chem. 2008 , 45 ( 1 ), 303 – 306 .
   Google Scholar
• Gaplovsky , A. ; Jakubikova , B. ; Hercek , R. ; Donovalova , J. Ultraviolet photodegradation of benzothiazole derivatives and their photochemical reactivity in the presence of carbon tetrachloride . J. Trace Microprobe Tech. 2000 , 18 ( 3 ), 419 – 424 .
   Google Scholar
• Párkányi , C. ; Abdelhamid , A.O. Photodegradation of pesticides: photolysis of 2-mercaptobenzothiazole and 2-mercaptobenzimidazole . Heterocycles. 1985 , 23 ( 11 ), 2917 – 2926 .
   Web of Science ®Google Scholar
• Hercek , R. ; Gaplovsky , A. ; Kubinec , R. Phototransformation of some 2-alkyloxybenzothiazole derivatives . Toxicol. Environ. Chem. 1999 , 68 ( 3–4 ), 457 – 469 .
   Google Scholar
• Gaplovsky , A. ; Hercek , R. ; Kuran , P. Photoisomerization of some 2-alkylthiobenzothiazoles . Chem. Pap. 2001 , 55 ( 1 ), 45 – 48 .
   Web of Science ®Google Scholar
• Gaplovsky , A. ; Hercek , R. ; Kuran , P. Phototransformation of some 2-alkylthio- and 2-arylthiobenzothiazole derivatives. Toxicol. Environ. Chem. 1997, 64 (1–4), 155–171.
   Google Scholar
• Brown , D.A. ; Bogge , H. ; Lipunova , G.N. ; Muller , A. ; Plass , W. ; Walsh , K.G. Iron and manganese complexes of benzothiazolylformazans . Inorg. Chim. Acta. 1998 , 280 ( 1–2 ), 30 – 38 .
   Web of Science ®Google Scholar
• Miyashita , A. ; Nagasaki , I. ; Kawano , A. ; Suzuki , Y. ; Iwamoto , K. ; Higashino , T. Electrophilic Cyanations . I. Synthesis of thiocyanato heteroarenes and tosylheteroarenes from mercapto heteroarenes using p-toluenesulfonyl cyanide. Heterocycles. 1997 , 45 ( 4 ), 745 – 755 .
   Google Scholar