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High‐performance liquid chromatographic/tandem mass spectrometric identification of the phototransformation products of tebuconazole on titanium dioxide
Author(s) -
Calza Paola,
Baudino Simone,
Aigotti Riccardo,
Baiocchi Claudio,
Branca Paolo,
Pelizzetti Ezio
Publication year - 2002
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.315
Subject(s) - chemistry , tebuconazole , hydroxylation , moiety , titanium dioxide , molecule , high performance liquid chromatography , tandem mass spectrometry , photochemistry , stereochemistry , organic chemistry , mass spectrometry , fungicide , chromatography , chemical engineering , enzyme , botany , engineering , biology
Tebuconazole is a widely used fungicide. The formation of by‐products on irradiated titanium dioxide as a photocatalyst was evaluated. Several species derived from tebuconazole degradation were identified and characterized by HPLC/MS n . A pattern of reactions accounting for the observed intermediates is proposed. Different parallel pathways are operating (and through these pathways the transformation of the molecule proceeds), leading to a wide range of intermediate compounds. All these molecules are more hydrophylic than tebuconazole. The main steps involved are (1) the hydroxylation of the molecule with the formation of three species having [M + H] + 324; the hydroxylation occurs on the C‐1 carbon and on the aromatic ring in the two ortho ‐positions; (2) the cleavage of a C—C bond with the release of the tert ‐butyl moiety and the formation of a species having m / z 250; analogously to step 1, also on this species a further hydroxylation reaction occurs; (3) through the loss of the triazole moiety with the formation of a structure with m / z 257. Copyright © 2002 John Wiley & Sons, Ltd.