High-performance liquid chromatographic/tandem mass spectrometric identification of the phototransformation products of tebuconazole on titanium dioxide.
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.
Dipartimento di Chimica Analitica, Università di Torino, via P. Giuria 5, 10125 Turin, Italy. Paola.Calza@unito.it
Paola
P
Calza
Simone
S
Baudino
Riccardo
R
Aigotti
Claudio
C
Baiocchi
Paolo
P
Branca
Ezio
E
Pelizzetti
D002851:Chromatography, High Pressure Liquid; D005659:Fungicides, Industrial / Q000528:radiation effects*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D015394:Molecular Structure; D008970:Molecular Weight; D010084:Oxidation-Reduction; D010573:Pesticide Residues / Q000032:analysis*; D010777:Photochemistry; D014025:Titanium; D014230:Triazoles / Q000528:radiation effects*
D005659:Fungicides, Industrial; D010573:Pesticide Residues; D014230:Triazoles; C009495:titanium dioxide; C087114:tebuconazole; D014025:Titanium