Using mass spectrometry to highlight structures of degradation compounds obtained by photolysis of chloroacetamides: case of acetochlor.

Yasmine Souissi 1 Sophie Bourcier 1 Sélim Ait-Aissa 2 Emmanuelle Maillot-Maréchal 2 Stéphane Bouchonnet 1 Christophe Genty 1 Michel Sablier 1
1 DCMR - Laboratoire des mécanismes réactionnels
2 INERIS - Institut National de l'Environnement Industriel et des Risques
Abstract : The photooxidation of acetochlor (a pesticide belonging to the acetamides group) using a polychromatic UV irradiation in ultrapure water was studied. This study reports the efficiency of mass spectrometry for the characterization of photodegradation products of acetochlor. Decompositions of protonated ions MH+are proposed in electrospray (ESI) mode for LC-MS, while electron ionization (EI) and chemical ionization modes (CI) are used for GC-MS. The knowledge of fragmentation and the use of a combination of experiments (MS/MS, high resolution) allow the characterization of photoproducts. Structural elucidation is assisted by the use of photolysed deuterated compounds. Fifteen major degradation products have been characterized, five by LC-QTOF, six photoproducts by GC-ITMS, and four are observed by both techniques. In vitro bioassays based on the quantification of receptor-mediated activity demonstrated that acetochlor photolysis engenders a moderate but significant estrogenic activity. Moreover, a quantitative structure-activity relationship (QSAR) approach was used to assess the potential toxicity effect of acetochlor and its by-products. The predictions were analyzed showing a variety of toxicity profiles of acetochlor photoproducts depending on the toxicological investigated endpoint.
Document type :
Journal articles
Complete list of metadatas
https://hal-polytechnique.archives-ouvertes.fr/hal-00880179
Contributor : Denis Roura <>
Submitted on : Wednesday, November 6, 2013 - 2:30:06 PM
Last modification on : Friday, August 30, 2019 - 4:52:02 PM

Identifiers

Collections

CNRS | X-DCMR | X | PARISTECH | INERIS | X-DEP-CHIM

Citation

Yasmine Souissi, Sophie Bourcier, Sélim Ait-Aissa, Emmanuelle Maillot-Maréchal, Stéphane Bouchonnet, et al.. Using mass spectrometry to highlight structures of degradation compounds obtained by photolysis of chloroacetamides: case of acetochlor.. Journal of Chromatography A, Elsevier, 2013, 1310 (1), pp.98-112. ⟨10.1016/j.chroma.2013.07.091⟩. ⟨hal-00880179⟩

Export

BibTeX TEI DC DCterms EndNote

Share

Metrics

Record views

395

Contact

Informations

CCSD