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Analysis of the sulfonylurea herbicide metsulfuron-methyl and its metabolites in the soil of cereal crops. Comparative analytical chemistry of the sulfonylureas

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Rouchaud, Jean [UCL] Neus, O Moulard, C.

For the analysis of metsulfuron-methyl in the crop soils with a sensitivity limit of 0.3 mug kg(-1) dry soil, in the soil extract metsulfuron-methyl was separated from its soil metabolites and the soil impurities by repeated thin-layer chromatographies (TLC). In the cleaned soil extract, diazomethane transformed metsulfuron-methyl 1 into N,N' -dimethyl metsulfuron-methyl 2 (methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]methylamino]sulfonyl]benzoate). In the gas-liquid chromatograph with detection by electron capture (GC-EC) and in the combined gas chromatograph-mass spectrometer (GC-MS), 2 was transformed into 1-dioxy-2-N-methyl-3-keto-1,2-benzisothiazole 3 which was measured by GC-EC with confirmation by GC-MS. The metsulfuron-methyl soil metabolites 2-sulfonamido-methylbenzoate 6, 1-dioxy-3-keto-1,2-benzisothiazole (saccharin) 7 and 2-sulfonamidobenzoic acid 8 were analyzed in the soil of winter wheat crops by a procedure similar to the one for metsulfuron-methyl. After their separation and purification in the soil extracts by TLC, 7 and 8 were methylated, and analyzed as 3 in the GC-EC and GC-MS apparatus where the generated 6 was quantitatively transformed into 3; 6 was analyzed as such with the GC and GC-MS apparatus wherein it was transformed into 3. The sensitivity limit for each metabolite was 0.3 mug of equivalents of metsulfuron-methyl kg(-1) dry soil. The syntheses of the analysis standards of the metsulfuron-methyl derivatives 2 and 3, and of the metsulfuron-methyl metabolites 6, 7 and 8 are described. The transformation pathways of metsulfuron-methyl and of its derivatives are different from those of the pyridine-pyrimidine sulfonylurea herbicides flupyrsulfuron-methyl and rimsulfuron. The soil analysis of a sulfonylurea -by means of one of its transformation product- needs a previous study of the chemical reactivity of the sulfonylurea. This leads to the analysis procedures for the main soil metabolites of the sulfonylurea.

Document type Article de périodique (Journal article) – Article de recherche
Publication date 2001
Language Anglais
Journal information "International Journal of Environmental Analytical Chemistry" - Vol. 79, no. 1, p. 65-80 (2001)
Peer reviewed yes
Publisher Gordon Breach Publishing, Taylor & Francis Group (Philadelphia)
issn 0306-7319
e-issn 1029-0397
Publication status Publié
Affiliation UCL - AGRO/BAPA - Département de biologie appliquée et des productions agricoles
Keywords metsulfuron-methyl ; soil metabolites ; gas chromatography ; combined gas chromatography-mass spectrometry
Links
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Bibliographic reference Rouchaud, Jean ; Neus, O ; Moulard, C.. Analysis of the sulfonylurea herbicide metsulfuron-methyl and its metabolites in the soil of cereal crops. Comparative analytical chemistry of the sulfonylureas. In: International Journal of Environmental Analytical Chemistry, Vol. 79, no. 1, p. 65-80 (2001)
Permanent URL http://hdl.handle.net/2078.1/42555