title: Identification of metabolites of propyrisulfuron in rats.
abstract: The metabolites found in the urine, feces and bile of male and female rats administered with (14)C-labeled herbicide, propyrisulfuron [1-(2-chloro-6-propylimidazo[1,2-b]pyridazin-3-ylsulfonyl)-3- (4,6-dimethoxypyrimidin-2-yl)urea] were identified by high-performance liquid chromatography (HPLC) with the ultraviolet (UV) and radioisotope (RI) detectors, tandem mass spectrometry and nuclear magnetic resonance (NMR). Administered (14)C was excreted into the urine (5.7-29.8%) and feces (64.6-97.4%). Urine and bile samples were concentrated and purified using a solid-phase extraction cartridge, and fecal homogenates were extracted using acetonitrile. Conjugates were hydrolyzed with enzyme or hydrochloric acid solution for identification. The proposed major metabolic reactions of propyrisulfuron are as follows: (1) hydroxylation of the pyrimidine ring, propyl group, and imidazopyridazine ring, (2) O-demethylation, (3) cleavage of the pyrimidine ring, and (4) glucuronic acid and sulfate conjugation. The metabolic patterns found are not different among sulfonylurea herbicides.
authors.affiliation: Environmental Health Science Laboratory, Sumitomo Chemical Co., Ltd., 1-98, 3-Chome, Kasugade-Naka, Konohana-Ku, Osaka 554-8558, Japan. Electronic address: takakut@sc.sumitomo-chem.co.jp.
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Takaku
authors.affiliation: Environmental Health Science Laboratory, Sumitomo Chemical Co., Ltd., 1-98, 3-Chome, Kasugade-Naka, Konohana-Ku, Osaka 554-8558, Japan.
authors.forename: Kazuki
authors.initials: K
authors.lastname: Mikata
authors.affiliation: Environmental Health Science Laboratory, Sumitomo Chemical Co., Ltd., 1-98, 3-Chome, Kasugade-Naka, Konohana-Ku, Osaka 554-8558, Japan.
authors.forename: Hirohisa
authors.initials: H
authors.lastname: Nagahori
authors.affiliation: Environmental Health Science Laboratory, Sumitomo Chemical Co., Ltd., 1-98, 3-Chome, Kasugade-Naka, Konohana-Ku, Osaka 554-8558, Japan.
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Sogame
mesh_terms: D000818:Animals; D001646:Bile / Q000737:chemistry; D002853:Chromatography, Liquid / Q000379:methods; D005243:Feces / Q000737:chemistry; D005260:Female; D006540:Herbicides / Q000009:adverse effects / Q000032:analysis / Q000737:chemistry* / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry / Q000379:methods; D011725:Pyridines / Q000009:adverse effects / Q000032:analysis / Q000737:chemistry* / Q000378:metabolism*; D011743:Pyrimidines / Q000009:adverse effects / Q000032:analysis / Q000737:chemistry* / Q000378:metabolism*; D051381:Rats; D017208:Rats, Wistar
chemical_list: D006540:Herbicides; D011725:Pyridines; D011743:Pyrimidines
keywords: LC–MS/MS; Metabolism; NMR; Propyrisulfuron; Rat