Metabolism of 7-Fluoro-6-(3,4,5,6-tetrahydrophthalimido)-4- (2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (S-53482) in Rat. 1. Identification of a Sulfonic Acid Type Conjugate

To examine the metabolic fate of 7-fluoro-6-(3,4,5,6-tetrahydrophthalimido)-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (S-53482), rats were given a single oral dose of [phenyl-14C]-S-53482 at 1 (low) or 100 (high) mg/kg. The radiocarbon was almost completely eliminated within 7 days after administra...

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Published in:Journal of agricultural and food chemistry 1999-01, Vol.47 (1), p.305-312
Main Authors: Tomigahara, Yoshitaka, Matsui, Masayoshi, Matsunaga, Haruyuki, Isobe, Naohiko, Kaneko, Hideo, Nakatsuka, Iwao, Yoshitake, Akira, Yamane, Setsuo
Format: Article
Language:English
Subjects:
Animals
Benzoxazines
Biological and medical sciences
Female
herbicide residues
herbicides
Herbicides - metabolism
Male
Medical sciences
metabolism
metabolites
Oxazines - metabolism
Pesticides, fertilizers and other agrochemicals toxicology
Phthalimides - metabolism
Rats
Rats, Sprague-Dawley
spectral analysis
Sulfonic Acids - metabolism
Toxicology
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Summary:To examine the metabolic fate of 7-fluoro-6-(3,4,5,6-tetrahydrophthalimido)-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (S-53482), rats were given a single oral dose of [phenyl-14C]-S-53482 at 1 (low) or 100 (high) mg/kg. The radiocarbon was almost completely eliminated within 7 days after administration in both groups. 14C recoveries (expressed as percentages relative to the dosed 14C) in feces and urine were 56−72 and 31−43%, respectively, for the low dose and 78−85 and 13−23%, respectively, for the high dose. S-53482 and seven metabolites were identified in urine and feces. Six of them were purified by several chromatographic techniques and identified by spectroanalyses (NMR and MS). Alcohol derivatives and an acetoanilide derivative were isolated from urine. Three sulfonic acid conjugates having a sulfonic acid group incorporated into the double bond of the 3,4,5,6-tetrahydrophthalimide moiety were isolated from feces. On the basis of the metabolites identified in this study, the metabolic pathways of S-53482 in rats are proposed. Keywords: Metabolism; herbicide; rat; identification; sulfonic acid conjugate; excretion; biotransformation
ISSN:0021-8561
1520-5118
DOI:10.1021/jf980516q