Über den stoffwechsel von Harnstoff-Herbiciden in der ratte. 1. Mitteilung. Monuron und Aresin

Ernst, W.; Böhme, Chr.

doi:10.1016/s0015-6264(65)80285-1

Cited by 23 publications

(7 citation statements)

References 9 publications

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“…The latter results confirmed the earlier reports of Swanson & Swanson (1968) that sequential demethylation proceeds in plants. Similar sequence of trans- formation of monuron and other substituted ureas have been reported in fungus (Murray, Reick & Lynd, 1969} bacteria (Geissbuhler et al, 1963, and rat (Ernst & Bohme, 1965).…”

Section: Metabolism Of Monuron In Excised Leaves Of Bean and Cornsupporting

confidence: 75%

“…This is a good illustration of enzyme-substrate specificity which definitely suggested that at least three metabolites conjugated with mono-^-i)-glucose as reported by Pridham (1965), and that the cleavage was not the result of microbial action. The labelled metabolites which formed conjugates with glucose {Ry = 0-17, 0-34 and 0-44) from the bean and corn were tentatively identified by comparing their Rp values with reference compounds in the three solvent systems as used by Ernst & Bohme (1965) (Table 2), to be .^'-(2-hydroxyl-4-chlorophenyl) urea, jV'-(2-hydroxyl-4-chlorophenyl)-J^-methylurea and JV'-(2-hydroxyl-4-chIorophenyl)-A',jV-dimethylurea. Figure 2 shows proposed pathways of monuron transformation in bean and corn plants.…”

Section: Idenlijication Of Unknown Metabolite Conjugatesmentioning

confidence: 99%

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Metabolism of Monuron in Excised Leaves of Corn and Bean Plants*

Lee

Fang

1973

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The metabolism of monuron in excised leaves of bean {Phaseolus vtilgaris L., var. Black Valentine) and corn {Zfa mays L., var. Batam Gross) were studied witb carbonyl-'*C-labelled monuron. The metabolic conversions of monuron in both plant species were exponential and followed first order reaction kinetics. The metabolism of monuron can be divided into two major pathways: demethylation and hydroxylation. At a monuron concentration of 16 ppm the hydroxylation was dominant in the bean leaves. As the concentration of montiron was increased the participation ofthe hydroxylation pathway became less probably due to the inhibition of enzymes involved by monuron. The demethylation pathway was not affected by higher monuron concentration. In the corn leaf, however, sequential demethylation was always the major pathway of monuron transformation and there was no inhibitory effect observed on either pathways as the concentration of monuron increased. The following radioactive metaboiites were found in the alcohol extract of bean and com leaves receiving carbonyl-'

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Section: Metabolism Of Monuron In Excised Leaves Of Bean and Cornsupporting

confidence: 75%

Section: Idenlijication Of Unknown Metabolite Conjugatesmentioning

confidence: 99%

Metabolism of Monuron in Excised Leaves of Corn and Bean Plants*

Lee

Fang

1973

Weed Research

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“…6 The major route of metabolism of MON in male albino rats, strain not reported, is via oxidative N-demethylation and aro-matic hydroxylation but some chlorinated aniline derivatives are also produced. 7 The principal urinary metabolites are N-(4-chlorophenyl )urea (14.5% dose), N-(2-hydroxy-4-chlorophenyl )-urea (6.5%), N-(3-hydroxy-4-chlorophenyl )urea (2.2%) with some mono-and dimethyl urea and 2-acetamido-2-chloro-phenol. The phenolic metabolites of MON are excreted in the urine as conjugates.…”

Section: Introductionmentioning

confidence: 99%

Transcriptomic alterations induced by Monuron in rat and human renal proximal tubule cells in vitro and comparison to rat renal-cortex in vivo

et al. 2015

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-dimethyl-3-(4-chlorophenyl)urea) is a non-selective phenylurea herbicide, widely used in developing countries although concerns have been raised about its toxicity and carcinogenicity. Monuron was evaluated by the National Toxicology Program in 1988 and shown to be a male rat-specific renal carcinogen. We report that oral administration of Monuron to male rats for 3 days, leads to a larger number of genes being differentially expressed in the renal-cortex than in the liver. Further, we observed up-regulation of cell cycle genes and genes involved in cell proliferation in the renalcortex while in the liver xenobiotic metabolising enzymes were up-regulated. We also identified one commonly down-regulated gene in both organs -fragile histidine triad gene (Fhit), a putative tumour suppressor gene; however the down-regulation was only significant at the protein level in the liver. In addition, we conducted in vitro wholegenome transcriptomics studies with human and rat renal cortical cells. Rat cells exposed to Monuron showed down-regulation of sterol biosynthesis, spliceosome and cell cycle genes and up-regulation of genes involved in amino acid metabolism and transport. No genes were found to be differentially expressed in human cells exposed to Monuron. Overall, the findings from the in vitro studies showed very little overlap with the whole animal findings.

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“…This suggests that dealkylation was a primary reaction in mammalian tissues. N-Dealkoxylation was a major reaction with linuron and monolinuron (Bohme and Ernst, 1965;Ernst and Bohme, 1965;Geissbuhler et al, 1965).…”

Section: Mammalian Metabolism Of Substituted Urea Pesticidesmentioning

confidence: 99%

“…It has been demonstrated that most urinary metabolites retain the urea moiety, and many are in the form of hydroxylated derivatives. All the herbicides tested were altered to some degree by the animal (Ernst and Bohme, 1965). It was noted that compounds with monochlorine substituents at the para position yielded primarily meta-hydroxylated derivatives; dichloro compounds gave 6-hydroxy derivatives, and all were subject to conjugation as glucuronides and ethereal sulfates (Geissbiihler et al, 1975).…”

Section: Mammalian Metabolism Of Substituted Urea Pesticidesmentioning

confidence: 99%

Excretion balance, metabolic fate, and tissue residues of N-Phenyl-N'-1,2,5-Thiadiazol-3-Ylurea (Photothidiazuron) in rats

Johnson¹

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"Thidiazuron (DROPP[copyright]) or N-phenyl-N'-1,2,3-thiadiazol-5-ylurea is a promising new cotton defoliant currently being developed by NOR-AM Agricultural Products, Incorporated. In addition to its defoliating activity, thidiazuron demonstrates strong inhibition of regrowth with no adverse effect on the opening or quality of fiber of mature bolls not open at the time of application (Anonymous, 1975). These attributes indicate this could be a useful product. With the possibility of widespread use of thidiazuron in cotton growing regions, it is necessary to consider the result of its photodegradation. The major thidiazuron conversion product, which occurs on the plant surface, is photothidiazuron or N-phenyl-N'-1,2,5-thiadiazol-3-ylurea (Anonymous, 1976). This new compound is the result of a rearrangement in the thiadiazol moiety (Anonymous, 1976). Thidiazuron and photothidiazuron are classified chemically as substituted ureas. This includes a broad group of compounds varying greatly in their molecular substituents and commercial uses. However, most substituted ureas are herbicides, and therefore, the orientation of research has been directed to plant and soil situations. Research data pertaining to the effects of substituted ureas upon mammalian and other animal systems is very limited (Geissbuhler, et al., 1975). Since it is possible that leaves and other parts of a thidiazuron treated cotton plant may be incorporated into livestock feed or eaten by other animals, it is essential to examine certain of the properties of photothidiazuron in relation to mammalian systems. The purpose of this study was to determine the excretion balance, metabolic fate, and tissue residues of photothidiazuron in rats. Specifically, the objectives were: 1. To determine the excretion balance, metabolic fate, and tissue residues after the administration of a single oral dose of photothidiazuron-14 aniline- C to male rats, 2. To investigate the degradation of photothidiazuron by rat liver subcellular fractions and by a model hydroxylation system, and 3. To identify major photothidiazuron metabolites."--Introduction.

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Über den stoffwechsel von Harnstoff-Herbiciden in der ratte. 1. Mitteilung. Monuron und Aresin

Cited by 23 publications

References 9 publications

Metabolism of Monuron in Excised Leaves of Corn and Bean Plants*

Metabolism of Monuron in Excised Leaves of Corn and Bean Plants*

Transcriptomic alterations induced by Monuron in rat and human renal proximal tubule cells in vitro and comparison to rat renal-cortex in vivo

Excretion balance, metabolic fate, and tissue residues of N-Phenyl-N'-1,2,5-Thiadiazol-3-Ylurea (Photothidiazuron) in rats

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