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Metobromuron
c-3126 · C 3126 · PATORAN · PATTONEX · CIBA 3126 · Patoran FL · Metbromuron · monobromuron
Identifikatoren & physikalische Daten
| CAS No. | 3060-89-7 |
|---|---|
| Summenformel | C9H11BrN2O2 |
| Durchschnittliche Molmasse | 259,1 g/mol |
| Monoisotopische Masse | 258,00039 g/mol |
| SMILES | CON(C)C(=O)Nc1ccc(Br)cc1 |
| InChIKey | WLFDQEVORAMCIM-UHFFFAOYSA-N |
| PubChem CID | 18290 |
| ChEMBL | CHEMBL1356637 |
| ChEBI | CHEBI:81964 |
| EC No. | 221-301-5 |
| DTXSID | DTXSID6042157 |
| Lokaler Name | Metobromuron |
Chemische & physikalische Eigenschaften
| XLogP | 2,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 41,6 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 193 |
| SpringerMaterials Properties | Fusion temperature |
| Pestizide | HerbicidesActive substance -> EU Pesticides database: ApprovedPesticides -> Herbicides, Urea DerivativeEnvironmental transformation -> Pesticides (parent, predecessor)Pesticide (Metobromuron) -> USDA PDB |
| LogP (Verteilungskoeffizient) | 2.41 |
| Color/Form | CRYSTALS FROM CYCLOHEXANEWHITE CRYSTALS |
| Löslichkeit | IN WATER: 320 PPM AT 20 °CSOL IN METHANOL, ETHANOL, ACETONE, CHLOROFORMAt 20 °C, in water 0.88 mg/100 gin acetone more than 100 g/100 gin ethanol 18.2 g/100 gin chloroform 62.5 g/100 g333.8mg/L(20 ºC) |
| Corrosivity | Non-corrosive to metal |
| Schmelzpunkt | 95-96 °C95-96° |
| Dampfdruck | 0.000003 [mmHg]3X10-6 MM HG @ 20 °C |
| Physical Description | Colorless solid[Hawley] White solid[HSDB] |
| Stability/Shelf Life | Very stable in neutral, weakly acidic and weakly alkaline mediahydrolyzed by strong acids and basesthe formulated product is stable up to 50 °C for at least 2 yr. |
| Collision Cross Section | 147.7 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID6042157]145.41 Ų [M+H]+ [CCS Type: TW] |
| Dichte | 1.6027 (rough estimate) |
| Brechungsindex | 1.6070 (estimate) |
| Flammpunkt | 2 °C |
| Lagerbedingungen | APPROX 4°C |
| pKa (Säurekonstante) | 12.80±0.70(Predicted) |
| Farbe | Crystals from cyclohexane |
| BRN | 2103964 |
| Henry-Konstante | 3.2×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C9H11BrN2O2/c1-12(14-2)9(13)11-8-5-3-7(10)4-6-8/h3-6H,1-2H3,(H,11,13) |
| InChIKey | WLFDQEVORAMCIM-UHFFFAOYSA-N |
| SMILES | CON(C)C(=O)Nc1ccc(Br)cc1 |
| LogP (Verteilungskoeffizient) | 2.380 |
| CAS Datenbank | 3060-89-7(CAS DataBase Reference) |
| NIST chemische Informationen | N'-(4-Bromophenyl)-N-methoxy-N-methylurea(3060-89-7) |
| EPA chemische Informationen | Metobromuron (3060-89-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 5.1% (3 of 59) of reports.WarningH302 (93.2%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P261, P264, P270, P271, P273, P280, P301+P317, P304+P340, P317, P318, P319, P330, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 59 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Regulation (EC) No 396/2005 (amended)2011/253/EU, Reg. (EC) No 2076/2002, Reg. (EU) 2018/155, Reg. (EU) 2024/2781, Reg. (EU) No 890/2014 |
| Gefahrenübersicht | Urea-derived herbicides have low toxicity in animal feeding studiesMay induce methemoglobinemia[HSDB] Systemic toxicity unlikely unless large amounts ingested[EPA Pesticides, p. 122] An eye irritantHarmful by ingestion and inhalation[Sigma-Aldrich MSDS] |
| FIFRA-Anforderungen | A tolerance is established for residues of the herbicide metobromuron, (N'-(4-bromophenyl)-N-methoxy-N-methylurea) in or on the raw agricultural commodity, potatoes. |
| Hazard Classes and Categories | Acute Tox. 4 (93.2%) |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.Hydrolysis is not recomended as a disposal procedure because of the generation of the toxic products, 3,4-dichloroaniline and dimethylamine.Metobromuron should be incinerated in a unit operating at 850 °C with off gas scrubbing equipment. Recommendable method: Incineration. |
| Preventive Measures | Avoid skin and eye contactprevent drifting. |
| Allowable Tolerances | A tolerance of 0.2 ppm is established for residues of the herbicide metobromuron, (N'-(4-bromophenyl)-N-methoxy-N-methylurea) in or on the raw agricultural commodity, potatoes. |
| Ökotoxizitätswerte | LC50 TROUT 71-85 PPM/96 HR EXPOSURE /CONDITIONS OF BIOASSAY NOT SPECIFIED/LC50 GOLDFISH 71-85 PPM/96 HR EXPOSURE /CONDITIONS OF BIOASSAY NOT SPECIFIED/LC50 BLUEGILL 71-85 PPM/96 HR EXPOSURE /CONDITIONS OF BIOASSAY NOT SPECIFIED/LD50 BEE MORE THAN 160 UG/BEE /CONDITIONS OF BIOASSAY NOT SPECIFIED/ |
| Umweltverhalten | ... TERRESTRIAL FATE: METOBROMURON DISAPPEARED AT A FASTER RATE THAN FLUOMETURON /FROM SOIL/.TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 470(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(3), indicates that metobromuron should have moderate mobility in soil(SRC). Volatilization of metobromuron should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 3.1X10-9 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(4) and water solubility(5), or from dry soil surfaces(SRC) based on an experimental vapor pressure of 3X10-6 mm Hg(4). Metobromuron may photolyze on soil surfaces(SRC) according to two studies(6,7). A variety of pure culture biodegradation studies, including biodegradation in plants, algae, and fungi(8-11), suggest that metobromuron may biodegrade in water(SRC).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 470(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(1), indicates that metobromuron may adsorb to suspended solids and sediment(SRC) in the water. Metobromuron will be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 3.1X10-9 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(3) and water solubility(4). An estimated BCF value of 38(1,SRC), from an experimental log Kow(2), suggests that metobromuron may bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5). A variety of pure culture biodegradation studies, including biodegradation in plants, algae, and fungi(6-9), suggest that metobromuron may biodegrade in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), metobromuron, which has an experimental vapor pressure of 3X10-6 mm Hg at 25 °C(2), will exist as a vapor in the ambient atmosphere. Vapor-phase metobromuron is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be about 28 hours(3,SRC). Particulate-phase metobromuron may be physically removed from the air by wet and dry deposition(SRC). |
| Lebensmitteluntersuchungswerte | Metobromuron was detected once in radish at a concentration of 0.04 ug/g, in a 10 yr accumulated frequency survey of 234 ready-to-eat foods tested 37 times each(1). |
| Unerwünschte Wirkungen | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| Soil Adsorption/Mobility | Metobromuron /is/ ... moderately mobile in the soil ... Movement of the cmpd also decr as organic matter content of the soil incr, and in turn the herbicidal activity of the phenylureas decr as the cmpd are bound to the soil organic matter.Soil adsorption coefficient: 60 (experimental)180 (calculated). /From table/The Koc of metobromuron is estimated as approximately 470(SRC), using an experimental log Kow of 2.38(1) and a regression-derived equation(2,SRC). The Koc for metobromuron has also been experimentally determined to be 104.7(3). For soil with organic carbon levels of 0.58-2.3%, metobromuron had an average experimental Koc value of 60(4). The average Koc value from eight soils of Czechoslovakia with organic matter contents ranging from 0.1-4.6% was 490(5). According to a recommended classification scheme(6), this estimated Koc value suggests that metobromuron should have medium to high mobility in soil(SRC). |
| Human Toxicity Excerpts | ... CONSIDERED AS NONHAZARDOUS TO HUMANS ... /SUBSTITUTED UREAS/ |
| Artificial Pollution Sources | Metobromuron's production and use as a herbicide(1,2), will result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | ... The two fungi, Talaromyces wortmanii and Fusarium oxysporum metabolized (14)C-labeled metobromuron, whereas a Bacillus sp and the alga Chlorella vulgaris were unable to degrade the same herbicide.Talaromyces wortmanii and Fusarium oxyporum degrade metobromuron by N-demethoxylation./Metobromuron was incubated/ with soil-enrichment solutions and pure cultures of active microbial isolates. ... It was shown that in the presence of the fungus, Fusarium oxysporum, halogen ions were released into the culture medium from ... metobromuron.The degradation of metobromuron by a linuron-inducible enzyme produced by Bascillus sphaericus had a specific activity of the cell-free extract of 0.18X10-3 units/mg of protein and produced 4-bromoaniline(1). The fungus Rhizoctonia solani was able to transform metobromuron by 70% after 6 days(2). In plants, the methyl and methoxy groups are split off and the urea moiety is further degrade to 4-bromoaniline(3). Presumably there is simultaneous ring hydroxylation and fission(3). Two fungi, Talaromyces wortmanii and Fusarium oxysporum metabolized 14C-labeled metobromuron, whereas neither Bascillus sphaericus nor the alga Chlorella vulgaris were able to degrade metobromuron(4). |
| Environmental Bioconcentration | Predicted Bioconcentration Factor: 23, based on calculated water solubility3, based on calculated soil adsorption coefficient.An estimated BCF value of 38 was calculated for metobromuron(SRC), using an experimental log Kow of 2.38(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms may be moderate, not high(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for metobromuron is estimated as 3.1X10-9 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 3X10-6 mm Hg(1), and water solubility, 330 mg/l(2). This value indicates that metobromuron will be essentially nonvolatile from water surfaces(3,SRC). Metobromuron's vapor pressure(1) and Henry's Law constant(1,2,SRC) indicate that volatilization from dry and moist soil surfaces should not occur(SRC). |
| Non-Human Toxicity Excerpts | In 2-yr feeding trials rats receiving 250 mg/kg diet and dogs 100 mg/kg diet were unaffected. It is of low toxicity to wildlife.Fatally poisoned animals exhibited adipsia, dyspnea, hypothermia, and anuria. Death occurred within two days and was due to cardiac or respiratory failure. In survivors, recovery was accompanied by diuresis, alkalinuria, and /less frequently/ hematuria, glycosuria, or proteinuria. Clinical signs of poisoning disappeared in 3 to 4 days. Autopsies of fatally poisoned rats revealed gastroenteritis, fatty necrosis of the liver, renal, and splenic pallor, and degenerative changes in kidneys, muscle, salivary glands, and testes. Capillary venous congestion in brain, heart, and lung accompanied by signs of a stress reaction in adrenal, spleen, and thymus. /Monuron/The effect of substituted urea herbicides on rat hepatic microsomal epoxide-hydroxylase activity was studied in-vitro. Male Wistar-rats were given 16.7% of the median lethal dose (LD50) of diuron, linuron, chlorbromuron, chlortoluron, metoxuron, monolinuron, metobromuron or isoproturon on 3 consecutive days by oral gavage. The animals were killed 24 hr after the last dose and the livers were removed. Epoxide-hydroxylase activity was determined by a HPLC assay using styrene-oxide as the substrate and styrene-glycol as the standard. Indices of induction were calculated. The experimental values of epoxide-hydrolase activity in nmoles/min/mg protein were: control, 7.2diuron, 13.8linuron, 12.1chlorbromuron, 13.2chlortoluron, 21.8metoxuron, 16.1monolinuron, 12.6metobromuron, 10.6and isoproturon, 29.5. The indices of induction were: diuron, 0.37linuron, 0.25chlorbromuron, 0.29chlortoluron, 0.26metoxuron, 0.53monolinuron, 0.43metobromuron, 0.37and isoproturon, 0.82. The authors note that the herbicides that have two halogen substituents on the phenyl moiety have higher molar induction that those which have only a single halogen substituent or none.The effects of eight structurally related, substituted urea herbicides on the hepatic cytochrome-P-450 dependent monooxygenase enzyme were investigated in rats. Male Wistar-rats were given one sixth the median lethal dose of herbicides by gavage on 3 consecutive days. The doses admin were 57 mg/ml diuron, 67 mg/ml linuron, 83 mg/ml chlorbromuron, 166 mg/ml chlortoluron, 53 mg/ml metoxuron, 38 mg/ml monolinuron, 33 mg/ml metobromuron and 77 mg/ml isoproturon. Animals were sacrificed 24 hr after the last treatment with the herbicides. Cytochrome-P-450 and cytochrome-b-5 content of liver microsomes were determined by difference spectrophotometry. Chlortoluron was the only cmpd that increased the relative liver weight to body weight while monolinuron decreased the value. Diuron, linuron, and chlorbromuron increased cytochrome-P-450 content by approx 50 percentthe other herbicides caused smaller induction. Metoxuron was the only cmpd that had no effect on cytochrome-P-450 content. Cytochrome-b-5 content of microsomes was changed within a 20 percent range and only linuron enhanced it significantly. Diuron, linuron, chlorbromuron, and chlortoluron were the most effective inducers of benzo(a)pyrene monooxygenase, causing a 3.5 to 8 fold inductionmonolinuron and metobromuron induced a 2 fold incr whereas metoxuron and isoproturon had no effect. Among aldrin-epoxidase activities the greatest induction was obtained with isoproturon. Linuron and chlortoluron were less effective, and no significant changes was obtained with the other five cmpds. Diuron, chlorbromuron, chlortoluron, and isoproturon enhanced uridine-diphosphate-glucuronyltransferase and glutathione-S-transferase activities. The authors conclude that the number of halogen substituents on the phenyl group of substituted urea cmpds exert a strong influence on the induction of monoxygenases.Toxic doses /in rats/ caused ataxia, drowsiness, hyporeflexia, pallor, and tachypnea, progressing to dacryorrhea, aciduria, diarrhea, epistaxis, hyperreflexia, and irritability. /Monuron/ |
| Environmental Abiotic Degradation | ... METOBROMURON IS CONVERTED TO CORRESPONDING PHENOL BY PHOTOLYTIC REPLACEMENT OF BR ...The rate constant for the vapor-phase reaction of metobromuron with photochemically produced hydroxyl radicals has been estimated as 1.38X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 29 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Metobromuron, in a 225 mg/l aqueous solution, was irradiated with sunlight for a 17-day period in late summer resulted in a mixture containing 80% unchanged metobromuron and 15% 3-(p-hydroxyphenyl)-1-methoxy-1-methylurea(2). The remaining material consisted of at least 3 compounds: 3-(p-bromophenyl)-1-methylurea, p-bromophenylurea, and an unidentified material or materials(2). After irradiating for 135 minutes with a 300-nm sunlight lamp in water, and two surfactants TMN-10 and X-100, at a concentration of 100 mg/l, metobromuron degraded 59, 53, and 60%(3). |
| Wassergefährdungsklasse (WGK) | 2 |
| UN-Transportnummer | UN 1648 3/PG 2 |
| Zollcode | 29280000 |
| RTECS-Nr. | YS3325000 |
| R-Sätze (R) | 22-36-20/21/22-11-20/22 |
| Toxizität | LD50 orally in rats: 3875 mg/kg (Novakova, Dinoeva) |
| Gefahrensymbole | Xn,F |
| Sicherheitshinweise (S) | 16-26-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 3060-89-7(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 InhalationAcute Tox. 4 Oral |
Anwendungen & Verwendung
Verwenden
Metobromuron is a preemergence herbicide.