Metobromuron

259.1

259.10

221-301-5

4251089P3L

DTXSID6042157

CRYSTALS FROM CYCLOHEXANE|WHITE CRYSTALS

2928000032

41.6

2.32

White to brown powder

1.5±0.1 g/cm3

95-96 °C

2 °C

1.607

At 20 deg C, in water 0.88 mg/100 g; in acetone more than 100 g/100 g; in ethanol 18.2 g/100 g; in chloroform 62.5 g/100 g

APPROX 4°C

3X10-6 MM HG @ 20 DEG C

Oral-Rat LD50: 2000 mg/kg

Combustion produces toxic bromide and nitrogen oxide gas

145.41 Ų [M+H]+ [CCS Type: TW]

Non-corrosive to metal

UN16483/PG2

2

22-36-20/21/22-11-20/22

16-26-36

YS3325000

Xn,F

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Very stable in neutral, weakly acidic and weakly alkaline media; hydrolyzed by strong acids and bases; the formulated product is stable up to 50 deg C for at least 2 yr.

P305 + P351 + P338

H302-H319-H332

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.

|Warning|H302 (97.44%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P301+P312, P304+P312, P304+P340, P312, P330, and P501|Aggregated GHS information provided by 42 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Avoid skin and eye contact; prevent drifting.

moderately toxic

LD50 RAT FEMALE ORAL 3000 + or - 800 MG/KG|LD50 RAT PERCUTANEOUS > 3000 MG/KG|LD50 RAT MALE ORAL 2700 + or - 300 MG/KG|LD50 RABBIT PERCUTANEOUS > 10200 MG/KG|For more Non-Human Toxicity Values (Complete) data for METOBROMURON (6 total), please visit the HSDB record page.

Metobromuron's production and use as a herbicide(1,2), will result in its release to the environment through various waste streams(SRC).

... 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).

... 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).

Predicted Bioconcentration Factor: 23, based on calculated water solubility; 3, 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).

125.89 L/kg|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).

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).

SURFACE WATER: Metobromuron was qualitatively detected in river water (either a British lowland river or a West German lowland river) by field desorption mass spectrometry(1). Metobromuron was also identified in one out of 211 ponds in Ontario, Canada during the years 1971-1985 at a concentration of 76 ug/l(2). Metobromuron has been qualitatively detected in Dutch surface water resources(3).

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).

METOBROMURON IS ABSORBED BY ROOTS AND LEAVES ...|... Different urea herbicides exhibit different mobilities in plant systems. ... Uptake and translocation of chloroxuron, fluometuron, and metobromuron by bean plants when supplied to nutrient cultures in equal concn (essentially equimolar) and specific radioactivities were studied. Whereas the movement of chloroxuron to aerial parts was found to be restricted under the short-term conditions applied, both fluometuron and metobromuron were rapidly translocated into leaves. However, the two latter cmpd differed strikingly with regard to their distribution pattern within the leaves. In contrast to metobromuron, which was mainly confined to tracheal veins, fluometuron had almost completely moved out into the mesophyll tissues. Although no extensive comparisons of the movement of different urea structures are available at this time, it would appear that their apoplastic distribution in plants is regulated in part by the same physical-chemical phenomena which control the mobility and availability of the cmpd in soil.

METOBROMURON IS METABOLIZED IN PLANTS & ANIMALS BY N-DEMETHYLATION & N-DEMETHOXYLATION, RESPECTIVELY.|... RING-LABELED (14)C-METOBROMURON WAS SUPPLIED TO POTATOES AND CORN SEEDLINGS. ... FOLLOWING METABOLITES ... /WERE IDENTIFIED/: 3-(4-BROMOPHENYL)-1-METHOXYUREA, 3-(4-BROMOPHENYL)-1-METHYLUREA, AND 4-BROMOPHENYLUREA.|METOBROMURON YIELDS 3-(P-BROMOPHENYL)-1-METHYLUREA AND 3-(P-BROMOPHENYL)-1-METHOXYUREA IN TALAROMYCES. /FROM TABLE/|(14)C-Metobromuron was incubated with human embryonic lung (HEL) cells. More than 95% of the label was recovered as unchanged metobromuron. Of four metabolites, three were identified: 3-(4-bromophenyl)-1-methylurea; 4-bromophenylurea; and 3-(4-bromophenyl)-1-methylurea.

... CONSIDERED AS NONHAZARDOUS TO HUMANS ... /SUBSTITUTED UREAS/

3-(p-bromophenyl)-1-methoxy-1-methylurea

50% wettable powder (BASF, Ciba-Geigy). In combination with metolachlor (Galex and Tobacron) or with terbutryn (Ingrater) Ciba-Geigy, 4 lb/gal (400 g/l) flowable (BASF)|Combinations: Igrater 50 WP (metobromuron 25% and terbutryn 25%); Galex 500 EC (metobromuron + metolachlor 1:1 or 2:3)|C 3126|Ciba-3126|For more Formulations/Preparations (Complete) data for METOBROMURON (6 total), please visit the HSDB record page.

Metobromuron is the bromophenyl analog of monuron.|Not marketed in USA.|... /IT/ BECOMES NON-PHYTOTOXIC IN 3 MO AT RECOMMENDED DOSAGES.|Substituted ureas may be hydrolyzed, whereby the end products are carbon dioxide and the corresponding amines. Hydrolysis proceeds under acid as well as alkaline conditions. This reaction is used for the quantitative analysis of active ingredients and/or residues of urea herbicide preparations by determining either the aromatic or the aliphatic amine moiety.

PRODUCT ANALYSIS: A. BY UV SPECTROSCOPY AFTER PURIFICATION BY THIN LAYER CHROMATOGRAPHY. ... PARTICULARS FROM CIBA GEIGY LTD, BASLE. B. TLC METHOD. HANCE, RJ; J CHROMATOGR 44: 419-421 (1969). C. VOSS, G ET AL; ANALYTICAL METHODS FOR PESTICIDES AND PLANT GROWTH REGULATORS, ED SHERMA, J AND ZWEIG, G; ACADEMIC PRESS, NY 7: 569 (1973). RESIDUE: AUTOMATED PROCEDURE FOR DETERMINATION OF UREA HERBICIDE RESIDUES IN SOIL, GUTH, JA & VOSS, G; WEED RESEARCH, 11: 111-119 (1971)|EPA-B Method PMD-MGU "Determination of Metobromuron by GC" Gas Chromatography with Thermal Conductivity Detection with no detection limit reported.|EPA-B Method PMD-MGU "Determination of Metobromuron by IR Spectroscopy" Infrared Spectroscopy with no detection limit reported.|FDA Method 211.1 "Organochlorine Residues (Nonionic) General Methods for Fatty Foods Including Extraction of Fat, Acetonitrile Partition, Florisil Column Cleanup, Partition Chromatographic Cleanup, and Supplemental Cleanup. Gas Chromatography with Electron Capture Detection with no detection limit reported.|For more Analytic Laboratory Methods (Complete) data for METOBROMURON (11 total), please visit the HSDB record page.

Agrochemicals -> Herbicides|Herbicides|Environmental transformation -> Pesticides (parent, predecessor)

Metobromuron has known environmental transformation products that include Desmethoxy-metobromuron, R1 Deymethyl-metobromuron, R3 4-Bromophenylurea, and R4 4-bromoaniline.