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Bromacil

Bromacil structure

Bromacil 

structure
  • CAS No:

    314-40-9

  • Formula:

    C9H13BrN2O2

  • Chemical Name:

    Bromacil

  • Synonyms:

    2,4(1H,3H)-Pyrimidinedione,5-bromo-6-methyl-3-(1-methylpropyl)-;Uracil,5-bromo-3-sec-butyl-6-methyl-;5-Bromo-6-methyl-3-(1-methylpropyl)-2,4(1H,3H)-pyrimidinedione;Bromacil;5-Bromo-3-sec-butyl-6-methyluracil;5-Bromo-6-methyl-3-(1-methyl-n-propyl)uracil;3-sec-Butyl-5-bromo-6-methyluracil;Herbicide 976;Hyvar X;5-Bromo-6-methyl-3-sec-butyluracil;Hyvar X bromacil;5-Bromo-6-methyl-3-(1-methylpropyl)uracil;Hyvarex;(±)-Bromacil;DuPont 976;Uragan;154670-12-9

  • Categories:

    Agrochemicals  >  Herbicides

Description

white to beige crystalline solid Bromacil is a noncombustible colorless, crystalline solid, which may be dissolved in a flammable liquid.


Bromacil appears as colorless to white odorless crystalline solid. Used as an herbicide. Commercially available as a wettable powder or in liquid formulations. (NIOSH, 2016)|COLOURLESS-TO-WHITE CRYSTALS.|Odorless, colorless to white, crystalline solid.|Odorless, colorless to white, crystalline solid. [herbicide] [Note: Commercially available as a wettable powder or in liquid formulations.]


Bromacil appears as colorless to white odorless crystalline solid. Used as an herbicide. Commercially available as a wettable powder or in liquid formulations. (NIOSH, 2016)|5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione is a pyrimidone that is pyrimidine-2,4(1H,3H)-dione substituted by a bromo group at position 5, a butan-2-yl group at position 3 and a methyl group at position 6. It is a pyrimidone and an organobromine compound.

Bromacil Basic Attributes

261.12

261.12

206-245-1

1448

DTXSID4022020|DTXSID4040347|DTXSID8058459

White crystalline solid|White to light-tan crystalline solid|Colorless to white, crystalline solid [Note: Commercially available as a wettable powder or in liquid formulations]

2933599014

Characteristics

49.4

1.88-2.11

White, tan Solid

1.55 g/cm3 @ Temp: 25 °C

157.5-160 °C

Sublimes

1.541

0.71g/L(25 ºC)

0-6°C

Vapour pressure at 25°C: negligible

Oral-Rat LD50: 641 mg/kg; Oral-Mouse LD50: 3040 mg/kg

Combustion produces toxic nitrogen oxides and bromide gases

Dust may cause an explosion. ...

Odorless

Henry's Law constant = 1.29X10-10 atm-cu m/molat 25 °C (est)

pKa = 9.30 at 25 °C

146.95 Ų [M-H]-

Stable in water except under strongly acidic conditions and elevated temperatures|Hydroxyl radical reaction rate constant = 1.94X10-11 cu cm/molec-sec at 25 °C (est)

No rapid reaction with air. No rapid reaction with water.

Amides and Imides

BROMACIL is incompatible with the following: Strong acids (decomposes slowly), oxidizers, heat, sparks, open flames (NIOSH, 2016).

Noncombustible Solid, but may be dissolved in flammable liquids.

Non-corrosive

Safety Information

UN30779/PG3

2

22-36/37/38-50-36

26-61

YQ9100000

Xn,N

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

Stable. Incompatible with strong acids, strong oxidizing agents.

P261-P273-P305 + P351 + P338

H302-H315-H319-H335-H400

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|Bromacil should be incinerated in a unit operating at 850 °C equipped with off gas scrubbing equipment.|Do not contaminate /receiving/ water when cleaning equipment or disposing of equipment washwaters or rinsate. /DuPont Hyvar X Herbicide/|For more Disposal Methods (Complete) data for BROMACIL (7 total), please visit the HSDB record page.

Strong acids (decomposes slowly), oxidizers, heat, sparks, open flames.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Bromacil, EPA 738-R-96-013 (August 1996). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of January 26, 2012: http://www.epa.gov/pesticides/reregistration/status.htm]

Not combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P281, P301+P312, P304+P340, P305+P351+P338, P308+P313, P312, P330, P332+P313, P337+P313, P403+P233, P405, and P501

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]|For more Personal Protective Equipment (PPE) (Complete) data for BROMACIL (6 total), please visit the HSDB record page.|(See protection codes)

Active ingredient and dry formulations are non-flammable; the liquid formulation (HYVAR-XL) is a combustible mixture which should be kept away from heat and open flame.

... Dust may cause an explosion. ...

Bromacil may be ignited by heat or open flame. ... Use dry chemical, carbon dioxide, water spray, or foam extinguishers. ... From a secure, explosion-proof location, use water spray to coll exposed containers. ...|In the event of fire, wear self-contained breathing apparatus. Use personal protective equipment. (On small fires) If area is heavily exposed to fire and if conditions permit, let fire burn itself out since water may increase the area contaminated. Cool containers/tanks with water spray. Dike off area to prevent runoff and contamination of water sources. /DuPont Hyvar X Herbicide/

Under severe dusting conditions, this material may form explosive mixtures in air. /DuPont Hyvar X Herbicide/

Remove all ignition sources. Absorb liquid containing Bromacil in vermiculite, dry sand, earth, or similar material. Collect powdered material in the most convenient and safe manner adn deposit in sealed containers. Ventilate area of spill or leak after clean-up is complete. ...|Sweep up and shovel into suitable containers for disposal. If spill area is on ground near valuable plants or trees, remove top 2 inches of soil after initial cleanup. /DuPont Hyvar X Herbicide/|If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential users/|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential users/

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170. /DuPont Hyvar X Herbicide/|Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 12 hours. /DuPont Hyvar X Herbicide/|/Restricted entry interval (REI) of 12 hours/ PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water, is: Coveralls. Chemical Resistant Gloves made of any waterproof material. Shoes plus socks. /DuPont Hyvar X Herbicide/|Users should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. /DuPont Hyvar X Herbicide/|For more Preventive Measures (Complete) data for BROMACIL (19 total), please visit the HSDB record page.

... Bromacil is mildly irritating to the eye.|Irritates the eyes, skin, upper respiratory system, lungs. Inhalation can cause irritation, coughing and wheezing.

Vacated 1989 OSHA PEL TWA 1 ppm (10 mg/cu m) is still enforced in some states.

Recommended Exposure Limit: 10 Hour Time-Weighted Average: 1 ppm (10 mg/cu m).

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Keep in a well-ventilated room. Separated from strong oxidants and strong acids.

Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly.

The substance is mildly irritating to the eyes, skin and respiratory tract.

PREVENT DISPERSION OF DUST!

Protective gloves.

Wear safety goggles.

SEDIMENT: Bromacil was not detected in 18 Great Lakes Basin sediment samples tested(1).|SOIL: Bromacil was detected in 29 of 822 soil samples collected in the vicinity of 49 agrichemical facilities in Illinois (4 of these handled bromacil) at a mean concentration of 168 ug/kg (range = 32-15,500 ug/kg) (detection limit range of 18-200 ug/kg)(1). The compound was tested for but not detected in silty clay, silty clay loam, and sandy clay loam rice-growing soils from April 1996 to November 1997 in Albufera Natural Park, Valencia, Spain where it is employed as a herbicide on nearby citrus/horticultural crops; detection limit = 0.01 mg/kg(2). Bromacil was detected at0.13 mg/kg (detection limit = 0.02 mg/kg) 61 days post-application in Cuban pineapple fields(3).

Toxicity

moderately toxic

LD50 Rat male oral 5200 mg/kg|LD50 Rat oral (female) 3.998 g/kg|LC50 Rat inhalation >4.8 mg/L air/4 hr|LD50 Rabbit percutaneous >5000 mg/kg|For more Non-Human Toxicity Values (Complete) data for BROMACIL (6 total), please visit the HSDB record page.

/AQUATIC SPECIES/ LC50 values for 30-day old fathead minnows (Pimephales promelas) exposed to bromacil were 185, 183, 182, and 167 mg/L at 24, 48, 96, and 168 hr, respectively. In early life-stage exposures, it was not possible to determine a no effect concentrsation for bromacil, as growth was reduced at the lowest exposure of 1.0 mg/L. Bromacil did not accumulate significantly in fish tissue. Rainbow trout (Salmo gairdneri) injected with radiolabeled bromacil eliminated over 90% of the radioactivity within 24 hr.|/FIELD STUDIES/ The effects of 2.5, 5.0, and 7.5 kg/ha of bromacil on soil microflora were studied in the soil of a plum orchard. A stimulatory effect on the bacterial population and an inhibitory effect on actinomycetes were observed under all the herbicidal treatments up to 60 days from application. Thereafter, the effect leveled off. An inhibitory effect on fungi was noticed with bromacil. In general, the herbicide effect lasted up to 60 days and the microbial status of the soil was not significantly disturbed at low and medium concn.|/FIELD STUDIES/ This study documents the testing of several common herbicides used by the Oregon Department of Transportation in vegetation management. The project assessed the short- and long-term effects of Roundup, Krovar and Oust on periphyton and rainbow trout. The active ingredient in Roundup is glyphosate; Krovar uses bromacil and diuron; and Oust uses sulfometuron-methyl. Short-term (96 hour) exposure tests used actual road shoulder runoff collected after herbicide application, using a simulated rain and a natural rain event. Long-term exposure tests assessed effects of a 14-day exposure using lab-mixed solutions of deionized lab water and herbicides, individually and in mixture. The data showed that the short-term exposure had no statistically significant effects on periphyton. The short-term exposure reduced survivorship of rainbow trout, but the effects were observed both in treated and untreated runoff; thus the toxicity was likely due to other factors. The long-term exposure tests showed that herbicides, especially Krovar and the mixture of three chemicals, reduced periphyton algal biomass

Bromacil's production may result in its release to the environment through various waste streams; its use as a herbicide(1) will result in its direct release to the environment(SRC).|1194805, 575467, and 410957 pounds of bromacil were applied to US citrus crops 1992, 1997, and 2002, respectively(1).

TERRESTRIAL FATE: Based on a classification scheme(1) Koc values ranging from 12(2) to 126(3) indicate that bromacil is expected to have very high to high mobility in soil(SRC). The pKa of bromacil is 9.30(4), indicating that this compound will exist partially in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of bromacil from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-10 atm-cu m/mole(SRC), based upon its vapor pressure, 3.07X10-7 mm Hg(6), and water solubility, 815 mg/L(7). Bromacil is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). The mineralization half-lives in loamy sand and mucky peat soils were estimated to range from 5,429 to 46,200 days(8), indicating that biodegradation is not an important environmental fate process in soil(SRC).|TERRESTRIAL FATE: Bromacil is relatively persistent in soil. The US Dept of Agric's Pesticide Properties Database lists a soil half-life of 60 days for bromacil(1). In a laboratory study using a sandy loam soil and saturated soil conditions, bromacil had an observed half-life of 144-198 days(2). In an apple orchard study where bromacil was applied annually for 6-7 yrs, bromacil had an apparent half-life of approximately 8 months(3). In field plots treated with 4 lb bromacil per acre, bromacil had a half-life of 5 to 6 months(4); identified metabolites included 5-bromo-3-sec-butyl-6-hydroxymethyl uracil, 5-bromo-3-(2-hydroxy-1-methylpropyl)-6-methyluracil, and 5-bromo-3-(3-hydroxy-1-methylpropyl)-6-methyluracil(4). Degradation of 31-65% was observed in six soils after incubation for 6 months under laboratory conditions(5). Laboratory half-lives of 4-5 months were determined for a loam soil at temperatures of 13.2 and 31.2 °C(6); faster degradation occurred at warmer temperatures(6).|TERRESTRIAL FATE: A single application of bromacil at 2 lb ai/acre dissipated with half-lives of 155 days from the upper 10 cm of a bare ground plot of silty clay loam soil in Delaware, and 124 days from the upper 10 cm of a bare ground plot of loam soil located in California(1). Bromacil was detected in the upper 10 cm of the Delaware and California plots through 538 and 415 days posttreatment, respectively(1). In general, bromacil was not detected below the 40 cm soil depth at both test sites. This may have been due to the amount and timing of rainfall and/or irrigation at these sites(1).|At 18 mo after spraying 22.4 kg bromacil/ha on abandoned field sites overgrown mainly by little bluestem (Andropogon scoparius), poverty grass (Danthonia spicata), timothy (Phleum pratense), quackgrass (Agropyron repens), goldenrod (Solidago) and Kentucky bluegrass (Poa pratensis), the max recovery of detectable bromacil residues occurred in the loamy sand, followed by decr amt in the silt loam, silty clay loam, and light silty clay loam. Org matter content, cation-exchange capacity, total nitrogen and sol salt concn were significantly correlated with residue persistence and incr depth in all 4 soils.|For more Environmental Fate (Complete) data for BROMACIL (8 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of bromacil with photochemically-produced hydroxyl radicals has been estimated as 1.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6.6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of bromacil with ozone has been estimated as 1.6X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7.2 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Bromacil was stable to hydrolysis in sterile aqueous pH 5, 7, and 9 buffer solutions, incubated in the dark, at 25 °C for 30 days(3).|Results of photolysis studies indicate that direct photolysis may not be an important environmental fate process for bromacil. Irradiation of aqueous solutions (1-10 ppm) with sunlight or laboratory photoreactors (that simulate sunlight) over a 6-day to 4-month exposure period resulted in only minor loss (<4%) of bromacil(2); 5-bromo-6-methyluracil was identified as a photoproduct(1). Studies looking at the effect of pH on the photolysis of bromacil noted that while bromacil was stable to photoysis in water at pH 5 (half-life of 326 days) and pH 7 (half-life of 102 days), a half-life of 4 to 7 days was reported at pH 9; this was apparently due to a shift in the adsorption spectrum of bromacil once it is ionized(2). Bromacil is stable to photolysis on soil; the irradiation of bromacil on silty clay loam soil for 30 days, 12 hours per day, with a xenon arc lamp resulted in a half-life of 166 days(2). Bromacil has been observed to undergo a rapid photosensitized photolysis in sunlight in the presence of photosensitizers such as methylene blue or riboflavin(2-6). The sensitized degradation rate generally increases with an increase in the pH and in one study using riboflavin and methylene blue, about 10-15% of initial bromacil degraded at pH 7 with 30-min irradiation period(6). At pH 10, 80-90% was degraded; no degradation occurred in the absence of the sensitizers(6).|In a sunlight irradiation study using frozen aqueous solutions of bromacil containing photosensitizers (such as methylene blue, rose bengal, and riboflavin), bromacil was found to rapidly photodegrade under winter conditions. Over an 8-hr exposure period, degradation at pHs 6.8, 8.2 and 9.1 was 10-15%, 70-100% and 100%, respectively. When the frozen samples were covered by ice blocks up to 11 cm thick, the amount of incident light was attenuated, but the photodecomposition reaction rates remained high enough to be of practical value(1).

3.24|The bioconcentration of bromacil in bluegill sunfish (Lepomis macrochirus) was studied over a 28-day period using flow-through conditions(1). Bluegill sunfish exposed to 10.6 ppm bromacil had BCF values for muscle, viscera, carcass, and whole fish of 49, 72, 22, and 26.5, respectively(1). At 1.0 ppm, maximum BCF values were 4.6, 8.3, 2.2, and 2.8 for muscle, viscera, carcass, and whole fish, respectively(1). Depuration was rapid, with >96% of the accumulated residues eliminated from the fish tissues by day 3 of the depuration period. A BCF of 3.2 was measured in fathead minnow(2). A log BCF of 0.35242 in bluegill sunfish exposed for 28 days has also been reported(3), corresponding to a BCF of 2.20(SRC). According to a classification scheme(4), these BCF values suggest that bioconcentration in aquatic organisms is low. [

39.81 L/kg|Bromacil is very mobile in sand, sandy loam, clay loam and silt loam soils; aged bromacil residues are very mobile in silt loam soils(1). Extensive data exists as evidence that bromacil leaches to ground water as a result of normal agricultural use(1). An average Koc value of 23 was determined from experimental values determined in 8 soils and 4 sediments(2). Koc values of 25 to 50 for for Israeli soils(3), 55 to 126(4), 46 to 93 for 7 sandy Florida soils(5), and 76 to 129 for a mucky peat and a loamy sand Oregon soils incubated at temperatures of 4 and 25 °C(6) have been reported. Koc values in sand (FL), sandy loam (CA), clay loam (MD), and silt loam (DE) were 12, 33, 2.3, and 14, respectively(7). According to a classification scheme(8), these Koc values suggest that bromacil is expected to have very high to moderate mobility in soil. In soil column leaching studies, bromacil readily leached from loess and sandy soils, but was retained in organic-rich soils(6). As the pH increased from 3 to 12, less adsorption of bromacil to Ca-montmorillonite was measured(4). In 7 sandy soils, a rainfall of 20-23 cm displaced over 96% of applied bromacil(5). Koc values were slightly higher at lower temperatures(6). Maximum bromacil concentrations of 1.25 ppm were detected in groundwater (depths of 4.5-6 meters) three months after the herbicide was applied to a surface of Lakeland, FL sandy soil bearing scrub vegetation of small oaks and poor grasses(9). The pKa of bromacil is 9.30(10), indicating that this compound will exist partially in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(11). Desorption of bromacil from Cuban soils were reported as 51.98 and 67.00% from a red ferralitic soil and a brown plastic soil, respectively; the specific adsorption constants are 2.89 and 23.9 ug/g, respectively(12). Adsorption coefficients 1.79 and 4.59 for Motupiko topsoil (1-10 cm) and subsoil (40-50 cm), respectively, and 1.57 for Waikiwi topsoil (1-10 cm) have been reported for two Wakefield, Nelson, New Zealand soils. Soil characteristics are as follows: Motupiko silt loam (pH 5.7, 24% sand, 57% silt, 19% clay, 2.4% organic content) Waikiwi silt loam (pH 5.5, 7% sand, 69% silt, 24% clay, 3.9% organic content)(13).|Koc values of 26.3 to 289.1 (average of 41.1) for eight freshwater sediments have been reported(1).|Under saturated-flow conditions, bromacil was considerably more mobile than buthidazole. Because of their high water solubilities, both herbicides were much more mobile than atrazine, prometon, or diuron.|Bromacil concentrations in soil from a Hawaiian pineapple plantation(1).

The Henry's Law constant for bromacil is estimated as 1.3X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 3.07X10-7 mm Hg(1), and water solubility, 815 mg/L(2). This Henry's Law constant indicates that bromacil is expected to be essentially nonvolatile from water and moist soil surfaces(3). In a volatilization test, bromacil was held in an air circulation oven at 120 °F for 2 weeks(3); losses were less than 0.1% per week(4). Bromacil is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1). Volatilization screening simulations from soil indicate that volatilization from soil (after incorporation to 1-10 cm) is slow(5).

GROUNDWATER: According to an interim report of the USEPA's Groundwater Data Base, bromacil has been detected in groundwater samples from NY and CA at a max concentration of 22 ppb and a median concentration (of positive detections) of 9 ppb(1). Monitoring analyses of 10,929 wells in CA during 1975 to 1989 detected bromacil (detection limit and concentrations not reported) in 4 wells(2). As of June 1984, bromacil was not detected (detection limit not reported) in a Wisconsin monitoring study that had analyzed 1508 samples from 358 wells(3). A bromacil ground water concentration of 300 ppb has been reported for an unnamed FL site(4). As of May 1995, 899 of 2837 wells in Florida's Pesticide Contamination Monitoring System contained bromacil at concentrations less than 90 ppb while 57 wells had concentrations greater than 90 ppb; 679 of the wells with detections were from the citrus-growing area in the Central Ridge(5). 282 positive detections from 6800 well samples collected from 12 different counties were reported in California(5). The California Department of Pesticide Regulation reported bromacil in 90 wells (total wells unreported), samples collected between 1975 and 1991, at a maximum concentration of 15 ug/L(6). Bromacil was detected, not quantified in 5%, 6%, and 6% of samples from an orchard, row crops, and public supply well networks, respectively; groundwater monitoring of 72 wells was conducted in the Central Columbia Plateau, WA between 1193 and 2003 by the USGS(7).|GROUNDWATER: Bromacil concentrations of 30 to 147 ug/L have been reported for upper ground water samples collected in West Germany(2); concentrations of <0.1-1.8 ug/L were reported for water samples from bore holes (15-40 m deep) in three provinces in the Netherlands(1). In a 1979-1984 analysis of 7 wells in Ontario, Canada that were in the vicinity of bromacil herbicide use, bromacil was detected (detection limit 0.1 ug/L) in only one well(2). Bromacil was detected not quantified in 95 of 1712 groundwater dominated samples collected from the Federal Republic of Germany between 1986 and 1991(3). The compound was detected at concentration range of 0.13 to 5.0 ug/L in 12 groundwater samples from 6 wells at a former military base in Germany, sampled in 2002(4). Bromacil concentrations in 94 wells in the Gaza Strip sampled between November 2000 and March 2002 were below the detection limit of 25 ng/L(5). [|DRINKING WATER: The National Drinking Water Contaminant Occurrence Database reports that 144 of 11,438 water samples collected in 47 states/territories, but not necessarily associated with a public drinking water supply, contained bromacil at an average concentration of 0.0769 ug/L (range of 0 to 3 ug/L)(1). Samples from a drinking water treatment plant located in a heavily populated, highly urbanized US drainage basin tested negative for bromacil; detection limit 0.5 ug/L(2).|SURFACE WATER: The South Florida Water Management District summarized bromacil detections in samples collected every 2 to 3 months from 27 surface water sites within the District from November 1988 through November 1993. 56 of 810 samples contained bromacil at concentrations of 0.002 to 0.25 ppb (maximum of 14 ppb)(1). 3 of 84 surface water samples collected from 6 Louisiana water districts in 1992 contained bromacil (detection limit not reported) at concentrations of 0.4 to 1.73 ppb(1). 12 of 48 surface water samples collected from 8 locations in 5 Louisiana water districts in May-October 1994 contained bromacil (detection limit not reported) at concentrations of 0.13 to 2.63 ppb(1). The compound was detection frequency of 5% of 211 observations with a maximum concentration of 0.06 ug/L from an urban stream in Marietta, GA, one of 8 urban stream areas monitored during 1993 and 1994; detection limit = 0.05 ug/L(2). Bromacil was present at a median concentration of 0.750 ug/L with a detection frequency of 14% in a survey of north-central and northwestern Arkansas streams conducted in March, April and August, 2004; reporting limit = 0.5 ug/L(3). Bromacil was detected in all 164 US Great Lakes Basin Stream tested at a minimum concentration of 0.001 ug/L, maximum of 1.63 ug/L Great Lakes Basin sediment samples tested. Its detection in 84 samples from Canadian waters and the Great Lakes is 14.3% detection, mean concentration of 0.9650 ug/L(4). It was observed that bromacil concentrations in urban Iowa streams sampled during 2001 varied at high-flow, normal-flow and low flow with corresponding concentrations of 0.09, 0.14, and 0.39 ug/L reported(5). The Kisco River and the Middle Branch of the Cronton River, south-eastern New York State were monitored from May 200 through February 2001; bromacil was detected in 4% of samples with an estimated maximum concentration of 0.17 ug/L occurring during the month of November (detection limit = 0.081 ug/L)(6).|SURFACE WATER: Bromacil was detected not quantified in 9 of 1019 surface water samples collected from the Federal Republic of Germany between 1986 and 1991(1).

Bromacil was detected in an unreported number of samples at unspecified concentrations in the FDA's 1996 Market Basket Survey where a total of 10,374 samples of domestically produced food and imported food from 92 countries were analyzed for pesticide residues(1). Results for bromacil testing in subsequent Market Basket Surveys were as follows: 2004 - 2,832 domestic and 5,073 import samples collected and analyzed; tested for, not detected; 2005 - 2,638 domestic and 5,286 import samples collected and analyzed; tested for, not detected; 2006 - 1,392 domestic samples from 41 States and Puerto Rico and 4,317 import samples from 87 countries were analyzed; tested for, not detected(2).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of bromacil is 1 to 99; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 4,372 workers (63 of these were female) were potentially exposed to bromacil in the US(1). The NOES Survey does not include farm workers. Occupational exposure to bromacil may occur through inhalation and dermal contact with this compound at workplaces where bromacil is produced or used. Bromacil is widely detected in groundwater, particularly in agricultural areas where this compound has been used. The general population may be exposed to bromacil via ingestion of drinking water, particularly from wells near agricultural areas(SRC).

Drug Information

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)

Bromacil is absorbed from the GI tract and appears to be excreted primarily in the urine.|Bromacil was absorbed readily from the gastrointestinal tract ... Radiolabel was found in all tissues examined, but there was no evidence of accumulation.|The major route of elimination was via the urine following all dosing schedules except the multiple low dose in males where urine and fecal elimination were approximately equal.|When herbicide concentration in feed of cows was 5 and 30 ppm, secretion of intact compound in milk reached concentrations of 0.019 and 0.13 ppm, respectively. Bromacil was absent in urine and feces samples.|For more Absorption, Distribution and Excretion (Complete) data for BROMACIL (6 total), please visit the HSDB record page.

Metabolic studies were conducted with rats given single (low and high) and multiple (low) doses of radiolabelled bromacil. ... Bromacil was absorbed readily from the gastrointestinal tract, extensively metabolized (primarily by hydroxylation at the 6-methyl position and on the sec-butyl moiety), and rapidly excreted. The hydroxylated metabolites were eliminated as glucuronide conjugates. ... The major metabolite of bromacil in the urine of rats was 5-bromo-6-hydroxymethyl-3-sec-butyluracil. Trace levels of the parent compound and two other (unidentified) metabolites were excreted in the urine.|Male rats ... maintained for 1 month on diet ... /of/ 1250 ppm of bromacil. Urine was collected ... and analyzed. ... Metabolites ... isolated: 5-bromo-3-sec-butyl-6-hydroxymethyluracil; 5-bromo-3-(2-hydroxy-1-methyl-propyl)-6-methyluracil; 5-bromo-3-(2-hydroxy-1-methylpropyl)-6-hydroxymethyluracil; 3-sec-butyl-6-hydroxymethyluracil; 5-bromo-3-(3-hydroxy-1-methylpropyl)-6-methyluracil; 3-sec-butyl-6-methyluracil; and unidentified bromine-containing compound of molecular wt 339.|Bromacil ... /is/ metabolized in rodents by side-chain oxidation.

0.05 Days

BROMACIL HAS BEEN SHOWN TO BE A POTENT & SPECIFIC INHIBITOR OF PHOTOSYNTHESIS.

Exposure Routes: inhalation, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin, upper respiratory system Target Organs: Eyes, skin, respiratory system, thyroid (NIOSH, 2016)

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)


Fresh air, rest.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Skin decontamination: Skin contamination should he treated promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with large amounts of clean water. If dermal or ocular irritation persists, medical attention should be, obtained without delay. /Herbicides/|Gastrointestinal decontamination: Ingestion of these herbicides are likely to be followed by vomiting and diarrhea due to their irritant properties. Management depends on: (1) the best estimate of the quantity ingested, (2) time elapsed since ingestion, and (3) the clinical status of the subject. Activated charcoal is probably effective in limiting irritant effects and reducing absorption of most or all of these herbicides. Aluminum hydroxide antacids may be useful in neutralizing the irritant actions of more acidic agents. Sorbitol should be given to induce catharsis if bowel sounds are present and if diarrhea has not already commenced. Dehydration and electrolyte may be severe enough to require oral or intravenous fluids. There are no specific antidotes for poisoning by these herbicides. In the case of suicidal ingestions, particularly, the possibility must always be kept in mind that multiple toxic substances may have been swallowed. If large amounts of herbicide have been ingested and the patient is seen an hour of the ingestion, gastrointestinal decontamination should be considered. If the amount of ingested herbicides was small, if effective emesis has already occurred, or if treatment is delayed, administer activated charcoal and sorbitol mouth. /Herbicides/|Intravenous fluids: If serious dehydration and electrolyte depletion have occurred as a result of vomiting and diarrhea, monitor blood electrolytes and fluid balance and administer intravenous infusions of glucose, normal saline, Ringer's solution, or Ringer's lactate to restore extracellular fluid volume and electrolytes. Follow this with oral nutrients as soon as fluids can be retained. /Herbicides/|/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|For more Antidote and Emergency Treatment (Complete) data for BROMACIL (6 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ ... Bromacil poisoning was characterized by vomiting, gastritis, and tongue numbness.|/EPIDEMIOLOGY STUDIES/ A cohort mortality study was undertaken of foresty workers at a public electrical utility who had worked for six months or more during 1950-82 and who were routinely exposed to herbicides including phenoxy acids. A total of 1222 men with 25,274 years at risk experienced 80 deaths. Ascertainment of vital state at the end of follow up was 95.5%. The male population of the province (Ontario) was used as the reference group. Overall, no excess mortality was found in this cohort relative to the reference population. A statistically significant increase in deaths occurred, however, due to suicide (SMR = 210, 95% confidence interval, 95% CII 105-376) for the cohort as a whole. No deaths were seen due to cancers such as soft tissue sarcoma and non-Hodgkin's lymphoma that have been cited by other authors as being associated with exposure to phenoxy acid herbicides. Although the cohort is not large, the absence of deaths due to these cancers is consistent with findings from other studies with sufficient numbers to allow examination of specific risks. The cohort is still young, however, and at the end of follow up most had not reached an age when increased incidence of cancer would normally be expected. /Phenoxy acids/

bromacil

The substance can be absorbed into the body by ingestion.|inhalation, ingestion, skin and/or eye contact

irritation eyes, skin, upper respiratory system; In Animals: thyroid injury


Cough.


Redness.


Redness. Pain.

Eyes, skin, respiratory system, thyroid

Bromacil Use and Manufacturing

Methods of Manufacturing

Bromacil is produced by reaction of isopropyl isocyanate with methyl 3-aminocrotonate, followed by cyclization in sodium hydroxide at elevated temperature, and bromination in acetic acid.|BROMINATION OF 3-SEC-BUTYL-6-METHYLURACIL|Bromacil is manufactured by the reaction of phosgene and ammonia with sec-butylamine to produce sec-butylurea, which reacts with ethylacetoacetate to produce 3-sec-butyl-6-methyluracil, which is then brominated to produce bromacil.

Uses

Herbicide.

Production

(1972) 1.82X10+9 G|(1974) 6.4X10+9 G (EST)|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3214]

APPROX 77% FOR INDUSTRIAL/COMMERCIAL USE AS AN HERBICIDE; APPROX 13% FOR AGRICULTURAL USE AS AN HERBICIDE; AND APPROX 10% FOR GOVERNMENT AGENCY USE AS AN HERBICIDE (1972)|In 1992, 1,194,805 pounds of bromacil were applied to citrus crops in the US.

USEPA/OPP Pesticide Code 012301; Trade Names: Hyvar X; Weed-Broom; Cyanogan; Uragan; Borea; Borocil 1V; Herbicide 976; Hyvar X bromoacil; Hyvar X weed killer; Hyvarex; Krovar II; Nalkil; Urox B.|Granular, liquid, water soluble liquid, and wettable powder.|Premix Partners: Diuron; Sodium chlorate; Sodium metaborate.|Hyvar X Bromacil (wettable powder: 80% ai), Hyvar X-WS Bromacil (water sol powder: 50% ai), and Hyvar X-L Bromacil (liq concn: 3 lb ai/gal)|For more Formulations/Preparations (Complete) data for BROMACIL (46 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies bromacil as unlikely to present an acute hazard in normal use; Main Use: herbicide.|Water-soluble formulations are incompatible with ammonium sulfamate and liquid preparations of amitrole. Herbicides containing soluble calcium salts form precipitates when used with water-soluble formulations of bromacil.|Substitute approved by EPA for some uses of 2,4,5-T

Method: USGS-NWQL O-3106-93; Procedure: gas chromatography; Analyte: bromacil; Matrix: water and mixtures of water-suspended sediment; Detection Limit: 0.2 ug/L.|Method: USGS-NWQL O-2060-01; Procedure: high performance liquid chromatography-mass spectrometry; Analyte: bromacil; Matrix: water; Detection Limit: 0.0163 ug/L.|Method: USGS-NWQL O-1433-01; Procedure: gas chromatography/mass spectrometry; Analyte: bromacil; Matrix: filtered wastewater and natural-water samples; Detection Limit: 0.1 ug/L.|Method: USGS-NWQL O-1131-95; Procedure: high performance liquid chromatography; Analyte: bromacil; Matrix: natural water; Detection Limit: 0.011 ug/L.|For more Analytic Laboratory Methods (Complete) data for BROMACIL (19 total), please visit the HSDB record page.

Residues of bromacil are extracted from animal tissues with 1% sodium hydroxide solution /and analyzsed/ by using gas chromatographic with microcoulometric detection. Average recoveries ranged from 85 to 115%. Detection limit was 0.04 ppm (25 g sample).

Agrochemicals -> Herbicides|Herbicides|HERBICIDES

Computed Properties

Molecular Weight:261.12
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:260.01604
Monoisotopic Mass:260.01604
Topological Polar Surface Area:49.4
Heavy Atom Count:14
Complexity:312
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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