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Bromacil
Rout · Borea · hibor · Hyvar · uroxb · Bromax · Nalkil · Uragon
Identifikatoren & physikalische Daten
| CAS No. | 314-40-9 |
|---|---|
| Summenformel | C9H13BrN2O2 |
| Durchschnittliche Molmasse | 261,12 g/mol |
| Monoisotopische Masse | 260,01603976 g/mol |
| SMILES | CCC(C)n1c(=O)[nH]c(C)c(Br)c1=O |
| InChIKey | CTSLUCNDVMMDHG-UHFFFAOYSA-N |
| PubChem CID | 9411 |
| ChEMBL | CHEMBL1877125 |
| ChEBI | CHEBI:83658 |
| EC No. | 206-245-1 |
| DTXSID | DTXSID4022020 |
| Lokaler Name | Bromacil |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 49,4 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 312 |
| Pestizide | HerbicidesActive substance -> EU Pesticides database: Not approvedPesticides -> Herbicides, OtherPesticide (Bromacil) -> USDA PDBPesticide and(or) Waste-water effluent contaminant |
| LogP (Verteilungskoeffizient) | log Kow = 2.111.88-2.111.33 |
| Geruch | Odorless |
| Dichte | 1.55 (NIOSH, 2024) - Denser than waterwill sink1.55 g/cu cm at 25 °C1.55 g/cm³ |
| Color/Form | White crystalline solidWhite to light-tan crystalline solidColorless to white, crystalline solid [Note: Commercially available as a wettable powder or in liquid formulations] |
| Löslichkeit | 0.08 % at 77 °F (NIOSH, 2024)SPARINGLY SOL IN HYDROCARBONSModerately soluble in strong aqueous basesSoluble in 3% aqueous NaOHIn n-hexane 0.023 toluene 3.0, acetonitrile 4.65, acetone 11.4, methylene chloride 12.0 (all in g/100 mL, 20 °C)For more Solubility (Complete) data for BROMACIL (6 total), please visit the HSDB record page.DMSO: Soluble,Methanol: Slightly Soluble0.71g/L(25 ºC) |
| Corrosivity | Non-corrosive |
| Siedepunkt | Sublimes (NIOSH, 2024) |
| Decomposition | ... Decomposes slowly in strong acids.When heated to decomp it emits very toxic fumes of /hydrogen bromide and nitrogen oxides/. |
| Schmelzpunkt | 317 °F (Sublimes) (NIOSH, 2024)158 °C158-160 °C317 °F (sublimes)157-160°C |
| Dampfdruck | 0.0008 mmHg at 212 °F (NIOSH, 2024)0.00000031 [mmHg]4.1X10-2 mPa /3.07X10-7 mm Hg/ at 25 °CVapor pressure at 25 °C: negligible0.0008 mmHg at 212 °F(212 °F): 0.0008 mmHg0Pa at 25℃ |
| Physical Description | Bromacil appears as colorless to white odorless crystalline solid. Used as an herbicide. Commercially available as a wettable powder or in liquid formulations. (NIOSH, 2024)Odorless, colorless to white, crystalline solid. [herbicide] [Note: Commercially available as a wettable powder or in liquid formulations.][NIOSH]COLOURLESS-TO-WHITE CRYSTALS.Odorless, colorless to white, crystalline solid. |
| Brechungsindex | 1.5410 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| pKa (Säurekonstante) | 8.79±0.40(Predicted) |
| Aggregatzustand | Solid |
| Farbe | White, tan |
| Merck | 13,1365 |
| BRN | 6804755 |
| Henry-Konstante | 7.6×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong acids, strong oxidizing agents. |
| Hauptanwendungen | agricultureenvironmental |
| InChI | 1S/C9H13BrN2O2/c1-4-5(2)12-8(13)7(10)6(3)11-9(12)14/h5H,4H2,1-3H3,(H,11,14) |
| InChIKey | CTSLUCNDVMMDHG-UHFFFAOYSA-N |
| SMILES | CCC(C)N1C(=O)NC(C)=C(Br)C1=O |
| LogP (Verteilungskoeffizient) | 1.71 at 23℃ |
| CAS Datenbank | 314-40-9(CAS DataBase Reference) |
| NIST chemische Informationen | Bromacil(314-40-9) |
| EPA chemische Informationen | Bromacil (314-40-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 2.5% (3 of 121) of reports.WarningH302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 121 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Danger |
|---|---|
| Regulatorische Informationen | Status: Active Update: 17-08-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26639Bromacil: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Weitere Sicherheitsinformationen | IMAP assessments - 2,4(1H,3H)-Pyrimidinedione, 5-bromo-6-methyl-3-(1-methylpropyl)-: Human health tier I assessment |
| Brandgefahren | Not combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. |
| Brandpotenzial | Active ingredient and dry formulations are non-flammablethe liquid formulation (HYVAR-XL) is a combustible mixture which should be kept away from heat and open flame. |
| Gesundheitsgefahren | Excerpt from NIOSH Pocket Guide for Bromacil: |
| Gefahrenübersicht | Bromacil is classified as practically nontoxic in dry form, moderately toxic in liquid form. [EXTOXNET] |
| Reaktive Gruppe | Amides and Imides |
| Special Reports | USEPA/Office of Pesticide ProgramsReregistration 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] |
| FIFRA-Anforderungen | Tolerances are established for residues of the herbicide bromacil (5-bromo-3-sec-butyl-6-methyluracil) in or on the following food commodities: [Table#3208]Based on the reviews of the generic data for the active ingredients in this case, the Agency has sufficient information on the health effects of bromacil and its lithium salt, but has certain limitations on their potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that bromacil products, if labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks of adverse effects to humans or the environment. Under the Food Quality Protection Act of 1996, the Agency has determined that there is a reasonable certainty that no harm will result to infants and children or to the general population from aggregate exposure to bromacil. Therefore, the Agency concludes that products containing bromacil for all uses are eligible for reregistration.As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Bromacil is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0041Pesticide type: herbicideRegistration Standard Date: 09/30/82Case Status: RED Approved 09/96OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.Active ingredient (AI): BromacilData Call-in (DCI) Date(s): 09/30/91, 03/26/97AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI. |
| OSHA Standards | Vacated 1989 OSHA PEL TWA 1 ppm (10 mg/cu m) is still enforced in some states. |
| Reactivity Profile | BROMACIL is incompatible with the following: Strong acids (decomposes slowly), oxidizers, heat, sparks, open flames (NIOSH, 2024). |
| Chemical Dangers | Decomposes on heating. This produces toxic fumes including hydrogen bromide and nitrogen oxides. Decomposes on contact with acids or oxidants. |
| Brandbekämpfung | In case of fire in the surroundings, use appropriate extinguishing media. |
| Erste-Hilfe-Maßnahmen | 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.Give one or two glasses of water to drink. Refer for medical attention . |
| Erste Hilfe | Excerpt from NIOSH Pocket Guide for Bromacil:(General first aid procedures) |
| Sichere Lagerung | Keep in a well-ventilated room. Separated from strong oxidants and strong acids. |
| Firefighting Hazards | Under severe dusting conditions, this material may form explosive mixtures in air. /DuPont Hyvar X Herbicide/ |
| Brandbekämpfungsverfahren | 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/ |
| Lagerbedingungen | Do not contaminate water, other pesticides, fertilizer, food or feed in storage. Store in original container. Keep tightly closed in a dry, cool and wellventilated place. Keep out of the reach of children. /DuPont Hyvar X Herbicide/Exposure of water-soluble formulations to air can cause some loss of water solubility.Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water. /Residential users/ |
| Reinigungsverfahren | 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/ |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal and plant lifeand 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. |
| Verschüttetes entsorgen | 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. |
| Preventive Measures | 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. |
| Eye Prevention | Wear safety goggles. |
| Zielorgane | Eyes, skin, respiratory system, thyroid |
| Ökotoxizitätswerte | LC50Species: Coturnix japonica (Japanese quail) diet >5,000 ppm for 5 daysSpecies: Anas platyrhynchos (Mallard Duck)diet >10000 ppm for 8 daysSpecies: Colinus virginianus (Northern Bobwhite Quail)LD50Species: Colinus virginianus (Northern Bobwhite Quail) age 21 weeksoral via capsule 2250 mg/kgFor more Ecotoxicity Values (Complete) data for BROMACIL (34 total), please visit the HSDB record page. |
| Umweltverhalten | 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. |
| Lebensmitteluntersuchungswerte | 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 analyzedtested for, not detected2005 - 2,638 domestic and 5,286 import samples collected and analyzed2006 - 1,392 domestic samples from 41 States and Puerto Rico and 4,317 import samples from 87 countries were analyzedtested for, not detected(2). |
| Unerwünschte Wirkungen | ACGIH Carcinogen - Confirmed Animal. |
| Expositionspfade | The substance can be absorbed into the body by ingestion.inhalation, ingestion, skin and/or eye contact |
| Ökotoxizitätsauszüge | /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 glyphosateKrovar uses bromacil and diuronand 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 runoffthus 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 |
| Plant Concentrations | Bromacil concentration of 30-50 ppm (fresh weight) were detected in tree foliage samples collected 30 to 50 ft away from a Los Alamos, NM roadside where bromacil had been sprayed on a 4-ft wide strip to kill vegetation(1). |
| Signs and Symptoms | Cough.Redness.Redness. Pain.Nausea. Vomiting. Diarrhoea.irritation eyes, skin, upper respiratory systemIn Animals: thyroid injury |
| Acute Toxicity Link | Chemical: UREABOR |
| ICSC Environmental Data | The substance is very toxic to aquatic organisms. |
| Medical Surveillance | Before begining employment and at regular times after that, for those with frequent or potentially high exposures, the following is recommended: Lung function tests. Thyroid function tests. consider x-ray following acute overexposure. |
| Landesrichtlinien für Trinkwasser | (AZ) ARIZONA 80 ug/l(ME) MAINE 70 ug/l |
| Bundesrichtlinien für Trinkwasser | EPA 90 ug/l |
| Berufliche Expositionsstufe (OEB) | B |
| Arbeitsplatzgrenzwert (OEL) | TWA: 1 ppm (10 mg/m3) |
| Wassergefährdungsklasse (WGK) | 2 |
| UN-Transportnummer | UN3077 9/PG 3 |
| RTECS-Nr. | YQ9100000 |
| R-Sätze (R) | 22-36/37/38-50-36 |
| Toxizität | LD50 orally in rats: 5200 mg/kg (Sherman, Kaplan) |
| Gefahrensymbole | Xn,N |
| Sicherheitshinweise (S) | 26-61 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 314-40-9(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1 |
Anwendungen & Verwendung
Beschreibung
Bromacil (CAS 314-40-9) belongs to a class of herbicides known as uracils, first developed by DuPont in 1962. Its herbicidal activity is due to inhibition of photosynthesis in several species of weeds and brush. Since its introduction in 1962, farmers in North and South America and Asia have used bromacil-containing herbicides for crop protection.
Verwenden
Bromacil is a nonselective inhibitor of photosynthesis, absorbed mainly through the root and used for general weed control on uncropped land at 5–15 kg/ha (2–4 kg/ha annual maintenance). It is also used for weed control in citrus plantations and for perennial grass control and annual pineapple plantations.