2,2-Dibrom-2-cyanacetamid

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: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

LD50; Species: /Anas platyrhynchos/ (Mallard duck); oral 205 mg/kg (technical grade) /from table/

LD50; Species: /Colinus virginianus/ (Bobwhite quail); oral 150 mg/kg (technical grade) /from table/

LD50; Species: /Colinus virginianus/ (Bobwhite quail); oral 354 mg/kg (100% a.i.) /from table/

LC50; Species: Colinus virginianus (Northern Bobwhite Quail) age 14 days; diet (chemical incorporated into food) >10000 ppm for 8 days

For more Ecotoxicity Values (Complete) data for 2,2-DIBROMO-3-NITRILOPROPIONAMIDE (21 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 58(SRC), determined from a log Kow of 0.80(2) and a regression-derived equation(3), indicates that 2,2-dibromo-3-nitrilopropionamide is expected to have high mobility in soil(SRC). Volatilization of 2,2-dibromo-3-nitrilopropionamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 9.0X10-4 mm Hg(2), and water solubility, 1.5X10+4 mg/L(2). 2,2-Dibromo-3-nitrilopropionamide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Biodegradation in soil may be an important environmental fate process; however, degradation in soil is expected to be due to both abiotic and biotic processes(2,4). 2,2-Dibromo-3-nitrilopropionamide is susceptible to aqueous hydrolysis in moist soils and susceptible to photodegradation when exposed to sunlight(2,4). Half-lives ranged from 4 to 25 hours in 7 different soils with pH values of 4.8 to 7.5(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 58(SRC), determined from a log Kow of 0.80(2) and a regression-derived equation(3), indicates that 2,2-dibromo-3-nitrilopropionamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.9X10-8 atm-cu m/mole(SRC), determined from its vapor pressure, 9.0X10-4 mm Hg(2) and water solubility, 1.5X10+4 mg/L(2). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Degradation in water is due to both abiotic and biotic processes(2,6). Hydrolysis half-lives of 67 days, 63 hours, and 73 minutes were measured for 2,2-dibromo-3-nitrilopropionamide at pH 5, 7, and 9, respectively(2). Dibromoacetic acid is the major degradate at pH 5 while dibromoacetonitrile is the major degradate at pH values of 7 and 9(2). The half-life of 2,2-dibromo-3-nitrilopropionamide is less than 4 hours in anaerobic and aerobic metabolism studies(2). Degradates include oxalic acid, 2-cyanoacetamide, bromoacetamide, dibromoacetic acid, bromoacetic acid, and dibromoacetonitrile; the concentration of each degradate over time varies with the oxygen condition(2). 2,2-Dibromo-3-nitrilopropionamide is susceptible to photodegradation in water(6); <1% of initial 2,2-dibromo-3-nitrilopropionamide remained after exposure to sunlight for 28 days(6). Sunlight degrades 2,2-dibromo-3-nitrilopropionamide in water at rates that become relatively fast compared to hydrolysis at pH less than 5(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,2-dibromo-3-nitrilopropionamide, which has a vapor pressure of 9X10-4 mm Hg at 25 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,2-dibromo-3-nitrilopropionamide 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 8 days(SRC), calculated from its rate constant of 2.0X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Based on photolysis studies showing degradation in aqueous solution exposed to sunlight (99% loss in 28 days)(4), 2,2-dibromo-3-nitrilopropionamide is expected to be susceptible to direct photolysis in the atmosphere(SRC).

Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

IDENTIFICATION AND USE: 2,2-Dibromo-3-nitrilopropionamide (DBNPA) is white to "off white" crystalline solid. It is used as a pesticide(Trade Names: DBNPA, Slimicide 508, XD-7287L Antimicrobial, XD-1603.) Main uses include the following: algicide, bactericide and fungicide; preservative used mainly in pulp, paper and paperboard mill water systems and in industrial water cooling systems. It is also used as a preservative in animal glues, metalworking cutting fluids, oil recovery drilling muds, latex paints, resin/latex/polymer emulsions, latex/oil/varnish paints, and paper and paper products. HUMAN EXPOSURE AND TOXICITY: Several human incident reports concerning DBNPA are on file with the EPA. These include eye, throat, & respiratory irritation, runny nose, & headache. Generally the effects arose with spills or misuse. No treatment related effects on chromosome aberrations in proliferating cultured human lymphocyte were reported with or without metabolic activation. ANIMAL STUDIES: A primary eye irritation study in rabbits resulted in severe corneal damage. Dermal irritation was noted in rats of both sexes. Renal tubular alterations of the kidneys (minimal cytoplasmic swelling and vacuolization) were described in female rats. Developmental study in rabbits found retarded ossification of several fetal skeletal elements. The occurrence of structural alterations at a maternally non-toxic dose indicates that DBNPA is a developmental toxicant in rabbits. DBNPA did not induce micronuclei formation in mice. In Salmonella typhimurium TA98, TA100, TA1535, and TA1537 and Escherichia coli WP2uvrA the test material did not produce a positive increase in the number of revertants per plate of any of the test strains either in the presence or absence of microsomal activation. The positive controls were functional. Sister chromatid exchange (SCE) assay in Chinese hamster ovary cells after one hour exposures at DBNPA was negative.

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS Dashboard Application; Available from, as of June 27, 2014: http://actor.epa.gov/dashboard/]

The Koc of 2,2-dibromo-3-nitrilopropionamide is estimated as 58(SRC), using a log Kow of 0.80(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,2-dibromo-3-nitrilopropionamide is expected to have high mobility in soil.

/SIGNS AND SYMPTOMS/ Several human incident reports concerning DBNPA are on file with the /EPA/. These include eye, throat, & respiratory irritation, runny nose, & headache. Generally the effects arose with spills or misuse.

/GENOTOXICITY/ Samples of proliferating cultured human lymphocytes were exposed to C-103 (2,2-Dibromo-3- Nitrilopropionamide, DBNPG, lot 23/1817, 98% stated purity) with and without metabolic activation (S-9 fraction of Aroclor-1254 induced rat liver homogenates) for 2 hours, incubated for 22 or 46 hours, arrested in metaphase with colchicine, fixed, stained and microscopically examined for chromosome aberrations. 100 cells were evaluated per sample with two samples per treatment. Treatment levels without S-9 were 0, 25, 37.5 and 50 ug/mL (22 hour incubation) and 0 and 37.5 ug/mL (46 hour incubation) and with S-9 were 0, 5, 25, and 50 ug/mL (22 hour incubation) and 0 and 37.5 ug/mL (46 hour incubation). Positive controls were adequate. No treatment related effects on chromosome aberrations were reported.

2,2-Dibromo-3-nitrilopropionamide's production and use as a bactericide and algicide in commercial water cooling and treatment systems and paper-pulp mill water systems(1) may result in its release to the environment through various waste streams(SRC).

AEROBIC: The disappearance of 2,2-dibromo-3-nitrilopropionamide at 50 ppm in soil was more rapid than when present in an aqueous solution at a similar pH(1). Degradation in 7 soils was measured; half-lives of 4, 12, 15, 15, 6, 25, and 15 hours were reported for a sandy loam (pH 7.5), loam (pH 4.8), silty loam (pH 5.8), sandy loam (pH 6.5), loamy sand (pH 5.8), silty clay loam (pH 5.1), and loam (pH 4.8) soil, respectively(1). 2,2-Dibromo-3-nitrilopropionamide has a half-life of less than 4 hours in an aerobic aquatic metabolism study(2). Dibromoacetic acid (reached 66% of applied at 0 hour, 9% at hour 5) and 2-cyanoacetamide (reached 56.5% of applied at hour 5, 2.3% at day 30) were the major degradates(2). Other degradates include oxalic acid, bromoacetic acid, bromoacetamide, and dibromoacetonitrile(2). Oxalic acid, 2-cyanoacetamide (16% by day 2) and bromoacetamide (2% by day 2) were found in the sediment layer(2). 2,2-Dibromo-3-nitrilopropionamide, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test classifying the compound as not readily biodegradable(3). Microbial degradation of 2,2-dibromo-3-nitrilopropionamide has been demonstrated by the use of tracer techniques (14C-radio-labeled) which yielded 40% 14-CO2 after two weeks in the presence of waste treatment sludge(1).

ANAEROBIC: 2,2-Dibromo-3-nitilopropionamide has a half-life of less than 4 hours in an anaerobic aquatic metabolism study; residues were mainly found in the aqueous layer. Concentrations of the two main degradates 2-cyanoacetamide (reached 56% of applied within 7 days) and dibromoacetic acid (reached 27% of applied at 0 hr, 17% by day 48) were measured. Other minor degradates include oxalic acid, bromoacetamide and dibromoactonitrile. 2-Cyanoacetamide, dibromoacetonitrile and bromoacetamide were found in the sediment layer. The anaerobic metabolism study includes degradation due to both biotic and abiotic mechanisms(1).

An estimated BCF of 3 was calculated in fish for 2,2-dibromo-3-nitrilopropionamide(SRC), using a log Kow of 0.80(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). Using carp (Cyprinus carpio) which were exposed over an 8-week period, 2,2-dibromo-3-nitrilopropionamide was reported to have low bioconcentration (BCF value not available)(4).

The Henry's Law constant for 2,2-dibromo-3-nitrilopropionamide is estimated as 1.9X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 9.0X10-4 mm Hg(1), and water solubility, 1.5X10+4 mg/L(1). This Henry's Law constant indicates that 2,2-dibromo-3-nitrilopropionamide is expected to be essentially nonvolatile from water surfaces(2). 2,2-Dibromo-3-nitrilopropionamide's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 2,2-Dibromo-3-nitrilopropionamide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

/LABORATORY ANIMALS: Acute Exposure/ A primary eye irritation study in rabbits resulted in severe corneal damage, which was considered permanent; in all treated rabbits DBNPA was corrosive to the eyes, with max opacity within 1 hr. Rabbits treated with DBNPA in a primary dermal irritation study (4 hr exposure to 0.5 g) experienced erythema & edema, with exfoliation after five days. Two dermal sensitization studies with guinea pigs found DBNPA to be a weak sensitizer.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a subchronic toxicity study, rats were given DBNPA for 90 days by gavage at doses of 0, 5, 13, or 30 mg/kg/day. The NOEL was 5 mg/kg/day. The LOEL was 13 mg/kg/day based on dyspnea at this dose & higher. The animals with dyspnea also had weight loss & some of them died. Doses of 0, 103, 309, or 1031 mg/kg/day of DBNPA were applied to the skin of rats (6 hrs/day; 5 days/wk) for 90 days. The systemic NOEL was 309 mg/kg/day. The systemic LOEL was 1031 mg/kg/day based on clinical chemistry findings of reduced triglyceride levels in males, reduced cholesterol as well as elevated alkaline phosphatase & chloride in females, & urine pH at or above 9 in some males. The dermal irritation NOEL was 103 mg/kg/day. Dermal irritation (erythema &/or edema) was transient in several rats of both sexes at the two highest doses.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ 2,2-Dibromo-3-Nitrilopropionamide (DBNPA, XD-1603L, 95.7% stated purity, run 09020-24) was given at 0, 20, 100, or 500 ppm in the drinking water (pH 4 or pH 8) for 90 days to 10 Sprague- Dawley Spartan rats/sex/group. DBPNA is unstable at pH 8 and exposure was to breakdown products. The only treatment related effect of toxicological concern was minimal renal tubular alterations of the kidneys (minimal cytoplasmic swelling and vacuolization) in female rats maintained at 500 ppm, at pH 8 (NOEL = 100, pH 8; male, 8 mg/kg/day; female 15.9 mg/kg/day).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ A 20% solution of DBNPA (lot MM890624, tetraethylene glycol vehicle) was applied undiluted for 6 hr/day, 5 days/week for 13 weeks to a 5 X 5 cm clipped patch (occluded) on the backs of 10 Fischer 344 rats/sex/group at 0, 103, 309, or 1031 mg/kg/day (0.0, 0.4, 1.2 or 4.0 mL/kg/day). Adequate ophthalmology, hematology, clinical chemistry, and urinalysis were performed with no treatment-related findings. A modified FOB was also included. Treatment related responses were localized to the application site: transient dermal irritation at 309 mg/kg/day and dermal irritation, erythema, edema, scabs, hyperkeratosis and inflammation at 1031 mg/kg/day (dermal NOEL = 103 mg/kg/day, systemic NOEL > or =1031 mg/kg/day).

For more Non-Human Toxicity Excerpts (Complete) data for 2,2-DIBROMO-3-NITRILOPROPIONAMIDE (16 total), please visit the HSDB record page.

Based on the reviews of the generic data for the active ingredient DBNPA the Agency has sufficient information on the health effects of DBNPA and on its potential for causing adverse effects in fish and wildlife and the environment. Therefore, the Agency concludes that specific products containing DBNPA for all uses except single flow-through cooling tower uses are eligible for reregistration when labeled and used as specified in this Reregistration Eligibility Decision, since they will not pose unreasonable risks or adverse effects to humans or the environment.

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Dibromo-3-nitrilopropionamide (DBNPA) is found on List C. Case No: 3056; Pesticide type: fungicide, herbicide, antimicrobial; Case Status: RED Approved; OPP 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): dibromo-3-nitrilopropionamide; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.