Barban

258.1

258.10

202-930-4

33306K781F

29168

3077|3082

DTXSID3041617

Crystalline solid|COLORLESS|Crystals from n-hexane + benzene

29242990

38.3

3.41 /Estimated/

White Powder/Solid

1.403 g/cm³ @ Temp: 25 °C

75-76 °C

Degrades before boiling

122 deg F (Closed cup)

1.6070 (estimate)

In water, 1.1X10+1 mg/L at 25 deg C

0-6°C

3.8X10-7 mm Hg at 25 deg C

Oral-Rat  LD50: 527 mg/kg; Oral-Mouse LD50: 322 mg/kg

Flammable; burning produces toxic chloride and nitrogen oxide fumes

ODORLESS SOLID

Henry's Law constant: 1.17X10-8 atm cu m/mol at 25 °C /Estimated/

Tan solid /Technical/|Hydrolyzed by alkali with liberation of the terminal chlorine. Hydrolysis under acidic conditions gives 3-chloroacrylic acid|Decomposition temperature: not available; technical material greater than 95% pure is pale brown with faint odor.|VP = 0.05 mPa at 25 °C|For more Other Experimental Properties (Complete) data for BARBAN (7 total), please visit the HSDB record page.

Hydrolyzed by strong acid or base.

Carbamates

BARBAN is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Liq concn may cause corrosion of tin plate & mild steel at the liq-air interface; aluminum, phenolic-lined cans or glass are recommended for storage|Corrosive

UN30779/PG3

3

22-43-50/53

24-36/37-60-61

FD7700000

Xn,N

Storehouse ventilated at low temperature and dry; stored separately from oxidants, alkalis, food additives

Storage at alternating temp of 50 to -15 deg C for 6 months had no adverse effects on emulsion performance

P273-P280-P501

H302-H317-H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P391, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 197 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Possible allergic reaction in man by skin contact should be avoided by the use of plastic protective clothing.|Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, nec, liquid)/|Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticide, liquid, nos (compounds and preparations) (agricultural insecticides, nec, liquid); carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticide, solid, nos (compounds and preparations) (insecticides, other than agricultural, nec); Carbamate pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/

If material /is/ on fire or involved in /a/ fire do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Carbamate pesticide, liquid, nos, (compounds and preparations) (agricultural insecticides, nec, liquid); Carbamate pesticide, liquid, nos (compounds and preparations) (agricultural insecticides, nec, liquid); Carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec/|Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticide, liquid nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Carbamate pesticide, solid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/

A system for removing pesticides from the wash water produced by pesticide applicators as they clean their equipment has been developed. The first step is the flocculation/coagulation and sedimentation of the pesticide-contaminated wash water. The supernatant from the first step is then passed through activated carbon columns. /Pesticides/

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.|/When handling/ do not get in eyes, or on skin or clothing.

Barban... is a potent skin sensitizing agent in man.|Irritant and dermal sensitizer.

U280; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

U280; As stipulated in 40 CFR 261.33, when barban, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

highly toxic

LD50 Rabbit oral 600 mg/kg|LD50 Mouse oral 322 mg/kg|LD50 Guinea pig oral 240 mg/kg|LD50 Rat percutaneous >1600 mg/kg|For more Non-Human Toxicity Values (Complete) data for BARBAN (6 total), please visit the HSDB record page.

/FIELD STUDIES/ At the application level of 5 kg/ha (20 ppm) on the soil Psuedogley-Parabraunerde cretaceous clay, barban killed 40 percent of ammonium oxidizers, based upon the assumption of initial inhibition(1). The estimated rate of application of barban for > 25 percent inhibition in soil (ammonium oxidation) was 100 to 250 kg/ha at 0.5 to 2 applications per year. The estimated rate of application of barban for > 25 percent inhibition in soil (nitrite oxidation) was 1 to 2 kg/ha at 0.5 to 2 applications per year(2).

Barban's former production and use as a herbicide and plant growth regulator(1) is expected to have resulted in its direct release to the environment(SRC).

Decomposes within 28-38 days of the last plant spraying.|TERRESTRIAL FATE: RESULTANT AVG PERSISTENCE @ RECOMMENDED RATES: DOWN TO TRACE AMT WITHIN 3 WK IN MOST SOILS.|Terrestrial fate: Duration of residual activity in soil 2-3 months (at 3 kg/ha).|TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,200(SRC), determined from a water solubility of 11 mg/L(2) and a regression-derived equation(3), indicates that barban is expected to have low mobility in soil(SRC). Volatilization of barban from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 3.8X10-7 mm Hg(4), and water solubility mg/L(2). Barban is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Barban was found to disappear more rapidly in non-autoclaved soil than in autoclaved soil(5) and appeared to be stable in the presence of anaerobic microorganisms(6); however, specific details were not available.|For more Environmental Fate (Complete) data for BARBAN (7 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of barban with photochemically-produced hydroxyl radicals has been estimated as 5.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of barban with ozone has been estimated as 2.7X10-20 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 420 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 1.63X103 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 1.1 hours and 6.84 minutes at pH values of 7 and 8, respectively(3). Barban does not contain chromophores that would be expected to absorb light at wavelengths >290 nm and would therefore not be susceptible to direct photolysis by sunlight(SRC).|10 ppm barban in water was irradiated for 135 minutes with sunlight lamps at a wavelength of 300 nm in the presence of the surfactants Tergitol TMN-10 (0.2 percent) and Trition X-100 (0.2 percent). Percent loss of barban in pure water was 22; percent loss of barban in the presence of Tergitol TMN-10 and Trition X-100 was 76 and 99 percent, respectively(1). The absorption of barban in n-hexane and ethanol occurred between 277 and 286 nm(2).|2-Chloro-4-aminophenol has been identified as a metabolite of barban in plants(1). It was demonstrated that barban was metabolized in both tolerant wheat and sensitive wild oat to 3-chloroaniline. In leaf-treated tissues, it was concluded that 14C-labeled barban concentration decreased with time and the 3-chloroaniline moiety of barban was complexed as polar metabolites. It was also determined that root-treated soybean plants absorb, translocate, and metabolize 14C-labeled barban. These studies indicated that the barban molecule was not cleaved in soybean(2).

An estimated BCF of 160 was calculated for barban(SRC), using water solubility of 11 mg/L,(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high (SRC), provided the compound is not metabolized by the organism(SRP).

1.15e+03 L/kg|The Koc of barban is estimated as 1,200(SRC), derived from its water solubility of 11 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that barban is expected to have slight mobility in soil. Using TLC and aluminum oxide sorbent, the Rf value of barban was determined to be 0.5(4). The phenylcarbamate herbicides are much more water soluble than the substituted anilines(5). In spite of this, however, they are very immobile in soil systems. These compounds have been shown to be activated by adsorption to soil organic matter. Compounds in this group include barban. The mechanism of adsorption to soil organic matter is thought to involve hydrogen bonding between the carboxyl groups of the organic matter and the nitrogen and carbonyl oxygen of the carbamate(5).

The Henry's Law constant for barban is estimated as 1.2X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 3.8X10-7 mm Hg(1), and water solubility, 11 mg/L(2). This Henry's Law constant indicates that barban is expected to be essentially nonvolatile from water surfaces(3). Barban is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER: Groundwater sampling for pesticides in the United States was conducted by the EPA from 1971 to 1991. Results showed that out of 140 wells sampled in California from 1987 to 1989, no concentration of barban was detected; out of 120 wells sampled in California from 1989 to 1989, no concentration of barban was detected(1). A five year survey of water samples from 738 rural domestic wells and 566 community wells was conducted nationwide. The National Pesticide Survey reporting limit for barban was 1.9 ug/l; barban was not detected in the wells(2). Sampling for pesticides was conducted on 3,322 wells in 47 counties of California from 1993 to 1995. Results showed that out of 35 wells sampled in 3 counties, no concentration of barban was detected(3).

Occupational exposure and general population exposure should be low or non-existent since barban is no longer produced or used. In the past, barban was applied directly to the barley and wheat crops as a herbicide and exposure to this compound was primarily by inhalation of dust particles and dermal contact. (SRC)

When barban was orally administered to rats ... chloroaniline, 2-amino-4-chlorophenol and 4-amino-2-chlorophenol were excreted free and in conjugated form. ... In addition to aniline and m-chloroaniline, hydroxycarbamate was found in blood and all organs. Urine contained p-aminophenol.

When barban was orally administered to rats, hydroxylation and side-chain oxidation occurred. Chloro-aniline, 2-amino-4-chlorophenol and 4-amino-2-chlorophenol were excreted free & in conjugated form. Side-chain oxidation was only of minor importance in metabolism of barban. In addition to aniline & m-chloroaniline, hydroxycarbamate was found in blood & all organs. Urine contained p-aminophenol.|Plant metabolism of carbanilate herbicides has been shown to involve aryl hydroxylation and conjugation instead of hydrolysis. /Carbanilate Herbicides/|After treatment with barban, plants formed a water-soluble 3-chloroaniline compound. Related carbamates were found to form similar products. Another metabolite detected, also in a bound state, was 2-chloro-4-amino-phenol ... .|The 4-chloro-2-butynyl moiety of barban is the most reactive position of the molecule and is implicated in the formation of plant metabolites.|For more Metabolism/Metabolites (Complete) data for BARBAN (6 total), please visit the HSDB record page.

... Interfering with cell division ... is believed to be the primary mode of action.|Weak anticholinesterase inhibitor.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. (ERG, 2016)

Skin contamination should be 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. /Other Herbicides/|If serious dehydration and electrolyte depletion have occurred as a result of vomiting and diarrhea, monitor blood electrolytes and 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. Fluids serve to support excretion of the toxicants. Supportive measures are ordinarily sufficient for successful management of excessive exposures to these herbicides. /Other Herbicides/

/SIGNS AND SYMPTOMS/ Barban... is a potent skin sensitizing agent in man.

barban

Barban was reported as having 52,000 lb AI/yr national use from 1987 through 1989.|100% AS AN HERBICIDE ON WHEAT (1975)

An emulsifiable concentrate (125 and 250 g active ingredient/L)|Carbyne is a 1 lb barban/gal emulsifiable concentrate (12.0% active ingredient).|With esters of mecoprop, dichlorprop, and MCPB as dualweed, with esters of mecoprop and MCPB as neobyne and with esters of metoxuron and simazine as wheatclene, (Dualweed, Neobyne, wheatclene, discontinued by FBC Limited).

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."|... A selective post-emergence herbicide controlling wild oats at the 1.5-2.5 leaf stage, and broad beans, field flax, lentils, lucerne, mustard, oil seed rape, safflower, soyabeans, sugar beet, sunflowers, wheat, Russian wild rye and other grasses.|Compatible with MCPA in combination sprays.|Discontinued 1980 by Gulf Oil.|Compatible with Hoelon 3EC, Avenge, Glean and bromoxynil in combination sprays.

GENERAL SAMPLE, SPECTROPHOTOMETRY @ 550 NM.|RESIDUES: PLANT PORTIONS ARE HYDROLYZED WITH REFLUXING AQ SODIUM HYDROXIDE. ALL BARBAN RESIDUES ARE CONVERTED TO 3-CHLOROANILINE WHICH IS SEPARATED BY STEAM DISTILLATION. THE 3-CHLOROANILINE IS DIAZOTIZED AND COUPLED WITH N-1-NAPHTHYLETHYLENEDIAMINE. THE RESULTING PINK DYE IS ISOLATED ON A CELLULOSE COLUMN AND QUANTITATED BY ITS ABSORBANCE AT 550 NM.|/Barban/ analysis is by UV spectrometry. Residues may be determined by HPLC or by hydrolysis to 3-chloroaniline derivatives of which are measured by GC.|Barban was among a number of pesticides determined in fruit and vegetables by HPLC.|For more Analytic Laboratory Methods (Complete) data for BARBAN (16 total), please visit the HSDB record page.

Agrochemicals -> Herbicides|HERBICIDES