Chloramben

206.03

206.03

205-123-5

EWG424FFB5

3077

DTXSID2020262

COLORLESS CRYSTALLINE SOLID

29224999

63.3

1.11

Powder

1.4062 (rough estimate)

200-201 °C

312 °C

179.5±27.9 °C

1.6100 (estimate)

H2O: 700 mg/L (25 ºC)

0-6°C

930 mPa @ 100 Deg C

Oral-Rat LD50: 3500 mg/kg; Oral-Mouse LD50: 3725 mg/kg

Combustion produces toxic nitrogen oxides and chloride gases

ODORLESS

FORMS WATER-SOLUBLE ALKALI METAL & AMMONIUM SALTS, THERE IS NO PROBLEM OF PRECIPITATION WITH HARD WATER|STABLE TO HEAT, TO OXIDATION & TO HYDROLYSIS BY ACID OR ALKALINE MEDIA BUT IS DECOMP BY SODIUM HYPOCHLORITE SOLN|PURPLISH-WHITE POWDER /TECHNICAL PRODUCT/

Insoluble in water.

Acids, Carboxylic

CHLORAMBEN reacts with sodium hypochlorite solutions (NTP, 1992).

UN 3077 9/PG 3

3

45-36/37/38-40

53-22-26-36/37/39-45-36

DG1925000

T,Xn

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

RAPIDLY DECOMPOSED BY LIGHT

P201-P261-P305 + P351 + P338-P308 + P313

H315-H319-H335-H350

Reuse: The use of chemical reagents as a means of disposal is not recommended at the present time. Amiben's shelf life is of sufficient duration to allow for total use of the product in accordance with label directions. On this basis, there should be few instances of small quantities of excess amiben requiring disposal. For the decontamination of amiben containers, the National Agricultural Chemical Association (USA) recommends triple rinse. "Triple rinse" means the flushing of containers three times, each time using a volume of the normal diluent equal to approx ten percent of the container's capacity and adding the rinse liquid to the spray mixture or disposing it by the method prescribed for disposing of the pesticide.|Incinerate in a unit equipped with an effluent gas scrubber at a temperature above 1000 C about 1-2 seconds. Recommendable method: Incineration.|Wet Oxidation: Studies of wet oxidation process applied to amiben herbicide process wastes indicate 88 to 99.5% destruction of the active ingredient.

USEPA/ODW; Health Advisories for 50 Pesticides (8/88) NTIS No. PB88-245931|DHEW/NCI; Bioassay of Chloramben for Possible Carcinogenicity (1977) Technical Rpt Series No. 25 DHEW Pub No. (NIH) 77-825

Flash point data for this compound is not available, but it is probably combustible. (NTP, 1992)

|Danger|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 197 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this material can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

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)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Nonflammable

Avoid skin and eye contact, inhalation of spray mists and drifting.

MILD TO MODERATE DERMAL IRRITATION.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Amiben is included on this list.

Chloramben is used as a herbicide on a number of crops. Limited information is available on the health effects of chloramben. Acute (short-term) exposure to high levels of chloramben in humans results in mild to moderate dermal irritation. No information is available on the chronic (long-term) effects of chloramben in humans. Animal studies have reported effects on the liver from chronic oral exposure to chloramben. A National Toxicology Program Study reported that oral exposure to chloramben caused liver tumors in mice, but not in rats. EPA has not classified chloramben for potential carcinogenicity.

Amiben was reported in ambient air between 1970 and 1971(1).

moderately toxic

... CAFFEINE & CHLORAMBEN REACTED TO FORM AN INSOL COMPLEX IN STOMACH OF RATS. DECREASED GI ABSORPTION OF (14)C CAFFEINE WAS ASSOCIATED WITH AN INCOMPLETE DISSOCIATION OF THE CHLORAMBEN-CAFFEINE COMPLEX IN THE INTESTINAL TRACT.

LD50 Rat oral 3,500 to 5,620 mg/kg|LD50 Rabbit dermal 3,136 mg/kg

A bioassay of technical grade chloramben for possible carcinogenicity was conducted by administering the test material in feed to Osborne-Mendel rats and B6C3F1 mice. Groups of 50 rats and 50 mice of both sexes were administered chloramben at one of two doses, either 10,000 or 20,000 ppm. The rats were treated for 80 wk, then observed for 32 or 33 wk; the mice were treated for 80 wk, then observed for 11 or 12 wk. Matched controls consisted of groups of 10 untreated rats and 10 untreated mice of each sex; pooled controls, used for statistical evaluation, consisted of these matched controls combined with 75 untreated male and 75 untreated female rats or 70 untreated male and 70 untreated female mice from similarly performed bioassays of six other test chemicals. Surviving rats were killed at 112 or 113 wk; surviving mice were killed at 91 or 92 wk. In male rats, hemangiomas occurred at a significantly higher incidence in the low dose animals than in the pooled controls (controls 0/73, low dose 5/48, p=0.009). This lesion was not considered to be related to chloramben administration, since the tumor did not occur at a significantly higher incidence in the high dose group than in the pooled control group, and the incidences did not show a significant dose related trend. In both male and female mice, the incidences of hepatocellular carcinoma showed significant dose related trends using pooled control (for females controls: 2/67, low dose 7/48, high dose 10/50, p=0.004). Direct comparisons showed significantly higher incidences of the tumor in low dose males (p=0.008) and in the high dose females (p=0.003) than in the pooled controls. Probability levels of p=0.028 in high dose males and p=0.027 in low dose females were attained. In male mice, however, the incidence of hepatocellular carcinoma was considered only marginally associated with the administration of chloramben because of variations in the spontaneous incidence of this lesion in male mice encountered at this laboratory. Under the conditions of this bioassay, there were no tumors in Osborne-Mendel rats that were significantly related to administration of the chemical. In B6C3F1 female mice, chloramben was carcinogenic, producing hepatocellular carcinomas in treated animals. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Equivocal; Female Mice: Positive.

Amiben is used as an herbicide and it is released to the environment by ground spray or granular application(1).

LOSS /OF CHLORAMBEN/ BY LEACHING WAS MOST PRONOUNCED FROM A SANDY SOIL & WAS PROGRESSIVELY LESS AS CLAY & ORGANIC COMPONENTS INCREASED.|VOLATILITY & SOIL MOVEMENT ARE MORE DEPENDENT ON FORM OF CHLORAMBEN APPLIED THAN ON SOIL TYPE. ...ALUMINUM & AMMONIUM SALTS... WERE EASILY LEACHED FROM SEVERAL ARKANSAS SOILS. METHYL & BUTOXYETHYL ESTERS RESISTED LEACHING, WHILE AMIDE WAS INTERMEDIATE WITH RESPECT TO LEACHING.|/FROM INVESTIGATIVE STUDIES/ ... ONE MIGHT EXPECT THAT CHLORAMBEN PERSISTENCE ... /MAY/ BE GREATEST AS THE BUTOXYETHYL ESTER IN DRY SOIL OF HIGH ORG CONTENT & LEAST FOR ... SALT IN A MOIST SANDY SOIL WHERE HIGH RAINFALL WOULD ACCELERATE LEACHING.|ABSORPTION OF CHLORAMBEN TO SOIL PARTICLES SIGNIFICANTLY REDUCED HERBICIDAL ACTIVITY. ... IN ONE INSTANCE, UNDER CONTROLLED LAB CONDITIONS, A MUCK SOIL ABSORBED 29% OF APPLIED CHLORAMBEN, WHEREAS A SILTY CLAY LOAM ABSORBED ONLY 9%. ... DESORPTION OF CHLORAMBEN FROM MUCK SOILS IS SLOW.|For more Environmental Fate (Complete) data for AMIBEN (9 total), please visit the HSDB record page.

... A 90% REDUCTION IN PHYTOTOXICITY TO OAT SEEDLINGS /WAS DEMONSTRATED/ WHEN AQ ETHANOL SOLUTIONS OF CHLORAMBEN OR ITS METHYL ESTER WERE IRRADIATED WITH UV LIGHT FOR 6 HR. PHOTOINACTIVATION WAS GREATLY REDUCED WHEN FREE AMINO GROUP OF CHLORAMBEN WAS PROTECTED FROM PHOTOOXIDATION.|WHEN OXIDN WAS PREVENTED ... /CHLORAMBEN & THE METHYL ESTER/ UNDERWENT REDUCTIVE DECHLORINATION @ 2 POSITION TO YIELD 3-AMINO-5-CHLOROBENZOIC ACID & METHYL 3-AMINO-5-CHLOROBENZOATE, RESPECTIVELY. TRACE OF COMPLETELY DECHLORINATED PRODUCT, 3-AMINOBENZOIC ACID, WAS PRODUCED FROM CHLORAMBEN.|UNDER AEROBIC CONDITIONS, IRRADIATED AQ SOLN OF CHLORAMBEN RAPIDLY TURN BROWN. SOLN CONTAINED INORG CHLORIDE IONS & COMPLEX MIXT OF POLYMERIZATION & OXIDN PRODUCTS. ... /IT IS/ SUGGESTED THAT AN INITIAL AMINO RADICAL FORMATION IS PREDOMINANT REACTION IN OXIDATIVE PHOTODECOMP.|AMIDE & METHYL ESTER ... UNDERWENT RAPID HYDROLYSIS IN SOIL. IN MOIST SOIL HALF-LIFE WAS 2.9 DAYS FOR METHYL ESTER, 7.5 DAYS FOR HYDROXYPROPYL ESTER, & MORE THAN 16 DAYS FOR BUTOXYETHYL ESTER.|For more Environmental Abiotic Degradation (Complete) data for AMIBEN (6 total), please visit the HSDB record page.

Based on a measured water solubility of 700 mg/L at 25 °C(2) and a regression derived equation(1), a BCF of 15.34 can be estimated for Amiben(SRC). This BCF value suggests that Amiben may not bioconcentrate in aquatic organisms(SRC).

30.20 L/kg|Amiben is expected to have anionic properties in most soil systems under environmental conditions (pH 5-9). When a column of Ella island soil type (pH 3.8, 1.6% organic matter, 82.7% sand, 12.2% silt, and 5.2% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm (14)-COOH-labelled Amiben, 1.4 ppm (24.6%) and 5.0 ppm (18.5%) Amiben adsorbed to the soil, respectively. When a column of Kewaunee clay soil type (pH 6.4, 3.8% organic matter, 14% sand, 35.1% silt, and 48.7% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm 14COOH-labelled Amiben, 0.6 ppm (11.1%) and 2.6 ppm (9.8%) Amiben adsorbed to the soil, respectively. When a column of Poygan silty clay soil type (pH 7.2, 10% organic matter, 6% sand, 58.9% silt, and 33.6% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm 14COOH-labelled Amiben, 1.4 ppm (24.6%) and 5.4 ppm (20.1%) Amiben adsorbed to the soil, respectively. Therefore, soil pH and organic matter content are the primary factors controlling Amiben adsorption with higher adsorption to soil occurring either at a low pH with a low organic matter content or at a neutral pH with a high organic matter content(1).|In a study of the adsorption of organic herbicides by montmorillonite, Amiben at an initial concentration of 500 umol/L exhibited no adsorption or negative adsorption to Na-montmorillonite soil (pH 6.8 and 87.0 cation exchange capacity) and H-montmorillonite soil (pH 3.35 and 73.5 cation exchange capacity)(3). Amiben was more strongly adsorbed to soil with high organic matter content; furthermore, adsorption of Amiben to soil particles significantly reduced herbicidal activity(5). Based on adsorption studies of 12 soils, a mean Koc value of 190 was determined for amiben(1). In another adsorption study, an experimental Koc value of 21 was determined for Amiben(2). These Koc values indicate that Amiben will have high to very high mobility in soil and will leach(4). However, protonated Amiben may exhibit higher adsorption at lower pHs than its Koc values indicate(SRC).

A Henry's Law constant of 2.1X10-11 atm cu-m/mole at 25 °C can be estimated for Amiben based on a bond contribution method(2). This value of Henry's Law constant suggests that Amiben is less volatile than water(1).

GROUNDWATER: Amiben was detected in 1 Wisconsin well at a concentration exceeding the recommended health advisory of 10 ug/L(1). According to a Wisconsin groundwater monitoring study, Amiben was detected in 2% of the wells studied at a maximum concentration of 50 ug/L(2). Also, Amiben detection in groundwater was reported in Iowa, but no concns were given(2). Amiben was detected in wells from 12 of 91 farms during November and December, 1984 in Southern Ontario, Canada(3). In a monitoring survey studying the occurrence of pesticides in Ontario farm wells, Amiben was detected in 6 of 103 wells in 1986 and in 1 of 76 wells in 1987(4).|DRINKING WATER: Amiben has been qualitatively identified in drinking water from Seattle, WA on November 15, 1976(1).

Amiben is used as a herbicide for control of seedling grass, broadleaf weeds, velvetleaf, ragweed, redroot pigweed, and Pennsylvania smartweed(1). It is released by ground spray or granular application to soybeans, drybeans, snapbeans, lima beans, seedling asparagus, cucumbers, cantaloupes, pumpkin, squash, corn; tomatoes, peppers, sweet potatoes, and various ornamentals(1). Therefore, workers may be exposed to Amiben by dermal contact or inhalation during the application of Amiben(SRC). The general public may be exposed to Amiben through drinking water or groundwater supplies in which it has been detected(SRC).|TOXIC SUBSTANCES DETECTED IN PRODUCTION OF AMIBEN ARE GIVEN.

... /STUDIES IN A LACTATING COW SHOWED THAT OVER/ A PERIOD OF 4 DAYS, DIETARY CHLORAMBEN (5 PPM IN DAILY RATION) WAS RAPIDLY EXCRETED IN URINE (88%) & FECES (5%). NO RESIDUES WERE DETECTED IN THE MILK. APPROX 18% OF CHLORAMBEN IN URINE WAS PRESENT AS UNKNOWN CONJUGATED MATERIAL.|... UNPUBLISHED FEEDING STUDIES WITH DOGS ... SHOWED ... THAT DIETARY CHLORAMBEN (5 PPM) WAS RAPIDLY EXCRETED IN URINE & FECES, & NO ... RESIDUES WERE DETECTED IN TISSUE SAMPLES TAKEN ... .|ACIDIC COMPOUNDS SUCH AS 3-AMINO-2,5-DICHLOROBENZOIC ACID ARE BOUND TO BOVINE SERUM ALBUMIN. BLOOD/TISSUE RATIOS OF (14)C FROM RATS DOSED WITH LABELED ACID WERE HIGHLY CORRELATED WITH THE LOGARITHM OF BINDING AFFINITY CONSTANTS.

THE MAJOR PATHWAY OF CHLORAMBEN METABOLISM IN BOTH TOLERANT & SUSCEPTIBLE PLANT SPECIES APPEARS TO BE A RAPID FORMATION OF METHANOL-SOLUBLE CONJUGATES & "BOUND" INSOLUBLE RESIDUES.|IN PLANTS, AMIBEN IS CONVERTED TO N-GLUCOSYLAMINE. THE ENZYME, ISOLATED FROM SOYBEANS ... FOUND TO BE SPECIFIC FOR URIDINE DIPHOSPHATE-5'-GLUCOSE & CORRESPONDING THYMIDINE ANALOG.|... THE PROLONGED IN VIVO STABILITY, IMMOBILITY, & ACCUM OF ... /THE N-GLUCOSIDE CONJUGATE/ IN BOTH SUSCEPTIBLE & TOLERANT PLANTS STRONGLY ... /SUGGESTS/ THAT N-GLUCOSIDE BIOSYNTHESIS IS A MAJOR DETOXICATION MECHANISM.|YIELDS 3-AMINO-2,5-DICHLOROBENZOIC ACID-N-GLUCOSIDE IN SOYBEAN, BARLEY, BEET, TOMATO, CUCUMBER. /FROM TABLE/|CHLORAMBEN METAB IN PLANTS. A REPORTED CHLORAMBEN-X CONJUGATE IDENTIFIED AS METHYL 3-AMINO-2,5-DICHLOROBENZOATE (CHLORAMBEN METHYL ESTER) WAS AN ARTIFACT FORMED BY TRANSESTERIFICATION OF AN UNKNOWN ESTER METABOLITE DURING CLEAN UP OF METHANOL EXTRACTS OF FLORISIL COLUMNS.

ACUTE/CHRONIC HAZARDS: This compound emits toxic fumes when heated to decomposition. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

MILD TO MODERATE DERMAL IRRITATION, NO EVIDENCE OF SYSTEMIC TOXICITY.

Amiben

98% AS A HERBICIDE FOR GRASSES & BROADLEAF WEEDS ON SOYBEANS; 2% AS A HERBICIDE FOR GRASS & BROADLEAF WEEDS ON OTHER CROPS (DRY BEANS, LIMA BEANS, SEEDLING ASPARAGUS, PUMPKINS, SQUASH, CORN, TOMATOES, PEPPERS, & SWEET POTATOES) (1971)

THESE INCLUDE; 'AMIBEN', AQUEOUS SOLN (240 G AE/L) & 'AMIBEN GRANULAR 10%', GRANULES (100 G AE/KG).|THE TECHNICAL PRODUCT IS ... ABOUT 90% PURE ...

Benzoic acid, 3-amino-2,5-dichloro-: ACTIVE|INHIBITS ROOT DEVELOPMENT OF SEEDLING WEEDS.|/AMIBEN IS SUGGESTED FOR USE/ ... AT 2-4 KG AE/HA.|Used at 2 ug ai/kg

... PRODUCT ANALYSIS IS BY VOLUMETRIC METHODS OR ULTRAVIOLET SPECTROMETRY.|... RESIDUES IN POTATO, SWEET CORN, SNAP BEANS, & CARROTS, DIGEST IN ALKALI, ACIDIFY, EXTRACT WITH ETHER. ... RESIDUE PARTITIONED BETWEEN HEXANE & ACETONITRILE ... ASSAY ACETONITRILE FRACTION BY ... /GAS CHROMATOGRAPHY/.|ADDN OF SMALL QUANTITIES OF ORGANIC ACIDS TO MOBILE PHASE SIGNIFICANTLY IMPROVED CHROMATOGRAPHY ON SILICA GEL OF BOTH POLAR BASIC CMPD.|GAS CHROMATOGRAPHIC ANALYSIS OF SIX POLAR ORGANO NITROGEN HERBICIDES INCLUDING CHLORAMBEN. A COULSON ELECTROLYTIC CONDUCTIVITY DETECTOR (NITROGEN MODE) WAS USED.|Determination: dry granular formulations ... , liquid formulations ... Spectrophotometer method.

Hazardous Air Pollutants (HAPs)|Agrochemicals -> Herbicides|HERBICIDES