SPECTRUM

Chemical Fact Sheet

Chemical Abstract Number (CAS #) 133904
CASRN 133-90-4
SynonymsChloramben
3-Amino-2,5-dichlorobenzoic acid
Analytical Methods EPA Method 515.3
EPA Method 555
EPA Method 8151
Molecular FormulaC7H5CL2NO2

Link to the National Library of Medicine's Hazardous Substances
Database for more details on this compound.

Use HERBICIDE FOR GRASSES & BROADLEAF WEEDS ON SOYBEANS, DRY BEANS, LIMA BEANS, ASPARAGUS, PUMPKINS, SQUASH, CORN, TOMATOES, PEPPERS, SWEET POTATOES PREPLANT INCORPORATED OR PRE-EMERGENCE WEED CONTROL. APPLIED AT PLANTING OF CORN, DRY BEANS, LIMA BEANS, PEANUTS, PUMPKINS, SEEDLING ASPARAGUS, SOYBEANS, SQUASH, SUNFLOWERS, ESTABLISHED TOMATOES AND PEPPERS, CUCUMBERS, CANTALOUPES, SNAPBEANS, AND SWEET POTATOES. POST EMERGENCE IN SOYBEANS.
Consumption Patterns 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)
Apparent Color COLORLESS CRYSTALLINE SOLID
Odor ODORLESS
Melting Point 200-201 DEG C
Molecular Weight 206.03
Sensitivity Data MILD TO MODERATE DERMAL IRRITATION.
Environmental Impact Amiben may be released to the environment by ground spray or granular application to various crops during its use as a herbicide. If released to the air, Amiben may exist in the particulate or the vapor phase. Particulate phase Amiben may rapidly photodegrade while vapor phase Amiben will degrade relatively rapidly by reaction with photochemically produced hydroxyl radicals (estimated half-life of about 15 hrs). The pKa of the Amiben -COOH group is approximately 3 and the pKa of the Amiben -NH2 group is expected to be <4.6, thereby allowing adsorption of protonated Amiben at low pHs. If released to water, Amiben should not volatilize, bioconcentrate in aquatic organisms, or hydrolyze. In surface water exposed to sunlight, Amiben will photodegrade rapidly (half-life of about 6 hr). In water and soil, Amiben may chemically bind to soil and sediments with higher adsorption occurring either at a low pH with a low organic matter content or at a neutral pH with a high organic matter content. Biodegradation in nonsterile soils may occur via decarboxylation; however, the rate of microbial degradation is expected to depend on the organic content, temperature, and moisture content. On soil surfaces, some Amiben may photodegrade. Workers may be exposed to Amiben by dermal contact or inhalation during the application of Amiben as a herbicide. The general public may be exposed to Amiben through drinking water or groundwater supplies in which it has been detected.
Environmental Fate 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. VOLATILIZATION MAY BE A SIGNIFICANT PATHWAY FOR LOSS OF CHLORAMBEN FROM SOIL SURFACE. NO CRITICAL STUDY OF CHLORAMBEN VOLATILIZATION OR POSSIBLY CODISTILLATION FROM SOIL SURFACE HAS BEEN MADE Resultant average persistence at recommended rates (2.24 to 4.5 kg/ha) approximately 6 to 8 weeks. TERRESTRIAL FATE: Photodecomposition may account for some loss of Amiben on soil surfaces(1,7). Experimental Koc values of 190(9) and 21(10) for the undissociated form indicate that Amiben will have high to very high soil mobility and will leach(11). Amiben is expected to exist as an anion in most soil systems under environmental conditions (pH 5-9) and this form is expected to demonstrate high soil mobility. Amiben has been shown to chemically bind to soil 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(2,5,8). Biodegradation in nonsterile soil may occur(2-6); however, the rate of microbial degradation is expected to depend on the organic content, temperature, and moisture content(4-6). AQUATIC FATE: Volatilization from water, bioconcentration in aquatic organisms and hydrolysis in water are not expected to be important removal processes of Amiben from environmental water systems. In surface water exposed to sunlight, Amiben will photodegrade rapidly (0.001 M Amiben half-life of 6 hr) . Amiben may leach through sediments to groundwater(7-10). However, Amiben may chemically bind to sediments with higher adsorption occurring either at a low pH with a low organic matter content or at a neutral pH with a high organic matter content(2,5). Although the available biodegradation studies are not specific to water(2-6), they suggest that Amiben in water may be susceptible to slow biodegradation. A vapor pressure of 1X10-7 mm Hg at 25 deg C can be estimated using the Clausius-Clapeyron equation and a measured vapor pressure of 0.007 mm Hg at 100 deg C(1,SRC). Based on this vapor pressure value, Amiben may exist in the particulate or the vapor phase in the ambient atmosphere . Vapor phase Amiben will degrade relatively rapidly in the atmosphere by reaction with photochemically produced hydroxyl radicals (estimated half-life of about 15 hrs)(3,SRC). Particulate phase Amiben may be subject to rapid photodegradation .
Drinking Water Impact GROUNDWATER: Amiben was detected in 1 Wisconsin well at a concentration exceeding the recommended health advisory of 10 ug/L . According to a Wisconsin groundwater monitoring study, Amiben was detected in 2% of the wells studied at a maximum concentration of 50 ug/L . Also, Amiben detection in groundwater was reported in Iowa, but no concns were given . Amiben was detected in wells from 12 of 91 farms during November and December, 1984 in Southern Ontario, Canada . 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 . DRINKING WATER: Amiben has been qualitatively identified in drinking water from Seattle, WA on November 15, 1976 .

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