Chloramben Chemical Properties
- Melting point:
- 200 °C
- Boiling point:
- 312 °C
- 1.4062 (rough estimate)
- refractive index
- 1.6100 (estimate)
- storage temp.
- Water Solubility
- 700 mg/L (25 ºC)
- Exposure limits
- An experimental carcinogen.
- CAS DataBase Reference
- 133-90-4(CAS DataBase Reference)
- NIST Chemistry Reference
- 3-Amino-2,5-dichlorobenzoic acid(133-90-4)
- EPA Substance Registry System
- Chloramben (133-90-4)
- Hazard Codes
- Risk Statements
- Safety Statements
- UN 3077 9/PG 3
- WGK Germany
- HS Code
- Hazardous Substances Data
- 133-90-4(Hazardous Substances Data)
- Nontoxic to fish (Hartley and Kidd, 1987); acute oral LD50 for rats 5,620 mg/kg (Hartley and Kidd, 1987), 3,500 mg/kg (RTECS, 1985).
Chloramben Usage And Synthesis
Off-white to beige powder
Chloramben is a colorless, odorless, crystalline solid.
Preemergence or preplant herbicide used in many vegetable and field crops to control annual broad-leaved weeds and grasses. Also for postemergent control of common ragweed, redroot pigweed, smartweed and velvet-leaf.
Herbicide or plant growth regulator.
Purplish white powder or light purple solid.
Air & Water Reactions
Insoluble in water.
Chloramben reacts with sodium hypochlorite solutions .
ACUTE/CHRONIC HAZARDS: Chloramben emits toxic fumes when heated to decomposition.
Flash point data for Chloramben is not available, but Chloramben is probably combustible.
Herbicide: A herbicide for grasses, and broadleaf weeds. Mostly used on soybeans, and also on corn, beans, asparagus, pumpkins, peanuts, sunflowers, peppers, cotton, sweet potatoes, squash, melons, hardwood trees, and some conifers. Not approved for use in EU countries. Not registered for use in the U.S. There are 51 global suppliers
ACP-M-728®; AMBEN®; AMBIBEN®; AMIBEN®[C]; AMIBIN®; AMOBEN®; ORNAMENTAL WEEDER®[C]; VEGABEN®; VEGIBEN®[C]; WEEDONE® GARDEN WEEDER
A General Use Pesticide (GUP) that is no longer produced or sold in the United States. It is used as an herbicide for grasses, broadleaf weeds, soybeans, beans, and some vegetables. Workers involved in the manufacture, formulation, or application of this reemergence herbicide.
Soil. In soils, chloramben was degraded by microorganisms but no products were
identified (Humburg et al., 1991). The main degradative pathway of chloramben in soil is
decarboxylation and subsequent mineralization to carbon dioxide. The calculated halflives in Ella loamy sand, Kewaunee clay and Poygan silty clay were 120–201, 182–286
and 176–314 days, respectively (Wildung et al., 1968). Persistence in soil is 6–8 weeks
(Hartley and Kidd, 1987).
Groundwater. According to the U.S. EPA (1986) and Ashton and Monaco (1991), chloramben has a high potential to leach to groundwater, especially in sandy soils during heavy rains. Plant. Degrades in plants to N-glucoside, glucose ester, conjugates and insoluble residues (Ashton and Monaco, 1991).
Photolytic. Plimmer and Hummer (1969) studied the irradiation of chloramben in water (2–4 mg/L) under a 450-W mercury vapor lamp (λ >2,800 ?) for periods of 2 to 20 hours. Chloride ion was released and a complex mixture of colored products was observed. It was postulated that amino free radicals reacted with each other via polymerization and oxidation processes. The experiment was repeated except the solution contained sodium bisulfite as an inhibitor under a nitrogen atmosphere. Oxidation did not occur and loss of the 2-chloro substituent gave 3-amino-5-chlorobenzoic acid (Plimmer and Hummer, 1969).
Chloramben (sodium salt) in aqueous solutions (100 mg/L) was rapidly photodegraded in outdoor sunlight and under a 360-W mercury arc lamp (Crosby and Leitis, 1969).
In sunlight, the solution became yellow-brown. Subsequent analysis by gas-liquid chromatography did not resolve any compounds other than chloramben. However, analysis by TLC indicated at least 12 unidentified products. These products were reportedly formed via replacement of chlorine by a hydroxy group, reductive dechlorination and abstraction of hydrogen from the amine group (oxidation). No photodegradation products could be identified in the solutions irradiated with the mercury arc lamp (Crosby and Leitis, 1969).
Chemical/Physical. Emits toxic fumes of nitrogen oxides and chlorine when heated to decomposition (Sax and Lewis, 1987). Forms water-soluble salts with alkalies.
Chloramben is generally stable to hydrolytic degradation; however, it will decompose in sodium hypochlorite solutions. It is also very sensitive to light and under oxidative conditions aqueous solutions will rapidly undergo photolysis. The predominant reaction in oxidative photolysis is unclear but appears to involve the formation of amino radicals. Photolysis also occurs under reductive conditions by dechlorination at the 2 position, i.e., when appropriate reducing agents are present, e.g., sodium bisulfite.
UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
Although limited studies are available, those that have been conducted, for example, on cows and dogs, indicate that the majority of ingested chloramben is quickly excreted through the urine and feces and does not accumulate in tissues. An interesting interaction between caffeine and chloramben suggests that they can form an insoluble complex in the intestinal tract and thus decrease the amount of chloramben absorbed into the blood stream. The acute oral LD50 in rat is >5000 mg/kg.
Rapidly decomposed by light. Strong acids and acid fumes
Chloramben is stable to heat, oxidation, and hydrolysis in acidic or basic media. The stability is comparable to that of benzoic acid. Wet oxidation or incineration are recommended disposal methods.
- 2,5-Dichloro-3-nitrobenzoic acid
- CHLORAMBEN AMMONIUM SALT)
- methyl chloramben,Chloramben methyl,CHLORAMBEN:3-AMINO-2,5-DICHLOROBENZOIC ACID,CHLORAMBEN METHYL ESTER
- methyl 2,5-dichloro-3-nitrobenzoate
- CHLORAMBEN, SODIUM SALT)
- 3,5-Dichlorobenzoic acid
- 6-Aminocaproic acid
- 3-Aminobenzoic acid
- 2,4-Dichlorobenzoic acid
- 4-Aminobenzoic acid
- 3-Amino-4-chlorobenzoic acid
- Anthranilic acid
- 2,5-Dichlorobenzoic acid
- Imazapyr acid
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