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Chloramben

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Chloramben Basic information

Product Name:
Chloramben
CAS:
133-90-4
MF:
C7H5Cl2NO2
MW:
206.03
EINECS:
205-123-5
Mol File:
133-90-4.mol
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Chloramben Chemical Properties

Melting point:
200 °C
Boiling point:
312 °C
Density 
1.4062 (rough estimate)
refractive index 
1.6100 (estimate)
storage temp. 
0-6°C
pka
2.75±0.25(Predicted)
form 
Powder
Water Solubility 
700 mg/L (25 ºC)
Merck 
13,2082
BRN 
2365906
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)
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Safety Information

Hazard Codes 
T,Xn
Risk Statements 
45-36/37/38-40
Safety Statements 
53-22-26-36/37/39-45-36
RIDADR 
UN 3077 9/PG 3
WGK Germany 
3
RTECS 
DG1925000
HS Code 
29224999
Hazardous Substances Data
133-90-4(Hazardous Substances Data)
Toxicity
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).

MSDS

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Chloramben Usage And Synthesis

Chemical Properties

Off-white to beige powder

Chemical Properties

Chloramben is a colorless, odorless, crystalline solid.

Uses

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.

Uses

Herbicide or plant growth regulator.

General Description

Purplish white powder or light purple solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Chloramben reacts with sodium hypochlorite solutions .

Health Hazard

ACUTE/CHRONIC HAZARDS: Chloramben emits toxic fumes when heated to decomposition.

Fire Hazard

Flash point data for Chloramben is not available, but Chloramben is probably combustible.

Agricultural Uses

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

Trade name

ACP-M-728®; AMBEN®; AMBIBEN®; AMIBEN®[C]; AMIBIN®; AMOBEN®; ORNAMENTAL WEEDER®[C]; VEGABEN®; VEGIBEN®[C]; WEEDONE® GARDEN WEEDER

Potential Exposure

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.

Environmental Fate

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.

Metabolism

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.

Shipping

UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Toxicity evaluation

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.

Incompatibilities

Rapidly decomposed by light. Strong acids and acid fumes

Waste Disposal

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.

Chloramben Preparation Products And Raw materials

Raw materials

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