133-90-4 Usage
Uses
Used in Agriculture:
Chloramben is used as a preemergence or preplant herbicide for controlling annual broad-leaved weeds and grasses in various vegetable and field crops. It is also used for postemergent control of common ragweed, redroot pigweed, smartweed, and velvet-leaf.
Chloramben is used as a herbicide for grasses and broadleaf weeds, mostly on soybeans, and also on corn, beans, asparagus, pumpkins, peanuts, sunflowers, peppers, cotton, sweet potatoes, squash, melons, hardwood trees, and some conifers. However, it is not approved for use in EU countries and not registered for use in the U.S.
Used in Analytical Chemistry:
Chloramben may be used as an analytical reference standard for the determination of the analyte in water samples using liquid chromatography with electrochemical detection (LC-EC).
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 133-90-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 3 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 133-90:
(5*1)+(4*3)+(3*3)+(2*9)+(1*0)=44
44 % 10 = 4
So 133-90-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H5Cl2NO2/c8-3-1-4(7(11)12)6(9)5(10)2-3/h1-2H,10H2,(H,11,12)/p-1
133-90-4Relevant articles and documents
Herbicidal 3-(substituted-benzyl)-1-methyl-6-trifluoromethyluracils
-
, (2008/06/13)
Herbicidal 3-(substituted-benzyl)-1-methyl-6-trifluoromethyluracils, compositions containing them, and methods of using them to control undesired plant growth, including use to control weeds in certain crops, are disclosed. The herbicidal compounds of the present invention are defined by the following generic structure: STR1 in which V is hydrogen, halogen, nitro, amino, alkoxy, alkyl, cyano, phenyl, alkylcarbonylamino, alkylsulfinyl, or haloalkyl; W is hydrogen, halogen, alkyl, alkoxy, alkylaminocarbonyl, propargyloxy, cyano, nitro, benzoyl, aminooxycarbonyl, alkylsulfonyl, alkoxyiminoalkyl, alkylthio or alkylsulfinyl; X is hydrogen, chlorine, alkoxy, nitro, or amino; Y is hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl, alkenyl, acyl, epoxyalkyl, cyano, alkylaminocarbonyl, carboxy, formyl, hydroxy, hydroxyalkyl, haloalkylsulfonyloxy, benzoyl, aminooxycarbonyl, alkoxycarbonyl, propargyloxy, alkylsulfonyl, alkylsulfinyl, alkoxyiminoalkyl, or dialkylaminocarbonylthio; X and Y taken together are --OCH2 O-- or --OC(CH3)2 O--, where halogen is bromine, chlorine, fluorine, or iodine, and each aliphatic moiety has one to three carbon atoms.
Herbicidal 3-(substituted-benzyl)-1-methyl-6-trifluoromethyluracils
-
, (2008/06/13)
Herbicidal 3-(substituted-benzyl)-1-methyl-6-trifluoromethyluracils, compositions containing them, and methods of using them to control undesired plant growth, including use to control weeds in certain crops, are disclosed. The herbicidal compounds of the present invention are defined by the following generic structure: STR1 in which V is hydrogen or halogen; W is hydrogen, halogen, lower alkoxy, lower alkylaminocarbonyl, propargyloxy, or cyano; X is hydrogen or chlorine; and Y is hydrogen, halogen, cyano, lower alkylaminocarbonyl, or carboxy.
Process of improving activity of herbicides and fertilizers using N-(2-hydroxyethyl)-acetamide or -propanamide
-
, (2008/06/13)
The invention is related to the use of certain water-soluble compounds known as such and having the Formula for the modulation of membrane dependent metabolism processes within living cells, in particular with relation to transport phenomena and cell procedures which are induced or influenced by active agents supplied from outside the cell, products containing these substances for the above described uses and processes using these products.
Agricultural sulfonamides
-
, (2008/06/13)
N-(heterocyclicaminocarbonyl)arylsulfonamides in which the aryl radical is substituted in the 2-position by a carboxy radical, ester, thioester, or amide thereof; e.g. N-[(4,6-dimethylpyrimidin-2-yl)-aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide or N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.
Controlled release pesticides
-
, (2008/06/13)
Controlled release pesticide-polymers are prepared by reacting a polymer having a pendant group containing a reactive hydrogen with a chloroformamide derivative of a pesticide. In a preferred embodiment, metribuzin chloroformamide is prepared by reacting metribuzin with phosgene at a temperature of about 40° C. The metribuzin chloroformamide is then reacted with cellulose to form a pesticide-polymer from which the metribuzin is released under use conditions by hydrolytic degradation of the carbamate bond attaching the metribuzin to the polymer.
Water-degradable esters and process for the preparation thereof
-
, (2008/06/13)
Water-degradable compounds formed from amine-type compounds, aldehydes and aromatic carboxylic acids, the respective components reacting to form a complex ester which upon contact with water slowly degrades to release, at least, the original carboxylic acid.
Pesticide-polymer systems prepared from vinyl monomers
-
, (2008/06/13)
Controlled release pesticide-polymer systems are prepared by the polymerization of vinyl monomers containing pendant pesticides. The vinyl monomers are prepared by reacting an acrylic acid derivative with a pesticide or a pesticide derivative having an active hydrogen. The pesticide-polymer systems prepared from the pesticide vinyl monomers release the active pesticide material by hydrolysis or chemical depolymerization under conditions of use.
Sulfonylmethylamino-substituted benzoic acids and herbicidal method therewith
-
, (2008/06/13)
Novel benzoic acid compounds of the formula STR1 in which R is alkyl or substituted alkyl of up to 6 carbon atoms, where the substituents are selected from halogen, or R is aryl which is optionally substituted by halogen and/or by alkyl of up to 4 carbon atoms, R1 is alkyl, alkoxy or alkylmercapto, of in each case up to 4 carbon atoms, or halogen, R2 is hydrogen, R3 is hydrogen or halogen, R4 is hydroxyl, alkoxy of 1 to 6 carbon atoms or an amino group which is optionally substituted by one or two alkyl radicals each of up to 6 carbon atoms, and R5 is halogen or alkyl of up to 4 carbon atoms; are outstandingly effective and selective as herbicides.
