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85-00-7

85-00-7 Structure

85-00-7 Structure
IdentificationMore
[Name]

Diquat dibromide
[CAS]

85-00-7
[Synonyms]

DIQUAT DIBROMIDE D4
1,1’-aethylen-2,2’-bipyridinium-dibromid
1,1’-aethylen-2,2’-bipyridium-dibromid[qr]
1,1’-ethylene-2,2’-bipyridiniumdibromide[qr]
1,1’-ethylene-2,2’-bipyridyliumdibromide
1,1’-ethylene-2,2’-bipyridyliumdibromide[qr]
1,1’-ethylene-2,2’-dipyridyliumdibromide
1,1-ethylene-2,2’-bipyridyliumdibromide
1,1-ethylene2,2-dipyridyliumdibromide[qr]
1’-c)pyrazinediium,6,7-dihydro-2dibromide
2,1c)pyraziniumdibromide
2,1c)pyraziniumdibromide[qr]
2’,1’-c)pyrazinediium,6,7-dihydro-dipyrido(dibromide
2’,1’-c)pyrazinediumdibromide
2’,1’-c)pyrazinediumdibromide[qr]
2-a:2’,1’-c)pyrazinediium,6,7-dihydro-dipyrido(dibromide[qr]
2-a:2’,1’-c]pyrazinediium,6,7-dihydro-dipyrido[dibromide
5,6-dihydro-dipyrido(1,2a
6,7-dihydropyrido(1,2-a
9,10-dihydro-8a,10,-diazoniaphenanthrenedibromide
[EINECS(EC#)]

201-579-4
[Molecular Formula]

C12H12Br2N2
[MDL Number]

MFCD01074187
[Molecular Weight]

344.05
[MOL File]

85-00-7.mol
Chemical PropertiesBack Directory
[Melting point ]

337°C
[density ]

1.25
[vapor pressure ]

0Pa at 25℃
[refractive index ]

1.6800 (estimate)
[storage temp. ]

-20°C
[solubility ]

DMSO (Slightly), Water (Slightly)
[form ]

Crystals
[color ]

Pale yellow
[Water Solubility ]

Soluble. 70 g/100 mL
[Henry's Law Constant]

7.0×107 mol/(m3Pa) at 25℃, HSDB (2015)
[Exposure limits]

TLV-TWA 0.5 mg/m3 (ACGIH and MSHA).
[Stability:]

Hygroscopic
[LogP]

-4.6 at 20℃
[CAS DataBase Reference]

85-00-7(CAS DataBase Reference)
[EPA Substance Registry System]

85-00-7(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Health Hazard (GHS08)Environment (GHS09)Skull and Crossbones (GHS06)
GHS08,GHS09,GHS06
[Signal word ]

Danger
[Hazard statements ]

H319-H335-H410-H315-H302-H372-H317-H330
[Precautionary statements ]

P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P273-P391-P501-P260-P264-P270-P314-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501
[Hazard Codes ]

T
[Risk Statements ]

R21:Harmful in contact with skin.
R25:Toxic if swallowed.
[Safety Statements ]

S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[OEB]

C
[OEL]

TWA: 0.5 mg/m3
[RIDADR ]

UN 2781/2811
[REACH Registrations]

Active
[HazardClass ]

6.1(a)
[PackingGroup ]

II
[Safety Profile]

Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Experimental teratogenic and reproductive effects. A skin and eye irritant. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NOx, and Br-. See also PARAQUAT
[Hazardous Substances Data]

85-00-7(Hazardous Substances Data)
[Toxicity]

LC50 (96-hour) for rainbow trout 21 mg/L, mirror carp 67 mg/L (Worthing and Hance, 1991), fathead minnow 14 mg/L, largemouth bass 7.8 mg/L (Surber and Pickering, 1962), bluegill sun?sh 35 mg/L, walleye 2.1 mg/L (Gilderhus, 1967) and striped bass 0.25 ppm (Wellborn, 1969); LC50 (96-hour) for northern pike 16 mg/L, rainbow trout 11.2 mg/L (Gilderhus, 1967); acute oral LD50 for rats is 230 mg/kg (Ashton and Monaco, 1991), 120 mg/kg (RTECS, 1985).
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

diquat(85-00-7).msds
Hazard InformationBack Directory
[Description]

Diquat (DQ) is a bipyridyl herbicide that has been in use since the 1950s. It is employed as a general use herbicide that is fast acting and nonselective. Additionally, on average, 90% of DQ consumption is reported in North America, Europe, Australia, and Japan.
[Chemical Properties]

Pale yellow crystals; forms monohydrate; mp320°C (608 °F) (decomposes); readily solublein water, insoluble in organic solvents; stablein acids or neutral solution.
[Uses]

Diquat Dibromide is a herbicidal desiccant.
[Uses]

DQ is used in a manner similar to paraquat. It is found predominantly as a mixture with paraquat, sold as Weedol and Pathclear. The most widely used formulation of DQ alone, Reglone, is an aqueous solution containing 200 g l-1 DQ dibromide. Besides the use as a general weed control agent on noncrop land, DQ is used as a preharvest desiccant on crops such as cotton, flax, and alfalfa. Additionally, almost one-third of all DQ sold is used to control emergent and subemergent aquatic weeds.
[Uses]

Nonselective contact herbicide used to control broad-leaved weeds in fruit and vegetable crops.
[Production Methods]

The commercial production of diquat dibromide involves a multi-step process. It begins with the quaternisation of 2,2'-bipyridine with 1,2-dibromoethane in a polar solvent, such as acetonitrile, under controlled temperature and pressure to form the cyclic ethylene-bridged bipyridylium structure. The reaction mixture is then treated with bromide salts to ensure the dibromide form.
[Health Hazard]

The acute toxicity of diquat dibromide ismoderate to high in most species. In domes-tic animals, its toxicity is greater than thatin small laboratory animals. The oral LD50value in cows, dogs, rabbits, and mice is30, 187, 188, and 233 mg/kg, respectively.The symptoms of acute toxicity are somnolence, lethargy, pupillary dilation, and respiratory distress. Prolonged exposure to thiscompound produced cataracts in experimental animals. Intratracheal administration ofdiquat dibromide in rats showed toxic effectsin the lung and caused lung damage (Manabeand Ogata 1986). But when administered byoral or intravenous routes, there was no toxiceffect on the lung.
[Flammability and Explosibility]

Notclassified
[Mechanism of action]

Non-selective, contact absorbed through foliage, some desiccant action. Photosystem I (electron transport) inhibitor.
[Environmental Fate]

Biological. Under aerobic and anaerobic conditions, the rate of diquat mineralization in eutrophic water and sediments was very low. After 65 days, only 0.88 and 0.21% of the applied amount (5 μg/mL) evolved as carbon dioxide (Simsiman and Chesters, 1976). Diquat is readily mineralized to carbon dioxide in nutrient solutions containing microorganisms. The addition of montmorillonite clay in an amount equal to adsorb one-half of the diquat decreased the amount of carbon dioxide by 50%. Additions of kaolinite clay had no effect on the amount of diquat degraded by microorganisms (Weber and Coble, 1968).
Photolytic. Diquat has an absorption maximum of 310 nm (Slade and Smith, 1967). The sunlight irradiation of a diquat solution (0.4 mg/100 mL) yielded 1,2,3,4-tetrahydro1-oxopyrido[1,2-a]-5-pyrazinium chloride (TOPPS) as the principal metabolite.
Chemical/Physical. Decomposes at 320°C (Windholz et al., 1983) emitting toxic fumes of bromides and nitrogen oxides (Lewis, 1990). Diquat absorbs water forming wellde?ned, pale yellow crystalline hydrate (Calderbank and Slade, 1976).
In aqueous alkaline solutions, diquat decomposes forming complex colored products including small amounts of dipyridone (Calderbank and Slade, 1976).
[Toxicity evaluation]

DQ is a dipyridyl compound that is capable of redox cycling. DQ can become reduced to produce a free radical. It can then transfer this electron to molecular oxygen to yield superoxide anion. This redox cycling mechanism allows DQ to generate reactive oxygen species (ROS) resulting in oxidative stress, damage to cellular macromolecules and even cell death. Due to its standard redox potential (E0), DQ is more likely to accept an electron compared to paraquat. Because of this property, DQ is expected to generate greater amounts of ROS compared to paraquat at equivalent concentrations. In vitro studies have shown that DQ is dependent on mitochondrial complex I and III in isolated mitochondria and primarily complex III in midbrain neuronal cultures for ROS production. DQ treatment can lead to NADPH depletion, lipid peroxidation, alteration in intracellular redox status, and liberation of ferritin-bound iron stores.
[Pesticide Type]

Herbicide
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

85-00-7(sigmaaldrich)
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