| Identification | More | [Name]
Metamitron | [CAS]
41394-05-2 | [Synonyms]
1-Naphthalenol methylcarbamate
1-naphthol methylcarbamate
3-methyl-4-amino-6-phenyl-1,2,4-triazin-5(4h)-one
4-AMINO-3-METHYL-6-PHENYL-1,2,4-TRIAZIN-5-ONE
4-AMINO-3-METHYL-6-PHENYL-1,2,4-TRIAZINE-5-(4H)-ONE
Arylam
bug master
carbamine
carbatox
Carbomate
carpolin
Carylderm
cekubaryl
Clinicide
denapon
Derbac
devicarb
Dicarbam
GOLTIX
hexavin | [EINECS(EC#)]
255-349-3 | [Molecular Formula]
C10H10N4O | [MDL Number]
MFCD00055524 | [Molecular Weight]
202.21 | [MOL File]
41394-05-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
165-170 °C | [Boiling point ]
340.33°C (rough estimate) | [density ]
1.2165 (rough estimate) | [refractive index ]
1.6300 (estimate) | [Fp ]
11 °C | [storage temp. ]
APPROX 4°C
| [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
1.54±0.20(Predicted) | [color ]
White to Light yellow | [Water Solubility ]
1.8g/L(20 ºC) | [λmax]
312nm(CH3CN)(lit.) | [Merck ]
13,5949 | [BRN ]
613129 | [Henry's Law Constant]
1.0×106 mol/(m3Pa) at 25℃, Barcelo and Hennion (1997) | [InChI]
1S/C10H10N4O/c1-7-12-13-9(10(15)14(7)11)8-5-3-2-4-6-8/h2-6H,11H2,1H3 | [InChIKey]
VHCNQEUWZYOAEV-UHFFFAOYSA-N | [SMILES]
CC1=NN=C(c2ccccc2)C(=O)N1N | [CAS DataBase Reference]
41394-05-2(CAS DataBase Reference) | [NIST Chemistry Reference]
1,2,4-Triazin-5(4h)-one, 4-amino-3-methyl-6-phenyl-(41394-05-2) | [EPA Substance Registry System]
41394-05-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N,T,F | [Risk Statements ]
R22:Harmful if swallowed.
R50:Very Toxic to aquatic organisms.
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
2
| [RTECS ]
XZ3015000
| [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29336990 | [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 2 Inhalation
Acute Tox. 3 Dermal
Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1 | [Toxicity]
LD50 orally in male, female rats, male, female mice: 3343, 1832, 1450, 1463 mg/kg; dermally in rats: >500 mg/kg; LC50 (4 hr) in rats, mice, hamsters (mg/m3): >331, >206, >206 by inhalation (Lembrich) |
| Hazard Information | Back Directory | [Description]
Metamitron is a widely used herbicide. It is highly soluble in water and is not considered to be highly volatile. It can be moderately persistent in some soil systems depending on local conditions. Metamitron may also be persistent in aquatic systems. Generally, it is quite toxic to most fauna and flora. Metamitron is moderately toxic to mammals if ingested, is an endocrine disruptor and may be a thyroid toxicant. | [Chemical Properties]
Phenazinone pure product is colorless and odorless crystal, melting point 166.6°C. Vapor pressure 8.6×10-4mPa(20°C), 2×10-3mPa(25°C). Vapor pressure 8.6×10-4mPa(20℃),2×10-3mPa(25℃).KowIgP=0.83,Henry's constant 1×10-7Pa-m /mol(20℃),density 1.35g/cm3(22.5℃C). Solubility(20℃,g/L):water1.7,isopropanol5.7,methanol23,ethanol1.1,dichloromethane30~50,hexane＜0.1,cyclohexanone10~50,toluene2.8,chloroform29.Stability: stable in acid,unstable in strong base(pH>10).DT50(22℃): 410d(pH 4),740h(pH 7) , 230h (pH 9). Photolysis was very rapid at the soil surface and more rapid in water. | [Uses]
Herbicide. | [Definition]
ChEBI: A member of the class of 1,2,4-triazines that is 1,2,4-triazin-5(4H)-one substituted by an amino group at position 4, a methyl group at position 3 and a phenyl group at position 6. | [Production Methods]
Metamitron is commercially produced through a chemical synthesis that builds on the triazinone structure, derived from cyanuric chloride or similar triazine precursors. The process involves substitution reactions where methyl, amino, and phenyl groups are introduced at specific positions on the triazine ring to form the active herbicidal compound. | [General Description]
4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5-one, commonly known as metamitron, is a pesticide having low polarity and is hydrophobic in nature. Its pKa value is 2.9. | [Agricultural Uses]
Herbicide: Metamitron is a selective systemic herbicide that is
absorbed through roots and leaves and inhibits photosynthesis. It is used to control grasses and broadleaf weeds
in sugar beets and fodder beets. Not currently registered
in the U.S. Used in most European countries and having
34 global suppliers
. | [Trade name]
BAY 6676®; BAY-DRW 1139®; DRW
1139®; GALAHAD®; GOLDBEET®; GOLTIX®;
GOLTIX® 90; GOLTIX® SUPER; GOLTIX® WG;
MM 70®; HERBRAK®; MARQUISE®; SKATER®;
TORERO® (metamitron + ethofumesate) | [Mechanism of action]
Selective, systemic, absorbed mainly by roots and translocated. Inhibits photosynthesis (photosystem II). | [Metabolic pathway]
Degradation of metamitron by photolysis is strongly
dependent on solvents and oxygen, and no
photoreaction is found in methanol, acetonitrile, and
hexane, nor in oxygen-free water. In water solution,
photolytic degradation occurs and results in the
formation of desaminometamitron and a ring-opening
polar benzoylacetyl hydrazine (tentatively assigned). | [Pesticide Type]
Herbicide |
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