Metamitron
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Basic information
- CAS
41394-05-2- Standard SMILES
Cc1nnc(-c2ccccc2)c(=O)n1N- InChIKey
VHCNQEUWZYOAEV-UHFFFAOYSA-N- Molecular formula
- C10H10N4O
- Average molar mass
- 202.21 g/mol
- Monoisotopic mass
- 202.08546096
Overview
Metamitron is 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. It has a role as a herbicide, a xenobiotic and an environmental contaminant.
Names & identifiers
- Preferred name
- Metamitron
- IUPAC
- 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5-one
- English name
- Metamitron
- Molecular formula
- C10H10N4O
- Molecular weight
- 202.21
Names & synonyms
METAMITRON41394-05-2Goltix4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one1,2,4-Triazin-5(4H)-one, 4-amino-3-methyl-6-phenyl-DTXSID7047568H69RGO1QO64-Amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-oneCHEBI:6791DTXCID5027568RefChem:156784255-349-3
Show more names
drw1139BAY 6676GountdownCountdownbay-drw1139
4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5-oneHerbrakMetamitonMetamitron [German]MethiamitronDRW 1139BAY-DRW 1139MFCD00055524
Database identifiers
- CAS
41394-05-2- PubChem CID
- 38854
- DTXSID
DTXSID7047568- ChEMBL
CHEMBL3187145- ChEBI
CHEBI:6791- UNII
- H69RGO1QO6
- EC Number
- 255-349-3
- Nikkaji
- J15.827E
Properties
Computed structural propertiesFilling in
- XLogP
- 0.7
- Topological polar surface area
- 71.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 328
Experimental & physicochemical properties
Pesticides
Herbicides
Active substance -> EU Pesticides database: Approved
Herbicides
Environmental transformation -> Pesticides (parent, predecessor)
Pesticides -> Herbicides -> Triazinone herbicides
Pesticide (Metamitron) -> USDA PDB
LogP
0.83
0.98
Density600 kg/m³
SolubilitySolubility in water, g/100ml at 20 °C: 0.17 (slightly soluble)
Human DrugsPharmaceuticals
Melting Point167 °C
Vapor PressureVapor pressure, Pa at 20 °C: 0.00000086
Physical DescriptionCOLOURLESS-TO-YELLOW CRYSTALS.
Ionization Efficiency
Positive
3.2
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Warning
H302+H332 (34.3%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]
P261, P264, P270, P271, P273, P301+P317, P304+P340, P317, P330, P391, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Commission Regulation (EC) No 1490/2002
2008/125, Reg. (EU) 2017/195, Reg. (EU) 2022/708, Reg. (EU) 2023/1446, Reg. (EU) No 540/2011
Metamitron: HSNO Approval: HSR003442 Approved with controls
Fire HazardsGives off irritating or toxic fumes (or gases) in a fire.
EC ClassificationSymbol: Xn, N; R: 22-50; S: (2)-61
Chemical DangersDecomposes on heating. This produces toxic fumes including nitrogen oxides.
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity - category 4
Acute toxicity (Oral) - Category 4
Acute Tox. 4 *
Safety & protection
Fire FightingIn case of fire in the surroundings, use appropriate extinguishing media.
First Aid Measures
Chemistry & industry
Uses & manufacturing
Use Classification
Pesticides -> Herbicides -> Triazinone herbicides
Herbicides
Environmental transformation -> Pesticides (parent, predecessor)
Pharmaceuticals
Applications
DescriptionMetamitron 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.
UsesHerbicide.
General Description4-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.
Additional notes
DefinitionChEBI: 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.
Related reactions
3 records
Compound notes
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