Metamitron

Metamitron is an organic compound used as a selective pre- and post-emergence herbicide in sugar beets.^[2][3] It is used in the European Union for weed suppression in sugar beets.^[3] Metamitron is marketed under the trade name Goltix by ADAMA in Europe, the United Kingdom,^[4] New Zealand, and South Africa.

Metamitron

Names
Preferred IUPAC name 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5-one
Other names Metamiton Methiamitron 4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5-one 4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one Goltix Herbrak
Identifiers
CAS Number	41394-05-2 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6791 Y
ChEMBL	ChEMBL3187145
ChemSpider	35563
ECHA InfoCard	100.050.301
EC Number	255-349-3
KEGG	C10930
PubChem CID	38854
RTECS number	XZ3015000
UNII	H69RGO1QO6 Y
CompTox Dashboard (EPA)	DTXSID7047568
InChI InChI=1S/C10H10N4O/c1-7-12-13-9(10(15)14(7)11)8-5-3-2-4-6-8/h2-6H,11H2,1H3 Key: VHCNQEUWZYOAEV-UHFFFAOYSA-N
SMILES CC1=NN=C(C(=O)N1N)C2=CC=CC=C2
Properties
Chemical formula	C10H10N4O
Molar mass	202.217 g·mol−1
Appearance	Colorless-to-yellow crystals[1]
Density	600 kg/m3
Melting point	167[1] °C (333 °F; 440 K)
Solubility in water	0.17% (20 °C)[1]
Vapor pressure	0.00000086 Pa (20 °C)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Metamitron is a triazinone herbicide. It possesses a triazine ring like other organic compounds that use cyanuric chloride as a precursor. It is a modification of the chemical 1,2,4-triazin-5(4H)-one, with methyl, amino, and phenyl group substitutions at positions 3, 4, and 6.^[1]

Metamitron is in the HRAC Mode of action Group 5.^[5] It functions as an inhibitor of PSII by binding to serine 264 on the D1 protein.^[6] Resistance to metamitron has been found in Chenopodium album growing as weeds among sugar beet fields in Belgium, caused by a mutation in serine 264.^[2][6]

Metamitron has moderate acute oral and inhalation toxicity.^[1]

See also

• Atrazine
• Hexazinone
• Metribuzin