Metamitron

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:6791 ;
ChEMBL	ChEMBL3187145;
ChemSpider	35563;
ECHA InfoCard	100.050.301
EC Number	255-349-3;
KEGG	C10930;
PubChem CID	38854;
RTECS number	XZ3015000;
UNII	H69RGO1QO6 ;
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
Density	600 kg/m3
Melting point	167 °C (333 °F; 440 K)
Solubility in water	0.17% (20 °C)
Vapor pressure	0.00000086 Pa (20 °C)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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 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]

References

^ ^a ^b ^c ^d ^e ^f "Metamitron". pubchem.ncbi.nlm.nih.gov.
^ ^a ^b Mechant, Els (January 2011). Metamitron resistant Chenopodium album: characterisation, detection and distribution in Belgian sugar beet. Ghent, Belgium: Ghent University. p. 247. ISBN 978-90-5989-460-0. Retrieved 5 January 2024.
^ ^a ^b "Metamitron - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 5 January 2024.
^ "GOLTIX® 70 SC | ADAMA". www.adama.com. 4 October 2021. Retrieved 5 January 2024.
^ "Global Herbicide Classification Lookup". Herbicide Resistance Action Committee. Retrieved 5 January 2024.
^ ^a ^b Thiel, Heike; Kluth, Christian; Varrelmann, Mark (September 2010). "A new molecular method for the rapid detection of a metamitron-resistant target site in Chenopodium album". Pest Management Science. 66 (9): 1011–1017. doi:10.1002/ps.1975. PMID 20730994. Retrieved 6 January 2024.