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 (2011). Metamitron resistant Chenopodium album: characterisation, detection and distribution in Belgian sugar beet (Thesis). Ghent University. hdl:1854/LU-1898822. ISBN 978-90-5989-460-0.^{[page needed]}
^ ^a ^b Heri, Walter; Carroll, Beth; Parshley, Thomas; Nabors, James B. (2008). "Production, Development, and Registration of Triazine Herbicides". The Triazine Herbicides. pp. 31–43. doi:10.1016/B978-044451167-6.50006-4. ISBN 978-0-444-51167-6. In the mid-1970s, Bayer launched metamitron under the trade name Goltix®. Metamitron has application timing flexibility and can be applied both preemergence and postemergence. One of the mainstays in sugar beet production, metamitron is currently sold in more than 25 countries, with the top five being Germany, France, Netherlands, United Kingdom/Ireland, and Belgium.
^ "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.