Metamitron

Metamitron
Skeletal formula of metamitron
Space-filling model of the metamitron molecule
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.050.301 Edit this at Wikidata
EC Number
  • 255-349-3
KEGG
RTECS number
  • XZ3015000
UNII
  • 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
  • CC1=NN=C(C(=O)N1N)C2=CC=CC=C2
Properties
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)
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).

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]

See also

References

  1. ^ a b c d e f "Metamitron". pubchem.ncbi.nlm.nih.gov.
  2. ^ 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.
  3. ^ a b "Metamitron - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 5 January 2024.
  4. ^ "GOLTIX® 70 SC | ADAMA". www.adama.com. 4 October 2021. Retrieved 5 January 2024.
  5. ^ "Global Herbicide Classification Lookup". Herbicide Resistance Action Committee. Retrieved 5 January 2024.
  6. ^ 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.