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 |
|
3D model (JSmol) |
|
ChEBI |
|
ChEMBL |
|
ChemSpider |
|
ECHA InfoCard | 100.050.301 |
EC Number |
|
KEGG |
|
PubChem CID |
|
RTECS number |
|
UNII |
|
CompTox Dashboard (EPA) |
|
InChI
| |
| |
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 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
- ^ 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.
- v
- t
- e
- acetochlor
- alachlor
- asulam
- benfluralin
- butachlor
- diethatyl
- diflufenican
- dimethenamid
- flamprop
- metazachlor
- metolachlor
- oryzalin
- pendimethalin
- pretilachlor
- propachlor
- propanil
- trifluralin
- aminopyralid
- chloramben
- clopyralid
- dicamba
- picloram
- pyrithiobac
- quinclorac
- quinmerac
- cacodylic acid
- copper arsenate
- DSMA
- MSMA
- flurochloridone
- isoxaflutole
- leptospermone
- mesotrione
- nitisinone
- sethoxydim
- sulcotrione
- bensulide
- bialaphos
- ethephon
- fosamine
- glufosinate
- glyphosate
- piperophos
Auxins | |||||
---|---|---|---|---|---|
ACCase inhibitors |
|
Nitrophenyl ethers | |
---|---|
Pyrimidinediones | |
Triazolinones |
|
- dithiopyr
- fluroxypyr
- imazapyr
- thiazopyr
- triclopyr
Photosystem I inhibitors |
---|
Photosystem II inhibitors |
|
---|
Photosystem II inhibitors |
|
---|---|
ALS inhibitors |