Metamitron

Last updated
Metamitron
Metamitron structure.svg
Metamitron (model).png
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
ChemSpider
ECHA InfoCard 100.050.301 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
AppearanceColorless-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

Related Research Articles

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A sugar beet is a plant whose root contains a high concentration of sucrose and which is grown commercially for sugar production. In plant breeding, it is known as the Altissima cultivar group of the common beet. Together with other beet cultivars, such as beetroot and chard, it belongs to the subspecies Beta vulgaris subsp. vulgaris but classified as var. saccharifera . Its closest wild relative is the sea beet.

<span class="mw-page-title-main">Herbicide</span> Type of chemical used to kill unwanted plants

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<span class="mw-page-title-main">Genetically modified food</span> Foods produced from organisms that have had changes introduced into their DNA

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<span class="mw-page-title-main">Pesticide resistance</span> Decreased effectiveness of a pesticide on a pest

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<span class="mw-page-title-main">Weed control</span> Botanical component of pest control for plants

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<span class="mw-page-title-main">Glyphosate</span> Systemic herbicide and crop desiccant

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Chenopodium album is a fast-growing annual plant in the genus Chenopodium. Though cultivated in some regions, the plant is elsewhere considered a weed. Common names include lamb's quarters, melde, goosefoot, wild spinach and fat-hen, though the latter two are also applied to other species of the genus Chenopodium, for which reason it is often distinguished as white goosefoot. Chenopodium album is extensively cultivated and consumed in Northern India, and Nepal as a food crop known as bathua.

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<span class="mw-page-title-main">Mesotrione</span> Chemical compound used as an herbicide

Mesotrione is a selective herbicide used mainly in maize crops. It is a synthetic compound inspired by the natural substance leptospermone found in the bottlebrush tree Callistemon citrinus. It inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD) and is sold under brand names including Callisto and Tenacity. It was first marketed by Syngenta in 2001.

<span class="mw-page-title-main">Acifluorfen</span> Chemical compound

Acifluorfen is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to acifluorfen and its salts, via metabolic disposal by glutathione S-transferase. It is effective against broadleaf weeds and grasses and is used agriculturally on fields growing soybeans, peanuts, peas, and rice.

4-Hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors are a class of herbicides that prevent growth in plants by blocking 4-Hydroxyphenylpyruvate dioxygenase, an enzyme in plants that breaks down the amino acid tyrosine into molecules that are then used by plants to create other molecules that plants need. This process of breakdown, or catabolism, and making new molecules from the results, or biosynthesis, is something all living things do. HPPD inhibitors were first brought to market in 1980, although their mechanism of action was not understood until the late 1990s. They were originally used primarily in Japan in rice production, but since the late 1990s have been used in Europe and North America for corn, soybeans, and cereals, and since the 2000s have become more important as weeds have become resistant to glyphosate and other herbicides. Genetically modified crops are under development that include resistance to HPPD inhibitors. There is a pharmaceutical drug on the market, nitisinone, that was originally under development as an herbicide as a member of this class, and is used to treat an orphan disease, type I tyrosinemia.

<span class="mw-page-title-main">Quinclorac</span> Herbicide, synthetix auxin

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A genetically modified sugar beet is a sugar beet that has been genetically engineered by the direct modification of its genome using biotechnology. Commercialized GM sugar beets make use of a glyphosate-resistance modification developed by Monsanto and KWS Saat. These glyphosate-resistant beets, also called 'Roundup Ready' sugar beets, were developed by 2000, but not commercialized until 2007. For international trade, sugar beets have a Maximum Residue Limit of glyphosate of 15 mg/Kg at harvest. As of 2016, GMO sugar beets are grown in the United States and Canada. In the United States, they play an important role in domestic sugar production. Studies have concluded the sugar from glyphosate-resistant sugar beets is molecularly identical to and so has the same nutritional value as sugar from conventional (non-GMO) sugar beets.

<span class="mw-page-title-main">Fomesafen</span> PPOi herbicide

Fomesafen is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase (PPO) which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to fomesafen, via metabolic disposal by glutathione S-transferase. As a result, soy is the most common crop treated with fomesafen, followed by other beans and a few other crop types. It is not safe for maize/corn or other Poaceae.

<span class="mw-page-title-main">Fluazifop</span> ACCase herbicide, fop, anti-grass

Fluazifop is the common name used by the ISO for an organic compound that is used as a selective herbicide. The active ingredient is the 2R enantiomer at its chiral centre and this material is known as fluazifop-P when used in that form. More commonly, it is sold as its butyl ester, fluazifop-P butyl with the brand name Fusilade.

<span class="mw-page-title-main">Indaziflam</span> Preemergent herbicide discovered in 2009

Indaziflam is a preemergent herbicide especially for grass control in tree and bush crops.

<span class="mw-page-title-main">Aclonifen</span> Chemical compound

Aclonifen is a diphenyl ether herbicide which has been used in agriculture since the 1980s. Its mode of action has been uncertain, with evidence suggesting it might interfere with carotenoid biosynthesis or inhibit the enzyme protoporphyrinogen oxidase (PPO). Both mechanisms could result in the observed whole-plant effect of bleaching and the compound includes chemical features that are known to result in PPO effects, as seen with acifluorfen, for example. In 2020, further research revealed that aclonifen has a different and novel mode of action, targeting solanesyl diphosphate synthase which would also cause bleaching.

References

  1. 1 2 3 4 5 6 "Metamitron". pubchem.ncbi.nlm.nih.gov.
  2. 1 2 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. 1 2 "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. 1 2 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.