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Mesotrione

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Mesotrione
Names
IUPAC name
2-[4-(Methylsulfonyl)-2-nitrobenzoyl]cyclohexane-1,3-dione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.111.661 Edit this at Wikidata
UNII
  • InChI=1S/C14H13NO7S/c1-23(21,22)8-5-6-9(10(7-8)15(19)20)14(18)13-11(16)3-2-4-12(13)17/h5-7,13H,2-4H2,1H3 checkY
    Key: KPUREKXXPHOJQT-UHFFFAOYSA-N checkY
  • InChI=1/C14H13NO7S/c1-23(21,22)8-5-6-9(10(7-8)15(19)20)14(18)13-11(16)3-2-4-12(13)17/h5-7,13H,2-4H2,1H3
    Key: KPUREKXXPHOJQT-UHFFFAOYAN
  • O=C(c1ccc(cc1[N+]([O-])=O)S(=O)(=O)C)C2C(=O)CCCC2=O
Properties
C14H13NO7S
Molar mass 339.32 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Mesotrione is an herbicide sold under the brand names Callisto and Tenacity that was brought to market by Syngenta in 2001.[1] It is a synthetic analog of leptospermone developed to mimic the effects of this natural herbicide.[2] Mesotrione is a member of the class of HPPD inhibitors, which all work by inhibiting the plant enzyme 4-hydroxyphenylpyruvate dioxygenase.[3] In plants, HPPD is necessary for carotenoid biosynthesis; carotenoids in turn protect chlorophyll from being degraded by sunlight.[4] When an HPPD inhibitor is sprayed on a plant, it prevents carotenoid from being made, chlorophyll degrades and the plant dies.

Sales by Syngenta were more than $400 million per year in 2011 but worldwide patent rights started to expire in 2012, opening the market to generic competition.[1]

See also

References

  1. ^ a b Dr. Nigel Uttley for Farm Chemicals International. June 3, 2011 Product Profile: Mesotrione
  2. ^ Derek Cornes (2005). "Callisto: a very successful maize herbicide inspired by allelochemistry". Fourth World Congress on Alleopathy. The Regional Institute Ltd. Retrieved May 26, 2011.
  3. ^ Moran, GR (Jan 2005). "4-Hydroxyphenylpyruvate dioxygenase" (PDF). Arch Biochem Biophys. 433 (1): 117–28. doi:10.1016/j.abb.2004.08.015. PMID 15581571. Archived from the original (PDF) on 2014-03-03.
  4. ^ "Tenacity Herbicide". Syngenta.
  • Mesotrione in the Pesticide Properties DataBase (PPDB)
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