Mesotrione

Mesotrione
Names
IUPAC name
2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione
Preferred IUPAC name
2-[4-(Methylsulfonyl)-2-nitrobenzoyl]cyclohexane-1,3-dione
Other names
ZA1296
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
  • CS(=O)(=O)c1ccc(c(c1)[N+](=O)[O-])C(=O)C2C(=O)CCCC2=O
Properties[1]
C14H13NO7S
Molar mass 339.32 g·mol−1
Appearance Yellow to tan coloured solid
Density 1.49 g/cm3
Melting point 165.3 °C (329.5 °F; 438.4 K)
1500 mg/L (20 °C)
log P 0.11
Acidity (pKa) 3.12
Hazards[2]
GHS labelling:
GHS09: Environmental hazard
Warning
H410
P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Mesotrione is a selective herbicide used mainly in maize crops.[1] 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)[3] and is sold under brand names including Callisto and Tenacity. It was first marketed by Syngenta in 2001.[4]

  1. ^ a b Pesticide Properties Database. "Mesotrione". University of Hertfordshire.
  2. ^ PubChem Database. "Mesotrione".
  3. ^ Moran, GR (Jan 2005). "4-Hydroxyphenylpyruvate dioxygenase" (PDF). Archives of Biochemistry and Biophysics. 433 (1): 117–28. doi:10.1016/j.abb.2004.08.015. PMID 15581571. Archived from the original (PDF) on 2014-03-03.
  4. ^ Uttley, Nigel (June 3, 2011). "Product Profile: Mesotrione". AgriBusiness global. Retrieved 2020-03-28.