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
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 Y
    Key: KPUREKXXPHOJQT-UHFFFAOYSA-N Y
  • CS(=O)(=O)c1ccc(c(c1)[N+](=O)[O-])C(=O)C2C(=O)CCCC2=O
Properties
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
GHS labelling:
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).
Infobox references

Mesotrione is a selective herbicide used mainly in maize crops and has also been shown to have weak insecticidal properties. 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.