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Details

Stereochemistry ACHIRAL
Molecular Formula C14H13NO7S
Molecular Weight 339.321
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MESOTRIONE

SMILES

CS(=O)(=O)C1=CC=C(C(=O)C2C(=O)CCCC2=O)C(=C1)[N+]([O-])=O

InChI

InChIKey=KPUREKXXPHOJQT-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C14H13NO7S
Molecular Weight 339.321
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Mesotrione is a new herbicide being developed for the selective pre- and post-emergence control of a wide range of broad-leaved and grass weeds in maize (Zea mays). It is a member of the benzoylcyclohexane-1,3-dione family of herbicides, which are chemically derived from a natural phytotoxin obtained from the Californian bottlebrush plant, Callistemon citrinus. The compound acts by competitive inhibition of the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD), a component of the biochemical pathway that converts tyrosine to plastoquinone and alpha-tocopherol. Mesotrione is an extremely potent inhibitor of HPPD from Arabidopsis thaliana, with a Ki value of c 6-18 pM. Commercialization of mesotrione began with its launch in the United States, Germany and Austria in 2001. It is now available under various Syngenta trade names — Callisto, Lumax, Lexar, Halex GT, Camix, Calcris, Elumis, Calaris Callisto Xtra and Tenacity — in more than 50 countries, including Austria, Argentina, Belgium, Brazil, Bulgaria, Canada, China, Croatia, Czech Republic, France, Germany, Greece, Hungary, Ireland, Italy, Japan, Netherlands, New Zealand, Mozambique, Poland, Portugal, Romania, Russia, Slovakia, Slovenia, South Africa, Spain, Sweden, Switzerland, Turkey, the United Kingdom and the United States.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.013 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Mesotrione: a new selective herbicide for use in maize.
2001 Feb
Determination of mesotrione residues and metabolites in crops, soil, and water by liquid chromatography with fluorescence detection.
2002 Jul 3
Adsorption and degradation of the weak acid mesotrione in soil and environmental fate implications.
2002 Mar-Apr
Soil activity and persistence of sulcotrione and mesotrione.
2004
Quantification of the new triketone herbicides, sulcotrione and mesotrione, and other important herbicides and metabolites, at the ng/l level in surface waters using liquid chromatography-tandem mass spectrometry.
2004 Mar 5
Biotransformation of the triketone herbicide mesotrione by a Bacillus strain. Metabolite profiling using liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry.
2006
First isolation and characterization of a bacterial strain that biotransforms the herbicide mesotrione.
2006 Aug
Metabonomic strategy for the investigation of the mode of action of the phytotoxin (5S,8R,13S,16R)-(-)-pyrenophorol using 1H nuclear magnetic resonance fingerprinting.
2006 Mar 8
Photodegradation of sulcotrione in various aquatic environments and toxicity of its photoproducts for some marine micro-organisms.
2007 Apr
Determination of kinetic and equilibrium regimes in the operation of polar organic chemical integrative samplers. Application to the passive sampling of the polar herbicides in aquatic environments.
2007 Jun 22
The economics of atrazine.
2007 Oct-Dec
Interactions between population density of the Colorado potato beetle, Leptinotarsa decemlineata, and herbicide rate for suppression of solanaceous weeds.
2008
Behaviour of sulcotrione and mesotrione in two soils.
2008 Jan
Lemna minor L. as a model organism for ecotoxicological studies performing 1H NMR fingerprinting.
2009 Aug
Effect of a spreading adjuvant on mesotrione photolysis on wax films.
2009 Oct 28
Optoelectronic capillary sensors in microfluidic and point-of-care instrumentation.
2010
Methyl 4-methyl-sulfonyl-2-nitro-benzoate.
2010 Jun 16
Biodegradation pathway of mesotrione: complementarities of NMR, LC-NMR and LC-MS for qualitative and quantitative metabolic profiling.
2010 Sep
Patents

Sample Use Guides

In the mesotrione study, three groups, each consisting of six volunteers, were given a single oral dose of either 0.1, 0.5 or 4 mg mesotrione per kg. Each volunteer received a single dose which was administered with 100 ml of water.
Route of Administration: Oral
Mesotrione inhibited recombinant AtHPPD with IC50 value of 0.252 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:58:29 UTC 2023
Edited
by admin
on Fri Dec 15 17:58:29 UTC 2023
Record UNII
48TR68G21T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MESOTRIONE
HSDB   ISO   MI  
ISO  
Official Name English
2-CYCLOHEXEN-1-ONE, 3-HYDROXY-2-(4-(METHYLSULFONYL)-2-NITROBENZOYL)-
Systematic Name English
2-(4-MESYL-2-NITROBENZOYL)CYCLOHEXANE-1,3-DIONE
Systematic Name English
MESOTRIONE [HSDB]
Common Name English
3-HYDROXY-2-(4-(METHYLSULFONYL)-2-NITROBENZOYL)-2-CYCLOHEXEN-1-ONE
Systematic Name English
MESOTRIONE [ISO]
Common Name English
MESOTRIONE [MI]
Common Name English
2-(4-(METHYLSULFONYL)-2-NITROBENZOYL)-1,3-CYCLOHEXANEDIONE
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 122990
Created by admin on Fri Dec 15 17:58:29 UTC 2023 , Edited by admin on Fri Dec 15 17:58:29 UTC 2023
Code System Code Type Description
PUBCHEM
175967
Created by admin on Fri Dec 15 17:58:29 UTC 2023 , Edited by admin on Fri Dec 15 17:58:29 UTC 2023
PRIMARY
WIKIPEDIA
MESOTRIONE
Created by admin on Fri Dec 15 17:58:29 UTC 2023 , Edited by admin on Fri Dec 15 17:58:29 UTC 2023
PRIMARY
MERCK INDEX
m7252
Created by admin on Fri Dec 15 17:58:29 UTC 2023 , Edited by admin on Fri Dec 15 17:58:29 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID7032424
Created by admin on Fri Dec 15 17:58:29 UTC 2023 , Edited by admin on Fri Dec 15 17:58:29 UTC 2023
PRIMARY
CAS
104206-82-8
Created by admin on Fri Dec 15 17:58:29 UTC 2023 , Edited by admin on Fri Dec 15 17:58:29 UTC 2023
PRIMARY
HSDB
7250
Created by admin on Fri Dec 15 17:58:29 UTC 2023 , Edited by admin on Fri Dec 15 17:58:29 UTC 2023
PRIMARY
MESH
C432907
Created by admin on Fri Dec 15 17:58:29 UTC 2023 , Edited by admin on Fri Dec 15 17:58:29 UTC 2023
PRIMARY
ALANWOOD
mesotrione
Created by admin on Fri Dec 15 17:58:29 UTC 2023 , Edited by admin on Fri Dec 15 17:58:29 UTC 2023
PRIMARY
ECHA (EC/EINECS)
ANNEX I INDEX 609-064-00-X
Created by admin on Fri Dec 15 17:58:29 UTC 2023 , Edited by admin on Fri Dec 15 17:58:29 UTC 2023
PRIMARY
FDA UNII
48TR68G21T
Created by admin on Fri Dec 15 17:58:29 UTC 2023 , Edited by admin on Fri Dec 15 17:58:29 UTC 2023
PRIMARY
CAS
268548-24-9
Created by admin on Fri Dec 15 17:58:29 UTC 2023 , Edited by admin on Fri Dec 15 17:58:29 UTC 2023
ALTERNATIVE