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
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
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.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Mesotrione: a new selective herbicide for use in maize. | 2001 Feb |
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Determination of mesotrione residues and metabolites in crops, soil, and water by liquid chromatography with fluorescence detection. | 2002 Jul 3 |
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Adsorption and degradation of the weak acid mesotrione in soil and environmental fate implications. | 2002 Mar-Apr |
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Soil activity and persistence of sulcotrione and mesotrione. | 2004 |
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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 |
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Biotransformation of the triketone herbicide mesotrione by a Bacillus strain. Metabolite profiling using liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry. | 2006 |
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First isolation and characterization of a bacterial strain that biotransforms the herbicide mesotrione. | 2006 Aug |
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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 |
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Photodegradation of sulcotrione in various aquatic environments and toxicity of its photoproducts for some marine micro-organisms. | 2007 Apr |
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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 |
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The economics of atrazine. | 2007 Oct-Dec |
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Interactions between population density of the Colorado potato beetle, Leptinotarsa decemlineata, and herbicide rate for suppression of solanaceous weeds. | 2008 |
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Behaviour of sulcotrione and mesotrione in two soils. | 2008 Jan |
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Lemna minor L. as a model organism for ecotoxicological studies performing 1H NMR fingerprinting. | 2009 Aug |
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Effect of a spreading adjuvant on mesotrione photolysis on wax films. | 2009 Oct 28 |
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Optoelectronic capillary sensors in microfluidic and point-of-care instrumentation. | 2010 |
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Methyl 4-methyl-sulfonyl-2-nitro-benzoate. | 2010 Jun 16 |
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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 Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11488774
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28941309
Mesotrione inhibited recombinant AtHPPD with IC50 value of 0.252 uM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:58:29 UTC 2023
by
admin
on
Fri Dec 15 17:58:29 UTC 2023
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Record UNII |
48TR68G21T
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Record Status |
Validated (UNII)
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Record Version |
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EPA PESTICIDE CODE |
122990
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175967
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MESOTRIONE
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m7252
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C432907
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mesotrione
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ANNEX I INDEX 609-064-00-X
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268548-24-9
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ALTERNATIVE |