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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Biodegradation pathway of mesotrione: complementarities of NMR, LC-NMR and LC-MS for qualitative and quantitative metabolic profiling. | 2010-09 |
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| Methyl 4-methyl-sulfonyl-2-nitro-benzoate. | 2010-06-16 |
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| The effect of mixing two herbicides mesotrione and nicosulfuron on their photochemical reactivity on cuticular wax film. | 2010-04 |
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| Optoelectronic capillary sensors in microfluidic and point-of-care instrumentation. | 2010 |
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| Effect of a spreading adjuvant on mesotrione photolysis on wax films. | 2009-10-28 |
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| Lemna minor L. as a model organism for ecotoxicological studies performing 1H NMR fingerprinting. | 2009-08 |
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| Increase in nutritionally important sweet corn kernel carotenoids following Mesotrione and atrazine applications. | 2009-07-22 |
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| Mesotrione control and pigment concentration of large crabgrass (Digitaria sanguinalis) under varying environmental conditions. | 2009-06 |
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| Liquid chromatography tandem mass spectrometry method for the quantitation of NTBC (2-(nitro-4-trifluoromethylbenzoyl)1,3-cyclohexanedione) in plasma of tyrosinemia type 1 patients. | 2009-05-15 |
|
| Isolation and characterization of mesotrione-degrading Bacillus sp. from soil. | 2009-04 |
|
| The watershed as a conceptual framework for the study of environmental and human health. | 2009-02-18 |
|
| Toxicity assessment of the herbicides sulcotrione and mesotrione toward two reference environmental microorganisms: Tetrahymena pyriformis and Vibrio fischeri. | 2008-11 |
|
| Effects of mesotrione on perennial ryegrass (Lolium perenne L.) carotenoid concentrations under varying environmental conditions. | 2008-10-08 |
|
| Behaviour of sulcotrione and mesotrione in two soils. | 2008-01 |
|
| Interactions between population density of the Colorado potato beetle, Leptinotarsa decemlineata, and herbicide rate for suppression of solanaceous weeds. | 2008 |
|
| The economics of atrazine. | 2007-12-19 |
|
| 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. | 2007-06-22 |
|
| Photodegradation of sulcotrione in various aquatic environments and toxicity of its photoproducts for some marine micro-organisms. | 2007-04 |
|
| First isolation and characterization of a bacterial strain that biotransforms the herbicide mesotrione. | 2006-08 |
|
| Simulated solar light irradiation of mesotrione in natural waters. | 2006-06-15 |
|
| Metabonomic strategy for the investigation of the mode of action of the phytotoxin (5S,8R,13S,16R)-(-)-pyrenophorol using 1H nuclear magnetic resonance fingerprinting. | 2006-03-08 |
|
| Biotransformation of the triketone herbicide mesotrione by a Bacillus strain. Metabolite profiling using liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry. | 2006 |
|
| Photosynthetic and growth responses of zea mays L and four weed species following post-emergence treatments with mesotrione and atrazinet. | 2004-11 |
|
| 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. | 2004-03-05 |
|
| Soil activity and persistence of sulcotrione and mesotrione. | 2004 |
|
| Solid-phase fluoroimmunoassay for the determination of mesotrione--a novel triketone herbicide--in water with direct measurement of the fluorescence onto the solid support. | 2003-04 |
|
| Simultaneous determination of pesticides using a four-band disposable optical capillary immunosensor. | 2002-12-01 |
|
| Activity of mesotrione on resistant weeds in maize. | 2002-09 |
|
| Determination of mesotrione residues and metabolites in crops, soil, and water by liquid chromatography with fluorescence detection. | 2002-07-03 |
|
| Adsorption and degradation of the weak acid mesotrione in soil and environmental fate implications. | 2002-04-05 |
|
| Soil persistence of 4-HPPD-inhibitors in different soil types. | 2002 |
|
| Metabolism of 2-(4-methylsulphonyl-2-nitrobenzoyl)-1,3-cyclohexanedione (mesotrione) in rat and mouse. | 2001-10 |
|
| Pharmacokinetics and pharmacodynamics of NTBC (2-(2-nitro-4-fluoromethylbenzoyl)-1,3-cyclohexanedione) and mesotrione, inhibitors of 4-hydroxyphenyl pyruvate dioxygenase (HPPD) following a single dose to healthy male volunteers. | 2001-08 |
|
| Mesotrione: a new selective herbicide for use in maize. | 2001-02 |
|
| Primus (florasulam 50 G/L), a new triazolopyrimidine sulfonanilide herbicide to control broad-leaved weeds in maize when applied in early postemergence (1 to 6 leaf stage of maize). Preliminary results. | 2001 |
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
| Substance Class |
Chemical
Created
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| Record UNII |
48TR68G21T
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| Record Status |
Validated (UNII)
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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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DTXSID7032424
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104206-82-8
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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 |