mesotrione
1,3-cyclohexanedione, 2-(4-(methylsulfonyl)-2-nitrobenzoyl)-
 
Notes:
None found
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CAS Number: 104206-82-8Picture of molecule3D/inchi
Other(deleted CASRN): 207996-81-4
FDA UNII: 48TR68G21T
Nikkaji Web: J1.031.035K
Beilstein Number: 8999656
MDL: MFCD04112617
XlogP3-AA: 0.70 (est)
Molecular Weight: 339.32401000
Formula: C14 H13 N O7 S
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome, Edge or firefox)
Category: herbicides / pesticides
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 165.00 °C. @ 760.00 mm Hg (est)
Boiling Point: 643.30 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 5.690000 mmHg @ 20.00 °C. (est)
Flash Point: 649.00 °F. TCC ( 342.90 °C. ) (est)
logP (o/w): -0.700 (est)
Soluble in:
 water, 157.5 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
Mesotrione 99%
Sigma-Aldrich
For experimental / research use only.
Mesotrione PESTANAL®, analytical standard
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: herbicides / pesticides
Recommendation for mesotrione usage levels up to:
 not for fragrance use.
 
Recommendation for mesotrione flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Reasoned opinion on the review of the existing maximum residue levels (MRLs) for mesotrione according to Article 12 of Regulation (EC) No 396/2005
View page or View pdf
Peer review of the pesticide risk assessment of the active substance mesotrione
View page or View pdf
Outcome of the consultation with Member States, the applicant and EFSA on the pesticide risk assessment for mesotrione in light of confirmatory data
View page or View pdf
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 175967
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 2
 2-(4-methylsulfonyl-2-nitrobenzoyl)cyclohexane-1,3-dione
Chemidplus: 0104206828
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References:
 2-(4-methylsulfonyl-2-nitrobenzoyl)cyclohexane-1,3-dione
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 175967
Pubchem (sid): 135154089
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
HMDB (The Human Metabolome Database): Search
ChemSpider: View
Wikipedia: View
Formulations/Preparations:
trade name: callisto herbicide ...a suspension concentrate formulation containing 40% of the active ingredient.
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
1,3-cyclohexanedione, 2-(4-(methylsulfonyl)-2-nitrobenzoyl)-
2-(4-methylsulfonyl-2-nitrobenzoyl)cyclohexane-1,3-dione
(2-nitro-4-(methylsullfonyl))benzoylcyclohexane-1,3-dione
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Articles:
PubMed: Synthesis and herbicidal evaluation of triketone-containing quinazoline-2,4-diones.
PubMed: Effect of herbicide combinations on Bt-maize rhizobacterial diversity.
PubMed: Broad 4-hydroxyphenylpyruvate dioxygenase inhibitor herbicide tolerance in soybean with an optimized enzyme and expression cassette.
PubMed: Design, synthesis and herbicidal activity of novel quinazoline-2,4-diones as 4-hydroxyphenylpyruvate dioxygenase inhibitors.
PubMed: Comparison of three pesticide fate models with respect to the leaching of two herbicides under field conditions in an irrigated maize cropping system.
PubMed: Soil surface colonization by phototrophic indigenous organisms, in two contrasted soils treated by formulated maize herbicide mixtures.
PubMed: Solar photo-Fenton using peroxymonosulfate for organic micropollutants removal from domestic wastewater: comparison with heterogeneous TiO₂ photocatalysis.
PubMed: Photosynthetic responses and accumulation of mesotrione in two freshwater algae.
PubMed: Soil sorption and leaching of active ingredients of Lumax® under mineral or organic fertilization.
PubMed: Effect of soil properties on pure and formulated mesotrione adsorption onto vertisol (Limagne plane, Puy-de-Dôme, France).
PubMed: Mechanisms of tolerance and high degradation capacity of the herbicide mesotrione by Escherichia coli strain DH5-α.
PubMed: Novel bacterial bioassay for a high-throughput screening of 4-hydroxyphenylpyruvate dioxygenase inhibitors.
PubMed: Optimization of the polar organic chemical integrative sampler for the sampling of acidic and polar herbicides.
PubMed: Vitamin E levels in soybean (Glycine max (L.) Merr.) expressing a p-hydroxyphenylpyruvate gene from oat (Avena sativa L.).
PubMed: [Preparation and application of solid phase extraction packing of zirconia microsphere coated with sulfonated crosslinked polystyrene].
PubMed: Extraction procedures for the study of phytotoxicity and degradation processes of selected triketones in a water ecosystem.
PubMed: Toxicity assessment of the maize herbicides S-metolachlor, benoxacor, mesotrione and nicosulfuron, and their corresponding commercial formulations, alone and in mixtures, using the Microtox(®) test.
PubMed: The discovery of 3-(1-aminoethylidene)quinoline-2, 4(1H,3H)-dione derivatives as novel PSII electron transport inhibitors.
PubMed: Degradation of triketone herbicides, mesotrione and sulcotrione, using advanced oxidation processes.
PubMed: Distinct detoxification mechanisms confer resistance to mesotrione and atrazine in a population of waterhemp.
PubMed: Factors affecting the design of slow release formulations of herbicides based on clay-surfactant systems. A methodological approach.
PubMed: A review of the mode of toxicity and relevance to humans of the triketone herbicide 2-(4-methylsulfonyl-2-nitrobenzoyl)-1,3-cyclohexanedione.
PubMed: In planta mechanism of action of leptospermone: impact of its physico-chemical properties on uptake, translocation, and metabolism.
PubMed: The impact of mesotrione on several microbiological activity of chernozem soil.
PubMed: Dissipation and dynamics of mesotrione in maize and soil under field ecosystem.
PubMed: Electrochemical determination of mesotrione at organoclay modified glassy carbon electrodes.
PubMed: Dose-dependent effects of the herbicide mesotrione on soil cyanobacterial communities.
PubMed: Synthesis and herbicidal potential of substituted aurones.
PubMed: Effect of vegetative filter strips on herbicide runoff under various types of rainfall.
PubMed: Dissipation and residues of the herbicide mesotrione in maize and soil in open field.
PubMed: Comparative effects of the herbicides chlortoluron and mesotrione on freshwater microalgae.
PubMed: Isolation of mesotrione-degrading bacteria from aquatic environments in Brazil.
PubMed: Role of soil sorption and microbial degradation on dissipation of mesotrione in plant-available soil water.
PubMed: Sensitivity of locally naturalized Panicum species to HPPD- and ALS-inhibiting herbicides in maize.
PubMed: Degradation and mineralization of sulcotrione and mesotrione in aqueous medium by the electro-Fenton process: a kinetic study.
PubMed: Atmospheric aqueous-phase photoreactivity: correlation between the hydroxyl radical photoformation and pesticide degradation rate in atmospherically relevant waters.
PubMed: New procedures for simultaneous determination of mesotrione and atrazine in water and soil. Comparison of the degradation processes of mesotrione and atrazine.
PubMed: Kinetic and mechanistic investigations of mesotrione degradation in aqueous medium by Fenton process.
PubMed: Comparison of plasma and dry blood spots as samples for the determination of nitisinone (NTBC) by high-performance liquid chromatography-tandem mass spectrometry. Study of the stability of the samples at different temperatures.
PubMed: Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
PubMed: Sensitivity of Echinochloa muricata and Echinochloa crus-galli to HPPD- and ALS-inhibiting herbicides in corn.
PubMed: Monitoring tyrosinaemia type I: Blood spot test for nitisinone (NTBC).
PubMed: Biodegradation pathway of mesotrione: complementarities of NMR, LC-NMR and LC-MS for qualitative and quantitative metabolic profiling.
PubMed: Effect of a spreading adjuvant on mesotrione photolysis on wax films.
PubMed: The effect of mixing two herbicides mesotrione and nicosulfuron on their photochemical reactivity on cuticular wax film.
PubMed: Increase in nutritionally important sweet corn kernel carotenoids following Mesotrione and atrazine applications.
PubMed: Lemna minor L. as a model organism for ecotoxicological studies performing 1H NMR fingerprinting.
PubMed: 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.
PubMed: Mesotrione control and pigment concentration of large crabgrass (Digitaria sanguinalis) under varying environmental conditions.
PubMed: Isolation and characterization of mesotrione-degrading Bacillus sp. from soil.
PubMed: Effects of mesotrione on perennial ryegrass (Lolium perenne L.) carotenoid concentrations under varying environmental conditions.
PubMed: Ultra-pressure liquid chromatography-electrospray tandem mass spectrometry for multiresidue determination of pesticides in water.
PubMed: Interactions between population density of the Colorado potato beetle, Leptinotarsa decemlineata, and herbicide rate for suppression of solanaceous weeds.
PubMed: Toxicity assessment of the herbicides sulcotrione and mesotrione toward two reference environmental microorganisms: Tetrahymena pyriformis and Vibrio fischeri.
PubMed: The economics of atrazine.
PubMed: Behaviour of sulcotrione and mesotrione in two soils.
PubMed: 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.
PubMed: Photodegradation of sulcotrione in various aquatic environments and toxicity of its photoproducts for some marine micro-organisms.
PubMed: Biotransformation of the triketone herbicide mesotrione by a Bacillus strain. Metabolite profiling using liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry.
PubMed: First isolation and characterization of a bacterial strain that biotransforms the herbicide mesotrione.
PubMed: Simulated solar light irradiation of mesotrione in natural waters.
PubMed: Metabonomic strategy for the investigation of the mode of action of the phytotoxin (5S,8R,13S,16R)-(-)-pyrenophorol using 1H nuclear magnetic resonance fingerprinting.
PubMed: Determination of agrochemical compounds in soya plants by imaging matrix-assisted laser desorption/ionisation mass spectrometry.
PubMed: Soil activity and persistence of sulcotrione and mesotrione.
PubMed: Photosynthetic and growth responses of zea mays L and four weed species following post-emergence treatments with mesotrione and atrazinet.
PubMed: 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.
PubMed: Solid-phase fluoroimmunoassay for the determination of mesotrione--a novel triketone herbicide--in water with direct measurement of the fluorescence onto the solid support.
PubMed: Soil persistence of 4-HPPD-inhibitors in different soil types.
PubMed: Simultaneous determination of pesticides using a four-band disposable optical capillary immunosensor.
PubMed: 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.
PubMed: Activity of mesotrione on resistant weeds in maize.
PubMed: Determination of mesotrione residues and metabolites in crops, soil, and water by liquid chromatography with fluorescence detection.
PubMed: Adsorption and degradation of the weak acid mesotrione in soil and environmental fate implications.
PubMed: Metabolism of 2-(4-methylsulphonyl-2-nitrobenzoyl)-1,3-cyclohexanedione (mesotrione) in rat and mouse.
PubMed: 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.
PubMed: Mesotrione: a new selective herbicide for use in maize.
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