MESOTRIONE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11455642 | http://www.agribusinessglobal.com/uncategorized/product-profile-mesotrione/

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

Targets

Primary Target	Pharmacology	Condition	Potency
4-hydroxyphenylpyruvate dioxygenase 2 Target ID: CHEMBL2242740 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25185782 \| https://www.ncbi.nlm.nih.gov/pubmed/11455642	Inhibitor 8297		0.013 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	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.	2001	12425093
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 Aug	11488774
Mesotrione: a new selective herbicide for use in maize.	2001 Feb	11455642
Metabolism of 2-(4-methylsulphonyl-2-nitrobenzoyl)-1,3-cyclohexanedione (mesotrione) in rat and mouse.	2001 Oct	11695852
Soil persistence of 4-HPPD-inhibitors in different soil types.	2002	12696405
Simultaneous determination of pesticides using a four-band disposable optical capillary immunosensor.	2002 Dec 1	12498203
Determination of mesotrione residues and metabolites in crops, soil, and water by liquid chromatography with fluorescence detection.	2002 Jul 3	12083860
Adsorption and degradation of the weak acid mesotrione in soil and environmental fate implications.	2002 Mar-Apr	11931453
Activity of mesotrione on resistant weeds in maize.	2002 Sep	12233193
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 Apr	12741648
Soil activity and persistence of sulcotrione and mesotrione.	2004	15759393
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	14989481
Photosynthetic and growth responses of zea mays L and four weed species following post-emergence treatments with mesotrione and atrazinet.	2004 Nov	15532681
Biotransformation of the triketone herbicide mesotrione by a Bacillus strain. Metabolite profiling using liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry.	2006	16878338
First isolation and characterization of a bacterial strain that biotransforms the herbicide mesotrione.	2006 Aug	16869909
Simulated solar light irradiation of mesotrione in natural waters.	2006 Jun 15	16830551
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	16506820
Photodegradation of sulcotrione in various aquatic environments and toxicity of its photoproducts for some marine micro-organisms.	2007 Apr	17303209
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	17439817
The economics of atrazine.	2007 Oct-Dec	18085057
Behaviour of sulcotrione and mesotrione in two soils.	2008 Jan	17912682
Toxicity assessment of the herbicides sulcotrione and mesotrione toward two reference environmental microorganisms: Tetrahymena pyriformis and Vibrio fischeri.	2008 Nov	18322725
Effects of mesotrione on perennial ryegrass (Lolium perenne L.) carotenoid concentrations under varying environmental conditions.	2008 Oct 8	18788815
Isolation and characterization of mesotrione-degrading Bacillus sp. from soil.	2009 Apr	19121884
Lemna minor L. as a model organism for ecotoxicological studies performing 1H NMR fingerprinting.	2009 Aug	19443011
The watershed as a conceptual framework for the study of environmental and human health.	2009 Feb 18	20508751
Increase in nutritionally important sweet corn kernel carotenoids following Mesotrione and atrazine applications.	2009 Jul 22	19537793
Mesotrione control and pigment concentration of large crabgrass (Digitaria sanguinalis) under varying environmental conditions.	2009 Jun	19235182
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 May 15	19345648
Effect of a spreading adjuvant on mesotrione photolysis on wax films.	2009 Oct 28	20560626
Optoelectronic capillary sensors in microfluidic and point-of-care instrumentation.	2010	22319325
The effect of mixing two herbicides mesotrione and nicosulfuron on their photochemical reactivity on cuticular wax film.	2010 Apr	20153876
Methyl 4-methyl-sulfonyl-2-nitro-benzoate.	2010 Jun 16	21587895
Biodegradation pathway of mesotrione: complementarities of NMR, LC-NMR and LC-MS for qualitative and quantitative metabolic profiling.	2010 Sep	20692682

Patents

Sample Use Guides

In Vivo Use Guide

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

Mesotrione inhibited recombinant AtHPPD with IC50 value of 0.252 uM.

Name

Type

Language

MESOTRIONE

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