Basic Info

Common NameMesosulfuron-Methyl(F05100)
2D Structure
Description

Metsulfuron-methyl is a residual sulfonylurea herbicide that kills broadleaf weeds and some annual grasses. It is a systemic compound with foliar and soil activity, that inhibits cell division in shoots and roots. It has very low toxicity to mammals, birds, fish, and insects, but is a moderate eye irritant.

FRCD IDF05100
CAS Number208465-21-8
PubChem CID11409499
FormulaC17H21N5O9S2
IUPAC Name

methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate

InChI Key

NIFKBBMCXCMCAO-UHFFFAOYSA-N

InChI

InChI=1S/C17H21N5O9S2/c1-29-13-8-14(30-2)20-16(19-13)21-17(24)22-33(27,28)12-7-10(9-18-32(4,25)26)5-6-11(12)15(23)31-3/h5-8,18H,9H2,1-4H3,(H2,19,20,21,22,24)

Canonical SMILES

COC1=CC(=NC(=N1)NC(=O)NS(=O)(=O)C2=C(C=CC(=C2)CNS(=O)(=O)C)C(=O)OC)OC

Isomeric SMILES

COC1=CC(=NC(=N1)NC(=O)NS(=O)(=O)C2=C(C=CC(=C2)CNS(=O)(=O)C)C(=O)OC)OC

Synonyms
        
            methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate
        
            Mesosulfuron-methyl
        
            208465-21-8
        
            Mesomaxx
        
            Mesosulfuron-methyl [ISO]
        
            UNII-22L00R79A6
        
            22L00R79A6
        
            Benzoic acid, 2-(4,6-dimethoxy-2-pyrimidinyl)aminocarbonylaminosulfonyl-4-(methylsulfonyl)amin
        
            Benzoic acid, 2-(((((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)-4-(((methylsulfonyl)amino)methyl)-, methyl ester
        
            SCHEMBL116828
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic nitrogen compounds
ClassOrganonitrogen compounds
SubclassSulfonylureas
Intermediate Tree NodesNot available
Direct ParentPyrimidinyl-2-sulfonylureas
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPyrimidinyl-2-sulfonylurea - Benzenesulfonamide - Benzoate ester - Benzenesulfonyl group - Benzoic acid or derivatives - Benzoyl - Alkyl aryl ether - Pyrimidine - Organic sulfonic acid amide - Organosulfonic acid amide - Benzenoid - Monocyclic benzene moiety - Sulfonyl - Organosulfonic acid or derivatives - Aminosulfonyl compound - Methyl ester - Organic sulfonic acid or derivatives - Heteroaromatic compound - Carbonic acid derivative - Carboxylic acid ester - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Ether - Monocarboxylic acid or derivatives - Carbonyl group - Organic oxygen compound - Organopnictogen compound - Organosulfur compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as pyrimidinyl-2-sulfonylureas. These are aromatic heterocyclic compounds containing a pyrimidine ring which is substituted with a sulfonylurea at the ring 2-position.

Properties

Property NameProperty Value
Molecular Weight503.501
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count12
Rotatable Bond Count10
Complexity876
Monoisotopic Mass503.078
Exact Mass503.078
XLogP0.6
Formal Charge0
Heavy Atom Count33
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.5621
Human Intestinal AbsorptionHIA+0.8318
Caco-2 PermeabilityCaco2-0.6677
P-glycoprotein SubstrateNon-substrate0.7010
P-glycoprotein InhibitorNon-inhibitor0.7965
Non-inhibitor0.8699
Renal Organic Cation TransporterNon-inhibitor0.8649
Distribution
Subcellular localizationMitochondria0.5961
Metabolism
CYP450 2C9 SubstrateSubstrate0.5122
CYP450 2D6 SubstrateNon-substrate0.8587
CYP450 3A4 SubstrateNon-substrate0.6404
CYP450 1A2 InhibitorNon-inhibitor0.7735
CYP450 2C9 InhibitorNon-inhibitor0.6007
CYP450 2D6 InhibitorNon-inhibitor0.8734
CYP450 2C19 InhibitorNon-inhibitor0.6804
CYP450 3A4 InhibitorNon-inhibitor0.6857
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7609
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9816
Non-inhibitor0.8342
AMES ToxicityNon AMES toxic0.6986
CarcinogensNon-carcinogens0.7546
Fish ToxicityHigh FHMT0.9441
Tetrahymena Pyriformis ToxicityHigh TPT0.6896
Honey Bee ToxicityLow HBT0.7945
BiodegradationNot ready biodegradable0.9964
Acute Oral ToxicityIII0.7438
Carcinogenicity (Three-class)Non-required0.5822

Model Value Unit
Absorption
Aqueous solubility-3.7007LogS
Caco-2 Permeability0.1408LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9424LD50, mol/kg
Fish Toxicity1.6291pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4332pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Cereals Do Not Include RiceBritain0.01mg/kg
Other Small Fruit & Berries (Other Than Wild)Britain0.01mg/kg
Other Terrestrial Mammals,Edible OffalJapan0.01ppm
PlumsBritain0.01mg/kg
RiceBritain0.01mg/kg
MilletBritain0.01mg/kg
BuckwheatBritain0.01mg/kg
MaizeBritain0.01mg/kg
TriticaleBritain0.01mg/kg
OatsBritain0.01mg/kg
SorghumBritain0.01mg/kg
BarleyBritain0.01mg/kg
RyeBritain0.01mg/kg
WheatBritain0.01mg/kg
HopBritain0.02mg/kg
TeaBritain0.02mg/kg
Ware PotatoesBritain0.01mg/kg
Early PotatoesBritain0.01mg/kg
Other OilseedsBritain0.02mg/kg
Hemp SeedBritain0.02mg/kg