Metsulfuron-methyl (CHEM002844)

Record Information
Version1.0
Creation Date2013-04-25 07:56:53 UTC
Update Date2026-08-19 05:46:44 UTC
Accession NumberCHEM002844
Identification
Common NameMetsulfuron-methyl
ClassSmall Molecule
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 residual activity in soils, allowing it to be used infrequently but requiring up to 22 months before planting certain crops (sunflowers, flax, corn, or safflower). It has very low toxicity to mammals, birds, fish, and insects, but is a moderate eye irritant.
Contaminant Sources
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Herbicide
  • Lachrymator
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Metsulfuron methyl esterChEBI
Metsulfuron methylKegg
Metsulphuron methyl esterGenerator
Metsulphuron methylGenerator
Metsulphuron-methylGenerator
Methyl 2-(((((4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)benzoateMeSH
Benzoic acid, 2-(((((4-methoxy-6-methyl-1,3,5-triazin-2- yl)methylamino)carbonyl)amino)sulfonyl)-, methyl esterMeSH
Tribenuron-methylMeSH
Tribenuron methylMeSH
Triazine-2-14C metsulfuron-methylMeSH
AllyMeSH
Chemical FormulaC14H15N5O6S
Average Molecular Mass381.364 g/mol
Monoisotopic Mass381.074 g/mol
CAS Registry Number74223-64-6
IUPAC Namemethyl 2-({[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]amino}sulfonyl)benzoate
Traditional Namemetsulfuron-methyl
SMILESCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1
InChI IdentifierInChI=1S/C14H15N5O6S/c1-8-15-12(18-14(16-8)25-3)17-13(21)19-26(22,23)10-7-5-4-6-9(10)11(20)24-2/h4-7H,1-3H3,(H2,15,16,17,18,19,21)
InChI KeyRSMUVYRMZCOLBH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Benzoate ester
  • Benzenesulfonyl group
  • 2-methoxy-1,3,5-triazine
  • Alkoxy-s-triazine
  • Benzoyl
  • Alkyl aryl ether
  • 1,3,5-triazine
  • Triazine
  • Heteroaromatic compound
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Methyl ester
  • Sulfonyl
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP1.06ALOGPS
logP2.11ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)0.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area149.47 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity92.38 m³·mol⁻¹ChemAxon
Polarizability36.27 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMetsulfuron-methyl
Chemspider IDNot Available
ChEBI ID39678
PubChem Compound ID52999
Kegg Compound IDC10946
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21036398
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23348034
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23972318