Bensulfuron methyl (free acid; IN-R9419) (CHEM042700)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 10:06:31 UTC
Update Date2016-11-09 01:22:47 UTC
Accession NumberCHEM042700
Identification
Common NameBensulfuron methyl (free acid; IN-R9419)
ClassSmall Molecule
DescriptionAn N-sulfonylurea that is urea in which a hydrogen attached to one of the nitrogens has been replaced by an (o-carboxybenzyl)sulfonyl group, while a hydrogen attached to the other nitrogen has been replaced by a 4,6-dimethoxypyrimidin-2-yl group. An acetolactate synthase inhibitor, it is used (particularly as its methyl ester, bensulfuron-methyl) as a herbicide for the control of a variety of both annual and perennial weeds in crops, particularly wheat and rice.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-[[[[[(4,6-Dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoic acidChEBI
alpha-[(4,6-Dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-O-toluic acidChEBI
2-[[[[[(4,6-Dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoateGenerator
2-[[[[[(4,6-Dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]methyl]benzoateGenerator
2-[[[[[(4,6-Dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]methyl]benzoic acidGenerator
a-[(4,6-Dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-O-toluateGenerator
a-[(4,6-Dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-O-toluic acidGenerator
a-[(4,6-Dimethoxypyrimidin-2-ylcarbamoyl)sulphamoyl]-O-toluateGenerator
a-[(4,6-Dimethoxypyrimidin-2-ylcarbamoyl)sulphamoyl]-O-toluic acidGenerator
alpha-[(4,6-Dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-O-toluateGenerator
alpha-[(4,6-Dimethoxypyrimidin-2-ylcarbamoyl)sulphamoyl]-O-toluateGenerator
alpha-[(4,6-Dimethoxypyrimidin-2-ylcarbamoyl)sulphamoyl]-O-toluic acidGenerator
Α-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-O-toluateGenerator
Α-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-O-toluic acidGenerator
Α-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulphamoyl]-O-toluateGenerator
Α-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulphamoyl]-O-toluic acidGenerator
BensulphuronGenerator
Chemical FormulaC15H16N4O7S
Average Molecular Mass396.370 g/mol
Monoisotopic Mass396.074 g/mol
CAS Registry Number99283-01-9
IUPAC Name2-[({[(4,6-dimethoxypyrimidin-2-yl)-C-hydroxycarbonimidoyl]amino}sulfonyl)methyl]benzoic acid
Traditional Name2-({[(4,6-dimethoxypyrimidin-2-yl)-C-hydroxycarbonimidoyl]aminosulfonyl}methyl)benzoic acid
SMILESCOC1=CC(OC)=NC(N=C(O)NS(=O)(=O)CC2=CC=CC=C2C(O)=O)=N1
InChI IdentifierInChI=1S/C15H16N4O7S/c1-25-11-7-12(26-2)17-14(16-11)18-15(22)19-27(23,24)8-9-5-3-4-6-10(9)13(20)21/h3-7H,8H2,1-2H3,(H,20,21)(H2,16,17,18,19,22)
InChI KeyPPWBRCCBKOWDNB-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassSulfonylureas
Direct ParentPyrimidinyl-2-sulfonylureas
Alternative Parents
Substituents
  • Pyrimidinyl-2-sulfonylurea
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyrimidine
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Carbonic acid derivative
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organosulfur compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.099 g/LALOGPS
logP0.54ALOGPS
logP1.96ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)1.38ChemAxon
pKa (Strongest Basic)-0.41ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area160.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.68 m³·mol⁻¹ChemAxon
Polarizability36.43 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f92-0739000000-718b0aabc4fc899a742dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-a234e6ea4d2e69c0f1f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ukl-4900000000-df6cb47567a0956a2c4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0649000000-6edc58d9bfde61c4505fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08mi-8892000000-74e73da809186cb3ab38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08i0-9720000000-570662387c78f493732aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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 LinkNot Available
Chemspider IDNot Available
ChEBI ID132880
PubChem Compound ID107828
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24406793