Bensulfuron-methyl (CHEM003438)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (8)XML
Record Information
Version1.0
Creation Date2014-08-29 06:51:37 UTC
Update Date2016-11-09 01:09:08 UTC
Accession NumberCHEM003438
Identification
Common NameBensulfuron-methyl
ClassSmall Molecule
DescriptionBensulfuron-methyl is a selective pre-emergence and post-emergence herbicide that inhibits the formation of acetolactate synthase (ALS inhibitor). Bensulfuron methyl is selective acting, through foliar and root uptake, by inhibiting biosynthesis of the essential amino acids valine and isoleucine. It stops cell division by inhibition of the acetolactate synthase enzyme. It could decrease the chlorophyll content and inhibit the growth of plant.
Contaminant Sources
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Herbicide
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Bensulfuron methylChEBI
Bensulfuron methyl esterChEBI
Methyl 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoateChEBI
Methyl alpha-((4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl)-O-toluateChEBI
Methyl alpha-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-O-toluateChEBI
Methyl bensulfuronChEBI
Bensulphuron methylGenerator
Bensulphuron methyl esterGenerator
Methyl 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoic acidGenerator
Methyl 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]methyl]benzoateGenerator
Methyl 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]methyl]benzoic acidGenerator
Methyl a-((4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl)-O-toluateGenerator
Methyl a-((4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl)-O-toluic acidGenerator
Methyl a-((4,6-dimethoxypyrimidin-2-yl)ureidosulphonyl)-O-toluateGenerator
Methyl a-((4,6-dimethoxypyrimidin-2-yl)ureidosulphonyl)-O-toluic acidGenerator
Methyl alpha-((4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl)-O-toluic acidGenerator
Methyl alpha-((4,6-dimethoxypyrimidin-2-yl)ureidosulphonyl)-O-toluateGenerator
Methyl alpha-((4,6-dimethoxypyrimidin-2-yl)ureidosulphonyl)-O-toluic acidGenerator
Methyl α-((4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl)-O-toluateGenerator
Methyl α-((4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl)-O-toluic acidGenerator
Methyl α-((4,6-dimethoxypyrimidin-2-yl)ureidosulphonyl)-O-toluateGenerator
Methyl α-((4,6-dimethoxypyrimidin-2-yl)ureidosulphonyl)-O-toluic acidGenerator
Methyl a-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-O-toluateGenerator
Methyl a-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-O-toluic acidGenerator
Methyl a-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulphamoyl]-O-toluateGenerator
Methyl a-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulphamoyl]-O-toluic acidGenerator
Methyl alpha-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-O-toluic acidGenerator
Methyl alpha-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulphamoyl]-O-toluateGenerator
Methyl alpha-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulphamoyl]-O-toluic acidGenerator
Methyl α-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-O-toluateGenerator
Methyl α-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-O-toluic acidGenerator
Methyl α-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulphamoyl]-O-toluateGenerator
Methyl α-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulphamoyl]-O-toluic acidGenerator
Methyl bensulphuronGenerator
Bensulphuron-methylGenerator
LondaxMeSH
2-((((((4,6-Dimethoxy-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)methyl)benzoic acid methyl esterMeSH
Methyl bensulfuron, lithium saltMeSH
Chemical FormulaC16H18N4O7S
Average Molecular Mass410.402 g/mol
Monoisotopic Mass410.090 g/mol
CAS Registry Number83055-99-6
IUPAC Namemethyl 2-[({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]amino}sulfonyl)methyl]benzoate
Traditional Namebensulfuron-methyl (PH7)
SMILESCOC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1
InChI IdentifierInChI=1S/C16H18N4O7S/c1-25-12-8-13(26-2)18-15(17-12)19-16(22)20-28(23,24)9-10-6-4-5-7-11(10)14(21)27-3/h4-8H,9H2,1-3H3,(H2,17,18,19,20,22)
InChI KeyXMQFTWRPUQYINF-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
  • Benzoate ester
  • Benzoyl
  • Alkyl aryl ether
  • Sulfonylurea
  • Pyrimidine
  • Heteroaromatic compound
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Methyl ester
  • Aminosulfonyl compound
  • Carboxylic acid ester
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • 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
ApplicationsNot Available
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 Solubility0.029 g/LALOGPS
logP1.49ALOGPS
logP1.68ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.29ChemAxon
pKa (Strongest Basic)1.67ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area145.81 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity99.69 m³·mol⁻¹ChemAxon
Polarizability39.11 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066s-2910000000-5bfa26dcc2be77e96ad6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0384900000-c4ae14d72d78683f08d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0980000000-f681369b0e6f777db5c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0831-1900000000-7760c6cebf0b482946eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pdi-0944800000-ec3bf1bbd00951dc35beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9682100000-a065fedbbbdd0b1d513eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9421000000-4fe7da2e8758dbd33ce5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06si-0942500000-1d6db5264536ef46ef8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-0967100000-74a7d9398387beb05848Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-2900000000-19a42029232df76afe94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1430900000-6e9b452e744a0e6a5decSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-7074650e43f3b662b0fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-7900000000-4d8294f6adc905a8cfa8Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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
DrugBank IDNot Available
HMDB IDHMDB0248961
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 ID49630
ChEBI ID3017
PubChem Compound ID54960
Kegg Compound IDC10937
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24406793
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25463855
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25797565
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26021849
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26453234