Tribenuron-methyl (CHEM002898)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:55 UTC
Update Date2016-11-09 01:08:59 UTC
Accession NumberCHEM002898
Identification
Common NameTribenuron-methyl
ClassSmall Molecule
DescriptionTribenuron-methyl is the methyl ester of the sulfonylurea herbicide tribenuron and also the form in which tribenuron is used in pesticides. It is used in the cultivation of cereals to combat broadleaf weeds. Similar to other sulfonylureas, the site of action of Tribenuron-methyl is acetolactate synthase (ALS), an enzyme involved in branched-chain amino acid biosynthesis. Sulfonylurea herbicides were discovered by DuPont in 1975 and marketed for the first time in 1982.
Contaminant Sources
  • Clean Air Act Chemicals
  • 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
Methyl 2-[({[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)(methyl)amino]carbonyl}amino)sulfonyl]benzoateChEBI
METHYL 2-[4-methoxy-6-methyl-1,3,5-trazin-2-yl(methyl)carbamoylsulfamoyl]benzoATEChEBI
Sulfmethmeton-methylChEBI
Tribenuron methyl esterChEBI
Tribenuron-methylChEBI
Methyl 2-[({[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)(methyl)amino]carbonyl}amino)sulfonyl]benzoic acidGenerator
Methyl 2-[({[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)(methyl)amino]carbonyl}amino)sulphonyl]benzoateGenerator
Methyl 2-[({[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)(methyl)amino]carbonyl}amino)sulphonyl]benzoic acidGenerator
METHYL 2-[4-methoxy-6-methyl-1,3,5-trazin-2-yl(methyl)carbamoylsulfamoyl]benzoic acidGenerator
METHYL 2-[4-methoxy-6-methyl-1,3,5-trazin-2-yl(methyl)carbamoylsulphamoyl]benzoateGenerator
METHYL 2-[4-methoxy-6-methyl-1,3,5-trazin-2-yl(methyl)carbamoylsulphamoyl]benzoic acidGenerator
Sulphmethmeton-methylGenerator
Metsulfuron-methylMeSH
AllyMeSH
Metsulfuron methylMeSH
Triazine-2-14C metsulfuron-methylMeSH
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
Chemical FormulaC15H17N5O6S
Average Molecular Mass395.390 g/mol
Monoisotopic Mass395.090 g/mol
CAS Registry Number101200-48-0
IUPAC Namemethyl 2-({[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)(methyl)carbamoyl]amino}sulfonyl)benzoate
Traditional Nametribenuron methyl
SMILESCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1
InChI IdentifierInChI=1S/C15H17N5O6S/c1-9-16-13(18-14(17-9)26-4)20(2)15(22)19-27(23,24)11-8-6-5-7-10(11)12(21)25-3/h5-8H,1-4H3,(H,19,22)
InChI KeyVLCQZHSMCYCDJL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as s-triazinyl-2-sulfonylureas. These are aromatic heterocyclic compounds containing a s-triazine ring which is substituted with a urea at the ring 2-position.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassSulfonylureas
Direct ParentS-triazinyl-2-sulfonylureas
Alternative Parents
Substituents
  • S-triazinyl-2-sulfonylurea
  • Benzenesulfonamide
  • Benzoate ester
  • Benzenesulfonyl group
  • Benzoic acid or derivatives
  • 2-methoxy-1,3,5-triazine
  • Alkoxy-s-triazine
  • Benzoyl
  • Alkyl aryl ether
  • Amino-1,3,5-triazine
  • N-aliphatic s-triazine
  • Monocyclic benzene moiety
  • 1,3,5-triazine
  • Benzenoid
  • Triazine
  • Heteroaromatic compound
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Methyl ester
  • Aminosulfonyl compound
  • Carbonic acid derivative
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Organooxygen compound
  • Carbonyl group
  • Organosulfur compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
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 Solubility0.024 g/LALOGPS
logP1.07ALOGPS
logP1.95ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.41ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area140.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity95.5 m³·mol⁻¹ChemAxon
Polarizability37.35 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, Positivesplash10-052b-0809000000-452116ac9f2224c106d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-e73b04e328b73631e435Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-4900000000-ef86602e5b4c952d4192Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0329000000-41f74f0a47690ee1a8f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052o-7669000000-4692a9b942bf32d7a1d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-a52309b3bc76fd73914cSpectrum
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 IDDB03656
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 ID9678
PubChem Compound ID153909
Kegg Compound IDC10962
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20048324
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21277578
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21637929
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21983197
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22217454