Tribenuron-Methyl

Basic Info

Common NameTribenuron-Methyl(F05149)
2D Structure
Description

Tribenuron-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.

FRCD IDF05149
CAS Number101200-48-0
PubChem CID153909
FormulaC15H17N5O6S
IUPAC Name

methyl 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-methylcarbamoyl]sulfamoyl]benzoate

InChI Key

VLCQZHSMCYCDJL-UHFFFAOYSA-N

InChI

InChI=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)

Canonical SMILES

CC1=NC(=NC(=N1)OC)N(C)C(=O)NS(=O)(=O)C2=CC=CC=C2C(=O)OC

Isomeric SMILES

CC1=NC(=NC(=N1)OC)N(C)C(=O)NS(=O)(=O)C2=CC=CC=C2C(=O)OC

Synonyms
        
            Tribenuron methyl ester
        
            TRIBENURON-METHYL
        
            Tribenuron methyl
        
            101200-48-0
        
            Express
        
            Sulfmethmeton-methyl
        
            Cameo
        
            Cameo (pesticide)
        
            Camer (pesticide)
        
            Express (pesticide)
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic nitrogen compounds
ClassOrganonitrogen compounds
SubclassSulfonylureas
Intermediate Tree NodesNot available
Direct ParentS-triazinyl-2-sulfonylureas
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsS-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
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight395.39
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count6
Complexity639
Monoisotopic Mass395.09
Exact Mass395.09
XLogP1.2
Formal Charge0
Heavy Atom Count27
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+0.6927
Human Intestinal AbsorptionHIA+0.9269
Caco-2 PermeabilityCaco2-0.6070
P-glycoprotein SubstrateNon-substrate0.8617
P-glycoprotein InhibitorNon-inhibitor0.7890
Non-inhibitor0.8658
Renal Organic Cation TransporterNon-inhibitor0.9051
Distribution
Subcellular localizationMitochondria0.4977
Metabolism
CYP450 2C9 SubstrateNon-substrate0.5511
CYP450 2D6 SubstrateNon-substrate0.8619
CYP450 3A4 SubstrateNon-substrate0.6712
CYP450 1A2 InhibitorNon-inhibitor0.8525
CYP450 2C9 InhibitorNon-inhibitor0.5859
CYP450 2D6 InhibitorNon-inhibitor0.9284
CYP450 2C19 InhibitorNon-inhibitor0.7251
CYP450 3A4 InhibitorNon-inhibitor0.5669
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7380
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9728
Non-inhibitor0.8069
AMES ToxicityNon AMES toxic0.7359
CarcinogensNon-carcinogens0.7528
Fish ToxicityHigh FHMT0.7412
Tetrahymena Pyriformis ToxicityHigh TPT0.6256
Honey Bee ToxicityLow HBT0.8607
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7886
Carcinogenicity (Three-class)Non-required0.5499
Model Value Unit
Absorption
Aqueous solubility-3.5108LogS
Caco-2 Permeability0.7816LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9294LD50, mol/kg
Fish Toxicity1.6231pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4854pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
SquashesBritain0.01mg/kg
Wild Berries & Wild FruitBritain0.01mg/kg
WheatAustralia0.01mg/kg
Other Cereals Do Not Include RiceBritain0.01mg/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 OilseedsBritain0.01mg/kg
Hemp SeedBritain0.01mg/kg

References

TitleJournalDatePubmed ID
Metabolic Resistance to Acetolactate Synthase Inhibiting HerbicideTribenuron-Methyl in Descurainia sophia L. Mediated by Cytochrome P450 Enzymes.J Agric Food Chem2018 May 229652484
Discovery of New 2-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)oxy]-6-(substitutedphenoxy)benzoic Acids as Flexible Inhibitors of Arabidopsis thalianaAcetohydroxyacid Synthase and Its P197L Mutant.J Agric Food Chem2017 Dec 2729186952
Unravelling the resistance mechanisms to 2,4-D (2,4-dichlorophenoxyacetic acid)in corn poppy (Papaver rhoeas).Pestic Biochem Physiol2016 Oct27742363
Synthesis and herbicidal activity of12-(aryloxyacyloxyimino)-1,15-pentadecanlactone derivatives.J Agric Food Chem2009 Jan 2819117417
Leaching of three sulfonylurea herbicides during sprinkler irrigation.J Environ Qual2009 Dec 3020048324
Preparation of molecularly imprinted solid phase extraction usingbensulfuron-methyl imprinted polymer and clean-up for the sulfonylurea-herbicidesin soybean.Anal Chim Acta2008 Apr 2818405688
Perinatal exposure to the fungicide prochloraz feminizes the male rat offspring.Toxicol Sci2005 Jun15788727
The combined antiandrogenic effects of five commonly used pesticides.Toxicol Appl Pharmacol2004 Nov 1515519604
Comparative efficacy of five herbicides on winter cereal weeds in semi-aridregion of Algeria.Meded Rijksuniv Gent Fak Landbouwkd Toegep Biol Wet200112425104
Coupling of size-exclusion chromatography to liquid chromatography/massspectrometry for determination of trace levels of thifensulfuron-methyl andtribenuron-methyl in cottonseed and cotton gin trash.J AOAC Int2000 May-Jun10868588