Basic Info

Common NameMetsulfuron-Methyl(F05106)
2D Structure
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.

FRCD IDF05106
CAS Number74223-64-6
PubChem CID52999
FormulaC14H15N5O6S
IUPAC Name

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

InChI Key

RSMUVYRMZCOLBH-UHFFFAOYSA-N

InChI

InChI=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)

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            Granstar
        
            Gropper
        
            Escort (pesticide)
        
            METSULFURON-METHYL
        
            Metsulfuron methyl
        
            74223-64-6
        
            Escort
        
            ALLY
        
            Allie
        
            Brush-off
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzoic acids and derivatives
Intermediate Tree NodesNot available
Direct ParentBenzoic acid esters
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsBenzenesulfonamide - 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
DescriptionThis compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Properties

Property NameProperty Value
Molecular Weight381.363
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count6
Complexity609
Monoisotopic Mass381.074
Exact Mass381.074
XLogP1.5
Formal Charge0
Heavy Atom Count26
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-0.5142
Human Intestinal AbsorptionHIA+0.8804
Caco-2 PermeabilityCaco2-0.6159
P-glycoprotein SubstrateNon-substrate0.8006
P-glycoprotein InhibitorNon-inhibitor0.8218
Non-inhibitor0.9445
Renal Organic Cation TransporterNon-inhibitor0.9123
Distribution
Subcellular localizationMitochondria0.5893
Metabolism
CYP450 2C9 SubstrateNon-substrate0.5000
CYP450 2D6 SubstrateNon-substrate0.8810
CYP450 3A4 SubstrateNon-substrate0.7103
CYP450 1A2 InhibitorNon-inhibitor0.8685
CYP450 2C9 InhibitorNon-inhibitor0.6616
CYP450 2D6 InhibitorNon-inhibitor0.9233
CYP450 2C19 InhibitorNon-inhibitor0.8152
CYP450 3A4 InhibitorNon-inhibitor0.6991
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8009
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9834
Non-inhibitor0.8342
AMES ToxicityNon AMES toxic0.7652
CarcinogensNon-carcinogens0.8047
Fish ToxicityHigh FHMT0.8766
Tetrahymena Pyriformis ToxicityHigh TPT0.7089
Honey Bee ToxicityLow HBT0.8575
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.8199
Carcinogenicity (Three-class)Non-required0.5462

Model Value Unit
Absorption
Aqueous solubility-3.4245LogS
Caco-2 Permeability0.4787LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8508LD50, mol/kg
Fish Toxicity1.6825pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4715pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Muscle1013010European Union0.01*02/01/2015
Others (2)1015990European Union0.01*02/01/2015
Muscle1016010European Union0.01*02/01/2015
Edible offals (other than liver and kidney)1015050European Union0.01*02/01/2015
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.01*02/01/2015
Citrus fruits0110000European Union0.01*02/01/2015
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*02/01/2015
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*02/01/2015
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*02/01/2015
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*02/01/2015
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.01*02/01/2015
Others (2)0110990European Union0.01*02/01/2015
Muscle1015010European Union0.01*02/01/2015
Fat1015020European Union0.01*02/01/2015
Liver1015030European Union0.01*02/01/2015
Kidney1015040European Union0.01*02/01/2015
Fat1013020European Union0.01*02/01/2015
Liver1013030European Union0.01*02/01/2015
Kidney1013040European Union0.01*02/01/2015
Others (2)1013990European Union0.01*02/01/2015

References

TitleJournalDatePubmed ID
Effects of grazing different ergovaline concentrations on vasoactivity of bovine lateral saphenous vein.J Anim Sci2018 Jun 2929701794
Simple, cost-effective and sensitive liquid chromatography diode array detectormethod for simultaneous determination of eight sulfonylurea herbicides in soyamilk samples.J Chromatogr A2016 Nov 1828314393
Metsulfuron-methyl-based herbicidal ionic liquids.J Agric Food Chem2015 Apr 825734891
Currently used pesticides and their mixtures affect the function of sex hormonereceptors and aromatase enzyme activity.Toxicol Appl Pharmacol2013 Oct 1523871939
Joint ecotoxicology of cadmium and metsulfuron-methyl in wheat (Triticum aestivum).Environ Monit Assess2013 Apr22773146
The nutritive value of grasspea (Lathyrus sativus) and allied species, their toxicity to animals and the role of malnutrition in neurolathyrism.Food Chem Toxicol2011 Mar21112364
Trace determination of sulfonylurea herbicides in water and grape samples bycapillary zone electrophoresis using large volume sample stacking.Anal Bioanal Chem2010 Jul20496055
Trace level determination of selected sulfonylurea herbicides in wetland sedimentby liquid chromatography electrospray tandem mass spectrometry.J Environ Sci Health B2010 Jan20390926
Persistence of metsulfuron-methyl in paddy field and detection of its residues incrop produce.Bull Environ Contam Toxicol2009 Dec19609477
Preparation of molecularly imprinted solid phase extraction usingbensulfuron-methyl imprinted polymer and clean-up for the sulfonylurea-herbicidesin soybean.Anal Chim Acta2008 Apr 2818405688
Factors influencing degradation of pesticides in soil.J Agric Food Chem2007 May 3017488087
Effects of soil storage on the microbial community and degradation ofmetsulfuron-methyl.J Agric Food Chem2006 Jan 1116390191
Effect of different soil textures on leaching potential and degradation ofpesticides in biobeds.J Agric Food Chem2004 Sep 815373405
[Simultaneous determination of ten sulfonylurea herbicide residues in soybeans byhigh performance liquid chromatography].Se Pu2004 Nov15807119
A comparison of crop and non-crop plants as sensitive indicator species forregulatory testing.Pest Manag Sci2002 Dec12476989
Ion chromatographic analysis of selected free amino acids and cations toinvestigate the change of nitrogen metabolism by herbicide stress in soybean(glycine max).J Agric Food Chem2001 Jan11305252
Analysis of metsulfuron-methyl in soil by liquid chromatography/tandem massspectrometry. Application to a field dissipation study.J Agric Food Chem1999 Oct10552834