Basic Info

Common NamePrimisulfuron-Methyl(F05122)
2D Structure
Description

Primisulfuron-methyl is a urea herbicide that is used on crop and non- crop areas for the control of grass weeds and many kinds of broad-leaved weeds. The compound is a selective postemergence systemic herbicide that is rapidly absorbed by plants and transported throughout the plant roots and foliage. The herbicide works by blocking cell growth in the active growing regions of the plant. The herbicide also acts to inhibit photosynthesis

FRCD IDF05122
CAS Number86209-51-0
PubChem CID101525
FormulaC15H12F4N4O7S
IUPAC Name

methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate

InChI Key

ZTYVMAQSHCZXLF-UHFFFAOYSA-N

InChI

InChI=1S/C15H12F4N4O7S/c1-28-11(24)7-4-2-3-5-8(7)31(26,27)23-15(25)22-14-20-9(29-12(16)17)6-10(21-14)30-13(18)19/h2-6,12-13H,1H3,(H2,20,21,22,23,25)

Canonical SMILES

COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC2=NC(=CC(=N2)OC(F)F)OC(F)F

Isomeric SMILES

COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC2=NC(=CC(=N2)OC(F)F)OC(F)F

Synonyms
        
            Tell
        
            3TN6B6S8JP
        
            Primisulfuron-methyl
        
            Beacon
        
            86209-51-0
        
            Rifle
        
            UNII-3TN6B6S8JP
        
            Primisulfuron methyl
        
            HSDB 7062
        
            CGA 136872
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic nitrogen compounds
ClassOrganonitrogen compounds
SubclassSulfonylureas
Intermediate Tree NodesNot available
Direct ParentPyrimidinyl-2-sulfonylureas
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPyrimidinyl-2-sulfonylurea - Benzenesulfonamide - Benzoate ester - Benzoic acid or derivatives - Benzenesulfonyl group - Benzoyl - Monocyclic benzene moiety - Pyrimidine - Benzenoid - Methyl ester - Aminosulfonyl compound - Sulfonyl - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Heteroaromatic compound - Carboxylic acid ester - Carbonic acid derivative - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organoheterocyclic compound - Azacycle - Alkyl fluoride - Organohalogen compound - Organofluoride - Organooxygen compound - Carbonyl group - Organosulfur compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Alkyl halide - Aromatic heteromonocyclic compound
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight468.336
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count13
Rotatable Bond Count9
Complexity707
Monoisotopic Mass468.036
Exact Mass468.036
XLogP3.6
Formal Charge0
Heavy Atom Count31
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-0.5965
Human Intestinal AbsorptionHIA+0.9232
Caco-2 PermeabilityCaco2-0.5886
P-glycoprotein SubstrateNon-substrate0.8174
P-glycoprotein InhibitorNon-inhibitor0.8011
Non-inhibitor0.9746
Renal Organic Cation TransporterNon-inhibitor0.8967
Distribution
Subcellular localizationMitochondria0.6202
Metabolism
CYP450 2C9 SubstrateSubstrate0.5161
CYP450 2D6 SubstrateNon-substrate0.8641
CYP450 3A4 SubstrateNon-substrate0.6950
CYP450 1A2 InhibitorNon-inhibitor0.7774
CYP450 2C9 InhibitorNon-inhibitor0.6478
CYP450 2D6 InhibitorNon-inhibitor0.8781
CYP450 2C19 InhibitorNon-inhibitor0.7475
CYP450 3A4 InhibitorNon-inhibitor0.8887
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7613
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9940
Non-inhibitor0.8652
AMES ToxicityNon AMES toxic0.7824
CarcinogensNon-carcinogens0.8027
Fish ToxicityHigh FHMT0.9462
Tetrahymena Pyriformis ToxicityHigh TPT0.8050
Honey Bee ToxicityLow HBT0.8941
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIV0.6241
Carcinogenicity (Three-class)Non-required0.5989

Model Value Unit
Absorption
Aqueous solubility-3.7012LogS
Caco-2 Permeability0.4848LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9483LD50, mol/kg
Fish Toxicity1.6894pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5458pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Poultry Animals,Edible OffalJapan0.1ppm
Other Poultry,EggsJapan0.1ppm
Other Poultry Animals,KidneyJapan0.1ppm
Chicken,KidneyJapan0.1ppm
Other Poultry Animals,LiverJapan0.1ppm
Chicken,LiverJapan0.1ppm
Other Poultry Animals,FatJapan0.1ppm
Chicken,FatJapan0.1ppm
Other Poultry Animals,MuscleJapan0.1ppm
Chicken,MuscleJapan0.1ppm
MilkJapan0.02ppm
Other Terrestrial Mammals,Edible OffalJapan0.1ppm
Pig,Edible OffalJapan0.1ppm
Cattle,Edible OffalJapan0.1ppm
Other Terrestrial Mammals,KidneyJapan0.1ppm
Pig,KidneyJapan0.1ppm
Cattle,KidneyJapan0.1ppm
Other Terrestrial Mammals,LiverJapan0.1ppm
Pig,LiverJapan0.1ppm
Cattle,LiverJapan0.1ppm