Basic Info

Common NameMetobromuron(F05843)
2D Structure
FRCD IDF05843
CAS Number3060-89-7
PubChem CID18290
FormulaC9H11BrN2O2
IUPAC Name

3-(4-bromophenyl)-1-methoxy-1-methylurea

InChI Key

WLFDQEVORAMCIM-UHFFFAOYSA-N

InChI

InChI=1S/C9H11BrN2O2/c1-12(14-2)9(13)11-8-5-3-7(10)4-6-8/h3-6H,1-2H3,(H,11,13)

Canonical SMILES

CN(C(=O)NC1=CC=C(C=C1)Br)OC

Isomeric SMILES

CN(C(=O)NC1=CC=C(C=C1)Br)OC

Synonyms
        
            METOBROMURON
        
            3060-89-7
        
            Metbromuron
        
            Patoran
        
            Metobromurone
        
            Monobromuron
        
            Pattonex
        
            3-(4-Bromophenyl)-1-methoxy-1-methylurea
        
            Caswell No. 579A
        
            CIBA-3126
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassN-phenylureas
Intermediate Tree NodesNot available
Direct ParentN-phenylureas
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsN-phenylurea - Bromobenzene - Halobenzene - Aryl bromide - Aryl halide - Carbonic acid derivative - Organic nitrogen compound - Organonitrogen compound - Organobromide - Organohalogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as n-phenylureas. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.

Properties

Property NameProperty Value
Molecular Weight259.103
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Complexity193
Monoisotopic Mass258
Exact Mass258
XLogP2.4
Formal Charge0
Heavy Atom Count14
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+0.9684
Human Intestinal AbsorptionHIA+0.9974
Caco-2 PermeabilityCaco2+0.5799
P-glycoprotein SubstrateNon-substrate0.8431
P-glycoprotein InhibitorNon-inhibitor0.9021
Non-inhibitor0.8634
Renal Organic Cation TransporterNon-inhibitor0.9394
Distribution
Subcellular localizationMitochondria0.6956
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7660
CYP450 2D6 SubstrateNon-substrate0.8238
CYP450 3A4 SubstrateNon-substrate0.5216
CYP450 1A2 InhibitorInhibitor0.6768
CYP450 2C9 InhibitorNon-inhibitor0.5908
CYP450 2D6 InhibitorNon-inhibitor0.8568
CYP450 2C19 InhibitorInhibitor0.5671
CYP450 3A4 InhibitorNon-inhibitor0.8788
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6519
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9633
Non-inhibitor0.9006
AMES ToxicityNon AMES toxic0.8647
CarcinogensNon-carcinogens0.6111
Fish ToxicityHigh FHMT0.7888
Tetrahymena Pyriformis ToxicityHigh TPT0.9965
Honey Bee ToxicityLow HBT0.8049
BiodegradationNot ready biodegradable0.9922
Acute Oral ToxicityIII0.7802
Carcinogenicity (Three-class)Non-required0.4418

Model Value Unit
Absorption
Aqueous solubility-2.9099LogS
Caco-2 Permeability1.8532LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0807LD50, mol/kg
Fish Toxicity1.3488pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8469pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
BeansKorea0.2ppm

References

TitleJournalDatePubmed ID
Assessment of the leaching potential of 12 substituted phenylurea herbicides intwo agricultural soils under laboratory conditions.J Agric Food Chem2012 May 3022578198
Application of solid-phase microextraction for determining phenylurea herbicides and their homologous anilines from vegetables.J Chromatogr A2004 Jul 915296383
Multiresidue HPLC methods for phenyl urea herbicides in water.J Agric Food Chem2000 Sep10995323
Determination of phenylurea herbicide residues in vegetables by liquidchromatography after gel permeation chromatography and Florisil cartridgecleanup.J AOAC Int1998 Sep-Oct9772748
Determination of linuron in potatoes using capillary column gaschromatography/mass spectrometry.J Assoc Off Anal Chem1989 Nov-Dec2592319