Brodifacoum

Basic Info

Common NameBrodifacoum(F05935)
2D Structure
FRCD IDF05935
CAS Number56073-10-0
PubChem CID54680676
FormulaC31H23BrO3
IUPAC Name

3-[3-[4-(4-bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-4-hydroxychromen-2-one

InChI Key

VEUZZDOCACZPRY-UHFFFAOYSA-N

InChI

InChI=1S/C31H23BrO3/c32-24-15-13-20(14-16-24)19-9-11-21(12-10-19)23-17-22-5-1-2-6-25(22)27(18-23)29-30(33)26-7-3-4-8-28(26)35-31(29)34/h1-16,23,27,33H,17-18H2

Canonical SMILES

C1C(CC2=CC=CC=C2C1C3=C(C4=CC=CC=C4OC3=O)O)C5=CC=C(C=C5)C6=CC=C(C=C6)Br

Isomeric SMILES

C1C(CC2=CC=CC=C2C1C3=C(C4=CC=CC=C4OC3=O)O)C5=CC=C(C=C5)C6=CC=C(C=C6)Br

Synonyms
        
            BRODIFACOUM
        
            56073-10-0
        
            Bromfenacoum
        
            Klerat
        
            Talon
        
            Volid
        
            Talon rodenticide
        
            Brodifakum
        
            Super warfarin
        
            WBA 8119
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassNaphthalenes
SubclassPhenylnaphthalenes
Intermediate Tree NodesNot available
Direct ParentPhenylnaphthalenes
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsPhenylnaphthalene - Brominated biphenyl - 4-hydroxycoumarin - Biphenyl - Hydroxycoumarin - Coumarin - Benzopyran - 1-benzopyran - Tetralin - Pyranone - Bromobenzene - Halobenzene - Aryl bromide - Aryl halide - Monocyclic benzene moiety - Pyran - Heteroaromatic compound - Vinylogous acid - Lactone - Organoheterocyclic compound - Oxacycle - Organobromide - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Organohalogen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenylnaphthalenes. These are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.

Properties

Property NameProperty Value
Molecular Weight523.426
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity791
Monoisotopic Mass522.083
Exact Mass522.083
XLogP7.6
Formal Charge0
Heavy Atom Count35
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8986
Human Intestinal AbsorptionHIA+0.9936
Caco-2 PermeabilityCaco2+0.7258
P-glycoprotein SubstrateNon-substrate0.6242
P-glycoprotein InhibitorNon-inhibitor0.9004
Non-inhibitor0.7149
Renal Organic Cation TransporterNon-inhibitor0.8633
Distribution
Subcellular localizationMitochondria0.4860
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7931
CYP450 2D6 SubstrateNon-substrate0.8811
CYP450 3A4 SubstrateNon-substrate0.6891
CYP450 1A2 InhibitorNon-inhibitor0.7900
CYP450 2C9 InhibitorInhibitor0.8860
CYP450 2D6 InhibitorNon-inhibitor0.9147
CYP450 2C19 InhibitorNon-inhibitor0.6651
CYP450 3A4 InhibitorNon-inhibitor0.7238
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6954
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9519
Non-inhibitor0.9435
AMES ToxicityNon AMES toxic0.9363
CarcinogensNon-carcinogens0.9157
Fish ToxicityHigh FHMT0.9931
Tetrahymena Pyriformis ToxicityHigh TPT0.9789
Honey Bee ToxicityHigh HBT0.6991
BiodegradationNot ready biodegradable0.9847
Acute Oral ToxicityI0.8401
Carcinogenicity (Three-class)Non-required0.4535
Model Value Unit
Absorption
Aqueous solubility-4.3338LogS
Caco-2 Permeability1.2695LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity6.4836LD50, mol/kg
Fish Toxicity0.3469pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.1203pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
HopJapan0.001ppm
HoneyJapan0.001ppm
Other Aquatic AnimalJapan0.001ppm
CrustaceansJapan0.001ppm
Shelled MolluscasJapan0.001ppm
Other FishJapan0.001ppm
PerciformesJapan0.001ppm
AnguilliformesJapan0.001ppm
SalmoniformesJapan0.001ppm
Other Poultry,EggsJapan0.001ppm
Chicken,EggsJapan0.001ppm
Other Poultry Animals,Edible OffalJapan0.001ppm
Chicken,Edible OffalJapan0.001ppm
Other Poultry Animals,KidneyJapan0.001ppm
Chicken,KidneyJapan0.001ppm
Other Poultry Animals,LiverJapan0.001ppm
Chicken,LiverJapan0.001ppm
Other Poultry Animals,FatJapan0.001ppm
Chicken,FatJapan0.001ppm
Other Poultry Animals,MuscleJapan0.001ppm

References

TitleJournalDatePubmed ID
Accumulation of anticoagulant rodenticides (chlorophacinone, bromadiolone andbrodifacoum) in a non-target invertebrate, the slug, Deroceras reticulatum.Sci Total Environ2018 Jan 128822925
Pesticide incidence in poisoned baits: A 10-year report.Sci Total Environ2017 Dec 128564626
Development and Validation of Quantitative Ultraperformance LiquidChromatography-Tandem Mass Spectrometry Assay for Anticoagulant Rodenticides inLiver.J Agric Food Chem2017 Aug 928699743
Simultaneous determination of seven anticoagulant rodenticides in agriculturalproducts by gel permeation chromatography and liquid chromatography-tandem massspectrometry.J Environ Sci Health B2016 Nov27428755
Suspected poisoning of domestic animals by pesticides.Sci Total Environ2016 Jan 126367188
Relation between Intensity of Biocide Practice and Residues of AnticoagulantRodenticides in Red Foxes (Vulpes vulpes).PLoS One2015 Sep 2926418154
Residue profiles of brodifacoum in coastal marine species following an islandrodent eradication.Ecotoxicol Environ Saf2015 Mar25437099
Interspecific and geographical differences in anticoagulant rodenticide residues of predatory wildlife from the Mediterranean region of Spain.Sci Total Environ2015 Apr 125546464
Assessment of anticoagulant rodenticide exposure in six raptor species from the Canary Islands (Spain).Sci Total Environ2014 Jul 124742545
New validated multiresidue analysis of six 4-hydroxy-coumarin anticoagulantrodenticides in hen eggs.J Vet Diagn Invest2013 Nov24081927
Brodifacoum is effective against Norway rats (Rattus norvegicus) in atyrosine139cysteine focus of anticoagulant resistance in Westphalia, Germany.Pest Manag Sci2012 Dec23007948
[Determination of 4-hydroxycoumarin rodenticides in animal products, fisheryproducts, and honey by liquid chromatography-tandem mass spectrometry].Shokuhin Eiseigaku Zasshi201121873815
Anticoagulant rodenticides in three owl species from Western Canada, 1988-2003.Arch Environ Contam Toxicol2010 Feb19826750
Multiresidue analysis of seven anticoagulant rodenticides by high-performanceliquid chromatography/electrospray/mass spectrometry.J Agric Food Chem2007 Feb 717263443
Field evaluation of capsaicin as a rodent aversion agent for poultry feed.Pest Manag Sci2003 Sep12974352
Shortfalls using second-generation anticoagulant rodenticides.J Zoo Wildl Med2002 Mar12216801
Palatability of bird repellents to Rattus norvegicus.Pest Manag Sci2001 Jul11464793
[Study of rat control by using bait box].Gaoxiong Yi Xue Ke Xue Za Zhi1990 Jul2402026
Rodenticides in British barn owls.Environ Pollut199015092196
Laboratory tests of seven rodenticides for the control of Meriones shawi.J Hyg (Lond)1983 Oct6605985