Bromopropylate

Basic Info

Common NameBromopropylate(F05960)
2D Structure
FRCD IDF05960
CAS Number18181-80-1
PubChem CID28936
FormulaC17H16Br2O3
IUPAC Name

propan-2-yl 2,2-bis(4-bromophenyl)-2-hydroxyacetate

InChI Key

FOANIXZHAMJWOI-UHFFFAOYSA-N

InChI

InChI=1S/C17H16Br2O3/c1-11(2)22-16(20)17(21,12-3-7-14(18)8-4-12)13-5-9-15(19)10-6-13/h3-11,21H,1-2H3

Canonical SMILES

CC(C)OC(=O)C(C1=CC=C(C=C1)Br)(C2=CC=C(C=C2)Br)O

Isomeric SMILES

CC(C)OC(=O)C(C1=CC=C(C=C1)Br)(C2=CC=C(C=C2)Br)O

Synonyms
        
            Folbex VA
        
            Bromopropylate
        
            ACAROL
        
            18181-80-1
        
            Phenisobromolate
        
            Neoron
        
            Isopropyl 4,4'-dibromobenzilate
        
            Isopropyl dibromobenzilate
        
            Ascarol 2E
        
            Geigy 19851
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassDiphenylmethanes
Intermediate Tree NodesNot available
Direct ParentDiphenylmethanes
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsDiphenylmethane - Bromobenzene - Halobenzene - Aryl halide - Aryl bromide - Tertiary alcohol - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Aromatic alcohol - Organooxygen compound - Organobromide - Organohalogen compound - Organic oxygen compound - Carbonyl group - Alcohol - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Properties

Property NameProperty Value
Molecular Weight428.12
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Complexity348
Monoisotopic Mass425.947
Exact Mass427.945
XLogP4.8
Formal Charge0
Heavy Atom Count22
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+0.9691
Human Intestinal AbsorptionHIA+0.9897
Caco-2 PermeabilityCaco2+0.7180
P-glycoprotein SubstrateNon-substrate0.5738
P-glycoprotein InhibitorNon-inhibitor0.7618
Non-inhibitor0.7183
Renal Organic Cation TransporterNon-inhibitor0.8798
Distribution
Subcellular localizationMitochondria0.8954
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8168
CYP450 2D6 SubstrateNon-substrate0.9327
CYP450 3A4 SubstrateNon-substrate0.5000
CYP450 1A2 InhibitorNon-inhibitor0.7303
CYP450 2C9 InhibitorInhibitor0.7135
CYP450 2D6 InhibitorNon-inhibitor0.8608
CYP450 2C19 InhibitorNon-inhibitor0.7799
CYP450 3A4 InhibitorNon-inhibitor0.8599
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7272
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9972
Non-inhibitor0.8379
AMES ToxicityNon AMES toxic0.9112
CarcinogensNon-carcinogens0.5804
Fish ToxicityHigh FHMT0.9544
Tetrahymena Pyriformis ToxicityHigh TPT0.9717
Honey Bee ToxicityHigh HBT0.7489
BiodegradationNot ready biodegradable0.9940
Acute Oral ToxicityIII0.8253
Carcinogenicity (Three-class)Non-required0.4910
Model Value Unit
Absorption
Aqueous solubility-4.8678LogS
Caco-2 Permeability1.2136LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9642LD50, mol/kg
Fish Toxicity0.5912pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.0966pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Citrus FruitsNew Zealand3mg/kg
CarrotsBritain0.05mg/kg
Other Small Fruit & Berries (Other Than Wild)Britain0.05mg/kg
Safflower SeedsJapan2ppm
Japanese Plum(Including Prune)Japan2ppm
MaizeBritain0.05mg/kg
Peanuts,DryJapan0.1ppm
Strawberries (Other Than Wild)Israel2mg/kg
BroccoliJapan0.5ppm
CauliflowerJapan0.5ppm
VegetableItaly1.00mg/kg
Other Cereals Do Not Include RiceBritain0.05mg/kg
Ware PotatoesBritain0.05mg/kg
Wild MushroomsBritain0.05mg/kg
ChervilBritain0.05mg/kg
Brussels SproutsBritain0.05mg/kg
Other Root And Tuber VegetablesBritain0.05mg/kg
ParsnipsBritain0.05mg/kg
Jerusalem ArtichokesBritain0.05mg/kg
HorseradishBritain0.05mg/kg

References

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Evaluation of immunoassays as an alternative for the rapid determination ofpesticides in wine and grape samples.J AOAC Int2010 Jan-Feb20334160
Competitive multi-immunosensing of pesticides based on the particle manipulation with negative dielectrophoresis.Biosens Bioelectron2010 Apr 1520129771
Compensation for matrix effects in gas chromatography-tandem mass spectrometryusing a single point standard addition.J Chromatogr A2009 Jun 519406413
Development of an enzyme-linked immunosorbent assay for determination of themiticide bromopropylate.J Agric Food Chem2009 Jan 2819113903
Determination of synthetic acaricides residues in beeswax by high-performanceliquid chromatography with photodiode array detector.Anal Chim Acta2007 Jan 217386431
Repeated dose 28-day oral toxicity study in Wistar rats with a mixture of fivepesticides often found as residues in food: alphacypermethrin, bromopropylate,carbendazim, chlorpyrifos and mancozeb.Food Chem Toxicol2004 Aug15207377
Determination of impurities in pesticides and their degradation products formedduring the wine-making process by solid-phase extraction and gas chromatographywith detection by electron ionization mass spectrometry. II. Bromopropylate,trichlorphon, parathion-methyl and tebuconazole.Rapid Commun Mass Spectrom200415481093
Rapid multi-residue method for the determination of azinphos methyl,bromopropylate, chlorpyrifos, dimethoate, parathion methyl and phosalone inapricots and peaches by using negative chemical ionization ion trap technology.J Chromatogr A2003 May 912830919
[Identification and determination of unknown chemicals in crops by dual-column GCsystem equipped with MS and ECD].Shokuhin Eiseigaku Zasshi2002 Jun12238149
Study of an accelerated solvent extraction procedure for the determination ofacaricide residues in honey by high-performance liquid chromatography-diode arraydetector.J Food Prot2002 Jan11808788
Determination of acaricides in honey by high-performance liquid chromatographywith photodiode array detection.J Chromatogr A2002 Apr 1912058901
Monitoring of pesticide residues in Egyptian fruits and vegetables during 1996.J AOAC Int2001 Mar-Apr11324620
Study of acaricide stability in honey. Characterization of amitraz degradationproducts in honey and beeswax.J Agric Food Chem2001 Dec11743771
Solid phase microextraction of pesticide residues from strawberries.Food Addit Contam1999 Mar10492703
Acaricide residues in honeys from Galicia (N.W. Spain).J Food Prot1997 Jan10465046
Comparison of octadecylsilica and graphitized carbon black as materials forsolid-phase extraction of fungicide and insecticide residues from fruit andvegetables.J Chromatogr A1997 Aug 229299730