Propanil

Basic Info

Common NamePropanil(F06073)
2D Structure
FRCD IDF06073
CAS Number709-98-8
PubChem CID4933
FormulaC9H9Cl2NO
IUPAC Name

N-(3,4-dichlorophenyl)propanamide

InChI Key

LFULEKSKNZEWOE-UHFFFAOYSA-N

InChI

InChI=1S/C9H9Cl2NO/c1-2-9(13)12-6-3-4-7(10)8(11)5-6/h3-5H,2H2,1H3,(H,12,13)

Canonical SMILES

CCC(=O)NC1=CC(=C(C=C1)Cl)Cl

Isomeric SMILES

CCC(=O)NC1=CC(=C(C=C1)Cl)Cl

Synonyms
        
            propanil
        
            Propanide
        
            709-98-8
        
            N-(3,4-Dichlorophenyl)propanamide
        
            Grascide
        
            Propanex
        
            Propanid
        
            Supernox
        
            Surcopur
        
            Dipram
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassAnilides
Intermediate Tree NodesNot available
Direct ParentAnilides
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsAnilide - 1,2-dichlorobenzene - N-arylamide - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Organochloride - Organohalogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Properties

Property NameProperty Value
Molecular Weight218.077
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Complexity187
Monoisotopic Mass217.006
Exact Mass217.006
XLogP3.1
Formal Charge0
Heavy Atom Count13
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+0.9951
Human Intestinal AbsorptionHIA+0.9956
Caco-2 PermeabilityCaco2+0.7989
P-glycoprotein SubstrateNon-substrate0.7799
P-glycoprotein InhibitorNon-inhibitor0.8533
Non-inhibitor0.9945
Renal Organic Cation TransporterNon-inhibitor0.9010
Distribution
Subcellular localizationMitochondria0.6862
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7607
CYP450 2D6 SubstrateNon-substrate0.7778
CYP450 3A4 SubstrateSubstrate0.5127
CYP450 1A2 InhibitorInhibitor0.9476
CYP450 2C9 InhibitorInhibitor0.6985
CYP450 2D6 InhibitorInhibitor0.6206
CYP450 2C19 InhibitorInhibitor0.8609
CYP450 3A4 InhibitorNon-inhibitor0.8280
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.7305
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9510
Non-inhibitor0.9138
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.5216
Fish ToxicityHigh FHMT0.7423
Tetrahymena Pyriformis ToxicityHigh TPT0.9890
Honey Bee ToxicityLow HBT0.8777
BiodegradationNot ready biodegradable0.9202
Acute Oral ToxicityII0.7187
Carcinogenicity (Three-class)Non-required0.7670
Model Value Unit
Absorption
Aqueous solubility-3.0628LogS
Caco-2 Permeability1.8252LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7427LD50, mol/kg
Fish Toxicity1.0595pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8659pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Poultry,EggsJapan0.08ppm
Chicken,EggsJapan0.08ppm
Other Poultry Animals,Edible OffalJapan2ppm
Chicken,Edible OffalJapan2ppm
Other Poultry Animals,KidneyJapan2ppm
Chicken,KidneyJapan2ppm
Other Poultry Animals,LiverJapan2ppm
Chicken,LiverJapan2ppm
Other Poultry Animals,FatJapan0.1ppm
Chicken,FatJapan0.1ppm
Other Poultry Animals,MuscleJapan0.1ppm
Chicken,MuscleJapan0.1ppm
MilkJapan0.03ppm
Other Terrestrial Mammals,Edible OffalJapan0.1ppm
Pig,Edible OffalJapan0.1ppm
Cattle,Edible OffalJapan0.1ppm
Other Terrestrial Mammals,KidneyJapan0.1ppm
Pig,KidneyJapan0.1ppm
Pig,LiverJapan0.1ppm
Cattle,LiverJapan0.1ppm

References

TitleJournalDatePubmed ID
Aquatic risk assessment of priority and other river basin specific pesticides in surface waters of Mediterranean river basins.Chemosphere2015 Sep26002046
Estimation and Validation of Propanil Residues in Rice and Soil Samples by GasLiquid Chromatography with Electron Capture Detector.Bull Environ Contam Toxicol2015 Sep26232197
Community air monitoring for pesticides-part 2: multiresidue determination ofpesticides in air by gas chromatography, gas chromatography-mass spectrometry,and liquid chromatography-mass spectrometry.Environ Monit Assess2014 Mar24370860
Pesticides in Mississippi air and rain: a comparison between 1995 and 2007.Environ Toxicol Chem2014 Jun24549493
Toxicogenomics-based identification of mechanisms for direct immunotoxicity.Toxicol Sci2013 Oct23824090
An integrated approach to model the biomagnification of organic pollutants inaquatic food webs of the Yangtze Three Gorges Reservoir ecosystem using adaptedpollution scenarios.Environ Sci Pollut Res Int2013 Oct23370849
Occurrence and distribution study of residues from pesticides applied undercontrolled conditions in the field during rice processing.J Agric Food Chem2012 May 922497619
Comparison of extraction solvents and conditions for herbicide residues in milledrice with liquid chromatography-diode array detection analysis (LC-DAD).Food Addit Contam Part A Chem Anal Control Expo Risk Assess2010Feb20013445
A multi-residue method for pesticide residue analysis in rice grains using matrixsolid-phase dispersion extraction and high-performance liquidchromatography-diode array detection.Anal Bioanal Chem2010 Jul20379813
Are Portuguese Echinochloa spp. populations still susceptible to propanil?Commun Agric Appl Biol Sci200920222612
Short- and long-term responses of Daphnia spp. to propanil exposures in distinct food supply scenarios.Ecotoxicol Environ Saf2007 Nov17150251
[Occupational and environmental exposure to anilide and dicarboximidepesticides].G Ital Med Lav Ergon2007 Jul-Sep18409684
Determination of antagonism between cyhalofop-butyl and other rice (Oryza sativa)herbicides in barnyardgrass (Echinochloa crus-galli).J Agric Food Chem2005 May 1815884840
Liquid chromatography-electrospray quadrupole ion-trap mass spectrometry of nine pesticides in fruits.J Chromatogr A2004 Sep 315453417
Electrochemical and spectroscopic studies of the oxidation mechanism of theherbicide propanil.J Agric Food Chem2003 Feb 1212568542
Adsorption-desorption studies of selected herbicides in soil-Fly ash mixtures.J Agric Food Chem2000 Oct11052734
Hydrolysis of naptalam and structurally related amides: inhibition by dissolvedmetal ions and metal (hydr)oxide surfaces.J Agric Food Chem1999 Oct10552829
Excised Barley root uptake of several (14)C labeled organic compounds.Environ Monit Assess1985 Dec24258104