Diflufenican

Basic Info

Common NameDiflufenican(F06182)
2D Structure
FRCD IDF06182
CAS Number83164-33-4
PubChem CID91735
FormulaC19H11F5N2O2
IUPAC Name

N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]pyridine-3-carboxamide

InChI Key

WYEHFWKAOXOVJD-UHFFFAOYSA-N

InChI

InChI=1S/C19H11F5N2O2/c20-12-6-7-16(15(21)10-12)26-17(27)14-5-2-8-25-18(14)28-13-4-1-3-11(9-13)19(22,23)24/h1-10H,(H,26,27)

Canonical SMILES

C1=CC(=CC(=C1)OC2=C(C=CC=N2)C(=O)NC3=C(C=C(C=C3)F)F)C(F)(F)F

Isomeric SMILES

C1=CC(=CC(=C1)OC2=C(C=CC=N2)C(=O)NC3=C(C=C(C=C3)F)F)C(F)(F)F

Synonyms
        
            N-(2,4-Difluorophenyl)-2-(3-(trifluoromethyl)phenoxy)nicotinamide
        
            Diflufenican
        
            83164-33-4
        
            Diflufenicanil
        
            Diflufenican [BSI:ISO]
        
            UNII-3T8D1VDO6K
        
            N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]pyridine-3-carboxamide
        
            BRN 4212494
        
            3T8D1VDO6K
        
            M&B 38544
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassAnilides
Intermediate Tree NodesNot available
Direct ParentAromatic anilides
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsAromatic anilide - Diaryl ether - Trifluoromethylbenzene - Nicotinamide - Pyridine carboxylic acid or derivatives - Pyridinecarboxamide - Phenoxy compound - Phenol ether - Fluorobenzene - Halobenzene - Aryl fluoride - Aryl halide - Pyridine - Heteroaromatic compound - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Ether - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Hydrocarbon derivative - Alkyl halide - Organic oxide - Alkyl fluoride - Organopnictogen compound - Organic oxygen compound - Organohalogen compound - Organofluoride - Organonitrogen compound - Organooxygen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group.

Properties

Property NameProperty Value
Molecular Weight394.301
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Complexity533
Monoisotopic Mass394.074
Exact Mass394.074
XLogP4.6
Formal Charge0
Heavy Atom Count28
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+0.9930
Human Intestinal AbsorptionHIA+0.9951
Caco-2 PermeabilityCaco2+0.5388
P-glycoprotein SubstrateNon-substrate0.8370
P-glycoprotein InhibitorNon-inhibitor0.5986
Non-inhibitor0.8494
Renal Organic Cation TransporterNon-inhibitor0.8488
Distribution
Subcellular localizationMitochondria0.7962
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8445
CYP450 2D6 SubstrateNon-substrate0.8088
CYP450 3A4 SubstrateNon-substrate0.5140
CYP450 1A2 InhibitorInhibitor0.9107
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.6465
CYP450 2C19 InhibitorInhibitor0.8994
CYP450 3A4 InhibitorNon-inhibitor0.7830
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.8123
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9821
Non-inhibitor0.7973
AMES ToxicityNon AMES toxic0.7720
CarcinogensNon-carcinogens0.8609
Fish ToxicityHigh FHMT0.8223
Tetrahymena Pyriformis ToxicityHigh TPT0.9803
Honey Bee ToxicityLow HBT0.8227
BiodegradationNot ready biodegradable0.9964
Acute Oral ToxicityIII0.7820
Carcinogenicity (Three-class)Non-required0.5062
Model Value Unit
Absorption
Aqueous solubility-4.3017LogS
Caco-2 Permeability1.7457LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.3266LD50, mol/kg
Fish Toxicity0.9078pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.1236pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.01*26/04/2017
Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe...0632010European Union0.05*26/04/2017
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.01*26/04/2017
Citrus fruits0110000European Union0.01*26/04/2017
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*26/04/2017
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*26/04/2017
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*26/04/2017
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*26/04/2017
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.01*26/04/2017
Others (2)0110990European Union0.01*26/04/2017
Tree nuts0120000European Union0.01*26/04/2017
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.01*26/04/2017
Brazil nuts0120020European Union0.01*26/04/2017
Cashew nuts0120030European Union0.01*26/04/2017
Chestnuts0120040European Union0.01*26/04/2017
Coconuts (Areca nuts/betel nuts,)0120050European Union0.01*26/04/2017
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.01*26/04/2017
Macadamias0120070European Union0.01*26/04/2017
Pecans (Hickory nuts,)0120080European Union0.01*26/04/2017
Pistachios0120100European Union0.01*26/04/2017

References

TitleJournalDatePubmed ID
Simultaneous determination of 124 pesticide residues in Chinese liquor andliquor-making raw materials (sorghum and rice hull) by rapid Multi-plugFiltration Cleanup and gas chromatography-tandem mass spectrometry.Food Chem2018 Feb 1528958527
Residues of plant protection products in grey partridge eggs in French cerealecosystems.Environ Sci Pollut Res Int2016 May26841780
Pesticide pressure and fish farming in barrage pond in northeastern France. Part III: how management can affect pesticide profiles in edible fish?Environ Sci Pollut Res Int2013 Jan22467231
Accumulation and half-lives of 13 pesticides in muscle tissue of freshwaterfishes through food exposure.Chemosphere2013 Apr23374295
Characterization of a higher plant herbicide-resistant phytoene desaturase andits use as a selectable marker.Plant Biotechnol J2006 Mar17177802
Elimination of pesticides in olive oil by refining using bleaching anddeodorization.Food Addit Contam2005 Jan15895608
Soil dissipation of diuron, chlorotoluron, simazine, propyzamide, anddiflufenican herbicides after repeated applications in fruit tree orchards.Arch Environ Contam Toxicol2000 Jul10790503