Chlorfluazuron

Basic Info

Common NameChlorfluazuron(F05991)
2D Structure
FRCD IDF05991
CAS Number71422-67-8
PubChem CID91708
FormulaC20H9Cl3F5N3O3
IUPAC Name

N-[[3,5-dichloro-4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]carbamoyl]-2,6-difluorobenzamide

InChI Key

UISUNVFOGSJSKD-UHFFFAOYSA-N

InChI

InChI=1S/C20H9Cl3F5N3O3/c21-10-5-9(30-19(33)31-17(32)15-13(24)2-1-3-14(15)25)6-11(22)16(10)34-18-12(23)4-8(7-29-18)20(26,27)28/h1-7H,(H2,30,31,32,33)

Canonical SMILES

C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC(=C(C(=C2)Cl)OC3=C(C=C(C=N3)C(F)(F)F)Cl)Cl)F

Isomeric SMILES

C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC(=C(C(=C2)Cl)OC3=C(C=C(C=N3)C(F)(F)F)Cl)Cl)F

Synonyms
        
            Chlorfluazuron [ISO]
        
            Chlorfluazuron
        
            71422-67-8
        
            Atabron
        
            UNII-Q42JG8449K
        
            CCRIS 2680
        
            Cga-112913
        
            IKI 7899
        
            PP 145
        
            CGA 112913
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassN-phenylureas
Intermediate Tree NodesN-acyl-phenylureas
Direct ParentN-benzoyl-N'-phenylureas
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsN-benzoyl-n'-phenylurea - Diaryl ether - 2-halobenzoic acid or derivatives - Halobenzoic acid or derivatives - Benzoic acid or derivatives - Phenoxy compound - 1,3-dichlorobenzene - Phenol ether - Benzoyl - Fluorobenzene - Chlorobenzene - Halobenzene - Aryl halide - Aryl fluoride - Pyridine - Aryl chloride - Vinylogous halide - Heteroaromatic compound - Carbonic acid derivative - Urea - Carboxylic acid derivative - Azacycle - Organoheterocyclic compound - Ether - Organic nitrogen compound - Organooxygen compound - Alkyl halide - Alkyl fluoride - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organofluoride - Organochloride - Organohalogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as n-benzoyl-n'-phenylureas. These are n-acyl-phenylureas that have the acyl group substituted by a phenyl group.

Properties

Property NameProperty Value
Molecular Weight540.652
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Complexity715
Monoisotopic Mass538.963
Exact Mass538.963
XLogP6.7
Formal Charge0
Heavy Atom Count34
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+0.9696
Human Intestinal AbsorptionHIA+0.9727
Caco-2 PermeabilityCaco2-0.5412
P-glycoprotein SubstrateNon-substrate0.7034
P-glycoprotein InhibitorNon-inhibitor0.7500
Non-inhibitor0.9438
Renal Organic Cation TransporterNon-inhibitor0.8820
Distribution
Subcellular localizationMitochondria0.7017
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7365
CYP450 2D6 SubstrateNon-substrate0.8388
CYP450 3A4 SubstrateNon-substrate0.6159
CYP450 1A2 InhibitorInhibitor0.5537
CYP450 2C9 InhibitorNon-inhibitor0.8137
CYP450 2D6 InhibitorNon-inhibitor0.8494
CYP450 2C19 InhibitorInhibitor0.5495
CYP450 3A4 InhibitorNon-inhibitor0.9064
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6236
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9652
Non-inhibitor0.7804
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.8142
Fish ToxicityHigh FHMT0.8547
Tetrahymena Pyriformis ToxicityHigh TPT0.9902
Honey Bee ToxicityLow HBT0.8856
BiodegradationNot ready biodegradable0.9958
Acute Oral ToxicityII0.7450
Carcinogenicity (Three-class)Non-required0.5609
Model Value Unit
Absorption
Aqueous solubility-4.7718LogS
Caco-2 Permeability1.1974LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.0538LD50, mol/kg
Fish Toxicity1.1029pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.0828pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
PearJapan2. oppm

References

TitleJournalDatePubmed ID
Dispersive micro-solid-phase extraction of benzoylurea insecticides in honeysamples with a β-cyclodextrin-modified attapulgite composite as sorbent.J Sep Sci2016 Jan26573895
Ionic liquid-assisted liquid-phase microextraction based on the solidification offloating organic droplets combined with high performance liquid chromatographyfor the determination of benzoylurea insecticide in fruit juice.J Chromatogr A2014 Sep 1925124227
Colony Size Affects the Efficacy of Bait Containing Chlorfluazuron Against the Fungus-Growing Termite Macrotermes gilvus (Blattodea: Termitidae).J Econ Entomol2014 Dec26470081
[Determination of chlorfluazuron residue in foods by high performance liquidchromatography].Se Pu2011 Dec22500454
Effectiveness of pressurized liquid extraction and solvent extraction for thesimultaneous quantification of 14 pesticide residues in green tea using GC.J Sep Sci2008 Jun18481329
Field evaluation of the bait toxicant chlorfluazuron in eliminating Coptotermesacinaciformis (Froggatt) (Isoptera: Rhinotermitidae).J Econ Entomol2003 Dec14977122
Monitoring of pesticide residues on cucumber, tomatoes and strawberries in GazaGovernorates, Palestine.Nahrung2002 Feb11890053
Development of a compound-specific ELISA for flufenoxuron and an improvedclass-specific assay for benzoylphenylurea insect growth regulators.J Agric Food Chem1999 Aug10552666