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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:24 UTC
Update Date2019-07-23 06:09:29 UTC
HMDB IDHMDB0031778
Secondary Accession Numbers
  • HMDB31778
Metabolite Identification
Common NameDiflubenzuron
DescriptionDiflubenzuron, also known as dimilin or difluron, 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. It is used on soya beans, citrus, tea, vegetables and mushroomsand is also used as an insecticide in feed for poultry and pigs and as a controlled release bolus in cattle. Diflubenzuron is an extremely weak basic (essentially neutral) compound (based on its pKa). Diflubenzuron is a potentially toxic compound. One of the metabolites of diflubenzuron, PCA, is a proximate carcinogen. It is conjugated to form the carcinogen that can ionize and reat with DNA to form adducts which result in splenic tumor formation. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of an urea group. One of the metabolites of diflubenzuron, PCA, has severe health effects. Diflubenzuron is used on soya beans, citrus, tea, vegetables and mushrooms.
Structure
Data?1563862169
Synonyms
ValueSource
1-(4-Chlorophenyl)-3-(2,6-difluorobenzoyl)ureaChEBI
1-(p-Chlorophenyl)-3-(2,6-difluorobenzoyl)ureaChEBI
DifluronChEBI
N-(4-Chlorophenylcarbamoyl)-2,6-difluorobenzamideChEBI
N-{[(4-chlorophenyl)amino]carbonyl}-2,6-difluorobenzamideChEBI
1-(p-Chlorophenyl)-3-(2,6-difluorobenzoyl)-ureaHMDB
AstonexHMDB
DimilinHMDB
Dimilin g1HMDB
Dimilin g4HMDB
Dimilin ODC-45HMDB
Dimilin wp-25HMDB
DioflubenzuronHMDB
DuphacidHMDB
LarvakilHMDB
MicromiteHMDB
N-(((4-Chlorophenyl)amino)carbonyl)-2,6-difluorobenzamideHMDB
N-(4-Chlorophenyl)-n'-(2,6-difluorobenzoyl)ureaHMDB
N-[(4-Chlorophenyl)carbamoyl]-2,6-difluorobenzamideHMDB
N-[[(4-Chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide, 9ciHMDB
N-[[(4-Chlorophenyl)amno]carbonyl]-2,6-difluorobenzamideHMDB
Philips-duphar PH 60-40HMDB
Thompson hayward 6040HMDB
Thompson-hayward 6040HMDB
Thompson-hayward TH6040HMDB
Chemical FormulaC14H9ClF2N2O2
Average Molecular Weight310.683
Monoisotopic Molecular Weight310.032061659
IUPAC Name3-(4-chlorophenyl)-1-(2,6-difluorobenzoyl)urea
Traditional Name3-(4-chlorophenyl)-1-(2,6-difluorobenzoyl)urea
CAS Registry Number35367-38-5
SMILES
FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C14H9ClF2N2O2/c15-8-4-6-9(7-5-8)18-14(21)19-13(20)12-10(16)2-1-3-11(12)17/h1-7H,(H2,18,19,20,21)
InChI KeyQQQYTWIFVNKMRW-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassN-phenylureas
Direct ParentN-benzoyl-N'-phenylureas
Alternative Parents
Substituents
  • N-benzoyl-n'-phenylurea
  • Halobenzoic acid or derivatives
  • 2-halobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzoyl
  • Chlorobenzene
  • Fluorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl fluoride
  • Aryl halide
  • Vinylogous halide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point230 - 232 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.88Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.006 g/LALOGPS
logP3.93ALOGPS
logP3.61ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.05ChemAxon
pKa (Strongest Basic)-8.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.07 m³·mol⁻¹ChemAxon
Polarizability27.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-3900000000-b680c2ad28b77e05e503Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4r-0962000000-d51ae063ca121dd27bdaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0bt9-0906000000-0b7a683feaa520611476Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-9df798aa7bd11cb4cabeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4l-0900000000-628b33107aaf0a0d1125Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-4bf354a6174bfbe77b0fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-580323bf304d52f2a7a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0900000000-e2755cab4c400036ab0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0908000000-58c6578d7e8cae5e0ef3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054o-0900000000-83f081a44a04f3e658aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-1900000000-841a7ed4e9898913cda9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0906000000-3ec78cf089d639c9a7e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0901000000-846cf6d32dfbaf762061Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-2900000000-c53ab8ad51c1beca6352Spectrum
MSMass Spectrum (Electron Ionization)splash10-0w2c-4900000000-f0884ff1656b3b7f2d35Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008451
KNApSAcK IDNot Available
Chemspider ID34065
KEGG Compound IDC14427
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiflubenzuron
METLIN IDNot Available
PubChem Compound37123
PDB IDNot Available
ChEBI ID34703
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .