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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:24 UTC
Update Date2022-03-07 02:53:06 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. Based on a literature review a small amount of articles have been published on Diflubenzuron.
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point230 - 232 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.88Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+167.95930932474
DeepCCS[M-H]-165.60130932474
DeepCCS[M-2H]-198.48630932474
DeepCCS[M+Na]+174.05230932474
AllCCS[M+H]+166.032859911
AllCCS[M+H-H2O]+162.632859911
AllCCS[M+NH4]+169.232859911
AllCCS[M+Na]+170.132859911
AllCCS[M-H]-163.332859911
AllCCS[M+Na-2H]-162.532859911
AllCCS[M+HCOO]-161.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DiflubenzuronFC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C13729.5Standard polar33892256
DiflubenzuronFC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C12238.5Standard non polar33892256
DiflubenzuronFC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C12472.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Diflubenzuron,1TMS,isomer #1C[Si](C)(C)N(C(=O)NC1=CC=C(Cl)C=C1)C(=O)C1=C(F)C=CC=C1F2478.8Semi standard non polar33892256
Diflubenzuron,1TMS,isomer #1C[Si](C)(C)N(C(=O)NC1=CC=C(Cl)C=C1)C(=O)C1=C(F)C=CC=C1F2156.0Standard non polar33892256
Diflubenzuron,1TMS,isomer #2C[Si](C)(C)N(C(=O)NC(=O)C1=C(F)C=CC=C1F)C1=CC=C(Cl)C=C12421.8Semi standard non polar33892256
Diflubenzuron,1TMS,isomer #2C[Si](C)(C)N(C(=O)NC(=O)C1=C(F)C=CC=C1F)C1=CC=C(Cl)C=C12130.7Standard non polar33892256
Diflubenzuron,2TMS,isomer #1C[Si](C)(C)N(C(=O)C1=C(F)C=CC=C1F)C(=O)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C2393.3Semi standard non polar33892256
Diflubenzuron,2TMS,isomer #1C[Si](C)(C)N(C(=O)C1=C(F)C=CC=C1F)C(=O)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C2258.0Standard non polar33892256
Diflubenzuron,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)NC1=CC=C(Cl)C=C1)C(=O)C1=C(F)C=CC=C1F2714.2Semi standard non polar33892256
Diflubenzuron,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)NC1=CC=C(Cl)C=C1)C(=O)C1=C(F)C=CC=C1F2385.8Standard non polar33892256
Diflubenzuron,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)NC(=O)C1=C(F)C=CC=C1F)C1=CC=C(Cl)C=C12673.7Semi standard non polar33892256
Diflubenzuron,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)NC(=O)C1=C(F)C=CC=C1F)C1=CC=C(Cl)C=C12310.5Standard non polar33892256
Diflubenzuron,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=C(F)C=CC=C1F)C(=O)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C2856.1Semi standard non polar33892256
Diflubenzuron,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=C(F)C=CC=C1F)C(=O)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C2645.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Diflubenzuron GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-3900000000-b680c2ad28b77e05e5032017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diflubenzuron GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0w2c-4900000000-f0884ff1656b3b7f2d352014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron LC-ESI-QFT , negative-QTOFsplash10-0a4r-0962000000-d51ae063ca121dd27bda2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron LC-ESI-QTOF , positive-QTOFsplash10-0bt9-0906000000-0b7a683feaa5206114762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0900000000-9df798aa7bd11cb4cabe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron LC-ESI-QTOF , positive-QTOFsplash10-0a4l-0900000000-628b33107aaf0a0d11252017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-4bf354a6174bfbe77b0f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-580323bf304d52f2a7a02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron LC-ESI-QFT , positive-QTOFsplash10-0a4i-0900000000-e2755cab4c400036ab0e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron 10V, Positive-QTOFsplash10-0a4r-0973000000-59b43d9b3fdc5a0df36e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron 20V, Negative-QTOFsplash10-0udi-0900000000-7d99395519cf39ad79f62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron 35V, Negative-QTOFsplash10-0a4r-0962000000-f036463cb6a9347053402021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron 35V, Positive-QTOFsplash10-0a4i-0900000000-a671c6d032e157baec462021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron 30V, Negative-QTOFsplash10-0ufr-0900000000-7517166be9d69f58f6422021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron 10V, Negative-QTOFsplash10-0a4r-0973000000-5a5b699f42690cfd9ab12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron 50V, Positive-QTOFsplash10-0006-0900000000-580323bf304d52f2a7a02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron 10V, Positive-QTOFsplash10-0bt9-0906000000-0b7a683feaa5206114762021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron 20V, Positive-QTOFsplash10-0a4i-0900000000-9df798aa7bd11cb4cabe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron 40V, Positive-QTOFsplash10-0006-0900000000-4bf354a6174bfbe77b0f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron 40V, Positive-QTOFsplash10-0a4l-0900000000-628b33107aaf0a0d11252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diflubenzuron 15V, Negative-QTOFsplash10-0a4r-0940000000-c258340c00adb9d006d92021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diflubenzuron 10V, Positive-QTOFsplash10-03di-0908000000-58c6578d7e8cae5e0ef32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diflubenzuron 20V, Positive-QTOFsplash10-054o-0900000000-83f081a44a04f3e658aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diflubenzuron 40V, Positive-QTOFsplash10-0f6x-1900000000-841a7ed4e9898913cda92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diflubenzuron 10V, Negative-QTOFsplash10-0a4i-0906000000-3ec78cf089d639c9a7e72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diflubenzuron 20V, Negative-QTOFsplash10-056r-0901000000-846cf6d32dfbaf7620612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diflubenzuron 40V, Negative-QTOFsplash10-01t9-2900000000-c53ab8ad51c1beca63522016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
MarkerDB IDNot Available
Good Scents 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.. .