Tmic
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Record Information
Version2.0
Creation Date2014-09-11 05:22:35 UTC
Update Date2014-12-24 20:26:59 UTC
Accession NumberT3D4921
Identification
Common NameDiflubenzuron
ClassSmall Molecule
DescriptionInsecticide, interfering with chitin deposition by oral absorption. Diflubenzuron is used on soya beans, citrus, tea, vegetables and mushrooms. Also used as an insecticide in feed for poultry and pigs and as a controlled release bolus in cattle Diflubenzuron belongs to the family of N-Phenylureas. 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.
Compound Type
  • Amide
  • Amine
  • Ester
  • Food Toxin
  • Insecticide
  • Metabolite
  • Organic Compound
  • Organochloride
  • Organofluoride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1-(4-Chlorophenyl)-3-(2,6-difluorobenzoyl)urea
1-(p-Chlorophenyl)-3-(2,6-difluorobenzoyl)-Urea
1-(p-Chlorophenyl)-3-(2,6-difluorobenzoyl)urea
Astonex
Difluron
Dimilin
Dimilin G1
Dimilin G4
Dimilin ODC-45
Dimilin WP-25
Dioflubenzuron
Duphacid
Larvakil
Micromite
N-(((4-Chlorophenyl)amino)carbonyl)-2,6-difluorobenzamide
N-(4-Chlorophenyl)-N'-(2,6-difluorobenzoyl)urea
N-(4-Chlorophenylcarbamoyl)-2,6-difluorobenzamide
N-[(4-Chlorophenyl)carbamoyl]-2,6-difluorobenzamide
N-[[(4-Chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide, 9CI
N-[[(4-Chlorophenyl)amno]carbonyl]-2,6-difluorobenzamide
Philips-duphar PH 60-40
Thompson Hayward 6040
Thompson-Hayward 6040
Thompson-hayward TH6040
Chemical FormulaC14H9ClF2N2O2
Average Molecular Mass310.683 g/mol
Monoisotopic Mass310.032 g/mol
CAS Registry Number35367-38-5
IUPAC Name3-(4-chlorophenyl)-1-(2,6-difluorobenzoyl)urea
Traditional Name3-(4-chlorophenyl)-1-(2,6-difluorobenzoyl)urea
SMILESOC(=NC(=O)NC1=CC=C(Cl)C=C1)C1=C(F)C=CC=C1F
InChI IdentifierInChI=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 KeyInChIKey=QQQYTWIFVNKMRW-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point230 - 232 °C
Boiling PointNot Available
SolubilityNot Available
LogP3.88
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-3900000000-b680c2ad28b77e05e503View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4r-0962000000-d51ae063ca121dd27bdaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0bt9-0906000000-0b7a683feaa520611476View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-9df798aa7bd11cb4cabeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4l-0900000000-628b33107aaf0a0d1125View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-4bf354a6174bfbe77b0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-580323bf304d52f2a7a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0900000000-e2755cab4c400036ab0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0908000000-58c6578d7e8cae5e0ef3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054o-0900000000-83f081a44a04f3e658aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-1900000000-841a7ed4e9898913cda9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0906000000-3ec78cf089d639c9a7e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0901000000-846cf6d32dfbaf762061View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-2900000000-c53ab8ad51c1beca6352View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0w2c-4900000000-f0884ff1656b3b7f2d35View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityOne 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.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)para-Chloroaniline is possibly carcinogenic to humans (Group 2B). (4)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsOne of the metabolites of diflubenzuron, PCA, has severe health effects. It is associated with cancer of the spleen and liver and osteosarcomas in male rats. Another metabolite of diflubenzuron also has carcinogenic potential and the same carcinogenic potency as PCA.
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB31778
PubChem Compound ID37123
ChEMBL IDNot Available
ChemSpider ID34065
KEGG IDC14427
UniProt IDNot Available
OMIM ID
ChEBI ID34703
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4921.pdf
General References
  1. de Barros AL, de Souza VV, Navarro SD, Oesterreich SA, Oliveira RJ, Kassuya CA, Arena AC: Genotoxic and mutagenic effects of diflubenzuron, an insect growth regulator, on mice. J Toxicol Environ Health A. 2013;76(17):1003-6. doi: 10.1080/15287394.2013.830585. [24168035 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  3. Fluoride Action Network Pesticide Project - Diflubenzuron [Link]
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Transcription regulatory region dna binding
Specific Function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
Gene Name:
AHR
Uniprot ID:
P35869
Molecular Weight:
96146.705 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.0553 uMTox21_AhRTox21/NCGC
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular Weight:
57619.58 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.912 uMATG_PPARg_TRANSAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]