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Record Information
Creation Date2014-09-11 05:22:35 UTC
Update Date2014-12-24 20:26:59 UTC
Accession NumberT3D4921
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
Dimilin G1
Dimilin G4
Dimilin ODC-45
Dimilin WP-25
N-[[(4-Chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide, 9CI
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
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)
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
  • 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
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
AppearanceWhite powder.
Experimental Properties
Melting Point230 - 232 °C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
Water Solubility0.006 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-3900000000-b680c2ad28b77e05e503JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4r-0962000000-d51ae063ca121dd27bdaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0bt9-0906000000-0b7a683feaa520611476JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-9df798aa7bd11cb4cabeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4l-0900000000-628b33107aaf0a0d1125JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-4bf354a6174bfbe77b0fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-580323bf304d52f2a7a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0900000000-e2755cab4c400036ab0eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0973000000-59b43d9b3fdc5a0df36eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-7d99395519cf39ad79f6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4r-0962000000-f036463cb6a934705340JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4i-0900000000-a671c6d032e157baec46JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0ufr-0900000000-7517166be9d69f58f642JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0973000000-5a5b699f42690cfd9ab1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0006-0900000000-580323bf304d52f2a7a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0bt9-0906000000-0b7a683feaa520611476JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-9df798aa7bd11cb4cabeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-0900000000-4bf354a6174bfbe77b0fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-0900000000-628b33107aaf0a0d1125JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0a4r-0940000000-c258340c00adb9d006d9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0908000000-58c6578d7e8cae5e0ef3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054o-0900000000-83f081a44a04f3e658aaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-1900000000-841a7ed4e9898913cda9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0906000000-3ec78cf089d639c9a7e7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0901000000-846cf6d32dfbaf762061JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-2900000000-c53ab8ad51c1beca6352JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0w2c-4900000000-f0884ff1656b3b7f2d35JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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
PubChem Compound ID37123
ChEMBL IDNot Available
ChemSpider ID34065
UniProt IDNot Available
ChEBI ID34703
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
Synthesis ReferenceNot Available
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


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:
Uniprot ID:
Molecular Weight:
96146.705 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.0553 uMTox21_AhRTox21/NCGC
  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:
Uniprot ID:
Molecular Weight:
57619.58 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.912 uMATG_PPARg_TRANSAttagene
  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 ]