T3DB: Diflubenzuron

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (2)XML

Targets (2)

Record Information

Version

2.0

Creation Date

2014-09-11 05:22:35 UTC

Update Date

2014-12-24 20:26:59 UTC

Accession Number

T3D4921

Identification

Common Name

Diflubenzuron

Class

Small Molecule

Description

Insecticide, 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 Formula

C₁₄H₉ClF₂N₂O₂

Average Molecular Mass

310.683 g/mol

Monoisotopic Mass

310.032 g/mol

CAS Registry Number

35367-38-5

IUPAC Name

3-(4-chlorophenyl)-1-(2,6-difluorobenzoyl)urea

Traditional Name

3-(4-chlorophenyl)-1-(2,6-difluorobenzoyl)urea

SMILES

OC(=NC(=O)NC1=CC=C(Cl)C=C1)C1=C(F)C=CC=C1F

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 Key

InChIKey=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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

N-phenylureas

Direct Parent

N-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

monochlorobenzenes (CHEBI:34703 )
benzoylurea insecticide (CHEBI:34703 )
Pesticides (C14427 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	230 - 232 °C
Boiling Point	Not Available
Solubility	Not Available
LogP	3.88

Predicted Properties

Property	Value	Source
Water Solubility	0.006 g/L	ALOGPS
logP	3.93	ALOGPS
logP	3.61	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.05	ChemAxon
pKa (Strongest Basic)	-8.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.07 m³·mol⁻¹	ChemAxon
Polarizability	27.85 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-3900000000-b680c2ad28b77e05e503	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4r-0962000000-d51ae063ca121dd27bda	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0bt9-0906000000-0b7a683feaa520611476	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-9df798aa7bd11cb4cabe	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4l-0900000000-628b33107aaf0a0d1125	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0900000000-4bf354a6174bfbe77b0f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0900000000-580323bf304d52f2a7a0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4i-0900000000-e2755cab4c400036ab0e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0973000000-59b43d9b3fdc5a0df36e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-7d99395519cf39ad79f6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4r-0962000000-f036463cb6a934705340	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4i-0900000000-a671c6d032e157baec46	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0ufr-0900000000-7517166be9d69f58f642	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-0973000000-5a5b699f42690cfd9ab1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0006-0900000000-580323bf304d52f2a7a0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0bt9-0906000000-0b7a683feaa520611476	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-9df798aa7bd11cb4cabe	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0900000000-4bf354a6174bfbe77b0f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-0900000000-628b33107aaf0a0d1125	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0a4r-0940000000-c258340c00adb9d006d9	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0908000000-58c6578d7e8cae5e0ef3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-054o-0900000000-83f081a44a04f3e658aa	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-1900000000-841a7ed4e9898913cda9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0906000000-3ec78cf089d639c9a7e7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-0901000000-846cf6d32dfbaf762061	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-2900000000-c53ab8ad51c1beca6352	2016-08-03	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0w2c-4900000000-f0884ff1656b3b7f2d35	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.40 MHz, DMSO-d6, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

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.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

para-Chloroaniline is possibly carcinogenic to humans (Group 2B). (4)

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

One 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.

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB31778

PubChem Compound ID

37123

ChEMBL ID

Not Available

ChemSpider ID

34065

KEGG ID

C14427

UniProt ID

Not Available

OMIM ID

ChEBI ID

34703

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D4921.pdf

General References

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 ]
Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Fluoride Action Network Pesticide Project - Diflubenzuron [Link]
International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Aryl hydrocarbon receptor

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

Type	Value	Assay Type	Assay Source
AC50	0.0553 uM	Tox21_AhR	Tox21/NCGC

References

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 ]

Target Details

2. Peroxisome proliferator-activated receptor gamma

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

Type	Value	Assay Type	Assay Source
AC50	0.912 uM	ATG_PPARg_TRANS	Attagene

References

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 ]

Diflubenzuron (T3D4921)

Structure for T3D4921: Diflubenzuron

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References