ContaminantDB: Linuron

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (9)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:51:44 UTC

Update Date

2026-03-31 19:09:24 UTC

Accession Number

CHEM003478

Identification

Common Name

Linuron

Class

Small Molecule

Description

Linuron is an herbicide for the pre- and post-emergence control of annual grass and broad-leaved weeds using selective and systemic action with contact and residual action. It is known to inhibit photosynthesis (photosystem II).

Contaminant Sources

Clean Air Act Chemicals
EPA Endocrine Screening
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Herbicide
Organic Compound
Organochloride
Pesticide
Synthetic Compound

Chemical Structure

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

Synonyms

Value	Source
1-Methoxy-1-methyl-3-(3,4-dichlorophenyl)urea	ChEBI
3-(3,4-Dichlorophenyl)-1-methoxy-1-methylurea	ChEBI
N'-(3,4-dichlorophenyl)-N-methoxy-N-methyl urea	ChEBI
Afalon	MeSH

Chemical Formula

C₉H₁₀Cl₂N₂O₂

Average Molecular Mass

249.094 g/mol

Monoisotopic Mass

248.012 g/mol

CAS Registry Number

330-55-2

IUPAC Name

1-(3,4-dichlorophenyl)-3-methoxy-3-methylurea

Traditional Name

linuron

SMILES

CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1

InChI Identifier

InChI=1S/C9H10Cl2N2O2/c1-13(15-2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14)

InChI Key

XKJMBINCVNINCA-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-phenylureas. N-phenylureas are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

N-phenylureas

Direct Parent

N-phenylureas

Alternative Parents

Substituents

N-phenylurea
1,2-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Carbonic acid derivative
Organic nitrogen compound
Organochloride
Organohalogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ureas (CHEBI:6482 )
dichlorobenzene (CHEBI:6482 )
Phenylurea herbicides (C11007 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Lysosome
Membrane
Mitochondrion
Peroxisome
Plasma Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Metabolic Pathways	Not Available	Not Available
Aflatoxin Biosynthesis	Not Available	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	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	2.82	ALOGPS
logP	2.68	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.35 m³·mol⁻¹	ChemAxon
Polarizability	23.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-3910000000-06403414f74cd43e045e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-053r-0900000000-58defb2ae9c51a83691e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0a59-0900000000-fc28f465e47143fb5927	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0a59-0900000000-63e2a0b93419ffc4eafb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0bu1-1930000000-ab84eba117f7c5ab98ad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0f6t-0890000000-f1b31df027603c7cd878	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a5a-0940000000-4c2350ca6138da576cdf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-0a59-0900000000-248384e486fe00066678	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-06si-0900000000-7190cc3af8bf9fde6ef9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0002-0190000000-43475d3d09de3d66940a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0a4i-0910000000-f709c06637f21ffef280	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-01q9-0900000000-c2ba2c42df804483c4bf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-053r-0900000000-5f48adbb98c12803d608	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4i-0910000000-59ba8adaef398a8bd29a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0a4i-0920000000-4e379a2e3c68a80a9f39	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-03dj-0970000000-7fc321d13458dd5f03f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0bt9-0950000000-3807c2876fc72308cc65	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-001i-0900000000-d7ad86577f8019000d68	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0002-0910000000-5f4398f81ba0940aa138	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-08gi-0900000000-844c0e7b8f1bae30354d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-2390000000-69016a05781705508d3e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9340000000-21d61a1ea4afdade4fdf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-8900000000-3ceff76441f309a84632	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1090000000-09719403e6831b7d7ae5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02tj-1490000000-00d02fd3109d9782a7cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0550-9700000000-8e7c824eb58d822210ad	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9200000000-02a9a624235ddb48448d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Linuron is a weak competitive inhibitor of androgen receptor binding and it inhibits androgen-induced gene expression in vitro. This may partially contribute to the malformations of androgen-dependent tissues in male rats. (1)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Linuron affects the male reproductive system of the offspring after maternal exposure during mid and late pregnancy.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Linuron

Chemspider ID

Not Available

ChEBI ID

6482

PubChem Compound ID

9502

Kegg Compound ID

C11007

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23586778

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24410802

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25238184

Linuron (CHEM003478)

Structure for CHEM003478: Linuron