LINURON

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H10Cl2N2O2
Molecular Weight	249.094
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=XKJMBINCVNINCA-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C9H10Cl2N2O2
Molecular Weight	249.094
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Effects of Common Pesticides on Prostaglandin D2 (PGD2) Inhibition in SC5 Mouse Sertoli Cells, Evidence of Binding at the COX-2 Active Site, and Implications for Endocrine Disruption.	2016-04	26359731
Species-specific considerations in using the fish embryo test as an alternative to identify endocrine disruption.	2014-10	24992288
A concentration addition model to assess activation of the pregnane X receptor (PXR) by pesticide mixtures found in the French diet.	2014-09	25028461
Exposure to the pesticide linuron affects androgen-dependent gene expression in the three-spined stickleback (Gasterosteus aculeatus).	2012-06	22514014
A mixture of an environmentally realistic concentration of a phthalate and herbicide reduces testosterone in male fathead minnow (Pimephales promelas) through a novel mechanism of action.	2012-04	22277248
Widely used pesticides with previously unknown endocrine activity revealed as in vitro antiandrogens.	2011-06	21310686
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.	2011-03-28	21251949
Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays.	2011-02-27	21115097
Response to mixed substrate feeds of the structure and activity of a linuron-degrading triple-species biofilm.	2010-10	20600856
Optimization and prevalidation of the in vitro AR CALUX method to test androgenic and antiandrogenic activity of compounds.	2010-08	20438827
Cell viability and PSA secretion assays in LNCaP cells: a tiered in vitro approach to screen chemicals with a prostate-mediated effect on male reproduction within the ReProTect project.	2010-08	20363314
Assessment of a recombinant androgen receptor binding assay: initial steps towards validation.	2010-08	19833195
Endocrine disruptors and Leydig cell function.	2010	20862379
Interactions of methoxyacetic acid with androgen receptor.	2009-07-15	18486176
Toxicity of herbicides to cyanobacterial isolates.	2009-05	20120462
The herbicide linuron reduces testosterone production from the fetal rat testis during both in utero and in vitro exposures.	2009-04-25	19167474
In vitro screening for aryl hydrocarbon receptor agonistic activity in 200 pesticides using a highly sensitive reporter cell line, DR-EcoScreen cells, and in vivo mouse liver cytochrome P450-1A induction by propanil, diuron and linuron.	2008-12	18835618
Architecture and spatial organization in a triple-species bacterial biofilm synergistically degrading the phenylurea herbicide linuron.	2008-05	18373685
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008-04	18324785
Diverse mechanisms of anti-androgen action: impact on male rat reproductive tract development.	2008-04	18315717
Oxygen consumption by Daphnia magna Straus as a marker of chemical stress in the aquatic environment.	2007-09	17705661
Measurement uncertainty arising from trueness of the analysis of two endocrine disruptors and their metabolites in environmental samples. Part I: ultrasonic extraction from diverse sediment matrices.	2007-04-06	17339040
Measurement uncertainty arising from trueness of the analysis of two endocrine disruptors and their metabolites in environmental samples. Part II. Solid-phase extraction from environmental natural waters.	2007-04-06	17307194
Effects of various pesticides on human 5alpha-reductase activity in prostate and LNCaP cells.	2007-04	17218080
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Fate of diuron and linuron in a field lysimeter experiment.	2006-01-07	16397107
Behavior of two phenyl urea herbicides in clayey soils and effect of alternating dry-wet conditions on their availability.	2006	16893777
Gene expression profiling of androgen receptor antagonists in the rat fetal testis reveals few common gene targets.	2006	16498641
Spatial variability in the mineralisation of the phenylurea herbicide linuron within a Danish agricultural field: multivariate correlation to simple soil parameters.	2005-09	15739226
An in vivo bioassay for detecting antiandrogens using humanized transgenic mice coexpressing the tetracycline-controlled transactivator and human CYP1B1 gene.	2005-07-26	16040568
Cloning and in vitro expression and characterization of the androgen receptor and isolation of estrogen receptor alpha from the fathead Minnow (Pimephales promelas).	2004-12-01	15597887
Residual and contact herbicide transport through field lysimeters via preferential flow.	2004-11-13	15537936
Enhanced desorption of herbicides sorbed on soils by addition of Triton X-100.	2004-07-01	15224928
Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells.	2004-04	15064155
Phthalate ester-induced gubernacular lesions are associated with reduced insl3 gene expression in the fetal rat testis.	2004-02-02	14687758
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003-10	14565775
Altered gene expression during rat Wolffian duct development in response to in utero exposure to the antiandrogen linuron.	2003-07	12730624
A novel cell line, MDA-kb2, that stably expresses an androgen- and glucocorticoid-responsive reporter for the detection of hormone receptor agonists and antagonists.	2002-03	11861974
Effects of in utero exposure to linuron on androgen-dependent reproductive development in the male Crl:CD(SD)BR rat.	2000-09-01	10964759
Cellular and molecular mechanisms of action of linuron: an antiandrogenic herbicide that produces reproductive malformations in male rats.	2000-08	10910998
Application of an androgen receptor assay for the characterisation of the androgenic or antiandrogenic activity of various phenylurea herbicides and their derivatives.	1998-12	10435283
In vivo studies on enzymatic induction activity of Linuron.	1994	7823289

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:10:08 GMT 2025` Edited by `admin` on `Mon Mar 31 19:10:08 GMT 2025`
Record UNII	01XP1SU59O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LINURON

Common Name

English

LINURON [HSDB]

Preferred Name

English

LINURON [MI]

Common Name

English

3-(3,4-DICHLOROPHENYL)-1-METHOXY-1-METHYLUREA

Systematic Name

English

N'-(3,4-DICHLOROPHENYL)-N-METHOXY-N-METHYLUREA

Systematic Name

English

LINURON [ISO]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

35506