Linuron

Names

[ CAS No. ]:
330-55-2

[ Name ]:
Linuron

[Synonym ]:
Lorex
EINECS 206-356-5
3-(3,4-Dichlorophenyl)-1-methoxy-1-methylurea
Linuron
Laroks
Urea, N'-(3,4-dichlorophenyl)-N-methoxy-N-methyl-
AFALON
LOROX
MFCD00055249
Afolan
Liron
Methanol, 1-[(3,4-dichlorophenyl)imino]-1-(methoxymethylamino)-, (E)-
LINEX
LINNET
N’-(3,4-dichlorophenyl)-N-methoxy-N-methylurea
LINUREX

Biological Activity

[Description]:

Linuron is a phenylurea herbicide that is widely used to control the growth of grass and weeds in various agriculture crops and in orchards. Linuron is a photosystem II inhibitor. Linuron is also a competitive androgen receptor (AR) antagonist with a Ki of 100 μM. Linuron shows reproductive toxicity in animals that acts as an endocrine disruptor[1][2][3][4].

[Related Catalog]:

Research Areas >> Endocrinology

Signaling Pathways >> Others >> Androgen Receptor

[Target]

Ki: 100 μM (Androgen receptor)[2] Photosystem II[4]

[References]

[1]. Benjamin Horemans, et al. Functional Redundancy of Linuron Degradation in Microbial Communities in Agricultural Soil and Biopurification Systems. Appl Environ Microbiol. 2016 Apr 18;82(9):2843-2853.

[2]. C Lambright, et al. Cellular and Molecular Mechanisms of Action of Linuron: An Antiandrogenic Herbicide That Produces Reproductive Malformations in Male Rats. Toxicol Sci. 2000 Aug;56(2):389-99.

[3]. Hongwei Ding, et al. Reproductive Toxicity of Linuron Following Gestational Exposure in Rats and Underlying Mechanisms. Toxicol Lett. 2017 Jan 15;266:49-55.

[4]. Elżbieta G Magnucka, et al. Various Effects of the Photosystem II--inhibiting Herbicides on 5-n-alkylresorcinol Accumulation in Rye Seedlings. Pestic Biochem Physiol. 2014 Nov;116:56-62.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
361.7±52.0 °C at 760 mmHg

[ Melting Point ]:
93-94°C

[ Molecular Formula ]:
C₉H₁₀Cl₂N₂O₂

[ Molecular Weight ]:
249.094

[ Flash Point ]:
172.6±30.7 °C

[ Exact Mass ]:
248.011932

[ PSA ]:
41.57000

[ LogP ]:
3.33

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.556

[ Water Solubility ]:
0.0075 g/100 mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YS9100000

CHEMICAL NAME :: Urea, 3-(3,4-dichlorophenyl)-1-methoxy-1-methyl-

CAS REGISTRY NUMBER :: 330-55-2

LAST UPDATED :: 199710

DATA ITEMS CITED :: 23

MOLECULAR FORMULA :: C9-H10-Cl2-N2-O2

MOLECULAR WEIGHT :: 249.11

WISWESSER LINE NOTATION :: GR BG DMVN1&O1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1146 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 48 mg/m3/4H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 3765 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10 gm/kg/60D-C

TOXIC EFFECTS :: Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - catalases Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other oxidoreductases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1070 mg/kg/31W-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other Enzymes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 10 gm/kg/10D-I

TOXIC EFFECTS :: Cardiac - EKG changes not diagnostic of specified effects Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 7500 mg/kg/30D-I

TOXIC EFFECTS :: Behavioral - muscle weakness Cardiac - EKG changes not diagnostic of specified effects Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - domestic

DOSE/DURATION :: 1750 mg/kg/7D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - muscle weakness Related to Chronic Data - death

TYPE OF TEST :: DNA damage

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 58,353,1978 *** REVIEWS *** TOXICOLOGY REVIEW DTTIAF Deutsche Tieraerztliche Wochenschrift. (Hanover, Fed. Rep. Ger.) V.1-77, 1893-1970. Volume(issue)/page/year: 80,485,1973 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 1 mg/m3 JAN 1993

Safety Information

[ Symbol ]:

GHS07, GHS08, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H351-H360Df-H373-H410

[ Precautionary Statements ]:
P201-P273-P281-P308 + P313-P501

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
N,T,F

[ Risk Phrases ]:
R61

[ Safety Phrases ]:
S53-S45-S60-S61-S36/37

[ RIDADR ]:
UN 3077

[ RTECS ]:
YS9100000

[ HS Code ]:
2928000032

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2928000032

[ Summary ]:
2928000032 3-(4-bromo-3-chlorophenyl)-1-methoxy-1-methylurea。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:9.0%。MFN tarrif:6.5%。general tariff:20.0%

Articles

LC-MS analysis of the plasma metabolome--a novel sample preparation strategy.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 978-979 , 83-8, (2015)

Blood plasma is a well-known body fluid often analyzed in studies on the effects of toxic compounds as physiological or chemical induced changes in the mammalian body are reflected in the plasma metab...

Occurrence and distribution of sulfonylurea and related herbicides in central Canadian surface waters 2006-2008.

Bull. Environ. Contam. Toxicol. 87(4) , 420-5, (2011)

Surface water sampling in 2006-2008 measured the occurrence of sulfonylureas and related herbicides (SUs) during base flow conditions and wet weather events. Flumetsulam (29.2%), diuron (36.5%) and fo...

Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.

J. Med. Chem. 51 , 6740-51, (2008)

The work provides a new model for the prediction of the MAO-A and -B inhibitor activity by the use of combined complex networks and QSAR methodologies. On the basis of the obtained model, we prepared ...