linuron

Synonyms: "methoxydiuron", "afalon", "Aphalon", "Cephalon", "linurex", "linex", "lorox", "afalon inuron", "herbicide 326"

Source: linuron is a herbicide used to control germinating and newly emerging grasses and broad-leafed weeds.

Identifiers:

IUPAC Name: 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea
CAS Number: 330-55-2
PubChem ID: 9502
InChiKey: XKJMBINCVNINCA-UHFFFAOYSA-N
Canonical SMILES: CN(C(=O)NC1=CC(=C(C=C1)Cl)Cl)OC

Structural Properties:

Molecular Formula: C₉H₁₀Cl₂N₂O₂
Molecular Weight: 249.094

Pharmacophore Features:

Number of bond donors: 1
Number of bond acceptors: 2
Number of atoms different from hydrogen: 15

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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Andrews JE, Gray LE. 1990. The effects of lindane and linuron on calcium metabolism, bone morphometry and the kidney in rats. Toxicology 60(1-2):99-107.

Cook JC, Mullin LS, Frame SR, Biegel LB. 1993. Investigation of a mechanism for Leydig cell tumorigenesis by linuron in rats. Toxicol Appl Pharmacol 119(2):195-204.

Kojima H, Katsura E, Takeuchi S, Niiyama K, Kobayashi K. 2004. Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells. Environ Health Perspect 112(5):524-531.

Lambright C, Ostby J, Bobseine K, Wilson V, Hotchkiss AK, Mann PC, Gray LE Jr. 2000. Cellular and molecular mechanisms of action of linuron: an antiandrogenic herbicide that produces reproductive malformations in male rats. Toxicol Sci 56(2):389-399.

Orton F, Lutz I, Kloas W, Routledge EJ. 2009. Endocrine disrupting effects of herbicides and pentachlorophenol: in vitro and in vivo evidence. Environ Sci Technol 43(6):2144-2150.