nitrofen

Synonyms: "2,4-dichloro-1-(4-nitrophenoxy)benzene", "nitrochlor", "nitrophen", "nitrafen", "mezotox", "niclofen", "tokkorn", "trizilin"

Source: nitrofen is a herbicide that was used extensively for the control of broad-leaved and grass weeds in cereals and rice.

Identifiers:

IUPAC Name: 2,4-dichloro-1-(4-nitrophenoxy)benzene
CAS Number: 1836-75-5
PubChem ID: 15787
InChiKey: XITQUSLLOSKDTB-UHFFFAOYSA-N
Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])OC2=C(C=C(C=C2)Cl)Cl

Structural Properties:

Molecular Formula: C12H7Cl2NO3
Molecular Weight: 284.095

Pharmacophore Features:

Number of bond donors: 0
Number of bond acceptors: 2
Number of atoms different from hydrogen: 18

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Evidence Supporting This Chemical as an Endocrine Disruptor
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Gray LE Jr., Kavlock RJ, Chernoff N, Ostby J, Ferrel J. 1983. Postnatal developmental alterations following prenatal exposure to the herbicide 2,4-dichlorophenyl-p-nitrophenyl ether: A dose response evaluation in the mouse. Toxicol Appl Pharmacol 67(1):1-14.

Gray LE Jr., Kavlock RJ. 1983. The effects of the herbicide 2,4-dichlorophenyl-p-nitrophenyl ether (NIT) on serum thyroid hormones in adult female mice. Toxicol Lett 15(2-3):231-235.

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.

Yamada-Okabe T, Sakai H, Kashima Y, Yamada-Okabe H. 2005. Modulation at a cellular level of the thyroid hormone receptor-mediated gene expression by 1,2,5,6,9,10-hexabromocyclododecane (HBCD), 4,4'-diiodobiphenyl (DIB), and nitrofen (NIP). Toxicol Lett 155(1):127-133, DOI:10.1016/j.toxlet.2004.09.005.

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