Nitrofen

Nitrofen is an herbicide of the diphenyl ether class. Because of concerns about its carcinogenicity, the use of nitrofen has been banned in the European Union^[2] and in the United States since 1996.^[1][3] It has been superseded by related protoporphyrinogen oxidase enzyme inhibitors including acifluorfen and fomesafen.

Nitrofen

Names
Preferred IUPAC name 2,4-Dichloro-1-(4-nitrophenoxy)benzene
Other names Nitrophen; Nitrofene; 2,4-Dichlorophenyl 4-nitrophenyl ether
Identifiers
CAS Number	1836-75-5 Y
3D model (JSmol)	Interactive image
ChemSpider	15010
ECHA InfoCard	100.015.824
PubChem CID	15787
UNII	N71UYG034A Y
CompTox Dashboard (EPA)	DTXSID7020970
InChI InChI=1S/C12H7Cl2NO3/c13-8-1-6-12(11(14)7-8)18-10-4-2-9(3-5-10)15(16)17/h1-7H Key: XITQUSLLOSKDTB-UHFFFAOYSA-N InChI=1/C12H7Cl2NO3/c13-8-1-6-12(11(14)7-8)18-10-4-2-9(3-5-10)15(16)17/h1-7H Key: XITQUSLLOSKDTB-UHFFFAOYAU
SMILES Clc2cc(Cl)ccc2Oc1ccc([N+]([O-])=O)cc1
Properties[1]
Chemical formula	C12H7Cl2NO3
Molar mass	284.09 g·mol−1
Appearance	Colorless, crystalline solid
Density	1.80 g/cm3 at 83 °C
Melting point	64–71 °C (147–160 °F; 337–344 K) (technical)
Solubility in water	0.7-1.2 mg/L at 22 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

In 2002, Nitrofen was detected in organic feed, organic eggs, and organic poultry products in Germany prompting a scandal which caused a decline in all organic meat sales in Europe.^[4][5]

Nitrofen is an IARC Group 2B carcinogen, meaning it is "possibly carcinogenic to humans".^[6]

Microörganisms in sewage cometabolise nitrofen, trifluralin, fluchloralin and profluralin; i.e. enzymes from other active metabolic processes also break up these chemicals. Over 88 days, nitrofen levels reduced by 40% under aerobic conditions.^[7]

"Tok" was a commercial herbicide of nitrofen.^[7]