nitrofen

{{Chembox

| ImageFile = Nitrofen.svg

| ImageSize = 200px

| PIN = 2,4-Dichloro-1-(4-nitrophenoxy)benzene

| OtherNames = Nitrophen; Nitrofene; 2,4-Dichlorophenyl 4-nitrophenyl ether

|Section1={{Chembox Identifiers

| CASNo = 1836-75-5

| CASNo_Ref = {{cascite|correct|}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = N71UYG034A

| PubChem = 15787

| ChemSpiderID = 15010

| SMILES = Clc2cc(Cl)ccc2Oc1ccc([N+]([O-])=O)cc1

| 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

| InChIKey = XITQUSLLOSKDTB-UHFFFAOYAU

| StdInChI = 1S/C12H7Cl2NO3/c13-8-1-6-12(11(14)7-8)18-10-4-2-9(3-5-10)15(16)17/h1-7H

| StdInChIKey = XITQUSLLOSKDTB-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Properties_ref = [http://www.inchem.org/documents/icsc/icsc/eics0929.htm Nitrofen data sheet], INCHEM WHO/FAO report, March 1999.

| C=12 | H=7 | Cl=2 | N=1 | O=3

| Appearance = Colorless, crystalline solid

| Density = 1.80 g/cm³ at 83 °C

| MeltingPtC = 64-71

| MeltingPt_notes = (technical)

| BoilingPt =

| Solubility = 0.7-1.2 mg/L at 22 °C

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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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[http://www.pan-uk.org/pestnews/Issue/pn57/pn57p20a.htm Banned pesticide in German grain], Pesticides News No. 57, September 2002, page 22 and in the United States since 1996.{{cite web |url=http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1422.htm |title=Nitrofen |publisher=University of Hertfordshire |author=Pesticide Properties Database |access-date=2021-03-03}} It has been superseded by related protoporphyrinogen oxidase enzyme inhibitors including acifluorfen and fomesafen.

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.[http://www.just-food.com/news/nitrofen-scandal-causes-organic-meat-sales-to-dip_id69439.aspx Nitrofen scandal causes organic meat sales to dip], Just Food, October 2, 2002.[https://www.theguardian.com/world/2002/jun/12/medicalscience.bse Organic scandal halts Germany's green revolution], by John Hooper, The Guardian, June 12, 2002.

Nitrofen is listed as an IARC Group 2B carcinogen, meaning it is "possibly carcinogenic to humans".[http://monographs.iarc.fr/ENG/Classification/ClassificationsGroupOrder.pdf IARC Monographs - Classifications - by Group]