{{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 = <ref name=inchem>[http://www.inchem.org/documents/icsc/icsc/eics0929.htm Nitrofen data sheet], INCHEM WHO/FAO report, March 1999.</ref> | C=12 | H=7 | Cl=2 | N=1 | O=3 | Appearance = Colorless, crystalline solid | Density = 1.80 g/cm<sup>3</sup> 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 = }} }}
'''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<ref>[http://www.pan-uk.org/pestnews/Issue/pn57/pn57p20a.htm Banned pesticide in German grain] {{Webarchive|url=https://web.archive.org/web/20160304033559/http://www.pan-uk.org/pestnews/Issue/pn57/pn57p20a.htm |date=2016-03-04 }}, Pesticides News No. 57, September 2002, page 22</ref> and in the United States since 1996.<ref name=inchem /><ref name=PPDB>{{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}}</ref> It has been superseded by related protoporphyrinogen oxidase enzyme inhibitors including acifluorfen and fomesafen.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.<ref>[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.</ref><ref>[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.</ref>
Nitrofen is an IARC Group 2B carcinogen, meaning it is "possibly carcinogenic to humans".<ref>{{Cite web |url=http://monographs.iarc.fr/ENG/Classification/ClassificationsGroupOrder.pdf |title=IARC Monographs - Classifications - by Group |access-date=2012-01-06 |archive-date=2011-10-25 |archive-url=https://web.archive.org/web/20111025122327/http://monographs.iarc.fr/ENG/Classification/ClassificationsGroupOrder.pdf |url-status=dead }}</ref>
Microorganisms 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.<ref name = "sewage"/>
"Tok" was a commercial herbicide of nitrofen.<ref name = "sewage">{{cite journal |last1=Jacobson |first1=Stuart N. |last2=O'Mara |first2=Nancy L. |last3=Alexander |first3=Martin |title=Evidence for Cometabolism in Sewage |journal=Applied and Environmental Microbiology |date=November 1980 |volume=40 |issue=5 |pages=917–921 |doi=10.1128/aem.40.5.917-921.1980|pmc=291690 }}</ref>
==References== {{reflist}}
==External links == * {{PPDB|1422}}
{{herbicides}}
Category:Herbicides Category:Phenol ethers Category:4-Nitrophenyl compounds Category:Chloroarenes Category:IARC Group 2B carcinogens Category:Group 14 herbicides