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Nitrofen

Nitrofen
Names
Preferred IUPAC name
2,4-Dichloro-1-(4-nitrophenoxy)benzene
Other names
Nitrophen; Nitrofene; 2,4-Dichlorophenyl 4-nitrophenyl ether
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.824 Edit this at Wikidata
UNII
  • 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
  • Clc2cc(Cl)ccc2Oc1ccc([N+]([O-])=O)cc1
Properties[1]
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)
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).

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the use of nitrofen has been banned in the European Union[2] and in the United States since 1996.[1][3] It has been superseded by related protoporphyrinogen oxidase enzyme inhibitors including acifluorfen and fomesafen.

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

References

  1. ^ a b Nitrofen data sheet, INCHEM WHO/FAO report, March 1999.
  2. ^ Banned pesticide in German grain, Pesticides News No. 57, September 2002, page 22
  3. ^ Pesticide Properties Database. "Nitrofen". University of Hertfordshire. Retrieved 2021-03-03.
  4. ^ Nitrofen scandal causes organic meat sales to dip, Just Food, October 2, 2002.
  5. ^ Organic scandal halts Germany's green revolution, by John Hooper, The Guardian, June 12, 2002.
  6. ^ IARC Monographs - Classifications - by Group
  • Nitrofen in the Pesticide Properties DataBase (PPDB)
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