Article · Wikipedia archive · Last revised Jun 15, 2026

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 and in the United States since 1996. It has been superseded by related protoporphyrinogen oxidase enzyme inhibitors including acifluorfen and fomesafen.

Last revised
Jun 15, 2026
Read time
≈ 2 min
Length
349 w
Citations
9
Source
Wikipedia ↗
Nitrofen
source ↗
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
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
Properties1
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the use of nitrofen has been banned in the European Union2 and in the United States since 1996.13 It has been superseded by related protoporphyrinogen oxidase enzyme inhibitors including acifluorfen and fomesafen.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.45

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

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.7

"Tok" was a commercial herbicide of nitrofen.7

References

References

  1. Nitrofen data sheet, INCHEM WHO/FAO report, March 1999.
  2. Banned pesticide in German grain Archived 2016-03-04 at the Wayback Machine, 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" (PDF). Archived from the original (PDF) on 2011-10-25. Retrieved 2012-01-06.
  7. Jacobson, Stuart N.; O'Mara, Nancy L.; Alexander, Martin (November 1980). "Evidence for Cometabolism in Sewage". Applied and Environmental Microbiology. 40 (5): 917–921. doi:10.1128/aem.40.5.917-921.1980. PMC 291690.
External links
  • Nitrofen in the Pesticide Properties DataBase (PPDB)