Nitrofen

Last updated
Nitrofen
Nitrofen.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
AppearanceColorless, 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).
Infobox references

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 [1] [3] It has been superseded by related protoporphyrinogen oxidase enzyme inhibitors including acifluorfen and fomesafen.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]

Related Research Articles

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Aclonifen is a diphenyl ether herbicide which has been used in agriculture since the 1980s. Its mode of action has been uncertain, with evidence suggesting it might interfere with carotenoid biosynthesis or inhibit the enzyme protoporphyrinogen oxidase (PPO). Both mechanisms could result in the observed whole-plant effect of bleaching and the compound includes chemical features that are known to result in PPO effects, as seen with acifluorfen, for example. In 2020, further research revealed that aclonifen has a different and novel mode of action, targeting solanesyl diphosphate synthase which would also cause bleaching.

References

  1. 1 2 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