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).

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 [1] [3] It has been superseded by related protoporphyrinogen oxidase enzyme inhibitors including acifluorfen and fomesafen.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 an IARC Group 2B carcinogen, meaning it is "possibly carcinogenic to humans". [6]

Microörganisms 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

  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
  7. 1 2 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 .


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