Nitrofen

Names
Preferred IUPAC name

2,4-Dichloro-1-(4-nitrophenoxy)benzene

Other names

Nitrophen; Nitrofene; 2,4-Dichlorophenyl 4-nitrophenyl ether

Identifiers

CAS Number

* 1836-75-5 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 15010

ECHA InfoCard | 100.015.824

PubChem CID

* 15787

UNII |

* N71UYG034A Y

CompTox Dashboard (EPA)

* DTXSID7020970

InChI

* 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

SMILES

* Clc2cc(Cl)ccc2Oc1ccc([N+]([O-])=O)cc1

Properties[1]

Chemical formula

| 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)

Solubility in water

| 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

Chemical compound

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the use of nitrofen has been banned in the European Union[2] and in the United States since 1996.[1][3] It has been superseded by related protoporphyrinogen oxidase enzyme inhibitors including acifluorfen and fomesafen.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

[edit]

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
7. ^ a b 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

[edit]

* Nitrofen in the Pesticide Properties DataBase (PPDB)

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Pest control: herbicides

Anilides/anilines|

* acetochlor
* alachlor
* asulam
* benfluralin
* butachlor
* diethatyl
* diflufenican
* dimethenamid
* flamprop
* metazachlor
* metolachlor
* oryzalin
* pendimethalin
* pretilachlor
* propachlor
* propanil
* trifluralin

Aromatic acids|

* aminopyralid
* chloramben
* clopyralid
* dicamba
* picloram
* pyrithiobac
* quinclorac
* quinmerac

Arsenicals|

* cacodylic acid
* copper arsenate
* DSMA
* MSMA

HPPD inhbitors|

* flurochloridone
* isoxaflutole
* leptospermone
* mesotrione
* nitisinone
* sethoxydim
* sulcotrione

Nitriles|

* DCBN
* bromoxynil
* ioxynil

Organophosphorus|

* bensulide
* bialaphos
* ethephon
* fosamine
* glufosinate
* glyphosate
* piperophos

Phenoxy|

| Auxins|

* 2,4-D
* 2,4-DB
* dichlorprop
* fenoprop
* MCPA
* MCPB
* mecoprop
* 2,4,5-T

|

ACCase inhibitors|

| FOP herbicides|

* chlorazifop
* cyhalofop
* diclofop
* fenoxaprop
* fluazifop
* haloxyfop
* quizalofop

|

DIM herbicides|

* sethoxydim
* clethodim

Protox inhibitors|

| Nitrophenyl ethers|

* acifluorfen
* aclonifen
* bifenox
* fluorodifen
* fomesafen
* lactofen
* nitrofen
* oxyfluorfen

|

Pyrimidinediones|

* butafenacil
* saflufenacil

Triazolinones|

* carfentrazone
* sulfentrazone

Pyridines|

* dithiopyr
* fluroxypyr
* imazapyr
* thiazopyr
* triclopyr

Quaternary|

| Photosystem I inhibitors|

* cyperquat
* diquat
* paraquat

|

Thiocarbamates|

* Benthiocarb
* Butylate
* S-Ethyl dipropylthiocarbamate
* prosulfocarb

Triazines|

| cellulose biosynthesis inhibitors|

* indaziflam

|

Photosystem II inhibitors|

* ametryn
* atrazine
* cyanazine
* hexazinone
* metamitron
* metribuzin
* prometon
* prometryn
* propazine
* simazine
* simetryn
* terbuthylazine
* terbutryn

Ureas|

| Photosystem II inhibitors|

* chlortoluron
* DCMU
* difenoxuron
* isoproturon
* linuron
* monuron
* monolinuron
* tebuthiuron

|

ALS inhibitors|

* chlorsulfuron
* flazasulfuron
* metsulfuron-methyl
* sulfometuron methyl
* tribenuron

Others|

* 3-AT
* aminocyclopyrachlor
* Bentazon
* clomazone
* dinoseb
* dinoterb
* juglone
* methazole
* metam sodium
* pyribenzoxim

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