Nitrofen is a crystalline solid.
ChEBI: Nitrofen is an organic molecular entity. It has a role as an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor and a herbicide.
Colorless crystals or black solid. Used as a pre- or post-emergence herbicide.
NITROFEN is a nitrated and halogenated ether derivative.
Nitrofen is moderately toxic by ingestionand inhalation of dusts. The lethal doses in cats from oral administration and inhalationof dusts are 300 mg/kg and 620 mg/m3/4h,respectively (NIOSH 1986). Bovine calvestreatedorally by 1.5 mL 25% nitrofen/kg produced toxic effects after 36–48 hours. Thesymptoms were increase in body temperature, depression, and progressive decrease inrespiration rate and pulse rate,similar to tribulin (Gupta and Singh 1985). An increase inthe activities of serum glutamic-oxaloacetictransaminase and glutamipyruvictransaminase was noted(Gupta and Singh 1984). Nitrofen has beenfound to cause cancer in animals. There issufficient evidence of its carcinogenicity inanimals (IARC). Oral administration in micecaused liver and lung cancers.
Flash point data for NITROFEN are not available; however, NITROFEN is probably combustible.
Confirmed carcinogen
with experimental carcinogenic data. Poison
by ingestion. Moderately toxic by inhalation
and possibly other routes. Experimental
teratogenic and reproductive effects. A skin
and severe eye irritant. Mutation data
reported. A broad-spectrum herbicide. See
also NITRO COMPOUNDS of
AROMATIC HYDROCARBONS and
ETHERS. When heated to decomposition it
emits very toxic fumes of Cl and NOx.
GENERAL METHOD: A dispersion of 0.69 g (17.3 mmol) of 60% NaH in mineral oil was washed with hexane and subsequently suspended in 20 mL of DMF. A solution of 2,4-dichlorophenol (12.9 mmol) in DMF (20 mL) was added slowly and dropwise. After stirring for 1 hour at room temperature, a DMF (4 mL) solution of p-fluoronitrobenzene (1.5 g, 10.3 mmol) was added. Stirring was continued at room temperature for 1 h. The reaction mixture was then warmed up to 50 °C and maintained for 12 h. The reaction mixture was then heated up to 50 °C. Upon completion of the reaction, the reaction was quenched with saturated NH4Cl solution. The mixture was extracted with ether and the organic layer was washed sequentially with 0.2 M NaOH solution until the aqueous layer was colorless, then with 1 M HCl and saturated brine solution. The organic layer was dried over anhydrous MgSO4, concentrated in vacuum and finally purified by column chromatography using hexane-ethyl acetate (5:1) as eluent to afford the target product 2',4'-dichloro-4-nitro-diphenyl ether.
Nitrofen is a contact herbicide used
for pre-and post-emergency control of annual grasses and
broadleaf weeds on a variety of food and ornamental crops.
Occupational exposure to nitrofen, primarily through
inhalation and dermal contact may occur among workers
at production facilities. Field handlers of the herbicide
are subject to inhalation exposure during application
procedures.
Nitrofen is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
UN3345 Phenoxyacetic acid derivative pesticide,
solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
UN3077 Environmentally hazardous substances, solid,
n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous
material, Technical Name Required.
Small quantities may be landfilled
but large quantities should be incinerated. In
accordance with 40CFR165, follow recommendations for
the disposal of pesticides and pesticide containers. Must be
disposed properly by following package label directions or
by contacting your local or federal environmental control
agency, or by contacting your regional EPA office.
[1] Canadian Journal of Chemistry, 2015, vol. 94, # 1, p. 95 - 104
[2] European Journal of Organic Chemistry, 2011, # 8, p. 1587 - 1592
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 7, p. 1588 - 1592
[4] New Journal of Chemistry, 2015, vol. 39, # 9, p. 7281 - 7292
[5] European Journal of Medicinal Chemistry, 2016, vol. 113, p. 273 - 292
