Chemical Properties
solid
Uses
Formerly as herbicide.
General Description
Colorless crystals or black solid. Used as a pre- or post-emergence herbicide.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
NITROFEN is a nitrated and halogenated ether derivative.
Fire Hazard
Flash point data for NITROFEN are not available; however, NITROFEN is probably combustible.
Potential Exposure
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.
First aid
Skin Contact: Flood all areas of body that have
contacted the substance with water. Don’t wait to remove
contaminated clothing; do it under the water stream. Use
soap to help assure removal. Isolate contaminated clothing
when removed to prevent contact by others. Eye
Contact: Remove any contact lenses at once. Immediately
flush eyes well with copious quantities of water or normal
saline for at least 20 30 minutes. Seek medical attention.
Inhalation: Leave contaminated area immediately; breathe
fresh air. Proper respiratory protection must be supplied to
any rescuers. If coughing, difficult breathing or any other
symptoms develop, seek medical attention at once, even if
symptoms develop many hours after exposure. Ingestion:
Contact a physician, hospital or poison center at once. If
the victim is unconscious or convulsing, do not induce
vomiting or give anything by mouth. Assure that the
patient’s airway is open and lay him on his side with his
head lower that his body and transport immediately to a
medical facility. If conscious and not convulsing, give a
glass of water to dilute the substance. Vomiting should not
be induced without a physician’s advice.
Shipping
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.
Waste Disposal
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.
Definition
ChEBI: Nitrofen is an organic molecular entity. It has a role as an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor and a herbicide.
Health Hazard
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.
Mechanism of action
Contact action, inhibits noncyclic electron transport distrupting photosynthesis
Synthesis
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.
Carcinogenicity
Nitrofen is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
References
[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
