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| Product Name: | EPN | | Synonyms: | ENTl7798;Benzenephosphonic acid, thiono-, ethyl-(p-nitrophenyl) ester;benzenephosphothionicacid,ethyl-4-nitrophenylester;ENT 17,798;EPN Solution, 100ppm;Phenol, p-nitro-, O-ester with O-ethyl phenyl phosphonothioate;Phenylphosphonothioate, O-ethyl-O-p-nitrophenyl-;Phenylphosphonothioic acid O-ethyl O-p-nitrophenyl ester | | CAS: | 2104-64-5 | | MF: | C14H14NO4PS | | MW: | 323.3 | | EINECS: | 218-276-8 | | Product Categories: | | | Mol File: | 2104-64-5.mol |  |
| Melting point | 36℃ | | Boiling point | 371.1°C (estimate) | | density | 1.3 g/cm3 | | vapor pressure | 3,000 at 100 °C (quoted, Verschueren, 1983) | | refractive index | 1.6021 (589.3 nm 25℃) | | Fp | 2 °C | | storage temp. | APPROX 4°C
| | solubility | Miscible with acetone, benzene, methanol, isopropanol, toluene, and xylene (Windholz et al.,
1983) | | Water Solubility | 6.6 mg l-1 (20 °C, est.) | | form | solid | | Merck | 13,3656 | | BRN | 2542580 | | Exposure limits | NIOSH REL: TWA 0.5 mg/m3, IDLH 5 mg/m3; OSHA PEL: TWA 0.5
mg/m3; ACGIH TLV: TWA 0.5 mg/m3. | | EPA Substance Registry System | O-Ethyl O-(p-nitrophenyl) phenylphosphonothioate (2104-64-5) |
| Chemical Properties | Light-yellow crystals. Insoluble in water; soluble in most organic
solvents. Decomposes in alkaline solutions. | | Chemical Properties | EPN is a light yellow crystalline solid with an
aromatic odor (as a pesticide) or a brown liquid above 36°C | | Physical properties | Yellow to brown crystalline powder with an aromatic-like odor. | | Uses | EPN is used to control chewing insects, especially lepidopterous
larvae in cotton, rice, fruit and vegetables. | | Uses | Insecticide; acaricide. | | Uses | Acaricide; insecticide | | Definition | ChEBI: EPN is an organic phosphonate, a phosphonic ester and an organothiophosphate insecticide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide and an agrochemical. | | General Description | Light yellow crystalline powder with an aromatic odor. Used as an insecticide for cotton and an acaricide. | | Air & Water Reactions | Insoluble in water. Hydrolyzed by alkali [EPA, 1998]. | | Reactivity Profile | Organophosphates, such as EPN, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. | | Hazard | A cholinesterase inhibitor, absorbed by
skin, use may be restricted. Questionable carcinogen. | | Health Hazard | EPN may be fatal if swallowed. It is poisonous if inhaled and extremely hazardous by skin contact. Repeated exposure may, without symptoms, be increasingly hazardous. The estimated fatal oral dose is 0.3 grams for a 150 lb. (70 kg) person. | | Fire Hazard | (Non-Specific -- Organophosphorus Pesticide, n.o.s.) EPN may burn but does not ignite readily. Container may explode in heat of fire. Fire and runoff from fire control water may produce irritating or poisonous gases. Avoid strong oxidizers. Hydrolyzed by alkali. | | Agricultural Uses | Insecticide: Banned for use in the EU. All registered uses of EPN
in the U.S. were canceled by the U.S. EPA on August 31,
1988. Effective June 9, 1993, the U.S. EPA announced the
revocation of all tolerances for residues of the insecticide | | Trade name | NIAGARA®[C]; PIN®; SANTOX®;
TRIPLE KILL T®[C]; VETO®[C]
| | Safety Profile | Poison by ingestion,
skin contact, and intraperitoneal routes. An
experimental teratogen. A cholinesterase
inhibitor. Ths material is extremelyhazardous on contact with skin, inhalation,
or ingestion. A highly toxic insecticide.
When heated to decomposition it emits
highly toxic fumes of SOx, POx, NOx, and
phosphme. See also PARATHION, NITRO
COMPOUNDS OF AROMATIC
HYDROCARBONS, PHOSPHINE, and
SULFIDES | | Potential Exposure | EPN is used in preparation of emulsifiable, granular or wettable powder insecticides for cotton.
A potential danger to those involved in the manufacture,
formulation and application of this material. | | Environmental Fate | Biological. From the first-order biotic and abiotic rate constants of EPN in estuarine
water and sediment/water systems, the estimated biodegradation half-lives were 6.2 and
9.2 days, respectively (Walker et al., 1988).
Soil. Though no products were reported, the half-life in soil is 15–30 days (Hartley
and Kidd, 1987).
Photolytic. EPN may undergo direct photolysis since the insecticide showed some
absorption when a 1,4-dioxane was irradiated with UV light (l >290 nm) (Gore et al.,
1971).
Chemical/Physical. On heating, EPN is converted to the S-ethyl isomer (Worthing and
Hance, 1991). Releases toxic fumes of phosphorus, nitrogen and sulfur oxides when heated
to decomposition (Sax and Lewis, 1987; Lewis, 1990). Rapidly hydrolyzed in alkaline
solutions to p-nitrophenol, alcohol and benzene thiophosphoric acid (Sittig, 1985). | | Metabolic pathway | EPN is degraded and deactivated in soil, plants and animals by a series
of hydrolytic, dealkylation and oxidative desulfuration steps, ultimately
to give phenylphosphonate. The metabolic pathway may or may not
proceed via activation to the oxon, which is not usually detected in
appreciable quantities as it metabolically unstable. A detoxification reaction
via reduction of the nitro group to afford amino-EPN has been shown
to take place in anaerobic soil, bacteria and animals. Uncommonly for
organophosphates, hydroxylation of the phenyl ring also occurs in rats
and hens. | | Shipping | UN2783 Organophosphorus pesticides, solid,
toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1;
Labels: 6.1-Poisonous materials, Technical Name Required.
UN3018 Organophosphorus pesticides, liquid, toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials. | | Degradation | EPN is hydrolysed by alkali to yield 4-nitrophenol (2). The half-lives at
pH values 4 and 7 were 70 days and 22 days, respectively. When heated in
a sealed tube it was converted to the isomeric S-ethyl O-4-nitrophenyl
phenylphosphonothioate (3) (PM). | | Incompatibilities | Contact with oxidizers may cause the
release of phosphorous oxides. Contact with strong reducing agents, such as hydrides; may cause the formation of
flammable and toxic phosphine gas. Contact with alkalies
causes decomposition (hydrolysis) producing p-nitrophenol. | | Waste Disposal | EPN plant wastes are treated
by preaeration, activated sludge treatment; recycle, chlorination and final polishing where additional natural biological stabilization occurs. EPN is also relatively rapidly
hydrolyzed in alkaline solution to benzene thiophosphoric
acid; alcohol and p-nitrophenol and soil burial with alkali
may be used. For large quantities, however, incineration is
recommended. 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.
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| | EPN Preparation Products And Raw materials |
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