2104-64-5 Usage
Description
O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate, commonly known as EPN, is a light yellow crystalline powder with an aromatic odor. It is a pesticide that was once widely used to control chewing insects, particularly lepidopterous larvae in cotton, rice, fruit, and vegetables. However, its use has been banned in the EU and all registered uses in the U.S. were canceled by the U.S. EPA on August 31, 1988. The chemical is a light-yellow crystalline solid that is insoluble in water but soluble in most organic solvents and decomposes in alkaline solutions.
Uses
Used in Agriculture:
O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate is used as an insecticide and acaricide for controlling chewing insects, especially lepidopterous larvae in cotton, rice, fruit, and vegetables. It was effective in protecting crops from these pests, but due to its potential environmental and health risks, its use has been restricted or banned in several regions.
Used in Chemical Industry:
O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate is used as a chemical intermediate in the synthesis of other compounds. Its specific applications in the chemical industry may vary, but it plays a role in the production of various products.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 2104-64-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,0 and 4 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 2104-64:
(6*2)+(5*1)+(4*0)+(3*4)+(2*6)+(1*4)=45
45 % 10 = 5
So 2104-64-5 is a valid CAS Registry Number.
InChI:InChI=1/C14H14NO4PS/c1-2-19-20(18,21)14-6-4-3-5-13(14)11-7-9-12(10-8-11)15(16)17/h3-10H,2H2,1H3,(H,18,21)/p-1
2104-64-5Relevant articles and documents
Concentrates of organophosphorous insecticides
-
, (2008/06/13)
A low volatile organic compound co-solvent system is disclosed for preparing emulsion concentrates of low melting organophosphorous insecticides wherein the bioefficacy of the insecticide active is significantly enhanced. The co-solvent system comprises a water-soluble ethoxylated fatty acid/rosin acid-nonionic surfactant composition.
Macrocyclic plant acaricides
-
, (2008/06/13)
Compounds of the formula I STR1 in which either R is methyl and there is a double bond in the 9,10-position, or in which R is hydrogen and there is a single bond in the 9,10-position, are highly active against Acarina which damage plants.
Insecticidal composition for agricultural and horticultural use
-
, (2008/06/13)
A synergistic insecticidal composition comprising a nitromethylene derivative of the formula STR1 in which X is a lower alkyl group, a lower alkoxy group or a halogen atom, n is 0, 1 or 2, and m is 2 or 3, and an insecticide which is a carboxylic acid ester, carbamate, organophosphate ester or one of a group of specific compounds.
