フェニルチオホスホン酸O-エチルO-(p-ニトロフェニル)

(Non-Specific -- Organophosphorus Pesticide, n.o.s.) Stay upwind; keep out of low areas. Move containers from fire area if you can do it without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material. Wear positive pressure breathing apparatus and special protective clothing.

Use powder, alcohol-resistant foam, water spray, carbon dioxide.

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer immediately for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention. Wear protective gloves when administering first aid. Put clothes in sealable container.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer immediately for medical attention.

Warning: Extremely hazardous by skin contact. Effects may be delayed up to 12 hours. Caution is advised.

(General first aid procedures)

Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]

0.5 [mg/m3], inhalable fraction[German Research Foundation (DFG)]

Self contained breathing apparatus with a full facepiece operated in pressure demand, or other positive pressure mode /should be used in firefighting/. /Parathion/

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic/

If material on fire or involved in fire: Use water in flooding quantities as fog. Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) /Organophosphorus pesticides, solid, toxic/

1) Ventilate area of spill. 2) Cover with soda ash, mix and spray with water. Place in container of water and allow to stand for two days, then neutralize with 6 molar hydrogen chloride.

Do NOT wash away into sewer. Sweep spilled substance into containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place. Chemical protection suit including self-contained breathing apparatus.

An explosion damaged the EPN section of manufacturing plant. Unknown quantities were flushed (due to firefighting) into a drainage ditch, sanitary sewer, and waste treatment plant. At water treatment plant, initial EPN level (5.8 mg/l) was reduced to zero following treatment with sodium hydroxide and about 2 wk of aeration. Sodium hydroxide was applied at various locations in the drainage ditch until pH was raised to about 11.0. After treatment, affected water was pumped into abandoned gypsum lagoon system.

Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/

For more Cleanup Methods (Complete) data for EPN (6 total), please visit the HSDB record page.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Hydrolysis: Treat EPN with alkali... . Peer-review: Large amount, incinerate in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics, and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

For more Preventive Measures (Complete) data for EPN (11 total), please visit the HSDB record page.

... Hens treated concurrently with EPN, n-hexane and methyl isobutyl ketone. Methyl isobutyl ketone alone or in combination with O-ethyl O-nitrophenyl phenylphosphonothioate and n-hexane induced liver microsomal cytochrome p450 content and phoenobarbital inducible cytochrome p450 enzyme activities. Microsomes from hens treated with EPN, n-hexane, methyl isobutyl ketone or mixtures of EPN, n-hexane and methyl isobutyl ketone significantly enhanced the biotransformation of EPN to the more neurotoxic oxidation metabolite EPN. The results indicate that increased neurotoxicity after concurrent exposure to EPN, n-hexane and methyl isobutyl ketone is related to methyl isobutyl ketone induction of phenobarbital inducible cytochrome p-450 isozymes and the subsequent metabolic activation of EPN.

The anticholinesterase action of parathion and EPN was significantly potentiated by carbon disulfide /in ddY mice/, while that of dimethoate and diazinon was significantly reduced. Carbon disulfide had no significant effect or was slightly suppressive on the action of the other organophosphorus cmpd. In an in vitro experiment, liver microsomes isolated 1 hour after carbon disulfide were incubated with parathion or EPN. Effects on detoxication and activation of parathion and EPN by liver microsomes were evaluated by determining the degree of p-nitrophenol production and extent of cholinesterase inhibition, respectively. Liver microsomal detoxification and activation of parathion and EPN were decreased by carbon disulfide. The authors suggest that the diverse effects of carbon disulfide on the toxicity of various organophosphorus insecticides may reflect quantitative and qualitative differences in the metabolism of each cmpd.

...In vivo studies with rat and dog showed that EPN affects metabolism /of malathion/ by inducing change from carboxy ester hydrolysis to phosphate hydrolysis.

Nervous

Eyes, skin, respiratory system, cardiovascular system, central nervous system, blood cholinesterase

LD50 ANAS PLATYRHYNCHOS (MALLARD DUCK) ORAL 3.08 MG/KG (95% CONFIDENCE LIMIT 2.38-4.00), 3 MO OLD FEMALES /SAMPLE PURITY = 91%/

LD50 PHEASANT ORAL 53.4 MG/KG (95% CONFIDENCE LIMIT 38.5-74.1), 3-5 MO OLD FEMALES /SAMPLE PURITY = 91%/

LD50 ALECTORIS CHUKAR (CHUKAR) ORAL 14.3 MG/KG (95% CONFIDENCE LIMIT 10.3-19.8), 3 MO OLD FEMALES /SAMPLE PURITY = 91%/

LD50 COTURNIX ORAL 5.25 MG/KG (95% CONFIDENCE LIMIT 3.79-7.28), 2 MO OLD FEMALES

For more Ecotoxicity Values (Complete) data for EPN (25 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), a mean Koc value of 1,327(2), indicates that EPN is expected to have low mobility in soil(SRC). Volatilization of EPN from moist soil surfaces is not expected to be an important fate process(SRC), given a Henry's Law constant of 4.44X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 9.5X10-7 mm Hg(3), and water solubility, 3.11 mg/l(4). EPN is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). The half-life of 14C-labeled EPN in field tests with Dundee silt loam (pH 5.5, organic matter 1.3%) and Keyport silt loam (pH 6.4, organic matter 2.75%) were 2 weeks and 1 month, respectively(5) Greater than 90% of the residual radiolabeled carbon was found in the top 3 inches of soil, after 18 months, indicating no leaching of EPN or its degradation products had occurred(5). Under greenhouse conditions 14C-labeled EPN has a half-life of 5-6 weeks in Fallsington sandy loam soil (pH 5.6, organic matter 1.4%)(5). In a biometer study with Keyport silt loam half-lives were 5 and 6 weeks at 2 and 10 ppm, respectively(5). Breakdown of EPN in soil proceeded primarily through hydrolysis and oxidation to phenylphosphonic acid, followed by further degradation of the phenyl ring to CO2(5). Under laboratory conditions, the half-lives of 1 ppm EPN in upland soils were 30-90 days and in submerged soils, 3-15 days(6). In upland soils degradation products were EPN-oxon, desethyl EPN-oxon, O-ethyl S-methylphenylphosphonothiolate, p-nitrophenol, O-ethyl O-methylphenylphosphonate, O-ethylphenylphosphonate, and phenylphosphonic acid(6).

AQUATIC FATE: Based on a classification scheme(1), a mean Koc value of 1,327(2), indicates that EPN is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 4.44X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 9.7X10-7 mm Hg(4) and water solubility, 3.11 mg/l(5). According to a classification scheme(6), BCF values of 358(7) to 7,700(8) in fish suggest the potential for bioconcentration in aquatic organisms is high to very high(SRC); however, EPN is rapidly depurated(9). Based on results of persistence studies done on EPN in soil(10,11), EPN is expected to degrade primarily through hydrolysis and oxidation to phenylphosphonic acid(SRC). Photodegradation half-lives for EPN in aqueous solution without humic acids, containing humic acids, containing humic acids from soil and containing humic acid sodium salt were 38.5, 28.9, 34.6, and 49.5 days, respectively; EPN at 10-15 ppm plus humic acids at 5 ppm were irradiated in Pyrex-glass vessels with artificial sunlight(12). Half-lives for EPN in water are 70 days (pH 4); 22 days (pH 7); 3.5 days (alkaline)(13).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), EPN, which has a vapor pressure of 9.5X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase EPN is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5.1 hours(SRC), calculated from its rate constant of 7.5X10-11 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). Particulate-phase EPN may be removed from the air by wet and dry deposition(SRC). EPN in p-dioxane exhibits slight absorption of UV light in the environmentally relevant range (>290 nm)(4), suggesting that EPN may be susceptible to direct photolysis by sunlight(SRC).

EPN was identified during the 1975 FDA Total Diet Study in large fruit, nuts, and infant and junior foods(1). The FDA's Total Diet Study in 1970-76 reported 1.4% of 148 peanut samples contained detectable residues of EPN; EPN concentrations ranged from 0.11-0.5 ppm(1). In a review of the chemicals reported in the FDA's Revised Market Basket Study from 1982 to 1991, representing 37 market baskets each containing 234 food items that represented about 5000 food types, EPN was reported 3 times in 2 foods at an average concentration of 0.005 ug/g(2). Only 1 of 13,980 and 0 of 13,085 samples of foods collected and analyzed in 10 state food laboratories in 1988 and 1989, respectively, contained detectable levels of EPN(3). The FDA's pesticide residue monitoring program in fiscal year 1988/1989 monitored 18,798 samples of domestically-produced food and imported food from 88 countries; EPN was identified although concentrations and percent positive detects were not reported(4). The FDA's pesticide residue monitoring program in fiscal year 1989/1990 monitored 19,962 samples of domestically-produced food and imported food from 92 countries; EPN was identified although concentrations and percent positive detects were not reported(5). 3 of 457 domestic samples of mixed feed rations collected by the FDA for pesticide surveillance during fiscal years 1989 to 1994 contained EPN; concentrations ranged from trace amounts to 0.030 ppm(6).

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

/BIRDS and MAMMALS/ .../Symptoms appearing in mallards, pheasants, chukars, coturnix, pigeons, and house sparrows from acute oral LD50 dose were/ ataxia, prostration, salivation, lacrimation, tenesmus, diarrhea, dyspnea, tremors, wings thrust at right angles to body axis, tetany, terminal wing-beat convulsions, or opisthotonos.

/BIRDS and MAMMALS/ Injection of duck eggs ...causes deformity of feet of ducklings.

/AQUATIC SPECIES/ EPN was acutely toxic to crustaceans and fish, with commercial pink shrimp being most sensitive species tested. In chronic toxicity studies using M. bahia, significant mortality and fewer young were produced at EPN exposure level of 4.13 ug/L.

/OTHER TERRESTRIAL SPECIES/ Toxic to bees.

/PLANTS/ Non-phytotoxic except to some varieties of apple.

Dizziness. Pupillary constriction. Muscle cramps. Excessive salivation. Sweating. Muscle twitching. Nausea.

MAY BE ABSORBED! Redness. Pain. Further see Inhalation.

Redness. Blurred vision.

Nausea. Abdominal cramps. Vomiting. Diarrhoea. Drowsiness. Further see Inhalation.

irritation eyes, skin; miosis, lacrimation (discharge of tears); rhinorrhea (discharge of thin nasal mucus); headache; chest tightness, wheezing, laryngeal spasm; salivation; cyanosis; anorexia, nausea, abdominal cramps, diarrhea; paralysis, convulsions; low blood pressure, cardiac irreg

The substance is very toxic to aquatic organisms. Bioaccumulation of this chemical may occur in fish. The substance may cause long-term effects in the aquatic environment. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. EPN is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0147; Pesticide type: Insecticide (Acaricide); Registration Standard Date: 04/15/87; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): o-ethyl o-(p-nitrophenyl) phenylphosphonothioate; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. EPN is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered for and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

No ACTIVE registrants found for selected chemical. [NPIRS] Use as mosquito larvicide cancelled in 1983; All registrations voluntarily cancelled in 1987; [EPA: Status of Chemicals in Special Review]

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

For EPN (USEPA/OPP Pesticide Code: 041801) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Insecticide for cotton /Former use/

Non-systemic insecticide and acaricide /Former use/

For more Uses (Complete) data for EPN (8 total), please visit the HSDB record page.

(1974) 7.99X10+7 G

(1978) 9.26X10+8 G (PRINCPL CUSTMS DISTS)

(1975) 9.08X10+7 G (CONSUMPTION)

(1978) 4.99X10+9 G (CONSUMPTION)

Phosphenyl chloride + ethanol + p-nitrophenol + sulfur (dehydrochlorination/dehydrochlorination/thionation)

...Reaction of phenylphosphonothioic dichloride with ethanol in presence of pyridine in benzene at room temp, followed by reaction with sodium 4-nitrophenoxide in boiling chlorobenzene ... .

USEPA/OPP Pesticide Code 041801; Trade Names: PIN, Santox.

EPN is available as a 45% emulsifiable concentrate, as granules, and in combination with other insecticides.

Emulsifiable concentrate (450 or 480 g ai/l), granules (40 g/kg), dustable powder (15 g/kg). Mixtures include: 'Kasutop Dust', dustable powder (15 g EPN + 2 g kasugamycin/kg); 'Meidon 15 Dust', dustable powder (15 g EPN + 10 g carbaryl/kg); 'Tsumaphos', dustable powder (15 g EPN + 15 g metolcarb/kg); emulsifiable concentrate (300 g EPN + 300 g parathion-methyl/l).

Wettable powders and dusts

Mixtures: 'Veto' (+parathion-methyl)