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Home > Encyclopedia > Azinphos-ethyl

Azinphos-ethyl

Azinphos-ethyl structure

Azinphos-ethyl 

structure
  • CAS No:

    2642-71-9

  • Formula:

    C12H16N3O3PS2

  • Chemical Name:

    Azinphos-ethyl

  • Synonyms:

    Phosphorodithioic acid,O,O-diethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] ester;Phosphorodithioic acid,O,O-diethyl ester,S-ester with 3-(mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one;1,2,3-Benzotriazine,phosphorodithioic acid deriv.;R 1513;Bayer 16259;O,O-Diethyl S-(4-oxo-3H-1,2,3-benzotriazine-3-methyl) phosphorodithioate;O,O-Diethyl S-(4-oxobenzotriazino-3-methyl) phosphorodithioate;O,O-Diethyl S-[4-oxo-1,2,3-benzotriazin-3(4H)-ylmethyl] phosphorodithioate;O,O-Diethyl phosphorodithioate S-ester with 3-(mercaptomethyl)-1,2,3-benzotriazin-4-(3H)-one;S-(3,4-Dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl) O,O-diethyl phosphorodithioate;Ethyl Guthion;Azinphos-ethyl;Gusathion A;Gusathion ethyl;Ethyl azinphos;S-(3,4-Dihydro-4-oxobenzo[d]-1,2,3-triazin-3-ylmethyl)diethyl phosphorothiolothionate;Guthion ethyl;Ethyl Gusathion;Gusathion H;Gusathion K;Cotnion-ethyl;Gusathion K forte;Azinphos A;Triazothion

  • Categories:

    Agrochemicals  >  Insecticides

Description

Azinphos-ethyl forms colorless, clear crystals. It is insoluble in water, but soluble in most organic solvents. As an acaricide, azinphos-ethyl is used for the control of pests, such as, spider mites, aphids, caterpillars, potato bug, beetles, bollweevils, whitefl ies, bollworms, thrips, and other biting and sucking insects. Human exposures to azinphos-ethyl occur through absorption from the gastrointestinal tract, through the intact skin, and by inhalation of fi ne spray mist and dusts.
A


Azinphos-ethyl appears as colorless crystals. Used as a non-systemic insecticide with good ovicidal properties and long persistence. Used on cotton, citrus, vegetables, potatoes, tobacco, rice, and cereals to control caterpillars, beetles, aphids, spiders and many other insects. Not registered for use in the U.S. (EPA, 1998)


Azinphos-ethyl appears as colorless crystals. Used as a non-systemic insecticide with good ovicidal properties and long persistence. Used on cotton, citrus, vegetables, potatoes, tobacco, rice, and cereals to control caterpillars, beetles, aphids, spiders and many other insects. Not registered for use in the U.S. (EPA, 1998)|Azinphos-ethyl is an organothiophosphate insecticide and an organic thiophosphate. It has a role as an acaricide, an EC 3.1.1.7 (acetylcholinesterase) inhibitor and an agrochemical. It derives from a hydride of a 1,2,3-benzotriazine.

Azinphos-ethyl Basic Attributes

345.38

345.38

220-147-6

EA96NYT5J5

2783

DTXSID5037498

Colorless needles|Needles

Characteristics

121

3.40

Solid

1.284 g/cm3 @ Temp: 20 °C

53 °C

111 °C @ Press: 1 x 10-3 Torr

222.7±31.5 °C

1.651

In water, 10.5 mg/L at 20 deg C

0-6°C

3.2 x 10 -4 Pa (20 °C)

Oral-rat LD50: 7 mg/kg

Open flame is flammable; heat releases toxic nitrogen oxide, sulfur oxide, phosphorus oxide gas

Henry's Law constant = 9.95X10-8 atm-cu m/mol at 20 °C (est)

175.58 Ų [M+Na]+

VOLATILITY 0.042 MG/CU M @ 20 °C|Reacts in alkali|Hydroxyl radical reaction rate constant = 1.85X10-10 cu cm/molec sec at 25 °C (est)

Nearly insoluble in water. What little amount is solubilized will readily hydrolyze.

Amides and Imides

The BPS Pesticide incident in Helena resulted in an explosion and death of three firemen. The burning of a 1,000 pound sack of Azinphos Methyl or the flashing of Maneb which was present on the facility may have caused the explosion. Azinphos Ethyl may behave similarly. At elevated temperatures, it will decompose generating toxic gases.

Non-corrosive

Safety Information

II

6.1(a)

2783

3

24-28-50/53

28-36/37-45-60-61

TD8400000

T+,N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Relatively stable in acidic media.

P273-P280-P301 + P310 + P330-P302 + P352 + P312-P391-P501

H300-H311-H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|Peer-review: This highly toxic material is rapidly hydrolyzed by cold alkali. Use 5 parts by volume 4% wt/vol sodium hydroxide soln to 1 volume of pesticide. Hydrolysis is improved by making the sodium hydroxide soln in 50% ethanol. Use much water to wash reaction mixture down to sewer. Large amt - incinerate in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))|Potential candidate for rotary kiln incineration, with a temperature range of 820 to 1,600 °C and a residence time of seconds. Also, a potential candidate for fluidized bed incineration, with a temperature range of 450 to 980 °C, and a residence time of seconds. Also, a potential candidate for liquid injection incineration with a temperature range of 650 to 1,600 °C, and a residence time of 0.1 to 2 seconds. /Parathion/|The following wastewater treatment technologies have been investigated for parathion: Reverse osmosis. /Parathion/

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.|Incompatible with alkaline materials.

Toxicology Review: Residue Reviews 51: 123 (1974)|Toxicology Review: Residue Reviews 63: 1 (1976)|WHO; Environ Health Criteria 63: Organophosphorus Insecticides: A General Introduction (1986)

(Non-Specific -- Organophosphorus Pesticide, n.o.s.) When heated to decomposition, it emits very toxic fumes of sulfur, phosphorus and nitrogen oxides. Container may explode in heat of fire. (EPA, 1998)

|Danger|H300: Fatal if swallowed [Danger Acute toxicity, oral]|P264, P270, P273, P280, P301+P310, P302+P352, P312, P321, P322, P330, P361, P363, P391, P405, and P501|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 201 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

(Non-Specific -- Organophosphorus Pesticide, n.o.s.) Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors. Small spills: absorb with sand or other noncombustible absorbent material and place into containers for later disposal. Small dry spills: with clean shovel place material into clean dry containers and cover; move containers from spill area. Large spills: dike far ahead of spill for later disposal. (EPA, 1998)

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)|Rubber gloves, gas mask or respirator, rubber boots, thick long-sleeved shirt/jacket, long pants.|NEOPRENE COATED GLOVES; RUBBER WORKSHOES OR OVERSHOES; LATEX RUBBER APRON; GOGGLES; RESPIRATOR OR MASK APPROVED FOR TOXIC DUSTS & ORGANIC VAPORS. /PARATHION/|Employees should be provided with and required to use impervious clothing, gloves, face shields (eight inch minimum), and other appropriate protective clothing necessary to prevent repeated, or prolonged skin contact with parathion. /Parathion/|Respiratory protection (supplied-air respirator with full facepiece or self-contained breathing apparatus) should be available where these compounds are manufactured or used and should be worn in case of emergency and overexposure. /Phosphorus compounds/|For more Personal Protective Equipment (PPE) (Complete) data for AZINPHOS ETHYL (6 total), please visit the HSDB record page.

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.) Use foam, dry chemical, or carbon dioxide. /Organophosphorus pesticides, solid, toxic/

1. Ventilate area of spill or leak. 2. Collect for reclamation, or absorb in vermiculite, dry sand, earth, or a similar material. /parathion/|Spills of parathion on floors ... absorbed with an absorbing clay. Sweeping compound ... facilitate the removal of all visible traces of parathion contaminated clay. /Parathion/|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/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/|Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/

A portion of even the most flammable materials is likely to be lost by vaporization. ... The smoke from an open fire used to destroy pesticides will contain some of the poison. Burning should be attempted only in an isolated place. Inhalation of smoke must be avoided. /Pesticides/|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.|... Keep away from heat and open flame.|Special aircraft should preferably be used for spraying or dusting toxic organophosphorus pesticides. ... Aerial spraying or dusting gives rise to clouds which spread over larger surfaces than clouds produced by ground application. Aerial spraying should therefore be carried out on windless days only. Residential areas, water supply sources, etc must be avoided. ... When aircraft approaches, signalmen /guiding the aircraft/ should leave the windward side. ... The local population should be informed about the site & time of aerial pesticide treatment. Access of unauthorized persons & especially children to the area to be treated must be ... forbidden. Warning signs should be placed at the limits of the area. Ground spraying must be carried out with compressed-air spraying equipment towed by tractors with closed cabs. /Organophosphorus pesticides/|For more Preventive Measures (Complete) data for AZINPHOS ETHYL (14 total), please visit the HSDB record page.

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|For more DOT Emergency Guidelines (Complete) data for AZINPHOS ETHYL (16 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.|Severe marine pollutant

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. Azinphos-ethyl 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 form 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 ... .

SEDIMENT: Azinphos-ethyl was not detected in sediment samples in the upper Great Lakes collected in the summer of 1974(1).

Toxicity

most toxic

Pretreatment with piperonyl butoxide (400 mg/kg) 1 hr prior to challenge potentiates the toxicity of ethyl guthion.|Some phenothiazines may antagonize & some may potentiate the toxic anticholinesterase effects of ... /organophosphorus insecticides/. /Organophosphate cholinesterase inhibitors/|In long term therapy, adrenocorticoids antagonize the antiglaucoma effects of anticholinesterases (incr ocular pressure). ... Anticholinergics antagonize the miotic (antiglaucoma) & other muscarinic effects of anticholinesterases on the autonomic & central nervous systems. Tricyclic antidepressants (anticholinergic effects) antagonize the antiglaucoma (miotic) effects of anticholinesterases in glaucoma. ... Antihistamines with anticholinergic effects antagonize the miotic (antiglaucoma) & CNS effects of anticholinesterases. Anticholinesterases potentiate tranquilizing & behavioral changes induced by antihistamines. The actions of anticholinesterase agents on autonomic effector cells, & to some extent those on CNS, are antagonized by atropine, an antidote of choice. Barbiturates are potentiated by anticholinesterases. ... Dexpanthenol potentiates the effects of anticholinesterases. Fluorophosphate insecticides potentiate the effects of other anticholinesterases. /Anticholinesterases/|Barbiturates are potentiated by anticholinesterases. Although barbiturates may be used cautiously in treating convulsions, extreme care is essential in handling poisonings due to anticholinesterases, particularly organophosphorus pesticides. Echothiophate, a cholinesterase inhibitor used as miotic, potentiates other such inhibitors... used for other purposes (additive effects) or possibly synergistic. Those exposed to organophosphate insecticides must take strict precautions. ...Organophosphorus insecticides: additive anticholinesterase effects. Hazardous. Patients on anticholinesterases (even topical, such as eye drops) should avoid areas where organophosphorus insecticides... recently... used. /Anticholinesterase/|For more Interactions (Complete) data for AZINPHOS ETHYL (8 total), please visit the HSDB record page.

LD50 Rat percutaneous about 500 mg/kg/24 hr|LD50 Rat inhalation 0.15 mg/L air/4 hr|LD50 Rat ip >7.5 mg/kg|LD50 Rat oral 7 mg/kg|For more Non-Human Toxicity Values (Complete) data for AZINPHOS ETHYL (8 total), please visit the HSDB record page.

Young persons under 18 yr, expectant or nursing mothers, /alcoholics/, or persons for whom work with toxic chemicals is contraindicated on account of their state of health /are at elevated risk from the toxic effects of organophosphorus pesticides. Those individuals with/ organic diseases of the CNS, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases and circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of the liver & kidneys, eye diseases (chronic conjunctivitis and keratitis) /are at elevated risk from exposure/. /Organophosphorus pesticides/|Those individuals who are exposed to organophosphorus pesticides with pre-existing/ organic diseases of the central nervous system, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases & circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of liver & kidneys, eye diseases (chronic conjunctivitis & keratitis) /are at elevated risk from exposure/. The blood cholinesterase activity must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed to organophosphorus pesticides until this activity is completely restored. Persons with initial signs of indisposition should cease work with pesticides. /Organophosphorus pesticides/

Azinphos ethyl's production may result in its release to the environment through various waste streams; its use as an insecticide(1) will result in its direct release to the environment(SRC). Due to its high toxicity, it is no longer produced or used in the US or Canada(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a structure estimation method(2), indicates that azinphos ethyl is expected to have moderate mobility in soil(SRC). Volatilization of azinphos ethyl from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.9X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 2.4X10-6 mm Hg(3), and water solubility, 10.5 mg/L(4). Azinphos ethyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Degradation of organophosphorothioate pesticides by photooxidation under ultraviolet or sunlight radiation at the soil surface may result in the formation of sulfoxides and trialkyl phosphorothioates(5). The methyl analogue, azinphos methyl, biodegraded in laboratory tests and in soil(6,7) which suggests that azinphos ethyl would also be degraded in the environment(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a structure estimation method(2), indicates that azinphos ethyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.4X10-6 mm Hg(4), and water solubility, 10.5 mg/L(5). According to a classification scheme(6), an estimated BCF of 80(SRC), from its log Kow of 3.40(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Hydrolysis half-life for azinphos ethyl was measured as 173 days at pH 6.1 and 22 °C(9). Photodegradation in aqueous environmental conditions is expected to be the most important process based on studies showing the half-life of azinphos ethyl in river water (pH 7.3) and in seawater (pH 8.1) was 9 and 11 days, respectively, when exposed to light; at 22 °C in the dark half-lives were 65 and 58 days, respectively(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), azinphos ethyl, which has a vapor pressure of 2.4X10-6 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase azinphos ethyl 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 2 hours(SRC), calculated from its rate constant of 1.9X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase azinphos ethyl may be removed from the air by wet or dry deposition(SRC). Azinphos ethyl contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of azinphos ethyl with photochemically-produced hydroxyl radicals has been estimated as 1.9X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Azinphos ethyl contains chromophores that absorb at wavelengths >290 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Degradation of organophosphorothioate pesticides by photooxidation under ultraviolet or sunlight radiation at the soil surface may result in the formation of sulfoxides and trialkyl phosphorothioates(3). Azinphos ethyl hydrolyzes in the environment to produce free thiols(3). Hydrolysis half-life for azinphos ethyl was measured as 173 days at pH 6.1 and 22 °C(4). Photodegradation in aqueous environmental conditions is expected based on studies showing the half-life of azinphos ethyl in river water (pH 7.3) and in seawater (pH 8.1) was 9 and 11 days, respectively, when exposed to light; at 22 °C in the dark half-lives were 65 and 58 days, respectively(5).

An estimated BCF of 80 was calculated in fish for azinphos ethyl(SRC), using a log Kow of 3.40(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of azinphos ethyl can be estimated to be 170(SRC). According to a classification scheme(2), this estimated Koc value suggests that azinphos ethyl is expected to have moderate mobility in soil. Using a lysimeter to measure the leachability of various pesticides, azinphos ethyl was not detected in leachate from 3,000 individual analyses conducted from 1977-1986 (detection limit 0.001 mg/L)(3). These tests were conducted using 1-1.3 m in height by 0.5 sq m of top soil with a catch base of 1 sq m(3). For soil material, loamy or silty sand with a low humus content was used where the sum of clay and silt amounted to a maximum of 30% (clay below 10%) and the content of organic bound carbon did not exceed 1.5%(3).

The Henry's Law constant for azinphos ethyl is estimated as 9.9X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 2.4X10-6 mm Hg(1), and water solubility, 10.5 mg/L(2). This Henry's Law constant indicates that azinphos ethyl is expected to be essentially nonvolatile from moist soil and water surfaces(3). Azinphos ethyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER: Azinphos ethyl was not detected in 18 well water samples collected in Siskiyou County, CA between July 1, 1994 and June 30, 1995(1). Azinphos ethyl was not detected in 5 wells sampled from 1971-1991 throughout the US(2). Azinphos ethyl was not detected in groundwater samples from 206 wells in a monitoring program conducted in Germany(3). Azinphos ethyl was detected in groundwater samples collected from 13 hydrogeological units in Spain between 1997-98 at a detection frequency of about 5%(4).|DRINKING WATER: In Spain, the concentration of azinphos ethyl, in the samples analyzed, exceeded the maximum contaminant level for drinking water (1000 ng/L) that was established in the EU Directive(1).|SURFACE WATER: Azinphos ethyl was not detected (detection limit 50 ng/L) in 20 water samples from the River Elbe near Hamburg, Germany from 1992-1993(1). Azinphos ethyl was detected in 7 water samples taken from Mornos Lake, Greece at a concentration of 0.1 ug/L(2). Azinphos ethyl was detected, not quantified, in surface water samples collected in the Netherlands(mainly from the Rhine and Meuse Rivers)(3). Azinphos ethyl was not detected (detection limit 8 parts per trillion) in the northern tract of the Adige River in Northern Italy(4). Azinphos ethyl was not detected (detection limit 10 parts per trillion) in four samples from the Po River, near Ferrarra, Italy from April to August 1988 or at two sites in the Adriatic Sea(5). Azinphos ethyl was not detected in water samples from the upper Great Lakes collected in the summer of 1974(6).|RAIN/SNOW/FOG: The occurrence of azinphos ethyl in the rain of the Axios River Basin, Greece was 2% of 205 rain events with an average concentration of 0.07 ug/L(1). Azinphos ethyl was detected in one of eight rainwater samples taken May to July 1997 in South Holland, Netherlands, the reported concentration was 0.018 ug/L, however this is below the quantification limit of 0.03 ug/L(2).

Azinphos ethyl residues were not found on 13,960 food samples analyzed by state agencies in 6 states in 1988(1). Azinphos ethyl residue was detected on 6 of 13,085 (0.045%) samples of food analyzed by state agencies in 10 states in 1989(1). A small sample of the food analyzed was imported from Mexico, Central America, and the Caribbean(1) and since azinphos ethyl is not sold in the US, it is presumed that the residues were found on the imported food. Azinphos ethyl was detected in 20 pasta samples collected in Rome, Italy in 1990 at an average concentration of 0.9 ug/kg (range not detected to 4.5 ug/kg)(2). Azinphos ethyl was not detected (detection limit 0.05 mg/kg) in 10 ready-to-eat packed table olive samples or 30 commercially packed olive oil samples analyzed from 1991-1992 in Greece(3). Azinphos ethyl was detected 2 of 2223 fruit and vegetable samples at 0.05 to 1.00 mg/kg (positive detections were in cucumber and green bean), samples were collected from Brazilian Sao Paulo General Storage and Wholesale over the period of Jan 1994 to Dec 2001(4). Azinphos ethyl was not detected (detection limit 5 ug/kg) in 298 raw milk samples obtained directly from tank trucks during delivery at nine Italian dairy plants, sampling took place Oct 2004, Jan and May 2005(5).

Azinphos ethyl was not detected (detection limit 5 ug/kg) in 298 raw milk samples obtained directly from tank trucks during delivery at nine Italian dairy plants; sampling took place Oct 2004, Jan and May 2005(1).|Many of /the organophosphorus insecticides/ are excreted in the milk ... /Organophosphorus insecticides/

Occupational exposure to azinphos ethyl may occur through inhalation and dermal contact with this compound at workplaces where azinphos ethyl is produced or used. However, azinphos ethyl is no longer produced or used in the US or Canada. Monitoring data indicate that the general population will most likely be exposed to azinphos ethyl via ingestion of food containing residue of azinphos ethyl. (SRC)

Drug Information

In mammals, following oral administration, >90% is eliminated in the urine and feces within 2 days.|...Absorption of azinphos ethyl is possible through intact skin, from the GI tract, and by mist and dust inhalation.|Following oral and IV administration of 14C-labelled azinphos-ethyl to male rats in doses of 0.1 or 2 mg/kg bw, about 60% of the activity was excreted in urine and 30% in feces in 48 hours. Approximately 30% of a 2 mg/kg dose was eliminated in bile within 24 hours; <0.1% was eliminated in expired air, indicating that the benzotriazine ring does not undergo extensive degradation. Approximately 6% of activity was present in the body 48 hours after administration, the mean concentration in tissues being equivalent to 0.1 ppm. The highest equivalent concentration (0.2-0.3 ppm (0.00002%-0.00003%)) was found in blood and 0.15-0.2 ppm (0.000015%-0.00002%) was found in lungs, liver and kidneys.|Many of /the organophosphorus insecticides/ are excreted in the milk ... /Organophosphorus insecticides/

In plants, metabolites identified include azinphos-ethyl-oxon, benzazimide, dimethylbenzazimide sulfide and dimethylbenzazimide disulfide.|In mammals, following oral administration, ...the major metabolites are the monodesethyl compound and benzazimide.|Plasma and tissue enzymes are responsible for hydrolysis /of organophosphorus compounds/ to the corresponding phosphoric and phosphonic acids. However, oxidative enzymes are also involved in the metabolism of some organophosphorus compounds. /Anticholinesterase agents/|The organophosphorus anticholinesterase agents are hydrolyzed in the body by a group of enzymes known as A-esterases or paraoxonases. These enzymes are found in the plasma and liver and hydrolyze a large number of organophosphorus compounds ... by cleaving the phosphoester, anhydride, P-F, or P-CN bonds. /Anticholinesterase agents/

Azinphos-ethyl inhibits acetylcholinesterase activity in plasma, erythrocyte, brain and submaxillary gland and a series of low doses causes the plasma activity of rats and dogs to fall rapidly to a stable level while erythrocyte acetylcholinesterase tends to fall more gradually over a longer period.|Organophosphates and their potent sulfoxidation ('-oxon') derivatives inhibit the enzyme acetylcholinesterase, allowing the accumulation of excessive acetylcholine at muscarinic receptors (cholinergic effector cells), at nicotinic receptors (skeletal neuromuscular junctions and autonomic ganglia), and in the central nervous system. Permanent damage to the acetylcholinesterase enzyme ('aging') may occur after a variable delay unless antidotal treatment with enzyme reactivator is given.|Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase (AChE). ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation following depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/|The characteristic pharmacological effects of the anti-ChE agents are due primarily to the prevention of hydrolysis of ACh by AChE at sites of cholinergic transmission. Transmitter thus accumulates, and the response to ACh that is liberated by cholinergic impulses or that is spontaneously released from the nerve ending is enhanced. With most of the organophosphorus agents ... virtually all the acute effects of moderate doses are attributable to this action. /Anticholinesterase agents/|The cardiovascular actions of anticholinesterase agents are complex, since they reflect both ganglionic and postganglionic effects of accumulated ACh on the heart and blood vessels. The predominant effect on the heart from the peripheral action of accumulated ACh is bradycardia, resulting in a fall in cardiac output. Higher doses usually cause a fall in blood pressure, often as a consequence of effects of anticholinesterase agents on the medullary vasomotor centers of the CNS. /Anticholinesterase agents/

The systemic effects of this compound are similar to parathion. It is an extremely potent systemic toxicant via ingestion, inhalation and skin contact. It may cause death or permanent injury after very short exposure to small quantities. (EPA, 1998)

Warning: Effects may be delayed up to 12 hours. Caution is advised. Note: Azinphos-ethyl is a cholinesterase inhibitor. Signs and Symptoms of Azinphos-Ethyl Exposure: Acute exposure to azinphos-ethyl may produce the following signs and symptoms: sweating, pinpoint pupils, blurred vision, headache, dizziness, profound weakness, muscle spasms, seizures, and coma. Mental confusion and psychosis may occur. Excessive salivation, nausea, vomiting, anorexia, diarrhea, and abdominal pain may also occur. The heart rate may decrease following oral exposure or increase following dermal exposure. Chest pain may be noted. Hypotension (low blood pressure) may be observed, although hypertension (high blood pressure) is not uncommon. Respiratory symptoms include dyspnea (shortness of breath), pulmonary edema, respiratory depression, and respiratory paralysis. Emergency Life-Support Procedures: Acute exposure to azinphos-ethyl exposure may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to azinphos-ethyl. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 4. Transport to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to azinphos-ethyl. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Remove contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas three times with soap and water. 6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 7. Transport to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 3. Vomiting may be induced with syrup of Ipecac. If elapsed time since ingestion of azinphos-ethyl is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step 4. Ipecac should not be administered to children under 6 months of age.Warning: Ingestion of azinphos-ethyl may result in sudden onset of seizures or loss of consciousness. Syrup of Ipecac should be administered only if victims are alert, have an active gag-reflex, and show no signs of impending seizure or coma. If ANY uncertainty exists, proceed to Step 4.The following dosages of Ipecac are recommended: children up to 1 year old, 10 mL (1/3 oz); children 1 to 12 years old, 15 mL (1/2 oz); adults, 30 mL (1 oz). Ambulate (walk) the victims and give large quantities of water. If vomiting has not occurred after 15 minutes, Ipecac may be readministered. Continue to ambulate and give water to the victims. If vomiting has not occurred within 15 minutes after second administration of Ipecac, administer activated charcoal. 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3- 1/2 oz) is recommended for adults. 6. Transport to a health care facility. (EPA, 1998)

Atropine and enzyme-reactivating agents counteract the effects of azinphos-ethyl.|A comatose patient who is diaphoretic, has pinpoint pupils and the odor of an insecticide on clothing or breath, and is noted to have muscle fasciculations represents the classic presentation of organophosphate poisoning. ... Specific steps in management include the following. 1. Decontamination. ... 2 Airway. Establish an airway if necessary. ... 3. Respiratory Status. Respiratory distress, in fact, is commonly found in these patients from multiple causes. ... 4. Cardiac Monitoring. ... 5. Cholinesterase Level. ... 6. Pralidoxime. Pralidoxime is the treatment of choice for organophosphate poisoning and should be used for nearly all patients with clinically significant orgnophosphate poisoning, particularly whose patients with muscular fasciculations and weakness. ... 7. Atropine. Atropine is the physiologic antidote for organophosphate poisoning. A trial dose of atropine should be instituted on clinical ground when one suspects organophosphate intoxication. /Organophosphate poisoning/|Never give morphine, theophylline, and theophylline ethylenediamine ... Large amounts of iv fluids generally are contraindicated because of the threat of pulmonary edema. /Organic phosphorous pesticides/|Airway protection. Insure that a clear airway exists. Intubate the patients and aspirate the secretions with a large-bore suction device if necessary. Administer oxygen by mechanically assisted pulmonary ventilation if respiration is depressed. Improve tissue oxygenation as much as possible before administering atropine, so as to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /Organophosphate pesticides/|For more Antidote and Emergency Treatment (Complete) data for AZINPHOS ETHYL (21 total), please visit the HSDB record page.

/HUMAN EXPOSURE STUDIES/ A follow-up study of 232 people three years after a history of organophosphorus pesticide poisoning disclosed only one person with slight residual blurring of vision that might have been related to the earlier poisoning, though at the time of poisoning over one third of the people had blurring, which lasted only a day or two after exposure was discontinued. The possible exceptional case had findings suggestive of basilar artery insufficiency, rather than effects of poisoning. /Organophosphorus pesticides/|/HUMAN EXPOSURE STUDIES/ A woman at 34 to 35 weeks' gestation presented in acute respiratory distress with cyanosis and tachypnea and bilateral rhonchi and crepitation. Her heart rate was 78 beats per min and her blood pressure 120/80 mm Hg, with a fetal heart rate of 140 beats per min. The mother was salivating markedly and her pupils were reduced to "pinpoint size." An uncorrected metabolic acidosis was diagnosed. Serum and erythrocyte acetylcholinesterase determinations were near zero. Cholinesterase inhibitor poisoning was felt to be the likely cause of her disorders. Administration of atropine 2.4 mg iv bolus with infusion of 0.02 mg/kg/hr lead to unacceptable fetal tachycardia. The woman had shown increased cooperativeness and secretion control until the atropine had to be stopped. A cesarean section was performed for delivery of a hypotonic infant with a 1 min Apgar score of 3. The baby was mechanically ventilated for 2 days and required atropine therapy at 0.1 mg/kg/hr for 8 days. The mother required 8 days of mechanical ventilation and 11 days of atropine therapy. In this case, the infant appeared relatively less poisoned than the mother by a presumed organophosphate exposure. /Organophosphate poisoning/|/SIGNS AND SYMPTOMS/ The symptoms of chronic poisoning due to organophosphorus pesticides include headache, weakness, feeling of heaviness in head, decline of memory, quick onset of fatigue, disturbed sleep, loss of appetite, and loss of orientation. Psychic disorders, nystagmus, trembling of the hands and other nervous system disorders can be observed in certain cases. Sometimes neuritis, paresis and paralysis develop. /Organophosphorus pesticides/|/GENOTOXICITY/ Azinphos-ethyl at concentrations of 120-160 ppm has been shown to cause abnormally high rates of chromosome breakage and abnormalities in diploid and hyperploid human cell lines in vitro... .

azinphos ethyl

Azinphos-ethyl Use and Manufacturing

Methods of Manufacturing

It is obtained by diazotization, cyclization, hydroxymethylation, chloromethylation and condensation of methyl anthranilate.

Uses

Yimian Phosphorus Organic Phosphorus Insecticide and Acaricide has good stability and durability. It is mainly used to control pests of cotton, fruit trees, vegetables and other crops.

Production

(1972) LESS THAN 4.54X10+5 G|(1975) LESS THAN 4.54X10+5 G|Due to its high toxicity, it is no longer produced or used in the United States or Canada.

Dust, emulsifiable concentrate, ULV, wettable powder.|Mixtures: (azinphos-ethyl +) azinphos-methyl; dicofol; dimethoate.|Trade name: Azinugec E

The WHO Recommended Classification of Pesticides by Hazard identifies azinphos-ethyl (technical grade) as Class IB: highly hazardous; Main Use: insecticide.|Azinphos-ethyl was introduced in 1953 by Bayer AG as a nonsystemic insecticide and acaricide.|US Patent 2,758,115; West German Patent 927,270.|USA: Not marketed.|Non-phytotoxic when used as directed. Russetting is possible on some fruit varieties with the emulsifiable concentrate formulation.

Method: EPA-RCA 8141B (GC-NPD); Procedure: gas chromatography with a nitrogen-phosphorus detector (NPD); Analyte: azinphos ethyl; Matrix: water, soil, waste samples; Detection Limit: not provided.|Method: EPA-RCA 8141B (GC-FPD); Procedure: gas chromatography with flame photometric detector; Analyte: azinphos ethyl; Matrix: water, soil, waste samples; Detection Limit: not provided.|Product analysis by colorimetric measurement of the phosphorodithioate moiety as a complex ... Residues determined by GLC.|EPA Method 1618. Combined method using wide bore capillary column GC with selective ECD for the determination of organo-halide pesticides and PCBs, organo-phosphorus pesticides, and phenoxy-acid herbicides. Under the prescribed conditions for ethyl guthion, the method has a detection limit of 22.00 ng/l as defined by EPA.|Analyses of residues. Alkaline hydrolysis, diazotization, coupling of the resulting anthranilic acid with N-(1-naphthyl)ethylenediamine, and phtometric determination of the red coloration at 555 nm.

GLC METHOD USING A (63)NI ECD FOR DETERMINATION OF AZINPHOS ETHYL IN HUMAN PLASMA AND IN MOUSE PLASMA, TISSUE, AND FAT SENSITIVITY: 0.005 PPM IN HUMAN PLASMA, 0.01 IN MOUSE PLASMA, 0.08 PPM IN MOUSE LIVER, 0.05 PPM IN MOUSE BRAIN, & 0.01 PPM IN MOUSE FAT.

Agrochemicals -> Acaricides, Insecticides|INSECTICIDES

Computed Properties

Molecular Weight:345.4
XLogP3:3.4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:7
Exact Mass:345.03707073
Monoisotopic Mass:345.03707073
Topological Polar Surface Area:121
Heavy Atom Count:21
Complexity:440
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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