파라싸이온(파라티온)

Parathion

HCID 991CAS 56-38-2

기본 정보

표준 SMILES
CCOP(=S)(OCC)Oc1ccc([N+](=O)[O-])cc1
InChIKey
LCCNCVORNKJIRZ-UHFFFAOYSA-N
분자식
C10H14NO5PS
평균 분자량
291.26 g/mol
단동위원소 질량
291.03303072

이름 및 식별자

우선 이름
Parathion
IUPAC
diethoxy-(4-nitrophenoxy)-sulfanylidene-lambda5-phosphane
현지명
파라싸이온(파라티온)
영어명
Parathion
분자식
C10H14NO5PS
분자량
291.26

이름 및 동의어

parathionethyl parathionParathion-ethylThiophos56-38-2alkronParaphosdanthionphosphostigminestathionAphamiteFosferno
이름 더 보기
파라싸이온(파라티온)파라치온O,O'-다이에틸-O-4-나이트로페닐포스포로티오티오에이트(파라티온-ISO)파라티온O,O-디에틸O-(p-니트로페닐)티오노인산염DNTPAAT1605ETHYLPARATHIONEe605SulphosPARATIONDNTP MIXTURE
RhodiatoxAlleronEtilonFolidolParawetPhoskilNirancorothion

데이터베이스 식별자

CAS
56-38-2
PubChem CID
991
DTXSID
DTXSID7021100
ChEMBL
CHEMBL261919
ChEBI
CHEBI:27928
UNII
61G466064D
EC Number
200-271-7
Nikkaji
J2.318C

물성

구조 계산 물성

XLogP
3.8
극성 표면적
106 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
6
회전 가능 결합 수
6
무거운 원자 수
18

실험 및 물리화학적 성질

LogP · 3건

Log Kow= 3.83

3.83

3.8

Odor · 3건

Usually has a faint odor

... Garlic-like odor ...

Phenol-like odor

Density · 6건

1.26 (EPA, 1998) - Denser than water; will sink

1.26 AT 25 °C/4 °C

Relative density (water = 1): 1.26

1.27

1.2681 @ 20°C

1.27

Viscosity15.30 CENTIPOISE AT 25 °C
Color/Form · 4건

The pure material is a yellowish liquid at temperatures above 6 °C

Pale-yellow to dark-brown liquid ... [Note: A solid below 43 degrees F. Pesticide that may be absorbed on a dry carrier].

Pale yellow liquid

Deep brown to yellow liquid

Solubility · 6건

less than 1 mg/mL at 73 °F (NTP, 1992)

PRACTICALLY INSOL IN PETROLEUM ETHER, KEROSENE, & USUAL SPRAY OILS

COMPLETELY SOL IN ALCOHOLS, ESTERS, ETHERS, KETONES, AROMATIC HYDROCARBONS, ANIMAL & VEGETABLE OILS

SOL IN CHLOROFORM

Water solubility = 11 mg/l @ 20 °C

Completely miscible with most organic solvents, e.g. dichloromethane >200, isopropanol, toluene, hexane 50 to 100 (all in g/l at 20 °C).

물리화학적 성질

녹는점
6.1 °C · 6.1°C
끓는 점
375 °C · 375°C
밀도
1.26 · 1.26
증기압
0.47 at · 0.470 at 20 °C, 0.942 at 25 °C, 1.84 at 30 °C, 3.53 at 35 °C, 6.62 at 40 °C, 12.18 at 45 °C (gassaturation method, Spencer et al., 1979)
굴절률
25 · nD25 1.5370
인화점
120 °C · 120 °C
화학적 성질 · 1건

Pure parathion is a pale yellow liquid with a faint odor of garlic, while technical parathion is a deep brown to yellow liquid. It is sparingly soluble in water, but soluble in alcohols, aromatic hydrocarbons, esters, ethers, n-hexane, dichloromethane, 2-propanol, toluene,and ketones. Parathion is one of the most acutely toxic pesticides and the US EPA has classifi ed parathion as an RUP, meaning it should only be handled by qualifi ed, trained, and certifi ed workers. In January 1992, the US EPA announced the cancellation of parathion for all uses on fruit, nut, and vegetable crops. Parathion was used for the control of pests of fruits, nuts, and vegetable crops. The only uses retained are those on alfalfa, barley, corn, cotton, sorghum, soybeans, sunfl owers, and wheat. Further, to reduce exposure of agricultural workers, parathion may only be applied to these crops by commercially certifi ed aerial applicators and treated crops may not be harvested by hand. Parathion is a broad spectrum, organophosphate pesticide used to control many insects and mites.

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral];H311: Toxic in contact with skin [Danger Acute toxicity, dermal];H330: Fatal if inhaled [Danger Acute toxicity, inhalation];H372 **: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure];H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

유해성 정보

Regulatory Information · 5건

Hazard Traits - Carcinogenicity; Developmental Toxicity; Environmental tox; Neurotoxicity; Other Toxicological Hazard Traits;Authoritative List - ATSDR Neurotoxicants; CA TACs; CECBP - Priority Chemicals; CWA 303(d); IARC Carcinogens - 2B; Prop 65;Report - regardless of intended function of ingredient in the product

Regulation (EC) No 1107/2009 (amended)

Ethyl Parathion is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

01/520/EC

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Phosphorothioic acid, O,O-diethyl O-(4-nitrophenyl) ester: Environment tier I assessment;IMAP assessments - Phosphorothioic acid, O,O-diethyl O-(4-nitrophenyl) ester: Human health tier I assessment
DOT LabelPoison
Fire Hazards · 2건

When heated to decomposition, it can emit toxic fumes of oxides of nitrogen, phosphorus, and sulfur. High pressure hoses may scatter material from broken containers. Containers may explode when heated. Stable in distilled water and in acid solution. Store below 77-86F. It slowly decomposes in air and hydrolyzes in the presence of alkaline material. Containers may explode when heated. (EPA, 1998)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Liquid formulations containing organic solvents may be flammable.

Fire Potential · 4건

... NOT HIGHLY FLAMMABLE

... RESIDUE SUPPORT COMBUSTION WHEN TEMPERATURE REACHES 221 °C.

Material itself does not burn or burns with difficulty.

Combustible when exposed to heat or flame.

Health Hazards · 1건

This material is extremely toxic; the probable oral lethal dose is 5-50 mg/kg, or between 7 drops and 1 teaspoonful for a 150-lb. person. As little as 1 drop can endanger life if splashed in the eye. Toxicity is highest by inhalation. People at special risk are those with a history of glaucoma, cardiovascular disease, hepatic disease, renal disease, or central nervous system abnormalities. (EPA, 1998)

안전 및 보호

Fire Fighting · 2건

Use water spray to keep fire-exposed containers cool. If a leak or spill has not ignited, use water spray to disperse vapors and to provide protection for firefighters. Water spray may be used to flush spills away from exposures. Fight advanced or massive fires from a safe distance or from a protected location. Special protective clothing should be worn; normal protective clothing may be penetrated.;Use water spray, dry chemical, foam, or carbon dioxide. (EPA, 1998)

Use water spray, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4건

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

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

First Aid · 2건

CAUTION: Parathion is a cholinestorase inhibitor. It has been reported that as little as one drop of parathion can endanger life if splashed in the eye. Toxicity is highest by inhalation.;Signs and Symptoms of Acute Parathion Exposure: Acute exposure to parathion may produce the following signs and symptoms: pinpoint pupils, blurred vision, headache, dizziness, muscle spasms, and profound weakness. Vomiting, diarrhea, abdominal pain, seizures, and coma may also occur. The heart rate may decrease following oral exposure or increase following dermal exposure. Hypotension (low blood pressure) is not uncommon. Respiratory symptoms include dyspnea (shortness of breath), respiratory depression, and respiratory paralysis. Psychosis may occur.;Emergency Life-Support Procedures: Acute exposure to parathion 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 parathion.;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 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 parathion.;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 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 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 parathion is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Soap wash immediately - If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Safe StorageProvision to contain effluent from fire extinguishing. Separated from strong oxidants and food and feedstuffs. Well closed. Keep in a well-ventilated room.
Firefighting HazardsHigh pressure water hoses may scatter parathion from broken containers, increasing the contamination hazard.
Exposure Control and Personal Protection · 2건

Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Total p-nitrophenol in urine = 0.5 mg/g' Sample at end of shift; [ACGIH, 2020]]

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

독성 정보

Toxicological InformationCDC-ATSDR Toxicological Profile
Body Burden · 1건

Blood of victims of parathion poisoning (caused by dermal contact during harvesting of tobacco less than 24 hr after application of parathion) contained 34 ng/l of parathion(1). Range of serum parathion levels in 5 workers 3, 7, and 24 hr after a 5 hr exposure to parathion in a cotton field 24 hr after treatment were 3 to 13, 3 to 12, and 1 to 8 ppb, respectively(2). Orchard workers dermally absorbed an avg of 2 mg parathion per each application, in addition to an inhalation exposure of 0.020 mg/hr(3).

Treatment · 1건

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Interactions · 5건

COMBINED EFFECTS OF TWO ORGANOPHOSPHATES CAN ... BE ... ANTAGONISTIC ... /MALATHION/ PLUS PARATHION & DRUGS THAT COMPETE WITH ORGANOPHOSPHATES FOR TARGET ESTERASES MAY ENHANCE ORGANOPHOSPHATE TOXICITY OR VICE VERSA. ... METHYLMERCURY ENHANCES ANTICHOLINESTERASE ACTIVITY OF PARATHION IN QUAIL ...

... TREATMENT OF RATS WITH DDT, /PHENOBARBITAL, OR BENZO(A)PYRENE/ ... LESSENED TOXICITY OF PARATHION, BUT ... /OTHERS/ DEMONSTRATED THAT ALTHOUGH TREATMENT OF MICE WITH CHLORDANE AFFORDED PROTECTION, DDT DID NOT.

Incubation of both parathion and chlorpyrifos at various concn with mouse hepatic microsomes resulted in the inhibition of prodn of paraoxon, p-nitrophenol, chlorpyrifos oxon, and 3,5,6-trichloro-2-pyridinol, which was characteristic of mixed-type inhibition. This kinetic behavior could arise as a result of competitive interactions of one and two with multiple forms of microsomal cytochrome p450.

Single pass perfusion of mouse livers in situ with parathion resulted in formation of the cholinesterase inhibitor paraoxon, p-nitrophenol, p-nitrophenyl sulfate, and p-nitrophenyl glucuronide. Daily pretreatment of mice with phenobarbital (80 mg/kg, ip) for 4 days induced hepatic cytochrome p450 content, as well as oxidative activation and oxidative detoxification of parathion, as measured in vitro. Phenobarbital pretreatment did not alter production of paraoxon from parathion in mouse livers perfused in situ, although it increased production of p-nitrophenol, p-nitrophenyl sulfate, and p-nitrophenyl glucuronide. Additionally, phenobarbital pretreatment antagonized the acute toxicity of parathion in mice. These results indicate that phenobarbital pretreatment clearly induces that form(s) of cytochrome p450 catalyzing conversion of parathion to paraoxon. Increased amounts of catalyzed conversion of parathion to paraoxon. Increased amounts of paraoxon do not exit perfused livers from phenobarbital pretreated mice, but the enhanced detoxification of parathion to p-nitrophenol, p-nitrophenyl sulfate, and p-nitrophenyl glucuronide likely results in the observed antagonism of parathion's acute toxicity.

For more Interactions (Complete) data for PARATHION (9 total), please visit the HSDB record page.

Target Organs · 2건

Endocrine (Glands and Hormones), Immunological (Immune System), Neurological (Nervous System)

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

Health Effects · 1건

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergi

규제 정보

Regulatory Information · 5건

Hazard Traits - Carcinogenicity; Developmental Toxicity; Environmental tox; Neurotoxicity; Other Toxicological Hazard Traits;Authoritative List - ATSDR Neurotoxicants; CA TACs; CECBP - Priority Chemicals; CWA 303(d); IARC Carcinogens - 2B; Prop 65;Report - regardless of intended function of ingredient in the product

Regulation (EC) No 1107/2009 (amended)

Ethyl Parathion is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

01/520/EC

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

RCRA Requirements · 1건

P089; As stipulated in 40 CFR 261.33, when parathion, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

FIFRA Requirements · 3건

Tolerances are established for residues of the insecticide parathion or its methyl homolog in or on the following raw agricultural commodities: alfalfa (fresh); alfalfa hay; almonds; almond hulls; apples; apricots; artichokes; avocados; barley; beans; beet greens (alone); beets (with or without tops); beets, sugar; beets, sugar (tops); blackberries; blueberries (huckleberries); boysenberries; broccoli; brussels sprouts; cabbage; carrots; cauliflower; celery; cherries; citrus fruits; clover; collards; corn; corn, forage; cottonseed; cranberries; cucumbers; currants; dates; dewberries; eggplants; endive (escarole); figs; filberts; garlic; gooseberries; grapes; grass (forage); guavas; hops; kale; kohlrabi; lettuce; loganberries; mangoes; melons; mustard greens; mustard seed; nectarines; oats; okra; olives; onions; parsnips (with or without tops); parsnip greens (alone); peaches; peanuts; pears; peas; peas, forage; pecans; peppers; pineapples; plums (fresh prunes); potatoes; pumpkins; quinces; radishes (with or without tops); radish, tops; rape seed; raspberries; rice; rutabagas (with or without tops); rutabaga tops; safflower seed; sorghum; sorghum fodder; sorghum forage; soybeans; soybean hay; spinach; squash; strawberries; summer squash; sugarcane; sugarcane fodder; sugarcane forage; sunflower seed; sweet potatoes; Swiss chard; tomatoes; turnips (with or without tops); turnips greens; vetch; walnuts; wheat; and youngberries.

While petitions for tolerances for negligible residues are pending and until action is completed onthese petitions, interim tolerances are established for residues of the listed pesticide chemicals in or on raw agricultural commodities as follows: parathion or its methyl homolog, herbicide /SRP: Insecticide/, rye.

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. Parathion 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: 0155; Pesticide type: insecticide; Registration Standard Date: 09/03/86; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Parathion; Data Call-in (DCI) Date(s): 10/19/92, 11/23/93, 10/13/95, 03/14/96; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Atmospheric Standards · 1건

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Parathion is included on this list.

CERCLA Reportable Quantities · 2건

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

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. Parathion is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 lbs.

Clean Water Act Requirements · 2건

Freshwater aquatic organisms and their uses should not be affected unacceptably if the four day average concn of parathion does not exceed 0.013 ug/l more than once every three years on the average and if the one hour average concn does not exceed 0.065 ug/l more than once every three years on the average.

Designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance.

안전 데이터

OEB
D
OEL
TWA: 0.05 mg/m3 [skin]
wgk
3
IDLA
10 mg/m3
rtecs
TF4550000
ridadr
UN 3278

화학 및 산업

약리 정보

Mechanism of Action · 5건

Parathion is converted in the body in part to paraoxon, a strong inhibitor of the enzyme acetyl cholinesterase. Upon inhibition of this enzyme in the tissues, acetylcholine, the substance responsible for transmission of nerve impulses in much of the nervous system, accumulates, producing an initial overstimulation, and subsequent blockage of nerve stimuli.

... PARATHION & METHYL PARATHION ... DEPEND ON OXIDATIVE ACTIVATION BY REPLACEMENT OF THIONO-SULFUR WITH OXYGEN FOR ... TOXICITY.

The toxic effects of thiono-sulfur containing compounds appear to be partially the result of metabolism to reactive intermediates by cytochrome p450 containing monooxygenase enzyme systems. Covalent binding of (atomic) sulfur released in the cytochrome p450 monooxygenase catalyzed metabolism of certain thiono-sulfur compounds appears to be responsible for inhibition of monooxygenase activity & the loss of cytochrome p450 seen on admin of these compounds in vivo & incubation with cytochrome p450 monooxygenase enzymes in vitro. Liver necrosis & perhaps the induction of lung edema & neoplasia, as well as other effects of thiono-sulfur containing compounds are more likely the result of the covalent binding of electrophilic S-oxides or S-dioxides or carbene derivatives to tissue macromolecules. The rationale for implicating metabolites of thiono-sulfur compounds other than sulfur in these effects derives from the experiments with thioacetamide & the fact that atomic sulfur is highly reactive & appears to bind predominantly or exclusively to cytochrome p450.

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/

For more Mechanism of Action (Complete) data for PARATHION (9 total), please visit the HSDB record page.

Biological Half-LifeElimination half-life of about 8 hours after inhalation; After dermal exposure, only 9.7% of dose eliminated in urine as p-nitrophenol within 5 days; [ACGIH]
Metabolism/Metabolites · 6건

THE METABOLISM OF ... PARATHION ... HAS BEEN EXTENSIVELY STUDIED IN A WIDE VARIETY OF ORGANISMS, INCL MICROORGANISMS, PLANTS, INSECTS & MAMMALS. ... /ITS BIOTRANSFORMATION/ DEPENDS ON OXIDATIVE ACTIVATION BY REPLACEMENT OF THIONO SULFUR WITH OXYGEN FOR ... TOXICITY. COMPETING WITH THIS INTOXICATION REACTION ARE HYDROLYSIS REACTIONS THAT RESULT IN DETOXIFICATION. THE RING NITRO GROUP CAN ALSO BE REDUCED, PARTICULARLY IN BOVINE RUMEN FLUID, TO AMINO GROUP; THIS RESULTS IN AMINO PARATHION ... OXIDATIVE ACTIVATION TAKES PLACE PRIMARILY IN LIVER. A NUMBER OF ... /STUDIES/ HAVE SHOWN THAT, IN LIVER MICROSOMAL MIXED FUNCTION OXIDASE SYSTEMS, PRESENCE OF REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE & OXYGEN ARE RESPONSIBE FOR THIS REACTION. THE CONVERSION OF PARATHION TO PARAOXON HAS BEEN DEMONSTRATED ... IN VIVO & IN VITRO. DEGRADATIVE REACTIONS THAT RESULT IN DETOXIFICATION OF PARATHION ... INVOLVE ... DEARYLATION. THE RESULTING ... DIMETHYL PHOSPHORIC ACIDS ARE ESSENTIALLY NONTOXIC.

Although the main degradation reaction of parathion is preceded by oxidation to oxon and by hydrolysis to p-nitrophenol, reduction to aminoparathion and oxidation to aminoparaoxon have been observed in microsomes /from female albino S-D rat liver cells; rat liver mitochondrial subfraction/. Parathion is also reduced to aminoparathion through nitrosoparathion, and hydroxyamino parathion successively in plants /such as spinach/.

MAJOR METABOLIC PRODUCTS /OF PARATHION METABOLISM IN ANIMALS/ INCL 4-NITROPHENYL PHOSPHATE, DIETHYL HYDROGEN PHOSPHOROTHIONATE, DIETHYL HYDROGEN PHOSPHATE & P-NITROPHENOL. ... THE REACTION RESULTING IN THE FORMATION OF DIETHYL HYDROGEN PHOSPHOROTHIONATE & P-NITROPHENOL REQUIRES THE SAME COFACTORS ... /SUCH AS/, OXYGEN & REDUCED NICOTINAMIDE ADENINE DICUCLEOTIDE , AS THE BIOTRANSFORMATION OF PARATHION INTO 4-NITROPHENYL PHOSPHATE.

WEANLING HOLTZMAN RATS, MALE & FEMALE, WERE INJECTED WITH PARATHION. COCHROMATOGRAPHY WAS USED TO IDENTIFY TISSUE RESIDUES /WHICH CONSISTED/ ... OF DIETHYLPHOSPHORATE, DIETHYL PHOSPHOROTHIOATE, PARAOXON & PARATHION. WHEREAS LIVER, KIDNEY, SKELETAL MUSCLE & PLASMA CONTAINED RESIDUES OF ALL FOUR COMPOUNDS, ONLY PARATHION & PARAOXON WERE FOUND IN BRAIN & FAT TISSUES. DEPA & DEPTA OCCURRED AS THE MAJOR METABOLITES IN URINE WITH PARATHION & PAROXON PRESENT AS TRACES ONLY. ... IN VITO STUDIES WITH LIVER HOMOGENATES SHOWED THAT ADULT MALE RATS POSSESS HIGHER ACTIVITY THAN WEANLINGS OR ADULT FEMALES FOR BOTH THE OXIDATIVE & HYDROLYTIC PATHWAYS OF PARATHION.

For more Metabolism/Metabolites (Complete) data for PARATHION (12 total), please visit the HSDB record page.

Parathion has known human metabolites that include Paraoxon.

MeSH Pharmacological Classification · 2건

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.

Absorption, Distribution and Excretion · 5건

... RAPIDLY TRANSPORTED THROUGHOUT SYSTEM /OF ANIMALS/ AFTER ABSORPTION. ... ONLY TISSUE ACCUMULATION OF PARATHION ... THAT HAS BEEN OBSERVED IS IRREVERSIBLE BINDING TO ESTERASE ENZYMES.

PARATHION IS ABSORBED THROUGH SKIN, THE GUT, & BY INHALATION. IN MICE, PARATHION IS ABSORBED TWICE AS RAPIDLY THROUGH THE GUT AS THROUGH THE SKIN. AFTER SC INJECTIONS OF (32)P PARATHION TO MICE, AUTORADIOGRAPHY SHOWED IT TO BE VERY SLOWLY ABSORBED, WITH LOW LEVEL OF RADIOACTIVITY IN THE BLOOD. HIGHEST ACTIVITY APPEARED IN SALIVARY GLANDS & CERVICAL FAT, FOLLOWED BY LIVER, KIDNEY, GASTRIC WALL, THYROID, SPLEEN, & LUNG. LESS ACTIVITY WAS NOTED IN CNS, MUSCULATURE & BONE MARROW. PERCUTANEOUS ABSORPTION RATES OF PARATHION & ITS METABOLITE PARAOXON WERE USED TO COMPARE IV INFUSION & DERMAL ABSORPTION IN RABBITS: PARAOXON WAS ABSORBED ABOUT 5 TIMES MORE RAPIDLY ...

... THE FACT THAT PARATHION HAS BEEN IDENTIFIED IN DEAD FETUSES OF MOTHERS POISONED WITH OVERDOSE IS STRONG EVIDENCE FOR ... PLACENTAL TRANSFER ...

PARATHION & PARATHION METABOLITES COULD NOT BE DETECTED IN MILK OF COWS CHRONICALLY TREATED ... @ ... LEVELS UP TO 32 MG/KG BODY WT/DAY.

For more Absorption, Distribution and Excretion (Complete) data for PARATHION (21 total), please visit the HSDB record page.

Cellular LocationsMembrane

용도 및 제조

Uses · 6건

Parathion is primarily used as an insecticide on fruit, cotton, wheat, vegetables, and nut crops.

In the U.S. parathion may be used only by licensed applicators on alfalfa, barley, corn, cotton, sorghum, soybeans, sunflowers, and wheat. [EXTOXNET]

Use on fruit, nut and vegetable crops cancelled by EPA in 1992; [EXTOXNET]

Farming (Pesticides) [Category: Industry]

... Parathion controls a variety of insects such as aphids, mites, beetles, Lepidoptera, leaf hoppers, leafminers, and other pests found on fruits, cotton, vegetables, and forage crops. It also controls several soil insects such as wireworms, rootworms, and symphilids.

Used for control of nematodes in beet & ornamentals

Impurities · 2건

The following impurities were identified in one sample of technical-grade parathion: O,O-diethyl thiophosphoryl chloride; O,O,O-triethyl thiophosphate; O,O-diethyl S-ethyl thiophosphate; O,O-diethyl S-ethyl dithiophosphate; nitrophenetole; nitrophenol; parathion isomers; & the dithio analogue of parathion.

The analysis of technical organophosphorus insecticides by (31)P nuclear magnetic resonance showed the major known toxic contaminants to be simple trialkyl phosphorothio- and -dithioic acid esters and the S-alkyl insecticide isomers. Small amt of the bis derivatives & the dithiopyrophosphate were also detected. These contaminants included both byproducts from the synthesis as well as degradation products. This procedure was used to analyze the following technical grade products: ronnel, sulfotepp, methyl parathion, dimethoate, malathion, methidathion, ethion, phosalone, & fenitrothion. /Organophosphorous insecticides/

U.S. Production1970; Approximately 15,259,000 lb of parathion were produced.
Consumption Patterns · 3건

INSECTICIDE FOR WHEAT, 49%; DECIDUOUS FRUITS & NUTS, 14%; VEGETABLES, 14%; SORGHUM, 11%; COTTON, 4%; CITRUS, 1%; OTHER FIELD CROPS EG, BARLEY & OATS, 7% (1982 AGRICULTURAL CROP USE)

(1978) 3.27X10+9 G (CONSUMPTION)

(1982) 3.90X10+9 G (CONSUMPTION)

Methods of Manufacturing · 4건

PARATHION ... /IS/ PREPARED BY THE REACTION OF DIETHYL ... PHOSPHOROCHLORIDOTHIOATE WITH SODIUM P-NITROPHENATE.

In the 1st step, ethyl dithiophiosphone acid ... /is/ prepared by reacting ... anhydrous ethyl alcohol with ... phosphorous pentasulfide. ... The chlorination step follows & may use elemental chlorine, sulfur monochloride or sulfur dichloride. ... A production & waste schematic for the overall process of parathion manufacture /for a typical plant producing 20,000 tons per year/ is. ... /described by/ Gruber GI (TRW Systems Group); Report EPA/530/SW-118c, Washington, DC, USEPA (April 1975). To ... thiophosphoryl chloride ... an approx 20% soln of sodium ethylate in ethyl alcohol /is added/. ... To this mixture ... p-nitrophenol ... /was added/ & to this resulting solution was added. ... Approx 20% soln of sodium ethylate in ethyl alcohol ... water /is added to the reaction mixture/ in order to dissolve sodium chloride & to separate the O,O-diethyl O-p-nitrophenyl thiophosphate from the residual alcohol.

Original prepn: Thurston, FIAT Report 949 (1946); Coates, Topley, BIOS Final Report 1808 (1947). See also Fletcher et al., J Am Chem Soc 70, 3943 (1948).

From sodium ethylate, thiophosphoryl chloride, and sodium p-nitrophenate.

Formulations/Preparations · 4건

Technical parathion is available as a dark brown liquid containing 98.5% active ingredient & 1.5% inert ingredients.

... Granules, ULV liquid ...

Wettable powder; emulsifiable concentrate; granule; dispersible powder; capsule suspension; aerosol.

Mixtures (parathion +) endosulfan; ethion; lindane; oxydemeton-methyl; petroleum oil; tetradifon; malathion; malathion + methoxychlor; parathion-methyl; thiometon; methamidophos.

응용 분야 · 3건

개요After exposure to parathion ethyl, one case of a bullous contact dermatitis was reported.

용도Parathion is an organophosphate insecticide used on cotton, rice and fruit trees.

일반 설명Light-yellow liquid, Parathion turn solid at 6° C, a deadly poison by all routes. Organic phosphate insecticide, acts as an inhibitor of cholinesterase.

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