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Acetophos

Acetophos structure

Acetophos 

structure
  • CAS No:

    2425-25-4

  • Formula:

    C8H17O5PS

  • Chemical Name:

    Acetophos

  • Synonyms:

    Acetic acid,2-[(diethoxyphosphinyl)thio]-,ethyl ester;Acetic acid,mercapto-,ethyl ester,S-ester with O,O-diethyl phosphorothioate;Acetic acid,[(diethoxyphosphinyl)thio]-,ethyl ester;Acetic acid,mercapto-,ethyl ester,O,O-diethyl phosphorothioate;Acetaphos;Acetophos;Acetoxon;Phosphorothioic acid,O,O-diethyl ester,S-ester with ethyl mercaptoacetate;O,O-Diethyl S-(carbethoxy)methyl phosphorothiolate;O,O-Diethyl S-ethoxycarbonylmethyl phosphorothioate

Acetophos Basic Attributes

256.25600

256.26

J4K0KB7I7Y

DTXSID8041581

Liquid

Characteristics

96.94000

2.46380

1.1826 g/cm3 @ Temp: 20 °C

138 °C @ Press: 3 Torr

135.1ºC

1.463

In water, 2.74X10+3 mg/L at 25 deg C (est)

... Must be stored in its sealed original containers, in well-aired, fresh and dry storehouses or in shaded and possibly well-aired places. It is recommended that the product's tempeture ... not exceed 25-30 deg c, and keep ... away from sources of heat, free flames or spark-generating equipment. Containers must be stacked in such a way as to permit free circulation of air ... at bottom and inside of piles. Storage areas must be located at suitable distance from inhabited buildings, animal shelt

1.6X10-4 mm Hg at 25 deg C (est)

Henry's Law constant = 7.6X10-10 atm-cu m/mol at 25 °C (est)

The affinity constants Ka, and the phophorylation constants, Kp, were determined for a series of homologs of diethyl malaoxon. The Ka values with respect to acetylcholinesterase had the following order succinate diethyl malaoxon, beta-glutarate diethyl malaoxon, alpha-glutarate diethyl malaoxon, and malonate diethyl malaoxon, and ranged from 3.6 to 0.15 mm for the succinate and malonate derivatives, respectively. The descending order of Kp values was alpha-glutarate, malonate, succinate, beta-glutarate, and varied from 77 to 0.5 min. The Ka values for the acetoxon homologs, acetoxon, methyl acetoxon, methyl isopropoxon, methyl propoxon, isopropoxon, and propoxon were of the same order as those of the comparable malaoxon homologs, suggesting that only one carbethoxy group was necessary for initial binding.|Hydroxyl radical reaction rate constant = 4.6X10-11 cu cm/molec-sec at 25 °C (est)

Safety Information

II

6.1(a)

UN 3018

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.

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.

Toxicity

Acetoxon's former production may have resulted in its release to the environment through various waste streams; its use as an insecticide(1) will have resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 31(SRC), determined from a structure estimation method(2), indicates that acetoxon is expected to have very high mobility in soil(SRC). Volatilization of acetoxon from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.6X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Acetoxon is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.6X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soil were not available(SRC,2013).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 31(SRC), determined from a structure estimation method(2), indicates that acetoxon is not 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 7.6X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 2(SRC), from an estimated log Kow of 1.06(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis half-lives have been estimated as 51 and 5.1 days at pH values of 7 and 8, respectively(6). The estimated hydrolysis half-lives for the phosphorus ester fragment are 2.2 days and 14 hours at pH 7 and 8, respectively(2). Biodegradation data in water were not available(SRC,2013).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetoxon, which has an estimated vapor pressure of 1.6X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase acetoxon 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 7.6 hours(SRC), calculated from its rate constant of 4.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Acetoxon 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 acetoxon with photochemically-produced hydroxyl radicals has been estimated as 4.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7.6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 1.6 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 51 and 5.1 days at pH values of 7 and 8, respectively(2). The estimated hydrolysis half-lives for the phosphorus ester fragment are 2.2 days and 14 hours at pH 7 and 8, respectively(3). Acetoxon contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 2 was calculated in fish for acetoxon(SRC), using an estimated log Kow of 1.06(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of acetoxon can be estimated to be 31(SRC). According to a classification scheme(2), this estimated Koc value suggests that acetoxon is expected to have very high mobility in soil.

The Henry's Law constant for acetoxon is estimated as 7.6X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that acetoxon is expected to be essentially nonvolatile from water and moist soil surfaces(2). Acetoxon is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.6X10-4 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to acetoxon may have occurred through inhalation and dermal contact with this compound at workplaces where acetoxon was produced or used. Although, use data indicate that acetoxon is an insecticide there is no indication that it is currently used. (SRC)|Organophosphates are efficiently absorbed by inhalation, ingestion, and skin penetration. /Organophosphate pesticides/

Drug Information

Toxicants of this class phosphorylate almost irreversibly varying amt of acetylcholinesterase enzyme of tissues, allowing accum of acetylcholine at cholinergic neuro-effector junctions (muscarinic effects), and at skeletal muscle myoneural junctions and in autonomic ganglia (nicotinic effects). /Organophosphate pesticides/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organophosphates and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Aggressive airway control may be needed. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Organophosphates and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously and consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer atropine. Correct hypoxia before giving atropine ... . Administer pralidoxime chloride (2 PAM). USE UNDER DIRECT PHYSICIAN ORDERS ONLY ... . Treat seizures with adequate atropinization and correction of hypoxia. In rare cases diazepam or lorazepam may be necessary ... . Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organophosphates and related compounds/

/SIGNS AND SYMPTOMS/ Nausea ... vomiting, abdominal cramps, diarrhea, excessive salivation ... Headache, giddiness, vertigo and weakness. Rhinorrhea and sensation of tightness in chest are common in inhalation exposure. Blurring or dimness of vision, miosis ... tearing, ciliary muscle spasm, loss of accommodation and ocular pain ... mydriasis ... sometimes seen ... probably due to sympatho-adrenal discharge. Loss of muscle coordination, slurring of speech, fasciculations and twitching of muscles (particularly of tongue and eyelids), and generalized profound weakness. Mental confusion, disorientation and drowsiness. Difficulty in breathing, excessive secretion of saliva and of respiratory tract mucus, oronasal frothing, cyanosis, pulmonary rales, rhonchi and hypertension (presumably due to asphyxia). Random jerky movements, incontinence, convulsions, and coma. Death primarily due to respiratory arrest arising from failure of respiratory center, paralysis of respiratory muscles, intense bronchoconstriction or all three. /Parathion/

Acetophos Use and Manufacturing

Uses

For acetoxon (USEPA/OPP Pesticide Code: 334404) 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 /Former use in the USA/

Method: OSHA 62; Procedure: gas chromatography with flame photometric detector; Analyte: malathion; Matrix: air; Detection Limit: 0.030 mg/cu m. /Malathion/|Method: EPA-OGWDW/TSC 527; Procedure: gas chromatography-mass spectrometry; Analyte: malathion; Matrix: drinking water; Detection Limit: 0.057 ug/L. /Malathion/|Method: EPA-OW/OST 1699; Procedure: high resolution gas chromatography combined with high resolution mass spectrometry; Analyte: malathion; Matrix: water, soil, sediment, biosolids, and tissue; Detection Limit: 296 pg/L. /Malathion/|Method: EPA-RCA 8141B (GC-FPD); Procedure: gas chromatography with flame photometric detector; Analyte: malathion; Matrix: water, soil, waste samples; Detection Limit: 5.5 ug/L. /Malathion/|For more Analytic Laboratory Methods (Complete) data for ACETOXON (18 total), please visit the HSDB record page.

Computed Properties

Molecular Weight:256.26
XLogP3:0.9
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:9
Exact Mass:256.05343181
Monoisotopic Mass:256.05343181
Topological Polar Surface Area:87.1
Heavy Atom Count:15
Complexity:223
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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