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Chlorethoxyfos

Chlorethoxyfos structure

Chlorethoxyfos 

structure
  • CAS No:

    54593-83-8

  • Formula:

    C6H11Cl4O3PS

  • Chemical Name:

    Chlorethoxyfos

  • Synonyms:

    Phosphorothioic acid,O,O-diethyl O-(1,2,2,2-tetrachloroethyl) ester;O,O-Diethyl O-(1,2,2,2-tetrachloroethyl) thionophosphate;SD 208304;DPX 43898;Fortress;Chlorethoxyfos;104559-35-5;119791-49-0

  • Categories:

    Agrochemicals  >  Insecticides

Description

Gray to reddish-brown granular solid or colorless liquid. Mild sulfur-like odor. Chlorethoxyfos is a colorless liquid. Technical chlorethoxyfos is a light-to- dark brown liquid. Stable at room temperature for >18 months; stable at 55°C for 2 weeks. Chlorethoxyfos is characterized as having a “strong” odor.


COLOURLESS LIQUID.


Chlorethoxyfos is an organic thiophosphate, an organothiophosphate insecticide and an organochlorine insecticide. It has a role as an agrochemical and an EC 3.1.1.7 (acetylcholinesterase) inhibitor.

Chlorethoxyfos Basic Attributes

336

336.00

611-172-7

1681

3018

DTXSID2032344

Colorless liquid

29201900

Characteristics

59.8

4.59

1.41 g/cm3 @ Temp: 20 °C

80 °C @ Press: 0.05 Torr

128℃

nD25 1.4980

Solubility in water, g/100ml at 20°C:

2-8°C

Vapour pressure, Pa at 20°C: 0.106

LD50 in rats, mice (mg/kg): 1-10, 20-50 orally; in rabbits (mg/kg): 20-200 dermally (Watkinson)

Safety Information

I

6.1(a)

2783

26/27/28-36-50/53

26-28-36/37-45-60-61

TF6150000

T+,N

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.

Stable at room temperature >18 months; stable at 55 deg C for 2 weeks neat, in 316 stainless steel and in 504 ppm Fe2O3.

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

USEPA/Office of Pesticide Programs; Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Chlorethoxyfos. EPA issues a TRED for a pesticide that requires tolerance reassessment decisions, but does not require a reregistration eligibility decision at present because: the pesticide was initially registered after November 1, 1984, and by law is not included within the scope of the reregistration program; EPA completed a RED for the pesticide before FQPA was enacted on August 3, 1996; or the pesticide is not registered for use in the U.S. but tolerances are established that allow crops treated with the pesticide to be imported from other countries.[Available from, as of July 24, 2003: http://www.epa.gov/pesticides/reregistration/status.htm]

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Safety glasses or goggles, rubber gloves, long -sleeved shirt, and long pants when handling product. Dusk mask or respirator when loading.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic/|If material on fire or involved in fire: Use water in flooding quantities as fog. Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) /Organophosphorus pesticides, solid, toxic/

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/

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organophosphorus pesticides, solid, toxic|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, toxic/|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, flammable, toxic/|Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. Avoid bodily contact with the material. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Organophosphorus pesticides, solid, toxic/|For more Preventive Measures (Complete) data for CHLORETHOXYFOS (8 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. 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 CHLORETHOXYFOS (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.

Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached.

Cholinesterase inhibition. The substance may cause effects on the nervous system. This may result in convulsions and respiratory depression. Exposure could cause death. The effects may be delayed. Medical observation is indicated.

Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms.

NO open flames.

STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

Toxicity

LD50 Mouse oral 20-50 mg/kg|LD50 Rabbit dermal 20-200 mg/kg|LD50 Rat (female) oral 1.8 mg/kg|LD50 Rat (male) oral 4.8 mg/kg|For more Non-Human Toxicity Values (Complete) data for CHLORETHOXYFOS (7 total), please visit the HSDB record page.

Chlorethoxyfos' 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).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 890(SRC), determined from a structure estimation method(2), indicates that chlorethoxyfos is expected to have low mobility in soil(SRC). Volatilization of chlorethoxyfos from moist soil surfaces is expected(SRC) given an estimated Henry's Law constant of 4.2X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3); however, volatilization may be attenuated by adsorption to soil(SRC). Chlorethoxyfos is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.95X10-4 mm Hg(4). Half-lives in soil at 25 °C of chlorethoxyfos in laboratory studies were 7 days in Handord sandy loam and 20 days in Flanagan loam(4). Field soil dissipation half-lives were reported in the range of 2-3 days(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 890(SRC), determined from a structure estimation method(2), indicates that chlorethoxyfos is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.2X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 10 hours and 9 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 680(SRC), from a log Kow of 4.59(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Half-lives for the hydrolysis of chlorethoxyfos are 4.3, 59, and 72 days at pH 5, 7, and 9, respectively6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorethoxyfos, which has a vapor pressure of 7.95X10-4 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chlorethoxyfos 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 4.2 hours(SRC), calculated from its rate constant of 9.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Chlorethoxyfos is not expected to absorb light with wavelengths >290 nm and is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of chlorethoxyfos with photochemically-produced hydroxyl radicals has been estimated as 9.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Half-lives for the hydrolysis of chlorethoxyfos are 4.3, 59, and 72 days at pH 5, 7, and 9, respectively(2). Chlorethoxyfos is not expected to absorb light with wavelengths >290 nm and is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 680 was calculated for chlorethoxyfos(SRC), using a log Kow of 4.59(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).

3.98e+03 L/kg|Using a structure estimation method based on molecular connectivity indices(1), the Koc for chlorethoxyfos can be estimated to be 890(SRC). According to a classification scheme(2), this estimated Koc value suggests that chlorethoxyfos is expected to have low mobility in soil.

The Henry's Law constant for chlorethoxyfos is estimated as 4.2X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that chlorethoxyfos is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 10 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 9 days(SRC). Chlorethoxyfos' Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization may be attenuated by adsorption to soil(SRC). Chlorethoxyfos is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.95X10-4 mm Hg(3).

Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/

Occupational exposure to chlorethoxyfos may occur through inhalation and dermal contact with this compound at workplaces where chlorethoxyfos is produced or used. (SRC)|Secondary exposure of children through contact with their parents' contaminated clothing can also occur. /Organophosphorus pesticides/

Drug Information

Most organophosphorus pesticides are not ionized and are very lipophilic. Thus, inhaled or swallowed material will be easily taken up. /Organophosphorus Pesticides/

Metabolism occurs principally by oxidation, hydrolysis by esterases, and by transfer of portions of the molecule to glutathione. Oxidation of organophosphorus insecticides may result in more or less toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products, that are, in most cases, of low toxicity. Hydrolytic and transferase reactions affect both the thioates and their oxons. /Organophosphorus Pesticides/|Major metabolites are CO2 and biosynthetic intermediates such as serine, glycine and glycine conjugates.

Organophosphorus insecticides exert their acute effects in both insects and mammals by inhibiting acetylcholinesterase (AChE) in the nervous system with subsequent accumulation of toxic levels of acetylcholine (ACh), which is a neurotransmitter. In many cases, the organophosphorylated enzyme is fairly stable, so that recovery from intoxication may be slow. /Organophosphorus Pesticides/

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


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


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

Airway protection. Ensure 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/|Atropine sulfate. Administer atropine sulfate intravenously, or intramuscularly if intravenous injection is not possible. Remember that atropine can be administered through an endotracheal tube if initial IV access if difficult to obtain. Depending on the severity of poisoning, doses of atropine ranging from very low to...high... . The objective of atropine antidotal therapy is to antagonize the effects of excessive concentrations of acetylcholine at end-organs having muscarinic receptors. Atropine does not reactivate the cholinesterase enzyme or accelerate disposition of organophosphate. Recrudescence of poisoning may occur if tissue concentrations of organophosphate remain high when the effect of atropine wears off. Atropine is effective against muscarinic manifestations, but it is ineffective against nicotinic actions, specifically muscle weakness and twitching, and respiratory depression. Despite the limitations, atropine is often a life-saving agent in organophosphate poisonings. Favorable response to a test dose of atropine can help differentiate poisoning by anticholinesterase agents from other conditions. However, lack of response, with no evidence of atropinization (atropine refractoriness) is typical of more severe poisonings. The adjunctive use of nebulized atropine has been reported to improve respiratory distress, decrease bronchial secretions, and increase oxygenation. ...Do not administer atropine or pralidoxime prophylactically to workers exposed to organophosphate pesticides. Prophylactic dosage with either atropine or pralidoxime may mask early signs and symptoms of organophosphate poisoning and thus allow the worker to continue exposure and possibly progress to more severe poisoning. Atropine itself may enhance the health hazards of the agricultural work setting: impaired heat loss due to reduced sweating and impaired ability to operate mechanical equipment due to blurred vision. This can be caused by mydriasis, one of the effects of atropine. /Organophosphate pesticides/|Glycopyrolate has been studied as an alternative to atropine and found to have similar outcomes using continuous infusion. Ampules of...glycopyrolate were added to...saline and this infusion was titrated to the desired effects of dry mucous membranes and heart rate above 60 beats/min. During this study, atropine was used as a bolus for a heart rate less than 60 beats/min. The other apparent advantage to this regimen was a decreased number of respiratory infections. This may represent an alternative when there is a concern for respiratory infection due to excessive and difficult to control secretions, and in the presence of altered level of consciousness where the distinction between atropine toxicity or relapse of organophosphate poisoning is unclear. /Organophosphate pesticides/|Pralidoxime. Before administration of pralidoxime, draw a blood sample (heparinized) for cholinesterase analysis (since pralidoxime tends to reverse the cholinesterase depression). Administration pralidoxime (Protopam, 2-PAM), a cholinesterase reactivator, in cases of severe poisoning by organophosphate pesticides in which respiratory depression, muscle weakness, and/or twitching are severe. When administered early (usually less than 48 hours after poisoning) pralidoxime relieves the nicotinic as well as the muscarinic effects of poisoning. Pralidoxime works by reactivating the cholinesterase and also by slowing the "aging" process of phosphorylated cholinesterase to a non-reactivatable form. ... Dosage of pralidoxime may be repeated in 1-2 hours, then at 10-12 hour intervals if needed. In very severe poisonings, dosage rates may be doubled. Repeated doses of pralidoxime are usually required. In cases that involve continuing absorption of organophosphate (as after ingestion of large amounts), or continuing transfer of highly lipophilic organophosphate from fat into blood, it may be necessary to continue administration of pralidoxime for several days beyond the 48 hour post-exposure interval usually cited as the limit of its effectiveness. ... Blood pressure should be monitored during administration because of the occasional occurrence of hypertensive crisis. Administration should be slowed or stopped if blood pressure rises to hazardous levels. Be prepared to assist pulmonary ventilation mechanically if respiration is depressed during or after pralidoxime administration. If intravenous injection is not possible, pralidoxime may be given by deep intramuscular injection. /Organophosphate pesticides/|For more Antidote and Emergency Treatment (Complete) data for CHLORETHOXYFOS (17 total), please visit the HSDB record page.

/HUMAN EXPOSURE STUDIES/ Signs and symptoms of acute intoxication by organophosphorus insecticides include muscarinic, nicotinic, and central nervous system (CNS) manifestations. Symptoms may develop rapidly, or there may be a delay of several hours after exposure before they become evident. The delay tends to be longer in the case of more lipophilic compounds, which also require metabolic activation. Symptoms may increase in severity for more than one day and may last for several days. In severe cases, respiratory failure is a dominant effect. /Organophosphorus pesticides/|/SIGNS AND SYMPTOMS/ Principal effects /of anticholinesterases as toxic components of insecticides/ on eye, whether from local contact or systemic poisoning, are miosis and spasm of accommodation for near vision. /Anticholinesterases/

The substance can be absorbed into the body in hazardous amounts by inhalation, through the skin and by ingestion.

Dizziness. Nausea. Sweating. Muscle twitching. Pupillary constriction, muscle cramp, excessive salivation. Laboured breathing. Convulsions. Unconsciousness.


MAY BE ABSORBED! See Inhalation.


Blurred vision.

Chlorethoxyfos Use and Manufacturing

Uses

Insecticide.

A technical grade, 88% a.i, and two granular end-use products, Fortress 2.5G (352-579) and 5G (352-552), 2.5% and 5% a.i. respectively.|Granules (2.5 g, 5g)|Tradename:'Fortress'

The WHO Recommended Classification of Pesticides by Hazard identifies Chlorethoxyfos (technical grade) as Class IA: extremely hazardous; Main Use: insecticide.

Agrochemicals -> Insecticides|Insecticides

Computed Properties

Molecular Weight:336.0
XLogP3:4.6
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:335.889113
Monoisotopic Mass:333.892063
Topological Polar Surface Area:59.8
Heavy Atom Count:15
Complexity:225
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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