Basic information
- Standard SMILES
CCOP(=S)(OCC)SCSP(=S)(OCC)OCC- InChIKey
RIZMRRKBZQXFOY-UHFFFAOYSA-N- Molecular formula
- C9H22O4P2S4
- Average molar mass
- 384.5 g/mol
- Monoisotopic mass
- 383.98761787
Names & identifiers
- Preferred name
- Ethion
- IUPAC
- diethoxyphosphinothioylsulfanylmethylsulfanyl-diethoxy-sulfanylidene-lambda5-phosphane
- English name
- Ethion
- Molecular formula
- C9H22O4P2S4
- Molecular weight
- 384.46
Names & synonyms
Show more names
Database identifiers
- CAS
563-12-2- PubChem CID
- 3286
- DTXSID
DTXSID2024086- ChEMBL
CHEMBL1713417- ChEBI
CHEBI:38663- UNII
- 2TI07NO12Y
- EC Number
- 209-242-3
- Nikkaji
- J3.297B
Properties
Computed structural properties
- XLogP
- 5.1
- Topological polar surface area
- 152 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 12
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 279
Experimental & physicochemical properties
LogP
log Kow = 5.073
5.073
Density
1.215 to 1.23 at 68 °F (EPA, 1998)
1.220 @ 20 °C/4 °C
Relative density (water = 1): 1.2
1.215-1.23
1.31 @ 20°C
1.22
Color/Form
Water-white to amber-colored liquid
Colorless to amber-colored liquid [Note: A solid below 10 degrees F].
Liquid
Solubility
0.0001 % (NIOSH, 2024)
Soluble in xylene, chloroform, acetone, kerosene, and 1% methyl ethyl ketone or benzene, and methylated naphthalene.
Sol in petroleum oils, most organic solvents
Sol in methyl alcohol and ethyl alcohol
MISCIBLE WITH AROMATICS
In water, 2.0 mg/l @ 25 °C
Flash Point
349 °F (NIOSH, 2024)
349 °F
349 °F
Boiling Point
Decomposes above 302.0 °F (USCG, 1999)
165 °C @ 0.3 mm Hg
BP: decomposes >150 °C
>302 °F (decomposes)
>302 °F (Decomposes)
Melting Point
9 to 10 °F (EPA, 1998)
-12 to -13 °C
-12 - -13 °C
9-10 °F
-13 °C
10 °F
Vapor Pressure
1.5e-06 mmHg at 77 °F (EPA, 1998)
0.0000015 [mmHg]
1.5X10-6 mm Hg @ 25 °C
Vapor pressure, Pa at 25 °C: 0.0002
0.0000015 mmHg
0.0000015 mmHg
Refractive Index
INDEX OF REFRACTION: 1.530-1.542 @ 20 °C/D /TECHNICAL GRADE/
Index of refraction: 1.5490 @ 20 °C/D
Physicochemical properties
- Melting point
- -13 to · -13 to -12°
- Boiling point
- 164 · 164~165℃ (0.3mmHg)
- Density
- 420 · d420 1.220
- vapor pressure
- 2 x · 2.0 x 10-4 Pa (25 °C)
- refractive index
- 20 · nD20 1.5490
- storage temp.
- 0 · 0-6°C
- solubility
- Chloroform (Slightly), DMSO (Slightly)
- Water Solubility
- 2 mg · 2 mg l-1 (25 °C)
- form
- liquid
- Merck
- 13 · 13,3772
- JECFA Number
- 85 · 85
- BRN
- 1804530 · 1804530
- Henry's Law Constant
- 2.6 · 2.6×101 mol/(m3Pa) at 25℃, HSDB (2015)
- Exposure limits
- 0.4 mg/m3; · NIOSH REL: TWA 0.4 mg/m3; ACGIH TLV: TWA 0.4 mg/m3.
- Major Application
- agricultureenvironmental
- InChI
- 1S/C9H22O4P2S4/c1-5-10-14(16,11-6-2)18-9-19-15(17,12-7-3)13-8-4/h5-9H2,1-4H3
- InChIKey
- RIZMRRKBZQXFOY-UHFFFAOYSA-N
- SMILES
- CCOP(=S)(OCC)SCSP(=S)(OCC)OCC
- EWG's Food Scores
- 4 · 4
- FDA UNII
- 2 TI07NO12Y · 2TI07NO12Y
- Pesticides Freedom of Information Act (FOIA)
- Ethion
- EPA Substance Registry System
- Ethion (563-12-2)
- Toxicological Profile|ATSDR
- ETHION|Toxicological Profile|ATSDR
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 6 · GHS06,GHS09
- Signal word
- Danger
- Hazard statements
- 301 · H301-H312-H410
- Precautionary statements
- 273 · P273-P280-P301+P310+P330-P302+P352+P312
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- T,N
- Risk Statements
- 21 · 21-25-50/53
- Safety Statements
- 25 · 25-36/37-45-60-61-23
- OEB
- C
- OEL
- 0.4 mg/m3 · TWA: 0.4 mg/m3 [skin]
- RIDADR
- 3018 · 3018
- WGK Germany
- 3 · 3
- RTECS
- 4550000 · TE4550000
- HazardClass
- 6.1 · 6.1(a)
- PackingGroup
- II
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 2 DermalAcute · Acute Tox. 2 DermalAcute Tox. 2 OralAquatic Acute 1Aquatic Chronic 1
- Hazardous Substances Data
- 563 · 563-12-2(Hazardous Substances Data)
- Toxicity
- 50 in · LD50 in female, male rats (mg/kg): 27, 65 orally; 62, 245 dermally (Gaines)
Safety & regulation
GHS classification
GHS Classification
Danger
H301: Toxic if swallowed [Danger Acute toxicity, oral];H312: Harmful in contact with skin [Warning Acute toxicity, dermal];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]
P264, P270, P273, P280, P301+P316, P302+P352, P317, P321, P330, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Danger
Hazard information
Regulatory Information
Hazard Traits - Developmental Toxicity; Neurotoxicity;Authoritative List - ATSDR Neurotoxicants; CECBP - Priority Chemicals; IRIS Neurotoxicants;Report - if used as a fragrance or flavor ingredient
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.)
Fire Hazards
Shock can shatter the container, releasing the contents. Fire may produce irritating or poisonous gases. Decomposes above 302F. When heated to decomposition it emits highly toxic fumes of oxides of sulfur and phosphorus. Hydrolyzed by acids and alkalies. Slowly oxidized in air. (EPA, 1998)
Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion if formulations contain flammable/explosive solvents.
Hazards Summary
Ethion is an organophosphate pesticide. Pure ethion is a clear to yellowish liquid with an unpleasant sulfur-like smell. It does not occur naturally in the environment. Ethion is used in agriculture, mainly to control insects on citrus trees, but also on cotton, fruit and nut trees, and some vegetables. It may also be used on lawns and turf grasses, but it is not used in the home for pest control.
Classified as moderately toxic; [EXTOXNET] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]
The major hazards encountered in the use and handling of ethion stem from its toxicologic properties as an organophosphate pesticide. Surface contact may cause burns to the skin and eyes. Systemic effects from skin absorption, ingestion, or inhalation of ethion range from headache, weakness, and disorientation, to convulsions, coma, and death from respiratory arrest. To guard against these effects, the ACGIH recommends a TLV of 0.4 mg/cu m air, with an additional notation that skin contact is to be avoided. For those at greatest risk of exposure (ie, manufacturers, formulators, and applicators of this near-colorless, disagreeably smelling insecticide) protection should be assured by wearing gloves, rubber boots, overalls made of tight fabric or polyvinyl chloride, and a respirator with an activated-carbon gas filter cartridge, or a self-contained breathing apparatus. Strict personal hygiene is equally important. Skin should be washed thoroughly with soap and water when contaminated by ethion and routinely after work. Likewise, protective clothing should be washed once a week and each time it is contaminated, as well as routinely removed before going home. Smoking and eating should be prohibited in ethion work areas. Use and handling of ethion should not be conducted by persons with diseases of the respiratory system, cardiovascular system, CNS, liver, kidney, or eyes. Protect from exposure, those under 18 yr of age, expectant or nursing mothers, and alcoholics. Ethion will not ignite easily, but it will burn with the possible evolution of irritating, or poisonous gases and fumes (oxides of sulfur and phosphorous). For small fires involving ethion, extinguish with dry chemical, CO2, water spray (solid streams may be ineffective), or foam, and for large fires, use water spray fog, or foam. Cool all affected containers with flooding quantities of water (cyllinders explode in the heat of a fire). Runoff from fire control water may give off poisonous gases or cause pollu
FIFRA Requirements
Tolerances are established for residues of insecticide ethion (O,O,O',O'-tetraethyl S,S'-methylene bisphosphorodithioate) including its oxygen analog (S-[[(diethoxyphosphinothioyl)thio]methyl]O,O-diethyl phosphorothioate) in or on the following raw agricultural commodities: cattle, fat; cattle, meat-by-products; cattle, meat (fat basis); citrus fruits; citrus pulp, dehydrated; goats, fat; goats, meat-by-products; goats, meat; hogs, fat; hogs, meat-by-products; hogs, meat; horses, fat; horses, meat-by-products; horses, meat; milk fat (reflecting (N) residues in milk; raisins; sheep, fat; sheep, meat-by-products); sheep, meat; and tea, dried.
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. Ethion 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 1988. Case No: 0090; Pesticide type: insecticide (acaracide); Registration Standard Date: 9/29/89; Case Status: Pre-Reregistration Eligibility Decision - 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 document.; Active ingredient (AI): ethion; Data Call-in (DCI) Date(s): 12/02/92; AI Status: Supported - The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
Reactivity Profile
Organothiophosphates, such as ETHION, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.
Safety & protection
Fire Fighting
Move containers from fire area if it can be done without risk. Dike fire control water for later disposal, do not scatter the material. Fight fire from maximum distance. Wear positive pressure breathing apparatus and protective clothing.;For small fires, use dry chemical, carbon dioxide, water spray, or foam. For large fires, use water spray, fog, or foam. (EPA, 1998)
Use water spray, alcohol-resistant foam, powder, carbon dioxide.
First Aid Measures
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.
Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .
First Aid
Warning: Effects may be delayed up to 12 hours. Caution is advised.;Note: Ethion is a cholinesterase inhibitor.;Signs and Symptoms of Ethion Exposure: Acute exposure to ethion 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 ethion 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 ethion.;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 ethion.;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.
(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.
Exposure Control and Personal Protection
Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]
Cleanup Methods
Spillages of pesticides at any stage of their storage or handling should be treated with great care. Liquid formulations may be reduced to solid phase by evaporation. Dry sweeping of solids is always hazardous: These should be removed by vacuum cleaning or by dissolving them in water or other solvent in the factory environment. /Pesticides/
Environmental considerations: Land spill: Dig a pit, pond, lagoon, or 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./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.
Environmental consideration: Water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
Emits toxic fumes of oxides of sulfur and phosphorus when heated to decomposition. /Ethion/
Nonfire Spill Response
Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:;ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Cover with plastic sheet to prevent spreading. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024)
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds.
Peer-review: Large amt, incinerate in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
Spillage Disposal
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. Do NOT wash away into sewer.
Preventive Measures
If material is 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.
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. ... If contact with the material anticipated, wear appropriate chemical protective clothing. ...
CONTAINERS ... SHOULD BE CLEANED WITH A SUSPENSION OF BLEACHING POWDER IN WATER OR WITH OTHER ALKALINE SOLN AFTER SOAKING FOR 24 HR AND THEN BE RINSED WITH HOT WATER. /ORGANOPHOSPHORUS PESTICIDES/
THE STRICT OBSERVANCE OF HYGIENE RULES- NO SMOKING AND NO FOOD INTAKE DURING WORK, THOROUGH WASHING WITH SOAP AFTER WORK, CHANGING PROTECTIVE CLOTHING BEFORE GOING HOME- IS OF THE UTMOST IMPORTANCE. /ORGANOPHOSPHORUS PESTICIDES/
For more Preventive Measures (Complete) data for ETHION (9 total), please visit the HSDB record page.
Toxicology
Treatment
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.
Target Organs
Neurological (Nervous System)
Nervous
Eyes, skin, respiratory system, central nervous system, cardiovascular system, blood cholinesterase
Health Effects
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
Ecotoxicity Values
LC50 Gammarus fasciatus 1.8 ug/l/96 hr @ 21 °C (95% confidence limit 1.3- 2.4 ug/l), mature /Technical material, 100% in a static bioassay/
LC50 Palaemonetes kadiakensis 5.6 ug/l/96 hr @ 15 °C (95% confidence limit 3.2-9.8 ug/l), mature /Technical material, 100% in a static bioassay/
LC50 Pteronarcys californica 2.8 ug/l/96 hr @ 15 °C (95% confidence limit 1.8-4.2 ug/l), second yr class /Technical material, 100% in a static bioassay/
LC50 Cutthroat trout 720 ug/l/96 hr @ 13 °C (95% confidence limit 580-900 ug/l), wt 1.2 g /Technical material, 100% in a static bioassay/
For more Ecotoxicity Values (Complete) data for ETHION (18 total), please visit the HSDB record page.
Environmental Fate
AQUATIC FATE: Degradation of ethion in irrigation canal waters draining a citrus grove in South Florida occurred readily by hydrolysis with a half-life of 26 days. The reaction was pH independent from pH 4-7 with a pseudo-1st-order rate constant of 4.8/days. Adsorption to canal sediments was negligible and desorption was rapid. Ethion did not accumulate in the sediment and water sample levels, never exceeded 0.017 mg/l in the water or 0.03 mug/g (dry wt) in the sediments. Hydrolysis may have been a significant mechanism in the loss of ethion from irrigation canal waters.
TERRESTRIAL FATE: Ethion, fonofos, fensulfothion, carbofuran, or chlorpyrifos were applied as a commercial granular formulations at rates equivalent to 2.24, 1.12, 1.12, 1.68, and 1.68 kg AI (active ingredient)/ha, respectively, to furrows in a greenhouse and subjected to 4 different watering schedules (normal, 0.5, 1.0, and 1.5 ml/sq cm). Persistence & movement were measured. Ethion moved slightly faster in the 2 wetter soils. Unretained water did not contain significant concn of pesticides. Plots were treated with insecticide & seeded with onions for 3 successive yr. Residue (ethion) in the soil after 3 yr was 7.6 ppm.
TERRESTRIAL FATE: Based on a classification scheme(6), an average Koc value of 15,435 measured in four different soils(1), indicates that ethion is expected to be immobile in soil(SRC). Volatilization of ethion from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.8X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.50X10-6 mm Hg(2), and water solubility, 2.0 mg/l(3). Ethion is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.50X10-6 mm Hg(2). The half-life of ethion in sterile sandy loam and organic soil was found to be greater than 24 weeks while the half-life in the nonsterile soils was 7-8 weeks(4). The half-life in red, black, and laterite soil was 9.0-15.5 days in the laboratory(5).
AQUATIC FATE: Based on a classification scheme(11), an average Koc value of 15,435 measured in four different soils(1), indicates that ethion is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 3.8X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.50X10-6 mm Hg(4), and water solubility, 2.0 mg/l(3). According to a classification scheme(5), an estimated BCF of 1600(SRC), from its log Kow of 5.073(10) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is very high. The half-life of ethion in both sterilized and unsterilized FL canal water was found to be 24-26 days over a 12-week observation period(7). Biodegradation of ethion in surface waters may occur. The rate of degradation of ethion in a natural marsh water and in sterilized marsh water was found to be the same over a 16-week observation period(8). However, 25% of an initial concn of 10 ug/l was lost after 2 weeks in a river die-away test(12). The hydrolysis half-life of ethion in buffered distilled water at 30 °C was experimentally determined to be 20.8 weeks between pH 4 and pH 7, 8.9 weeks at pH 8, and 1 day at pH 10(7). The hydrolysis half-lives of ethion at 25 °C were experimentally determined to be 99, 63, 58, 25, and 8.4 weeks at pHs 4.5, 5, 6, 7, and 8, respectively(9).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethion, which has a vapor pressure of 1.50X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase ethion 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 40 mins(SRC), calculated from its rate constant of 5.8X10-10 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). Particulate-phase ethion may be removed from the air by wet and dry deposition(SRC). In a hexane solvent, ethion does not absorb UV light above 260 nm(4) which suggests that direct photolysis will not occur(SRC). The photooxidation of a thin film of ethion exposed to artificial light of 300 nm has been observed(5).
Food Survey Values
... ETHION ... /HAS BEEN RECOVERED/ IN THE LOW-NANOGRAM RANGE FROM ... LETTUCE, MILK ... CHICKENS ...
This report presents the residues found in 12 infant and toddler market baskets collected in 12 major cities in 4 geographical areas from August 1976 through September 1977. The market baskets were also analyzed for 6 heavy metals: arsenic, lead, selenium, zinc, cadmium, and mercury. Results of recovery studies conducted with residue compounds of various types are also included in this report. Out of 117 infant composites tested, 2 were found to contain ethion. Out of 132 toddler food composites tested 2 were found to contain ethion at 0.001 ppm. Residues were found in fruit & fruit juices.
This report presents residues of pesticides and other chemicals found in the diet of the United States' young adult male. This report includes results of analyses for 25 market basket samples collected from August 1976 through September 1977 in 20 different cities throughout 4 geographical areas. In 300 food composites tested, ethion was found in 8 at a range of 0.002-0.260 ppm.
As part of the US FDA Total Diet Study (Market Basket Survey), ethion was detected in 19 of 324 adult food composites collected between Oct 1980 and March 1982 with positive detections in root vegetables (2 detections; concn trace to 0.001 ppm), garden fruits (3 detections; concn trace to 0.012 ppm), and fruits (14 detections; concn trace to 0.021 ppm)(1). As part of the US FDA Total Diet Study, ethion was detected in 4 of 240 adult food composites collected between Oct 1979 and Sept 1980 with positive detections in root vegetables (1 detection; 0.016 ppm) and fruits (3 detections; concn 0.001 to 0.003 ppm)(2) and in 5 of 240 adult food composites collected between Oct 1978 and Sept 1979 with positive detections in fruits and garden fruits (concn trace to 0.020 ppm)(3). Ethion was detected in fruit samples (concn of 2 ppb) collected between 1976 and 1978 as part of the pesticide residue monitoring of the total diet study in Canada(4). In 1991-1993, a study conducted in Belgium found 3.6 and 5.4% samples of oranges and lemons, respectively, to contain maximum ethion residues of 0.04 and 0.06 ppm, respectively(5). In Northwest Spain, 23 of 69 honey samples contained 1-8 ug/kg ethion with a mean of 3.0 ug/kg(6). In 1992-1993, a study conducted by the US FDA found 4 occurrences with a maximum of 0.03 ppm ethion in domestic pears and none in imported, and 2 and 10 occurrences with a maximum of 0.21 and 0.09 ppm ethion in domestic and imported tomatoes, respectively(7). In 1994-1995, ethion was found in 5 out of 22 satsuma oranges, 18 of 62 clementines, 2 of 5 white grapefruits, and 12 of 26 primofiori lemons with residues ranging 0-0.5, 0.3-0.6, 5.30-5.60, and 0.3-0.5 mg/kg in Valencian, Spain(8). A study was conducted in Canada in 1992-1994 using 5784 domestic and 15,184 agricultural commodities; ethion was found in domestic and imported agricultural commodities with 11, 6, 3, 0, 0, and 0, and 28, 44, 66, 12, 5, and 0 occurrences, respectively, at concns of <0.05, 0.10,
Exposure Routes
The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
inhalation, skin absorption, ingestion, skin and/or eye contact
Oral (L1191) ; inhalation (L1191) ; dermal (L1191)
Toxicity Summary
Ethion is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
Animal Concentrations
... ETHION ... /HAS BEEN RECOVERED/ IN THE LOW-NANOGRAM RANGE FROM ... BEES & URINE.
Ethion recovery rates from chickens collected from supermarkets and grocery stores in Coimbra, Portugal were 82.42 and 94.70% of 39.6 and 78.6 ug/kg, respectively, in muscle, and 91.22 and 92.66% of 100 and 195.7 ug/kg, respectively, in skin(1).
Regulatory information
Regulatory Information
Hazard Traits - Developmental Toxicity; Neurotoxicity;Authoritative List - ATSDR Neurotoxicants; CECBP - Priority Chemicals; IRIS Neurotoxicants;Report - if used as a fragrance or flavor ingredient
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.)
FIFRA Requirements
Tolerances are established for residues of insecticide ethion (O,O,O',O'-tetraethyl S,S'-methylene bisphosphorodithioate) including its oxygen analog (S-[[(diethoxyphosphinothioyl)thio]methyl]O,O-diethyl phosphorothioate) in or on the following raw agricultural commodities: cattle, fat; cattle, meat-by-products; cattle, meat (fat basis); citrus fruits; citrus pulp, dehydrated; goats, fat; goats, meat-by-products; goats, meat; hogs, fat; hogs, meat-by-products; hogs, meat; horses, fat; horses, meat-by-products; horses, meat; milk fat (reflecting (N) residues in milk; raisins; sheep, fat; sheep, meat-by-products); sheep, meat; and tea, dried.
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. Ethion 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 1988. Case No: 0090; Pesticide type: insecticide (acaracide); Registration Standard Date: 9/29/89; Case Status: Pre-Reregistration Eligibility Decision - 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 document.; Active ingredient (AI): ethion; Data Call-in (DCI) Date(s): 12/02/92; AI Status: Supported - The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
CERCLA Reportable Quantities
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. Ethion is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 lbs.
Clean Water Act Requirements
Ethion is 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. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.
State Drinking Water Guidelines
(CA) CALIFORNIA 4 ug/l
(FL) FLORIDA 3.5 ug/l
Safety data
- OEB
- C
- OEL
- TWA: 0.4 mg/m3 [skin]
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- rtecs
- TE4550000
- ridadr
- 3018
- Toxicity
- LD50 in female, male rats (mg/kg): 27, 65 orally; 62, 245 dermally (Gaines)
- risk_code
- 21-25-50/53
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS09
- hazard_code
- T,N
- safety_code
- 25-36/37-45-60-61-23
- hazard_class
- 6.1(a)
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- Hazard statements
- H301-H312-H410
- Hazard Classifications
- Acute Tox. 2 DermalAcute Tox. 2 OralAquatic Acute 1Aquatic Chronic 1
- Precautionary statements
- P273-P280-P301+P310+P330-P302+P352+P312
- Hazardous Substances Data
- 563-12-2(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Mechanism of Action
The main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase, which plays an important physiological part. Organophosphorus pesticides can also indirectly interact with the biochemical receptors of acetylcholine. /Organophosphorus pesticides/
Non-systemic acaricide and insecticide with predominantly contact action. Cholinesterase inhibitor.
Ethion is a choloinesterase-inhibiting organophosphate ester and behaves like other organophosphate compounds possessing a similar degree of biologic activity.
Metabolism/Metabolites
Presumably /metabolized/ by oxidation to the thiol phosphate, dealkylation, and hydrolysis.
Metabolised in animals by oxidation to a phosphorothioate, followed by dealkylation nd hydrolysis.
Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately 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. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.
Absorption, Distribution and Excretion
ABSORPTION CAN OCCUR THROUGH ALL PORTALS, INCLUDING INTACT SKIN.
/THEY/ ... ARE RAPIDLY ABSORBED THROUGH MUCOUS MEMBRANE OF DIGESTIVE SYSTEM, RESPIRATORY SYSTEM & THE SKIN, & CONVEYED BY THE BLOOD TO VARIOUS BODY TISSUES. ... THE MAIN ROUTE OF ELIMINATION ... /IS/ THE KIDNEYS. /ORGANOPHOSPHORUS PESTICIDES/
Using published human data on skin-to-urine transfer of 12 insecticides and herbicides (azodrin, ethion, guthion, malathion, parathion, baygon, carbaryl, aldrin, dieldrin, lindane, 2,4-D, diquat), the skin-to-blood transfer rates for each compound were estimated by two numerical deconvolution techniques. Regular constrained deconvolution produced an estimated upper limit on cumulative dermal absorption of the radiolabel, while minimized deconvolution produced an upper bound on cumulative dermal absorption of parent compound. Dermal absorption rate was largest within 8 hours of dosing for all pesticides. Only carbaryl showed a lag (3.5 hr) in penetration. This may have indicated a prolonged transit time through skin or that a chemical transformation in skin had occurred. After onset, absorption occurred rapidly with 45% of the 120 hr cumulative absorption occurring in 8 hr. For parathion and dieldrin, > 50% of the 120 hr total absorption occurred in the first 4 hr. The deconvolution technique was used to calculate the temporal aspect of dermal absorption for linear systems.
Uses & manufacturing
Uses
Used on greenhouse crops, lawns, turf, and citrus and apple crops; also used on cattle and dormant trees; [EXTOXNET]
Farming (Pesticides) [Category: Industry]
For Ethion (USEPA/OPP PC Code 058401) active products with label matches./SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state, and local authorities must be consulted for curently approved uses./
INSECTICIDE AND ACARICIDE FOR CITRUS FRUIT, APPLES, NUTS, OTHER FRUIT, & COTTON. /FORMER USE/
/It is used/ for control of aphids, mites (including eriophyd mites), scales, thrips, leafhoppers, maggots, and foliar feeding larvae and on a wide variety of food, fiber, and ornamental crops. /Former use/
Ethion is a non-systemic insecticide and acaricide.
Impurities
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/
Consumption Patterns
Applied to melons, 50.1%; Tree fruits, 2.6%; Citrus, 12.8%; Grapes, 4.5%; Other vegetables, nuts, and fruits account for remainder (1984) /California use, calculated from table/
(1984) 4.68X10+7 g /used in California/
(1984) 4.68X10+7 g /used in California/
Methods of Manufacturing
REACTION OF METHYLENE BROMIDE & THE SODIUM SALT OF O,O-DIETHYLPHOSPHORODITHIOATE
/IT IS MADE/ BY INTERACTION OF DIBROMOMETHANE WITH O,O-DIETHYL HYDROGEN PHOSPHORODITHIOATE IN ETHANOL AT CONTROLLED PH. CANADIAN PATENT 845,731 & 851,217.
Willard, Henahan, US patents 2,873,228 and 3,014,058 (1959, 1961 to FMC)
O,O-Diethyl dithiophosphoric acid + formaldehyde (carbonyl addition)
Formulations/Preparations
USEPA/OPP PC Code 058401; Trade Names: Nialate, Embathion, Ethodan, ENT 24105, Fosfatox E, Fosfono 50, FMC 1240, Hylemox, Itopaz, Kwit, NIA 1240.
ETHION 4 DUST; ETHION 3 DUST; ETHION 2 DUST ... ETHION 0.67 LB/GAL OIL (FOR SUMMER USE).
WP; EC; DP; GR; Seed treatment
Mixtures include ethion + oils; ethion + dicofol; ethion + dicofol + parathion-methyl
For more Formulations/Preparations (Complete) data for ETHION (16 total), please visit the HSDB record page.
Use Classification
Chemical Classes -> Organophosphates and carbamates
Veterinary Drug -> INSECTICIDE; Veterinary Drug -> -> JECFA Functional Classes
INSECTICIDES
Applications
DescriptionEthion is a colorless to amber-colored, odorEthion is a colorless to amber-colored, odorless liquid. The technical product has a very disagreeableodor; Freezing/Melting point =-13 to -12℃. Molecularweight = 384.49; Boiling point = 164℃; Vaporpressure = 0.0000015 mmHg at 20℃; Flash point = 176℃.Hazard Identification (based on NFPA-704 M RatingSystem): Health 3, Flammability 1, Reactivity 0. Practicallyinsoluble in water; solubility = 0.0001%.
UsesEthion is used to control mites and sucking insects, larval Lepidoptera and soil pests in a wide range of crops and in turf. An additional use is as an ectoparasiticide to control cattle ticks.
UsesInsecticide; acaricide.
UsesIt is used as a pesticide.
UsesNonsystemic insecticide and acaricide used on apples.
General DescriptionTechnical ethion is an odourless amber liquid. It is very sparingly soluble in water but soluble in most of the organic solvents. Ethion undergoes decomposition on heating or on burning and produces toxic and corrosive fumes including phosphorus oxides and sulphur oxides. It is used for the control of crop pests and household insects. It may be used on a wide variety of food, fibre, and ornamental crops, including greenhouse crops, lawns, and turf.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: An organic thiophosphate that is S,S'-methanediyl bis[dihydrogen (phosphorodithioate)] in which all the hydroxy groups have been converted to their corresponding ethyl esters respectively. Ethion is an organophosphate insecticide with inhibitory activity t wards the enzyme acetylcholinesterase ( EC 3.1.1.7).
Related reactions
Linked notes
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