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  • Ethoprop
Name:Ethoprop
CAS No:13194-48-4

PRODUCT DESCRIPTION

【Name】
Ethoprop (Phosphorodithioic acid O-ethyl S,S-dipropyl ester)
【Iupac name】
1-[ethoxy(propylsulfanyl)phosphoryl]sulfanylpropane
【CAS Registry number】
13194-48-4
【Synonyms】
Ethylpropyl phosphorodithioate ((EtO)(PrS)2PO) (7CI)
ENT 27318
Ethoprop
Ethoprophos
Mobile
Mocap
Mocap 10G
Mocap 6EC
O-Ethyl S,S-dipropyl dithiophosphate
O-Ethyl S,S-dipropylphosphorodithioate
Profos
Prophos
Prophos (ester)
Rovokil
S,S-DipropylO-ethyl phosphorodithioate
VC 9-104
【EINECS(EC#)】
236-152-1
【Molecular Formula】
C8H19 O2 P S2 (Products with the same molecular formula)
【Molecular Weight】
242.339
【Inchi】
InChI=1S/C8H19O2PS2/c1-4-7-12-11(9,10-6-3)13-8-5-2/h4-8H2,1-3H3
【InChIKey】
VJYFKVYYMZPMAB-UHFFFAOYSA-N
【Canonical SMILES】
CCCSP(=O)(OCC)SCCC
【MOL File】
13194-48-4.mol

Chemical and Physical Properties

【Density】
1.106g/cm3
【Melting Point】
-13 deg C
【Boiling Point】
86-91℃
【Vapour】
0.00111mmHg at 25°C
【Refractive Index】
1.493
【Flash Point】
100?°C
【Solubilities】
Readily sol in most organic solvents
SOLUBLE IN KEROSENE
Solubility >300 g/kg @ 20 deg C in acetone, ethanol, xylene, 1,2-dichloroethane, diethyl ether, ethyl acetate, petroleum spirit, cyclohexane
In water, 750 mg/l @ 20-25 deg C
【Color/Form】
Pale yellow liquid
Pale yellow oil
【Storage temp】
APPROX 4°C
【Spectral properties】
Intense mass spectral peaks: 158 m/z (100%), 43 m/z (85%), 97 m/z (73%), 139 m/z (58%)
【Computed Properties】
Molecular Weight:242.339021 [g/mol]
Molecular Formula:C8H19O2PS2
XLogP3:3.6
H-Bond Donor:0
H-Bond Acceptor:4
Rotatable Bond Count:8
Exact Mass:242.056408
MonoIsotopic Mass:242.056408
Topological Polar Surface Area:76.9
Heavy Atom Count:13
Formal Charge:0
Complexity:152
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Hydrophobe Count:2
Effective Rotor Count:8
Conformer Sampling RMSD:0.8
CID Conformer Count:191

Safety and Handling

【Hazard Codes】
T+:Verytoxic;N:Dangerousfortheenvironment;
【Risk Statements】
R25;R26/27;R43;R50/53
【Safety Statements 】
S27;S28;S36/37/39;S45;S60;S61
【HazardClass】
6.1(a)
【PackingGroup 】
II
【Cleanup Methods】
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/
【Transport】
UN 2810
【Fire Fighting Procedures】
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/
【Formulations/Preparations】
AVAILABLE AS AN EMULSIFIABLE CONCENTRATE AT 4 LB/US GAL (US) & 10% GRANULAR FORMULATION.
'MOCAP', GRANULES (100 G AI/KG); EMULSIFIABLE CONCENTRATE (700 G/L).
MOCAP PLUS 4-2 EC (WITH DISYSTON).
Aventis CropScience has registrations for technical grades (95.9% and 94.4% active ingredient (ai)), emulsifiable concentrates (EC) (one product is solely ethoprop at 69.6% ai and the other is 46% ethoprop and 23% disulfoton), granulars (3% [one product, which is a multiple ai with 10% pentachloronitrobenzene (PCNB)], 10% [one product is solely ethoprop and other products are multiple ai, one with 8.8% phorate and the other 5.6% disulfoton], 15%, and 20% ai), and a gel in water-soluble packaging (68.2% ai). Micro- Flo Co. has a registration for a granular (3% ai as a multiple ai with 10% PCNB). Note that Aventis has indicated that their gel formulation and multiple ai products (with disulfoton, phorate, and PCNB) are not currently marketed, and has requested voluntary cancellation of these products.
'Rhocap' (Aventis); 'Vimoca' (Vipesco) mixtures: 'Holdem' (+ phorate) (Aventis); ...Discontinued names: 'Prophos' * (Rhone-Poulenc).
【DOT Emergency Guidelines】
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /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: CAUTION: All these products have a very low flash point. Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or alcohol-resistant foam. Large fires: Water spray, fog or alcohol-resistant foam. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Use water spray or fog; do not use straight streams. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. /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/ Spill or Leak: Fully encapsulating, vapor protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor suppressing foam may be used to reduce vapors. Small spills: Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces. /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/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. Keep victim warm and quiet. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic; Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic; Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic; Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ 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, solid, poisonous; Organophosphorus pesticide, solid, toxic; Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic; Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire: Small fires: Dry chemical, CO2 or water spray. Large fires: Water spray, fog or regular foam. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Use water spray; do not use straight streams. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. /Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic; Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in 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. /Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic; Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic; Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic/
【Reactivities and Incompatibilities】
Incompatible with alkaline materials.
【Other Preventative Measures】
Do not contaminate water, food, feed by storage or disposal.
Avoid contact with skin and eyes and inhalation of fumes and dust.
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/
Personnel protection: Avoid breathing vapors. 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, liquid, toxic/
Personnel protection: Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment. /Organophosphorus pesticides, liquid, flammable, toxic/
The protective clothing should be kept in separate places where it cannot be contaminated with toxic chemicals. It should be forbidden to keep this clothing in living quarters. Protective clothing must be washed at least once a week and each time it is contaminated with pesticides. Before washing the clothing should be soaked for several hours in a calcium carbonate solution. /Pesticides/
Smoking, eating, and drinking before washing should be absolutely prohibited when any pesticide ... is being handled or used. /Pesticides/
【Octanol/Water Partition Coefficient】
log Kow = 3.59 @ 21 deg C
【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

REACTION OF S,S-DIPROPYL O-ETHYL PHOSPHORODITHIOITE AND HYDROGEN PEROXIDE
U.S. Production

(1972) 2.58-4.54X10+8 GRAMS (EST)
(1974) 5X10+8 GRAMS (EST)
Consumption Patterns

55% AS AN INSECTICIDE & NEMATOCIDE ON CORN, PEANUTS, SUGARCANE, SWEET POTATOES, & SEEDLINGS; 45% AS AN INSECTICIDE & NEMATOCIDE ON TOBACCO (1974)

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
In a metabolism study, ethoprop was administered to Crl:CD(SD)BR rats as a single IV bolus (males and females); single oral bolus (females, metabolism and pharmacokinetic studies; males, metabolism only); or by multiple oral doses. Following oral administration, ethoprop was completely absorbed and completely metabolized. Excretion was by urinary (>50% administered dose), fecal (7-16%), and respiratory (11-19%) routes and was essentially complete by 48 hours.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values in the range of 70-120(2-4), indicate that ethoprop is expected to have high mobility in soil(SRC). Volatilization of ethoprop from moist soil surfaces is not expected to be an important fate process(SRC), given a Henry's Law constant of 1.62X10-7 atm-cu m/mole(SRC), derived from ethoprop's vapor pressure, 0.00038 mm Hg(2) and water solubility, 750 mg/l(2). Ethoprop is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). However, under laboratory conditions, volatilization of ethoprop residue after 12 hours was reported as 1.4-3.6, 2.3-4.5, and 6.5-20.2% from sandy loam soil with 1, 10 and 20 % moisture levels, respectively(7). The US Department of Agriculture's Pesticide Properties Database lists a soil half-life of 25 days for ethoprop(2), but half-lives may range from 3-56 days(4). Due to microbial adaptation, ethoprop degrades more rapidly in soils that have had prior exposure to ethoprop(5,6). Half-lives for photolysis of ethoprop in soil in the sunlight and shade were 4.7 and 12.3 days, respectively(7).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 70-120(2-3), indicate that ethoprop is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 1.62X10-7 atm-cu m/mole(SRC), derived from a vapor pressure of 0.00038 mm Hg(2) and water solubility 750 mg/l(2). According to a classification scheme(5), BCFs ranging from 4-17(6) suggest the potential for bioconcentration in aquatic organisms is low(SRC). Ethoprop is very stable in neutral and weakly acidic media, but is rapidly hydrolyzed in alkaline media(7). The major degradation pathway for ethoprop under both aerobic and anaerobic conditions is hydrolysis to O-ethyl-S-propyl-phosphorothioic acid(8). The hydrolytic half-lives of ethoprop in distilled, river, brackish and open sea water were 25, 133, 65, and 81 days, respectively(9). Half-lives of 75 and 90 days have been found in sand sediment/water and silt loam sediment/water systems(10).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethoprop, which has a vapor pressure of 0.00038 mm Hg at 20-25 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethoprop 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 5.6 hours(SRC), calculated from its rate constant of 6.9X10-11 cu cm/molecule-sec at 25 deg C(SRC), that was derived using a structure estimation method(3). While ethoprop was found to undergo photolysis on soil(4), no data were found regarding photolysis by sunlight in air(SRC).

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