Ethoprophos

Ethoprophos Basic information
Product Name:Ethoprophos
Synonyms:phosphorodithioicacid,o-ethyls,s-dipropylester;phosphorodithioicacido-ethyls,s-dipropylester;Rovokil;S,S-Dipropyl O-ethyl phosphorodithioate;v-c 9-104;V-C Chemical V-C 9-104;v-c9-104;vc9-104
CAS:13194-48-4
MF:C8H19O2PS2
MW:242.34
EINECS:236-152-1
Product Categories:
Mol File:13194-48-4.mol
Ethoprophos Structure
Ethoprophos Chemical Properties
Melting point -13 °C
Boiling point 86-91°C
density d420 1.094
vapor pressure 4.65 x 10-2 Pa (26 °C)
Fp 100 °C
storage temp. APPROX 4°C
solubility DMF: 5mg/mL; DMSO: 5mg/mL; Ethanol: 1.6mg/mL
Water Solubility 700 mg l-1 (20 °C)
form neat
Merck 13,3782
BRN 8139788
Stability:Hygroscopic
CAS DataBase Reference13194-48-4(CAS DataBase Reference)
NIST Chemistry ReferenceEthoprophos(13194-48-4)
EPA Substance Registry SystemEthoprop (13194-48-4)
Safety Information
Hazard Codes T+;N,N,T+
Risk Statements 25-26/27-43-50/53
Safety Statements 27-28-36/37/39-45-60-61-27/28
RIDADR UN 2810
WGK Germany 3
RTECS TE4025000
HazardClass 6.1(a)
PackingGroup II
HS Code 29309090
Hazardous Substances Data13194-48-4(Hazardous Substances Data)
ToxicityLC50 (96-hour) for rainbow trout 13.8 mg/L, bluegill sunfish 2.1 mg/L and goldfish 13.6 mg/L (Hartley and Kidd, 1987); acute oral LD50 for rats 262 mg/kg (Hartley and Kidd, 1987), 34 mg/kg (RTECS, 1985).
MSDS Information
Ethoprophos Usage And Synthesis
DescriptionIntroduced in the 1960s, ethoprop is a nonsystemic insecticide/nematicide. The mobility of ethoprop in soil and its half-life are strongly dependent on soil organic matter (21). It is not known to be carcinogenic and is available as granules or emulsifiable concentrates.
Chemical PropertiesClear Colorless Oil
Chemical PropertiesEthoprophos is a pale yellow liquid.
UsesNonsystemic, nonfumigant nematocide and soil insecticide for control of insects in ornamentals, potatoes, sweet potatoes, tomatoes, strawberries, bananas, pineapples, sugar cane, turf and many other crops.
UsesInsecticide; nematocide.
UsesEthoprophos is used to control plant parasitic nematodes and soil insects.
UsesEthoprophos is an organophosphate non-systemic nematicide and soil insecticide. Ethoprophos is an acetylcholinesterase (AChE) inhibitor.
DefinitionChEBI: Ethoprophos is an organic thiophosphate and an organothiophosphate insecticide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an agrochemical and an antinematodal drug.
General DescriptionEthorop is one of a family of organophosphorus pesticides. Mocap is combustible though Mocap may require some effort to ignite. Mocap is very toxic by skin absorption and inhalation. Mocap may or may not be water soluble.
Air & Water ReactionsHydrolyzed in alkali.
Reactivity ProfileOrganothiophosphates, such as Mocap, 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.
Health HazardMocap is extremely toxic; the probable oral lethal dose for humans is 5-50 mg/kg, or between 7 drops and 1 teaspoonful for a 150 lb. person. It is a cholinesterase inhibitor which affects the nervous system.
Fire Hazard(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) Container may explode in heat of fire. Fire and runoff from fire control water may produce irritating or poisonous gases. Stable in water. Hydrolyzed in alkali.
Agricultural UsesNematicide, Insecticide: Ethoprop is used as a pre-plant soil application to control wireworms and nematodes in potatoes, sugar cane, sweet potatoes, and tobacco, with lesser usage on corn (field and sweet), beans (lima and snap), cucumbers, and cabbage. In addition, it is used to treat pineapples, bananas, and plantains, as well as fieldgrown ornamentals and non-bearing citrus trees, and commercial turf. Roughly 60% of ethoprop is applied to potatoes.
Trade nameAI3-27318®; CASWELL No. 434C®; JOLT®[C]; MENAP®; MOBIL V-C 9-104®; MOCAP®[C]; MOCAP 10G®[C]; PHOSETHOPROP®; ROVOKIL®; V-C 9-104®[C]; V-C CHEMICAL V-C 9-104®[C]; VIRGINIA-CAROLINA VC 9-104®
Safety ProfilePoison by ingestion and skin contact. A cholinesterase inhibitor type of insecticide. When heated to decomposition it emits very toxic fumes of POx and SOx. See also PARATHION.
Potential ExposureA potential danger to those involved in the manufacture, formulation and application of this nematocide and soil insecticide
CarcinogenicityIn a combined chronic feeding/ carcinogenicity study, when rats were fed diets with 0, 1, 10, or 100 ppm ethoprop in the diet for 24 months (equivalent to 0, 0.041, 0.40, or 4.19 mg/kg/day (males); 0, 0.052, 0.51, or 5.12 mg/kg/day (females)), adrenal gland malignant pheochromocytomas were increased in males and thyroid C-cell carcinomas were increased slightly in males . When ethoprop was administered in the diet to mice for 104 weeks at 0, 0.2, 2.0, or 30 ppm (males: 0, 0.026, 0.254, or 3.96 mg/ kg/day; females: 0, 0.032, 0.318, or 4.9 mg/kg/day), survival was unaffected at any dose level and no statistically significant dose-related incidence of tumors were seen in males or females.
Environmental FateSoil. The reported half-life in humus-containing soil (pH 4.5) and a sandy loam (pH 7.2–7.3) are 87 and 14–28 days, respectively (Hartley and Kidd, 1987). The rate of degradation increased in soils that had been treated annually four times (Smelt et al., 1987).
Chemical/Physical. Emits toxic fumes of phosphorus and sulfur oxides when heated to decomposition (Sax and Lewis, 1987).
Metabolic pathwayEthoprophos is a soil-acting insecticide and nematicide which is generally incorporated into the soil in the form of a granular formulation. Volatilisation is a factor involved in the loss and movement of the compound in the environment. The major route of degradation of ethoprophos in both plants and mammals is via hydrolysis to give O-ethyl S-propyl phosphorothioate through loss of propanethiol. Propanethiol has been shown to react as a nucleophile to yield ethyl propyl sulfide through attack on the phosphorus atom and dipropyl disulfide through attack on the sulfur atom of ethoprophos. The sulfide metabolites are further metabolised via oxidation to sulfoxides and sulfones. In mammals, an additional important route of detoxification is through de-ethylation via glutathione- S-alkyl transferase, a route common to many organophosphorus insecticides.
ShippingUN3018 Organophosphorus pesticides, liquid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required
DegradationEthoprophos is very stable in neutral and weakly acidic media but it is hydrolysed rapidly in alkaline solutions (PM). The DT50 of ethoprophos in 0.05M NaOH solution at 25 °C was 35 min and the hydrolysis product was identified as O-ethyl S-propyl phosphorothioate (2), indicating the greater susceptibility of the P-S bond to hydrolysis over the P-O bond. There was no measurable hydrolysis in 0.1M HCl after 1 hour (Menzer et al., 1971). The route of the base-catalysed hydrolysis of ethoprophos is shown in Scheme 1.
IncompatibilitiesIncompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides. Strong oxidizers may cause release of toxic phosphorus oxides. Organophosphates, in the presence of strong reducing agents such as hydrides, may form highly toxic and flammable phosphine gas. Keep away from alkaline materials
Waste DisposalIn accordance with 40CFR 165 recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office
Ethoprophos phosphate ester starch Ethanol Vamidothion Ethyl propionate CADUSAFOS Propyl disulfide Ethylparaben O,S,S-trimethyl phosphorodithioate O,S,S-Tripropyl dithiophosphate ISOXADIFEN-ETHYL 2-Ethoxyethanol Diethyl ether Fenamiphos Ethyl acetate BANOL Clindamycin phosphate SULPHOSUCCINIC ACID ESTER

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