Description
Introduced 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 Properties
Clear Colorless Oil
Chemical Properties
Ethoprophos is a pale yellow liquid.
Uses
Nonsystemic, 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.
Uses
Ethoprophos is used to control plant parasitic nematodes and soil
insects.
Uses
Insecticide; nematocide.
Uses
Ethoprophos is an organophosphate non-systemic nematicide and soil insecticide. Ethoprophos is an acetylcholinesterase (AChE) inhibitor.
Definition
ChEBI: 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.
Production Methods
Ethoprophos is commercially produced through organophosphorus synthesis, typically starting with phosphorus trichloride or phosphoryl chloride. These are reacted with two equivalents of n-propylmercaptan and one equivalent of sodium ethoxide to form ethoxy-bis(propylsulfanyl)phosphane. This intermediate is then oxidised, commonly using hydrogen peroxide, to yield the active compound, ethoprophos.
General Description
Ethorop 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 Reactions
Hydrolyzed in alkali.
Reactivity Profile
Organothiophosphates, 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 Hazard
Mocap 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 Uses
Nematicide, 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 name
AI3-27318®; 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®
Mechanism of action
Non-systemic with contact action. Acetylcholinesterase (AChE) inhibitor.
Safety Profile
Poison 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 Exposure
A potential danger to those involved
in the manufacture, formulation and application of this
nematocide and soil insecticide
First aid
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Speed in removing material from skinis of extreme importance. Shampoo hair promptly if contaminated. Seek medical attention immediately. If this chemicalhas been inhaled, remove from exposure, begin rescuebreathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart actionhas stopped. Transfer promptly to a medical facility. Whenthis chemical has been swallowed, get medical attention.Give large quantities of water and induce vomiting. Do notmake an unconscious person vomit. Remove and isolatecontaminated clothing and shoes at the site. Keep victimquiet and maintain normal body temperature. Effects may bedelayed; keep victim under observation
Carcinogenicity
In 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 Fate
Soil. 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 pathway
Ethoprophos 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.
storage
Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, well-ventilated area. Where possible, automatically pump liquidfrom drums or other storage containers to processcontainers.
Shipping
UN3018 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
Degradation
Ethoprophos is very stable in neutral and weakly acidic media but it is
hydrolysed rapidly in alkaline solutions (PM). The DT
50 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.
Incompatibilities
Incompatible 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 Disposal
In 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
Pesticide Type
Insecticide; Nematicide
