298-04-4 Usage
Description
DISULFOTON, an organic thiophosphate, is the diethyl ester of S-[2-(ethylsulfanyl)ethyl] dihydrogen phosphorodithioate. It is a dark yellowish oil with an aromatic, sulfurous odor and is soluble in most organic solvents and fatty oils. DISULFOTON is a selective, systemic insecticide and acaricide.
Uses
Used in Agriculture:
DISULFOTON is used as a systemic insecticide and acaricide for the control of sucking insects and mites in a wide range of crops. It is particularly effective against aphids, leafhoppers, thrips, beet flies, spider mites, and coffee leaf miners. DISULFOTON has been extensively used in pest control on crops such as cotton, tobacco, sugar beets, corn, peanuts, wheat, ornamentals, cereal grains, and potatoes.
Used in Seed Coating and Soil Application:
DISULFOTON is used for seed coating and soil application to protect crops from insect attacks. It is a selective, systemic organophosphate insecticide and acaricide that is especially effective against sucking insects.
Restricted Use Pesticides (RUP):
All products formulated at greater than 2% DISULFOTON are classified as Restricted Use Pesticides (RUP). This classification is due to the potential risks associated with its use, and it is not approved for use in EU countries. There are 21 global suppliers for DISULFOTON. Human exposures to DISULFOTON can occur through breathing contaminated air, drinking contaminated water, eating contaminated food, and working in industries that manufacture and formulate the pesticide.
Reactivity Profile
Organothiophosphates, such as DISULFOTON, 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
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.
Health Hazard
Disulfoton is highly toxic to animals and humans by all routes of exposures, namely, by
dermal absorption, through ingestion, and inhalation by the respiratory route. The symptoms
of poisoning include blurred vision, fatigue, headache, dizziness, sweating, tearing,
and salivation. It inhibits cholinesterase and affects the nervous system function. It does
not cause delayed neurotoxicity. Prolonged period of exposures to high concentrations of
disulfoton cause harmful effects to the nervous system with symptoms such as narrowing
of the pupils, vomiting, diarrhea, drooling, diffi culty in breathing, lung edema, tremors,
convulsions, coma, and death. Disulfoton causes no mutagenic or teratogenic effects in
laboratory animals. There are no reports indicating that disulfoton causes cancer in animals
or humans. The DHHS, the IARC, and the US EPA have not classifi ed disulfoton as
to its ability to cause cancer.
Fire Hazard
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.
Trade name
BAY 19639?; BAYER 19639?;
DIMAZ?; DISULFATON?; DI-SYSTON?[C];
DISYSTON?[C]; DISYSTOX?; DITHIODEMETON?;
DITHIOSYSTOX?; EKATIN TD?; FRUMIN-AL?;
FRUMIN G?; GLEBOFOS?; M-74?; S 276?;
SOLVIREX?; THIODEMETON?; THIODEMETRON?
Safety Profile
Poison by ingestion,
inhalation, skin contact, intraperitoneal, and
intravenous routes. Human mutation data
reported. When heated to decomposition it
emits veq toxic SOx and POx. See also
various demeton entries and ESTERS.
Environmental Fate
Soil/Plant. Disulfoton was metabolized in soil and plants to the corresponding sulfoxide and sulfone via oxidation of the thioether sulfur atoms (Metcalf et al., 1957; Getzin and Shanks, 1970; Takase et al., 1972; Clapp et al., 1976; Worthing and Hance, 1991), the corresponding phosphorothioate analogs and then to derivatives of O,O-diethyl hydrogen phosphate and 2-ethylthioethyl mercaptan (Worthing and Hance, 1991). Disulfoton is rapidly oxidized in soil to its sulfoxide and sulfone with disulfoton oxon sulfoxide and disulfoton oxon sulfone appearing in small amounts (Szeto et al., 1983). In a Portneuf silt loam soil, the persistence of the sulfoxide and sulfone was 32 and >64 days, respectively (Clapp et al., 1976).Disulfoton was translocated from a sandy loam soil into asparagus tips. Disulfoton sulfoxide, disulfoton sulfone, disulfoton oxon sulfoxide and disulfoton oxon sulfone were recovered as metabolites (Szeto and Brown, 1982; Szeto et al., 1983). Disulfoton sGroundwater. According to the U.S. EPA (1986) disulfoton has a high potential to leach to groundwater.Photolytic. Disulfoton was rapidly oxidized to disulfoton sulfoxide and trace amounts (<5% yield) of disulfoton sulfone when sorbed on soil and exposed to sunlight (half-life 1–4 days) (Gohre and Miller, 1986). The photosensitized oxidation was probably due to the presence of singlet oxygen (Gohre and Miller, 1986; Zepp et al., 1981). The degradation rate was higher in soils containing the lowest organic carbon (Gohre and Miller, 1986). Chemical/Physical. Emits toxic fumes of phosphorus and sulfur oxides when heated to decomposition (Sax and Lewis, 1987; Lewis, 1990).When fertilizers containing superphosphate and ammonium nitrate were impregnated with disulfoton, the latter chemically degraded to form disulfoton sulfone and disulfoton sulfoxide (Ibrahim et al., 1969).The reported half-lives for abiotic hydrolysis
Metabolic pathway
Disulfoton is metabolised by an analogous route to phorate. The principal
route of disulfoton metabolism in all media is activation via oxidation
of the thioether group to the sulfoxide (rapid) and sulfone (slower).
Thioether oxidation occurs preferentially to oxidative desulfuration of the
P=S group to the oxon, which is usually only present in trace amounts
and there is good evidence that the sulfoxide and sulfone oxons arise
via disulfoton sulfoxide and sulfone rather than disulfoton oxon. The
more polar thiooxidised metabolites are translocated in plants and are
responsible for the compound's systemic action.
Metabolism
The metabolic
routes of disulfoton are essentially the same in plants,
insects, and mammals, involving the oxidation of the
sulfide group into the sulfoxide and then sulfone,
oxidative desulfuration to the corresponding oxons, and
hydrolysis to diethyl phosphorothioate. In mammals,
orally administered disulfoton is rapidly metabolized and
excreted in the urine. Disulfoton is rapidly degraded in
soil; DT50 (20 ?C) was 1.3–2 d.
Toxicity evaluation
The acute oral LD50 for
rats is 2–12 mg/kg. Inhalation LC50 (4 h) for rats is
0.06–0.015 mg/L air. NOEL (2 yr) for rats is 1 mg/kg
diet (0.05 mg/kg/d). ADI is 0.3 μg/kg b.w.
Degradation
Disulfoton is stable at acidic and neutral pH values but it is hydrolysed
in alkaline media.
Check Digit Verification of cas no
The CAS Registry Mumber 298-04-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,9 and 8 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 298-04:
(5*2)+(4*9)+(3*8)+(2*0)+(1*4)=74
74 % 10 = 4
So 298-04-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H19O2PS3/c1-4-9-11(12,10-5-2)14-8-7-13-6-3/h4-8H2,1-3H3
298-04-4Relevant articles and documents
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Fokin,A.V. et al.
, (1974)
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SUBSTITUTED SPIROCYCLIC KETOENOLS
-
, (2008/06/13)
The present invention relates to novel substituted spirocyclic ketoenols of the formula (I) in which W, X, Y, Z, A, B, D and G are as defined in the disclosure, to a plurality of processes for their preparation and to their use as pesticides, microbicides and herbicides.
Method for preparing O,O-dialkyl S-[2-(alkylthio)alkyl] phosphorodithioates
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Page 4, (2008/06/13)
The invention relates to a method of preparing O,O-dialkyl S-[2-(alkylthio)alkyl]phosphorodithioates by treating -O,O-dialkyl dithiophosphoric acids with a base in the substantial absence of organic solvent to obtain O,O-dialkyl dithiophosphoric acid salts that are in turn treated with thioalcohol derivatives to form the O,O-dialkyl S-[2-(alkylthio)alkyl]phosphorodithioates.
