Oxydemeton-methyl

Oxydemeton-methyl Basic information
Product Name:Oxydemeton-methyl
Synonyms:aimcosystox;bay21097;bayer21097;demeton-methylsulphoxide;META SYSTOX-R(R);DEMETON-S-METHYL SULFONE;DEMETON-S-METHYL SULFOXIDE;OXYDEMETON-METHYL
CAS:301-12-2
MF:C6H15O4PS2
MW:246.28
EINECS:206-110-7
Product Categories:Inhibitors;Metabolites & Impurities;Phosphorylating and Phosphitylating Agents;Sulfur & Selenium Compounds
Mol File:301-12-2.mol
Oxydemeton-methyl Structure
Oxydemeton-methyl Chemical Properties
Melting point <-20℃
Boiling point 106 °C(Press: 0.01 Torr)
density 1.289 g/cm3 (20 ºC)
vapor pressure  3.8×10-3 Pa (20°C)
refractive index 1.5216 (589.3 nm 20℃)
storage temp. 0-6°C
solubility Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
form Oil
Water Solubility Miscible
color Colourless to Light Yellow
EPA Substance Registry SystemOxydemeton-methyl (301-12-2)
Safety Information
Hazard Codes T,N
Risk Statements 24/25-50
Safety Statements 23-36/37-45-61
RIDADR 3018
RTECS TG1420000
HazardClass 6.1(a)
PackingGroup II
Hazardous Substances Data301-12-2(Hazardous Substances Data)
ToxicityLC50 (96-hour) for rainbow trout 4.0 mg/L (Walker, 1964); LC50 (24-hour) for rainbow trout and bluegill sunfish 10 mg/L (Hartley and Kidd, 1987); acute oral LD50 for rats 65–75 mg/kg (Hartley and Kidd, 1987), 30 mg/kg (RTECS, 1985).
MSDS Information
Oxydemeton-methyl Usage And Synthesis
DescriptionOxydemeton-methyl, i.e., demeton-S-methyl sulfoxide, is a colorless oil, bp 106 ?C/0.01 mm Hg, vp 3.8 mPa (20 ?C). It is miscible with water and soluble in most organic solvents, except petroleum ether. Log Kow = ?0.74(21 ?C). Oxydemeton-methyl is relatively stable in acidic media but hydrolyzed in alkalinemedia;DT50 values (22 ?C) at pH 4, 7, and 9 are 107, 46, and 2 d, respectively.
Chemical PropertiesOxydemeton methyl is a colorless to amber-colored liquid. Oxydemeton methyl is relatively slowly hydrolyzed in acidic media, but rapidly hydrolyzed in alkaline media.
Oxydemeton methyl is miscible with water; readily soluble (10–100 g/ 100 mL) in dichloromethane, 2-propanol, and toluene; and practically insoluble (<1 g/100 mL) in n-hexane.
UsesOxydemeton-methyl is used to control sucking insects on fruit, vines, vegetables, cereals and ornamentals.
UsesSystemic and contact insecticide and acaricide used to control spider mites and other insects on vegetables and some ornamentals.
UsesA metabolite of Demeton-S-methyl (D231370). An organophosphorus pesticide biomarker.
DefinitionChEBI: Oxydemeton-methyl is an organic thiophosphate and an organothiophosphate insecticide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide and an agrochemical. It is functionally related to a 2-(ethanesulfinyl)ethanol.
General DescriptionClear amber liquid.
Air & Water ReactionsWater soluble. DEMETON-S-METHYL SULFOXIDE may be rapidly hydrolyzed by alkali .
Reactivity ProfileOrganophosphates such as DEMETON-S-METHYL SULFOXIDE 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.
Fire HazardDEMETON-S-METHYL SULFOXIDE is flammable.
Safety ProfilePoison by ingestion, skin contact, intravenous, and intraperitoneal routes. Human mutation data reported. When heated to decomposition it emits very toxic fumes of POx and SOx. See also other demeton entries.
Environmental FateSoil. The sulfoxide group is oxidized to the sulfone and oxidative and hydrolytic cleavage of the side chain gives dimethylphosphoric and phosphoric acids (Hartley and Kidd, 1987). Oxamyl was degraded by the microorganism Pseudomonas putida in a laboratory study using cultured bacteria (Zeigler, 1980).
Plant. In asparagus, oxydemeton-methyl was converted to the corresponding sulfone (Szeto and Brown, 1982).
Chemical/Physical. Oxydemeton-methyl can be converted to the corresponding sulfone by hydrogen peroxide (Cremlyn, 1991). Emits toxic fumes of phosphorus and sulfur oxides when heated to decomposition (Sax and Lewis, 1987).
Metabolic pathwayOxydemeton-methyl is the primary thiooxidation metabolite of demeton- S-methyl. It is further oxidised rapidly to demeton-Smethylsulfon in all media. The major route of further metabolism of both sulfoxide and sulfone is via hydrolysis to the sulfoxide and sulfone thiols. Stage I1 metabolism of these thiol hydrolysis products proceeds via oxidation and conjugation and is different in soil, plants and animals. In plants the thiols are conjugated, whereas in animals they are mainly methylated and oxidised to sulfoxides, sulfones and sulfonic acids. Demethylation is an important route in mammals; however, the compound is sufficiently polar for much to be excreted in the urine unchanged. Demethylation has also been reported to occur in plants.
MetabolismAlmost 99% of orally administered oxydemeton-methyl to animals is excreted within 48 h in the urine. It is oxidized to the sulfone, followed by hydrolytic cleavage of the P?S bond. The thiol metabolites are conjugated or methylated. O-Demethylation is also an important degradation route both inmammals and plants. Oxydemeton-methyl is rapidly degraded in soils.
Toxicity evaluationThe acute oral LD50 for rats is about 50 mg/kg. Inhalation LC50 (4 h) for rats is 0.47 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. for the sum of oxydemeton-methyl, demeton-S-methylsulfone, and demeton-S-methyl.
DegradationOxydemeton-methyl is relatively slowly hydrolysed in acidic media but rapidly hydrolysed under alkaline conditions. Half-lives at pH values 4,7 and 9 were 107,46 and 2 days respectively (PM). Under sterile aqueous conditions oxydemeton-methyl was degraded to give the oxidised hydrolysis product bis[2-(ethylsulfinyl)ethyl] disulfide (2) (Ziegler et al., 1980) (Scheme 1).
Oxydemeton-methyl Preparation Products And Raw materials
Raw materialsDEMETON-S-METHYL
Ethoprophos Pyrithione Fosthiazate Chlorpyrifos CADUSAFOS Methidathion TEBUPIRIMFOS Phosphorus Fenitrothion Omethoate ESP DEMETON-S-METHYL SULFONE,demeton-s-methyl sulfone (iso),DEMETON-S-METHYL SULFOXIDE disulfoton-oxon-sulfon Oxydemeton-methyl DEMETON VAMIDOTHION SULFOXIDE DEMETON-S-METHYL VAMIDOTHION-SULFONE

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