Oxydemeton-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.
Oxydemeton 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.
Oxydemeton-methyl is used to control sucking insects on fruit,
vines, vegetables, cereals and ornamentals.
Systemic and contact insecticide and acaricide used to control spider mites and
other insects on vegetables and some ornamentals.
A metabolite of Demeton-S-methyl (D231370). An organophosphorus pesticide biomarker.
ChEBI: 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.
Oxydemeton-methyl is commercially produced through a multi-step synthesis involving esterification and oxidation of organophosphorus intermediates. It typically begins with the preparation of demeton-S-methyl, its precursor. This involves the reaction of dimethyl thiophosphoryl chloride with 2-(ethylthio)ethanol, forming the phosphorothioate ester. The resulting compound is then oxidized using agents such as hydrogen peroxide or peracids to convert the sulphur atom into a sulfoxide, yielding oxydemeton-methyl. These reactions are carried out in organic solvents like toluene or dichloromethane under controlled temperature and pH conditions to ensure high yield and purity.
Water soluble. DEMETON-S-METHYL SULFOXIDE may be rapidly hydrolyzed by alkali .
Organophosphates 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.
DEMETON-S-METHYL SULFOXIDE is flammable.
Systemic with contact and stomach action. Rapid knockdown effect. Acetylcholinesterase (AchE) inhibitor.
Poison 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.
Soil. 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).
Oxydemeton-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.
Almost 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 PS 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.
The
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.
Oxydemeton-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).
