301-12-2 Hazards Identification
Pictogram(s):
Signal:
Danger
GHS Hazard Statements:
H301: Toxic if swallowed [Danger Acute toxicity, oral]
H311: Toxic in contact with skin [Danger Acute toxicity, dermal]
H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
Precautionary Statement Codes:
P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501
Hazard Classes and Categories:
Acute Tox. 3 *
Aquatic Acute 1
Acute toxicity - category 3
Hazardous to the aquatic environment (acute) - category 1
Acute toxicity (Oral) - Category 2
Acute toxicity (Dermal) - Category 2
Acute toxicity (Inhalation: Dusts and mists) - Category 2
Germ cell mutagenicity - Category 2
Reproductive toxicity - Category 2
Specific target organ toxicity - Single exposure - Category 1 (nervous system)
Specific target organ toxicity - Repeated exposure - Category 1 (nervous system)
Hazardous to the aquatic environment (Acute) - Category 1
Hazardous to the aquatic environment (Long-term) - Category 1
Hazards Summary:
A cholinesterase inhibitor; Can be absorbed through skin; [CAMEO] A woman who was five months pregnant attempted suicide by ingestion and was hospitalized with symptoms including miosis, respiratory distress, muscular fasciculations, and coma (12 hours after admittance); Blood cholinesterase was reduced by 90%; The remainder of her pregnancy was without incident, and the baby's neurological exams at birth and 8 days later were normal; [HSDB] Occupational exposure less likely to be symptomatic or require hospitalization than exposure to other cholinesterase inhibitors; [Reference #1] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]
301-12-2 Usage
Uses
Used in Agriculture:
DEMETON-S-METHYL SULFOXIDE is used as an insecticide for controlling sucking insects on fruit, vines, vegetables, cereals, and ornamentals.
Used in Vegetable Production:
DEMETON-S-METHYL SULFOXIDE is used as a systemic and contact insecticide and acaricide for controlling spider mites and other insects on vegetables and some ornamentals.
Used in Chemical Industry:
DEMETON-S-METHYL SULFOXIDE is used as a colorless to amber-colored liquid in chemical formulations and processes. It is miscible with water and readily soluble in dichloromethane, 2-propanol, and toluene, but practically insoluble in n-hexane.
Air & Water Reactions
Water soluble. DEMETON-S-METHYL SULFOXIDE may be rapidly hydrolyzed by alkali .
Reactivity Profile
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.
Fire Hazard
DEMETON-S-METHYL SULFOXIDE is flammable.
Safety Profile
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.
Environmental Fate
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).
Metabolic pathway
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.
Metabolism
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 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 evaluation
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.
Degradation
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).
Check Digit Verification of cas no
The CAS Registry Mumber 301-12-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,0 and 1 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 301-12:
(5*3)+(4*0)+(3*1)+(2*1)+(1*2)=22
22 % 10 = 2
So 301-12-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H15O4PS2/c1-4-13(8)6-5-12-11(7,9-2)10-3/h4-6H2,1-3H3
301-12-2Relevant academic research and scientific papers
Selective Sulfur Oxygenation in Phosphoroamidate, Thionophosphate, and Thiophosphate Agrochemicals by Perfluoro-cis-2,3-dialkyloxaziridine
Terreni, Marco,Pregnolato, Massimo,Resnati, Giuseppe,Benfenati, Emilio
, p. 7981 - 7992 (2007/10/02)
Several organophsophorus agrochemicals 2a-g with thioether, phosphoramidic, phosphorothioic, and phosphorothionic functions were reacted with perfluoro-cis-2-n-butyl-3-n-propyloxaziridine 1.The selective oxygenation of sulfide function to give sulfoxide derivatives 3a-g occured in high yields without overoxidation to sulfone products.Sulfoxides 3a-e were further oxidized under mild conditions to the corresponding sulfones 4a-e.All the products are themselves of interest as analytical environmental standards and their preparation is described in detail.
