Demeton

Demeton, sold as an amber oily liquid with a sulphur like odour under the name Systox, is an organophosphate derivative causing irritability and shortness of breath to individuals repeatedly exposed. It was used as a phosphorothioate insecticide and acaricide and has the chemical formula C8H19O3PS2. Although it was previously used as an insecticide, it is now largely obsolete due to its relatively high toxicity to humans. Demeton consists of two components, demeton-S and demeton-O in a ratio of approximately 2:1 respectively. The chemical structure of demeton is closely related to military nerve agents such as VX and a derivative with one of the ethoxy groups replaced by methyl was investigated by both the US and Soviet chemical-weapons programs under the names V.sub.X and GD-7.

Demeton
Names
Preferred IUPAC name
O,O-Diethyl S-[2-(ethylsulfanyl)ethyl] phosphorothioate
Other names
Demeton thiol; Izosystox
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.366
UNII
  • InChI=1S/C8H19O3PS2/c1-4-10-12(9,11-5-2)14-8-7-13-6-3/h4-8H2,1-3H3 Y
    Key: GRPRVIYRYGLIJU-UHFFFAOYSA-N Y
  • InChI=1/C8H19O3PS2/c1-4-10-12(9,11-5-2)14-8-7-13-6-3/h4-8H2,1-3H3
    Key: GRPRVIYRYGLIJU-UHFFFAOYAI
  • O=P(OCC)(SCCSCC)OCC
Properties
C8H19O3PS2
Molar mass 258.3384 g/mol
Appearance colorless to amber oily liquid
Odor sulfurous
Density 1.146 g/cm3
Boiling point 128 °C (262 °F; 401 K)
2.0 g/100 mL
log P 2.38
1.5
Hazards
Flash point 147.6 °C (297.7 °F; 420.8 K)
Lethal dose or concentration (LD, LC):
1.5 mg/kg (oral, rat)
5 mg/kg (rabbit, oral)
7.85 mg/kg (mouse, oral)
1.7 mg/kg (rat, oral)
15 mg/m3 (rat, 4 hr)
15 mg/m3 (cat, 4 hr)
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 0.1 mg/m3 [skin]
REL (Recommended)
TWA 0.1 mg/m3 [skin]
IDLH (Immediate danger)
10 mg/m3
Related compounds
Demeton-S-methyl
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
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