Disulfoton

Source: Wikipedia, the free encyclopedia.
Disulfoton
Names
Preferred IUPAC name
O,O′-Diethyl S-[2-(ethylsulfanyl)ethyl] phosphorodithioate
Other names
O,O-Diethyl S-2-(ethylthio)ethyl phosphorodithioate, Di-Syston, Thiodemeton
Identifiers
3D model (
JSmol
)
1709167
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.005.505 Edit this at Wikidata
EC Number
  • 206-054-3
KEGG
RTECS number
  • TD9275000
UNII
UN number 3018 2783
  • InChI=1S/C8H19O2PS3/c1-4-9-11(12,10-5-2)14-8-7-13-6-3/h4-8H2,1-3H3 checkY
    Key: DOFZAZXDOSGAJZ-UHFFFAOYSA-N checkY
  • InChI=1/C8H19O2PS3/c1-4-9-11(12,10-5-2)14-8-7-13-6-3/h4-8H2,1-3H3
    Key: DOFZAZXDOSGAJZ-UHFFFAOYAD
  • S=P(OCC)(SCCSCC)OCC
Properties
C8H19O2PS3
Molar mass 274.404
Appearance Oily, colorless to yellow liquid
Odor Characteristic, sulfurous[1]
Density 1.14 g/mL
0.03% (22.7°C)[1]
Vapor pressure 0.0002 mmHg (20°C)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
GHS labelling:[2]
GHS06: ToxicGHS09: Environmental hazard
Danger
H300, H310, H410
P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, P501
Flash point > 82 °C; 180 °F; 355 K[1]
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 TWA 0.1 mg/m3 [skin][1]
IDLH
(Immediate danger)
 N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Disulfoton is an

Bayer CropScience. Disulfoton in its pure form is a colorless oil but the technical product used in vegetable fields is dark and yellowish with a sulfur odor. Disulfoton is processed as a liquid into carrier granules, these granules are mixed with fertilizer and clay to be made into a spike, designed to be driven into the ground. The pesticide is absorbed over time by the roots and translocated to all parts of the plant. The pesticide acts as a cholinesterase inhibitor
and gives long lasting control.

The use of the substance has been restricted by the

US government. Bayer, the manufacturer, exited the US market December 31, 2009.[3]

Synthesis

Disulfoton is synthesized by sulfide formation of 2-ethylthioethanol + O,O-diethyl hydrogen phosphorodithioate with beta-chloroethyl thioethyl ether.[4]

Metabolites

Oxidation of Disulfoton happens rapidly and metabolizes disulfoton into sulfones and sulfoxides, oxidation to oxygen analogs and/or hydrolysis to produce a corresponding phosphorothionate or phosphate. Microsomal enzymes are being inhibited during the metabolism.[5]

Mechanism of action

Organophosphorus pesticides like Disulfoton inhibit esterase enzyme activity like choline esterase. These types of pesticides can also directly interact with the biochemical receptors of acetylcholine
.

Organophosphates in general poisons mammals and insects by phosphorylating the acetylcholinesterase enzyme at nerve endings resulting in loss of function of the enzyme. This allows the accumulation of the neurotransmitter acetylcholine in cholinergic neuroeffector junctions, skeletal myoneural junctions, and autonomic ganglia. This refers to the type of receptors of acetylcholine, the muscarinic and nicotinic effects respectively. Thus organophosphates also impairs nerve impulse transmission.[6][7]

Disulfoton can be absorbed via ingestion, inhalation or penetration of the skin as it can be rapidly absorbed via mucous membranes.[7] When disulfoton is absorbed, it will be distributed via the blood circulation and undergo hydrolytic degradation. This mainly happens in the liver or kidneys but in other tissues as well. Disulfoton is excreted in different metabolites via the urine.[6]

Toxicity

Disulfoton is classified as a super toxic substance. The estimated oral lethal dose in humans is less than 5 mg/kg, which is analog to seven drops for a 70 kg person.

Not only oral intake, but also skin contact and inhalation are fatal because of acute toxicity. Disulfoton is also very toxic to aquatic life and forms an acute hazard with long lasting effects.

Symptoms

Signs of disulfoton toxicity includes headaches,

sialorrhea. Death can occur when respiratory arrest ensues from failure of the respiratory muscles.[8] Other symptoms found in a patient with an unknown quantity of disulfoton were intra-alveolar bleeding, blood in the bronchus, edema of the lungs and swelling of the glomerulus.[9]

Treatment

The treatment of the granular form of disulfoton poisoning should be with repetitive or prolonged gastric and intestinal lavage (washing out of the body cavity). Also charcoal and a continuous intravenous infusion of

atropine sulfate.[10]

See also

  • phosphorothioate
    equivalent

References

  1. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0245". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "Disulfoton". pubchem.ncbi.nlm.nih.gov.
  3. Environmental Protection Agency. "Restricted Use Products (RUP) Report: Six Month Summary List". Archived from the original
    on 11 January 2010. Retrieved 1 December 2009.
  4. ISSN 2616-7719
    .
  5. ISSN 1074-9098
    .
  6. ^
    ISSN 1475-3162
    .
  7. ^
    ISSN 1051-5658
    .
  8. S2CID 80076840
    .
  9. doi:10.26616/nioshpub2017185. {{cite journal}}: Cite journal requires |journal= (help
    )
  10. ISSN 1742-7835
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Disulfoton&oldid=1192546226"