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Showing toxin card for Disulfoton (T3D0038)

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Version 1.0
Creation Date 2009-03-06 18:57:58
Update Date 2010-03-18 21:52:17
Accession Number T3D0038
Name Disulfoton
Compound Type
  • Organic Compound
  • Organophosphate
  • Pesticide
Description Disulfoton is a manufactured organophosphate used as a pesticide. It is used mainly in agriculture to protect field and vegetable crops. (R230)
Synonyms
  1. Di-syston
  2. Disipton
  3. Disulfoton mixture
  4. Disyston FE-10
  5. Disystox
  6. Dithiodemeton
  7. Dithiosystox
  8. Dution
  9. Ekatin TD
  10. Ekatine
  11. Ethyl thiometon
  12. Ethylthiodemeton
  13. Ethylthiometon b
  14. Glebofos
  15. Insyst-d
  16. O,O-Diaethyl-S-(2-aethylthio-aethyl)-dithiophosphat
  17. O,O-Diaethyl-S-(3-thia-pentyl)-dithiophosphat [German]
  18. O,O-Diethyl 2-ethylthioethyl phosphorodithioate
  19. O,O-Diethyl S-(2-(ethylthio)ethyl) dithiophosphate
  20. O,O-Diethyl S-(2-(ethylthio)ethyl)phosphorodithioate
  21. O,O-Diethyl S-(2-eththioethyl) phosphorodithioate
  22. O,O-Diethyl S-(2-eththioethyl) thiothionophosphate
  23. O,O-Diethyl S-(2-ethylmercaptoethyl) dithiophosphate
  24. O,O-Diethyl S-2-(ethylthio)ethyl phosphorodithioate
  25. O,O-Diethyl S-[2-(Ethylthio)ethyl] dithiophosphate
  26. O,O-Diethyl S-[2-(ethylthio)ethyl] phosphorodithioate
  27. O,O-Diethyl-S-(2-ethylthio-ethyl)-dithiofosfaat [Dutch]
  28. O,O-Dietil-S-(2-etiltio-etil)-ditiofosfato [Italian]
  29. O,O-Ethyl S-2(ethylthio)ethyl phosphorodithioate
  30. O,O-diethyl 2-(ethylthio)ethyl dithiophosphate
  31. O,o-diethyl-s-ethylmercapto-ethyl dithiophosphate
  32. S-[2-(ethylsulfanyl)ethyl] O,O-dimethyl dithiophosphate
  33. Solvigran
  34. Solvirex
  35. Thiodemeton
  36. Thiodemetron
  37. o,o-Diethyl S-[2-(ethylsulfanyl)ethyl] dithiophosphate
Chemical IUPAC Name diethyl {[2-(ethylsulfanyl)ethyl]sulfanyl}(sulfanylidene)phosphonite
Chemical Formula C8H19O2PS3
Chemical Structure Structure
CAS Registry Number 298-04-4
InChI Identifier InChI=1S/C8H19O2PS3/c1-4-9-11(12,10-5-2)14-8-7-13-6-3/h4-8H2,1-3H3
InChI Key InChIKey=DOFZAZXDOSGAJZ-UHFFFAOYSA-N
PubChem Compound ID 3118 Link Image
KEGG ID Not Available
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 38661 Link Image
BioCyc ID Not Available
SuperToxic ID Not Available
CTD ID D004222 Link Image
Stitch ID Disulfoton Link Image
DrugBank ID Not Available
PDB ID Not Available
ACToR ID 1916
Wikipedia Link http://en.wikipedia.org/wiki/Disulfoton Link Image
Monoisotopic Mass 274.028478
MOL File Show
PDB File Show
SDF File Show
SMILES CCOP(=S)(OCC)SCCSCC
Appearance Colorless (pure) or dark yellow (technical grade) oil.
Melting Point -25 °C
Solubility 0.0163 mg/mL at 20 °C [BOWMAN,BT & SANS,WW (1983A)]
Predicted LogP 3.0289
Route of Exposure Oral (R230) ; inhalation (R230) ; dermal (R230)
Mechanism of Action The toxic metabolites of disulfoton, mainly disulfoton sulfoxide, disulfoton sulfone, demeton S-sulfoxide and demeton S-sulfone, inhibit acetylcholinesterase in nervous tissue. The inhibition of acetylcholinesterase results in the accumulation of acetylcholine at the muscarinic and nicotinic cholinergic receptors of nerve synapses, which causes an overstimulation of cholinergic nerves and effector organs. Prolonged exposure to disulfoton results in diminished cholinergic signs as tolerance develops, likely as a result of reduced density of muscarinic receptor binding sites. (R230)
Metabolism Disulfoton is lipophilic and easily absorbed by oral, inhalation, and dermal routes, then distributed primarily to the liver and in smaller quantities to the kidney, fat, skin, muscle, brain, and other organs. In the liver, cytochrome P-450 monooxygenase and flavin adenine dinucleotide monooxygenase metabolize disulfoton into its toxic intermediates, which include disulfoton sulfoxide, disulfoton sulfone, demeton S-sulfoxide and demeton S-sulfone. The active metabolites ultimately undergo hydrolysis to more polar metabolites that are not toxic and are excreted in the urine. (R230)
Toxicity Values LD50: 25 mg/kg (Dermal, Rat) (R289) LD50: 6.8 mg/kg (Oral, Rat) (R289) LD50: 9.4 mg/kg (Intraperitoneal, Rat) (R289)
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Disulfoton is used mainly in agriculture to protect field and vegetable crops, as well as some fruit and nut crops. It may also be used in smaller quantities on home and garden plants and for mosquito control in swamps. (R230)
Minimum Risk Level Acute Inhalation: 0.006 mg/m3 (R260) Intermediate Inhalation: 0.0002 mg/m3 (R260) Acute Oral: 0.001 mg/kg/day (R260) Intermediate Oral: 0.00009 mg/kg/day (R260) Chronic Oral: 0.00006 mg/kg/day (R260)
Health Effects Disulfoton mainly causes harmful effects to the nervous system, such as narrowing of the pupils, vomiting, diarrhea, drooling, difficulty in breathing, tremors, convulsions, and even death. Chronic ingestion of disulfoton may affect the eyes and cause nearsightedness. Disulfoton is also believed to cause developmental problems. (R230)
Symptoms Depending on the amount of disulfoton that enters the body, effects on the nervous system, such as narrowing of the pupils, vomiting, diarrhea, drooling, difficulty in breathing, tremors, convulsions, and even death may occur. Skin contact with disulfoton may cause weakness and fatigue. (R230)
Treatment Treatment for disulfoton poisoning is symptomatic and may include ventilatory support, emesis, or the administration of atropine sulfate and pralidoxime chloride. (R288)
General References
  • R289 - American Conference of Governmental Industrial Hygienists (2001). Documentation of Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices for 2001. Cincinnati, OH: American Conference of Governmental Industrial Hygienists.
  • R230 - ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for disulfoton. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA).
  • R288 - International Programme on Chemical Safety (IPCS) INCHEM (1988). Pesticide Document for Disulfoton.
  • R231 - Usmani KA, Karoly ED, Hodgson E, Rose RL: In vitro sulfoxidation of thioether compounds by human cytochrome P450 and flavin-containing monooxygenase isoforms with particular reference to the CYP2C subfamily. Drug Metab Dispos. 2004 Mar;32(3):333-9. [PubMed Link Image]
  • R260 - ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA).
Targets
  1. Acetylcholinesterase
Target 1 [top]
Target 1 ID 312
Target 1 Name Acetylcholinesterase
Target 1 Mechanism of Action The toxic metabolites of disulfoton, mainly disulfoton sulfoxide, disulfoton sulfone, demeton S-sulfoxide and demeton S-sulfone, inhibit acetylcholinesterase in nervous tissue. The inhibition of acetylcholinesterase results in the accumulation of acetylcholine at the muscarinic and nicotinic cholinergic receptors of nerve synapses, which causes an overstimulation of cholinergic nerves and effector organs. (R230)
Target 1 Description Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis
Target 1 Synonyms
  1. AChE
Target 1 Gene Name ACHE
Target 1 Protein Sequence >Acetylcholinesterase 
MRPPQCLLHTPSLASPLLLLLLWLLGGGVGAEGREDAELLVTVRGGRLRGIRLKTPGGPV
SAFLGIPFAEPPMGPRRFLPPEPKQPWSGVVDATTFQSVCYQYVDTLYPGFEGTEMWNPN
RELSEDCLYLNVWTPYPRPTSPTPVLVWIYGGGFYSGASSLDVYDGRFLVQAERTVLVSM
NYRVGAFGFLALPGSREAPGNVGLLDQRLALQWVQENVAAFGGDPTSVTLFGESAGAASV
GMHLLSPPSRGLFHRAVLQSGAPNGPWATVGMGEARRRATQLAHLVGCPPGGTGGNDTEL
VACLRTRPAQVLVNHEWHVLPQESVFRFSFVPVVDGDFLSDTPEALINAGDFHGLQVLVG
VVKDEGSYFLVYGAPGFSKDNESLISRAEFLAGVRVGVPQVSDLAAEAVVLHYTDWLHPE
DPARLREALSDVVGDHNVVCPVAQLAGRLAAQGARVYAYVFEHRASTLSWPLWMGVPHGY
EIEFIFGIPLDPSRNYTAEEKIFAQRLMRYWANFARTGDPNEPRDPKAPQWPPYTAGAQQ
YVSLDLRPLEVRRGLRAQACAFWNRFLPKLLSATDTLDEAERQWKAEFHRWSSYMVHWKN
QFDHYSKQDRCSDL
Target 1 Number of Residues 614
Target 1 Molecular Weight 67795.5
Target 1 Theoretical pI 6.24
Target 1 GO Classification
Function
catalytic activity
hydrolase activity
hydrolase activity, acting on ester bonds
carboxylic ester hydrolase activity
cholinesterase activity
Process
Not Available
Component
Not Available
Target 1 General Function Lipid transport and metabolism
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Signals
  • 1-31
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non Essential
Target 1 Domain Function PF08674:AChE_tetra PF00135:COesterase
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB ID P22303 Link Image
Target 1 Cellular Location Isoform H:Cell membrane
Target 1 Gene Sequence >1845 bp 
ATGAGGCCCCCGCAGTGTCTGCTGCACACGCCTTCCCTGGCTTCCCCACTCCTTCTCCTC
CTCCTCTGGCTCCTGGGTGGAGGAGTGGGGGCTGAGGGCCGGGAGGATGCAGAGCTGCTG
GTGACGGTGCGTGGGGGCCGGCTGCGGGGCATTCGCCTGAAGACCCCCGGGGGCCCTGTC
TCTGCTTTCCTGGGCATCCCCTTTGCGGAGCCACCCATGGGACCCCGTCGCTTTCTGCCA
CCGGAGCCCAAGCAGCCTTGGTCAGGGGTGGTAGACGCTACAACCTTCCAGAGTGTCTGC
TACCAATATGTGGACACCCTATACCCAGGTTTTGAGGGCACCGAGATGTGGAACCCCAAC
CGTGAGCTGAGCGAGGACTGCCTGTACCTCAACGTGTGGACACCATACCCCCGGCCTACA
TCCCCCACCCCTGTCCTCGTCTGGATCTATGGGGGTGGCTTCTACAGTGGGGCCTCCTCC
TTGGACGTGTACGATGGCCGCTTCTTGGTACAGGCCGAGAGGACTGTGCTGGTGTCCATG
AACTACCGGGTGGGAGCCTTTGGCTTCCTGGCCCTGCCGGGGAGCCGAGAGGCCCCGGGC
AATGTGGGTCTCCTGGATCAGAGGCTGGCCCTGCAGTGGGTGCAGGAGAACGTGGCAGCC
TTCGGGGGTGACCCGACATCAGTGACGCTGTTTGGGGAGAGCGCGGGAGCCGCCTCGGTG
GGCATGCACCTGCTGTCCCCGCCCAGCCGGGGCCTGTTCCACAGGGCCGTGCTGCAGAGC
GGTGCCCCCAATGGACCCTGGGCCACGGTGGGCATGGGAGAGGCCCGTCGCAGGGCCACG
CAGCTGGCCCACCTTGTGGGCTGTCCTCCAGGCGGCACTGGTGGGAATGACACAGAGCTG
GTAGCCTGCCTTCGGACACGACCAGCGCAGGTCCTGGTGAACCACGAATGGCACGTGCTG
CCTCAAGAAAGCGTCTTCCGGTTCTCCTTCGTGCCTGTGGTAGATGGAGACTTCCTCAGT
GACACCCCAGAGGCCCTCATCAACGCGGGAGACTTCCACGGCCTGCAGGTGCTGGTGGGT
GTGGTGAAGGATGAGGGCTCGTATTTTCTGGTTTACGGGGCCCCAGGCTTCAGCAAAGAC
AACGAGTCTCTCATCAGCCGGGCCGAGTTCCTGGCCGGGGTGCGGGTCGGGGTTCCCCAG
GTAAGTGACCTGGCAGCCGAGGCTGTGGTCCTGCATTACACAGACTGGCTGCATCCCGAG
GACCCGGCACGCCTGAGGGAGGCCCTGAGCGATGTGGTGGGCGACCACAATGTCGTGTGC
CCCGTGGCCCAGCTGGCTGGGCGACTGGCTGCCCAGGGTGCCCGGGTCTACGCCTACGTC
TTTGAACACCGTGCTTCCACGCTCTCCTGGCCCCTGTGGATGGGGGTGCCCCACGGCTAC
GAGATCGAGTTCATCTTTGGGATCCCCCTGGACCCCTCTCGAAACTACACGGCAGAGGAG
AAAATCTTCGCCCAGCGACTGATGCGATACTGGGCCAACTTTGCCCGCACAGGGGATCCC
AATGAGCCCCGAGACCCCAAGGCCCCACAATGGCCCCCGTACACGGCGGGGGCTCAGCAG
TACGTTAGTCTGGACCTGCGGCCGCTGGAGGTGCGGCGGGGGCTGCGCGCCCAGGCCTGC
GCCTTCTGGAACCGCTTCCTCCCCAAATTGCTCAGCGCCACCGACACGCTCGACGAGGCG
GAGCGCCAGTGGAAGGCCGAGTTCCACCGCTGGAGCTCCTACATGGTGCACTGGAAGAAC
CAGTTCGACCACTACAGCAAGCAGGATCGCTGCTCAGACCTGTGA
Target 1 GenBank Gene ID Not Available
Target 1 GeneCard ID ACHE Link Image
Target 1 GenAtlas ID ACHE Link Image
Target 1 HGNC ID HGNC:108 Link Image
Target 1 Chromosome Location Not Available
Target 1 Locus 7q22
Target 1 SNPs SNPJam Report Link Image
Target 1 Toxin References
  • R230 - ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for disulfoton. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA).
Target 1 General References 2263619; 8299725; 14702039; 12853948; 15489334; 11239002

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