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2D Structure
Also known as: Counter, 13071-79-9, Contraven, Aragran, Counter 15g soil insecticide, Ac 92100
Molecular Formula
C9H21O2PS3
Molecular Weight
288.4  g/mol
InChI Key
XLNZEKHULJKQBA-UHFFFAOYSA-N
FDA UNII
M83BN0F8R9

Terbufos is a synthetic organic thiophosphate compound and organophosphate acetylcholinesterase inhibitor that is used as a pesticide. It is characterized as a colorless to pale yellow liquid with a mercaptan-like odor, and exposure occurs by inhalation, ingestion, or contact.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
tert-butylsulfanylmethylsulfanyl-diethoxy-sulfanylidene-5-phosphane
2.1.2 InChI
InChI=1S/C9H21O2PS3/c1-6-10-12(13,11-7-2)15-8-14-9(3,4)5/h6-8H2,1-5H3
2.1.3 InChI Key
XLNZEKHULJKQBA-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCOP(=S)(OCC)SCSC(C)(C)C
2.2 Other Identifiers
2.2.1 UNII
M83BN0F8R9
2.3 Synonyms
2.3.1 MeSH Synonyms

1. O,o-diethyl S((tert-butylthio)methyl)phosphorodithioate

2.3.2 Depositor-Supplied Synonyms

1. Counter

2. 13071-79-9

3. Contraven

4. Aragran

5. Counter 15g Soil Insecticide

6. Ac 92100

7. Ent 27920

8. Counter 15g

9. Counter 15g Soil Insecticide-nematicide

10. S-tert-butylthiomethyl O,o-diethyl Phosphorodithioate

11. Phosphorodithioic Acid S-((tert-butylthio)methyl) O,o-diethyl Ester

12. Phosphorodithioic Acid, O,o-diethyl S-(((1,1-dimethylethyl)thio)methyl) Ester

13. Phosphorodithioic Acid, S-[[(1,1-dimethylethyl)thio]methyl] O,o-diethyl Ester

14. M83bn0f8r9

15. Chebi:38960

16. S-(((1,1-dimethylethyl)thio)methyl) O,o-diethyl Phosphorodithioate

17. S-(((1,1-dimethylethyl)thio)methyl)-o,o-diethyl Phosphorodithioate

18. S-t-butylthio-methyl-o,o-diethyl Phosphorodithioate

19. S-[(tert-butylsulfanyl)methyl] O,o-diethyl Phosphorodithioate

20. Dsstox_cid_2254

21. Phosphorodithioic Acid, S-[(tert-butylthio)methyl] O,o-diethyl Ester

22. Dsstox_rid_76530

23. Dsstox_gsid_22254

24. O,o-diethyl S-(tert-butylthio)methyl Phosphorodithioate

25. S-[(tert-butylthio)methyl] O,o-diethyl Dithiophosphate

26. S-[(tert-butylsulfanyl)methyl] O,o-diethyl Dithiophosphate

27. Caswell No. 131a

28. O,o-diethyl S-(((1,1-dimethylethyl)thio)methyl)phoshorodithioate

29. Phosphorodithioic Acid, S-(((1,1-dimethylethyl)thio)methyl) O,o-diethyl Ester

30. Terbufos [ansi:bsi:iso]

31. Terbufos [iso]

32. Cas-13071-79-9

33. Ccris 4772

34. Hsdb 6444

35. St-100

36. Ai3-27920

37. Einecs 235-963-8

38. Epa Pesticide Chemical Code 105001

39. Brn 1710115

40. S-tert-butylthiomethyl O,o-diethylphosphorodithioate

41. Unii-m83bn0f8r9

42. Cyanater

43. Tert-butylsulfanylmethylsulfanyl-diethoxy-sulfanylidene-?^{5}-phosphane

44. S-((tert-butylthio)methyl)o,o-diethylphosphorodithioate

45. Terbufos [hsdb]

46. Terbufos [mi]

47. Phosphorodithioic Acid S-(((1,1-dimethylethyl)thio)methyl) O,o-diethyl Ester

48. Schembl23773

49. 4-01-00-03092 (beilstein Handbook Reference)

50. Chembl1406292

51. Dtxsid2022254

52. Tox21_201634

53. Tox21_302994

54. Terbufos 10 Microg/ml In Cyclohexane

55. Terbufos 1000 Microg/ml In Acetone

56. Akos016014230

57. Terbufos 10 Microg/ml In Acetonitrile

58. Terbufos 100 Microg/ml In Acetonitrile

59. Ncgc00091771-01

60. Ncgc00091771-02

61. Ncgc00091771-03

62. Ncgc00256426-01

63. Ncgc00259183-01

64. Ac-92100

65. O,o-diethyl-s-1,1-dimethylethylthiomethyl

66. Terbufos, Pestanal(r), Analytical Standard

67. C18693

68. 071t799

69. J-005860

70. Q2404344

71. S-[(tert-butylthio)methyl] O,o-diethyl Phosphorodithioate

72. S-[(tert-butylsulfanyl)methyl] O,o-diethyl Dithiophosphate #

73. O,o-diethyl S-[[(1,1-dimethylethyl)thio]methyl] Phosphorodithioate

74. S-[[(1,1-dimethylethyl)thio]methyl] O,o-diethyl Phoshporodithioate

75. Diethyl {[(tert-butylsulfanyl)methyl]sulfanyl}(sulfanylidene)phosphonite

76. Tert-butylsulfanylmethylsulfanyl-diethoxy-sulfanylidene-lambda5-phosphane

77. Methanethiol, (tert-butylthio)-, S-ester With O,o-diethyl Phosphorodithioate

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 288.4 g/mol
Molecular Formula C9H21O2PS3
XLogP34.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area101
Heavy Atom Count15
Formal Charge0
Complexity206
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

A metabolism study of rats indicated that 83% of a single administration of 0.8 mg/kg terbufos was excreted in the urine in the form of metabolites and 3.5% in the feces during 168 hours. No terbufos accumulated in tissues.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 924


Rapidly absorbed through skin.

Farm Chemicals Handbook 2002. Meister Publishing Co., 2002., p. C-384


Among 11 farmers who applied a formulated terbufos product while planting corn, ...no alkyl phosphates were detected in urine... /after an estimated respiratory dose of 0.009 mg/cu m terbufos/.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 924


4.2 Metabolism/Metabolites

Metabolism occurs principally by oxidation, hydrolysis by esterases, and by transfer of portions of the molecule to glutathione. Oxidation of organophosphorus insecticides may result in more or less toxic products. The glutathione transferase reactions produce products, that are, in most cases, of low toxicity. Hydrolytic and transferase reactions affect both thioates and their oxons. /Organophosphorus Pesticides/

WHO; Environ Health Criteria 63: Organophosphorus pesticides (1986). Available from, as of July 3,2003: https://www.inchem.org/pages/ehc.html


Biotransformation of terbufos in rat liver revealed four metabolites in the effluent prepared with a C18 cartridge after the rat liver was perfused for one hour in situ. Analysing the spectrogram of GC-IR and GC-MS, metabolite IV appeared to be an oxidative desulfuration product of terbufos with the formula C9H21O3PS2, the recovery of which in the effluent was 2.13%; metabolite I appeared to be an hydrolysate of metabolite IV with the formula C5H13O3PS, the recovery of which was 0.13%; metabolite II appeared to be an hydrolysate of terbufos with the formula C5H13O2PS2, the recovery of which was 2.65%; metabolite III appeared to be a methylate of metabolite II, with the formula C6H15O2PS2, the recovery of which was 1.42%. Relatively the recovery of terbufos was 40.8%. These results were in accord with the regular metabolic pattern in vivo of phosphorothioates with a thioether group.

Li J-T et al; JOURNAL OF OCCUPATIONAL HEALTH 41(2): 62-68 (1999)


4.3 Mechanism of Action

The organophosphorus compounds owe their biological activities to the capacity of the central P atom to phosphorylate the esteratic site of the enzyme, cholinesterase, which is an essential constituent of the nervous system not only of Insecta but also of all higher animals. /Organophosphorus compounds/

Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. 13(81) 448


Organophosphates poison insects and mammals primarily by phosphorylation of the acetylcholinesterase enzyme at nerve endings. ... At sufficient dosage, loss of enzyme function allows accumulation of acetylcholine (the impulse- transmitter substance) at cholinergic neuroeffector junctions (muscarinic effects, and at skeletal myoneural junctions and in autonomic ganglia (nicotinic effects). Organophosphates also impair nerve impulse transmission in the brain ... . /Organophosphate pesticides/

U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: https://www.epa.gov/pesticides/safety/healthcare, p. 34