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Tox21_300733
Also known as: 741-58-2, Betasan, Benzulfide, Prefar, Disan, Sap (herbicide)
Molecular Formula
C14H24NO4PS3
Molecular Weight
397.5  g/mol
InChI Key
RRNIZKPFKNDSRS-UHFFFAOYSA-N
FDA UNII
9882BW2Q2S

1 2D Structure

Tox21_300733

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[2-di(propan-2-yloxy)phosphinothioylsulfanylethyl]benzenesulfonamide
2.1.2 InChI
InChI=1S/C14H24NO4PS3/c1-12(2)18-20(21,19-13(3)4)22-11-10-15-23(16,17)14-8-6-5-7-9-14/h5-9,12-13,15H,10-11H2,1-4H3
2.1.3 InChI Key
RRNIZKPFKNDSRS-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)OP(=S)(OC(C)C)SCCNS(=O)(=O)C1=CC=CC=C1
2.2 Other Identifiers
2.2.1 UNII
9882BW2Q2S
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 741-58-2

2. Betasan

3. Benzulfide

4. Prefar

5. Disan

6. Sap (herbicide)

7. Disan (pesticide)

8. R 4461

9. N-[2-di(propan-2-yloxy)phosphinothioylsulfanylethyl]benzenesulfonamide

10. O,o-diisopropyl 2-(benzenesulfonamido)ethyl Dithiophosphate

11. Chebi:81899

12. O,o-diisopropyl S-(2-benzenesulfonylaminoethyl) Phosphorodithioate

13. 9882bw2q2s

14. N-(2-mercaptoethyl)benzenesulfonamide S-(o,o-diisopropyl Phosphorodithioate)

15. Phosphorodithioic Acid, O,o-diisopropyl Ester, S-ester With N-(2-mercaptoethyl)benzenesulfonamide

16. Sap

17. Kayaphenone

18. Betamec

19. Exporsan

20. Prefer

21. N-(2-(o,o-diisopropyldithiophosphoryl)ethyl)benzenesulfonamide

22. Betasan E

23. Betasan G

24. Prefar E

25. Pre-san

26. Phosphorodithioic Acid, O,o-bis(1-methylethyl) S-(2-((phenylsulfonyl)amino)ethyl) Ester

27. Phosphorodithioic Acid, O,o-bis(1-methylethyl) S-[2-[(phenylsulfonyl)amino]ethyl] Ester

28. Caswell No. 357

29. Betasan [obsolete]

30. Bensumec

31. Bensulide [bsi:iso]

32. Hsdb 393

33. Einecs 212-010-4

34. Epa Pesticide Chemical Code 009801

35. Brn 2164989

36. (n-(2-mercaptoethyl)benzenesulfonamide)

37. Bensulfide

38. N-[2-(o,o-diisopropyldithiophosphoryl)ethyl]benzenesulfonamide

39. Unii-9882bw2q2s

40. Ccris 9246

41. O,o-diisopropyl S-{2-[(phenylsulfonyl)amino]ethyl} Dithiophosphate

42. R-4461

43. Bensulide [iso]

44. N-(beta-o,o-diisopropyldithiophosphorylethyl)benzenesulfonamide

45. S-2-benzenesulfonamidoethyl O,o-di-isopropyl Phosphorodithioate

46. S-2-benzenesulphonamidoethyl O,o-diisopropyl Phosphorodithioate

47. S-beta-(benzenesulfonamido)ethyl O,o-diisopropyl Dithiophosphate

48. Bensulide [hsdb]

49. O,o-di-isopropyl S-2-phenylsulphonylaminoethyl Phosphorodithioate

50. N-(2-ethylthio)benzene Sulphonamide-s,o,o-diisopropylphosphorodithioate

51. N-(2-mercaptoethylbenzene)sulfonamide S-(o,o-diisopropylphosphorodithioate)

52. O,o-bis(1-methylethyl) S-(2-((phenylsulfonyl)amino)ethyl)pheosphorodithioate

53. O,o-bis(1-methylethyl)-s-(2-((phenylsulfonyl)amino)ethyl) Phosphorodithioate

54. S-(o,o-diisopropylphosphorodithioate) Of N-(2-mercaptoethyl)benzenesulfonamide

55. Benzenesulfonamide, N-(2-mercaptoethyl)-, S-ester With O,o-diisopropylphosphorodithioate

56. Dsstox_cid_12329

57. Dsstox_rid_78915

58. O,o-diisopropyl Dithiophosphate S-ester With N-(2-mercaptoethyl)benzenesulphonamide

59. O,o-diisopropyl Phosphorodithioate S-ester With N-(2-mercaptoethyl)benzenesulfonamide

60. O,o-diisopropyl Phosphorothioate S-ester With N-(2-mercaptoethyl)benzenesulfonamide

61. S-(o,o-diisopropyl Phosphorodithioate) Ester Of N-(2-mercaptoethyl)benzenesulfonamide

62. Dsstox_gsid_32329

63. Schembl55205

64. Chembl1895252

65. Dtxsid9032329

66. Tox21_300733

67. Bensulide 100 Microg/ml In Methanol

68. Akos015902619

69. O,o-bis(1-methylethyl) S-(2-((phenylsulfonyl)amino)ethyl)phosphorodithioate

70. Bensulide 1000 Microg/ml In Methanol

71. Bensulide 10 Microg/ml In Acetonitrile

72. Ncgc00168292-01

73. Ncgc00168292-02

74. Ncgc00168292-03

75. Ncgc00168292-04

76. Ncgc00254639-01

77. Cas-741-58-2

78. Bensulide, Pestanal(r), Analytical Standard

79. C18703

80. Q414584

81. O,o'-diisopropyl S-[2-(benzenesulfonamido)ethyl]dithiophosphate

82. O,o'-diisopropyl S-[2-(benzenesulfonamido)ethyl]phosphorodithioate

83. O,o-diisopropyl S-(2-benzenesulfonylaminoethyl)phosphorodithioate

84. S-.beta.-(benzenesulfonamido)ethyl O,o-diisopropyl Dithiophosphate

85. O,o-diisopropyl S-(2-[(phenylsulfonyl)amino]ethyl) Dithiophosphate #

86. (n-(2-ethylthio)benzene Sulfonamido-s,o,o- Diisopropylphosphorodithioate

87. Phosphorodithioic Acid O,o-bis(1-methylethyl) S-[2-[(phenylsulfonyl)amino]ethyl] Ester

88. Phosphorodithioic Acid-o,o-bis(1-methylethyl)-s-(2-((phenylsulfonyl)amino)ethyl)ester

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 397.5 g/mol
Molecular Formula C14H24NO4PS3
XLogP34.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count10
Exact Mass397.06050877 g/mol
Monoisotopic Mass397.06050877 g/mol
Topological Polar Surface Area130 Ų
Heavy Atom Count23
Formal Charge0
Complexity471
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

Selective herbicide, adsorbed on the root surfaces, and a small amount is absorbed by the roots. Translocation of bensulide to the leaves does not occur, but metabolites are translocated.

Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 87


In a metabolism study, bensulide technical, labelled with C in the 14 phenyl ring (> 96.4% radiopurity; 925 MBq/mMole) was dissolved in corn oil (vehicle) and administered to Sprague-Dawley rats (5/sex/group; 7-8 weeks of age; 185-235 g body weight) following 3 treatment regimes. Animals in Group I received a single oral dose of radioactive bensulide at 1 mg/kg bw. Animals in Group II received 14 consecutive doses (1 mg/kg/day) of non-radioactive bensulide technical (99% a.i.) in corn oil, followed by a 1 mg/kg dose of radiolabelled bensulide technical in corn oil on day 15. Group III animals received a single oral dose of radiolabelled bensulide technical at 100 mg/kg bw. An additional group of animals (Group IV; 3/sex/group) were given a single oral dose of radiolabelled bensulide 18 technical at 1 mg/kg bw and were subseqently used for autoradiological radiolabelled carbon dioxide release determinations. ... In Group I, total urinary excretion of 7 days after admin of radioactive bensulide technical accounted for 70 and 75% of the administered dose in males and females, respectively. ... In Group III, total urinary excretion accounted for 75 and 87% of the administered dose in males and females, respectively. ... For Group II (prior 14-day admin of non-radioactive bensulide technical before radioactive bensulide admin, both at 1 mg/kg), total urinary excretion of radioactivity over 7 days past dosing with radioactive bensulide accounted for 79 and 88% of the administered dose in males and females, respectively. For Group IV, urinary excretion of 14-C radioactivity derived from bensulide technical over a 48-hr period accounted for 67% for one male and 86% in one male. For Group I, total fecal excretion of radioactivity derived from 14C-bensulide technical over 7 days post-dosing accounted for 22 and 20% of the administered dose in males and females, respectively. ... For Group III, total fecal elim over 7 days post-dosing of bensulide-derived radioactivity accounted for 22 and 11% of the administered dose for males and females, respectively. ... In Group II animals, total fecal excretion of radioactivity over 7 days post-dosing accounted for 14 and 8% of the administered dose for males and females, respectively. ... In Group IV, fecal excretion of radioactivity over 48 hrs post-dosing accounted for 12% of the administered dose in one male and 7% in one female. ... The radioactivity found in the carcasses and in other tissues accounted for 0.3% to 2.5% and <0.1% of the administered dose, respectively.

USEPA; Bensulide: Health Effects Division's Chapter for the Reregistration and Eligibility Decision Document. Washington, DC: USEPA, Off Pest Prog. p.17-18 (March 3, 1998)


4.2 Metabolism/Metabolites

Unchanged ring-labelled (14)-C bensulide could be detected in roots of lettuce plants after root application ... . A large part of the radioactive material in the leaves was evolved as radioactive carbon dioxide and some was present as labelled amino acids.

Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 49


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