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Phoxim

Phoxim

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Also known as: Baythion, Valexon, Volaton, Valexone, 14816-18-3, Foxima

Molecular Formula

C₁₂H₁₅N₂O₃PS

Molecular Weight

298.30 g/mol

InChI Key

ATROHALUCMTWTB-WYMLVPIESA-N

Phoxim is a synthetic organophosphate acetylcholinesterase inhibitor that is used as a pesticide. It is characterized as a yellow liquid, and exposure occurs by inhalation, ingestion, or contact.

1 2D Structure

Phoxim

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(Z)-N-diethoxyphosphinothioyloxybenzenecarboximidoyl cyanide

2.1.2 InChI

InChI=1S/C12H15N2O3PS/c1-3-15-18(19,16-4-2)17-14-12(10-13)11-8-6-5-7-9-11/h5-9H,3-4H2,1-2H3/b14-12+

2.1.3 InChI Key

ATROHALUCMTWTB-WYMLVPIESA-N

2.1.4 Canonical SMILES

CCOP(=S)(OCC)ON=C(C#N)C1=CC=CC=C1

2.1.5 Isomeric SMILES

CCOP(=S)(OCC)O/N=C(\C#N)/C1=CC=CC=C1

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Bay 77488

2. Baythion

3. Phenylglyoxylonitrile Oxime O,o-diethylphosphorothioate

4. Sebacil

5. Sebacil Pour-on

6. Valekson

7. Valexon

2.2.2 Depositor-Supplied Synonyms

1. Baythion

2. Valexon

3. Volaton

4. Valexone

5. 14816-18-3

6. Foxima

7. Phoxim Solution

8. Phoxime

9. Bay 77488

10. Bayer 77488

11. Bay Sra 7502

12. Bayer 9053

13. Bay 5621

14. Oms 1170

15. Ent 27488

16. Benzoyl Cyanide O-(diethoxyphosphinothioyl)oxime

17. B 77488

18. (diethoxy-thiophosphoryloxyimino)-phenyl Acetonitrile

19. 3,5-dioxa-6-aza-4-phosphaoct-6-ene-8-nitrile, 4-ethoxy-7-phenyl-, 4-sulfide

20. 2-(diethoxyphosphinothioyloxyimino)-2-phenylacetonitrile

21. Phenylglyoxylonitrile Oxime O,o-diethyl Phosphorothioate

22. O,o-diethyl Phosphorothioate, O-ester With Phenylglyoxylonitrile Oxime

23. 4-ethoxy-7-phenyl-3,5-dioxa-6-aza-4-phosphaoct-6-ene-8-nitrile 4-sulfide

24. Ncgc00166158-01

25. Dsstox_cid_14324

26. Dsstox_rid_79143

27. Dsstox_gsid_34324

28. Phoxim [inn:ban]

29. Caswell No. 902l

30. Phoximum

31. Foxima [inn-spanish]

32. Phoxime [inn-french]

33. Phoxime [iso-french]

34. Phoximum [inn-latin]

35. (z)-phoxim

36. Phenylglyoxylnitrile Oxime O,o-diethyl Phosphorothioate

37. Sebacil (insecticide)

38. Cas-14816-18-3

39. Phoxim [bsi:iso]

40. Sra 7502

41. Einecs 238-887-3

42. 6f5v775vpo

43. Bayer-9053

44. Bay-77488

45. Epa Pesticide Chemical Code 598800

46. Unii-6f5v775vpo

47. Phoxin

48. Foxim

49. Ai3-27448

50. Phoxim 10 Microg/ml In Cyclohexane

51. Phoxim 100 Microg/ml In Cyclohexane

52. Diethoxyphosphinothioyloxyimino(phenyl)acetonitrile

53. Phoxim (ban)

54. O,o-diethyl Alpha-cyanobenzylideneamino-oxyphosphonothioate

55. Bayer 5621

56. Benzeneacetonitrile, Alpha-(((diethoxyphosphinothioyl)oxy)imino)-

57. O,o-diaethyl-o-(alpha-cyanbenzyliden-amino)-thionphosphat [german]

58. O,o-diaethyl-o-(alpha-cyano-benzylidenamino)-monothiophosphat [german]

59. Sebacil [veterinary] (tn)

60. Schembl591312

61. Chembl1906626

62. Atrohalucmtwtb-wymlvpiesa-

63. Dtxsid80860144

64. O,o-diaethyl-o-(alpha-cyanbenzyliden-amino)-thionphosphat

65. Glyoxylonitrile, Phenyl-, Oxime O,o-diethyl Phosphorothioate

66. Glyoxylonitrile, Phenyl-, Oxime, O,o-diethyl Phosphorothioate

67. O,o-diaethyl-o-(alpha-cyano-benzylidenamino)-monothiophosphat

68. Tox21_113357

69. Tox21_301580

70. Akos015915518

71. Tox21_113357_1

72. Ncgc00163705-02

73. Ncgc00166158-02

74. Ncgc00255304-01

75. 217075-82-6

76. Phoxim, Pestanal(r), Analytical Standard

77. C18757

78. D08373

79. 816p183

80. A808742

81. Sr-01000883974

82. J-008445

83. Sr-01000883974-1

84. Q27895843

85. (2z)-2-diethoxyphosphinothioyloxyimino-2-phenylacetonitrile

86. Benzeneacetonitrile, [[(diethoxyphosphinothioyl)oxy]imino]-

87. O,o-diaethyl-o-(.alpha.-cyanbenzyliden-amino)-thionphosphat

88. O,o-diethyl-.alpha.-cyanobenzylidineaminooxyphosphonothiate

89. (2z)-2-diethoxyphosphinothioyloxyimino-2-phenyl-ethanenitrile

90. .alpha.-(((diethoxyphosphinothioyl)oxy)imino)benzeneacetonitrile

91. O,o-diaethyl-o-(.alpha.-cyano-benzylidenamino)-monothiophosphat

92. O,o-diethyl .alpha.-cyanobenzylideneamino-oxyphosphonothioate

93. O,o-diethyl O-(.alpha.-cyanobenzylideneamino)phosphorothioate

94. Benzeneacetonitrile, .alpha.-[[(diethoxyphosphinothioyl)oxy]imino]-

95. 4-ethoxy-7-phenyl-3,5-dioxa-6-aza-4-phosphaoct-6-ene-8-nitril 4-sulfide

2.3 Create Date

2006-10-24

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₅N₂O₃PS
Molecular Weight	298.30 g/mol
XLogP3	4.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Exact Mass	298.05410052 g/mol
Monoisotopic Mass	298.05410052 g/mol
Topological Polar Surface Area	95.9 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	389
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Cholinesterase Inhibitors

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)

Insecticides

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)