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Chemistry

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Also known as: 188425-85-6, Nicobifen, Endura, Emerald, 2-chloro-n-(4'-chloro-[1,1'-biphenyl]-2-yl)nicotinamide, Boscalid [iso]
Molecular Formula
C18H12Cl2N2O
Molecular Weight
343.2  g/mol
InChI Key
WYEMLYFITZORAB-UHFFFAOYSA-N
FDA UNII
32MS8ZRD1V

Boscalid
Boscalid has been investigated for the treatment of OSDI, Glaucoma, Staining, Schirmers, and Disease Severity, among others.
1 2D Structure

Boscalid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-chloro-N-[2-(4-chlorophenyl)phenyl]pyridine-3-carboxamide
2.1.2 InChI
InChI=1S/C18H12Cl2N2O/c19-13-9-7-12(8-10-13)14-4-1-2-6-16(14)22-18(23)15-5-3-11-21-17(15)20/h1-11H,(H,22,23)
2.1.3 InChI Key
WYEMLYFITZORAB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C(=C1)C2=CC=C(C=C2)Cl)NC(=O)C3=C(N=CC=C3)Cl
2.2 Other Identifiers
2.2.1 UNII
32MS8ZRD1V
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-chloro-n-(4-chlorobiphenyl-2-yl)nicotinamide

2.3.2 Depositor-Supplied Synonyms

1. 188425-85-6

2. Nicobifen

3. Endura

4. Emerald

5. 2-chloro-n-(4'-chloro-[1,1'-biphenyl]-2-yl)nicotinamide

6. Boscalid [iso]

7. 2-chloro-n-(4'-chlorobiphenyl-2-yl)nicotinamide

8. 2-chloro-n-[2-(4-chlorophenyl)phenyl]pyridine-3-carboxamide

9. 3-pyridinecarboxamide, 2-chloro-n-(4'-chloro[1,1'-biphenyl]-2-yl)-

10. Bas 510

11. Bas-510

12. 32ms8zrd1v

13. Bas 510 F

14. Chebi:81822

15. Ncgc00163735-04

16. Anilide

17. Cantus

18. Bas 510f

19. Unii-32ms8zrd1v

20. 2-chloro-n-(4'-chloro[1,1'-biphenyl]-2-yl)-3-pyridinecarboxamide

21. 2-chloro-n-(4'-chloro(1,1'-biphenyl)-2-yl)-3-pyridinecarboxamide

22. 3-pyridinecarboxamide, 2-chloro-n-(4'-chloro(1,1'-biphenyl)-2-yl)-

23. Hsdb 7499

24. Boscalid [hsdb]

25. Emerald [inci]

26. Boscalid [mi]

27. Dsstox_cid_14392

28. Dsstox_rid_79152

29. Dsstox_gsid_34392

30. Schembl18517

31. Chembl1076544

32. Dtxsid6034392

33. Amy22452

34. Zinc3612929

35. Tox21_400045

36. 2-chloro-n-(4'-chloro[1,1'-biphenyl]-2-yl)pyridine-3-carboxamide

37. Boscalid 100 Microg/ml In Methanol

38. Mfcd06795150

39. Boscalid 10 Microg/ml In Cyclohexane

40. Akos015895938

41. Boscalid 1000 Microg/ml In Methanol

42. Boscalid 10 Microg/ml In Acetonitrile

43. Db12792

44. Ds-9792

45. Boscalid 100 Microg/ml In Acetonitrile

46. Ncgc00163735-01

47. Ncgc00163735-02

48. Ncgc00163735-03

49. Ncgc00163735-05

50. B4038

51. Boscalid, Pestanal(r), Analytical Standard

52. Cas-188425-85-6

53. Cs-0078856

54. Ft-0658358

55. C18547

56. 2-chloro-n-(4'-chloro-2-biphenylyl)nicotinamide

57. 425b856

58. A813228

59. Q894358

60. 2-chloro-n-(4'-chlorobiphenyl-2- Yl)-nicotinamide

61. J-012142

62. J-519930

2.4 Create Date
2005-08-09
3 Chemical and Physical Properties
Molecular Weight 343.2 g/mol
Molecular Formula C18H12Cl2N2O
XLogP34.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass342.0326684 g/mol
Monoisotopic Mass342.0326684 g/mol
Topological Polar Surface Area42 Ų
Heavy Atom Count23
Formal Charge0
Complexity399
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

Dermal Penetration (rat). Maximum % absorption: 0.01 mg/sq cm = 10.93 (24 hour exposure, 24 hour sacrifice) 0.10 mg/sq cm = 3.76 (24 hour exposure, 24 hour sacrifice) 1.00 mg/sq cm = 1.48 (10 hour exposure, 72 hour sacrifice /From table/

USEPA; Office of Prevention, Pesticides and Toxic Substances; Pesticide Fact Sheet - Boscalid. p.7 (July 2003). Available from, as of June 14, 2016: https://www3.epa.gov/


In the rat, Boscalid was readily absorbed and excreted following single oral 50 mg/kg; at single 500 mg/kg or 15 doses of 500 mg/kg, absorption was saturated. Excretion mainly by feces (80-98%). Biliary excretion 40- 50% of fecal activity at 50 mg/kg, 10% at 500 mg/kg. Urine, about 16% at 50 mg/kg, 3-5% at 500 mg/kg. Absorption about 56% at 50 mg/kg and 13-17% at 500 mg/kg. Excretory patterns similar by gender or radiolabel position. /From table/

USEPA; Office of Prevention, Pesticides and Toxic Substances; Pesticide Fact Sheet - Boscalid. p.7 (July 2003). Available from, as of June 14, 2016: https://www3.epa.gov/


4.2 Metabolism/Metabolites

Three ... groups of Wistar rats were treated and sampled ... for qualitative analyses of metabolites. ... Metabolites were separated by HPLC. Primary identification was by mass spectrometry (MS). ... The most important metabolites were hydroxyl or O-glucuronide metabolites on the diphenyl ring (usually para to the amide nitrogen), and S-glucuronide conjugation products displacing the chlorine on the pyridine ring of the parent compound. The sulfur originated from glutathione (GSH) addition to the ring. GSH was often cleaved to cysteine in bile or feces, or further degraded in feces to a thiol, which in turn was sometimes conjugated as a glucuronide). Tissue residues (liver, kidney, and plasma) were scant ... Some parent BAS 510 F was found in kidneys and plasma. Thus BAS 510 F was effectively metabolized and efficiently excreted.

California Environmental Protection Agency/Department of Pesticide Regulation; Summary of Toxicological Data for BAS 510 F, Chemical Code No.5790 p.9 (May 2, 2002, Revised May 20, 2013). Available from, as of June 15, 2016: https://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm


/In the rat,/ metabolites (hydroxylation and conjugation products) were consistent with Phase I oxidation reactions followed by Phase II conjugation with glucuronic acid or sulfate, or by conjugation of the parent with glutathione with cleavage to sulfate metabolites. /From table/

USEPA; Office of Prevention, Pesticides and Toxic Substances; Pesticide Fact Sheet - Boscalid. p.7 (July 2003). Available from, as of June 14, 2016: https://www3.epa.gov/


4.3 Biological Half-Life

In the rat, the predominant route of excretion of BAS 510 F is fecal with urinary excretion being minor. The half-life of BAS 510 F is less than 24 hours.

BASF Submission to EPA; Request for consideration of a tolerances for residues of Boscalid (BAS 510F). EPA-HQ-OPP-2005-0145-004 (EPA Docket) (2005)


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