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Chemistry

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Also known as: 23103-98-2, Pirimor, Pyrimor, Primicarbe, Aficida, Fernos
Molecular Formula
C11H18N4O2
Molecular Weight
238.29  g/mol
InChI Key
YFGYUFNIOHWBOB-UHFFFAOYSA-N
FDA UNII
1I93PS935T

Pirimicarb
Pirimicarb is a synthetic aminopyrimidine and tertiary amino compound, derived from a dimethylcarbamic acid, and carbamate acetylcholinesterase inhibitor that is used as pesticide. It is characterized as a colorless or white solid, and exposure occurs by inhalation, ingestion, or contact.
1 2D Structure

Pirimicarb

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-(dimethylamino)-5,6-dimethylpyrimidin-4-yl] N,N-dimethylcarbamate
2.1.2 InChI
InChI=1S/C11H18N4O2/c1-7-8(2)12-10(14(3)4)13-9(7)17-11(16)15(5)6/h1-6H3
2.1.3 InChI Key
YFGYUFNIOHWBOB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=C(N=C(N=C1OC(=O)N(C)C)N(C)C)C
2.2 Other Identifiers
2.2.1 UNII
1I93PS935T
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-dimethylamino-5,6-dimethylpyrimidin-4-yldimethylcarbamate

2. 5,6-dimethyl-2-dimethylamino-4-dimethylcarbamoyloxypyrimidine

3. Pirimor

4. Pyrimor

5. Zz-aphox

2.3.2 Depositor-Supplied Synonyms

1. 23103-98-2

2. Pirimor

3. Pyrimor

4. Primicarbe

5. Aficida

6. Fernos

7. Aphox

8. Rapid

9. Pirimor G

10. Pirimor Granulate

11. Pirimicarb Solution

12. Pirimicarbe

13. Abol

14. 2-(dimethylamino)-5,6-dimethylpyrimidin-4-yl Dimethylcarbamate

15. Ent-27766

16. Pp 062

17. Carbamic Acid, Dimethyl-, 2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl Ester

18. 2-dimethylamino-5,6-dimethyl-4-pyrimidinyl Dimethylcarbamate

19. Dimethylcarbamic Acid 2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl Ester

20. Chebi:8248

21. 5,6-dimethyl-2-dimethylamino-4-pyrimidinyldimethylcarbamate

22. 2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyldimethylcarbamate

23. 1i93ps935t

24. Pirimicarb 1000 Microg/ml In Acetone

25. Pirimicarb 10 Microg/ml In Acetonitrile

26. Pirimicarb 100 Microg/ml In Cyclohexane

27. Pirimicarb 100 Microg/ml In Acetonitrile

28. [2-(dimethylamino)-5,6-dimethylpyrimidin-4-yl] N,n-dimethylcarbamate

29. Pirimor 50 Dp

30. Caswell No. 359c

31. 2-dimethylamino-5,6-dimethylpyrimidin-4-yl Dimethylcarbamate

32. Pirimicarbe [iso-french]

33. Pirimicarb [ansi:bsi:iso]

34. Hsdb 7005

35. Einecs 245-430-1

36. Epa Pesticide Chemical Code 106101

37. Brn 0663442

38. Pyrimicarbe

39. Unii-1i93ps935t

40. Ai3-27766

41. Pirimicarb [mi]

42. Pirimicarb [iso]

43. Pirimicarb [hsdb]

44. 5,6-dwumetylo-2-dwumetyloamino-4-pirimidynylodwukarbaminian [polish]

45. Dsstox_cid_12569

46. Dsstox_rid_78989

47. Dsstox_gsid_32569

48. Schembl26523

49. 5-25-13-00063 (beilstein Handbook Reference)

50. Chembl1870931

51. Dtxsid1032569

52. Yfgyufniohwbob-uhfffaoysa-

53. 5,6-dwumetylo-2-dwumetyloamino-4-pirimidynylodwukarbaminian

54. 5,6-dimethyl-2-dimethylamino-4-dimethylcarbamoyloxypyrimidine

55. Zinc900772

56. 2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl Dimethylcarbamate

57. Oms 1330

58. Tox21_301003

59. 2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl N,n-dimethylcarbamate

60. Mfcd00055520

61. Akos015892522

62. Pirimicarb 100 Microg/ml In Methanol

63. Gs-3028

64. Ncgc00163704-01

65. Ncgc00163704-02

66. Ncgc00163704-03

67. Ncgc00254905-01

68. Cas-23103-98-2

69. Db-103794

70. Hy-119419

71. Cs-0068146

72. Ft-0655935

73. Pirimicarb, Pestanal(r), Analytical Standard

74. H10475

75. 103p982

76. A816567

77. Q419705

78. J-014990

79. (2-dimethylamino-5,6-dimethylpyrimidin-4-yl) N,n-dimethylcarbamate

80. 2-(dimethylamino)-5,6-dimethylpyrimidin-4-yl N,n-dimethylcarbamate

81. 2-dimethylamino-5,6-dimethylpyrimidin-4-yl N,n-dimethylcarbamate

82. [2-(dimethylamino)-5,6-dimethyl-pyrimidin-4-yl] N,n-dimethylcarbamate

83. Carbamic Acid, Dimethyl-, 2-(dimethylamino)-5,6-dimethyl-4-pyrimidyl Ester

84. Dimethyl-carbamic Acid 2-dimethylamino-5,6-dimethyl-pyrimidin-4-yl Ester

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 238.29 g/mol
Molecular Formula C11H18N4O2
XLogP31.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass238.14297583 g/mol
Monoisotopic Mass238.14297583 g/mol
Topological Polar Surface Area58.6 Ų
Heavy Atom Count17
Formal Charge0
Complexity270
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 MeSH Pharmacological Classification

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.)


4.2 Absorption, Distribution and Excretion

In rats given carbonyl-labeled [14C]pirimicarb by gavage or ip injection, >50% of the dose was expired as 14CO2 within 5 hr, & 15% was eliminated in the urine; essentially no residues were detected at sacrifice 8 days after admin. Up to 4 daily admins of pirimicarb to rats resulted in no accumulation in adipose tissue. In dogs, 86-94% of a ring-14C-labeled dose of pirimicarb was recovered, 79-88% in the urine & 6-7% in the feces; recovery was 74-86% after 1 day. Of a carbonyl-labeled dose to dogs, 15-26% was recovered, primarily in the urine; the unrecovered portion was thought to be expired rapidly as 14CO2. Of pirimicarb admin to a lactating dairy cow, 96% of the dose appeared in the urine, 4% in the feces, & <0.3% in the milk.

Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 3. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 1170


Mode of action: Selective systemic insecticide with contact, stomach, and respiratory action. Absorbed by the roots, and translocated through the xylem. Penetrates the leaves, but is not translocated extensively.

Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 820


4.3 Metabolism/Metabolites

Pirimicarb's major urinary metabolites in rats, dogs, & cows were similar, resulting from oxidative & hydrolytic mechanisms & consisting primarily of hydroxypyrimidines with modifications of the alkyl constituents of the heterocyclic moiety. Of the administered dose, 2-dimethylamino-5,6-dimethyl-4-hydroxypyrimidine accounted for 10-16.3%, 2-methylamino-5,6-dimethyl-4-hydroxypyrimidine for 20.5-41%, 2-amino-5,6-dimethyl-4-hydroxypyrimidine for 12.9-21%, & 2-dimethylamino-6-hydroxymethyl-5-methyl-4-hydroxypyrimidine for 1.8-5.7%. The major metabolites were eliminated unconjugated.

Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 3. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 1170


... During ... metabolism /of pirimicarb/ in mammals the carbamate moiety is hydrolyzed & subsequent demethylation at the dimethylamino group which is attached to the heterocyclic moiety results in the following major metabolites which are excreted in urine: 2-dimethylamino-5,6-dimethyl-4-hydroxypyrimidine (DDHP), 2-methylamino-5,6-dimethyl-4-hydroxypyrimidine (MDHP), & 2-amino-5,6-dimethyl-4-hydroxypyrimidine (ADHP). These metabolites were detected in every urine sample of seven workers who had applied pirimicarb. Concns of the 2-methylamino-5,6-dimethyl-4-hydroxypyrimidine & 2-amino-5,6-dimethyl-4-hydroxypyrimidine were much higher than that of 2-dimethylamino-5,6-dimethyl-4-hydroxypyrimidine indicating a considerable demethylation capacity in humans. No metabolites were found in urine specimens of controls. The investigated pyrimidines represent sensitive & specific parameters for biological monitoring of exposure to pirimicarb.

PMID:10414785 Hardt J, et al; Toxicol Lett 107 (1-3): 89-93 (1999)


4.4 Mechanism of Action

Cholinesterase inhibitor.

Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 820


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API | Excipient name

Pirimicarb

Synonyms

23103-98-2, Pirimor, Pyrimor, Primicarbe, Aficida, Fernos

Cas Number

23103-98-2

Unique Ingredient Identifier (UNII)

1I93PS935T

About Pirimicarb

Pirimicarb is a synthetic aminopyrimidine and tertiary amino compound, derived from a dimethylcarbamic acid, and carbamate acetylcholinesterase inhibitor that is used as pesticide. It is characterized as a colorless or white solid, and exposure occurs by inhalation, ingestion, or contact.

ABOL Manufacturers

A ABOL manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of ABOL, including repackagers and relabelers. The FDA regulates ABOL manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. ABOL API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

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A ABOL supplier is an individual or a company that provides ABOL active pharmaceutical ingredient (API) or ABOL finished formulations upon request. The ABOL suppliers may include ABOL API manufacturers, exporters, distributors and traders.

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ABOL Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

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