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Chemistry

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Also known as: 22781-23-3, Bencarbate, Ficam, Dycarb, Niomil, Ficam w
Molecular Formula
C11H13NO4
Molecular Weight
223.22  g/mol
InChI Key
XEGGRYVFLWGFHI-UHFFFAOYSA-N
FDA UNII
QFH0ZU0A5U

Bendiocarb
Bendiocarb is a synthetic benzodioxole compound and carbamate acetylcholinesterase inhibitor that is used as a pesticide. It is characterized as a highly toxic, white, odorless crystalline solid, and exposure occurs by inhalation, ingestion, or contact.
1 2D Structure

Bendiocarb

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2,2-dimethyl-1,3-benzodioxol-4-yl) N-methylcarbamate
2.1.2 InChI
InChI=1S/C11H13NO4/c1-11(2)15-8-6-4-5-7(9(8)16-11)14-10(13)12-3/h4-6H,1-3H3,(H,12,13)
2.1.3 InChI Key
XEGGRYVFLWGFHI-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1(OC2=C(O1)C(=CC=C2)OC(=O)NC)C
2.2 Other Identifiers
2.2.1 UNII
QFH0ZU0A5U
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ficam

2. Ficam 80w

3. Ficam W

2.3.2 Depositor-Supplied Synonyms

1. 22781-23-3

2. Bencarbate

3. Ficam

4. Dycarb

5. Niomil

6. Ficam W

7. Multamat

8. Garvox

9. Turcam

10. Bendiocarbamate

11. Multimet

12. Rotate

13. Tattoo

14. Tatoo

15. Seedox 80w

16. Ficam D

17. Ficam Ulv

18. Fisons Nc 6897

19. Bendiocarbe

20. 2,2-dimethyl-1,3-benzodioxol-4-ol Methylcarbamate

21. 2,2-dimethyl-1,3-benzodioxol-4-yl Methylcarbamate

22. Oms-1394

23. 1,3-benzodioxol-4-ol, 2,2-dimethyl-, Methylcarbamate

24. (2,2-dimethyl-1,3-benzodioxol-4-yl) N-methylcarbamate

25. Chebi:34556

26. 2,2-dimethyl-1,3-benzodioxol-4-yl N-methylcarbamate

27. 2,3-isopropylidene-dioxyphenyl Methylcarbamate

28. Methylcarbamic Acid 2,3-(isopropylidenedioxy)phenyl Ester

29. Qfh0zu0a5u

30. 2,2-dimethylbenzo-1,3-dioxol-4-yl Methylcarbamate

31. 2,2-dimethyl-1,3-benzdioxol-4-yl N-methylcarbamate

32. 1,3-benzodioxole, 2,2-dimethyl-4-(n-methylcarbamato)-

33. 1,3-benzodioxole, 2,2-dimethyl-4-(n-methylaminocarboxylato)-

34. Carbamic Acid, Methyl-, 2,3-(isopropylidenedioxy)phenyl Ester

35. Carbamic Acid, Methyl-, 2,3-(dimethylmethylenedioxy)phenyl Ester

36. Ficam 80w

37. 2,2-dimethylbenzo[d][1,3]dioxol-4-yl Methylcarbamate

38. 2,3-isopropylidenedioxyphenyl Methylcarbamate

39. Ficam B

40. Ficam Ulv' Ul

41. Ficam Z

42. Dsstox_cid_12327

43. Dsstox_rid_78914

44. Dsstox_gsid_32327

45. 2,2-dimethyl-4-(methylcarbamoyloxy)-1,3-benzodioxole

46. 1,3-benzodioxol-4-ol,2,2-dimethyl-, 4-(n-methylcarbamate)

47. Seedoxin

48. Sedox

49. Bendiocarbe [iso-french]

50. Bendiocarb [ansi:bsi:iso]

51. Cas-22781-23-3

52. Ccris 9062

53. Hsdb 3918

54. Einecs 245-216-8

55. Unii-qfh0zu0a5u

56. Nc6897

57. Rcra Waste No. U278

58. Epa Pesticide Chemical Code 105201

59. Nc 6897

60. Brn 1315404

61. Fuam

62. Ai3-27695

63. 2,2-dimethyl-1,3-benzodioxole-n-methylcarbamate

64. Garvox 3g

65. 1,3-benzodioxol-4-ol, 2,2-dimethyl-, Methyl Carbamate

66. Ficam 80 W

67. Spectrum_001917

68. Bendiocarb [mi]

69. Specplus_000548

70. Ficam Plus (salt/mix)

71. Bendiocarb [iso]

72. Spectrum2_001726

73. Spectrum3_000854

74. Spectrum4_000694

75. Spectrum5_002026

76. Bendiocarb [hsdb]

77. Bendiocarb [mart.]

78. Schembl22080

79. Bspbio_002467

80. Kbiogr_001187

81. Kbioss_002459

82. Spectrum330063

83. Mls002695990

84. Divk1c_006644

85. Spbio_001772

86. Chembl465018

87. Dtxsid9032327

88. Kbio1_001588

89. Kbio2_002452

90. Kbio2_005020

91. Kbio2_007588

92. Kbio3_001967

93. Xeggryvflwgfhi-uhfffaoysa-

94. Hms3087c14

95. Zinc2015426

96. Tox21_201562

97. Tox21_300777

98. Bdbm50064618

99. Ccg-39499

100. Akos015888418

101. Ncgc00094543-01

102. Ncgc00094543-02

103. Ncgc00094543-03

104. Ncgc00094543-04

105. Ncgc00094543-05

106. Ncgc00094543-06

107. Ncgc00094543-07

108. Ncgc00254681-01

109. Ncgc00259111-01

110. Smr000777869

111. Db-045987

112. Bendiocarb, Pestanal(r), Analytical Standard

113. F21336

114. 781b233

115. Q417017

116. J-014852

117. 2,2-dimethyl-1,3-benzodioxol-4-yl Methylcarbamate #

118. 2,2-dimethyl-2h-1,3-benzodioxol-4-yl N-methylcarbamate

119. Carbamic Acid, N-methyl-, 2,3-isopyridenyldioxyphenyl Ester

120. 6,8-dichloro-3-ethyl-2h-benzo[e][1,2,4]thiadiazine 1,1-dioxide

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 223.22 g/mol
Molecular Formula C11H13NO4
XLogP31.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass223.08445790 g/mol
Monoisotopic Mass223.08445790 g/mol
Topological Polar Surface Area56.8 Ų
Heavy Atom Count16
Formal Charge0
Complexity279
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 a 1 mg/kg oral dose of (14)C bendiocarb, plasma levels of radioactivity peaked at 10 min after administration. Following a 2.5 mg/kg dose, radioactivity in the tissues 72 hr after administration ranged from 0.015 to 0.061 ppm (as bendiocarb). Six days after 10 day dietary administration of ring-labeled bendiocarb to rats ended, residues were detected in the fat, liver, kidneys, muscle, and brain, the levels being highest in the fat tissue. ... Within 2 days after oral administration of ring-labeled bendiocarb (at 0.125-10 mg/kg) to rats, 89-90% of the dose was eliminated in the urine, 2-6% in the expired air, and 2-6% in the feces. ...

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. 1143


In rats and a range of other mammals, rapidly absorbed following oral admin or inhalation, but not following skin contact. Rapidly detoxified and eliminated almost completely within 24 hr as the sulfate and glucuronide conjugate of the principal metabolite, 2,2-dimethyl-1,3-benzodioxol-4-ol.

Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 76


Bendiocarb may be absorbed from the gastrointestinal tract or to a limited extent through the intact skin. Low vapor pressure makes inhalation unlikely except from airborne spray mist.

WHO/FAO; Pesticide Data Sheet (PDS) 52: Bendiocarb. Available from, as of September 3, 2013: https://www.inchem.org/pages/pds.html


Male and female rats treated with a single oral dose of (14)C-bendiocarb at approximately 10 mg/kg body weight eliminated over 95% of the administered radioactivity in urine (89%), expired air (6%) and feces (2%) within 2 days of dosing. There was no significant sex different in rate and route of elimination.

WHO/FAO; Joint Meeting on Pesticide Residues: Pesticide Residues in Food - 1982 for Bendiocarb (22781-23-3) (1982). Available from, as of September 3, 2013: https://www.inchem.org/pages/jmpr.html


For more Absorption, Distribution and Excretion (Complete) data for BENDIOCARB (7 total), please visit the HSDB record page.


4.3 Metabolism/Metabolites

Metabolism ... of an oral dose of (14)C bendiocarb by a human subject was similar to the pattern observed in animals; primarily as sulfate and glucuronide conjugates of the phenol, with minor amounts of conjugated bendiocarb and N-hydroxymethyl bendiocarb.

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. 1143


In all species examined, bendiocarb was metabolized via cleavage of the carbamate ester group to yield the phenol (2,2-dimethyl-1,3-benzoxodiol-4-ol), which was excreted as sulfate and glucuronide conjugates.

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. 1143


Spontaneous hydrolysis of the carbamate-cholinesterase complex occurs in vivo, leading to the disappearance of clinical effects within 24 hr. /Carbamate pesticides/

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 1077


Bendiocarb is readily conjugated and metabolized by liver microsome enzymes, it is rapidly excreted, mainly as sulfate and beta-glucuronide conjugates of the phenol derivative.

WHO/FAO; Pesticide Data Sheet (PDS) 52: Bendiocarb. Available from, as of September 3, 2013: https://www.inchem.org/pages/pds.html


For more Metabolism/Metabolites (Complete) data for BENDIOCARB (11 total), please visit the HSDB record page.


4.4 Biological Half-Life

In a male volunteer given a single oral dose of 9.8 mg or approximately 0.12 mg/kg of (14)C-bendiocarb, over 99% of the administered dose was excreted in the urine in 22 hours. The plasma half-life and the half-life for renal elimination for total radioactivity was estimated at 3.5 and 3.3 hours, respectively. ...

WHO/FAO; Joint Meeting on Pesticide Residues: Pesticide Residues in Food - 1982 for Bendiocarb (22781-23-3) (1982). Available from, as of September 3, 2013: https://www.inchem.org/pages/jmpr.html


Following an acute oral dose of (14)C-bendiocarb at 1 mg/kg body weight, plasma levels in male and female rats peaked at 10 minutes post treatment with plasma half-life being calculated at 4.4 hours for both sexes.

WHO/FAO; Joint Meeting on Pesticide Residues: Pesticide Residues in Food - 1982 for Bendiocarb (22781-23-3) (1982). Available from, as of September 3, 2013: https://www.inchem.org/pages/jmpr.html


In a male volunteer given a single oral dose of 9.8 mg or approximately 0.12 mg/kg of (14)C-bendiocarb, over 99% of the administered dose was excreted in the urine in 22 hours. The plasma half-life and the half-life for renal elimination for total radioactivity was estimated at 3.5 and 3.3 hours, respectively. ...

WHO/FAO; Joint Meeting on Pesticide Residues: Pesticide Residues in Food - 1982 for Bendiocarb (22781-23-3) (1982). Available from, as of September 3, 2013: https://www.inchem.org/pages/jmpr.html


Bendiocarb acts through inhibition of cholinesterase activity which is rapidly reversible, the half-life of the inhibited enzyme is approximately 30 minutes.

WHO/FAO; Pesticide Data Sheet (PDS) 52: Bendiocarb. Available from, as of September 3, 2013: https://www.inchem.org/pages/pds.html


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API | Excipient name

Bendiocarb

Synonyms

22781-23-3, Bencarbate, Ficam, Dycarb, Niomil, Ficam w

Cas Number

22781-23-3

Unique Ingredient Identifier (UNII)

QFH0ZU0A5U

About Bendiocarb

Bendiocarb is a synthetic benzodioxole compound and carbamate acetylcholinesterase inhibitor that is used as a pesticide. It is characterized as a highly toxic, white, odorless crystalline solid, and exposure occurs by inhalation, ingestion, or contact.

Bendiocarb Manufacturers

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

Bendiocarb Suppliers

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

Bendiocarb GMP

Bendiocarb 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).

PharmaCompass offers a list of Bendiocarb GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Bendiocarb GMP manufacturer or Bendiocarb GMP API supplier for your needs.

Bendiocarb CoA

A Bendiocarb CoA (Certificate of Analysis) is a formal document that attests to Bendiocarb's compliance with Bendiocarb specifications and serves as a tool for batch-level quality control.

Bendiocarb CoA mostly includes findings from lab analyses of a specific batch. For each Bendiocarb CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Bendiocarb may be tested according to a variety of international standards, such as European Pharmacopoeia (Bendiocarb EP), Bendiocarb JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Bendiocarb USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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