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Chemistry

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Also known as: 63-25-2, Carbaril, Sevin, 1-naphthyl n-methylcarbamate, Naphthalen-1-yl methylcarbamate, 1-naphthyl methylcarbamate
Molecular Formula
C12H11NO2
Molecular Weight
201.22  g/mol
InChI Key
CVXBEEMKQHEXEN-UHFFFAOYSA-N
FDA UNII
R890C8J3N1

Carbaryl
A carbamate insecticide and parasiticide. It is a potent anticholinesterase agent belonging to the carbamate group of reversible cholinesterase inhibitors. It has a particularly low toxicity from dermal absorption and is used for control of head lice in some countries.
1 2D Structure

Carbaryl

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
naphthalen-1-yl N-methylcarbamate
2.1.2 InChI
InChI=1S/C12H11NO2/c1-13-12(14)15-11-8-4-6-9-5-2-3-7-10(9)11/h2-8H,1H3,(H,13,14)
2.1.3 InChI Key
CVXBEEMKQHEXEN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CNC(=O)OC1=CC=CC2=CC=CC=C21
2.2 Other Identifiers
2.2.1 UNII
R890C8J3N1
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-naphthyl-n-methylcarbamate

2. Antigale

3. Carbaril

4. Carbaryl, Manganese (2+) Salt

5. Carbaryl, Nickel (2+) Salt

6. Carbyl

7. Carylderm

8. Concentrat Vo 18

9. Dog Net Insecticide Poudre

10. Dog-net Insecticide Poudre

11. Dognet Insecticide Poudre

12. Fido's Free Itch

13. Fido's Free-itch

14. Fido's Freeitch

15. G Wizz

16. G-wizz

17. Gwizz

18. Insecticide Moureau, Poudre

19. Insecticide Vetoquinol, Poudre

20. Joseph Lyddy

21. Lyddy, Joseph

22. Moureau, Poudre Insecticide

23. Occoxil

24. Poudre Insecticide Moureau

25. Poudre Insecticide Vetoquinol

26. Poutic

27. Spou

28. Sevin

29. Skatta Tick Flea Louse Powder

30. Tigal

31. Vetoquinol, Poudre Insecticide

32. Vo 18, Concentrat

2.3.2 Depositor-Supplied Synonyms

1. 63-25-2

2. Carbaril

3. Sevin

4. 1-naphthyl N-methylcarbamate

5. Naphthalen-1-yl Methylcarbamate

6. 1-naphthyl Methylcarbamate

7. Arilat

8. Caprolin

9. Carbatox

10. Carbavur

11. Carylderm

12. Menaphtam

13. 1-naphthalenol, Methylcarbamate

14. Carbomate

15. Carpolin

16. Dicarbam

17. Karbaspray

18. Karbatox

19. Karbosep

20. Tricarnam

21. Arylam

22. Atoxan

23. Denapon

24. Gamonil

25. Hexavin

26. Monsur

27. Murvin

28. Ravyon

29. Seffein

30. Septene

31. Sevimol

32. Vioxan

33. Panam

34. Pomex

35. Suleo

36. Dyna-carbyl

37. Crag Sevin

38. Germain's

39. N-methyl-1-naphthyl Carbamate

40. Carbamine

41. Carbatox-60

42. Karbatox 75

43. Oltitox

44. Mugan

45. Vetox

46. Bercema Nmc50

47. Compound 7744

48. Naphthalen-1-yl N-methylcarbamate

49. Prosevor 85

50. Carbaril [inn]

51. Dicarbament 23,969

52. 1-naphthol N-methylcarbamate

53. Cekubaryl

54. Devicarb

55. Karbaryl

56. Olititox

57. Sevin 4

58. Crunch

59. Tercyl

60. Rylam

61. Savit

62. Toxan

63. 1-naphthalenyl Methylcarbamate

64. Bug Master

65. 1-naphthyl-n-methylcarbamate

66. Carbatox-75

67. N-methyl-alpha-naphthylurethan

68. Noflo 5 Vet

69. Karbaryl [polish]

70. Union Carbide 7,744

71. Karbatox Zawiesinowy

72. Oms-29

73. Alpha-naphthyl N-methylcarbamate

74. Carbarilo

75. Carbarilum

76. Caswell No. 160

77. Ent-23969

78. Experimental Insecticide 7744

79. Nmc 50

80. Carbatox 75

81. Methylcarbamate 1-naphthol

82. N-methyl-1-naftyl-carbamaat

83. N-metil-1-naftil-carbammato

84. Methylcarbamate 1-naphthalenol

85. N-methyl-1-naphthyl-carbamat

86. Methylcarbamic Acid, 1-naphthyl Ester

87. Sewin

88. N-methylcarbamate De 1-naphtyle

89. Uc 7744

90. 1-naphthalenol, 1-(n-methylcarbamate)

91. Nsc-27311

92. Carbamic Acid, Methyl-, 1-naphthyl Ester

93. Chembl46917

94. Chebi:3390

95. .alpha.-naftyl-n-methylkarbamat

96. .alpha.-naphthyl Methylcarbamate

97. N-methyl-.alpha.-naphthylurethan

98. R890c8j3n1

99. .alpha.-naphthyl N-methylcarbamate

100. N-methyl-.alpha.-naphthylcarbamate

101. .alpha.-naphthalenyl Methylcarbamate

102. Ncgc00090680-01

103. Derbac

104. Dsstox_cid_247

105. Carbaryl (sevin)

106. Dsstox_rid_75461

107. Dsstox_gsid_20247

108. Nac (insecticide)

109. Carbaril [italian]

110. Clinicide

111. Thinsec

112. Adios

113. Carbarilum [inn-latin]

114. Carbarilo [inn-spanish]

115. Carbaryl Solution

116. Latka 7744 [czech]

117. Nac (van)

118. Cas-63-25-2

119. Carbaryl [ansi:bsi:iso]

120. Alpha-naphthyl Methylcarbamate

121. Ccris 850

122. 1-naphthalenol Methylcarbamate

123. (14co)-carbaryl

124. Hsdb 952

125. Oms 29

126. 1433961-56-8

127. N-methyl-alpha-naphthylcarbamate

128. Alpha-naphthalenyl Methylcarbamate

129. O-(1-naphthyl)-n-methylcarbamat

130. Latka 7744

131. Einecs 200-555-0

132. Ent 23969

133. N-methyl Naphthylcarbamate

134. Naphthyl N-methylcarbamate

135. Nsc 27311

136. N-methyl-1-naftyl-carbamaat [dutch]

137. Alpha-naftyl-n-methylkarbamat [czech]

138. Ent 23,969

139. Epa Pesticide Chemical Code 056801

140. 1-naphthyl-n-methyl-karbamat [german]

141. N-methyl-1-naphthyl-carbamat [german]

142. N-metil-1-naftil-carbammato [italian]

143. Brn 1875862

144. Naphthalenol, Methylcarbamate

145. Alpha-naftyl-n-methylkarbamat

146. 1-naphthyl-n-methyl-karbamat

147. Laivin

148. N-methylcarbamate De 1-naphtyle [french]

149. Unii-r890c8j3n1

150. Ai3-23969

151. 1-naphthyl Methylcarbamate-14c

152. Sevin Sl

153. 1-naftylester Kyseliny Methylkarbaminove [czech]

154. Carbaryl (ban)

155. Vetox 85

156. 3197-92-0

157. 1-naftylester Kyseliny Methylkarbaminove

158. Union Carbide 7744

159. Carbaryl [hsdb]

160. Carbaryl [iarc]

161. Carbaryl [iso]

162. Carbaryl [mi]

163. Maybridge3_000390

164. Carbaryl [mart.]

165. Carbaril [who-dd]

166. Carbamic-14c Acid, Methyl-, 1-naphthyl Ester

167. Cid_6129

168. Wln: L66j Bovm1

169. Schembl26737

170. 27636-33-5

171. Carbamic Acid, Methyl-, Naphthalenyl Ester

172. Mls000851157

173. Bidd:er0592

174. Methylcarbamate, 1-naphthalenol

175. Zinc1090

176. Alpha-naphthyl-n-methylcarbamate

177. Dtxsid9020247

178. Cvxbeemkqhexen-uhfffaoysa-

179. Hms1432b16

180. Hms2809n24

181. Bcp18824

182. Hy-b1315

183. Nsc27311

184. 1-naphthyl-n-methylcarbamate, 97%

185. Tox21_110994

186. Tox21_201836

187. Tox21_300854

188. Bdbm50128572

189. Ccg-41182

190. Mfcd00021467

191. S5424

192. Stl371215

193. Carbamic Acid, N-methyl-1-naphthyl-

194. Carbaryl 10 Microg/ml In Cyclohexane

195. Akos001115604

196. Tox21_110994_1

197. Carbaryl 100 Microg/ml In Cyclohexane

198. Gs-3217

199. 1-naphthalenyl N-methylcarbamate

200. Idi1_011777

201. Flea And Tick Powder [veterinary] (tn)

202. Ncgc00090680-02

203. Ncgc00090680-03

204. Ncgc00090680-04

205. Ncgc00090680-05

206. Ncgc00090680-06

207. Ncgc00254757-01

208. Ncgc00259385-01

209. Carbamic Acid, N-methyl,1-naphthyl Ester

210. Smr000457400

211. Db-054440

212. C3742

213. Carbaryl, Pestanal(r), Analytical Standard

214. Cs-0013076

215. Ft-0608122

216. Ft-0664245

217. En300-06105

218. C07491

219. D07613

220. H11927

221. Ab00648589_06

222. 021c467

223. Q415090

224. Sr-01000631277

225. 1-naphthyl N-methylcarbamateacid O,o-diethyl Ester

226. Sr-01000631277-1

227. Sr-01000631277-3

228. Z90123586

229. Carbaryl Solution, 100 Mug/ml In Cyclohexane, Pestanal(r), Analytical Standard

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 201.22 g/mol
Molecular Formula C12H11NO2
XLogP32.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass201.078978594 g/mol
Monoisotopic Mass201.078978594 g/mol
Topological Polar Surface Area38.3 Ų
Heavy Atom Count15
Formal Charge0
Complexity230
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Formulations of carbaryl have been used successfully to control human lice.

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. 1152


/VETERINARY ANIMALS/ To control fleas, lice, ticks, & mites on animals, poultry, & premises, incl sarcoptic mange on buffaloes; lice, ticks, & mange mites on cattle; fleas & resistant fleas on dogs; & fowl mites, lice, & fleas on poultry.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 79


Medication (Vet): Ectoparasiticide

Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 290


5 Pharmacology and Biochemistry
5.1 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.)


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.)


5.2 Absorption, Distribution and Excretion

An in vitro dermal penetration study was conducted using both rat and human skin . This study showed that rat skin was 2.8 times more permeable to carbaryl than human skin.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision for Carbaryl. p 8 .EPA-738RO7-018 (September 2007) Available from, as of November 4, 2008: https://www.epa.gov/oppsrrd1/REDs/carbaryl_red.pdf


Excretion--retention of ... carbaryl labeled in 3 different positions ... studied 48 hr after ip admin to rats. 65% of (14)C of carbonyl-(14)C-carbaryl was excreted in urine, 25% in expired air, 2% in feces, & 10% was retained ... highest levels of (14)C were present in liver, kidneys, heart, & corpuscles (erythrocytes & leukocytes). 58% of (14)C of n-methyl-(14)C-carbaryl was excreted in urine, 12% in expired air, 4% in feces, & 13% was retained ... (14)C was maximal in liver, kidneys, heart, lungs, & spleen, organs with high blood flow. 77% of (14)C of naphthyl-(14)C-carbaryl was excreted in urine, 9% in feces, & 7% was retained ... levels of (14)C in tissue were highest in kidneys, spleen, bone, & fat ... about 50% of (14)C had been excreted in 4 hr ... .

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 81


Of oral dose of (1-naphthyl-1-(14)C)-N-methylcarbamate given to rats, 53% & 82% were absorbed after 20 min & 1 hr, respectively. Carbaryl is absorbed very rapidly from lung, 2.5 times faster than from small intestine.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V12 43 (1976)


(14)C-carbaryl labeled in n-methyl group has been found in fetuses of pregnant rats, & mice. ... Autoradiographic study of (14)C-methyl-carbaryl in pregnant rat has shown that radiolabel was localized in eye, liver, & brain of fetus.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 5: A Review of the Literature Published during 1976 and 1977. London: The Chemical Society, 1979., p. 458


For more Absorption, Distribution and Excretion (Complete) data for CARBARYL (9 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

Sevin, labeled with (14)C, is metabolized in insects, in rat, and by microsomal prepn of mouse, rat & rabbit liver, by aromatic hydroxylation, n-methyl hydroxylation, hydrolysis of carbamyl grouping, & by conjugation.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 205


Of the metabolites identified in livestock commodities, five are considered significant ... : carbaryl; 5,6-dihydro-5,6-dihydroxy carbaryl; and 5-methoxy-6-hydroxy carbaryl and all residues which can be hydrolyzed to carbaryl, 5,6-dihydro-5,6-dihydroxy carbaryl, or 5-methoxy-6-hydroxy carbaryl under acidic conditions. The /EPA/ included these compounds in the dietary risk assessment for carbaryl, and in the reassessment of carbaryl tolerances for livestock commodities only.

USEPA/Office of Pesticides Programs; Interim Reregistration Eligibility Decision for Carbaryl. p.12 (October 22, 2004) Available at https://www.epa.gov/oppsrrd1/REDs/carbaryl_ired.pdf on November 4, 2008


Single oral dose of carbaryl was admin to rats. After extraction of ... urine, column & TLC chromotography, tentative identification was made for 1,5-naphthalenediol with small amt of carbaryl, 5-hydroxycarbaryl, & trace of n-hydroxymethylcarbaryl was also present. A major metab ... identified as 5,6-dihydro-5,6-dihydroxycarbaryl, was found free (1.4% of the dose) & as the glucuronide (10.5% of the dose). Naphthyl glucuronide & sulfate were also observed.

Menzie, C. M. Metabolism of Pesticides, An Update. U.S. Department of the Interior, Fish, Wild-life Service, Special Scientific Report - Wildlife No. 184, Washington, DC: U.S. Government Printing Office, l974., p. 73


In urine of rats in addn to 1-naphthol, 1-naphthyl methylcarbamate N-glucuronide, 1-naphthyl methylimido-carbonate O-glucuronide, 4-(methylcarbamoyloxy)-1-naphthyl glucuronide, 1-naphthyl glucuronide, 1-naphthyl sulfate, 4-(methylcarbamoyloxy)-1-naphthyl sulfate, 3 unidentified cmpd & cmpd believed to be 1-naphthyl N-hydroxymethylcarbamate were observed. Similar results were observed with guinea pigs.

Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 72


For more Metabolism/Metabolites (Complete) data for CARBARYL (17 total), please visit the HSDB record page.


Carbaryl has known human metabolites that include 4-hydroxycarbaryl, 5-hydroxycarbaryl, and carbaryl methylol.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.4 Biological Half-Life

... The half-life of carbaryl was 6.4 min in the empty small intestines and 2.6 min in the lungs of rats.

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. 1146


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