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PREVENTOL

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Also known as: 101-21-3, Chloropropham, Cipc, Chloro-ipc, Isopropyl n-(3-chlorophenyl)carbamate, Chlorprophame

Molecular Formula

C₁₀H₁₂ClNO₂

Molecular Weight

213.66 g/mol

InChI Key

CWJSHJJYOPWUGX-UHFFFAOYSA-N

FDA UNII

0HBU04R8B0

A carbamate that is used as an herbicide and as a plant growth regulator.

1 2D Structure

PREVENTOL

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

propan-2-yl N-(3-chlorophenyl)carbamate

2.1.2 InChI

InChI=1S/C10H12ClNO2/c1-7(2)14-10(13)12-9-5-3-4-8(11)6-9/h3-7H,1-2H3,(H,12,13)

2.1.3 InChI Key

CWJSHJJYOPWUGX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)OC(=O)NC1=CC(=CC=C1)Cl

2.2 Other Identifiers

2.2.1 UNII

0HBU04R8B0

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cipc

2. Isopropyl N-(3-chlorophenol)carbamate

2.3.2 Depositor-Supplied Synonyms

1. 101-21-3

2. Chloropropham

3. Cipc

4. Chloro-ipc

5. Isopropyl N-(3-chlorophenyl)carbamate

6. Chlorprophame

7. Elbanil

8. Metoxon

9. Nexoval

10. Preweed

11. Taterpex

12. Furloe

13. Isopropyl (3-chlorophenyl)carbamate

14. Isopropyl M-chlorocarbanilate

15. Stopgerme-s

16. Sprout Nip

17. Chloripc

18. Spud-nic

19. Spud-nie

20. Chloro-ifk

21. Triherbicide Cipc

22. Preventol 56

23. Prevenol 56

24. Liro Cipc

25. Isopropyl 3-chlorocarbanilate

26. Mirvale

27. Fasco Wy-hoe

28. Furloe 3 Ec

29. Keim-stop

30. Isopropyl 3-chlorophenylcarbamate

31. Isopropyl N-(m-chlorophenyl)carbamate

32. Ci-ipc

33. Chlor Ifc

34. Chlor Ifk

35. Carbamic Acid, (3-chlorophenyl)-, 1-methylethyl Ester

36. Cl-ifk

37. Jack Wilson Chloro 51(oil)

38. N-(3-chlorophenyl)isopropyl Carbamate

39. N-3-chlorophenylisopropylcarbamate

40. 3-chlorocarbanilic Acid, Isopropyl Ester

41. Isopropyl-m-chlorocarbanilate

42. Isopropyl-n-(3-chlorophenyl)carbamate

43. Isopropyl Meta-chlorocarbanilate

44. Ent 18,060

45. Isopropyl N-chlorophenylcarbamate

46. O-isopropyl N-(3-chlorophenyl)carbamate

47. N-(3-chlorophenyl)carbamic Acid, Isopropyl Ester

48. (3-chlorophenyl)carbamic Acid, 1-methylethyl Ester

49. Carbanilic Acid, M-chloro-, Isopropyl Ester

50. Isopropyl-n-m-chlorophenyl-carbamate

51. Isopropyl-n-3-chlorophenyl Carbamate

52. M-chlorocarbanilic Acid Isopropyl Ester

53. N-(3-chlor-phenyl)-isopropyl-carbamat

54. 1-methylethyl (3-chlorophenyl)carbamate

55. N-(3-chloor-fenyl)-isopropyl Carbamaat

56. N-(3-cloro-fenil)-isopropil-carbammato

57. M-chlorocarbanilic Acid, Isopropyl Ester

58. Isopropyl-n-(3-chlorphenyl)-carbamat

59. Propan-2-yl N-(3-chlorophenyl)carbamate

60. 0hbu04r8b0

61. Y 3

62. Chebi:34630

63. Nsc-29466

64. Chlorpropham 100 Microg/ml In Methanol

65. Chlorpropham 10 Microg/ml In Acetonitrile

66. N-(3-chloro Phenyl)carbamate D'isopropyle

67. Chlorpropham 100 Microg/ml In Acetonitrile

68. Dsstox_cid_764

69. Sprout-nip Ec

70. Unicrop Cipc

71. Bud Nip

72. Bud-nip

73. Chloro Ipc

74. Chlor Ipc

75. Chlor-ifc

76. Dsstox_rid_75778

77. Dsstox_gsid_20764

78. Furloe 3ec

79. Furloe 4ec

80. Caswell No. 510a

81. Chlorprophame [french]

82. Ci-ifk

83. Chlorpropham [bsi:iso]

84. Chlorprophame [iso-french]

85. Cas-101-21-3

86. Chlorpropham [iso]

87. Hsdb 981

88. Einecs 202-925-7

89. Nsc 29466

90. 1-methylethyl(3-chlorophenyl)carbamate

91. Epa Pesticide Chemical Code 018301

92. Brn 2211397

93. Unii-0hbu04r8b0

94. Ai3-18060

95. Ccris 9259

96. Isopropyl-n-(3-chlorphenyl)-carbamat [german]

97. N-(3-chloor-fenyl)-isopropyl Carbamaat [dutch]

98. N-(3-chlor-phenyl)-isopropyl-carbamat [german]

99. N-(3-cloro-fenil)-isopropil-carbammato [italian]

100. N-(3-chloro Phenyl) Carbamate D'isopropyle [french]

101. Propan-2-yl (3-chlorophenyl)carbamate

102. Isopropyl-n-(3-chlorophenyl) Carbamate

103. Prevenol (salt/mix)

104. Spectrum_001883

105. Gro Stop (salt/mix)

106. Specplus_000504

107. N-(3-chloro Phenyl) Carbamate D'isopropyle

108. Spectrum2_000044

109. Spectrum3_000842

110. Spectrum4_000682

111. Spectrum5_002000

112. Chlorpropham [mi]

113. Isopropyl Chlorocarbanilate

114. Chlorpropham [hsdb]

115. Schembl54464

116. Bspbio_002423

117. Kbiogr_001143

118. Kbioss_002413

119. Spectrum330051

120. Bidd:er0253

121. Divk1c_006600

122. Isopropyl M-chloro Carbanilate

123. Spbio_000167

124. Chembl104560

125. Dtxsid7020764

126. Schembl22437601

127. Kbio1_001544

128. Kbio2_002407

129. Kbio2_004975

130. Kbio2_007543

131. Kbio3_001923

132. Wln: Gr Cmvoy1 & 1

133. Zinc57368

134. Chlorpropham, ~95%, Crystalline

135. Nsc29466

136. Tox21_201866

137. Tox21_301139

138. Ccg-39995

139. Mfcd00037108

140. Akos003369049

141. Cs-w014956

142. Hy-w014240

143. Ks-5118

144. Ncgc00094538-01

145. Ncgc00094538-02

146. Ncgc00094538-03

147. Ncgc00094538-04

148. Ncgc00094538-05

149. Ncgc00094538-06

150. Ncgc00094538-07

151. Ncgc00255037-01

152. Ncgc00259415-01

153. Ac-11051

154. Chlorpropham 1000 Microg/ml In N-hexane

155. Nci60_002445

156. Ft-0631534

157. 01c213

158. D97609

159. Chlorpropham, Pestanal(r), Analytical Standard

160. N-(3-chlorophenyl)carbamic Acid Isopropyl Ester

161. 1-methylethyl N-(3-chlorophenyl)carbamate

162. A851706

163. Q904901

164. J-000342

165. Brd-k59590127-001-02-9

166. Carbamic Acid, N-(3-chlorophenyl)-, 1-methylethyl Ester

167. Chlorpropham Solution, 100 Mug/ml In Acetonitrile, Pestanal(r), Analytical Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₂ClNO₂
Molecular Weight	213.66 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Exact Mass	213.0556563 g/mol
Monoisotopic Mass	213.0556563 g/mol
Topological Polar Surface Area	38.3 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	197
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Herbicides

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)

Plant Growth Regulators

Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins. (See all compounds classified as Plant Growth Regulators.)

4.2 Absorption, Distribution and Excretion

After oral or ip administration of (14)C isopropyl and (14)C ring-labelled chloropropham to rats, 4 day urinary excretions were 50 and 85% of dose, respectively for two sites of labelling; in case of isopropyl-labelled compound, an additional 17-20% of dose was excreted as CO2 via lungs. ...When pregnant rats were given (14)C chloropropham, radioactivity was readily transferred to fetuses, and its level did not decline in fetal tissues as rapidly as it did in maternal organs. Pups of lactating rats that were given labelled chloropropham also contained radioactivity.

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 61 (1976)

In Wistar rats given single oral dose of labeled chlorpropham average urinary excretions of radioactivity were 55.9% and 82.6% of chain (14)C CIPC and ring (14)C CIPC. With chain CIPC 35.4 + or - 7.5% of administered dose was excreted in respired air.

Fang SC et al; Pestic Biochem Physiol 4 (1): 1-11 (1974)

Dermal absorption is not significant.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-327

Chlorpropham or its metabolites are readily transported acropetally following root absorption and may be transported basipetally from foliar application in some plants. ...Polar metabolites are not translocated once they are formed in either roots or shoots.

Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 104

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

4.3 Metabolism/Metabolites

In rats, most important metabolic transformation of chloropropham is hydroxylation in the para-position and conjugation of the resulting 4-hydroxychloropropham with sulfate. Hydroxylation of the isopropyl residue accounts for about 1/3 of the metabolism of this herbicide. ...Approximately 4 times more monohydroxy compound than dihydroxy compound were detected. Compound undergoes further oxidation... hydrolytic fission... yields meta-chloroaniline, carbon dioxide and isopropanol, which is further oxidized to acetone and carbon dioxide. Hydroxylation of... meta-chloroaniline also takes place to give N-acetyl-4-amino-2-chlorophenol... plus N-acetyl-2-amino-4-chlorophenol... .

...It was... suggested that chlorpropham... metabolized differently between sensitive and resistant plants. ...Intact carbamates /found/ in sensitive plants... were not observed in resistant plant.

Kearney, P.C., and D. D. Kaufman (eds.) Herbicides: Chemistry, Degredation and Mode of Action. Volumes 1 and 2. 2nd ed. New York: Marcel Dekker, Inc., 1975., p. 654

Hydrolysis of carbamate linkage occurred in neomycin treated rats, and in vitro investigation suggested that liver is site of hydrolysis.

Following oral administration... to rats, renal excretion was followed. ...Although the expected hydrolysis products were not found free, n-acetyl hydroxyl analogs were excreted and identified. The 1-carbethoxy compound and a metabolite believed to be 1-hydroxypropyl-2-n-(3-chloro-4-hydroxyphenyl) carbamate was found... after root treatment of soybean plants with CIPC, polar metabolites of CIPC from root and shoot tissues were isolated and purified. Data showed major root metabolite was o-glucoside of 2-hydroxy CIPC. This was also found in shoots... .

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. 106

For more Metabolism/Metabolites (Complete) data for CHLORPROPHAM (15 total), please visit the HSDB record page.

4.4 Biological Half-Life

...The average biological half-life of 14C from both compounds in most organs /of rats administered an oral dose of 14C-labelled propham or chloropropham/ was short, ranging from 3-8 hr. However, in brain, fat, and muscle, the half-life was about twice this value.

WHO; Environ Health Criteria 64: Carbamate Pesticides: A General Introduction (1986). Available from, as of February 17, 2005: https://www.inchem.org/documents/ehc/ehc/ehc64.htm