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Chemistry

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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

Chlorpropham
A carbamate that is used as an herbicide and as a plant growth regulator.
1 2D Structure

Chlorpropham

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 Weight 213.66 g/mol
Molecular Formula C10H12ClNO2
XLogP33.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass213.0556563 g/mol
Monoisotopic Mass213.0556563 g/mol
Topological Polar Surface Area38.3 Ų
Heavy Atom Count14
Formal Charge0
Complexity197
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

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... .

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 62 (1976)


...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.

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)


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


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API | Excipient name

Chlorpropham

Synonyms

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

Cas Number

101-21-3

Unique Ingredient Identifier (UNII)

0HBU04R8B0

About Chlorpropham

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

Chlorpropham Manufacturers

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

Chlorpropham Suppliers

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

click here to find a list of Chlorpropham suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Chlorpropham USDMF

A Chlorpropham DMF (Drug Master File) is a document detailing the whole manufacturing process of Chlorpropham active pharmaceutical ingredient (API) in detail. Different forms of Chlorpropham DMFs exist exist since differing nations have different regulations, such as Chlorpropham USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Chlorpropham DMF submitted to regulatory agencies in the US is known as a USDMF. Chlorpropham USDMF includes data on Chlorpropham's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Chlorpropham USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Chlorpropham suppliers with USDMF on PharmaCompass.

Chlorpropham GMP

Chlorpropham 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 Chlorpropham 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 Chlorpropham GMP manufacturer or Chlorpropham GMP API supplier for your needs.

Chlorpropham CoA

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

Chlorpropham CoA mostly includes findings from lab analyses of a specific batch. For each Chlorpropham 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.

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