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Tox21_301016
Also known as: 330-54-1, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, Dcmu, Duran, Dynex, Dichlorfenidim
Molecular Formula
C9H10Cl2N2O
Molecular Weight
233.09  g/mol
InChI Key
XMTQQYYKAHVGBJ-UHFFFAOYSA-N
FDA UNII
9I3SDS92WY

A pre-emergent herbicide.
1 2D Structure

Tox21_301016

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-(3,4-dichlorophenyl)-1,1-dimethylurea
2.1.2 InChI
InChI=1S/C9H10Cl2N2O/c1-13(2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14)
2.1.3 InChI Key
XMTQQYYKAHVGBJ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C)C(=O)NC1=CC(=C(C=C1)Cl)Cl
2.2 Other Identifiers
2.2.1 UNII
9I3SDS92WY
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-(3,4-dichlorophenyl)-1,1-dimethylurea

2. Dcmu

2.3.2 Depositor-Supplied Synonyms

1. 330-54-1

2. 3-(3,4-dichlorophenyl)-1,1-dimethylurea

3. Dcmu

4. Duran

5. Dynex

6. Dichlorfenidim

7. Herbatox

8. Vonduron

9. Dailon

10. Karmex

11. Marmer

12. Karmex Dw

13. Di-on

14. Cekiuron

15. Crisuron

16. Lucenit

17. Unidron

18. 1,1-dimethyl-3-(3,4-dichlorophenyl)urea

19. Diuron Nortox

20. Karmex D

21. Karmex Diuron Herbicide

22. 1-(3,4-dichlorophenyl)-3,3-dimethylurea

23. N'-(3,4-dichlorophenyl)-n,n-dimethylurea

24. Preventol A 6

25. Urox D

26. Diuron 4l

27. Direx 4l

28. Dp Hardener 95

29. Telvar Diuron Weed Killer

30. Urea, N'-(3,4-dichlorophenyl)-n,n-dimethyl-

31. N-(3,4-dichlorophenyl)-n',n'-dimethylurea

32. Dcmu 99

33. Hw 920

34. Karamex

35. N,n,-dimethyl-n'-(3,4-dichlorophenyl)urea

36. Urea, 3-(3,4-dichlorophenyl)-1,1-dimethyl-

37. 3-(3,4-dichlor-phenyl)-1,1-dimethyl-harnstoff

38. 1-(3,4-dichlorophenyl)-3,3-dimethyluree

39. Chebi:116509

40. 9i3sds92wy

41. 3-(3,4-dichlorophenyl)-1,1-dimethyl-urea

42. 3-(3,4-dicloro-fenyl)-1,1-dimetil-urea

43. 3-(3,4-dichloor-fenyl)-1,1-dimethylureum

44. Dtxsid0020446

45. Nsc-8950

46. Ncgc00094525-01

47. Anduron

48. Ansaron

49. Dirurol

50. Durashield

51. Herburon

52. Seduron

53. Bioron

54. Drexel

55. Farmco Diuron

56. Dsstox_cid_446

57. 3-(3,4-dichloro-phenyl)-1,1-dimethyl-urea

58. Sup'r Flo

59. Dsstox_rid_75595

60. Dsstox_gsid_20446

61. Diuron 900

62. Caswell No. 410

63. Ditox-800

64. Aguron

65. Diater

66. Diuron Solution

67. Dichlorfenidim [russian]

68. Usaf P-7

69. Diuron [ansi:bsi:iso]

70. Usaf Xr-42

71. Cas-330-54-1

72. Diuron [iso]

73. Ccris 1012

74. Hsdb 382

75. Direx 80w

76. Nsc 8950

77. Einecs 206-354-4

78. Af 101

79. Unii-9i3sds92wy

80. Epa Pesticide Chemical Code 035505

81. Brn 2215168

82. Xarmex

83. N-(3,4-dichlorophenyl)-n,n-dimethylurea

84. Ai3-61438

85. Karmex Dl

86. 1-(3,4-dichlorophenyl)-3,3-dimethyluree [french]

87. 3-(3,4-dichloor-fenyl)-1,1-dimethylureum [dutch]

88. 3-(3,4-dicloro-fenyl)-1,1-dimetil-urea [italian]

89. Karmex 80w

90. Mfcd00018136

91. 3-(3,4-dichlor-phenyl)-1,1-dimethyl-harnstoff [german]

92. Spectrum_001823

93. 1-(3,3-dimethylurea

94. 3-(3,1-dimethylurea

95. Specplus_000424

96. N'-(3,n-dimethylurea

97. N-(3,n'-dimethylurea

98. 1,4-dichlorophenyl)urea

99. 3-(3,1-dimethylureum

100. Diuron [hsdb]

101. N,n-dimethyl-n'-(3,4-dichlorophenyl)urea

102. 3-(3,1-dimetil-urea

103. Spectrum2_001229

104. Spectrum3_000822

105. Spectrum4_000662

106. Spectrum5_001956

107. Diuron [mi]

108. Diuron, >=98%

109. Ec 206-354-4

110. Cambridge Id 5104305

111. Schembl7279

112. 3-(3,1-dimethyl-harnstoff

113. Bspbio_002343

114. Kbiogr_001063

115. Kbioss_002328

116. Spectrum330030

117. Mls002207110

118. Divk1c_006520

119. Spbio_001078

120. Chembl278489

121. Kbio1_001464

122. Kbio2_002325

123. Kbio2_004893

124. Kbio2_007461

125. Kbio3_001843

126. Zinc57287

127. Nsc8950

128. Wln: Gr Bg Dmvn1 & 1

129. Diuron 100 Microg/ml In Methanol

130. Hy-b0860

131. Tox21_111292

132. Tox21_201438

133. Tox21_301016

134. Bdbm50487027

135. Ccg-39151

136. Diuron 10 Microg/ml In Acetonitrile

137. Stk077954

138. Akos001303464

139. Diuron 100 Microg/ml In Acetonitrile

140. Tox21_111292_1

141. Urea,4-dichlorophenyl)-n,n-dimethyl-

142. Urea,4-dichlorophenyl)-1,1-dimethyl-

143. Ncgc00094525-02

144. Ncgc00094525-03

145. Ncgc00094525-04

146. Ncgc00094525-05

147. Ncgc00094525-06

148. Ncgc00094525-07

149. Ncgc00094525-08

150. Ncgc00094525-09

151. Ncgc00254918-01

152. Ncgc00258989-01

153. As-15493

154. Smr000777941

155. Diuron, Pestanal(r), Analytical Standard

156. 3-(3,4-dichlorophenol)-1,1-dimethylurea

157. Db-048327

158. Cs-0012874

159. D1328

160. Ft-0603378

161. Ft-0667750

162. N,n-dimethyl-n'-(3,4-dichlorophenyl)-urea

163. N-(3,4-dichlorophenyl)-n',n'-dimethyl Urea

164. C18428

165. A821585

166. Q425389

167. Sr-01000195223

168. Diuron, Certified Reference Material, Tracecert(r)

169. J-018992

170. Sr-01000195223-1

171. Brd-k75330923-001-02-6

172. Diuron Solution, 100 Mug/ml In Acetonitrile, Pestanal(r), Analytical Standard

173. W9m

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 233.09 g/mol
Molecular Formula C9H10Cl2N2O
XLogP32.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass232.0170183 g/mol
Monoisotopic Mass232.0170183 g/mol
Topological Polar Surface Area32.3 Ų
Heavy Atom Count14
Formal Charge0
Complexity211
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.)


4.2 Absorption, Distribution and Excretion

Diuron is readily absorbed through the gastrointestinal tract in rats and dogs. Tissue level of diuron were positively correlated with dosage. No apparent storage of diuron in tissues was noted ... Diuron is also partially excreted unchanged in feces and urine.

Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 2, 2nd ed. 2001. Academic Press, San Diego, California., p. 1522


Root uptake of (14)C-Diuron from solution was studied. ... small amount of the monomethyl and demethylated derivatives were found in nutrient solution from ... soybeans, ... oat, and corn tops.

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. 338


Diuron is most readily absorbed through the root system; less so through foliage & stems. Translocation is primarily upward in xylem.

Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 205


Diuron was fed to five dairy cows at 0-550 ppm concentration levels. About 50% of the diuron was detected in the urine, 10% in the feces and 5% in the blood. Milk samples did not contain diuron. A positive correlation was noted between the concn of diuron products in urine and blood and a negative correlation between urine and feces. It is suggested that the remaining diuron is absorbed in the body or degraded into undetectable metabolites.

PMID:535556 Kalra SK, Chahal KS; Ecotoxicol Environ Saf 3 (4): 362-8 (1979)


4.3 Metabolism/Metabolites

Diuron is carcinogenic to the rat urinary bladder at high dietary levels. The proposed mode of action (MOA) for diuron is urothelial cytotoxicity and necrosis followed by regenerative urothelial hyperplasia. Diuron-induced urothelial cytotoxicity is not due to urinary solids. Diuron is extensively metabolized, and in rats, N-(3,4-dichlorophenyl)urea (DCPU) and 4,5-dichloro-2-hydroxyphenyl urea (2-OH-DCPU) were the predominant urinary metabolites; lesser metabolites included N-(3,4-dichlorophenyl)-3-methylurea (DCPMU) and trace levels of 3,4-dichloroaniline (DCA). In humans, DCPMU and DCPU have been found in the urine after a case of product abuse. To aid in elucidating the MOA of diuronand to evaluate the metabolites that are responsible for the diuron toxicity in the bladder epithelium, we investigated the urinary concentrations of metabolites in male Wistar rats treated with 2500 ppm of diuron, the urothelial cytotoxicity in vitro of the metabolites and their gene expression profiles. DCPU was found in rat urine at concentrations substantially greater than the in vitro IC50 and induced more gene expression alterations than the other metabolites tested. 2-OH-DCPU was present in urine at a concentration approximately half of the in vitro IC50, whereas DCPMU and DCA were present in urine at concentrations well below the IC50. For the diuron-induced MOA for the rat bladder, we suggest that DCPU is the primary metabolite responsible for the urothelial cytotoxicity with some contribution also by 2-OH-DCPU. This study supports a MOA for diuron-induced bladder effects in rats consisting of metabolism to DCPU (and 2-OH-DCPU to a lesser extent), concentration and excretion in urine, urothelial cytotoxicity, and regenerative proliferation.

PMID:24172598 Da Rocha MS et al; Toxicology 314 (2-3): 238-46 (2013)


This study was designed to investigate diuron biotransformation and disposition ... . The only metabolic pathway detected by liquid chromatography/mass spectometry in human liver homogenates and seven types of mammalian liver microsomes including human was demethylation at the terminal nitrogen atom. No other phase I or phase II metabolites were observed. The rank order of N-demethyldiuron formation in liver microsomes based on intrinsic clearance (V(max)/K(m)) was dog > monkey > rabbit > mouse > human > minipig > rat. All tested recombinant human cytochrome P450s (P450s) catalyzed diuron N-demethylation and the highest activities were possessed by CYP1A1, CYP1A2, CYP2C19, and CYP2D6. Relative contributions of human CYP1A2, CYP2C19, and CYP3A4 to hepatic diuron N-demethylation, based on average abundances of P450 enzymes in human liver microsomes, were approximately 60, 14, and 13%, respectively. Diuron inhibited relatively potently only CYP1A1/2 (IC(50) 4 uM)...

PMID:17576805 Abass K et al; Drug Metab Dispos 35 (9): 1634-41 (2007)


3,4-dichloroaniline (3,4-DCA) is a metabolite of diuron as well as two other pesticides, linuron and propanil. However, EPA's Metabolism Assessment Review Committee (MARC) concluded that residues of 3,4-DCA should not be aggregated for the diuron, linuron, and propanil risk assessments because 3,4-DCA is significant residue of concern for propanil, but is not a residue of concern per se for diuron or linuron. Although the analytical method for quantifying residues of concern from diuron converts all residues to 3,4-DCA as a convenience, 3,4-DCA was not a significant residue in any metabolism or hydrolysis study.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document for Diuron p.15 List A Case 0046 (September 2003). Available from, as of July 11, 2018: https://www.epa.gov/pesticides/reregistration/status.htm


... In ... a woman poisoned with Diuron, 1-(3,4-dichlorophenyl)-3,3-dimethylurea, plus 3-amino-1,2,4-triazole, 1-(3,4-dichlorophenyl)-3-methylurea, and 1-(3,4-dichlorophenyl)urea were isolated from urine. The urine probably contained small amt of 3,4-dichloroaniline, but no unchanged herbicide.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 312


For more Metabolism/Metabolites (Complete) data for Diuron (12 total), please visit the HSDB record page.


Diuron has known human metabolites that include N-demethyldiuron.

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


4.4 Mechanism of Action

/Chlorophyll/ fluorescence measurements indicated significant electron transport inhibition in /intact soybean/ leaves 1 hr after treatment with 40 mM solutions of ... diuron.

Richard EP Jr et al; Weed Sci 31 (3): 361-7 (1983)


The potent inhibitory effect of substituted ureas on the photosynthetic mechanism of ... plants ... /is exerted through inhibition of/ Hill reaction, ie, evolution of oxygen in presence of living chloroplasts & suitable hydrogen acceptor. /Substituted ureas/

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. 262


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