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Isoproturon

Isoproturon

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Also known as: 34123-59-6, 3-(4-isopropylphenyl)-1,1-dimethylurea, Graminon, Tolkan, Arelon, Belgran

Molecular Formula

C₁₂H₁₈N₂O

Molecular Weight

206.28 g/mol

InChI Key

PUIYMUZLKQOUOZ-UHFFFAOYSA-N

FDA UNII

66066K098P

1 2D Structure

Isoproturon

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,1-dimethyl-3-(4-propan-2-ylphenyl)urea

2.1.2 InChI

InChI=1S/C12H18N2O/c1-9(2)10-5-7-11(8-6-10)13-12(15)14(3)4/h5-9H,1-4H3,(H,13,15)

2.1.3 InChI Key

PUIYMUZLKQOUOZ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)C1=CC=C(C=C1)NC(=O)N(C)C

2.2 Other Identifiers

2.2.1 UNII

66066K098P

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Isoproturon-50

2. N'-(4-(1-methylethyl)phenyl)-n,n-dimethylurea

2.3.2 Depositor-Supplied Synonyms

1. 34123-59-6

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

3. Graminon

4. Tolkan

5. Arelon

6. Belgran

7. Arelon R

8. Nocilon

9. Ipu Stefes

10. Ip-flo

11. Alon

12. Hytane 500l

13. Dpx 6774

14. 3-p-cumenyl-1,1-dimethylurea

15. Hoe 16410

16. 1,1-dimethyl-3-(4-propan-2-ylphenyl)urea

17. N-4-isopropylphenyl-n,n-dimethylurea

18. Iprofile

19. Cl 12150

20. Ip 50

21. Urea, 3-p-cumenyl-1,1-dimethyl-

22. Cga-18731

23. N,n-dimethyl-n'-(4-(1-methylethyl)phenyl)urea

24. Urea, 1,1-dimethyl-3-(p-isopropylphenyl)-

25. 3,3-dimethyl-1-[4-(propan-2-yl)phenyl]urea

26. Urea, N,n-dimethyl-n'-[4-(1-methylethyl)phenyl]-

27. Chebi:6049

28. N-(4-isopropylphenyl)-n',n'-dimethylharnstoff

29. Isoproturon 10 Microg/ml In Acetonitrile

30. Isoproturon 100 Microg/ml In Acetonitrile

31. 66066k098p

32. 1,1-dimethyl-3-[4-(propan-2-yl)phenyl]urea

33. Zodiac Tx

34. N,n-dimethyl-n'-[4-(1-methylethyl)phenyl]urea

35. Protugan

36. Isoproturon [bsi:iso]

37. Isoproturon [iso]

38. 1007461-76-8

39. Urea, N,n-dimethyl-n'-(4-(1-methylethyl)phenyl)-

40. Einecs 251-835-4

41. Brn 2214033

42. Tolken

43. Unii-66066k098p

44. N-(isopropyl-4-phenyl)-n',n'-dimethyluree [french]

45. N-(4-isopropylphenyl)-n',n'-dimethylharnstoff [german]

46. Isoproturon [mi]

47. 35689 R.p.

48. N-(isopropyl-4-phenyl)-n',n'-dimethyluree

49. Dsstox_cid_22077

50. Dsstox_rid_79917

51. Dsstox_gsid_42077

52. Schembl62200

53. Ip50

54. Isoproturon, Analytical Standard

55. Chembl2251591

56. Dtxsid1042077

57. Hsdb 6689

58. Zinc392884

59. Hy-b1859

60. Tox21_301329

61. Mfcd00078684

62. 4-isopropylphenyl-n',n'-dimethylurea

63. Akos002959799

64. Gs-3581

65. Isoproturon 100 Microg/ml In Methanol

66. Isoproturon 1000 Microg/ml In Methanol

67. Ncgc00255738-01

68. 1,1-dimethyl-3-(p-isopropylphenyl)-urea

69. N'-(4-isopropylphenyl)-n,n-dimethylurea

70. 3-(4-isopropylphenyl)-1,1-dimethyl-urea

71. Cas-34123-59-6

72. Db-048570

73. Isoproturon 1000 Microg/ml In Acetonitrile

74. N-(4-isopropylphenyl)-n',n'-dimethylurea

75. Cs-0013926

76. Ft-0613679

77. Ft-0670547

78. I0843

79. H10431

80. Isoproturon, Pestanal(r), Analytical Standard

81. A822082

82. J-019459

83. Q2184565

84. 3-(4-isopropylphenyl)-1,1-dimethyl-urea;isoproturon

85. Isoproturon Solution, 100 Ng/mul In Acetonitrile, Pestanal(r), Analytical Standard

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₈N₂O
Molecular Weight	206.28 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	2
Exact Mass	206.141913202 g/mol
Monoisotopic Mass	206.141913202 g/mol
Topological Polar Surface Area	32.3 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	206
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.)

4.2 Absorption, Distribution and Excretion

Toxicokinetic behavior and recoveries of isoproturon from feces, urine, and different tissues of goat were determined after 4, 5, 6, and 7 days following single oral administration at 500 mg/kg. Isoproturon was rapidly absorbed and attained blood concentration within 15 min of administration. The kinetic behavior followed a two-compartment open model. The higher half-life (beta) (9.78 +/- 0.33 hr) and V(d)()area (4.49 +/- 0.41 L/kg) associated with lower Cl(B) (0.32 +/- 0.02 L/kg/hr) suggested slow elimination from the blood. Approximately 56% of the total administered compound was recovered from feces. The rate of excretion of isoproturon through feces was maximum at 48 hr and could not be detected beyond 120 hr. The excretion pattern of isoproturon through urine resembled that of feces, and approximately 10-11% was eliminated in urine. A maximum quantity of residue was detected in all tissues of goats slaughtered after 4 days followed by a substantial decline after day 5, and nothing could be detected after day 7. Histopathological study revealed that isoproturon produced moderate cellular changes like fatty degeneration in the liver and kidney and emphysema in the lung after 7 days post administration.

PMID:10554216 Juliet S et al; J Agric Food Chem 46 (1): 178-183 (1998)

4.3 Metabolism/Metabolites

Using ring-(14)C-labeled isoproturon (1 ug/L), the uptake into spawn and tadpoles of Bombina bombina and Bombina variegata was investigated. Two percent of the applied radioactivity was found per gram fresh weight in the embryo after 24 hr. Results indicate that the jelly mass of the spawn does not act as a sufficient physical barrier for protection against the uptake and influence of isoproturon (IPU) on the embryo. In vivo metabolism of ring-(14)C-labeled IPU by the cytochrome P-450 system was analyzed in tadpoles. Different metabolites of IPU, such as N-demethylated and C-hydroxylated derivatives, and the olefinic metabolite were detected. In tadpoles of B. variegata, the activity of microsomal and soluble glutathione-S-transferase (sGSTs) toward different model substrates was measured after treatment with IPU. Activities of sGST increased corresponding to elevated stress by IPU dependent on exposure time and dose. Compared to the pure active ingredient IPU, the commercial phenyl-urea herbicide Tolkan Flo, consisting of IPU and an emulsifier, also caused significantly elevated enzymatic response.

PMID:12297088 Greulich K et al; Ecotoxicol Environ Saf 52 (3): 256-66 (2002)

4.4 Biological Half-Life

Toxicokinetic behavior and recoveries of isoproturon from feces, urine, and different tissues of goat were determined after 4, 5, 6, and 7 days following single oral administration at 500 mg/kg. ... The higher half-life (beta) (9.78 +/- 0.33 hr) and V(d)()area (4.49 +/- 0.41 L/kg) associated with lower Cl(B) (0.32 +/- 0.02 L/kg/hr) suggested slow elimination from the blood. ...

PMID:10554216 Juliet S et al; J Agric Food Chem 46 (1): 178-183 (1998)

4.5 Mechanism of Action

Inhibition of photosynthesis at photosystem II.

Crop Protection Handbook Volume 100, Meister Media Worldwide, Willoughby, OH 2014, p. 370