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Chemistry

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Also known as: 3060-89-7, Metbromuron, Patoran, 3-(4-bromophenyl)-1-methoxy-1-methylurea, Metobromurone, Monobromuron
Molecular Formula
C9H11BrN2O2
Molecular Weight
259.10  g/mol
InChI Key
WLFDQEVORAMCIM-UHFFFAOYSA-N
FDA UNII
4251089P3L

Metobromuron
1 2D Structure

Metobromuron

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-(4-bromophenyl)-1-methoxy-1-methylurea
2.1.2 InChI
InChI=1S/C9H11BrN2O2/c1-12(14-2)9(13)11-8-5-3-7(10)4-6-8/h3-6H,1-2H3,(H,11,13)
2.1.3 InChI Key
WLFDQEVORAMCIM-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C(=O)NC1=CC=C(C=C1)Br)OC
2.2 Other Identifiers
2.2.1 UNII
4251089P3L
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-(p-bromophenyl)-1-methoxy-1-methylurea

2. Patoran

2.3.2 Depositor-Supplied Synonyms

1. 3060-89-7

2. Metbromuron

3. Patoran

4. 3-(4-bromophenyl)-1-methoxy-1-methylurea

5. Metobromurone

6. Monobromuron

7. Pattonex

8. Urea, N'-(4-bromophenyl)-n-methoxy-n-methyl-

9. N'-(4-bromophenyl)-n-methoxy-n-methylurea

10. Ciba-3126

11. 3-(p-bromophenyl)-1-methoxy-1-methylurea

12. Urea, 3-(p-bromophenyl)-1-methoxy-1-methyl-

13. 3-(p-bromophenyl)-1-methyl-1-methoxyurea

14. 3-(4-bromphenyl)-1-methoxyharnstoff

15. Chebi:81964

16. Metobromuron 10 Microg/ml In Acetonitrile

17. Metobromuron 100 Microg/ml In Acetonitrile

18. 4251089p3l

19. Caswell No. 579a

20. Metobromuron [iso]

21. Ccris 6765

22. Metobromuron [ansi:bsi:iso]

23. Hsdb 1741

24. Einecs 221-301-5

25. Epa Pesticide Chemical Code 035901

26. Brn 2103964

27. Patoran Fl

28. 3-(4-bromphenyl)-1-methoxyharnstoff [german]

29. C-3126

30. Unii-4251089p3l

31. N-(4-bromophenyl)-n'-methyl-n'-methoxy-harnstoff [german]

32. 1-(4-bromophenyl)-3-methoxy-3-methylurea

33. Metobromuron [mi]

34. Metobromuron [hsdb]

35. Dsstox_cid_22157

36. Dsstox_rid_79940

37. Dsstox_gsid_42157

38. Schembl53871

39. N-(4-bromophenyl)-n'-methyl-n'-methoxy-harnstoff

40. Chembl1356637

41. Dtxsid6042157

42. Metobromuron, Analytical Standard

43. Zinc260866

44. Dndi1246791

45. Tox21_301964

46. Akos001609255

47. Ncgc00166156-01

48. Ncgc00255893-01

49. Cas-3060-89-7

50. Db-047812

51. Ft-0603626

52. N-(p-bromophenyl)-n'-methyl-n'-methoxyurea

53. C18793

54. Metobromuron, Pestanal(r), Analytical Standard

55. 060m897

56. J-018035

57. Q18213352

58. Pesticide3_metobromuron_c9h11brn2o2_urea, N'-(4-bromophenyl)-n-methoxy-n-methyl-

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 259.10 g/mol
Molecular Formula C9H11BrN2O2
XLogP32.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass258.00039 g/mol
Monoisotopic Mass258.00039 g/mol
Topological Polar Surface Area41.6 Ų
Heavy Atom Count14
Formal Charge0
Complexity193
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 Absorption, Distribution and Excretion

METOBROMURON IS ABSORBED BY ROOTS AND LEAVES ...

Worthing, C. R. (ed.). Pesticide Manual. 6th ed. Worcestershire, England: British Crop Protection Council, l979., p. 359


... Different urea herbicides exhibit different mobilities in plant systems. ... Uptake and translocation of chloroxuron, fluometuron, and metobromuron by bean plants when supplied to nutrient cultures in equal concn (essentially equimolar) and specific radioactivities were studied. Whereas the movement of chloroxuron to aerial parts was found to be restricted under the short-term conditions applied, both fluometuron and metobromuron were rapidly translocated into leaves. However, the two latter cmpd differed strikingly with regard to their distribution pattern within the leaves. In contrast to metobromuron, which was mainly confined to tracheal veins, fluometuron had almost completely moved out into the mesophyll tissues. Although no extensive comparisons of the movement of different urea structures are available at this time, it would appear that their apoplastic distribution in plants is regulated in part by the same physical-chemical phenomena which control the mobility and availability of the cmpd in soil.

Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 235


4.2 Metabolism/Metabolites

METOBROMURON IS METABOLIZED IN PLANTS & ANIMALS BY N-DEMETHYLATION & N-DEMETHOXYLATION, RESPECTIVELY.

Martin, H. and C.R. Worthing (eds.). Pesticide Manual. 4th ed. Worcestershire, England: British Crop Protection Council, 1974., p. 355


... RING-LABELED (14)C-METOBROMURON WAS SUPPLIED TO POTATOES AND CORN SEEDLINGS. ... FOLLOWING METABOLITES ... /WERE IDENTIFIED/: 3-(4-BROMOPHENYL)-1-METHOXYUREA, 3-(4-BROMOPHENYL)-1-METHYLUREA, AND 4-BROMOPHENYLUREA.

Kearney, P.C., and D.D. Kaufman. Degradation of Herbicides. New York: Marcel Dekker, Inc., 1969., p. 99


METOBROMURON YIELDS 3-(P-BROMOPHENYL)-1-METHYLUREA AND 3-(P-BROMOPHENYL)-1-METHOXYUREA IN TALAROMYCES. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. M45


(14)C-Metobromuron was incubated with human embryonic lung (HEL) cells. More than 95% of the label was recovered as unchanged metobromuron. Of four metabolites, three were identified: 3-(4-bromophenyl)-1-methylurea; 4-bromophenylurea; and 3-(4-bromophenyl)-1-methylurea.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 563


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