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    Linuron

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    2D Structure
    Also known as: 330-55-2, 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea, Methoxydiuron, Afalon, Cephalon, Aphalon
    Molecular Formula
    C9H10Cl2N2O2
    Molecular Weight
    249.09  g/mol
    InChI Key
    XKJMBINCVNINCA-UHFFFAOYSA-N
    FDA UNII
    01XP1SU59O
    A selective pre- and post-emergence herbicide. (From Merck Index, 11th ed)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea
    2.1.2 InChI
    InChI=1S/C9H10Cl2N2O2/c1-13(15-2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14)
    2.1.3 InChI Key
    XKJMBINCVNINCA-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN(C(=O)NC1=CC(=C(C=C1)Cl)Cl)OC
    2.2 Other Identifiers
    2.2.1 UNII
    01XP1SU59O
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Afalon

    2.3.2 Depositor-Supplied Synonyms

    1. 330-55-2

    2. 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea

    3. Methoxydiuron

    4. Afalon

    5. Cephalon

    6. Aphalon

    7. Linurex

    8. Garnitan

    9. Lorox

    10. Herbicide 326

    11. Afalon Inuron

    12. Linorox

    13. Rotalin

    14. Sarclex

    15. Sinuron

    16. Du Pont 326

    17. Linex 4l

    18. Laroks

    19. N'-(3,4-dichlorophenyl)-n-methoxy-n-methylurea

    20. Dupont Herbicide 326

    21. Urea, N'-(3,4-dichlorophenyl)-n-methoxy-n-methyl-

    22. Lorox Linuron Weed Killer

    23. 1-methoxy-1-methyl-3-(3,4-dichlorophenyl)urea

    24. Hoe 2810

    25. Urea, 3-(3,4-dichlorophenyl)-1-methoxy-1-methyl-

    26. 3-(3,4-dichlorophenyl)-1-methoxy-1-methyl-urea

    27. N-(3,4-dichlorophenyl)-n'-methyl-n'-methoxyurea

    28. 01xp1su59o

    29. Chebi:6482

    30. Linex

    31. 1-(3,4-dichlorophenyl)3-methoxy-3-methyluree

    32. 3-(3,4-dichloor-fenyl)-1-methoxy-1-methylureum

    33. 3-(3,4-dichloro-fenil)-1-metossi-1-metil-urea

    34. 3-(4,5-dichlorphenyl)-1-methoxy-1-methylharnstoff

    35. N-(3,4-dwuchlorofenylo)n'-metoksy-n'-metylomocznik

    36. Linuron 10 Microg/ml In Acetonitrile

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

    38. Linuron 100 Microg/ml In Acetonitrile

    39. Malurane

    40. Profalon

    41. Soilcid

    42. Certroli-lin

    43. Dsstox_cid_4163

    44. Laroks [polish]

    45. Du Pont Herbicide 326

    46. Dsstox_rid_77311

    47. Lorox Weed Killer

    48. Dsstox_gsid_24163

    49. Linuron (herbicide)

    50. Caswell No. 528

    51. Alfalon

    52. Linuron Solution

    53. Linuron [ansi:bsi:iso]

    54. Cas-330-55-2

    55. Linuron [iso]

    56. Hsdb 1733

    57. Hoe 002810

    58. Hoe 02 810

    59. Einecs 206-356-5

    60. Epa Pesticide Chemical Code 035506

    61. Brn 2128725

    62. Unii-01xp1su59o

    63. Norunil

    64. Scarclex

    65. Atlas Linuron

    66. 1-(3,4-dichlorophenyl)3-methoxy-3-methyluree [french]

    67. 3-(3,4-dichloor-fenyl)-1-methoxy-1-methylureum [dutch]

    68. 3-(3,4-dicloro-fenil)-1-metossi-1-metil-urea [italian]

    69. 3-(3,4-dichloro-fenil)-1-metossi-1-metil-urea [italian]

    70. 3-(4,5-dichlorphenyl)-1-methoxy-1-methylharnstoff [german]

    71. 3-(3,4-dichlor-phenyl)-1-methoxy-1-methyl-harnstoff [german]

    72. Linuron [hsdb]

    73. N-(3,4-dwuchlorofenylo)n'-metoksy-n'-metylomocznik [polish]

    74. Linuron [mi]

    75. 3-(3,4-dicloro-fenil)-1-metossi-1-metil-urea

    76. Schembl56566

    77. N-(3,4-dichlorophenyl)-n'-methoxy-n'-methylurea

    78. Bidd:er0455

    79. Chembl448213

    80. Dtxsid2024163

    81. Xkjmbincvninca-uhfffaoysa-

    82. Zinc900693

    83. Hy-b1866

    84. Linuron 100 Microg/ml In Methanol

    85. Tox21_201281

    86. Tox21_300732

    87. Linuron 100 Microg/ml In N-hexane

    88. Stk664290

    89. Akos015889915

    90. Ncgc00160429-01

    91. Ncgc00160429-02

    92. Ncgc00160429-03

    93. Ncgc00160429-04

    94. Ncgc00160429-05

    95. Ncgc00160429-06

    96. Ncgc00254638-01

    97. Ncgc00258833-01

    98. Db-048328

    99. Linuron, Pestanal(r), Analytical Standard

    100. Cs-0013933

    101. Ft-0603379

    102. L0395

    103. 330l552

    104. A821586

    105. N'-(3,4-dichlorophenyl)-n-methoxy-n-methyl Urea

    106. Q421476

    107. J-018993

    108. Linuron Solution, 100 Mug/ml In Methanol, Pestanal(r), Analytical Standard

    2.4 Create Date
    2005-03-27
    3 Chemical and Physical Properties
    Molecular Weight 249.09 g/mol
    Molecular Formula C9H10Cl2N2O2
    XLogP33.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count2
    Exact Mass248.0119330 g/mol
    Monoisotopic Mass248.0119330 g/mol
    Topological Polar Surface Area41.6 Ų
    Heavy Atom Count15
    Formal Charge0
    Complexity228
    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

    IN CHRONIC TOXICITY STUDIES ... LINURON ... CONTINUOUSLY FED TO RATS & DOGS FOR ... TWO YR AT DIETARY LEVELS ... FROM 25 TO 2500 PPM ... TOTAL ANILINE-CONTAINING RESIDUES IN BLOOD & ... (MUSCLE, FAT, LIVER, KIDNEY, SPLEEN) WERE A FEW TO 100 PPM. ... RESIDUES REPRESENTED ONLY MINUTE FRACTION OF ... HERBICIDE INGESTED BY ANIMALS.

    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. 237

    LINURON IS MOST READILY ABSORBED THROUGH THE ROOT SYSTEM; LESS SO THROUGH FOLIAGE & STEMS. HOWEVER, FOLIAR ABSORPTION ... IS SIGNIFICANTLY GREATER THAN THAT OF DIURON, MONURON, OR FENURON. ... TRANSLOCATION IS PRIMARILY UPWARD IN THE XYLEM.

    Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 287

    ... RESIDUE DATA ... OBTAINED IN SHORT TERM ELIMINATION EXPERIMENTS ... . AMT OFRADIOACTIVITY WHICH PERSISTED IN BLOOD & DIFFERENT TISSUES AT END OF 72 HR ... PERIODS WERE NO MORE & USUALLY MUCH LESS THAN 1% OF DOSE APPLIED.

    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. 237

    4.3 Metabolism/Metabolites

    ... LINURON-INDUCIBLE ENZYME WAS OBTAINED FROM BACILLUS SPHAERICUS. THIS ACYLAMIDASE DEGRADED LINURON BY HYDROLYSIS OF AMIDE BOND WITH ... RELEASE OF CARBON DIOXIDE & N,O-DIMETHYL HYDROXYLAMINE. ... ENZYME WAS SPECIFIC FOR METHOXY-SUBSTITUTED PHENYLUREAS & DID NOT HYDROLYZE 1,1-DIMETHYL PHENYLUREAS ... .

    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. 382

    IN GREENHOUSE STUDIES, LINURON ENTERED CORN (ZEA MAYS L), SOYBEAN (GLYCINE MAX L) & CRABGRASS (DIGITARIA SANGUINALIS L) WITH ABSORBED WATER. DEMETHYL LINURON & 3,4-DICHLORO-ANILINE WERE FOUND IN TISSUES. ... SOME LINURON BOUND WITHIN PLANT ... .

    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. 382

    LINURON ... FED TO ALBINO RATS. URINE ... ANALYZED FOR METABOLITES /&/ N-(3,4-DICHLOROPHENYL)UREA, N-(3,4-DICHLOROPHENYL)-N'-METHYLUREA & 3,4-DICHLOROANILINE WERE FOUND FREE. N-(2-HYDROXY-4,5-DICHLOROPHENYL)-N'-METHYLUREA, N-(5-HYDROXY-3,4-DICHLOROPHENYL)UREA & 6-ACETAMIDO-2,3-DICHLOROPHENOL ... /WERE IDENTIFIED/ AS GLUCURONIDES OR SULFATES.

    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. 340

    In rats linuron is metabolized by demethoxylation followed by hydroxylation of the benzene ring. Major urinary metabolites are urea derivatives; no unchanged linuron could be demonstrated. Only trace amounts of 3,4-dichloroaniline were found. If metabolism to dichloroaniline is major pathway in humans, ... methemoglobinemia should be anticipated after toxic doses.

    Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-331

    For more Metabolism/Metabolites (Complete) data for LINURON (9 total), please visit the HSDB record page.

    4.4 Mechanism of Action

    Inhibits photosynthesis.

    Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A248/Aug 87