Substituted phenyluracils
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Abstract
Phenyluracils of the general formula (I)
in which
Q, R1, R2, R3, R4, R5 and R6 each have one of the meanings given in the description,
and processes for their preparation and their use as herbicides.
16 Citations
18 Claims
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1. Substituted phenyluracils of the general formula (I)
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18)
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2. Compounds according to claim 1, characterized in that
Q represents O (oxygen), S (sulphur) or SO2, R1 represents hydrogen, amino, in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or in each case optionally fluorine- and/or chlorine-substituted propenyl or propinyl, R2 represents cyano, carboxyl, carbamoyl, thiocarbamoyl or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, R3 represents hydrogen, fluorine, chlorine, bromine or in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, R4 represents hydrogen, cyano, fluorine, chlorine or bromine, R5 represents cyano, thiocarbamoyl, bromine or in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxy or ethoxy, and R6 represents an in each case optionally nitro-, hydroxyl-, amino-, cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, chloromethyl-, fluoromethyl-, dichloromethyl-, difluoromethyl-, trichloromethyl-, trifluoromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-, chloroethyl-, fluoroethyl-, dichloroethyl-, difluoroethyl, chlorofluoroethyl-, trichloroethyl-, trifluoroethyl-, chlorodifluoroethyl-, fluorodichloroethyl-, tetrafluoroethyl-, chlorotrifluoroethyl-, pentafluoroethyl-, chloro-n-propyl-, fluoro-n-propyl-, chloro-1-propyl-, fluoro-1-propyl-, dichloropropyl-, difluoropropyl-, trichloropropyl-, trifluoropropyl-, cyanomethyl-, cyanoethyl-, cyanopropyl-, carboxymethyl-, carboxyethyl-, carboxypropyl-, methoxymethyl-, ethoxymethyl-, propoxymethyl-, methoxyethyl-, ethoxyethyl-, methoxycarbonylmethyl-, ethoxycarbonylmethyl-, n- or i-propoxycarbonylmethyl-, methylaminocarbonylmethyl-, ethylaminocarbonylmethyl-, dimethylaminocarbonylmethyl-, methoxycarbonylethyl-, ethoxycarbonylethyl-, n- or i-propoxycarbonylethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, carboxymethoxy-, carboxyethoxy-, methoxycarbonylmethoxy-, ethoxycarbonylmethoxy-, n- or i-propoxycarbonylmethoxy-, methylaminocarbonylmethoxy-, ethylaminocarbonylmethoxy-, dimethylaminocarbonylmethoxy-, methoxycarbonylethoxy-, ethoxycarbonylethoxy-, n- or i-propoxycarbonylethoxy-, methylaminocarbonylethoxy-, ethylaminocarbonylethoxy-, dimethylaminocarbonylethoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, propenyloxy-, butenyloxy-, propinyloxy-, butinyloxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, difluoromethylthio-, trifluoromethylthio-, chlorodifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulfonyl-, trifluoromethylsulphonyl-, acetylamino-, propionylamino-, n- or i-butyroylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, n- or i-propoxycarbonylamino-, methylsulphonylamino-, ethylsulphonylamino-, n- or i-propylsulphonylamino-substituted nitrogen-containing heterocyclic grouping form the group consisting of pyrrolyl, pyrazolyl, imidazolyl, triazolyl, triazolinyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, quinolinyl, quinazolinyl, quinoxalinyl. -
3. Compounds according to claim 1 or 2, characterized in that
Q represents O (oxygen) or S (sulphur), R1 represents hydrogen, amino or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl or ethyl, R2 represents cyano, carboxyl, carbamoyl or in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxycarbonyl or ethoxycarbonyl, R3 represents hydrogen, fluorine, chlorine, bromine or in each case optionally fluorine- and/or chlorine-substituted methyl or ethyl, R4 represents hydrogen, fluorine or chlorine, R5 represents cyano, thiocarbamoyl, bromine or trifluoromethyl, and R6 represents an in each case optionally nitro-, hydroxyl-, amino-, cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, dichloromethyl-, difluoromethyl-, trichloromethyl-, trifluoromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, carboxymethoxy-, carboxyethoxy-, methoxycarbonylmethoxy-, ethoxycarbonylmethoxy-, n- or i-propoxycarbonylmethoxy-, methoxycarbonylethoxy-, ethoxycarbonylethoxy-, n- or i-propoxycarbonylethoxy-, methoxycarbonyl-, ethoxycarbonyl-, propenyloxy-, butenyloxy-, propinyloxy-, butinyloxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, difluoromethylthio-, trifluoromethylthio-, chlorodifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl, ethylsulphonyl-, n- or i-propylsulphonyl-, trifluoromethylsulphonyl-, acetylamino-, propionylamino-, n- or i-butyroylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, n- or i-propoxycarbonylamino-, methylsulphonylamino-, ethylsulphonylamino-, n- or i-propylsulphonylamino-substituted nitrogen-containing heterocyclic grouping from the group consisting of pyrrolyl, pyrazolyl, imidazolyl, triazolyl; - triazolinyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, quinolinyl, quinazolinyl, quinoxalinyl.
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4. Compounds according to any of claims 1 to 3, characterized in that
R1 represents hydrogen, amino, methyl or ethyl, R2 represents cyano or trifluoromethyl, R3 represents hydrogen, chlorine or methyl, R5 represents cyano, thiocarbamoyl or bromine, and R6 represents in each case optionally hydroxyl-, amino-, cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, dichloromethyl-, difluoromethyl-, trichloromethyl-, trifluoromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, carboxymethoxy-, carboxyethoxy-, methoxycarbonylmethoxy-, ethoxycarbonylmethoxy-, n- or i-propoxycarbonylmethoxy-, methoxycarbonylethoxy-, ethoxycarbonylethoxy-, n- or i-propoxycarbonylethoxy-, methoxycarbonyl-, ethoxycarbonyl-, propenyloxy-, butenyloxy-, propinyloxy-, butinyloxy-, methylthio-, ethylthio-, n- or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, chlorodifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulfonyl-, trifluoromethylsulphonyl-, acetylamino-, propionylamino-, n- or i-butyroylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, n- or i-propoxycarbonylamino-, methylsulphonylamino-, ethylsulphonylamino-, n- or i-propylsulphonylamino-substituted pyrazolyl, pyridinyl, pyrimidinyl, triazinyl or benzoxazolyl. -
5. Compounds according to any of claims 1 to 4, characterized in that
R1 represents hydrogen, amino or methyl, R2 represents trifluoromethyl, R5 represents cyano or bromine, and R6 represents in each case optionally hydroxyl-, amino-, cyano-, fluorine-, chlorine-, methyl-, ethyl-, trichloromethyl-, methoxy- or ethoxy-substituted pyrazolyl, pyridinyl, pyrimidinyl or benzoxazolyl. -
6. Compounds according to any of claims 1 to 5, characaterized in that
Q represents O (oxygen). -
7. Process for preparing compounds according to any of claims 1 to 6, characterized in that
(a) phenyluracils of the general formula (II) - in which
Q, R1, R2, R3, R4 and R5 are each as defined in any of claims 1 to 6 are reacted with compounds of the general formula (III) X1—
R6
(III)
in whichR6 is as defined in any of claims 1 to 5 and X1 represents halogen or alkylsulphonyl, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or that (b) halogenophenyluracils of the general formula (IV)
in whichR1, R2, R3, R4 and R5 are each as defined in any of claims 1 to 5 and X2 represents halogen are reacted with compounds of the general formula (V) M-Q-R6
(V)in which Q and R6 are each as defined in any of claims 1 to 6 and M represents hydrogen or a metal equivalent, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or that (c) aminoalkenoic acid esters of the general formula (VI)
in whichR1, R2 and R3 are each as defined in any of claims 1 to 5 and R represents alkyl, aryl or arylalkyl, are reacted with substituted phenyl isocyanates of the general formula (VII)
in whichQ, R4, R5 and R6 are each as defined in any of claims 1 to 6 or with substituted phenylurethanes (phenylcarbamates) of the general formula (VIII)
in whichQ, R4, R5 and R6 are each as defined in any of claims 1 to 6 and R represents alkyl, aryl or arylalkyl, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or that (d) substituted N-phenyl-1-alkoxycarbonylamino-maleimides of the general formula (IX)
in whichQ, R4, R5 and R6 are each as defined in any of claims 1 to 6 and R′
represents alkylare reacted with a metal hydroxide in the presence of water and, if appropriate in the presence of an organic solvent, or that (e) substituted phenyluracils of the general formula (Ia)
in whichQ, R2, R3, R4, R5 and R6 are each as defined in any of claims 1 to 6 are reacted with 1-aminooxy-2,4-dinitro-benzene or 2-aminooxysulphonyl-1,3,5-trimethylbenzene or with alkylating agents of the general formula (X) X3-A1
(X)
in whichA1 represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 4 carbon atoms or in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 4 carbon atoms, and X3 represents halogen or the grouping —
O—
SO2—
O-A1,if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and electrophilic or nucleophilic and/or oxidation or reduction reactions within the scope of the definition of the substituents are, if appropriate, subsequently carried out in a customary manner.
- in which
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8. Compounds of the formula (VII)
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9. Process for preparing compounds according to claim 8, characterized in that aniline derivatives of the general formula (XI)
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10. Compounds of the formula (VIII)
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11. Process for preparing compounds according to claim 10, characterized in that aniline derivatives of the general formula (XI)
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12. Compounds of the formula (XIa)
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13. Process for preparing compounds according to claim 12, characterized in that
(α - ) anilines of the general formula (XIII)
in whichQ, R4 and Y are each as defined in any of claims 1 to 6 and 12 are reacted with compounds of the general formula (III) X1—
R6
(III)
in whichR6 and X1 are each as defined in any of claims 1 to 5 and 7, if appropriate in the presence of an acid acceptor, such as, for example, potassium hydroxide, potassium carbonate or pyridine, and if appropriate in the presence of a diluent, at temperatures between 0°
C. and 200°
C.,or that (β
) anilines of the general formula (XIV)
in whichR4, X2 and Y are each as defined in any of claims 1 to 5, 7 and 12 are reacted with compounds of the general (V) M-Q-R6
(V)
in whichM, Q and R6 are each as defined in any of claims 1 to 7, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, at temperatures between 0°
C. and 200°
C.
- ) anilines of the general formula (XIII)
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14. Compounds of the formula (IX)
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15. Process for preparing compounds according to claim 14, characterized in that alkyl (2,5-di oxo-2,5-dihydro-furan-3-yl)-carbamates of the general formula
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16. Compounds of the formula (Ia)
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17. Herbicidal compositions, characterized in that they comprise at least one compound according to any of claims 1 to 6 and customary extenders.
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18. Use of at least one compound according to any of claims 1 to 6 or a composition according to claim 17 for controlling undesirable plants.
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2. Compounds according to claim 1, characterized in that
Specification
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Current AssigneeDieter Feucht, Hans-Georg Schwarz, Karl-Heinz Linker, Mark Wilhelm Drewes, Peter Dahmen, Roland Andree, Rolf Pontzen
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Original AssigneeDieter Feucht, Hans-Georg Schwarz, Karl-Heinz Linker, Mark Wilhelm Drewes, Peter Dahmen, Roland Andree, Rolf Pontzen
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InventorsDrewes, Mark Wilhelm, Dahmen, Peter, Feucht, Dieter, Schwarz, Hans-Georg, Andree, Roland, Pontzen, Rolf, Linker, Karl-Heinz
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Application NumberUS10/629,450Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current504/243CPC Class CodesC07D 239/34 One oxygen atomC07D 239/54 as doubly bound oxygen atom...C07D 239/557 with carbon atoms having th...C07D 401/12 linked by a chain containin...C07D 403/12 linked by a chain containin...