Substituted phenyluracils

Details Substituted phenyluracils Substituted phenyluracils

2002-02-20

2003-11-18

Ford, John M. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C544S311000, C544S312000, C544S313000, C544S314000, C544S295000, C544S296000, C544S062000, C544S180000

Reexamination Certificate

active

06649760

ABSTRACT:

The invention relates to novel substituted phenyluracils, to processes for their preparation and to their use as crop treatment agents, in particular as herbicides.
It is known that certain substituted phenyluracils have herbicidal properties (cf. EP 408382/U.S. Pat. No. 5,084,084/U.S. Pat. No. 5,127,935/U.S. Pat. No. 5,154,755, EP 563384, EP 648749, U.S. Pat. No. 4,979,982, U.S. Pat. No. 5,169,430, WO 91/00278, WO-A-97/01541, WO-A-00/02866, WO-A-98141093). However, these compounds have hitherto not attained significant importance.
This invention, accordingly, provides the novel substituted phenyluracils of the general formula (I)
in which
Q represents O (oxygen), S (sulphur), SO or SO
2
,
R
1
represents hydrogen, amino, optionally cyano-, halogen- or C
1
-C
4
-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,
R
2
represents cyano, carboxyl, carbamoyl, thiocarbamoyl or in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms,
R
3
represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 4 carbon atoms,
R
4
represents hydrogen, nitro, cyano or halogen,
R
5
represents cyano, thiocarbamoyl, bromine or in each case optionally halogen-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms, and
R
6
represents an optionally nitro-, hydroxyl-, mercapto-, amino-, cyano-, carboxyl-, carbamoyl-, halogen-, C
1
-C
4
-alkyl-, cyano-C
1
-C
4
-alkyl-, carboxyl -C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkyl-, C
1
-C
4
-alkylaminocarbonylalkyl-, di-(C
1
-C
4
-alkyl)-aminocarbonylalkyl-, C
1
-C
4
-alkoxy-, cyano-C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkoxy-, C
1
-C
4
-alkoxy-C
1
-C
4
-alkoxy-, carboxyl-C
1
-C
4
-alkoxy-, C
1
-C
4
-alkoxy-carbonyl-C
1
-C
4
-alkoxy-, C
1
-C
4
-alkylaminocarbonyl-C
1
-C
4
-alkoxy-, di-(C
1
-C
4
-alkyl)-aminocarbonyl-C
1
-C
4
-alkoxy-, C
1
-C
4
-alkoxy-carbonyl-, C
2
-C
4
-alkenyloxy-, C
2
-C
4
-alkinyloxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-halogenoalkyl-thio-, C
1
-C
4
-alkylsulphinyl-, C
1
-C
4
-halogenoalkylsulphinyl-, C
1
-C
4
-alkyl-sulphonyl-, C
1
-C
4
-halogenoalkylsulphonyl-, C
1
-C
4
-alkyl-carbonyl-amino-, C
1
-C
4
-alkoxy-carbonyl-amino- or C
1
-C
4
-alkyl-sulphonyl-amino-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,
including all possible tautomeric forms of the compounds of the general formula (I) and the possible salts and acid or base adducts of the compounds of the general formula (I).
In the definitions, the hydrocarbon chains, such as alkyl or alkanediyl, are in each case straight-chain or branched—including in combination with heteroatoms, such as in alkoxy.
Preferred substituents or preferred ranges of the radicals that are present in the formulae given above and below are defined below.
Q preferably represents O (oxygen), S (sulphur) or SO
2
.
R
1
preferably 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.
R
2
preferably represents cyano, carboxyl, carbamoyl, thiocarbamoyl or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or 1-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl.
R
3
preferably represents hydrogen, fluorine, chlorine, bromine or in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl.
R
4
preferably represents hydrogen, cyano, fluorine, chlorine or bromine.
R
5
preferably represents cyano, thiocarbamoyl, bromine or in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxy or ethoxy.
R
6
preferably 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-i-propyl-, fluoro-i-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.
Q particularly preferably represents O (oxygen) or S (sulphur).
R
1
particularly preferably represents hydrogen, amino or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl or ethyl.
R
2
particularly preferably represents cyano, carboxyl, carbamoyl or in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxycarbonyl or ethoxycarbonyl.
R
3
particularly preferably represents hydrogen, fluorine, chlorine, bromine or in each case optionally fluorine- and/or chlorine-substituted methyl or ethyl.
R
4
particularly preferably represents hydrogen, fluorine or chlorine.
R
5
particularly preferably represents cyano, thiocarbamoyl, bromine or trifluoromethyl.
R
6
particularly preferably 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-, et

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