Substituted phenyl uracils

Details Substituted phenyl uracils Substituted phenyl uracils

2002-06-20

2004-08-24

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S309000, C544S311000, C544S312000, C544S313000, C544S314000

Reexamination Certificate

active

06780821

ABSTRACT:

The invention relates to new substituted phenyluracils, to processes and new intermediates for their preparation, and to their use as herbicides.
Certain substituted aryluracils have already been disclosed in the (patent) literature (cf. EP-A-255047, EP-A-260621, EP-A408382, EP-A-438209, EP-A473551, EP-A-517181, EP-A-563384, WO-A-91/00278, WO-A-91/07393, WO-A-93/14073, WO-A-98/41093, U.S. Pat. Nos. 4,979,982, 5,084,084, 5,127,935, 5,154,755, 5,169,430, 5,486,610, 5,356,863). However, these compounds have not gained any particular importance to date.
There have now been found new substituted phenyluracils of the general formula (I)
in which
n represents the numbers 0, 1, 2, 3, 4 or 5,
Q represents O (oxygen), S (sulphur), SO, SO
2
, NH or N(alkyl),
R
1
represents hydrogen, amino or optionally substituted alkyl,
R
2
represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted alkyl or alkoxycarbonyl,
R
3
represents hydrogen, halogen or optionally substituted alkyl,
R
4
represents hydrogen, cyano, carbarmoyl, thiocarbamoyl or halogen,
R
5
represents cyano, carbamoyl, thiocarbamoyl, halogen or in each case optionally substituted alkyl or alkoxy, and
X represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, phenylcarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkinyl, alkinyloxy or alkinyloxycarbonyl, where, in the event that n is greater than 1, X in the individual compounds which are possible can also have different meanings from those indicated.
In the definitions, the hydrocarbon chains, such as alkyl—also in connection with hetero atoms such as in alkoxy—are in each case straight-chain or branched.
In as far as the compounds of the general formula (I) according to the invention contain substituents with asymmetric carbon atoms, the invention relates in each case to the R enantiomers and the S enantiomers and to any mixtures of these enantiomers, in particular the racemates.
n preferably represents the numbers 0, 1, 2, 3 or 4;
Q preferably represents O (oxygen), S (sulphur), SO, SO
2
, NH or N(C
1
-C
4
-alkyl);
R
1
preferably represents hydrogen, amino, or C
1
-C
4
-alkyl which is optionally substituted by cyano, carboxyl, fluorine, chlorine, C
1
-C4-alkoxy or C
1
-C
4
-alkoxy-carbonyl;
R
2
preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl, or represents C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy-carbonyl, each of which is optionally substituted by cyano, fluorine, chlorine or C
1
-C
4
-alkoxy;
R
3
preferably represents hydrogen, fluorine, chlorine, bromine, or represents C
1
-C
4
-alkyl which is optionally substituted by fluorine or chlorine;
R
4
preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine;
R
5
preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy, each of which is optionally substituted by fluorine and/or chlorine;
X preferably represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or represents alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino, each of which has 1 to 6 carbon atoms and each of which is optionally substituted by hydroxyl, cyano, carboxyl, carbamoyl, fluorine, chlorine, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-alkylsulphonyl, C
1
-C
4
-alkyl- carbonyl, C
1
-C
4
-alkoxy-carbonyl, C
2
-C
4
-alkenyl-oxycarbonyl, C
2
-C
4
-alkinyl-oxycarbonyl, C
1
-C4-alkylamino-carbonyl, di-(C
1
-C
4
-alkyl)amino-carbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl or benzylaminocarbonyl, or represents dialkylamino having 1 to 6 carbon atoms in each of the alkyl groups, or represents alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy or alkylaminocarbonyloxy, each of which has 1 to 6 carbon atoms in the alkyl groups and each of which is optionally substituted by cyano, fluorine, chlorine, bromine or C
1
-C
4
-alkoxy, or represents dialkylaminocarbonyl or dialkylaminocarbonyloxy, each of which has 1 to 6 carbon atoms in the alkyl groups, or represents phenylcarbonyloxy, or represents alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, each of which is optionally substituted by fluorine, chlorine or bromine, or represents alkenyl, alkenyloxy, alkenyloxycarbonyl, alkinyl, alkinyloxy or alkinyloxycarbonyl, each of which has up to 6 carbon atoms and each of which is optionally substituted by cyano, carboxyl, fluorine, chlorine, bromine or C
1
-C
4
-alkoxy-carbonyl;
n especially preferably represents the numbers 1, 2 or 3;
Q especially preferably represents O (oxygen), S (sulphur), SO, SO
2
, NH or N(CH
3
);
R
1
especially preferably represents hydrogen, amino, or represents methyl, ethyl, n- or i-propyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy;
R
2
especially preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl, or represents methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy;
R
3
especially preferably represents hydrogen, fluorine, chlorine, bromine, or represents methyl or ethyl, each of which is optionally substituted by fluorine and/or chlorine;
R
4
especially preferably represents hydrogen, fluorine or chlorine;
R
5
especially preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl or trifluoromethyl;
X especially preferably represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, each of which is optionally substituted by cyano, carboxyl, carbamoyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, allyloxycarbonyl, 1-buten-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, 1-butin-3-yl-oxy-carbonyl, 2-butin-4-yl-oxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino-carbonyl, dimethylaminocarbonyl, diethylamino-carbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl or benzylaminocarbonyl, or represents dimethylamino or diethylamino, or represents acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, or represents dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy or diethylaminocarbonyloxy, or represents phenylcarbonyloxy, or represents acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, n-, i-, s- or t-butylsulphonylamino, each of which is optionally substituted by fluorine or chlorine, or represents ethenyl, propenyl, propenylox

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