Substituted herbicidal phenyluracils

Details Substituted herbicidal phenyluracils Substituted herbicidal phenyluracils

2001-12-13

2003-09-23

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S311000, C544S312000, C544S313000, C544S314000

Reexamination Certificate

active

06624120

ABSTRACT:

The invention relates to novel substituted phenyluracils, to processes and novel intermediates for their preparation and to their use as herbicides.
Certain substituted aryluracils are already known from the (patent) literature (cf. EP-A-255 047, EP-A-260 621, EP-A-408 382, EP-A-438 209, EP-A-473 551, EP-A-517 181, EP-A-563 384, WO-A-91/00278, WO-A-91/07393, WO-A-93/14073, U.S. Pat. No. 4,979,982, U.S. Pat No. 5,084,084, U.S. Pat. No. 5,127,935, U.S. Pat. No. 5,154,755, U.S. Pat. No. 5,169,430, U.S. Pat. No. 5,486,610, U.S. Pat. No. 5,356,863). However, these compounds have hitherto not attained any particular importance.
This invention, accordingly, provides novel substituted phenyluracils of the general formula (I)
in which
m represents 0, 1, 2 or 3,
n represents 0, 1, 2, 3 or 4,
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, carbamoyl, thiocarbamoyl or halogen,
R
5
represents cyano, carbamoyl, thiocarbamoyl, halogen or in each case optionally substituted alkyl or alkoxy,
X represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl, alkinylcarbonyloxy or arylcarbonyloxy, and
Y represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl, alkinylcarbonyloxy or arylcarbonyloxy,
where, in the case that m and/or n are greater than 1, X and Y in the individual compounds possible in each case have identical or different meanings from those given, which is to say that X and Y may be identical or different,
and salts of compounds of the formula (I).
Preferred substituents or ranges of the radicals present in the formulae given above and below are defined below.
m preferably represents 0, 1 or 2.
n preferably represents 0, 1, 2 or 3.
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 represents optionally cyano-, halogen- or C
1
-C
3
-alkoxy-substituted alkyl having 1 to 4 carbon atoms.
R
2
preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, halogen- or C
1
-C
3
-alkoxy-substituted alkyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms.
R
3
preferably represents hydrogen, halogen or represents optionally cyano-, halogen- or C
1
-C
3
-alkoxy-substituted alkyl having 1 to 4 carbon atoms.
R
4
preferably represents hydrogen, cyano, fluorine or chlorine.
R
5
preferably represents cyano, carbamoyl, thiocarbamoyl, halogen or represents in each case optionally halogen-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms.
X preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, 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
-C4-alkoxy-carbonyl-, C
2
-C
4
-alkenyloxy-carbonyl-, C
2
-C
4
-alkinyloxy-carbonyl-, C
1
-C
4
-alkylaminocarbonyl-, di-(C
1
-C
4
-alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6 carbon atoms, represents dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkyl-aminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkyl-sulfonylamino, bis-alkylsulfonyl-amino or N-alkylcarbonyl-N-alkylsulphonyl-amino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C
1
-C
4
-alkoxycarbonyl-, C
1
-C
4
-alkylamino-carbonyl- or di-(C
1
-C
4
-alkyl)-amino-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl or alkinylcarbonyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, or represents benzyloxy.
Y preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, 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
-alkenyloxy-carbonyl-, C
2
-C
4
-alkinyloxy-carbonyl-, aminocarbonyl-, C
1
-C
4
-alkylaminocarbonyl-, di-(C
1
-C
4
-alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl- substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6 carbon atoms, represents dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkyl-aminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkyl-sulfonylamino, bis-alkylsulfonyl-amino or N-alkylcarbonyl-N-alkylsulphonyl-amino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C
1
-C
4
-alkoxycarbonyl-, C
1
-C
4
-alkylamino-carbonyl- or di-(C
1
-C
4
-alkyl)-amino-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl or alkinyl-carbonyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, or represents benzyloxy.
The invention also preferably provides the sodium, potassium, magnesium, calcium, ammonium, C
1
-C
4
-alkyl-ammonium, di-(C
1
-C4-alkyl)-ammonium, tri-(C
1
-C
4
-alkyl)-ammonium, tetra-(C
1
-C
4
-alkyl)-ammonium, tri-(C
1
-C
4
-alkyl)-sulphonium, C
5
- or C
6
-cycloalkyl-ammonium and di-(C
1
-C
2
-alkyl)-benzyl-ammonium salts of compounds of the formula (I), in which m, n, Q, R
1
, R
2
, R
3
, R
4
, R
5
, X and Y have the preferred meanings given above—insofar as the compounds of the formula (I) contain hydrogen atoms attached to O or S.
m particularly preferably represents 0 or 1.
n particularly preferably represents 0, 1 or 2.
Q particularly preferably represents O (oxygen) or S (sulphur).
R
1
particularly preferably represents hydrogen, amino or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl.
R
2
particularly preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxy-carbonyl, n- or i-propoxycarbonyl.
R
3
particularly preferably represents hydrogen, fluorine, chlorine, bromine, or repres

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