Substituted aminouracils

Details Substituted aminouracils Substituted aminouracils

1998-01-21

2002-07-09

Dees, Jose′ G. (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S309000, C544S310000, C544S311000, C544S312000, C544S313000, C544S314000, C544S317000, C544S321000, C544S323000, C544S229000, C544S295000, C544S296000, C544S238000

Reexamination Certificate

active

06417141

ABSTRACT:

The invention relates to novel substituted aminouracils, to processes for their preparation, to their use as herbicides and to novel intermediates.
It is known that certain substituted uracils 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, WO 91/00278, U.S. Pat. No. 497998 [illegible], U.S. Pat. No. 5,169,430). However, these compounds have hitherto not attained any major importance.
This invention, accordingly, provides the novel substituted aminouracils of the general formula (I)
in which
Q represents O, S, SO or SO
2
,
R
1
represents hydrogen, cyano or halogen,
R
2
represents cyano or thiocarbamoyl,
R
3
represents hydrogen or represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
R
4
represents hydrogen, halogen or represents respectively optionally substituted alkyl or alkoxy,
R
5
represents optionally substituted alkyl,
R
6
represents hydrogen or represents respectively optionally substituted alkyl, alkenyl or alkinyl, and
R
7
represents hydrogen or represents respectively optionally substituted alkyl, alkenyl or alkinyl.
The novel substituted aminouracils of the general formula (I) are obtained when
(a) substituted uracils of the general formula (II)
in which
Q, R
1
, R
2
, R
3
, R
4
and R
5
are each as defined above are reacted with an electrophilic aminating agent, if appropriate in the presence of a reaction auxiliary, and if appropriate in the presence of a diluent, or
(b) aminouracils of the general formula (Ia)
in which
Q, R
1
, R
3
, R
4
, R
5
, R
6
and R
7
are each as defined above are reacted with hydrogen sulphide, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or
(c) aminouracils of the general formula (1b)
in which
Q, R
1
, R
2
, R
3
, R
4
and R
5
are each as defined above are reacted with an alkylating agent of the formula (IIIa) and/or of the formula (IIIb)
X—R
7
  (IIIa)
X—R
8
  (IIIb)
in which
R
7
and R
8
are each as defined above and
X represents halogen or the grouping —O—SO
2
—O—R
7
or —O—SO
2
—O—R
8
,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or
(d) aminouracils of the general formula (IV)
in which
R
1
, R
2
, R
4
, R
5
, R
6
and R
7
are each as defined above and
X represents halogen, are reacted with nucleophilic compounds of the general formula (V)
M—Q—R
3
  (V)
in which
Q and R
3
are each as defined above 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.
The novel substituted aminouracils of the general formula (I) have strong herbicidal properties.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case split-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably provides compounds of the formula (I) in which
Q represents O, S, SO or SO
2
,
R
1
represents hydrogen, cyano, fluorine or chlorine,
R
2
represents cyano or thiocarbamoyl,
R
3
represents hydrogen, represents alkyl, alkenyl or alkinyl of in each up to 10 carbon atoms, each of which is optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, or by C
1
-C
4
-alkoxy, C
1
-C
4
-alkyl-carbonyl, C
1
-C
4
-alkoxycarbonyl or N-(C
1
-C
4
-alkyl)-N-phenyl-aminocarbonyl (each of which is optionally substituted by fluorine and/or chlorine)
R
3
furthermore represents cycloalkyl or cycloalkylalkyl of 3 to 8 carbon atoms in the cycloalkyl moiety and optionally up to 4 carbon atoms in the alkyl moiety, each of which is optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkyl-carbonyl or C
1
-C
4
-alkoxy-carbonyl,
R
3
furthermore represents aryl or arylalkyl of 6 or 10 carbon atoms in the aryl moiety and optionally up to 4 carbon atoms in the alkyl moiety, each of which is optionally substituted by cyano, carboxy, nitro, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-alkylsulphonyl, C
1
-C
4
-alkylcarbonyl or C
1
-C
4
-alkoxy-carbonyl (each of which is optionally substituted by fluorine and/or chlorine), by phenyl, phenoxy or phenylthio (each of which is optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and/or trifluoromethoxy), or
R
3
furthermore represents furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxetanyl, thietanyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, triazinyl, indolyl, quinolinyl or quinoxalinyl, each of which is optionally substituted by cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-aklylthio, C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-alkylsulphonyl, C
1
-C
4
-alkyl-carbonyl or C
1
-C
4
-alkoxy-carbonyl (each of which is optionally substituted by fluorine and/or chlorine), by phenyl, phenoxy or phenylthio (each of which is optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and/or trifluoromethoxy),
R
4
represents hydrogen, fluorine, chlorine, bromine or represents respectively optionally fluorine- and/or chlorine-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms,
R
5
represents optionally fluorine- and/or chlorine-substituted alkyl having 1 to 4 carbon atoms,
R
6
represents hydrogen or represents respectively optionally fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted alkyl, alkenyl or alkinyl having in each case up to 6 carbon atoms, and
R
7
represents hydrogen or represents respectively optionally fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted alkyl, alkenyl or alkinyl having in each case up to 6 carbon atoms.
The invention in particular provides compounds of the formula (I) in which
Q represents O, S, SO or SO
2
,
R
1
represents hydrogen, fluorine or chlorine,
R
2
represents cyano or thiocarbamoyl,
R
3
represents hydrogen, represents respectively optionally cyano-, carboxy-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl-, n-, i-, s- or t-pentyl, propenyl, butenyl, pentenyl, propinyl, butinyl or pentinyl, represents respectively optionally cyano-, carboxy-, fluorine-, chlorine-, bromine-methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl- or propionyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, represents respectively optionally cyano-, carboxy-, nitro-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted phenyl, benzyl or phenylethyl, or represents respectively optionally cyano-, carboxy-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, phenyl-, phenoxy- or phenylthio-substituted furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxetanyl, thietanyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiad

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