Substituted benzoyl ketones, methods for producing them and...

Details Substituted benzoyl ketones, methods for producing them and... Substituted benzoyl ketones, methods for producing them and...

2001-11-05

2004-07-13

Kifle, Bruck (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C514S384000, C548S263200, C548S263400

Reexamination Certificate

active

06762152

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to novel substituted benzoyl ketones, to processes for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
It is already known that certain substituted benzoyl ketones have herbicidal properties. (cf. EP-A-625505, EP-A-625508, U.S. Pat. No. 5,804,532, U.S. Pat. No. 5,846,906, WO-A-96/26193). However, the activity of these compounds is not entirely satisfactory.
This invention, accordingly, provides the novel substituted benzoyl ketones of the formula (I),
in which
n represents 0, 1, 2 or 3,
A represents a single bond or represents alkanediyl (alkylene),
R
1
represents hydrogen or represents in each case optionally substituted alkyl or cycloalkyl,
R
2
represents hydrogen, cyano, carbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl,
R
3
represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl,
R
4
represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, and
DETAILED DESCRIPTION
Z represents an optionally substituted 4- to 12-membered, saturated or unsaturated, monocyclic or bicyclic, heterocyclic grouping which contains 1 to 4 hetero atoms (up to 4 nitrogen atoms and optionally—alternatively or additionally—one oxygen atom or one sulphur atom, or one SO grouping or one SO
2
grouping) and which additionally contains one to three oxo groups (C═O) and/or thioxo groups (C═S) as components of the heterocycle,
including all possible tautomeric forms of the compounds of the general formula (I) and the possible salts 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.
n preferably represents 0, 1 or 2.
A preferably represents a single bond or represents alkanediyl (alkylene) having 1 to 4 carbon atoms.
R
1
preferably represents hydrogen, represents optionally cyano, carboxyl, carbamoyl, halogen, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl- or C
1
-C
4
-alkylsulphonyl-substituted alkyl having 1 to 6 carbon atoms, or represents optionally cyano-, carboxyl-, carbamoyl-, halogen-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms.
R
2
preferably represents hydrogen, cyano, carbamoyl, halogen, represents in each case optionally cyano-, carbamoyl-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, or represents in each case optionally halogen-substituted alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms.
R
3
preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, represents in each case optionally halogen-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl- or C
1
-C
4
-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 4 carbon atoms in the alkyl groups, or represents alkylamino, dialkylamino or dialkylaminosulphonyl having in each case up to 4 carbon atoms in the alkyl groups.
R
4
preferably represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, represents in each case optionally halogen-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl- or C
1
-C
4
-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 4 carbon atoms in the alkyl groups, or represents alkylamino, dialkylamino or dialkylaminosulphonyl having in each case up to 4 carbon atoms in the alkyl groups.
Z preferably represents one of the heterocyclic groupings below
where the dotted line is in each case a single bond or a double bond, and each heterocyclic grouping preferably only carries two substituents of the definition R
5
and/or R
6
,
Q represents oxygen or sulphur,
R
5
represents hydrogen, hydroxyl, mercapto, cyano, halogen, represents in each case optionally cyano-, halogen-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl- or C
1
-C
4
-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkylamino or dialkylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl, alkenyloxy, alkenylthio or alkenylamino having in each case up to 6 carbon atoms in the alkenyl- or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, or—if two adjacent radicals R
5
and R
5
are located at a double bond—together with the adjacent radical R
5
also represents a benzo grouping, and
R
6
represents hydrogen, hydroxyl, amino, alkylideneamino having up to 4 carbon atoms, represents in each case optionally halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylamino, dialkylamino or alkanoylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl or alkenyloxy having in each case up to 6 carbon atoms in the alkenyl- or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkylalkyl or cycloalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted phenyl or benzyl, or together with an adjacent radical R
5
or R
6
represents optionally halogen- or C
1
-C
4
-alkyl-substituted alkanediyl having 3 to 5 carbon atoms,
where the individual radicals R
5
and R
6
—if a plurality of them are attached to the same heterocyclic grouping—can have identical or different meanings within the scope of the above definition.
Q preferably represents oxygen.
R
5
preferably represents hydrogen, hydroxyl, mercapto, cyano, fluorine, chlorine, bromine, iodine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substituted 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, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, di-n-propylamino or di-i-propylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, butenyl, ethinyl, propinyl, butinyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino, represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopent

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