Substituted aryl ketones

Details Substituted aryl ketones Substituted aryl ketones

2002-03-27

2003-08-26

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S264400

Reexamination Certificate

active

06610631

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to novel substituted aryl ketones, to processes for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
It is already known that certain substituted aryl ketones have herbicidal properties (cf. EP-A-090 262, EP-A-135 191, EP-A-186 118, EP-A-186 119, EP-A-186 120, EP-A-319 075, EP-A-352 543, EP-A-418 175, EP-A-487 357, EP-A-527 036, EP-A-527 037, EP-A-560 483, EP-A-609 797, EP-A-609 798, EP-A-625 505, EP-A-625 508, EP-A-636 622, U.S. Pat. No. 5,804,532, U.S. Pat. No. 5,834,402, U.S. Pat. 5,846,906, U.S. Pat. No. 5,863,865, WO-A-96/26192, WO-A-96/26193, WO-A-96/26200, WO-A-96126206, WO-A-97/27187, WO-A-97/35850, WO-A-97/41105, WO-A-97/41116, WO-A-97/41117, WO-A-97/41118, WO-A-97/43270, WO-A-97/46530, WO-A-98/28981, WO-A-98/31681, WO-A-98/31682, WO-A-99/03856, WO-A-99/07688). However, the activity of these compounds is not entirely satisfactory.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides the novel substituted aryl ketones of the general formula (I)
in which
n represents the numbers 0, 1 or 2,
A represents a single bond or represents alkanediyl,
R
1
represents hydrogen or represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R
2
represents hydrogen, amino, or represents in each case optionally substituted alkyl, alkoxy, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkinyl, alkinyloxy, cycloalkyl, cycloalkylalkyl, aryl, arylamino or arylalkyl,
R
3
represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkyl-amino, dialkylamino or dialkylaminosulphonyl,
R
4
represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkyl-amino, dialkylamino or dialkylaminosulphonyl, and
Z represents one of the groupings below
where
m represents the numbers 0 to 6,
R
5
represents halogen or represents in each case optionally substituted alkyl or alkylthio, or—if m represents 2-together with a second radical R
5
represents alkanediyl (alkylene),
R
6
represents hydroxyl, formyloxy, or represents in each case optionally substituted alkoxy, alkylthio, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy, alkinyloxy, arylalkyl, aryloxy, arylthio, arylcarbonyloxy, arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy or arylalkylthio,
R
7
represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl or cycloalkyl,
R
8
represents hydrogen or represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R
9
represents hydroxyl, formyloxy, or represents in each case optionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy, alkinyloxy, arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulphonyloxy,
R
10
represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxy-carbonyl or alkylthio,
R
11
represents hydrogen or represents in each case optionally substituted alkyl or cycloalkyl,
R
12
represents hydrogen or represents in each case optionally substituted alkyl or cycloalkyl, and
R
13
represents hydrogen, cyano, carbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl,
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.
Preferred substituents and preferred ranges of the radicals present in the formulae mentioned above and belong are defined below.
A preferably represents a single bond or represents alkanediyl having 1 to 6 carbon atoms.
R
1
preferably represents hydrogen, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally cyano- or halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety.
R
2
preferably represents hydrogen, amino, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alklylamino or di-alkylamino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano- or halogen-substituted alkenyl, alkenyloxy, alkinyl or alkinyloxy having in each case 2 to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted aryl, arylamino or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety.
R
3
preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thio-carbamoyl, halogen, or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkyl-aminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups.
R
4
preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thio-carbamoyl, halogen, or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkyl-aminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups.
m preferably represents the numbers 0, 1, 2, 3 or 4.
R
5
preferably represents halogen or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl or alkylthio having in each case 1 to 6 carbon atoms, or optionally also—if m represents 2—together with a second radical R
5
represents alkanediyl (alkylene) having 2 to 6 carbon atoms.
R
6
preferably represents hydroxyl, formyloxy, or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkoxy, alkylthio, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkyl-sulphonyloxy having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano- or halogen-substituted alkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms, or represents in each case optionally nitro-, cyano-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted arylalkyl, aryloxy, arylthio, arylcarbonyloxy, arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy or arylalkylthio having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety.
R
7
preferably represents hydrogen,

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