Substituted benzoylpyrazoles as herbicides

Details Substituted benzoylpyrazoles as herbicides Substituted benzoylpyrazoles as herbicides

2001-09-26

2004-06-08

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S265000, C504S270000, C504S271000, C504S273000, C504S277000, C504S278000, C504S282000, C548S132000, C548S213000, C548S230000, C548S229000, C548S227000, C548S244000, C548S243000, C548S263200, C548S263800, C548S312400, C548S364100, C548S365100

Reexamination Certificate

active

06746989

ABSTRACT:

The invention relates to novel substituted benzoylpyrazoles, to processes for their preparation and to their use as herbicides.
It is already known that certain substituted benzoylpyrazoles have herbicidal properties (cf. EP-A-352543, WO-A-96/26206, WO-A-97/35850, WO-A-97/41105, WO-A-97/41116, WO-A-97/41117, WO-A-97/41118, WO-A-97/46530, WO-A98/28981, WO-A-98/31681, WO-A-98/31682, WO-A-99/07697). However, the activity of these compounds is not entirely satisfactory.
This invention now provides the novel substituted benzoylpyrazoles of the general formula (I)
in which
n represents the numbers 0, 1, 2 or 3,
A represents a single bond or represents alkanediyl(alkylene),
R
1
represents in each case optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl,
R
2
represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkoxycarbonyl or cycloalkyl,
R
3
represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl,
R
4
represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl,
Y represents hydrogen or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenyl, alkenylcarbonyl, alkenylsulfonyl, alkinyl, alkinylcarbonyl, cycloalkyl, cycloalkylcarbonyl, cycloalkylalkyl, phenylcarbonyl, phenylsulfonyl, phenylalkyl or phenylcarbonylalkyl, and
Z represents an optionally substituted 4- to 12-membered saturated or unsaturated monocyclic or bicyclic heterocyclic grouping which contains 1 to 4 heteroatoms (up to 4 nitrogen atoms and optionally—alternatively or additionally—one oxygen atom or one sulfur atom, or an SO grouping or an SO
2
grouping) and which additionally contains one to three oxo groups (C═O) and/or thioxo groups (C═S) as component 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 the numbers 0, 1 or 2.
A preferably represents a single bond or represents alkanediyl(alkylene) having 1 to 4 carbon atoms.
R
1
preferably represents optionally cyano-, carboxyl-, carbamoyl-, halogen-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkyl-carbonyl-, C
1
-C
4
-alkoxy-carbonyl-, C
1
-C
4
--alkylthio-, C
1
-C
4
-alkylsulfinyl- or C
1
-C
4
-alkylsulfonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen- or C
1
-C
4
-alkoxy-carbonyl-substituted alkenyl or alkinyl having in each case 2 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, thiocarbamoyl, halogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, represents optionally halogen-substituted alkylthio having 1 to 6 carbon atoms, or represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl having 3 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
-alkylsulfinyl- or C
1
-C
4
-alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case up to 4 carbon atoms in the alkyl groups, or represents alkylamino, dialkylamino or dialkylaminosulfonyl 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
-alkylsulfinyl- or C
1
-C
4
-alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case up to 4 carbon atoms in the alkyl groups, or represents alkylamino, dialkylamino or dialkylaminosulfonyl having in each case up to 4 carbon atoms in the alkyl groups.
Y preferably represents hydrogen, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen- or C
1
-C
4
-alkoxycarbonyl-substituted alkyl, alkylcarbonyl or alkoxycarbonyl having in each case up to 6 carbon atoms, represents in each case optionally halogen-substituted alkylsulfonyl, alkylaminocarbonyl or dialkylaminocarbonyl having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen- or C
1
-C
4
-alkoxy-carbonyl-substituted alkenyl, alkenylcarbonyl, alkinyl or alkinylcarbonyl having in each case 2 to 6 carbon atoms, represents optionally halogen-substituted alkenylsulfonyl having up to 6 carbon atoms represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl, cycloalkylcarbonyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-, carboxyl-, carbamoyl-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted phenylcarbonyl, phenylsulfonyl, phenyl-C
1
-C
4
-alkyl or phenylcarbonyl-C
1
-C
4
-alkyl.
Z preferably represents one of the heterocyclic groupings below
 in which in each case the broken bond is a single bond or a double bond,
Q represents oxygen or sulfur,
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
-alkylsulfinyl- or C
1
-C
4
-alkylsulfonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case up to 6 carbon atoms in the alkyl groups, represents propadienylthio, represents in each case optionally halogen-substituted alkylamino or dialkylamino heaving 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 cycolalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl moiety, 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, represents pyrrolidino, piperidino or morpholino, or—if two adjacent radicals R
5
and R
5
are located on 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

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