Substituted 4-benzoylpyrazoles

Details Substituted 4-benzoylpyrazoles Substituted 4-benzoylpyrazoles

2000-06-06

2002-06-18

Trinh, Ba K. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S281700, C548S204000, C548S236000, C548S247000, C548S517000, C549S060000, C549S332000, C549S214000, C549S473000, C549S510000, C549S554000, C549S561000

Reexamination Certificate

active

06407268

ABSTRACT:

The present invention relates to substituted 4-benzoylpyrazoles of the formula I
where:
R
1
and R
2
are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, —OR
10
, —OCOR
10
, —OSO
2
R
10
, —S(O)
n
R
10
, —SO
2
OR
10
, —SO
2
NR
3
R
10
, —NR
10
SO
2
R
10
or —NR
10
COR
10
;
Q is a pyrazole of the formula II,
 which is attached in position 4 and where
R
11
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, phenyl or phenyl which is partially or fully halogenated and/or carries one to three of the following radicals: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy;
R
12
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-haloalkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-haloalkylsulfonyl, phenylcarbonyl, phenylcarbonylmethyl, phenoxycarbonyl or phenylsulfonyl,
where the last four substituents are unsubstituted or the phenyl ring in question is partially or fully halogenated and/or carries one to three of the following radicals: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy , C
1
-C
4
-haloalkoxy;
R
13
is hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl;
A is a group of the formula IIIa, IIIb or IV
 where:
R
3
is hydrogen, C
1
-C
6
-alkyl or phenyl, where the alkyl and phenyl radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups:
hydroxy, mercapto, amino, cyano, R
10
, —OR
10
, —SR
10
, —NR
3
R
10
, ═NOR
10
, —OCOR
10
, —SCOR
10
, —NR
3
COR
10
, —CO
2
R
10
, —COSR
10
, —CONR
3
R
10
, C
1
-C
4
-alkyliminooxy, C
1
-C
4
-alkoxyamino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxy-C
2
-C
6
-alkoxycarbonyl, C
1
-C
4
-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals may in turn be substituted;
R
4
-R
7
may be identical or different and, independently of the others, each is:
hydrogen, hydroxyl, mercapto, amino, halogen, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
4
-C
6
-cycloalkenyl, phenyl, —OR
10
, —S(O)
n
R
10
, —OS(O)
n
R
10
, —PO(OR
10
)
2
, —NR
3
R
10
, —Si(R
10
)
3
or —OCOR
10
,
where the alkyl and cycloalkyl radicals mentioned and R
3
and R
10
of the radicals —OR
10
, —S(O)
n
R
10
, —OS(O)
n
R
10
, —PO(OR
10
)
2
, —NR
3
R
10
, —Si(R
10
)
3
, —OCOR
10
may be partially or fully halogenated, and
the unsubstituted or partially halogenated alkyl, cycloalkyl and R
3
radicals optionally carry one to three of the following groups: hydroxyl, mercapto, amino, cyano, R
10
, —OR
10
, —SR
10
, —NR
3
R
10
, ═NOR
10
, —OCOR
10
, —SCOR
10
, —NR
3
COR
10
, —CO
2
R
10
, —COSR
10
, —CONR
3
R
10
, C
1
-C
4
-alkyliminooxy, C
1
-C
4
-alkoxyamino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxy-C
2
-C
6
-alkoxycarbonyl, C
1
-C
4
-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals may in turn be substituted, and
the unsubstituted or partially halogenated R
10
radicals optionally carry one to three of the following groups: hydroxyl, mercapto, amino, cyano, C
1
-C
4
-alkyliminooxy, C
1
-C
4
-alkoxyamino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxy-C
2
-C
6
-alkoxycarbonyl, C
1
-C
4
-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals may in turn be substituted;
R
4
and R
5
together may form a C
2
-C
5
-alkylene- or C
2
-C
5
-alkenylene chain which may be interrupted once or twice by a nitrogen or an oxygen atom, or may form a group ═X, where X is an oxygen atom or a group CR
3
R
10
, NR
10
, NNR
3
R
10
or NOR
10
;
R
6
and R
7
together may form a C
2
-C
5
-alkylene- or C
2
-C
5
-alkenylene chain which may be interrupted once or twice by a nitrogen or an oxygen atom, or may form a group ═X, where X is an oxygen atom or a group CR
3
R
10
, NR
10
, NNR
3
R
10
or NOR
10
;
n is zero, one, two;
R
5
and R
6
together may furthermore, if they are attached to adjacent carbon atoms and if R
4
and R
7
are hydrogen, form a C
3
-C
4
-alkylene or C
3
-C
4
-alkenylene chain which may be interrupted by a nitrogen or an oxygen atom;
R
8
and R
9
may be identical or different and, independently of the other, each is:
hydrogen, nitro, halogen, cyano, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
4
-C
6
-cycloalkenyl, C
5
-C
6
-heterocyclyl, —OR
10
, —SR
10
, —COR
10
, —COOR
10
, —CONR
3
R
10
, phenyl, phenyl-C
1
-C
6
-alkyl and five- or six-membered hetaryl,
where the alkyl and cycloalkyl radicals mentioned and R
3
and R
10
of the radicals —OR
10
, —SR
10
, —COR
10
, —COOR
10
, —CONR
3
R
10
may be partially or fully halogenated, and
the unsubstituted or partially halogenated alkyl, cycloalkyl and R
3
radicals optionally carry one to three of the following groups: hydroxyl, mercapto, amino, cyano, R
10
, —OR
10
, —SR
10
, —NR
3
R
10
, ═NOR
10
, —OCOR
10
, —SCOR
10
, —NR
3
COR
10
, —CO
2
R
10
, —COSR
10
, —CONR
3
R
10
, C
1
-C
4
-alkyliminooxy, C
1
-C
4
-alkoxyamino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxy-C
2
-C
6
-alkoxycarbonyl, C
1
-C
4
-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals may in turn be substituted, and
the unsubstituted or partially halogenated R
10
radicals optionally carry one to three of the following groups: hydroxyl, mercapto, amino, cyano, C
1
-C
4
-alkyliminooxy, C
1
-C
4
-alkoxyamino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxy-C
2
-C
6
-alkoxycarbonyl, C
1
-C
4
-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals may in turn be substituted;
R
10
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, phenyl or phenyl-C
1
-C
6
-alkyl, where the alkyl radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups: hydroxyl, mercapto, amino, cyano, C
1
-C
4
-alkyliminooxy, C
1
-C
4
-alkoxyamino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxy-C
2
-C
6
-alkoxycarbonyl, C
1
-C
4
-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals may in turn be substituted;
and agriculturally useful salts thereof.
In addition, the invention relates to processes and intermediates for preparing compounds of the formula I, to compositions comprising them, and to the use of the compounds of the formula I and to compositions comprising them for controlling harmful plants.
4-Benzoylpyrazoles are disclosed in the literature, for example in EP-A 282 944.
However, the herbicidal properties of the prior art compounds and their crop plant safety are not entirely satisfactory. It is an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.
We have found this object is achieved by the 4-benzoylpyrazoles of the formula I and their herbicidal activity.
Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal activity. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
The present invention also provides stereoisomers of the compounds of the formula I. Pure stereoisomers and also mixtures thereof are included.
Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers and, if this is the case, are present as mixtures of enantiomers or diastereomers. The invention provides the pure enantiomers or diastereomers and also mixtures thereof.
The compounds of the formula I may also be present in the form of their agriculturally useful salts, the kind of salt generally not being important. The salts of those cations or the acid addition salts of those acids whose cations or anions, respect

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