&agr;,&agr;′-substituted...

Details &agr;,&agr;′-substituted... &agr;,&agr;′-substituted...

2002-01-03

2003-05-20

Ramsuer, Robert W. (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S369400

Reexamination Certificate

active

06566307

ABSTRACT:

The present invention relates to &agr;,&agr;′-substituted N-alkyl-3-alkenylbenzoylpyrazole derivatives of the formula I
where:
R
1
is hydrogen, nitro, halogen, cyano, thiocyanato, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylthio, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl;
R
2
is —S(O)
n
R
10
, —SO
2
OR
11
, —SO
2
NR
11
R
12
, —NR
12
SO
2
R
13
, —NR
12
COR
13
, —PO(OR
14
)(OR
15
);
R
3
is hydrogen, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl;
R
4
, R
5
are hydrogen, nitro, halogen, cyano, thiocyanato, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
4
-C
6
-cycloalkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkoxy, —COR
14
, —CO
2
R
14
, —COSR
14
, —CONR
14
R
15
, —C(R
16
)═NR
17
, —PO(OR
14
)(OR
15
), C
1
-C
4
-alkyl, which carries a radical from the following group: —COR
14
, —CO
2
R
14
, —COSR
14
, —CONR
14
R
15
or —C(R
16
)═NR
17
; heterocyclyl, heterocyclyl-C
1
-C
4
-alkyl, phenyl, phenyl-C
1
-C
4
-alkyl, hetaryl or hetaryl-C
1
-C
4
-alkyl, where the six last-mentioned radicals may be substituted;
or
R
4
and R
5
together form a C
2
-C
6
-alkanediyl chain which may be mono- to tetrasubstituted by C
1
-C
4
-alkyl and/or may be interrupted by oxygen or sulfur or an unsubstituted or C
1
-C
4
-alkyl-substituted nitrogen;
R
6
is hydrogen, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
3
-C
8
-cycloalkyl;
R
7
, R
8
, R
9
are hydrogen, C
1
-C
6
-alkyl, where the alkyl group may be unsubstituted or mono- or polysubstituted by halogen or cyano and the radicals R
7
, R
8
and R
9
are in each case identical or different, but at most one of the radicals from the group R
7
, R
8
and R
9
is hydrogen;
n is 0, 1 or 2;
R
10
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy-C
2
-C
6
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
R
11
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy-C
2
-C
6
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
R
12
is hydrogen or C
1
-C
6
-alkyl;
R
13
is C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl;
R
14
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, phenyl or benzyl, where the two last-mentioned radicals may be partially or fully halogenated and/or may carry one to three radicals from the following group: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylcarbonyl or C
1
-C
4
-alkoxycarbonyl;
R
15
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
or
R
14
and R
15
together form a C
2
-C
6
-alkanediyl chain which may be mono- to tetrasubstituted by C
1
-C
4
-alkyl and/or may be interrupted by oxygen or sulfur or an unsubstituted or C
1
-C
4
-alkyl-substituted nitrogen;
R
16
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkoxycarbonyl, C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, phenyl or benzyl, where the two last-mentioned radicals may be partially or fully halogenated and/or may carry one to three radicals from the following group: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylcarbonyl or C
1
-C
4
-alkoxycarbonyl;
R
17
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
3
-C
6
-cycloalkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, phenyl, benzyl or benzyloxy, where the three last-mentioned radicals may be partially or fully halogenated and/or may carry one to three radicals from the following group: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylcarbonyl or C
1
-C
4
-alkoxycarbonyl;
and their tautomers and agriculturally useful salts.
Moreover, the invention relates to processes for preparing compounds of the formula I, to compositions comprising them and to the use of the compounds of the formula I and of the compositions comprising them in the agronomic field, in particular for controlling undesirable vegetation.
Herbicidally active compounds of the class of the benzoylpyrazoles are disclosed, for example, in EP-A 282 944; WO 98/42677; WO 98/45273; WO98/50366; WO 98/52926; WO 98/56766; U.S. Pat. No. 5,807,806.
However, the herbicidal properties of these compounds and their compatibility with crop plants are not entirely satisfactory.
It is an object of the present invention to provide novel compounds having improved properties which can be used as active compounds in crop protection, in particular as herbicides.
We have found that this object is achieved by the benzoylpyrazoles defined above, which are substituted in the 1-position of the pyrazole derivative by a branched alkyl group. This branched alkyl group is characterized by the substitutent —CR
7
R
8
R
9
on the pyrazole ring.
Furthermore, we have found highly effective compositions comprising the compounds I. 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. This includes both pure stereoisomers and mixtures thereof.
The compounds of the formula I contain a carbon-carbon double bond and are therefore present as E isomers or as z isomers or as E/Z isomer mixtures. Furthermore, the compounds of the formula I can contain further carbon or carbon-nitrogen double bonds. The invention provides both the pure geometric isomers and mixtures thereof.
Likewise, depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they are present as enantiomers or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers and mixtures thereof.
The compounds of the formula I can also be present in the form of their tautomers or as tautomer mixtures. The tautomeric forms result in particular owing to the hydroxyl substituent at the pyrazole ring. Thus, the compounds can be referred to both as 5-hydroxypyrazoles and as 5-oxo-pyrazolinones.
The present invention also provides precursors which afford compounds I by chemical conversion or biological degradation. Such precursors of compounds I are, for example, esters or ether derivatives of functional hydroxyl groups.
The compounds of the formula I can also be present in the form of their agriculturally useful salts, the type of salt generally being immaterial. In general, the salts of those cations or the acid addition salts of those acids are suitable whose cations and anions, respectively, do not adversely affect the herbicidal action of the compounds I.
Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced by C
1
-C
4
-alkyl or hydroxy-C
1
-C
4
-alkyl and/or one phenyl or benzyl, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C
1
-C
4
-alkyl)-sulfonium and sulfoxonium ions, preferably tri(C
1
-C
4
-alkyl)-sulfoxonium.
Anions of suitable acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate.
Essential for the invention for the purpose of the present invention are compounds of the formula I which are substituted by a branched alkyl group —CR
7
R
8
R
9
in the 1-position of the pyrazole ring. These are in particular those compounds I in which at most one of the radicals from the group consisting of R

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