Heterocyclic substituted 4-benzoyl-pyrazole as herbicides

Details Heterocyclic substituted 4-benzoyl-pyrazole as herbicides Heterocyclic substituted 4-benzoyl-pyrazole as herbicides

2000-02-07

2001-03-27

Aulakh, C. S. (Department: 1612)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S365100, C548S364100, C548S365700, C546S276100, C504S130000, C504S139000, C504S244000, C504S282000

Reexamination Certificate

active

06207618

ABSTRACT:

This application is a 371 of PCT/EP98/04635 Jul. 23, 1998 now WO 99/10328 Mar. 4, 1999.
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
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, —OR
3
, —OCOR
3
, —OSO
2
R
3
, —S(O)
n
R
3
, —SO
2
OR
3
, —SO
2
N(R
3
)
2
, —NR
3
SO
2
R
3
or —NR
3
COR
3
;
R
3
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 abovementioned alkyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
hydroxyl, mercapto, amino, cyano, R
3
, —OR
3
, —SR
3
, —N(R
3
)
2
, ═NOR
3
, —OCOR
3
, —SCOR
3
, —NR
3
COR
3
, —CO
2
R
3
, —COSR
3
, —CON(R
3
)
2
, 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 eight last-mentioned radicals may in turn be substituted;
n is 0, 1 or 2;
Q is a pyrazole of the formula II
 which is attached in position 4 and where
R
4
is hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl;
R
5
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, phenyl or phenyl which may be partially or fully halogenated and/or may carry 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
6
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 four last-mentioned substituents are unsubstituted, or the phenyl ring in question may be partially or fully halogenated and/or may carry 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;
X
1
is a straight-chain or branched C
1
-C
6
-alkylene, a C
2
-C
6
-alkenylene or a C
2
-C
6
-alkynylene chain which is interrupted by a hetero atom selected from the group consisting of:
oxygen and sulfur,
where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:
—OR
7
, —OCOR
7
, —OCONHR
7
or —OSO
2
R
7
;
R
7
is hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, phenyl, phenyl-C
1
-C
6
-alkyl, where the abovementioned alkyl, alkenyl or alkynyl radicals may be partially or fully halogenated and/or may be substituted by one or more of the following radicals:
hydroxyl, mercapto, amino, cyano, nitro, formyl, C
1
-C
4
-alkylamino, C
1
-C
4
-dialkylamino, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkylcarbonyloxy, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy;
Het is a three- to six-membered partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the following three groups:
nitrogen,
oxygen in combination with at least one nitrogen or
sulfur in combination with at least one nitrogen,
where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R
8
;
R
8
is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C
1
-C
4
-alkylamino, C
1
-C
4
-dialkylamino, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkylcarbonyloxy, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, where the alkyl radicals may in each case be substituted by in each case one or more of the following radicals:
cyano, formyl, C
1
-C
4
-alkylamino, C
1
-C
4
-dialkylamino, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkylcarbonyloxy, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy;
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 of 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 according to the invention 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 enantiomers or mixtures of 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, respectively, do not adversely affect the herbicidal activity of the compounds I are generally suitable.
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 ammonium, where, if desired, one to four hydrogen atoms may be replaced by C
1
-C
4
-alkyl or hydroxyl-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 useable acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate.
Process A:
Reactions of pyrazoles of the formula II (where R
6
=H) with an activated carboxylic acid IIIa or a carboxylic acid IIIb, which is preferably activated in situ, to give the acylation product V, and subsequent rearrangements to the compounds of the formula Ia according to the invention.
L
1
is a nucleophilically replaceable leaving group such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, or carboxylate, for example acetate, trifluoroacetate, etc.
The activated carboxylic acid can be employed directly, as in the case of the acyl halides, or be generated in situ, for example by using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic esters, 2-pyridine disulfite/triphenylphosphine, carbonyldiimidazole, etc.
It may be advantageous to carry out the acylation reaction in the presence of a base. The starting materials and the auxiliary base are advantageously employed in equimolar amounts. A slight excess of auxiliary base, for example 1.2 to 1.5 molar equivalents, based on II, may be advantageo

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