Substituted 4-benzoylpyrazoles

Details Substituted 4-benzoylpyrazoles Substituted 4-benzoylpyrazoles

1999-06-23

2000-02-22

Ramsuer, Robert W.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

5483657, 5483694, A01N 4356, C07D23120

Patent

active

060280352

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to substituted 4-benzoylpyrazoles of the formula I ##STR1## where the variables have the following meanings: R.sup.1, R.sup.2 are hydrogen, nitro, halogen, cyano, thiocyanato, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, --OR.sup.5, --OCOR.sup.6, --OSO.sub.2 R.sup.6, --SH, --S(O).sub.n R.sup.7, --SO.sub.2 OR.sup.5, --SO.sub.2 NR.sup.5 R.sup.8, --NR.sup.8 SO.sub.2 R.sup.6 or --NR.sup.8 COR.sup.6 ; -haloalkyl, --OR.sup.7, --SR.sup.7 or --NR.sup.7 R.sup.10 ; C.sub.3 -C.sub.6 -alkenyl, C.sub.4 -C.sub.6 -cycloalkenyl, C.sub.3 -C.sub.6 -alkynyl, --COR.sup.9, --CO.sub.2 R.sup.9, --COSR.sup.9 or --CONR.sup.8 R.sup.9, it being possible for the abovementioned alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals and R.sup.9 of the radicals --COR.sup.9, --CO.sub.2 R.sup.9, --COSR.sup.9 and --CONR.sup.8 R.sup.9 to be partially or fully halogenated and/or to have attached to them one to three of the following groups: --NR.sup.8 R.sup.10, .dbd.NOR.sup.10, --OCOR.sup.10, --SCOR.sup.10, --NR.sup.8 COR.sup.10, --CO.sub.2 R.sup.10, --COSR.sup.10, --CONR.sup.8 R.sup.10, C.sub.1 -C.sub.4 -alkyliminooxy, C.sub.1 -C.sub.4 -alkoxyamino, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, it being possible for the eight last-mentioned radicals, in turn, to be substituted; C.sub.1 -C.sub.6 -alkoxy-C.sub.2 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl; -C.sub.6 -alkoxy-C.sub.2 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl; -C.sub.6 -alkynyl, phenyl or benzyl; -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl; ##STR2## which is linked in the 4-position and where R.sup.11 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, phenyl or phenyl which is partially or fully halogenated and/or has attached to it one to three of the following radicals: -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy; C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -haloalkylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -haloalkylsulfonyl, phenylcarbonyl, phenylcarbonylmethyl, phenoxycarbonyl or phenylsulfonyl, the four last-mentioned substituents being unsubstituted or the phenyl ring being in each case partially or fully halogenated and/or having attached to it one to three of the following radicals: -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy; -haloalkyl;
Moreover, the invention relates to processes and intermediates for the preparation of compounds of the formula I, to compositions which comprise the latter, and to the use of the compounds of the formula I and of the compositions comprising them for controlling weeds.
4-Benzoylpyrazoles are disclosed in the literature, for example in EP-A 282 944.
However, the herbicidal properties of the prior-art compounds and the crop plant tolerances are only partly satisfactory. It was an object of the present invention to find novel, in particular herbicidally active, compounds with improved properties.
This object is achieved by the 4-benzoylpyrazoles of the formula I and by their herbicidal activity.
Furthermore, there have been found herbicidal compositions which comprise the compounds I and which have a very good herbicidal activity. In addition, there have been found processes for the preparation of these compositions and methods of controlling undesirable vegetation using the compounds I.
The present invention also relates to stereoisomers of the compounds of the formula I. These include pure stereoisomers and mixtures of these.
The compounds of the formula I contain a carbon-nitrogen double bond and therefore exist in the form of E isomers or Z isomers or E/Z isomer mixtures. Furthermore, the compounds of the formula I may contain further carbon or carbon-nitrogen double bonds. The invention relat

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Tanaka er al, Chemical Abstracts, vol. 129:302,634, 1998.

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