MXPA01005566A - 3-(heterocyclyl)-benzoylpyrazole-derivatives - Google Patents

Abstract

The invention relates to 3-(heterocyclyl)-benzoylpyrazole derivatives of formula (I), wherein the variables have the following meanings:X is O, NH or N-alkyl;R1 is nitro, halogen, alkoxy, halogenalkoxy, alkylthio, halogenalkylthio, alkylsulfonyl or halogenalkyl-sulfonyl;R2, R3, R4, R5 are hydrogen, alkyl or halogenalkyl;R6 is halogen, nitro, alkyl halide, alkoxy, halogenalkoxy, alkylthio, halogenalkylthio, alkylsulfonyl or halogenalkylsulfonyl;R7 is hydroxy, alkoxy, alkenyloxy, alkylsulfonyloxy, alkylcarbonyloxy, (alkylthio)carbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, and the phenyl radical can be substituted;R8, R9 are alkyl;R10 is hydrogen or alkyl;and R11 is hydrogen or alkyl;and to their agriculturally useable salts. The invention also relates to a method for producing these compounds and to their use or the use of products containing them for combating undesirable plants.

Description

DERIVATIVES OF 3- (HETEROCICLI. BENZOYLPIRAZZOL The present invention relates to 3- (heterocyclic) benzoylpyrazole derivatives of the f or mu I wherein: X is O, _ H or N (C: -C6 alkyl); R 1 is nitro, halogen, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy C 4 -C 4 alkylthio, C 1 -C 4 haloalkylthio C 4 -C 4 alkylsulfonyl, or C 4 -C 4 haloalkylsulfonyl; R2, RJ, R4,?. ", Are hydrogen, C_-C alkylene or C9_Chaloalkyl, R6 is halogen, nitro, haloC1-C, alkoxy C: -C4, haloalkoxyC? ~ C, alkylthio C : - C -C4 haloalkylthio / C_-C4 alkylsulfonyl or haloalkylsulfonyl C? -C; R7 is hydroxyl, C? -C_ alkoxy, C3-C6 alkenyloxy, C? -C6 alkylsulfonyloxy, alkylcarbonyloxy C.-Ce, (alkylthio) C 1 -C 4 -carbonyloxy, phenylsulphonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned can ultimately be partially or totally halogenated and / or can carry one to three of the following groups: nitro, cyano , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 4 C alkoxy or C 1 -C haloalkoxy; R8, R9 are C? -C alkyl; R 10 is hydrogen or Cj.-C 4 alkyl; where the number of carbon atoms of the radicals R8, R9 and R10 together is at most 7; R11 is hydrogen or C? -C4 alkyl; and its useful salts in agriculture. In addition, the invention relates to intermediates and processes for the preparation of compounds of formula I, to compositions comprising them and to the use of these derivatives or of compositions comprising them to control harmful plants. Pyrazol-4-yl benzoyl derivatives are disclosed in the literature, for example, in WO 96/26206 and WO 98/31681. However, the herbicidal properties of the compounds of the prior art and their compatibility with crop plants are not entirely satisfactory. It is an object of the present invention to offer novel, particularly herbicidally active compounds having improved properties. We have found that this object is achieved through 3- (heterocyclic) benzoylpyrazole derivatives of the formula I and its herbicidal action. In addition, we have found herbicidal compositions comprising the compounds I and have a very good herbicidal action. In addition, we have found processes for the preparation of these compositions and methods for controlling undesirable vegetation using the compounds I. According to the substitution pattern, the compounds of the formula I can contain one or several chiral centers, in which case they are present as enantiomers or mixtures of the diastereomers. The invention offers both pure enantiomers or diastereomers and their mixtures. The compounds of the formula I can also be present in the form of their salts useful for agriculture, the type of salt is usually not a relevant factor. In general, the salts of the cations or the acid addition salts of the acids whose cations and anions, respectively, do not adversely affect the herbicidal action of the compounds I are suitable. Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, wherein, if desired, one to four hydrogen atoms may be replaced by C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy C 1 -C 4 alkyl / C 1 -C 4 hydroxyalkoxy C 1 -C 4 alkyl -C4 / phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxyeth-1-oxy) et-1-ylammonium, di (2-hydroxyethyl-1-yl) ammonium, trimethylbenzyl onium , in addition phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4) alkyl sulfonium ions, and sulfoxonium ions, preferably tri (C 1 -C 4 alkyl) sulfoxonium. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogensulfate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of alkanoic d-C4 acids, preferably format, acetate, propionate and butyrate. The organic moieties mentioned for the substituents R1-R "or as radicals on phenyl rings are collective terms for individual enumerations of the individual group members, all the hydrocarbon chains, ie all the alkyl, alkylcarbonyl, haloalkyl, alkoxy, haloalkoxy, alkylcarbonyloxy, (alkylthio) carbonyloxy, alkylsulfonyloxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, alkenyl and alkenyloxy can be straight or branched chain Unless otherwise indicated, halogenated substituents preferably carry one to five identical or different halogen atoms The term "halogen" in each case represents fluorine, chlorine, bromine or iodine Examples of significant others are: - alkyl C 1 -C 4, and alkyl portions of C 1 -C 4 alkylcarbonyl and C 1 -C 4 alkylcarbonyloxy: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl or; - C 1 -C 4 alkyl, and the C 1 -C 6 alkylcarbonyl and C 1 -C 4 alkylcarbonyloxy alkyl portions: C 1 -C 4 alkyl according to the above, and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3 methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1 , 2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-trimethylpropyl, 1-ethyl-1 -methylpropyl and l-ethyl-3-methylpropyl; - C 1 -C 4 haloalkyl: a C 1 -C 4 alkyl radical according to the above mentioned partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, 1-iodoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, , 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, -fluoropropyl, 2, 2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3, 3, 3 -trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromoethyl, 4-fluorobutyl , 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl; C 1 -C 4 alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-di ethylethoxy; - CI-C0-alkoxy: C: -C-alkoxy in accordance with that mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1,2-dimethylpropoxy, 2, 2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl- 2-methylpropoxy; haloalkoxy C_-C: a C-C alkoxy radical according to the above mentioned partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, -fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2, 2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2, 2 -dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2, 2-difluoropropoxy, 2,3-difluoropropoxy, 2 , 3-dichloropropoxy, 3, 3, 3-trifluoropropoxy, 3, 3, 3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1- (fluoromethyl) -2-fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy; C-C4 alkylthio, and the alkylthio portions of (alkylthio) carbonyloxy C? -C4: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio; - haloalkylthio C_-C4: they are all a C 1 -C 4 alkylthio radical according to the above mentioned partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, fluoromethylthio difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio , 2-fluoroethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio , 2-chloro-2, 2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2, 2 -difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1- (fluoromethyl) -2-fluoroethylthio, 1- (chloromethyl) -2-chloroethylthio, 1- (bromomethyl) -2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio and nonafluorobutyl iltio; C 1 -C 4 alkylsulfonyl (C 1 -C 4 -alkyl (= 0) 2) and the alkylsulfonyl portions of alkylsulfonyloxy: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2- methylpropylsulfonyl and 1,1-dimethylethylsulfonyl; - C 1 -C 6 alkylsulfonyl, and the alkylsulfonyl portions of C 1 -C 6 alkylsulfonyloxy: a C 1 -C 4 alkylsulfonyl radical as mentioned above, and also, for example, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1- ethyl-1-methylpropylsulfonyl and 1-ethy1-2-methylpropylsulfonyl; haloalkylsulfonyl C 1 -C 4: a C 1 -C 4 alkylsulfonyl radical as mentioned above partially or completely substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2- fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2- bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3, 3, 3- pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloromethyl) -2-chloroethylsulfonyl, 1- (bromomethyl) -2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl and nonafluorobutylsulfonyl; - C3-C6 alkenyloxy: for example prop-1-en-l-yloxy, prop-2-en-yloxy, 1-methylenyloxy, buten-1-yloxy, buten-2-yloxy, buten-3-yloxy, 1- methylprop-l-en-l-yloxy, 2-methylprop-l-en-l-yloxy, l-methylprop-2-en-l-yloxy, 2-methylprop-2-en-l-yloxy, penten-1- iloxy, penten-2-yloxy, penten-3-yloxy, penten-4-yloxy, 1-methylbut-1-en-l-yloxy, 2-methylbut-l-en-l-yloxy, 3-methylbut-l- en-1-yloxy, 'l-methylbut-2-en-l-yloxy, 2-methylbut-2-en-l-yloxy, 3-methylbut-2-en-l-yloxy, l-methylbut-3-en -l-iloxy, 2-methylbut-3-en-l-yloxy, '3-methylbut-3-en-l-yloxy, 1,1-dimethylprop-2-en-l-yloxy, 1,2-dimethylpropyl- l-en-l-yloxy, 1,2-dimethylprop-2-en-l-yloxy, l-ethylprop-l-en-2-yloxy, 1-ethylprop-2-en-l-yloxy, hex-1 en-l-yloxy, hex-2-en-l-yloxy, hex-3-en-l-yloxy, hex-4-en-l-yloxy, hex-5-en-l-yloxy, 1-methylpent- l-en-l-yloxy, 2-methylpent-l-en-l-yloxy, 3-methylpent-l-en-l-yloxy, 4-methylpent-l-en-l-yloxy, 1-methylpent-2- en-l-iloxy, 2-methylpent-2-en-l-yloxy, 3-methylpent-2-en-l-yloxy, 4-methylpent-2-en-l-yloxy, l-methylpent-3-en- l-iloxy, 2-methyl pent-3-en-l-yloxy, 3-methylpent-3-en-l-yloxy, 4-methylpent-3-en-l-yloxy, l-methylpent-4-en-l-yloxy, 2-methylpent- 4-en-l-yloxy, 3-methylpent-4-en-l-yloxy, 4-methylpent-4-en-l-yloxy, 1, l-dimethylbut-2-en-l-yloxy, 1, l- dimethylbut-3-en-l-yloxy, 1,2-dimethylbut-l-en-l-yloxy, 1,2-dimethylbut-2-en-l-yloxy, 1,2-dimethylbut-3-en-l- Ilyloxy, 1,3-dimethylbut-l-en-l-yloxy, 1,3-dimethylbut-2-en-l-yloxy, 1,3-dimethylbut-3-en-l-yloxy, 2, 2-dimethylbut-3-en-l-yloxy, 2,3-dimethylbut-l-en-l-yloxy, 2,3-dimethylbut-2-en-l-yloxy, 2,3-dimethylbut-3- en-l-yloxy, 3, 3-dimethylbut-l-en-l-yloxy, 3, 3-dimethylbut-2-en-l-yloxy, 1-ethylbut-l-en-l-yloxy, l-ethylbutyl- 2-en-l- iloxy, l-etilbut-3-en-li loxi, 2-et ilbut-1-en-1-yloxy, 2-etilbut-2-en-l-iloxi, 2-etilbut-3- en-l-yloxy, 1,1-trimethylprop-2-en-l-yloxy, 1-ethyl-1-meth iprop-2-en-l-yloxy, l-ethyl-2-methylprop-l- en-l-yloxy and l-ethyl-2-methylprop-2-en-l-yloxy; - C3-C6 alkenyl: prop-1-en-l-yl, prop-2-en-l-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1- methylprop-l-en-l-yl, 2-methylprop-l-en-l-yl, 1-methylprop-2-en-l-yl, 2-methylprop-2-en-l-yl, penten-1- ilo, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-l-en-l-yl, 2-methylbut-1-en-l-yl, 3-methylbut-l- en-l-yl, l-methylbut-2-en-1-yl, 2-methylbut-2-en-l-yl, 3-methylbut-2-en-l-yl, 1-methylbut-3-enyl l -yl, 2-methylbut-3-en-l-yl, 3-methylbut-3-en-1-yl, 1, l-dimethylprop-2-en-l-yl, 1,2-dimethylprop-l- en-l-yl, 1,2-dimethylprop-2-en-l-yl, l-ethylprop-l-en-2-yl, 1-ethylprop-2-en-l-yl, hex-1-en- l-ilo, hex-2-en-l-yl, hex-3-en-l-yl, hex-4-en-l-yl, hex-5-en-l-yl, 1-methylpent-l- en-l-yl, 2-methylpent-l-en-l-yl, 3-methylpent-l-en-l-yl, 4-methyl lpent-l-en-1-yl, l-methylpent-2-en -l-ilo, 2-methylpent-2-en-l-yl, 3-methylpent-2-en-l-yl, 4-methylpent-2-en-l-yl, l-methylpent-3-en-l -yl, 2-methylpent-3-en-l-yl, 3-methylpent-3-en-l-yl, 4-methylpent-3-en-l-yl, l-methylpent-4-en-l-yl , 2-m ethylpent-4-en-l-yl, 3-methylpent-4-en-l-yl, 4-methylpent-4-en-l-yl, 1, l-dimethylbut-2-en-l-yl, 1, l-dimethylbut-3-en-l-yl, 1,2-dimethylbut-l-en-l-yl, 1,2-dimethylbut-2-en-l-yl, 1,2-dimethylbut-3-enyl l -yl, 1,3-dimethylbut-l-en-l-yl, 1,3-dimethylbut-2-en-l-yl, 1,3-dimethylbut-3-en-l-yl, 2, 2- dimethylbut-3-en-l-yl, 2,3-dimethylbut-l-en-l-yl, 2,3-dimethylbut-2-en-l-yl, 2,3-dimethylbut-3-en-l- ilo, 3, 3-dimethylbut-l-en-l-yl, 3, 3-dimethylbut-2-en-l-yl, 1-ethylbut-l-en-l-yl, l-ethylbut-2-enyl l -yl, l-ethylbut-3-en-l-yl, 2-ethylbut-l-en-l-yl, 2-ethylbut-2-en-l-yl, 2-ethylbut-3-en-l- ilo, 1, 1, 2-trimethylprop-2-en-l-yl, l-ethyl-l-methylprop-2-en-l-yl, l-ethyl-2-methylprop-l-en-l-yl and l-ethyl-2-methylprop-2-en-l-yl. The phenyl rings are preferably unsubstituted or carry one to three halogen atoms and / or a nitro group, a cyano group, one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy groups. Emphasis is given to these compounds of formula I wherein R7 is hydroxyl, C1-C0 alkoxy, C3-C6 alkenyloxy, alkylsulfonyloxy Ci-Ce, alkylcarbonyloxy Ci-Cβ, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two mentioned substituents may be partially or fully halogenated and / or it may carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 0 haloalkoxy. * Preference is given to the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein: X is O; R1 is nitro, halogen, C_-C alkoxy or C_-C4 alkylthio; particularly preferably nitro, halogen or C 1 -C 4 alkoxy; with particular preference halogen, for example fluorine, chlorine or bromine, or C1-C4 alkoxy, such as methoxy or ethoxy; with chlorine or methoxy being very particularly preferred; R2, R3, R4, R5 are hydrogen, C?-C4 alkyl or C halo-C haloalkyl; particularly preferably hydrogen, methyl, ethyl, propyl, 1-methylethyl, fluoromethyl or chloromethyl; particularly preferably hydrogen, methyl, ethyl or chloromethyl; R 6 is C 1 -C 4 alkylthio or C 1 -C 4 alkylsulfonyl; particularly preferably methylthio, ethylthio or 1-methyl-1-ethylthio, methylsulfonyl, ethylsulfonyl, 1-methylethylsulphonyl or propylsulphonyl; particularly preferably methylsulfonyl, ethylsulfonyl, 1-methylethylsulphonyl or propylsulfonyl; R 7 is hydroxyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkylcarbonyloxy, C 1 -C 4 alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two Substituents mentioned may ultimately be partially or totally halogenated and / or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 4 C 4 alkoxy or C 1 -C 4 haloalkoxy; particularly preferably hydroxyl, C 1 -C 4 alkoxy / C 3 -C 6 alkenyloxy, C 1 -C 4 alkylsulfonyloxy, C 1 -C 4 alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned can ultimately be partial or fully halogenated and / or can carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkoxy C 4 -C 4 alkoxy or C 1 -C haloalkoxy; R8, R9 are C? -C4 alkyl; particularly preferably methyl, ethyl, propyl, 1-methyl-1-ethyl, butyl, 1-methyl-1-propyl and 2-methyl-1-propyl; R 10 is hydrogen or C alquilo-C alkyl; particularly preferably C 1 -C 4 alkyl; methyl, ethyl or propyl being especially preferred; R 11 is hydrogen or C alquilo-C alkyl; particularly preferably hydrogen or methyl. Particularly preferred are 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein X is O; R 1 is halogen or C 1 -C 4 alkoxy; particularly halogen, such as, for example, fluorine, chlorine or bromine or methoxy or ethoxy; with chlorine or methoxy being very particularly preferred; R 6 is C 1 -C 4 alkylsulfonyl; particularly preferably methylsulfonyl, ethylsulfonyl, 1-methyl-1-ethylsulphonyl or propylsulfonyl; R7 is hydroxyl, alkylsulfonyloxy C.-Cß, alkylcarbonyloxy Ci-Ce, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned can ultimately be partially or totally halogenated and / or can carry one to three of the following groups: nitro, cyano, C? -C alkyl C 1 -C 4 haloalkyl C 4 -C 4 alkoxy or C 1 -C 4 haloalkoxy; particularly preferably hydroxyl; R, R- are C? -C alkyl; R 10 is hydrogen or C 1 -C 4 alkyl. Especially preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein R8 is C2-C4 alkyl, for example, ethyl, 1-methyl-1-ethyl, propyl or butyl; R is C 1 -C 4 alkyl, for example methyl or ethyl; R 10 is hydrogen or C? -C alkyl, for example, methyl or ethyl. Also very particularly preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein: R8 is methyl; R 9 is C 1 -C 4 alkyl / for example methyl, ethyl, propyl or butyl; R is C 1 -C 4 alkyl, for example methyl or ethyl.

Also very particularly preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein R 8, R 9 are methyl; R 10 is hydrogen. * Also preferred are 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein: X is O; R is nitro, halogen, C 1 -C 4 alkoxy or C 4 -C 4 alkylthio; particularly preferred is nitro, halogen or C 1 -C 6 alkoxy; with halogen, for example fluorine, chlorine or bromine, or C alco-C alkoxy, for example methoxy or ethoxy being preferred; with chlorine or methoxy being very particularly preferred; R 2, R 3, R 4, R 5 are hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; particularly preferably hydrogen, methyl, ethyl, propyl, 1-methyl-1-ethyl, chloromethyl or fluoromethyl; particularly preferably hydrogen, methyl, ethyl or chloromethyl; particularly preferably hydrogen, methyl, ethyl or chloromethyl; R1 is halogen, nitro, haloalkyl C; -C, C1-C4 alkoxy or C1-C4 haloalkoxy; with particular preference being given to halogen, for example chlorine or bromine, nitro, C 1 -C 2 haloalkyl, such as, for example, difluoromethyl or trifluoromethyl, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy, such as, for example, difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy; R7 is hydroxyl, C6-C6 alkoxy, C3-C6 alkenyloxy, Ci-Cß alkylsulfonyloxy, Ci-Cß alkylcarbonyloxy, C alqu-C4-carbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two mentioned substituents ultimately it may be partially or totally halogenated and / or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; particularly preferably hydroxyl, C 1 -C 4 alkoxy, C 3 -C 6 alkenyloxy, C 1 -C 4 alkylsulfonyloxy, C 1 -C 4 alkylcarbonyloxy,. phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two mentioned substituents can be partially or totally halogenated and / or can carry one of three groups: nitro, cyano, C1-C4 alkyl, haloalkyl C? C4 alkoxy C? ~ C4 or haloalkoxy Cj.-C; R8, R9 are C? -C4 alkyl; particularly preferably methyl, ethyl, propyl, 1-methyl-1-ethyl, butyl, 1-methyl-1-propyl and 2-methyl-1-propyl; R 10 is hydrogen or C 1 -C 4 alkyl; particularly preferably C 1 -C 4 alkyl; with particular preference methyl, ethyl or propyl; R 11 is hydrogen or C 1 -C 4 alkyl; particularly hydrogen or methyl. Particularly preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein X is O; R1 is halogen or C? -C4 alkoxy; with halogen being particularly preferred, such as, for example, fluorine, chlorine or bromine, or methoxy or ethoxy; with chlorine or methoxy being very particularly preferred; R6 is halogen, nitro, haloalkyl C? ~ C4, alkoxy C? ~ C4 or haloalkoxy C ~ C; particularly preferably halogen such as, for example, chlorine or bromine, nitro, C?-C 2 haloalkyl, such as, for example, difluoromethyl or trifluoromethyl, C alco-C 2 alkoxy or C?-C 2 haloalkoxy, such as, for example, difluoromethoxy; R 'is hydroxyl, C 1 -C 6 alkylsulfonyloxy, alkylcarbonyloxy Ci-Cβ, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned can be partially or totally halogenated and / or can carry one of three groups: nitro, cyano, C C-C4 alkyl haloalkyl C? ~ C4, alkoxy C? ~ C4 or haloalkoxy C? -C4; particularly preferably hydroxyl; R8, P are C? -C4 alkyl; R1C is hydrogen or C_-C4 alkyl. Particularly preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein R 8 is C 2 -C alkyl, for example, ethyl, 1-methyl-1-ethyl, propyl or butyl; R * is C 1 -C 4 alkyl, for example methyl or ethyl; R1 is hydrogen or C? -C4 alkyl, for example, methyl or ethyl. Also very particularly preferred are the derivatives of 3- (hereocyclyl) benzoylpyrazole of the formula I wherein R8 is methyl; R 9 is C 1 -C alkyl, for example, methyl, ethyl, propyl or butyl; Ri 0 is C 1 -C 4 alkyl, for example, methyl or ethyl. Also very particularly preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein R 8, R are methyl; R1 '"is hydrogen. * Also preferred are benzoylpyrazoles substituted by 3-he-erocyclyl [sic] of furole I wherein: X is N (C? -C6 alkyl); particularly preferably N-methyl, N-ethyl, N- (1-methyl-1-ethyl) or N-propyl; R 1 is nitro, halogen, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio; with particular preference being given to nitro, halogen or alkoxy C? -C4; with very particular preference halogen such as for example fluorine, chlorine or bromine, or C-C alkoxy such as methoxy or ethoxy; with chlorine or methoxy being very particularly preferred; R 2, R 3, R 4, R 5 are hydrogen, C 1 -C 4 alkyl or haloalkyl, particularly preferably hydrogen, methyl, ethyl, propyl, 1-methyl-1-ethyl, fluoromethyl or chloromethyl; with hydrogen, methyl, ethyl or chloromethyl being particularly preferred; R6 is halogen, nitro, haloalkyl C? -C, alkoxy C? ~ C4, haloalkoxy C? ~ C, alkylthio C1-C4, haloalkylthio C_-C4, alkylsulfonyl C1-C4 or haloalkylsulfonyl C? -C4; with halogen being particularly preferred, for example fluorine, chlorine or bromine, nitro, C1-C4 haloalkyl such as difluoromethyl or trifluoromethyl, C-C4 alkoxy, such as methoxy or ethoxy, haloalkoxy C1-C4, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C?-C 4 alkylthio, for example methylthio or ethylthio, or C?-C 4 alkylsulfonyl, such as, for example, methylsulfonyl, ethylsulfonyl, 1-methyl-1-ethylsulphonyl or propylsulphonyl; R7 is hydroxyl, Ci-Cß alkoxy, C3-C6 alkenyloxy, alkylsulfonyloxy CI-CT, alkylcarbonyloxy CI-CT, (alkylthio) C?-C4-carbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned in Ultimately it may be partially or totally halogenated and / or may carry one of three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; with particular preference being given to hydroxyl, C 1 -C 4 alkoxy, C 3 -C 16 alkenyloxy, C 1 -C 4 alkylsulfonyloxy, C 1 -C 4 alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned can be partially or totally halogenated and / or can carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 4 haloalkoxy; R8, R9 are C? -C4 alkyl; particularly preferably methyl, ethyl, propyl, 1-methyl-1-ethyl, butyl, 1-methyl-1-propyl and 2-methyl-1-propyl; R 10 is hydrogen or C 1 -C 4 alkyl; particularly preferably C 1 -C 4 alkyl; with methyl, ethyl or propyl being particularly preferred; R1 is hydrogen or C4-C4 alkyl; particularly hydrogen or methyl. Particularly preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein R7 is hydroxyl, alkylsulfonyloxyC ± -Ce, alkylcarbonyloxy Ci-Cβ, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned above instance may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, C? -C alkyl, C? -C4 haloalkyl C? -C4 haloalkyl or haloalkyl C:? C; particularly preferably hydroxyl. * Preference is also given to the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein the variables are as defined below: X is 0; R1 is halogen or C? -C alkoxy; with fluorine, chlorine, bromine, methoxy or ethoxy being particularly preferred; with chlorine or methoxy being particularly preferred; R2, R3, R4, R5, are hydrogen; R 6 is C 1 -C 4 alkylsulfonyl; with methylsulfonyl being particularly preferred; R7 is hydroxyl, Ci-Cß alkoxy, C alqu-C4-alkyloxycarbonyloxy or phenylcarbonyloxy, wherein the phenyl radical may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, alkyl C? -C4, haloalkyl C? ~ C4, alkoxy C? C4 or haloalkoxy C? ~ C4; with particular preference being hydroxyl, C: -C4 alkoxy, or phenylcarbonyloxy, wherein the phenyl radical may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, C? -C4 alkyl, haloalkyl C? ? -C, C alkoxy? C4 or haloalkoxy C? -C4; R8, R9 are C? -C4 alkyl; , ' R 10 is hydrogen or C 1 -C 4 alkyl; R is hydrogen. The compounds of the formula are very particularly preferred Ial (= I where R 1 = Cl; Rs, R 5 CH 3; R 10 R 11 = H) in particular compounds Ial. 1 to Ial.300 of Table 1, wherein the definitions of radicals X and R 1 to R 11 are of particular importance for the compounds according to the invention, not only in combination with each other, but in each case, also by themselves.

Table 1: No. X R2 R3 R4 R5 Ial.l 0 H H H H Ial.2 0 H H H H Ial.3 0 H H H H lal.4 0 H H H H Ial.5 0 H H H H Ial.6 0 H H H H Ial.7 0 H H H H Ial.8 0 H H • H H Ial.9 0 H H H H Ial.10 0 H H H H Ial.ll 0 H H H H lal.12 0 H H H H lal.13 0 H H H H Ial.14 0 H H H H Ial.15 0 H H H H Ial.16 0 CH3 H H H Ial.17 0 CH3 H H H Ial.18 0 CH3 H H H Ial.19 0 CH3 H H H Ial.20 0 CH3 H H H Ial.21 0 CH3 H H H Ial.22 0 CH3 H H H Ial.23 0 CH3 H H H Ial.24 0 CH3 H H H Ial.25 0 CH3 H H H Ial.26 0 CH3 H H H Ial.27 0 CH3 H H H Ial.28 0 CH3 H H H Ial.29 0 CH3 H H H Ial.30 0 CH3 H H H Ial.31 0 H H CH3 H Ial.32 0 H H CH3 H Ial.33 0 H H CH3 H lal.34 0 H H CH3 H Ial.35 0 H H CH3 H Ial.36 0 H H CH3 H Ial.37 0 H H CH3 H Ial.38 0 H H CH3 H Ial.39 0 H H CH3 H Ial.40 0 H H CH3 H Ial.41 0 H H CH3 H Ial.42 0 H H CH3 H Ial.43 0 H H CH3 H Ial.44 0 H H CH3 H Ial.45 0 H H CH3 H Ial.46 0 CH3 CH3 H H Ial.47 0 CH3 CH3 H H Ial.48 0 CH3 CH3 H H Ial.49 0 CH3 CH3 H H Ial.50 0 CH3 CH3 H H Ial.51 0 CH3 CH3 H H Ial.52 0. CH3 CH3 H H Ial.53 0 CH3 CH3 H H Ial.54 0 CH3 CH3 H H Ial.55 0 CH3 CH3 H H Ial.56 0 CH3 CH3 H H Ial.57 0 CH3 CH3 H H Ial.58 o 'CH3 CH3 H H Ial.59 0 CH3 CH3 H H Ial.60 0 CH3 CH3 H H lal.61 0 CH3 H CH3 H Ial.62 0 CH3 H CH3 H Ial.63 0 CH3 H CH3 H Ial.64 0 CH3 H CH3 H Ial.65 0 CH3 H CH3 H Ial.66 0 CH3 H CH3 H Ial.67 0 CH3 H CH3 H Ial.68 0 CH3 H CH3 H Ial.69 0 CH3 H CH3 H Ial.70 0 CH3 H CH3 H Ial.71 0 CH3 H CH3 H Ial.72 0 CH3 H CH3 H Ial.73 0 CH3 H CH3 H Ial.74 0 CH3 H CH3 H Ial.75 0 CH3 H CH3 H Ial.76 0 H H CH3 CH3 Ial.77 0 H H CH3 CH3 Ial.78 0 H H CH3 CH3 Ial.79 0 H H CH3 CH3 Ial.80 0 H H CH3 CH3 Ial.81 0 H H CH3 CH3 Ial.82 0 H H CH3 CH3 Ial.83 0 H H CH3 CH3 Ial.84 0 H H CH3 CH3 Ial.85 0 H H CH3 CH3 Ial.86 0 H H CH3 CH3 Ial.87 0 H H CH3 CH3 Ial.88 0 H H CH3 CH3 Ial.89 0 H H CH3 CH3 Ial.90 0 H H CH3 CH3 Ial.91 0 CH3 CH3 CH3 H Ial.92 0 CH3 CH3 CH3 H Ial.93 0 CH3 CH3 CH3 H Ial.94 0 CH3 CH3 CH3 H Ial.95 0 CH3 CH3 CH3 H Ial.96 0 CH3 CH3 CH3 H Ial.97 0 CH3 CH3 CH3 H Ial.98 0 CH3 CH3 CH3 H Ial.99 0 CH3 CH3 CH3 H Ial.100 0 CH3 CH3 CH3 H Ial.101 0 CH3 CH3 CH3 H Ial.102 0 CH3 CH3 CH3 H Ial.103 0 CH3 CH3 CH3 H Ial.104 0 CH3 CH3 CH3 H Ial.105 0 CH3 CH3 CH3 H Ial.106 0 CH3 H CH3 CH3 Ial.107 0 CH3 H CH3 CH3 Ial.108 0 CH3 H CH3 CH3 Ial.109 0 CH3 H CH3 CH3 Ial.110 0 CH3 H CH3 CH3 Ial.lll 0 CH3 H CH3 CH3 Ial.112 0 CH3 H CH3 CH3 Ial.113 0 CH3 H CH3 CH3 Ial.114 0 CH3 H CH3 CH3 Ial.115 0 CH3 H CH3 CH3 Ial.116 0 CH3 H CH3 CH3 Ial.117 0 CH3 H CH3 CH3 Ial.118 0. CH3 H CH3 CH3 Ial.119 0 CH3 H CH3 CH3 Ial.120 0 CH3 H CH3 CH3 Ial.121 0 CH3 CH3 CH3 CH3 Ial.122 0 CH3 CH3 CH3 CH3 Ial.123 0 CH3 CH3 CH3 CH3 Ial.124 0 CH3 CH3 CH3 CH3 Ial.125 0 CH3 CH3 CH3 CH3 Ial.126 _ 0 CH3 CH3 CH3 Ial.127 0 CH3 CH3 CH3 CH3 Ial.128 0 CH3 CH3 CH3 CH3 Ial.129 0 CH3 CH3 CH3 CH3 lal.130 0 CH CH3 Z3 CH3 lal.131 0 CH3 CH3 CH3 CH3 Ial.132 0 CH3 CH3 H3 CH3 Ial.133 0 CH3 CH3 H3 CH3 Ial.134 0 CH3 CH3 H3 CH3 Ial.135 0 CH3 CH3 H3 CH3 Ial.136 0 CH2C1 H H H Ial.137 0 CH2C1 H H H Ial.138 0 CH2C1 H H H Ial.139 0 CH2C1 H H H Ial.140 0 CH2C1 H H H Ial.141 0 CH2C1 H H H Ial.142 0 CH C1 H H H Ial.143 0 CH2C1 H H H Ial.144 0 CH2C1 H H H Ial.145 O CH2C1 H H H Ial.146 0 CH2C1 H H H Ial.147 0 CH2C1 H H H Ial.148 0 CH2C1 H H H Ial.149 0 CH2C1 H H H Ial.150 0 CH2C1 H H H Ial.151 NCH3 H H H H Ial.152 NCH3 H H H H Ial.153 NCH3 H H H H Ial.154 NCH3 H H H H Ial.155 NCH3 H H H H Ial.156 NCH3 H H H H Ial.157 NCH3 H H H H Ial.158 NCH3 H H H H Ial.159 NCH3 H H - H H Ial.160 NCH3 H H H H Ial.161 NCH3 H H H H Ial.162 NCH3 H H H H Ial.163 NCH3 H H H H Ial.164 NCH3 H H H H Ial.165 NCH3 H H H H Ial.166 NCH3 CH3 H H H Ial.167 NCH3 CH3 H H H Ial.168 NCH3 CH3 H H H Ial.169 NCH3 CH3 H H H Ial.170 NCH3 CH3 H H H Ial.171 NCH3 CH3 H H H Ial.172 NCH3 CH3 H H H Ial.173 NCH3 CH3 H H H Ial.174 NCH3 CH3 H H H Ial.175 NCH3 CH3 H H H Ial.176 NCH3 CH3 H H H Ial.177 NCH3 CH3 H H H Ial.178 NCH3 CH3 H H H Ial.179 NCH3 CH3 H H H Ial.180 NCH3 CH3 H H H Ial.181 NCH3 H H CH3 H Ial.182 NCH3 H H CH3 H Ial.183"NCH3 H H CH3 H Ial.184 NCH3 H H CH3 H Ial.185 NCH3 H H CH3 H Ial.186 NCH3 H H CH3 H Ial.187 NCH3 H H CH3 H Ial.188 NCH3 H H CH3 H Ial.189 NCH3 H H CH3 H Ial.190 NCH3 H H CH3 H Ial.191 NCH3 H H CH3 H Ial.192 NCH3 H H CH3 H Ial.193 NCH3 H H CH3 H Ial.194 NCH3 H H CH3 H Ial.195 NCH3 H H CH3 H Ial.196 NCH3 CH3 CH3 H H Ial.197 NCH3 CH3 CH3 H H Ial.198 NCH3 CH3 CH3 H H Ial.199 NCH3 CH3 CH3 H H Ial.200 NCH3 CH3 CH3 H H Ial.201 NCH3 CH3 CH3 H H Ial.202 NCH3 CH3 CH3 H H Ial.203 NCH3 CH3 CH3 H H Ial.204 NCH3 CH3 CH3 H H Ial.205 NCH3 CH; CH3 H H Ial.206 NCH3 CH3 CH5 H H Ial.207 NCH3 CH3 CH3 H H Ial.208 NCH3 CH3 CH3 H H Ial.209 NCH3 CH5 CH3 H H Ial.210 NCH3 CH3 CH3 H H Ial.211 NCH3 CH3 H CH3 H Ial.212 NCH3 CH3 H CH3 H Ial.213 NCH3 CH3 H CH3 H Ial.214 NCH3 CH3 H CH3 H Ial.215 NCH3 CH5 H CH3 H Ial.216 NCH3 CH3 H CH3 H Ial.217 NCH3 CH3 H CH3 H Ial.218 NCH3 CH3 H CH3 H Ial.219 NCH3 CH3 H CH3 H Ial.220 NCH3 CH3 H CH3 H Ial.221 NCH3 CH3 H CH3 H Ial.222 NCH3 CH3 H CH3 H Ial.223 NCH3 CH3 H CH3 H Ial.224 NCH3 CH3 H CH3 H Ial.225 NCH3 CH3 H CH3 H Ial.226 NCH3 H H CH3 CH3 Ial.227 NCH3 H H CH3 CH3 Ial.228 NCH3 H H CH3 CH3 Ial.229 NCH3 H H CH3 CH3 Ial.230 NCH3 H H CH3 CH3 Ial.231 NCH3 H H CH3 CH3 Ial.232 NCH H H CH3 CH3 Ial.233 NCH3 H H CH3 CH3 Ial.234 NCH3 H H CH3 CH3 Ial.235 NCH3 H H CH3 CH3 Ial.236 NCH3 H H CH3 CH3 Ial.237 NCH3 H H CH3 CH3 Ial.238 NCH3 H H CH3 CH Ial.239 NCH3 H H CH3 CH3 Ial.240 NCH H H CH3 CH3 Ial.241 NCH3 CH3 CH3 CH3 H Ial.242 NCH3 CH3 CH3 CH3 H Ial.243 NCH3 CH3 CH3 CH3 H Ial.244 NCH3 CH3 CH3 CH3 H Ial.245 NCH3 CH3 CH3 CH3 H Ial.246 NCH3 CH3 CH3 CH3 H Ial.247 NCH3 CH3 CH3 CH3 H Ial.248 NCH3 CH3 CH3 CH3 H Ial.249 NCH3 CH3 CH3 CH3 H Ial.250 NCH3 CH3 CH3 CH3 H Ial.251 NCH3 CH3 CH3 CH3 H Ial.252 NCH3 CH3 CH3 CH H Ial.253 NCH3 CH3 CH3 CH3 H Ial.254 NCH3 CH3 CH3 CH3 H Ial.255 NCH3 CH3 CH3 CH3 H Ial.256 NCH3 CH3 H CH3 CH3 Ial.257 NCH3 CH3 H CH3 CH3 Ial.258 NCH3 CH3 H CH CH3 Ial.259 NCH3 CH3 H CH3 CH3 Ial.260 'NCH3 CH3 H CH3 CH3 Ial.261 NCH3 CH3 H CH CH3 Ial.262 NCH3 CH3 H CH3 CH3 Ial.263 NCH3 CH3 H CH3 CH3 Ial.264 NCH3 CH3 H CH3 CH3 Ial.265 NCH3 CH3 H CH3 CH3 Ial.266 NCH3 CH3 H CH3 CH3 Ial.267 NCH3 CH3 H CH3 CH3 Ial.268 NCH3 CH3 H CH3 CH3 Ial.269 NCH3 CH3 H CH3 CH3 Ial.270 NCH3 CH3 H CH3 CH3 Ial.271 NCH3 CH3 CH3 CH3 CH3 Ial.272 NCH3 CH3 CH3 CH3 CH3 Ial.273 NCH3 CH3 CH3 CH3 CH3 Ial.274 NCH3 CH3 CH3 CH3 CH3 Ial.275 NCH3 CH3 CH3 CH3 CH3 Ial.276 NCH3 CH3 CH3 CH3 CH3 Ial.277 NCH3 CH3 CH3 CH3 CH3 Ial.278 NCH5 CH3 CH CH3 CH3 Ial.279 NCH3 CH3 CH3 CH3 CH3 Ial.280 NCH3 CH3 CH3 CH3 CH3 Ial.281 NCH3 CH3 CH CH3 CH3 Ial.282 NCH3 CH3 CH3 CH3 CH3 Ial.283 NCH3 CH3 CH3 CH3 CH3 Ial.284 NCH3 CH3 CH3 CH3 CH3 Ial.285 NCH3 CH3 CH3 CH3 CH3 Ial.286 NCH3 CH2C1 H H H Ial.287 NCH3 CH2C1 H H H Ial.288 NCH3 CH2C1 H H H Ial.289 NCH3 CH2C1 H H H Ial.290 NCH3 CH2C1 H H H Ial.291 NCH3 CH2C1 H H H Ial.292 NCH3 CH2C1 H H H Ial.293 NCH3 CH2C1 H H H Ial.294 NCH3 CH2C1 H H H Ial.295 NCH3 CH2C1 H H H Ial.296 NCH3 CH2C1 H H H Ial.297 NCH3 CH2C1 H H H Ial.298 NCH3 CH2C1 H H H Ial.299 NCH3 CH2C1 H H H Ial.300 NCH3 CH2C1 H H H No. R6 R7 Ial.l SCH3 OH Ial.2 SCH2CH3 OH Ial.3 S02CH3 OH Ial.4 SO_CH3CH 3 OH Ial.5 S02CH (CH3) 2 OH Ial.6 S02 (CH2) 2CH3 OH Ial.7 Cl OH Ial. 8 Br OH Ial.9 N02 OH Ial.10 CHF2 OH Ial.ll CF3 OH Ial.12 OCH3 OH Ial.13 OCH2CH3 OH Ial.14 OCHF; OH Ial.15 OCF3 OH Ial.16 SCH3 OH Ial.17 SCH2CH3 OH Ial.18 S02CH3 OH Ial.19 S02CH2CH3 OH Ial.20 S02CH (CH3) 2 OH Ial.21 S02 (CH2) 2CH3 OH Ial.22 Cl OH Ial.23 Br OH Ial.24 N02 OH Ial.25 CHF2 OH Ial.26 CF3 OH Ial.27 OCH3 OH Ial.28 OCH2CH3 OH Ial.29 OCHF; OH Ial.30 OCF3 OH Ial.31 SCH3 OH Ial.32 SCH; CH3 OH IaL.33 S? 2CH3 OH Ial.34 S02CH2CH3 OH Ial.35 S02CH (CH3) 2 OH Ial.36 S02 (CH £) _. CH OH Ial.37 Cl OH Ial.38 Br OH Ial.39 NO: OH Ial.40 CHF; OH Ial.41 CF3 OH Ial.42 OCH3 OH Ial.43 OCH2CH3 OH Ial.44 OCHF2 OH Ial.45 OCF3 OH lal.46 SCH3 OH Ial.47 SCH2CH3 OH Ial.48 S02CH3 OH Ial.49 S02CH2CH3 OH Ial.50 S02CH (CH3) 2 OH Ial.51 S02 (CH2) _CH3 OH Ial.52 Cl OH Ial.53 Br OH Ial.54 N02 OH Ial.55 CHF2 OH Ial.56 CF3 OH Ial.57 0CH3 OH Ial.58 OCH2CH3 OH Ial.59 OCHF2 OH Ial.60 OCF3 OH Ial.61 SCH3 OH Ial.62 SCH2CH3 OH Ial.63 S02CH3 OH Ial.64 S0: CH2CH3 OH Ial.65 S02CH (CH3) 2 OH Ial.66 S02 (CH2) 2CH3 OH Ial.67 Cl OH Ial.68 Br OH Ial.69 N02 OH lal.70 CHF2 OH Ial.71 CF3 OH Ial.72 OCH3 OH Ial.73 OCH2CH3 OH Ial.74 OCHF2 OH Ial.75 OCF3 OH Ial.76 SCH3 OH Ial.77 SCH2CH3 OH Ial.78 S02CH3 OH Ial.79 SO2CH2CH3 OH Ial.80 S02CH (CH3) 2 OH Ial.81 S02 (CH2) 2CH3 OH Iai.82 Cl OH Ial.83 Br OH Ial.84 N02 OH Ial.85 CHF2 OH Ial.86 CF3 OH Ial.87 OCH3 OH Ial.88 OCH2CH3 OH Ial.90 OCF3 OH Ial.91 SCH3 OH Ial.92 SCH2CH3 OH lal.93 SO2CH3 OH Ial.94 SO2CH2CH3 OH Ial.95 S02CH (CH3) 2 OH Ial.96 S02 (CH2) 2CH3 OH Ial.97 Cl OH Ial.98 Br OH Ial.99 N02 OH Ial.100 CHF2 OH Ial.101 CF3 OH Ial.102 OCH3 OH Ial.103 OCH2CH3 OH Ial.104 OCHF2 OH Ial.105 OCF3 OH Ial.106 SCH3 OH Ial.107 SCH2CH3 OH Ial.108 S02CH3 OH Ial.109 S02CH2CH3 OH Ial.110 S02CH (CH3) 2 OH Ial.lll S02 (CH2) 2CH3 OH Ial.112 Cl OH Ial.113 Br OH Ial.114 N0 OH Ial.115 CHF2 OH Ial.116 CF3 OH Ial.117 OCH3 OH Ial.118 OCH2CH3 OH Ial.119 OCHF2 OH Ial.120 OCF3 OH Ial.121 SCH3 OH Ial.122 SCH2CH3 OH Ial.123 SO2CH3 OH Ial.124 S02CH2CH3 OH Ial.125 S02CH (CH3) 2 OH Ial.126 S02 (CH;); CH3 OH Ial.127 Cl OH Ial.128 Br OH Ial.129 N02 OH Ial.130 CHF2 OH Ial.131 CF3 OH Ial.132 OCH3 OH Ial.133 OCH2CH3 OH Ial.134 OCHF2 OH Ial.135 OCF3 OH Ial.136 SCH3 OH Ial.137 SCH2CH3 OH Ial.138 S02CH3 OH Ial.139 S02CH2CH3 OH Ial.140 S02CH (CH3) 2 OH Ial.141 S? 2 (CH2): CH3 OH Ial.142 Cl OH Ial.143 Br OH Ial.144 N02 OH Ial.145 CHF OH Ial.146 CF3 OH Ial.147 OCH3 OH Ial.148 OCH2CH3 OH Ial.149 OCHF2 OH Ial.150 OCF3 OH Ial.151 SCH3 OH Ial.152 SCH2CH3 OH Ial.154 S? 2CH2CH3 OH Ial.155 S02CH (CH3) £ OH Ial.156 S02 (CH2) 2CH3 OH Ial.157 Cl OH Ial.158 Br OH Ial.160 CHF2 OH Ial.161 CF3 OH Ial.162 OCH3 OH Ial.163 OCH2CH3 OH Ial.164 OCHF2 OH Ial.165 OCF3 OH Ial.166 SCH3 OH Ial.167 SCH2CH3 OH Ial.168 SO2CH3 OH Ial.169 S02CH2CH3 OH Ial.170 S02CH (CH3) 2 OH Ial.171 S02 (CH2) 2CH3 OH Ial.172 Cl OH Ial.173 Br OH Ial.174 N02 OH Ial.175 CHF2 OH Ial.176 CF3 OH Ial.177 OCH3 OH Ial.178 OCH2CH3 OH Ial.179 OCHF2 OH Ial.180 OCF3 OH Ial.181 SCH3 OH Ial.182 SCH2CH3 OH Ial.183 S02CH3 OH Ial.184 S02CH2CH3 OH Ial.185 S0 CH (CH3) 2- OH Ial.186 S02 (CH2) 2CH3 OH Ial.187 Cl OH Ial.188 Br OH Ial.189 N02 OH Ial.190 CHF OH Ial.191 CF3 OH Ial.192 OCH3 OH lal.193 OCH2CH3 OH Ial.194 OCHF2 OH Ial.195 OCF3 OH Ial.196 SCH3 OH Ial.197 SCH2CH3 OH Ial.198 S02CH3 OH Ial.199 S02CH2CH3 OH Ial.200 S02CH (CH3) 2 OH Ial.201 S02 (CH2) 2CH3 OH Ial.202 Cl OH Ial.203 Br OH Ial.204 NO2 OH Ial.205 CHF2 OH Ial.206 CF3 OH Ial.207 OCH3 OH Ial.208 OCH2CH3 OH Ial.209 OCHF2 OH Ial.210 OCF3 OH Ial.211 - SCH3 OH Ial.212 * SCH2CH3 OH Ial.213 S02CH3 OH Ial.214 SO2CH2CH3 OH Ial.215 S02CH (CH3) 2 OH Ial.216 S02 (CH2) 2CH3 OH Ial.217 Cl OH Ial.218 Br OH Ial.219 N02 OH Ial.220 CHF2 OH Ial.221 CF3 OH Ial.222 OCH3 OH Ial.223 OCH2CH3 OH Ial.224 OCHF2 OH Ial.225 OCF3 OH Ial.226 SCH3 OH Ial.227 SCH2CH3 OH Ial.228 SO2CH3 OH Ial.229 S02CH2CH3 OH Ial.230 S02CH (CH3) 2 OH Ial.231 S02 (CH2)? CH3 OH Ial.232 Cl OH Ial.233 Br OH lal.234 N02 OH Ial.235 CHF2 OH Ial.236 CF3 OH Ial.237 OCH3 OH Ial.238 OCH2CH3 OH Ial.239 OCHF2 OH Ial.240 OCF3 OH Ial.241 SCH3 OH Ial.242 SCH2CH3 OH Ial.244 S02CH CH3 OH Ial.245 S02CH (CH3) 2 OH Ial.246 S02 (CH2) 2CH3 OH Ial.247 Cl OH Ial.248 Br OH Ial.249 N02 OH Ial.250 CHF2 OH Ial.251 CF3 OH Ial.252 OCH3 OH Ial.253 OCH2CH3 OH Ial.254 OCHF: OH Ial.255 OCF3 OH Ial.256 SCH3 OH Ial.257 'SCH2CH3 OH Ial.258 S02CH3 OH Ial.259 S02CH2CH3 OH Ial.260 S02CH (CH3) 2 OH Ial.261 S02 (CH2) 2CH3 OH Ial.262 Cl OH Ial.263 Br OH Ial.264 NO £ OH Ial.265 CHF2 OH Ial.266 CF3 OH HO z (eHO) HD3OS 062'T ^ I HO -HOeHO "OS 682't ^ I HO eHD3OS 882 * 1 ^ 1 HO eHD3HOS /.83'TIII HO eHDS 983 * 1 ^ 1 QZ HO e¿00 S82''t «? HO? _3HDO ^ QZ'l ^ l HO eHOeHOO esz't ^ i HO e_30 tsz't ^ i ?? HO 3_3HD 082 * 1 ^ 1 HO 3ON ßLZ'l ^ I HO ag QLZ't ^ t HO to LLZ'l ^ l HO eH0: (3H3) 0S 9LZ'l ^ l OT HO ~ (-H0) HD3OS SLZ'l ^ I HO f eH03H03OS LZ'l ^ l HO eHD2OS ZLZ-t ^ t HO eHOzHOS ZLZ'1 ^ HO eHOS XLZ'XV HO e_IDO O? S'I ^ I HO 3_3HOO 692 * 1 ^ 1 HO eHOO L9Z'l ^ I 8fr Ial.292 Cl OH Ial.293 Br OH Ial.294 NO: OH Ial.295 CHF: OH Ial.296 CF3 OH Ial.297 OCHO OH 298 OCK: CH3 OH Ial.299 OCHF2 OH Ial.300 OCF3 OH Extraordinary preference is also given to the compounds of formula Ia2, particularly to compounds Ia2.1 to Ia2.300, which differ from the corresponding compounds Ial.300 because R "is methyl.

The compounds of the formula Ia3, particularly the compounds Ia3.1 to Ia3.300, which differ from the compounds lal.l to Ial.300 in which R8 is ethyl, are also particularly preferred.

The compounds of formula Ia4, particularly compounds Ia4.1 to Ia4,300, which differ from compounds Ial.l to Ial.300 in which R * is ethyl and 11 is methyl, are also preferred in an extraordinary manner.

The compounds of the formula Ia5, particularly the compounds Ia5.1 to Ia5,300, which differ from the compounds Ial.l to Ial.300 in which R8 is 1-methyl-l-ethyl, are also particularly preferred.

CH3 The compounds of the formula Ia6, particularly the compounds Ia6.1 to Ia6.300, which differ from the compounds Ial.3la in which R8 is 1-methyl-l-ethyl and R11 is also preferred in an extraordinary manner are also preferred. methyl.

The compounds of the formula Ia7, particularly the compounds Ia7.1 to Ia7.300, which differ from the compounds Ial.l to Ial.300 in which R,? O is methyl, are also preferred in an extraordinary manner.

The compounds of the formula Ia8, in particular the compounds Iad.l to Iad.300, which differ from the compounds Ial.l to Ial.300 in which R10 is methyl and R11 is methyl, are also particularly preferred.

The compounds of the formula Ia9, particularly the compounds Ia9.1 to Ia9.30G, which differ from the compounds Ial.l to Ial.300 in which R "and R9 are 1-methyl-l-ethyl, are also particularly preferred. .

H3C CH3 Compounds of the formula IalO, particularly compounds IalO.la IalO.300, which differ from Ial.300 compounds in which R "and R9 are 1-methyl-1-ethyl are also extremely preferred. and R ~~ is methyl.

H3C CH3 Compounds of the formula Iall, particularly compounds Iall.l to Iall.300, which differ from compounds Ial.l to Ial.300 in which R8 is ethyl and R "'is methyl, are also extremely preferred.

H3C CH2CH3 CH3 The compounds of formula Ial2, particularly compounds Ial2.1 to Ial2.300, which differ from the corresponding compounds Ial.l to Ial.300 in which R8 is ethyl and R ?: and R11 are methyl, are also particularly preferred.

The compounds of the formula Ial3, particularly the compounds Ial3.1 to I3.300, which differ from the compounds Ial.1 to I.300 in which R1 is methoxy, are also particularly preferred.

Also extremely preferred are compounds of the formula Ial4, particularly the compounds Ial4.1 to Ial4.300, which differ from the corresponding compounds Ial.l to Ial.300 in that? .- is methoxy and R11 is methyl.

The compounds of the formula Ial5, particularly the compounds Ial5, are also particularly preferred. 1 to Ial 5. 300, which differ from the compounds Ial. l to Ial. 300 wherein R1 is methoxy and R8 is ethyl.

The compounds of the formula Ial6, particularly the compounds Ial6.1 to I 16.300, which differ from the compounds Ial.l to Ial.300 in which R1 is methoxy, R8 is ethyl and R11 is methyl, are also particularly preferred.

The compounds of the formula Ial7, particularly the compounds Ial7.ia I7.700, which differ from the compounds Ial.1 to I.300 in which R1 is methoxy and Re is 1-methyl-1-ethyl, are also particularly preferred. .

The compounds of the formula Ial8, particularly the Iald compounds, are also particularly preferred. l to Ial 8. 300, which differ from the compounds Ial. l to Ial. Wherein R1 is methoxy, R8 is 1-me il-l-ethyl and R11 is methyl.

CH3 The compounds of the formula Ial9, particularly the compounds Ial9.1 to Ial9.300, which differ from the compounds Ial.l to Ial.300 in which R "is methoxy and R10 is methyl, are also particularly preferred.

The compounds of the formula Ia20, particularly the compounds Ia20.1 to Ia20.300, which differ from the compounds Ial.3la in which R1 is methoxy, R1"is methyl and R ~~ is also exceptionally preferred. methyl.

The compounds of formula Ia21, particularly compounds Ia21, are also particularly preferred. 1 to Ia21. 3 '_. 0, which differ from the compounds Ial. I to .300 where R "is methoxy and R8 and R9 are 1-methyl-l-ethyl.

H3C CH3 The compounds of the formula Ia22, particularly the compounds Ia22.ia Ia22.2_0, which differ from the compounds Ial.la.al.30C in which R "is methoxy, R8 and R9 are 1-methyl, are also extremely preferred. -l-ethyl and Ru is methyl.

H3C CH! The compounds of the formula Ia23, particularly the compounds Ia23.1 to Ia23.3I0, which differ from the compounds Ial.la.al.30C in which R "is methoxy, R8 is ethyl and" "is methyl, are also extremely preferred. .

The compounds of the formula Ia24, particularly the compounds Ia24.1 to Ia24,300, which differ from the compounds Ial.la.I.al.3, are also particularly preferred: wherein?. "Is methoxy, R8 is ethyl and R" and R11 are methyl.

The 3- (heterocycidyl) benzoylpyrazole derivatives of the formula I can be obtained by several routes, for example, by the following processes. Process A: Reaction of pyrazoles of the formula II with an activated benzoic acid Illa or an activated benzoic acid Illß, preferably activated in situ, to provide the corresponding acylation product IV, followed by rearrelation, which allows obtaining the compounds of the formula I where R7 = OH.

I wherein R7 = OH L1 is a nucleophilically replaceable leaving group such as, for example, halogen, for example bromine, chlorine, hetaryl such as, for example, imidazolyl, pyridyl, carboxylate, for example acetate, trifluoroacetate, etc. The activated benzoic acid can be used directly, as for example in the case of benzoyl halides, or can be generated in situ, for example, using dicyclohexylcarbodiimide, triphenylphosphine / azodicarboxylic ester, 2-pyridine disulfide / triphenylphosphine, carbonyldiimidazole, etc. . It may be advantageous to effect the acylation reaction in the presence of a base. The reagents and the auxiliary base are used profitably in equimolar amounts here. A slight excess of auxiliary base, for example, from 1.2 to 1.5 molar equivalents, based on II, may be of benefit in some cases. Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Suitable for use as solvents are, for example, chlorinated hydrocarbons such as, for example, methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons such as toluene, xylene, chlorobenzene, ethers such as, for example, diethyl ether, methyltert-butyl ether, dimethoxyethane, tetrahydrofuran. , dioxane, polar aprotic solvents such as for example acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters such as for example ethyl acetate, or mixtures thereof. If the activated carboxylic acid component employing benzoyl halide, it may be advantageous to cool the reaction mixture to a temperature of 0 to 10 ° C when this reaction partner is added. The mixture is subsequently stirred at a temperature of 20-100 ° C, preferably at 25-50 ° C, until the completion of the reaction. The treatment is carried out in conventional manner, for example, by emptying the reaction mixture in water and extracting the valuable product. Solvents particularly suitable for this purpose are methylene chloride, diethyl ether, dimethoxyethane and ethyl acetate. The organic phase is dried and the solvent is removed, after which the crude ester can be used for rearrangement without further purification. The rearrangement of the esters to provide the compounds of the formula I is advantageously effected at a temperature of 20-40 ° C in a solvent and in the presence of a base and, if appropriate, using a cyano compound as a catalyst. Suitable solvents are, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, dimethoxyethane, toluene or mixtures thereof. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines such as for example triethylamine or pyridine, or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably used in an equimolar amount or up to an excess of four times, based on in the ester. Preference is given to the use of triethylamine or alkali metal carbonates, preferably twice the equimolar amount, based on the ester. Suitable cyano compounds are inorganic cyanides such as sodium cyanide and potassium cyanide, and cyano organic compounds, such as acetonanohydrin and trimethylsilyl cyanide. They are used in an amount of 1 to 50 mol%, based on the ester. Preference is given to the use of acetonanohydrin or trimethylsilyl cyanide, for example, in an amount of 5 to 15, preferably 10 mol%, based on the ester. The treatment can be carried out in a manner known per se. The reaction mixture, for example, is acidified with dilute mineral acid such as for example 5% hydrochloric acid or sulfuric acid, and extracted with organic solvent, for example, methylene chloride or ethyl acetate. The organic extract can be extracted by a 5-10% alkali metal carbonate solution, for example, a solution of sodium carbonate or potassium carbonate. The aqueous phase is acidified and the resulting precipitate is removed by filtration with suction and / or extracted with methylene chloride or ethyl acetate, and the mixture is dried and concentrated. (Examples for the preparation of hydroxypyrazole esters and for the rearrangement of the esters are provided, for example, in EP-A 282 944 and US 4 643 757). However, it is also possible to generate the "acylation product" IV in situ by reacting a pyrazole of the formula II, or an alkali metal salt thereof, with a 3- (heterocyclyl) benzene derivative of the formula V in the presence of carbon monoxide, a catalyst and a base.

II CO [catalyst] L is a leaving group such as, for example, halogen, for example chlorine, bromine or iodine, or sulfonate, such as, for example, mesylate or triflate; preferably bromine or triflate. The "acylation product" IV reacts, directly or indirectly, to provide the 3- (heterocyclyl) benzoylpyrazole derivative of the formula I. Suitable catalysts are palladium-ligand complexes wherein the palladium is present in the oxidation state 0, palladium metal that has been optionally absorbed in a vehicle, and preferably palladium salts (II). The reaction with palladium (II) salts and metallic palladium is preferably carried out in the presence of complex ligands. An example of a palladium (0) -proper ligand complex is tetrakis (triphenylphosphine) palladium. The metal palladium is preferably absorbed in an inert carrier such as, for example, activated carbon, silica, alumina, barium sulfate or calcium carbonate. The reaction is preferably carried out in the presence of complex ligands such as for example triphenylphosphine. Examples of suitable palladium (II) salts are palladium acetate and palladium chloride. The presence of complex ligands such as for example triphenylphosphine is preferred. Suitable complex ligands for palladium-ligand complexes or in which presence the reaction is preferably carried out with palladium metal or palladium salt (I I), are phosphines whose structure is represented by the following formulas: wherein z is from 1 to 4 and the radicals Ra to Rg are alkyl Z_- C6, cycloalkyl C3-C6, arylalkyl C? ~ C2, or, preferably, aryl. For example, aryl is naphthyl and fer. the unsubstituted or substituted with or for example 2-tolyl and, particularly, unsubstituted phenyl. The complex palladium salts can be prepared in a manner known per se starting from commercially available palladium salts with, for example, palladium chloride or palladium acetate and the appropriate phosphines such as, for example, triphenylphosphine or 1,2-bis (diphenylphosphino). Ethane Many of the palladium salts that form complexes are also commercially available. Preferred palladium salts are [(R) (+) 2,2'-bis (diphenylphosphino) -1,1 '-bubfthyl chloride. -palladium (II), bis (triphenylphosphine) palladium (II) acetate and, particularly, bis (triphenylphosphine) palladium (II) chloride. The palladium catalyst is usually used in a concentration of 0.05 to 5 mol%, and preferably from 1 to 3 mol% Suitable bases are tertiary amines such as N-methylpiperidine, ethyldiisopropylamine, 1,8-bisdimethylaminonaphthalene or, particularly, triethylamine Alkali metal carbonates are also suitable, such as, for example, sodium carbonate or potassium carbonate. However, mixtures of potassium carbonate and triethylamine are also suitable.In general, 2 to 4 molar equivalents, particularly 2 molar equivalents, of alkali metal carbonate and 1 to 4 molar equivalents, particularly 2 molar equivalents, are employed, of the tertiary amine, based on the 3- (heterocyclyl) -benzene derivatives of the formula V. Suitable solvents are nitriles such as, for example, benzonitrile and acetonitrile, amides, For example, dimethylformamide, dimethylacetamide, tetraalkyl C? -C4-ureas, or N-methylpyrrolidone and, preferably, ethers such as tetrahydrofuran and methyltert-butyl ethers. Particularly preferred are ethers such as for example 1,4-dioxane and dimethoxyethane. Process B: Compounds of the formula I wherein R7 is different from hydroxyl are obtained by the reaction of compounds of the formula I wherein R7 = hydroxyl with alkylating agents, sulfonylating agents or acylating agents L3-R7a (VI) . where R7 = OH VI I where R ^ = OR7a (= R7 different from OH) LJ is a nucleophically replaceable leaving group such as for example halogen such as, for example, bromine or chlorine, acyloxy, for example, acetyloxy or ethylcarbonyloxy, or alkylsulfonyloxy, for example, methylsulfonyloxy or trifluoromethylsulfonyloxy. R 'a is C 1 -C 0 alkyl, C 3 -C 6 alkenyl, C 1 -C 6 alkylsulfony, C 1 -C 6 alkylcarbonyl. (alkylthio) C.-C ^ -carbonyl, f-phenylsulfonyl or phenylcarbonyl, wherein the phenyl radical of the two aforementioned agents may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, C_-C-alkyl / C-C4-haloalkyl, C-C4-alkoxy or C-C4-haloalkoxy.

The compounds of formula VI can be used directly, for example, in the case of sulphonyl halides or sulphonic anhydrides, or can be generated in situ, for example, activated sulfonic acids (using sulfonic acid and dicyclohexylcarbonyldiimide, carbonyldiimidazole, etc. .). The initial materials are generally used in equimolar quantities. However, it can also be advantageous to use an excess of one or the other component. If appropriate, it may be helpful to effect the reaction in the presence of a base. The reagents and the auxiliary base are used profitably in equimolar amounts. An excess of auxiliary base, for example, from 1.5 to 3 molar equivalents, based on I, may be of benefit in certain cases. Suitable auxiliary bases are tertiary alkylamines, such as for example triethylamine, pyridine, alkali metal carbonates such as, for example, sodium carbonate or potassium carbonate, and alkali metal hydrides, for example sodium hydride. Preference is given to the use of triethylamine and pyridine. Suitable solvents are, for example, chlorinated hydrocarbons, such as for example methylene chloride and 1,2-dichloroethane, aromatic hydrocarbons such as for example toluene, xylene, chlorobenzene, ethers, such as for example diethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane, solvents polar aprotic substances, such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters, for example ethyl acetate or a mixture thereof. In general, the temperature of the reaction is within a range of 0 ° C to the boiling point of the reaction mixture. The treatment can be carried out in a manner known per se to provide the product. The pyrazoles of formula II used as starting materials are known or can be prepared by the process known per se (for example EP-A 240 001 and J. Fra t.Chem. 315, 383 (1973)). The activated benzoic acids Illa can be obtained in a manner known per se from the benzoic acids Illß. The latter, on the other hand, are obtained by hydrolysis from the corresponding esters VII. They can be prepared by converting an oxime or hydrazone of the formula VIII into the corresponding hydroxamic acid halide, particularly hydroxamic acid chloride or carbohydrazide halide, particularly carbohydrazide chloride; generating a nitromyl oxide or nitrile imine in situ and reacting this with an alkene (see, for example, Chem. Ber 106, 3258-3274 (1973)).

VII VIII Hydrolysis mß L "denotes an alkoxy radical Ci-Ce. Without bengo, the benzoic acids III3 can also be obtained by converting an oxime or hydrazine of the formula IX into the corresponding r.itril oxides and reacting them with alkenes to provide the corresponding cycloaddition products (see, for example, Chem. Ber. 106, 3258-3274, 1973).) Therefore, for example, the oxime of formula IX (X = 0) is oxidized with sodium hypochlorite and It is reacted with a suitable alkene in an inert solvent such as for example methylene chloride, chloroform, tetrahydrofuran, dioxane or acetonitrile.The product is then converted in the presence of catalyst and a base in the benzoic acid III.sub.5 using carbon monoxide and water.

IX CC, H20? [catalyst] Illß L2 refers to a leaving group, such as, for example, halogen, for example chlorine, bream or iodine, or sulfonate, such as, for example, mesylate or triflate, preferably bromine c-triflate.

With regard to the carbonylation reaction, what has been said above is applied analogously. Preparation Examples 4- [2-chloro-3- (4,5-dihydrcisoxazol-3-yl) -4-methylsulfonylbenzyl] -5-hydroxy-1- (1,1-dimethyl-1-ethyl) -1H-pyrazole (Compound 2.1) 2.32 g (0.02 mol) of 1- (1,1-dimethyl-1-ethyl) -5-hydroxy-1H-pyrazole and 2.3 g (0.02 mol) of potassium carbonate were added to a solution of 5.4 g (0.02 mol) of 2-chloro-3- (4,5-dihydroisoxazil-3-yl) -4-methylsulfonylbenzoic acid chloride in 100 ml of ethylene glycol methyl ethyl ether, and the mixture was stirred overnight. The mixture was subsequently refluxed for 3 hours, the solvent was removed by distillation, the residue was taken up in 3 OD of water and washed with methylene chloride, and the aqueous phase was acidified to pH = 3 using 10% hydrochloric acid. %. The precipitate was removed by filtration cor. Suction and drying at 40 ° C. This yielded 4.6 g (65% theoretical level) of 4- [2-chloro-3- (4,5-dihydroisoxazol-3-yl) -4-methylsulfonylbenzeyl] -5-hydroxy- l- (1,1-dimethyl-l-ethyl) -1H-pyrazole] In addition to the above compound, Table 2 presents a list of other benzoylpyrazoles substituted by 3- (heterocyclyl) of the formula I which were prepared c well that can be Prepare similarly.

OR Table 2: No. R1 R2 R3 R4 R5 R6 R7 2.1 Cl HHHH S02CH3 OH 2.2 Cl HHHH SO: CH3 OH 2.3 Cl HHHH S02CH3 OCH (CH3) 2 2.4 Cl HHHH S02CH3 OCH2CH3 2.5 Cl HHHH S02CH3 QCH3 2.6 Cl HHHH S02CH3 OC [3 -F-C6H4] 2. 7 Cl H H H H S02CH 3 OCOC 6 H 5 2.8 Cl H H H H SO SO; CH 3 OCO [3, 5-F 2 -C 6 H 3] 2. 9 Cl H H H SO SO: CH 3 OH 2.10 Cl H H H H S02CH 3 OCH (CH 3) 2 2.11 Cl H H H H SO SO; CH 3 OCOC 5 H 5 2.12 Cl H H H H S02CH 3 OCO (3-F-C6H4) 2. OCH3 H H H H S02CH3 OH 2.14 OCH3 H H S02CH3 OCOSCH3 2.15 Cl H H H S02CH3 OH 2.16 Cl H H H SO; CH 3 OCH 3 2.17 Cl H H H S02CH 3 OCH 2 H 5 2.18 OCH 3 H H H H S0 2 CH 3 OCO [3-F-C 6 H 4] No. R8 R9 R10 R11 Physical data p.f. [° ^ -NMR [d in ppm] 2. 1 CH3 CH3 CH3 H 198-200 2.2 CH3 CH3 HH 210-215 2.3 CH3 CH3 HH 175-180 2.4 CH3 CH3 HH 150-155 2.5 CH3 CH3 HH 185-190 2.6 CH3 CH3 HH 225-230 2.7 CH3 CH3 HH 220-225 2.8 CH3 CH3 HH 220-225 2.9 CH (CH3) 2 CH3 HH 150-155 2.10 CH (CH?); CH3 H H 125-130 2.11 CH (CH3) CH3 H H 135-140 2.12 CH (CH3)? CH 3 H H 130-135 2.13 CH 3 CH 3 H H 154-156 2.14 CH 3 CH 3 H H oil 2.15 CH (CH 3) 2 CH (CH 3) 2 H H 200-205 2.16 CH (CH 3); CH (CH3); HH 65-70 2.17 CH (CH3) 2 CH (CH3) 2 HH oil 2.18 CH3 CH3 HH 78-79 The 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I and their salts useful in agriculture are suitable, both in the form of mixtures of isomers, such as in the form of pure isomers, as herbicides. The herbicidal compositions comprising compounds of the formula I control the vegetation in areas where there are no crop plants very efficiently, especially at high application rates. They act against weeds and damaging grass in crops, for example wheat, rice, corn, soybeans and cotton without causing significant damage to the harvest plants. This effect is observed mainly in low application regimes. According to the method of application employed, the compounds I, or the compositions comprising them, can be additionally used in a further number of harvest plants to eliminate undesirable plants. Examples of suitable crops are the following: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. Silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus lemon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreu, Gossypium herbaceu, Gossypium vitifolium), Helianthus annuss, Hevea Brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris , Linu usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum , Prunus avium, Prunus pérsica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Sécale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays. In addition, the compounds I can also be used in crops that tolerate the action of herbicides due to selection, including genetic engineering methods. The compounds I, or the herbicidal compositions comprising them, can be used, for example, in the form of aqueous solutions ready for spraying, powders, suspensions, also aqueous, oily or other highly concentrated suspensions or dispersions, emulsions, dispersions in oil. , pastes, powders, materials for broadcast application, or granules, by means of spraying, atomization, spraying, broadcasting or irrigation. The forms of use depend on the intended purposes; in any case, they must guarantee a very fine distribution of the active compounds according to the invention. The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries which are commonly used for the formulation of crop protection agents. Essentially, suitable inert auxiliaries include: medium to high boiling mineral oil fractions, such as, for example, kerosene and diesel oil, in addition to coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example , paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents, for example amines, for example N-methylpyrrolidone and water. Aqueous forms of use can be prepared from emulsion concentrates, suspensions, pastes, wettable pellets or granules which can be dispersed in water, by the addition of water. To prepare the emulsions, pastes or dispersions in oil, the substances, either co-or as dissolved in an oil or solvent, can be homogenized in water through a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates comprising an active compound, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water., Suitable surfactants (adjuvants) are the salts of alkali metals, salts of alkaline earth metals and ammonium salts of aromatic sulfonic acids, for example, ligno-, phenol-, naphthalene- and dibutylnaphlenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether and sulfates of fatty alcohols and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ether, sulfated naphthalene condensates and their derivatives with formaldehyde, condensates of naphthalene, or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylenectylphenol ether, isooctyl-, octyl- or nonylphenol ethoxylated, alkylphenyl or tributylphenyl, polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol / ethylene oxide condensate, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulfite waste liquors or methyl cellulose. Powders, materials for broadcasting can be prepared by mixing or milling the active compounds together with a solid carrier. Granules, for example, coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds with solid carriers. Solid vehicles are mineral earths, such as silicas, silicate gels, silicates, talc, kaolin, limestone, lime, chalk, fine clay soil, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, rust of magnesium, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate and ammonium nitrate, ureas and products of vegetable origin, such as cereal powder, tree bark powder, wood dust and peel powder. nut, cellulose powder, or other solid vehicles. The concentrations of compounds I in the ready-to-use preparations can vary within wide ranges. In general, the formulations comprise from about 0.001 to 98% by weight, preferably from 0.01 to 95% by weight of at least one active compound. The active compounds are used in a purity of 90% to 100%, preferably from 95 to 100% (in accordance with the NMR spectrum). The following formulation examples illustrate the preparation of such formulations: I. 20 parts by weight of compound No. 2.2 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. The solution is emptied into 100, 000 parts by weight of water and said solution is finally distributed to provide an aqueous dispersion comprising 0.02% by weight of the active compound. II. 20 parts by weight of compound No. 2.8 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctylphenol and 10 parts by weight the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By emptying the solution in 100,000 parts by weight of water and distributing it finely therein, an aqueous dispersion comprising 0.02% by weight of the active compound is obtained. III. 20 parts by weight of the active compound No. 2.8 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point between 210 and 280 ° C and 10 parts by weight. Adduct weight of 40 moles of ethylene oxide to 1 mole of castor oil. By emptying the solution in 100,000 parts by weight of water and distributing it finely therein, an aqueous dispersion comprising 0.02% by weight of the active compound is obtained. IV. 20 parts by weight of the active compound No. 2.2 are completely mixed with 3 parts by weight of sodium diisobutyl naphthalenesulfonate, 17 parts by weight of the sodium salt of lignosulfonic acid from a residual sulphite liquor and 60 parts by weight of silica gel powder, and the mixture is ground in a hammer mill. The fine distribution of the mixture in 20,000 parts by weight of water provides a spray mixture comprising 0.12% by weight of the active compound. V. 3 parts by weight of active compound No. 2.8 are mixed with 97 parts by weight of finely divided kaolin. This provides a powder comprising 3% by weight of the active compound. SAW. 20 parts by weight of the active compound No. 2.2 are intimately mixed with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol / urea condensate / formaldehyde and 68 parts by weight of a paraffin mineral oil. This provides a stable oily dispersion. VII. 1 part by weight of active compound No. 2.8 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This provides a stable emulsion concentrate.

VIII.1 part by weight of active compound No. 2.2 is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of ettol® EM 31 (= nonionic emulsifier based on ethoxylated castor oil). This provides a stable emulsion concentrate. The compound of the formula I or the herbicidal compositions can be applied before the emergence of the plants or after the emergence of the plants. If the active compounds are less tolerated by certain crop plants, application techniques can be employed in which the herbicidal compositions are sprayed, with the help of the spray equipment, in such a way that they come into contact as little as possible, if at all. they come in contact with the leaves of sensitive crop plants, while the active compounds reach the leaves of the undesirable plants that grow below, or the bare surface of the soil (lateral application, backward application). The application regimes of the compound of the formula I are from 0.001 to 3.0, preferably from 0.01 to 1.0 kg / ha of active substance (s.a.), according to the control objective, the season, the target plants and the growth stage. To broaden the spectrum of activity and to achieve synergistic effects, the 3-heterocyclyl-substituted benzoylpyrazoles of the formula I can be mixed with a large number of representatives of other groups of active compounds that regulate growth or herbicides and then applied concomitantly . Suitable components for mixtures are, for example, 1, 2, 4-thiadiazoles, 1, 3, 4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anuides, (het) aryloxyalkanoic acids and their derivatives, benzoic acid and their derivatives, benzothiadiazinones, 2- (het) aroyl-1-, 3-cyclohexandiones, hetarylarilketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexeneone oxime ether derivatives, diazines, acid dichloropropionic and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3, 4, 5, 6- tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, 2-pyrimidylic ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils. It may also be advantageous to apply the compounds of the formula I, alone or concomitantly in combination with other herbicides, in the form of a mixture with other crop protection agents, for example, together with agents for controlling pests or fungi or bacteria phytopathogenic It is also interesting the ability to mix with solutions of mineral salts that are used for the treatment of deficiencies of nutrients and minor elements. Non-phytotoxic oils and oil concentrate can also be added. EXAMPLES OF USE The herbicidal activity of 3-heterocyclyl substituted benzoylpyrazoles of the formula I was demonstrated through the following greenhouse experiments: The culture vessels used were plastic pots containing loamy sand with approximately 3.0% humus as the substrate. The seeds of the test plants were seeded separately for each species. For the pre-emergence treatment of the seedlings, the active compounds, which had been suspended or emulsified in water, were applied directly after sowing through fine distribution nozzles. The containers were gently irrigated to promote germination and growth and subsequently covered with transparent plastic bells until the plants have taken root. This coating causes uniform germination of the test plants, unless they have been negatively affected by the active compounds. For the post-emergence treatment of the plants, the test plants were first grown to a height of 3 to 15 cm, according to the plant's habit, and only then treated with the active compounds that had been suspended or emulsified er_water. The test plants were, for this purpose, either directly sown and cultivated in the same containers, or were first cultivated separately as seedlings and transplanted into the test vessels a few days before treatment. The application regime for post-emergence treatment can be 0.25, 0.125 or 0.0625 kg s.a. (active substance) / ha. Depending on the species, the plants were kept at a temperature of 10-25 ° C or 20-35 ° C. The trial period lasted for 2 to 4 weeks. During this period the plants were taken care of and their response to the individual treatments was evaluated. The evaluation was carried out using a scale of 0 to 100. 100 means the absence of emergence of the plants, or the complete destruction of at least the aerial parts and 0 means absence of damage or normal evolution of growth.

The plants used in the greenhouse experiments were of the following species: Scientific name Common Name Chenopodium album ash Echinochloa cruz galli farm pasture Ipomoea ssp. wonder Polygonum persicaria persicario Setaria faberi giant fox tail Setaria eiridis green fox tail Sinapsis alba white mustard Solanum nigrum solano At application rates of 0.25 to 0.125 kg / ha, compound 2.2 (Table 2) showed a very good post-emergence action of seedlings against both harmful plants such as farm pasture and green foxtail and against ash, persicario and solano.In addition, compound 2.8 (Table 2) presented, under the above conditions, very good action against undesirable plants such as grass of farm, giant fox tail, marigold, white mustard and solano.

Claims (11)

1. CLAIMS 1.
2. A 3- (heterocyclyl) benzoylpyrazole derivative of the formula I wherein X is O, NH c or N (alkyl C.-Ce); R 1 is nitro, halogen, C 1 -C 4 alkoxy, C 1 -C haloalkoxy, C 4 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 4 -C 4 alkylsulfonyl, or C 1 -C 4 haloalkylsulfonyl; R 2, R 3, R 4, R 5 are hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; R6 is halogen, nitro, C_-C4 haloalkyl, C? -Calkoxy, C? -C4 haloalkoxy, C? -C4 alkylthio, C? -C4 haloalkylthio, C? -C4 alkylsulfonyl or C? -C4 haloalkylsulfonyl; R7 is hydrcxyl, C6-C6 alkoxy, C3-Ce alkynyloxy, Ci-C2 alkylsulfonyloxy, C-C2 alkylcarbonyloxy (alkylthio ".C.-C4-carbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned may ultimately be partially or totally halogenated and / or may carry one to three of the following groups: nitro, cyano, C? -C4 alkyl, C? -C4 haloalkyl, C? C4 or haloalkoxy C? -C; R8, R9 are C_-C4 alkyl; R 10 is hydrogen or C 1 -C 4 alkyl; where the number of carbon atoms of the radicals Rs, R9 and R "together is at most 7, Rlx is hydrogen or C: -C4 alkyl, and its salts useful in agriculture 2.
3. A 3- (heterocyclyl) benzoylpyrazole derivative of the formula I in accordance with Claim 1, wherein X is O, R 1 is nitro, halogen, C 1 -C-alkoxy or alkylthio-U 4, R 6 is C 1 -C 4 alkylthio or C 1 -C 4 -alkylsulfonyl 3.
4. A 3-derivative heterocyclyl) benzoylpyrazole of the formula I according to claim 1, wherein X is O; R1 is nitro, halogen, C4-C4 alkoxy or Ci-C alkylthio; R6 is halogen, nitro, C_-C haloalkyl, C-alkoxy ? ~ C4 or C1-C4 haloalkoxy.
5. A 3- (heterocyclyl) benzoylpyrazole derivative of the formula I according to claim 1, wherein X is N (C 1 -C 6 alkyl) • A process for the preparation of 3- (heterocyclyl) benzoylpyrazole derivatives In formula I, where R7 = hydroxy according to claim 1, which comprises the acylation of a pipelle of formula II with an activated Izo benzoic acid or an Illß activated benzoic acid, wherein the variables X, R1 to Rc and R8 to R11 are in accordance with that defined in claim 1 and L1 is a nucleophilically displaceable leaving group and rearregating the acylation product, in the presence or absence of a catalyst, to provide the compounds of the formula I wherein R7 = hydroxyl.
6. 6. A process for the preparation of 3- (heterocyclyl) enzoylpyrazole derivatives of the formula I, wherein R7 = OH according to claim 1, comprising the reaction of a pyrazole of the formula II wherein the variables R to R "are in accordance with that defined in claim 1, or an alkali metal salt thereof, with a 3- (heterocyclyl) benzene derivative of the formula V wherein the variables X and R1 to R6 are in accordance with that defined in claim 1 and L2 is a leaving group in the presence of carbon monoxide, a catalyst and a base.
7. A process for the preparation of 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I, wherein R7 is not hydroxyl according to claim 1, which comprises the reaction of a 3- (heterocyclyl) benzoylpyrazole derivative I where R7 = hydroxyl I where R7 = OH with a compound of formula VI L3-R7a VI wherein L3 is a nucleophilically replaceable leaving group; Ra is C?-C6 alkyl, C3-C al alkenyl, C?-C6 alkylsulfonyl, C?-C6 alkylcarbonyl, (Cilt-C 4 alkylkyloxy), phenylsulfonyl or phenylcarbonyl, wherein a phenyl radical of the two substituents mentioned above can be partially or totally halogenated and / or can carry one of three groups: nitro, cyano, C? -C4 alkyl, C? -C4 haloalkyl, C? -C4 alkoxy or C? -C4 haloalkoxy.
8. A composition, which comprises a herbicidally effective amount of at least one 3- (heterocyclyl) benzoylpyrazole derivative of the formula I or a salt useful in the agriculture of, in accordance with that claimed in any of claims 1 to 4, and auxiliaries usually employed for the formulation of agents for the protection of crops.
9. 9. A process for preparing compositions according to claim 8, comprising mixing a herbicidally effective amount of at least one 3- (heterocyclyl) benzoylpyrazole derivative of the formula I or a salt useful in the agriculture of I, as claimed in any of claims 1 to 4, and auxiliaries who are customarily employed to formulate crop protection agents.
10. 10. A method for controlling undesirable vegetation, comprising allowing a herbicidally effective amount of at least one 3- (heterocyclyl) benzoylpyrazole derivative of the formula I or a useful agricultural salt of I, according to what is claimed in any of claims 1 to 4 acts on the plants, their habitat and / or seeds.
11. 11. The use of the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I and / or their salts useful in agriculture, as claimed in any of claims 1 to 4, as herbicides. SUMMARY OF THE INVENTION 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I are described wherein X is O, NH or N-alkyl; R1 is nitro, halogen, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyl or haloalkylsulfonyl; R2, R3, R R ~ are hydrogen, alkyl or haloalkyl; R6 is halogen, nitro, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyl or haloalkylsulfonyl; R7 is hydroxyl, alkoxy, alkenyloxy, alkylsulfonyloxy, alkylcarbonyloxy, (alkylthio) carbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical may be substituted; R8, R9 are alkyl; Ri0 is hydrogen or alkyl; R 11 is hydrogen or alkyl; and their salts useful in agriculture, compounds for their preparation, and the use of these compounds or compositions comprising them to control undesirable plants.