Patent EA-002421-B1 (EA)
Title: Substituted 4-benzoyl-pyrazoles
Inventor: HILL REGINA LUISE
IPC: C07D231/24
Filed: 1997-12-19
Abstract: 1. A 4-benzoylpyrazole of the formula I and or an agriculturally useful salt thereof   where the substituents of the formula I have the following meanings: R<1>, R<2> are hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, -OR<5>, -OCOR<6>, -OSO2R<6>, -SH, -S(O)nR<7>, -SO2OR<5>, -SO2NR<5>R<8>, -NR<8>SO2R<6> or -NR<8>COR<6>; R<3> is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, -OR<7>, -SR<7> or -NR<7>R<10>; R<4> is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C4-C6-cycloalkenyl, C3-C6-alkynyl, -COR<9>, -CO2R<9>, -COSR<9> or -CONR<8>R<9>, it being possible for the abovementioned alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals and R<9> of the radicals -COR<9>, -CO2R<9>, -COSR<9> and -CONR<8>R<9> to be partially or fully halogenated and/or to have attached to them one to three of the following groups:hydroxyl, mercapto, amino, cyano, R<10>, -OR<10>, -SR<10>, -NR<8>R<10>, =NOR<10>, -OCOR<10>, -SCOR<10>, -NR<8>COR<10>, -CO2R<10>, -COSR<10>, -CONR<8>R<10>, C1-C4-alkyliminooxy, C1-C4-alkoxyamino, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, C1-C4-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, it being possible for the eight last-mentioned radicals, in turn, to be substituted; X is oxygen or NR<8>; n is 0, 1 or 2; R<5> is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; R<6> is C1-C6-alkyl or C1-C6-haloalkyl; R<7> is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; R<8> is hydrogen or C1-C6-alkyl; R<9> is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, phenyl or benzyl; R<10> is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl or C3-C6-alkynyl; Q is a pyrazole of the formula II which is linked in the 4-position   and where R<11> is C1-C6-alkyl, C1-C6-haloalkyl, phenyl or phenyl which is partially or fully halogenated and/or has attached to it one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy; R<12> is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, phenylcarbonyl, phenylcarbonyl-methyl, 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: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy; R<13> is hydrogen, C1-C6-alkyl or C1-C6-haloalkyl; 2. A 4-benzoylpyrazole of the formula I as claimed in Claim 1 where R<1> is nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, -OR<5> or -S(O)nR<7>; R<2> is hydrogen or a radical as mentioned above under R<1>. 3. A 4-benzoylpyrazole of the formula Ia   where the substituents R<1> to R<4>, X and Q have the meanings given under Claim 1 and 2. 4. A process for the preparation of 4-benzoylpyrazoles of the formula I as claimed in Claim 1, which comprises acylating a pyrazole of the formula II (where R<12>=H) where the substituents R<11> and R<13> have the meanings given under Claim 1   with an activated carboxylic acid IIIα or with a carboxylic acid IIIβ,      where the substituents R<1> to R<4> and X have the meanings given under Claim 1 and L<1> is a nucleophilically displaceable leaving group, subjecting the acylation product to a rearrangement reaction, if appropriate in the presence of a catalyst, to give the compounds I (where R<12>=H) and, if desired, to prepare 4-benzoylpyrazoles of the formula I where R<12>  [not equal]  H reacting the product with a compound of the formula V L<2> - R<12> V   (where R<12>  [not equal] H) where R<12> has the meanings given under Claim 1 with the exception of hydrogen and L<2> is a nucleophilically displaceable leaving group. 5. A composition comprising a herbicidally active amount of at least one 4-benzoylpyrazole of the formula I or of an agriculturally useful salt of I as claimed in Claim 1 to 3 and auxiliaries conventionally used for the formulation of crop protection products. 6. A process for the preparation of herbicidally active compositions as claimed in Claim 5, which comprises mixing a herbicidally active amount of at least one 4-benzoylpyrazole of the formula I or of an agriculturally useful salt of I as claimed in Claim 1 to 3 with auxiliaries conventionally used for the formulation of crop protection products. 7. A method of controlling undesirable vegetation, which comprises allowing a herbicidally active amount of at least one 4-benzoylpyrazole of the formula I or of an agriculturally useful salt of I as claimed in Claim 1 to 3 to act on plants, their environment and/or on seeds. 8. The use of 4-benzoylpyrazole of the formula I or of an agriculturally useful salt of I as claimed in Claim 1 to 3 as a herbicide.