Production of substituted aryl ketone compounds for use as agrochemicals, e.g. herbicides, involves reacting C-H acid compounds with substituted benzoic acids in presence of cyclic phosphonic acid anhydride
Substituted aryl ketones are obtained by reacting C-H acid compounds with substituted benzoic acids in presence of a cyclic phosphonic acid anhydride, other auxiliary reactant(s) and aprotic polar solvent(s) at -30 to +150 deg C. A method for the production of compounds of formula (I) (including all possible tautomeric forms) involves reacting C-H acid compounds of formula R<1>-H (II) with substituted benzoic acids (III) in presence of a phosphonic acid anhydride (IV), other auxiliary reaction component(s) and aprotic polar diluent(s) at -30 to +150 deg C, optionally with isolation of intermediate products. R<1> = R<12>C(O)CH(R<13>- or a group of formula (i)-(iii); m = 0-6; R<5> = halo or optionally substituted alkyl, alkylthio or aryl; or 2R<5> = alkylene group; R<6> = OH, formyloxy or halo, or optionally substituted alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylamino-carbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, aryloxy, arylthio, aryl-sulfinyl, arylsulfonyl, arylcarbonyloxy, arylcarbonylalkoxy, arylsulfonyloxy, arylalkoxy, arylalkylthio, arylalkylsulfinyl or arylalkylsulfonyl; R<7> = H, CN, carbamoyl, thiocarbamoyl, halo, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl or cycloalkyl; R<8> = H or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl; R<9> = OH, formyloxy or optionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy; R<10>, R<13> = H, CN, carbamoyl, thiocarbamoyl, halo or optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl; R<11>, R<12> = H or optionally substituted alkyl or cycloalkyl; R<2>, R<3> = H, nitro, CN, carboxy, carbamoyl, thiocarbamoyl, halo, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl; R<4> = R<2> or optionally substituted cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkylalkoxy, cycloalkylalkylthio, cycloalkylalkylamino, aryl, aryloxy, arylthio, arylamino, arylalkyl, arylalkoxy, arylalkylthio, arylalkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio, heterocyclylalkylamino, heterocyclyloxyalkyl, heterocyclylthioalkyl or heterocyclylaminoalkyl; and R = alkyl or aryl.
