Pyridylacetic acid derivatives, their preparation, intermediates for their preparation and compositions containing them

A pyridylacetic acid compound of the formula I ##STR26## where X is NOCH.sub.3, CHOCH.sub.3, CHCH.sub.3 or CHCH.sub.2 CH.sub.3 ;

• Y is oxygen or NR';
• R' is hydrogen or C.sub.1 -C.sub.4 -alkyl;
• R is cyano, nitro, trifluoromethyl, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
• m is 0, 1 or 2, and the radicals R may be different when m is 2;
• R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl;
• R.sup.2 is hydrogen, cyano, nitro, hydroxyl, amino, halogen,
• C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino or di-C.sub.1 -C.sub.4 -alkylamino;
• R.sup.3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen,
• C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.2 -C.sub.6 -alkenylthio, C.sub.2 -C.sub.6 -alkenylamino, N-C.sub.2 -C.sub.6 -alkenyl-N-C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkynyl, C.sub.2 -C.sub.6 -alkynyloxy, C.sub.2 -C.sub.6 -alkenylthio, C.sub.2 -C.sub.6 -alkynylamino or N-C.sub.2 -C.sub.6 -alkynyl-N-C.sub.1 -C.sub.6 -alkylamino, where the hydrocarbon radicals of these groups may be partly or completely halogenated or may carry from one to three of the following radicals:
• cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkenyloxy , C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C.sub.1 -C.sub.4 -alkoxy, arylthio, aryl-C.sub.1 -C.sub.4 -alkylthio, hetaryl, hetaryloxy, hetaryl-C.sub.1 -C.sub.4 -alkoxy, hetarylthio or hetaryl-C.sub.1 -C.sub.4 -alkylthio, where the cyclic radicals in turn may be partially or completely halogenated and/or may carry from one to three of the following groups:
• cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(.dbd.NOR.sup.a)--A.sub.n --R.sup.b ;
• C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyloxy, C.sub.3 -C.sub.6 -cycloalkylthio, C.sub.3 -C.sub.6 -cycloalkylamino, N-C.sub.3 -C.sub.6 -cycloalyl-N-C.sub.1 -C.sub.6 -alkylamino, C.sub.3 -C.sub.6 -cycloalkenyl, C.sub.3 -C.sub.6 -cycloalkenyloxy, C.sub.3 -C.sub.6 -cycloalkenylthio, C.sub.3 -C.sub.6 -cycloalkenylamino, N-C.sub.3 -C.sub.6 -cycloalkenyl-N-C.sub.1 -C.sub.6 -alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N-C.sub.1 -C.sub.6 -alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-C.sub.1 -C.sub.6 -alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino or N-hetaryl-N-C.sub.1 -C.sub.6 -alkylamino, where the cyclic radicals may be partially or completely halogenated or may carry from one to three of the following groups:
• cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy, C(.dbd.NOR.sup.a)--A.sub.n --R.sup.b or NR.sup.f --CO--D--R.sup.g ;
• R.sup.4 is hydrogen,
• C.sub.1 -C.sub.10 -alkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.2 -C.sub.10 -alkynyl, C.sub.1 -C.sub.10 -alkylcarbonyl, C.sub.2 -C.sub.10 -alkenylcarbonyl, C.sub.3 -C.sub.10 -alkenylcarbonyl or C.sub.1 -C.sub.10 alkylsulfonyl, where these radicals may be partially or completely halogenated or may carry from one to three of the following groups:
• cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy or hetarylthio, where the cyclic groups in turn may be partially or completely halogenated or may carry from one to three of the following groups:
• cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkyloxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(.dbd.NOR.sup.a)--A.sub.n --R.sup.b ;
• C.sub.3 -C.sub.6 -cycloalkyl, aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these radicals may be partially or completely halogenated or may carry from one to three of the following groups:
• cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkyloxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy, C(.dbd.NOR.sup.a)--A.sub.n --R.sup.b or NR.sup.f --CO--D--R.sup.g ;
• A is oxygen, sulfur or nitrogen and the nitrogen carries hydrogen or C.sub.1 -C.sub.6 -alkyl;
• D is a direct bond, oxygen or NR.sup.h ;
• n is 0 or 1;
• R.sup.a and R.sup.b are each hydrogen or C.sub.1 -C.sub.6 -alkyl;
• R.sup.f is hydrogen, hydroxyl, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.2 -C.sub.6 -alkynyloxy, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkoxycarbonyl;
• R.sup.g, R.sup.h independently of one another, are each hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkenyl, aryl, aryl-C.sub.1 -C.sub.6 -alkyl, hetaryl or hetaryl-C.sub.1 -C.sub.6 -alkyl;
• and salts thereof.