Preparation of a-methoxyiminocarboxylic acid methylamides and intermediates therefore

A process for preparing .alpha.-methoxyiminocarboxylic acid methylamides of the formula IA ##STR47## where the substituents and the index have the following meanings:

• X is nitro, trifluoromethyl, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,
• n is 0 or an integer of from 1 to 4, where the X radicals can be different if n>1,
• R.sup.1 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, unsubstituted or substituted alkylsulfonyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylsulfonyl, unsubstituted or substituted heterocyclyl or unsubstituted or substituted hetaryloxy, ##STR48## R.sup.a is cyano, nitro, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -haloalkoxy,
• m is 0 or an integer of from 1 to 4, where the R.sup.a radicals can be different if m>1,
• R.sup.b is hydrogen, unsubstituted or substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, heterocyclyl, alkylcarbonyl, cycloalkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, heterocyclylcarbonyl, alkoxycarbonyl, aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl, hetarylsulfonyl or a C(R')=NOR" group;
• R.sup.1 is hydrogen, hydroxyl, cyano, nitro, amino, halogen, unsubstituted or substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkynyl, alkynyloxy, alkynylthio, alkynylamino, cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkenyl, cycloalkenyloxy, cycloalkenylthio, cycloalkenylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, aryl, aryloxy, arylthio, arylamino, heteroaryl, heteroaryloxy, heteroarylthio or heteroarylamino;
• R" is hydrogen, unsubstituted or substituted alkyl, cycloalkyl, alkenyl, alkynyl, heterocyclyl, aryl or heteroaryl,
• R.sup.c is a group mentioned under R.sup.b or hydroxyl, cyano, nitro, amino, halogen, unsubstituted or substituted alkoxy, alkylthio, alkylamino, dialkylamino, aryloxy, arylthio, arylamino, hetaryloxy, hetarylthio or hetarylamino;
• unsubstituted or substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl,
• or
• R.sup.b and R.sup.c, together with the C atom to which they are bonded, are a carbocyclic or heterocyclic ring, by Pinner reaction of an acyl cyanide of the formula IIA ##STR49## with an alcohol and subsequent reaction of the ester formed in the Pinner reaction, of the formula IVA ##STR50## a) with hydroxylamine to give the oxime of the formula VA ##STR51## methylation of VA to give the oxime ether of the formula VIA ##STR52## or b) with O-methylhydroxylamine to give the oxime ether of the formula VIA
• and subsequent reaction of VIA with methylamine, wherein in the Pinner reaction an alcohol of the formula III
• R--OH (III)
• is used whose boiling point is above 75.degree. C.