Claims
- 1. 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.
- 2. A compound of the formula I as claimed in claim 1, in which
- R.sup.2 is hydrogen, hydroxyl, cyclopropyl, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio;
- R.sup.3 is hydrogen, hydroxyl, halogen, cyclopropyl, cyclohexyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio,
- aryl or hetaryl, where these groups may be partially or completely halogenated or may carry from one to 3 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 or hetaryloxy;
- R.sup.4 is hydrogen,
- C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl, 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 groups may be partially or completely halogenated or may carry from one to 3 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, arylthio, hetaryl, hetaryloxy or hetarylthio, where the aromatic and heteroaromatic radicals 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 ;
- aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl, where these groups may be partially or completely halogenated or may carry from one to 3 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 -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 or C(.dbd.NOR.sup.a )--A.sub.n --R.sup.b.
- 3. A compound of the formula I as claimed in claim 1, in which Y is NR' and X is NOCH.sub.3.
- 4. A compound of the formula I as claimed in claim 1, in which m is 0.
- 5. A compound of the formula I as claimed in claim 1, in which R.sup.1 is methyl.
- 6. A process for the preparation of a compound of the formula I as claimed in claim 1, in which R.sup.2 is not halogen, wherein a benzyl compound of the formula II ##STR27## where L.sup.1 is a nucleophilically replaceable leaving group, is reacted with a hydroximine of the formula III
- R.sup.4 ON.dbd.C(R.sup.3)--C(R.sup.2).dbd.NOH III.
- 7. A process for the preparation of a compound of the formula I as claimed in claim 1, in which R.sup.2 and R.sup.3 are not halogen, wherein a benzyl compound of the formula II as claimed in claim 1 is reacted with a dihydroximine of the formula IV
- HON.dbd.C(R.sup.3)--C(R.sup.2).dbd.NOH IV
- to give a compound of the formula V ##STR28## and V is then reacted with a compound of the formula VI
- R.sup.4 --L.sup.1 VI
- where L.sup.2 is a nucleophilically replaceable leaving group, to give I.
- 8. A process for the preparation of a compound of the formula I as claimed in claim 1, in which R.sup.2 is not halogen, wherein a benzyl derivative of the formula II as claimed in claim 1 is reacted with a carbonylhydroximine of the formula VII
- O.dbd.C(R.sup.3)--C(R.sup.2).dbd.NOH VII
- to give a compound of the formula VIII ##STR29## and VIII is then reacted either a) first with hydroxylamine or its salt and then with a compound of the formula VI (R.sup.4 --L.sup.2) as claimed in claim 7 or
- b) with a hydroxylamine or a hydroxylammonium salt of the formula IXa or IXb, respectively ##STR30## where Q.crclbar. is an anion of an acid, to give I.
- 9. A process for the preparation of a compound I as claimed in claim 1, in which Y is oxygen (IA), wherein a methylpyridinecarboxylate of the formula X ##STR31## where R.sup.x is C.sub.1 -C.sub.4 -alkyl, is converted into the corresponding methylenepyridinecarboxylate of the formula XI ##STR32## XI is then converted into the corresponding pyridinecarboxylate of the formula XII by reaction with a hydroximine of the formula III
- R.sup.4 ON.dbd.C(R3--C(R.sup.2).dbd.NOH III ##STR33## XII is reduced to the alcohol XIII ##STR34## XIII is oxidized to the pyridinealdehyde XIV ##STR35## XIV is converted into the cyanhydrin XV ##STR36## XV is then hydrolyzed to the corresponding mandelate XVI ##STR37## XVI is oxidized to the .alpha.-keto ester XVII ##STR38## and XVII is then converted either a) with O-methylhydroxylamine (H.sub.2 NOCH.sub.3) or an O-methylhydroxylammonium salt, or
- b) with an ethylene-Wittig or -Wittig-Horner reagent, or
- c) with a methoxy-Wittig or -Wittig-Horner reagent
- into the corresponding pyridylacetate IA.
- 10. A process for the preparation of a compound I in which Y is NR'(IB), wherein the corresponding pyridylacetate of the formula IA as claimed in claim 9 is reacted with an amine of the formula XVIII
- HNR'R.sup.1 XVIII.
- 11. A process for the preparation of a compound I as claimed in claim 1, wherein a hydroxylamine compound of the formula IIa ##STR39## is reacted with a carbonyl compound of the formula VIIa
- O.dbd.C(R.sup.2)--C(R.sup.3).dbd.NOR.sup.4 VIIa.
- 12. A process for the preparation of a compound I as claimed in claim 1, in which Y is oxygen (IA), wherein a methylpyridinecarboxylate of the formula X ##STR40## where R.sup.x is C.sub.1 -C.sub.4 -alkyl, is reduced to the alcohol of the formula XIIIa ##STR41## XIIIa is oxidized to the pyridinealdehyd XIVa into the corresponding pyridylacetate XVIIIa, XVIIIb or XVIIIc, respectively ##STR42## XVIIIa, XVIIIb or XVIIIc is then halogenated to give the benzyl halide XIXa, XIXb or XIXc, respectively ##STR43## where Hal is chlorine or bromine, and XIXa, XIXb or XIXc is then converted into the corresponding pyridylacetate IA by reaction with a hydroximine of the formula III
- R.sup.4 ON.dbd.C(R3--C(R.sup.2).dbd.NOH III.
- 13. A compound of the formula II as claimed in claim 6.
- 14. A compound of the formula VIII as claimed in claim 8.
- 15. A compound of the formula XII, XIII, XIV, XV, XVI or XVII as claimed in claim 9.
- 16. A compound of the formula IIa as claimed in claim 11.
- 17. A compound of the formula XVIIIa ##STR44## wherein R.sup.1 is methyl and R is cyano, nitro, trifluoromethyl, halogen, C.sub.1-4 -alkyl or C.sub.1-4 -alkoxy; and m is 0, 1 or 2, and the radicals R may be different when m is 2.
- 18. A pesticide or fungicide containing a solvent or carrier and an effective amount of a compound of the formula I as claimed in claim 1.
- 19. A pesticide as claimed in claim 18 for controlling animal pests from the class consisting of the insects, arachnids or nematodes.
- 20. A method for controlling animal pests or harmful fungi, wherein the pests or harmful fungi, their habitat, or the plants, surfaces, materials or spaces to be kept free from them are treated with an effective amount of a compound of the formula I as claimed in claim 1.
Priority Claims (1)
Number |
Date |
Country |
Kind |
19540989 |
Nov 1995 |
DEX |
|
Parent Case Info
This application is a 371 of PCT/EP 96/04676 filed Oct. 18, 1996.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/EP96/04676 |
10/28/1996 |
|
|
4/29/1998 |
4/29/1998 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO97/17328 |
5/15/1997 |
|
|
Foreign Referenced Citations (4)
Number |
Date |
Country |
2182529 |
Aug 1995 |
CAX |
2182407 |
Aug 1995 |
CAX |
9518789 |
Jul 1995 |
WOX |
9611183 |
Apr 1996 |
WOX |