New imino:oxy-substituted phenyl:acetic acid derivatives

摘要

2-(2-(Iminooxy)-phenyl)-2-(methoxyimino, methoxymethylene or ethylidene)-acetic acid amide or methyl ester derivatives of formula (I) and their salts are new. R<1> = (a) -C(=NOMe)-COOMe, (b) -C(=NOMe)-CONHMe, (c) -C(=NOMe)-CONH2, (d) -C(=CHOMe)-COOMe or (e) -C(=CHMe)-COOMe; R<2> = CN, NO2, CF3, halogen, 1-4C alkyl or 1-4C alkoxy; m = 0-2; R<3> = H, OH, cyclopropyl, halogen, 1-4C alkyl, CN, 1-4C alkoxy or 1-4C alkylthio; R<4> = 1-8C alkyl, 2-8C alkenyl, 2-8C alkynyl, 3-8C cycloalkyl, aryl or heteroaryl (all optionally partially or completely halogenated or substituted by 1-3 of CN, NO2, OH, SH, NH2, COOH, CONH2, CSNH2, halogen, alkyl, haloalkyl, alkylsulphonyl, alkylsulphoxyl, 3-6C cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, mono- or dialkylamino, mono- or dialkylaminocarbonyl, mono- or dialkylaminothiocarbonyl, alkenyl, alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, heteroaryl and heteroaryloxy); or R<5>-Y-N=C(R<6>)-; R<5> = (i) H; (ii) 1-10C alkyl, 3-6C cycloalkyl, 2-10C alkenyl, 3-10C alkynyl, (1-10C) alkylcarbonyl, (2-10C) alkenylcarbonyl, (3-10C) alkynylcarbonyl or (1-10C) alkylsulphonyl (all optionally partially or completely halogenated or substituted by 1-3 of CN, NO2, OH, SH, NH2, COOH, CONH2, CSNH2, halogen, alkyl, haloalkyl, alkylsulphonyl, alkylsulphoxyl, 3-6C cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, mono- or dialkylamino, mono- or dialkylaminocarbonyl, mono- or dialkylaminothiocarbonyl, alkenyl, alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy and heteroarylthio (where aromatic or heteroaromatic moieties are themselves optionally partially or completely halogenated or substituted by 1-3 of CN, NO2, OH, SH, NH2, COOH, CONH2, CSNH2, halogen, alkyl, haloalkyl, alkylsulphonyl, alkylsulphoxyl, 3-6C cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, mono- or dialkylamino, mono- or dialkylaminocarbonyl, mono- or dialkylaminothiocarbonyl, alkenyl, alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio and -C(=NOR<7>)-An-R<8>)); or (iii) aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, arylsulphonyl or heteroarylsulphonyl (all optionally partially or completely halogenated or substituted by 1-3 of CN, NO2, OH, SH, NH2, COOH, CONH2, CSNH2, halogen, alkyl, haloalkyl, alkylcarbonyl, alkylsulphonyl, alkylsulphoxyl, 3-6C cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, mono- or dialkylamino, mono- or dialkylaminocarbonyl, mono- or dialkylaminothiocarbonyl, alkenyl, alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy and -C(=NOR<7>)-An-R<8>); A = O, S, NH or N(alkyl); n = 0 or 1; R<7>,R<8> = H or alkyl; R<6> = H, OH, halogen or as R<3>; Y = O or NR<9>; R<9> = H or alkyl; unless specified otherwise alkyl moieties have 1-6C and alkenyl moieties 2-6C. Intermediates of formulae (IV) and (IIA) are also new. R<31> = 1-8C alkyl; X = F or other nucleofugeous leaving group.