Patent EP-1404666-B1 (EP)
Inventor: HUTIN PIERRE
IPC: A01N43/60
Filed: 2002-07-05
Granted: 2009-05-27
Abstract: 3,4-Disubstituted pyridine-2-carboxylic acid derivatives (I) are new.  Pyridine derivatives of formula (I), including their N-oxides, geometric and/or optical isomers, enantiomers and/or diastereomers, tautomers, salts and metal or metalloid complexes, are new.  Y  =  -(CR6R7)k-Y';  Y'  =  CHO, CH(Q3R4)(Q3R5), -Q4-P(Q7)(OR4)(OR5), C(R14)=NQ5, -N=C(R11)-NR12R13, Het or N(R12)Q6;  G  =  O, S or NR1;  k  =  0-2 (provided that k is not 0 if Y' = -N=C(R11)-NR12R13);  Q1  =  O, S, NR1 or =N-NR4R5;  Q2  =  OR2, SR3 or NR4R5;  or Q1 + Q2  =  group completing a 5-7 membered ring containing 2 or 3 O and/or N atoms (optionally substituted (os) by one or more of halo, alkyl and haloalkyl);  Q3, Q7  =  O or S;  Q4  =  O, S, NR1 or CH2;  Q5  =  OR2, NR4R5 or R1;  Q6  =  OR2 or NR4R5;  X1, X2  =  H, halo, OH, SH, NO2, SCN, N3, CN, SF5, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, haloalkylthioalkyl, cyanoalkyl, cyanoalkoxy, cyanoalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl or alkoxysulfonyl;  or X1 + X2  =  group completing a 4-8 membered saturated or partially or completely unsaturated ring, optionally containing one or more S, O, N and/or P heteroatom(s);  Z'  =  H, CN, alkyl, allyl, aryl, aralkyl, propargyl, cycloalkyl, halocycloalkyl, alkenyl, alkynyl, cyanoalkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, haloalkylthioalkyl, mono- or dialkylaminoalkyl, acylaminoalkyl, alkoxycarbonylaminoalkyl, aminocarbonylaminoalkyl, alkoxycarbonyl, mono- or dialkylaminocarbonyl, acyl, thioacyl, alkoxythiocarbonyl, mono- or dialkylaminothiocarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkoxysulfonyl, aminosulfonyl, mono- or dialkylaminosulfonyl, arylsulfinyl, arylsulfonyl, aryloxysulfonyl, mono- or diarylaminosulfonyl, N-alkyl-N-arylaminosulfonyl, -Si(R15)(R16)(R17) or -P(O)(OR15)(OR16);  R1 - R5, R11 - R14  =  1-12C alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, haloalkylthioalkyl, cyanoalkyl, acyl, NO2, =O, CN, COOH, CONH2, 3-oxetanyloxycarbonyl, mono- or dialkylcarbamoyl, alkoxycarbonyl, alkylthiocarbonyl, haloalkoxycarbonyl, alkoxythiocarbonyl, haloalkoxythiocarbonyl, alkylthiothiocarbonyl, alkenyl, alkynyl, mono- or dialkylamino or mono- or dialkylaminoalkyl; or aryl, aralkyl, heterocyclyl or heterocyclylalkyl (all os by one or more of R6, aryl, aralkyl and/or -T-R8);  or R4 + R5, R11 + R13 or R12 + R13  =  group completing a 4-8 membered saturated or partially or completely unsaturated ring, optionally containing one or more S, O, N and/or P heteroatom(s);  T  =  direct bond, (CH2)m (optionally interrupted by one or more of N, O and/or S), oxyalkylene, alkoxyalkylene, CO, OCO, COO, SO, SO2, OSO2, SO2O, OSO, SOO, S, O, vinylene, ethynylene, NR9, NR9O, ONR9, N=N, NR9NR10, NR9S, NR9SO, NR9SO2, SNR9, SONR9, SO2NR9, CONR9O or ONR9CO;  m  =  1-12;  R8  =  H, aryl or heterocyclyl;  R6, R7, R9, R10  =  H, halo, OH, SH, NO2, SCN, N3, CN, SF5, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxyalkyl, alkoxycarbonyl, haloalkoxyalkyl, alkylthioalkyl, haloalkylthioalkyl, aryl, aralkyl, cyanoalkyl, cyanoalkoxy, cyanoalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl or alkoxysulfonyl;  R15 - R17  =  H, halo, alkyl, haloalkyl, alkoxyalky, aryl or aralkyl. Independent claims are included for:  (i) the preparation of (I); and  (ii) the preparation of intermediates (IIn) of formula (I; Y replaced by -(CR6R7)k-CH2NH2).