Patent FR-2777002-A1 (FR)
Title: New hydroximine or hydrazone derivatives, useful as fungicides for protecting plants and seeds
Inventor: DESBORDES PHILIPPE
IPC: C07D213/30
Filed: 1998-04-07
Abstract: Hydroximine or hydrazone derivatives (I) are new. Also new are intermediates (IIIA) and (XV). Imino compounds of formula (I) and their salts and metal or metalloid complexes are new. G  = -C(T)-C(Q2)-R4, -N(T')-C(Q2)-R4, -CH(YR8)-C(Q2)-R4 or a heterocyclic group of formula (i) or (ii); T = =Q1-OR5, =Q1-SR5 or  =CHR6; T' = -(CH2)nOR5, -(CH2)nSR5 or R7; n, p  = 0 or 1; Q1  = N or CH; Q2, Q3 = O or S; Q4  = N or CR11; Q5  = O, S or NR12; or Q2 + R4 = group completing a 5-7 membered ring having 2 or 3 O and/or N atoms, optionally substituted by one or more groups such as halo, alkyl or alkoxy; Y  = O, S, NH or ONH; W1  = O, S, SO or SO2; W2  = O or NR13; A  = 5-10 membered aromatic mono- or bicyclic heterocycle having 1-4 heteroatoms (selected from O, N, N(O), S and S(O)2), attached through C or N, and optionally substituted by 1-5 (preferably 1-3) of X1-X3; X1- X3  = H, halo, OH, SH, NO2, CNS, N3, CN or SF5; alkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl or cycloalkyl (all optionally substituted by halo); cyanoalkyl, cyanoalkoxy, cyanoalkylthio, alkoxysulfonyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, NH2, N-alkylamino, N,N-dialkylamino, acylamino, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, acylaminoalkyl, acyl, COOH, CONH2, N-alkylcarbamoyl, N,N-dialkylcarbamoyl or alkoxycarbonyl; X4  = H, halo, alkyl, haloalkyl, alkoxy, haloalkoxy, CN or NO2; R1, R2  = H; alkyl, cycloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonyl or alkoxythiocarbonyl (all optionally substituted by halo); or cyanoalkyl, CN, acyl, COOH, CONH2, N-alkylcarbamoyl, N,N-dialkylcarbamoyl, alkylthiocarbonyl, alkylthiothiocarbonyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl or acylaminoalkyl;  or R1 + R2 = divalent group, e.g. alkylene, optionally substituted by one or more halo or alkyl; R3  = H; alkyl, cycloalkyl, alkoxy, alkylthio, alkoxyalkyl, alkylthioalkyl, alkoxycarbonyl or alkoxythiocarbonyl (all optionally substituted by halo); cyanoalkyl, NO2, CN, acyl, COOH, CONH2, N-alkylcarbamoyl, N,N-dialkylcarbamoyl, 3-oxetanyloxycarbonyl, alkylthiocarbonyl, alkenyl, alkynyl, N,N-dialkylamino, N,N-dialkylaminoalkyl, phenyl or benzyl (both optionally substituted); R4  = alkyl, cycloalkyl or alkoxy (all optionally substituted by halo); or alkoxyalkyl, alkylthio, alkylamino or dialkylamino; R5, R6  = alkyl or haloalkyl; R7  = alkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkenyl or alkynyl; R8  = H, alkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, CHO or acyl; R9  = H, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkenyl, or alkynyl; R10  = alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl (all optionally substituted by halo); or halo; R11, R12 = H, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkenyl or alkynyl; R13  = H; alkyl, cycloalkyl, alkoxyalkyl,  alkylthioalkyl, alkoxycarbonyl, alkoxythiocarbonyl or alkylsulfonyl (all optionally substituted by halo); allyl, propargyl, benzyl or arylsulfonyl (all optionally substituted); or acyl, N-alkylcarbamoyl, N,N-dialkylcarbamoyl or alkylthiocarbonyl. Independent claims are included for the preparation of (I); the novel intermediates of formulae (IIIA) (provided that W1 = S) and (XV); and the preparation of these intermediates. P' = H or protecting group.