Aralkyoxy alkoximino derivatives and their use as fungicides

Details Aralkyoxy alkoximino derivatives and their use as fungicides Aralkyoxy alkoximino derivatives and their use as fungicides

1995-07-31

1999-08-10

Dees, Jose' G.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

514538, 560 35, A61K 3115

Patent

active

059359994

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to oxime derivatives that are useful as fungicides, to a process for preparing them, to compositions containing them and to methods of using them to combat fungi, especially fungal infections of plants.
According to the present invention there is provided a compound having the general formula (I), wherein R.sup.1 and R.sup.2 are independently hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-6 cycloalkyl, aryl or aryl(C.sub.1-4)alkyl; R.sup.3 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl or C.sub.3-6 cycloalkyl; A is oxygen or sulphur; W is CH.sub.3 O.CH.dbd.CCO.sub.2 CH.sub.3, CH.sub.3 O.N.dbd.CCONR.sup.4 R.sup.5, CH.sub.3 O.CH.dbd.CCONR.sup.4 R.sup.5 or CH.sub.3 O.N.dbd.CCO.sub.2 CH.sub.3 and stereoisomers thereof; X, Y and Z are independently hydrogen, halogen, hydroxy, mercapto, C.sub.1-4 alkyl (especially methyl and ethyl), C.sub.2-4 alkenyl (especially allyl), C.sub.2-4 alkynyl (especially propargyl), C.sub.1-4 alkoxy (especially methoxy), C.sub.2-4 alkenyloxy (especially allyloxy), C.sub.2-4 alkynyloxy (especially propargyloxy), halo(C.sub.1-4)alkyl (especially trifluoromethyl), halo(C.sub.1-4)alkoxy (especially trifluoromethoxy), C.sub.1-4 alkylthio (especially methylthio), hydroxy(C.sub.1-4)alkyl, C.sub.1-4 alkoxy(C.sub.1-4)alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl(C.sub.1-4)alkyl, optionally substituted methylenedioxy (especially optionally substituted with fluorine or C.sub.1-4 alkyl), optionally substituted aryl (especially optionally substituted phenyl), optionally substituted heteroaryl (especially optionally substituted pyridyl or pyrimidinyl), optionally substituted heterocyclyl (especially optionally substituted pyrrolidine), optionally substituted aryloxy (especially optionally substituted phenoxy), optionally substituted heteroaryloxy (especially optionally substituted pyridyloxy or pyrimidinyloxy), optionally substituted aryl(C.sub.1-4)alkyl (especially optionally substituted benzyl, optionally substituted phenethyl and optionally substituted phenyl n-propyl) in which the alkyl moiety is optionally substituted with hydroxy, optionally substituted heteroaryl(C.sub.1-4) alkyl (especially optionally substituted pyridyl- or pyrimidinyl(C.sub.1-4)alkyl), optionally substituted aryl(C.sub.2-4)alkenyl (especially optionally substituted phenylethenyl), optionally substituted heteroaryl(C.sub.2-4)alkenyl (especially optionally substituted pyridylethenyl or pyrimidinylethenyl), optionally substituted aryl(C.sub.1-4)alkoxy (especially optionally substituted benzyloxy), optionally substituted heteroaryl(C.sub.1-4 )alkoxy (especially optionally substituted pyridyl- or pyrimidinyl(C.sub.1-4)alkoxy), optionally substituted aryloxy(C.sub.1-4)alkyl (especially phenoxymethyl), optionally substituted heteroaryloxy(C.sub.1-4)alkyl (especially optionally substituted pyridyloxy- or pyrimidinyloxy(C.sub.1-4)alkyl), acyloxy (including C.sub.1-4 alkanoyloxy (especially acetyloxy) and benzoyloxy), cyano, thiocyanato, nitro, --NR'R", --NHCOR', --NHCONR'R", --CONR'R", --COOR', --OSO.sub.2 R', --SO.sub.2 R', --COR', --CR'.dbd.NR" or --N.dbd.CR'R" in which R' and R" are independently hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl(C.sub.1-4 )alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; when R' and R" are in CONR'RN" they can together form a 5- or 6-membered heterocyclic ring (for example a pyrrole, imidazole, pyrrolidine, piperidine or morpholine ring); or two substituents, when they are in adjacent positions on the aryl or heteroaryl ring can join to form a fused alphatic ring (especially to form a fused 6-membered carbon aliphatic ring); and R.sup.4 and R.sup.5 are independently hydrogen or C.sub.1-4 alkyl.
Because the double bond of the propenoate, oxyiminoacetamide or oxyiminoacetate group is unsymmetrically substituted, the compounds of the invention may be obtained in the form o

REFERENCES:
patent: 5055471 (1991-10-01), de Fraine et al.
patent: 5221691 (1993-06-01), Clough et al.
patent: 5238956 (1993-08-01), Clough et al.

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