Fungicidal oxazolyl and oxadiazolyl derivatives

A compound of formula (I):

• wherein Q is oxazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazol-3-yl or 1,2,4-oxadiazol-5-yl;
• Z is CH or N;
• A is hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, cyano, nitro or trifluoromethyl;
• X is halogen, C.sub.1-8 alkyl, C.sub.1-8 haloalkyl, C.sub.1-8 hydroxyalkyl, C.sub.1-8 alkoxy(C.sub.1-8)alkyl, C.sub.1-8 haloalkoxy(C.sub.1-8)alkyl, aryl(C.sub.1-8)alkyl, aryloxy(C.sub.1-8)alkyl, heteroaryl(C.sub.1-8) alkyl, heteroaryloxy(C.sub.1-8) alkyl, C.sub.3-6 cycloalkyl(C.sub.1-8)alkyl, arylthio(C.sub.1-8)alkyl, heteroarylthio(C.sub.1-8)alkyl, R.sup.1' R.sup.2' C.dbd.NO(C.sub.1-8)alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.2-8 haloalkenyl, C.sub.2-8 haloalkynyl, aryl(C.sub.2-8)alkenyl, aryl(C.sub.2-8)alkynyl, aryloxy(C.sub.2-8)alkenyl, aryloxy(C.sub.2-8) alkynyl, arylthio(C.sub.2-8)alkenyl, arylthio(C.sub.1-8)alkynyl, heteroaryl(C.sub.2-8)alkenyl, heteroaryl(C.sub.2-8)alkynyl, heteroaryloxy(C.sub.2-8)alkenyl, heteroaryloxy(C.sub.2-8)alkynyl, heteroarylthio(C.sub.2-8)alkenyl, heteroarylthio(C.sub.2-8)alkynyl, aryl, heteroaryl, C.sub.3-6 cycloalkyl, OR.sup.1, SR.sup.1, SOR.sup.1, SO.sub.2 R.sup.1, COR.sup.1, CO.sub.2 R.sup.1, NR.sup.1 R.sup.2 or CONR.sup.1 R.sup.2 ;
• and R.sup.1 and R.sup.2 are, independently, hydrogen, C.sub.1-8 alkyl, C.sub.1-8 haloalkyl, C.sub.1-8 hydroxyalkyl, C.sub.1-8 alkoxy(C.sub.1-8)alkyl, C.sub.1-8 haloalkoxy(C.sub.1-8)alkyl, aryl(C.sub.1-8)alkyl, aryloxy(C.sub.1-8) alkyl, heteroaryl(C.sub.1-8) alkyl, heteroaryloxy(C.sub.1-8) alkyl, C.sub.3-6 cycloalkyl(C.sub.1-8)alkyl, arylthio(C.sub.1-8)alkyl, heteroarylthio(C.sub.1-8)alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.2-8 haloalkenyl, C.sub.2-8 haloalkynyl, aryl(C.sub.2-8)alkenyl, aryl(C.sub.2-8)alkynyl, aryloxy(C.sub.2-8) alkenyl, aryloxy(C.sub.2-8)alkynyl, arylthio(C.sub.1-8)alkenyl, arylthio(C.sub.1-8)alkynyl, heteroaryl(C.sub.2-8)alkenyl, heteroaryl(C.sub.2-8)alkynyl, heteroaryloxy(C.sub.2-8)alkenyl, heteroaryloxy(C.sub.2-8)allynyl, heteroarylthio(C.sub.2-8)alkenyl, heteroarylthio(C.sub.2-8)alkynyl, aryl, heteroaryl, or C.sub.3-6 cyclolkyl;
• R.sup.1' and R.sup.2' are, independently, hydrogen, C.sub.1-8 alkyl, C.sub.1-8 haloalkyl, C.sub.1-8 hydroxyalkyl, C.sub.1-8 alkoxy(C.sub.1-8)alkyl, C.sub.1-8 haloalkoxy(C.sub.1-8) alkyl, aryl(C.sub.1-8)alkyl, aryloxy(C.sub.1-8)alkyl, heteroaryl(C.sub.1-8) alkyl, heteroaryloxy(C.sub.1-8) alkyl, C.sub.3-6 cycloalkyl(C.sub.1-8)alkyl, arylthio(C.sub.1-8)alkyl, heteroarylthio(C.sub.1-8)alkyl, C.sub.2-8) alkenyl, C.sub.2-8 alkynyl, C.sub.2-8 haloalkenyl, C.sub.2-8 haloalkynyl, aryl(C.sub.2-8)alkenyl, aryl(C.sub.2-8)alkynyl, aryloxy(C.sub.2-8)alkenyl, aryloxy(C.sub.2-8)alkynyl, arylthio(C.sub.2-8)alkenyl, arylthio(C.sub.1-8)alkynyl, heteroaryl(C.sub.2-8)alkenyl, heteroaryl(C.sub.2-8)alkynyl, heteroaryloxy(C.sub.2-8)alkenyl, heteroaryloxy(C.sub.2-8)alkynyl, heteroarylthio(C.sub.2-8)alkenyl, heteroarylthio(C.sub.2-8)alkynyl, aryl, heteroaryl, C.sub.3-6 cycloalkyl, C.sub.1-8 alkoxy, C.sub.1-8 haloalkoxy, aryloxy, heteroaryloxy, nitro, halogen, NR'R" or cyano, or R.sup.1' and R.sup.2' join to form either a C.sub.5-10 aliphatic, aromatic or mixed aliphatic/aromatic carbocyclic ring system or a 5- to 10-membered heterocyclic ring system;
• the foregoing aryl and heteroaryl rings are optionally substituted with:halogen, hydroxy, mercapto, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 alkoxy, C.sub.2-4 alkenyloxy, C.sub.2-4 alkynyloxy, halo(C.sub.1-4)alkyl, halo(C.sub.1-4)alkoxy, C.sub.1-4 alkylthio, 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, methylenedioxy optionally substituted with fluorine or C.sub.1-4 alkyl, aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy, aryl(C.sub.1-4)alkyl wherein the alkyl moiety is optionally substituted with hydroxy, heteroaryl(C.sub.1-4)alkyl, aryl(C.sub.2-4) alkenyl, heteroaryl(C.sub.2-4)alkenyl, aryl(C.sub.1-4)alkoxy, heteroaryl(C.sub.1-4)alkoxy, aryloxy(C.sub.1-4)alkyl, heteroaryloxy(C.sub.1-4)alkyl, C.sub.1-4 alkanoyloxy, 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", or two substituents, when they are in adjacent positions on the aryl or heteroaryl ring can join to form a fused aliphatic ring;
• substituents which may be present in the aryl or heteroaryl rings of any of the foregoing substituents include one or more of the following:halo, hydroxy, mercapto, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 alkoxy, C.sub.2-4 alkenyloxy, C.sub.2-4 alkynyloxy, halo(C.sub.1-4)alkyl, halo(C.sub.1-4)alkoxy, C.sub.1-4 alkylthio, 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, alkanoyloxy, 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";
• 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'R" they can together form a 5- or 6-membered heterocyclic ring;
• aryl is phenyl or napthyl;
• heteroaryl is pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-, 1,2,4- or 1,3,5-triazinyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3- or 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, indolinyl, isoindolinyl, 1- or 2-benzofuranyl, 1- or 2-benzothienyl, benzimidazolinyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, benzisoxazolyl, benzisothiazolyl, benzpyrazolyl, benzoxazolyl, benzthiazolyl, tetrazolyl and thiazolo[5,4-b]pyrid-2-yl, or an N-oxide thereof.