Fungicides

A compound of the general formula (1):

• wherein
• X, Y and Z are independently H, halogen, C1-4 alkyl, halo(C1-4)alkyl, C2-4 alkenyl, halo(C2-4)alkenyl, C2-4 alkynyl, halo(C2-4)alkynyl, C1-4 alkoxy, halo(C1-4)alkoxy, —S(O)n(C1-4)alkyl where n is 0, 1 or 2 and the alkyl group is optionally substituted with fluoro, —OSO2(C1-4)alkyl where the alkyl group is optionally substituted with fluoro, cyano, nitro, C1-4 alkoxycarbonyl, —CONR′R″, —COR′, —NR′COR″ or —NR′COOR′″ where R′ and R″ are independently H or C1-4 alkyl and R′″ is C1-4 alkyl, provided that at least one of X and Z is other than H;
• R1 is a straight-chain C1-4 alkyl group;
• R2 is H, C1-4 alkyl, C1-4 alkoxymethyl or benzyloxymethyl in which the phenyl ring of the benzyl moiety is optionally substituted with C1-4 alkoxy;
• R3 and R4 are independently H, C1-3alkyl, C2-3alkenyl or C2-3 alkynyl provided that both are not H and that when both are other than H their combined total of carbon atoms does not exceed 4, or
• R3 and R4 join with the carbon atom to which they are attached to form a 3 or 4 membered carbocyclic ring optionally containing one O, S or N atom and optionally substituted with halo or C1-4 alkyl;
• and
• R5 is H, C1-4 alkyl or C3-6 cycloalkyl in which the alkyl or cycloalkyl group is optionally substituted with halo, hydroxy, C1-6 alkoxy, cyano, C1-4 alkylcarbonyloxy, aminocarbonyloxy, mono- or di(C1-4)alkylaminocarbonyloxy, —S(O)n(C1-6)alkyl where n is 0, 1 or 2, triazolyl, tri(C1-4)-alkylsilyloxy, optionally substituted phenoxy, optionally substituted thienyloxy, optionally substituted benzyloxy or optionally substituted thienylmethoxy, or
• R5 is optionally substituted phenyl, optionally substituted thienyl or optionally substituted benzyl,
• in which the optionally substituted phenyl and thienyl rings of the R5 values are optionally substituted with one, two or three substituents selected from halo, hydroxy, mercapto, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 alkoxy, C2-4 alkenyloxy, C2-4 alkynyloxy, halo(C1-4)alkyl, halo(C1-4)alkoxy, C1-4 alkylthio, halo(C1-4)alkylthio, hydroxy(C1-4)alkyl, C1-4 alkoxy(C1-4)alkyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, —NRmRn, —NHCORm, —NHCONRmRn, —CONRmRn, —SO2Rm, —OSO2Rm, —CORm, —CRm═NRn or —N═CRmRn, in which Rm and Rn are independently hydrogen, C1-4 alkyl, halo(C1-4)alkyl, C1-4 alkoxy, halo(C1-4)alkoxy, C1-4 alkylthio, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl or C1-4 alkoxy;
• provided that R5 is not H when (i) X, Z, R1, R3 and R4 are all methyl and Y, and R2 are both H, (ii) X, Z, R3 and R4 are all methyl, Y is chloro, R1 is ethyl and R2 is H, (iii) X and Z are both chloro, R1 is methyl or ethyl, R3 and R4 are both methyl and Y and R2 are both H, (iv) X, Y and Z are all chloro, R1, R3 and R4 are all methyl and R2 is H, and (v) Y is chloro, Z is trifluoromethyl, R1, R3 and R4 are all methyl and X and R2 are both H.

A compound of the general formula (1):

• wherein
• X, Y and Z are independently H, fluoro, bromo, iodo, C2-4 alkyl, halo(C1-4)alkyl, C2-4 alkenyl, halo(C2-4)alkenyl, C2-4 alkynyl, halo(C2-4)alkynyl, C1-4 alkoxy, halo(C1-4)alkoxy, —S(O)n(C1-4)alkyl where n is 0, 1 or 2 and the alkyl group is optionally substituted with fluoro, —OSO2(C1-4)alkyl where the alkyl group is optionally substituted with fluoro, cyano, nitro, C1-4 alkoxycarbonyl, —CONR′R″, —COR′, —NR′COR″ or —NR′COOR′″ where R′ and R″ are independently H or C1-4 alkyl and R′″ is C1-4 alkyl, provided that at least one of X and Z is other than H;
• R1 is a straight-chain C1-4 alkyl group;
• R2 is H, C1-4 alkyl, C1-4 alkoxymethyl or benzyloxymethyl in which the phenyl ring of the benzyl moiety is optionally substituted with C1-4 alkoxy;
• R3 and R4 are independently H, C1-3 alkyl, C2-3 alkenyl or C2-3 alkynyl provided that both are not H and that when both are other than H their combined total of carbon atoms does not exceed 4, or
• R3 and R4 join with the carbon atom to which they are attached to form a 3 or 4 membered carbocyclic ring optionally containing one O, S or N atom and optionally substituted with halo or C1-4 alkyl;
• and
• R5 is H, C1-4 alkyl or C3-6 cycloalkyl in which the alkyl or cycloalkyl group is optionally substituted with halo, hydroxy, C1-6 alkoxy, cyano, C1-4 alkylcarbonyloxy, aminocarbonyloxy, mono- or di(C1-4)alkylaminocarbonyloxy, —S(O)n(C1-6)alkyl where n is 0, 1 or 2, triazolyl (e.g. 1,2,4-triazol-1-yl), tri(C1-4)-alkylsilyloxy, optionally substituted phenoxy, optionally substituted thienyloxy, optionally substituted benzyloxy or optionally substituted thienylmethoxy, or R5 is optionally substituted phenyl, optionally substituted thienyl or optionally substituted benzyl,
• in which the optionally substituted phenyl and thienyl rings of the R5 values are optionally substituted with one, two or three substituents selected from halo, hydroxy, mercapto, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 alkoxy, C2-4 alkenyloxy, C2-4 alkynyloxy, halo(C1-4)alkyl, halo(C1-4)alkoxy, C1-4 alkylthio, halo(C1-4)alkylthio, hydroxy(C1-4)alkyl, C1-4alkoxy(C1-4)alkyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, —NRmRn, —NHCORm, —NHCONRmRn, —CONRmRn, —SO2Rm, —OSO2Rm, —CORm, —CRm═NRn or —N═CRmRn, in which Rm and Rn are independently hydrogen, C1-4 alkyl, halo(C1-4)alkyl, C1-4 alkoxy, halo(C1-4)alkoxy, C1-4 alkylthio, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl or C1-4 alkoxy.

A compound of the general formula (1):

• wherein
• X, Y and Z are independently H, halogen, C1-4 alkyl, halo(C1-4)alkyl, C2-4 alkenyl, halo(C2-4)alkenyl, C2-4 alkynyl, halo(C2-4)alkynyl, C1-4 alkoxy, halo(C1-4)alkoxy, —S(O)n(C1-4)alkyl where n is 0, 1 or 2 and the alkyl group is optionally substituted with fluoro, —OSO2(C1-4)alkyl where the alkyl group is optionally substituted with fluoro, cyano, nitro, C1-4 alkoxycarbonyl, —CONR′R″, —COR′, —NR′COR″ or —NR′COOR′″ where R′ and R″ are independently H or C1-4 alkyl and R′″ is C1-4 alkyl, provided that at least one of X and Z is other than H;
• R1 is a straight-chain C1-4 alkyl group;
• R2 is H, C1-4 alkyl, C1-4 alkoxymethyl or benzyloxymethyl in which the phenyl ring of the benzyl moiety is optionally substituted with C1-4 alkoxy;
• R3 and R4 are independently H, C1-3 alkyl, C2-3 alkenyl or C2-3 alkynyl provided that both are not H and that when both are other than H their combined total of carbon atoms does not exceed 4, or
• R3 and R4 join with the carbon atom to which they are attached to form a 3 or 4 membered carbocyclic ring optionally containing one O, S or N atom and optionally substituted with halo or C1-4 alkyl;
• and
• R5 is C1-4 alkyl or C3-6 cycloalkyl in which the alkyl or cycloalkyl group is optionally substituted with halo, hydroxy, C1-6 alkoxy, cyano, C1-4 alkylcarbonyloxy, aminocarbonyloxy, mono- or di(C1-4)alkylaminocarbonyloxy, —S(O)n(C1-6)alkyl where n is 0, 1 or 2, triazolyl (e.g. 1,2,4-triazol-1-yl), tri(C1-4)-alkylsilyloxy, optionally substituted phenoxy, optionally substituted thienyloxy, optionally substituted benzyloxy or optionally substituted thienylmethoxy, or R5 is optionally substituted phenyl, optionally substituted thienyl or optionally substituted benzyl,
• in which the optionally substituted phenyl and thienyl rings of the R5 values are optionally substituted with one, two or three substituents selected from halo, hydroxy, mercapto, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 alkoxy, C2-4 alkenyloxy, C2-4 alkynyloxy, halo(C1-4)alkyl, halo(C1-4)alkoxy, C1-4 alkylthio, halo(C1-4)alkylthio, hydroxy(C1-4)alkyl, C1-4alkoxy(C1-4)alkyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, —NRmRn, —NHCORm, —NHCONRmRn, —CONRmRn, —SO2Rm, —OSO2Rm, —CORm, —CRm═NRn or —N═CRmRn, in which Rm and Rn are independently hydrogen, C1-4 alkyl, halo(C1-4)alkyl, C1-4 alkoxy, halo(C1-4)alkoxy, C1-4 alkylthio, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl or C1-4 alkoxy.