Fungicidal phenoxyphenylhydrazine derivatives

A method for controlling fungi comprising contacting the fungi with a fungicidally effective amount of a phenoxyphenylhydrazine compound of the formula:

• a)
• wherein
• Q is —NY—NH—, —N═N—, or
• X is oxygen, sulfur, sulfoxide, or sulfone;
• n is 0 or 1;
• Y is hydrogen, C1–C4 alkanoyl, C1–C4 haloalkanoyl, C1–C6 straight chain or branched alkoxycarbonyl, C1–C4 alkoxy(C1–C4)alkoxycarbonyl, C1–C4 alkyl, or C1–C4 haloalkyl;
• R1is C1–C6 alkoxy, C3–C6 branched alkoxy, C3–C6 cycloalkoxy, phenoxy, benzyloxy, C2–C6 alkenyloxy, C2–C6 alkynyloxy, C1–C6 haloalkoxy, silyloxy, (C1–C6 alkoxy)-carbonylmethoxy, C1–C6 thioalkoxy, C1–C6 alkylamino, C1–C6 alkyl, C3–C6 branched alkyl, (C1–C6 alkoxy)C1–C6 alkoxy, or (C1–C6 alkoxy)carbonyl;
• R2 and R3 are each, independently, hydrogen, halogen, C1–C6 alkyl, C3–C6 branched alkyl, C1–C6 haloalkyl, C1–C6 alkoxy, C1–C6 haloalkoxy, cyano, or (C1–C6 alkoxy)carbonyl;
• R4 is C1–C6 alkyl;
• and
• Z1 and Z2 are each independently, carbon or nitrogen,
• with the proviso that when Z1 is carbon, X is oxygen, and R2 is hydrogen, then R3 cannot be hydrogen;
• or
• b)
• wherein R5 is C1–C6 alkoxy;
• and R6 and R7 are, independently, halo or C1–C6 haloalkyl.

A method for controlling fungi on a plant or plant seed which comprises applying to the plant or the plant seed, or to a growth medium or water in which the plant or plant seed is growing or is to be grown in, a fungicidally effective amount of a compound of the formula:

• a)
• wherein Q is —NY—NH—, —N═N—, or
• X is oxygen, sulfur, sulfoxide, or sulfone;
• n is 0 or 1;
• Y is hydrogen, C1–C4 alkanoyl, C1–C4 haloalkanoyl, C1–C6 straight chain or branchd alkoxycarbonyl, C1–C4 alkoxy(C1–C4)alkoxycarbonyl, C1–C4 alkyl, or C1–C4 haloalkyl;
• R1is C1–C6 alkoxy, C3–C6 branched alkoxy, C3–C6 cycloalkoxy, phenoxy, benzyloxy, C2–C6 alkenyloxy, C2–C6 alkynyloxy, C1–C6 haloalkoxy, silyloxy, (C1–C6 alkoxy)-carbonylmethoxy, C1–C6 thioalkoxy, C1–C6 alkylamino, C1–C6 alkyl, C3–C6 branched alkyl, (C1–C6 alkoxy) C1–C6 alkoxy, or (C1–C6 alkoxy)carbonyl;
• R2 and R3 are each, independently, hydrogen, halogen, C1–C6 alkyl, C3–C6 branched alkyl, C1–C6 haloalkyl, C1–C6 alkoxy, C1–C6 haloalkoxy, cyano, or (C1–C6 alkoxy)carbonyl;
• R4 is C1–C6 alkyl;
• and
• Z1 and Z2 are each independently, carbon or nitrogen,
• with the proviso that when Z1 is carbon, X is oxygen, and R2 is hydrogen, then R3 cannot be hydrogen;
• or
• b)
• wherein R5 is C1–C6 alkoxy;
• and R6 and R6 are, independently, halo or C1–C6 haloalkyl.

A phenoxyphenylhydrazine compound of the formula:

• wherein
• Q is —NY—NH—, —N═N—, or
• X is sulfur;
• n is 1;
• Y is hydrogen, C1–C4 alkanoyl, C1–C4 haloalkanoyl, C1–C6 straight chain or branched alkoxycarbonyl, C1–C4 alkoxy(C1–C4)alkoxycarbonyl, C1–C4 alkyl, or C1–C4 haloalkyl;
• R1is C1–C6 alkoxy, C3–C6 branched alkoxy, C3–C6 cycloalkoxy, phenoxy, benzyloxy, C2–C6 alkenyloxy, C2–C6 alkynyloxy, C1–C6 haloalkoxy, silyloxy, (C6–C6 alkoxy)-carbonylmethoxy, C1–C6 thioalkoxy, C1–C6 alkylamino, (C1–C6 alkoxy) C1–C6 alkoxy, or (C1–C6 alkoxy)carbonyl;
• R2 and R3 are each, independently, hydrogen, halogen, C1–C6 haloalkyl, C1–C6 alkoxy, C1–C6 haloalkoxy, cyano, or (C1–C6 alkoxy)carbonyl;
• R4 is C1–C6 alkyl;
• and
• Z1 and Z2 are each independently, carbon or nitrogen.

A phenoxyphenylhydrazine compound of the formula:

• wherein
• Q is —NY—NH—, —N═N—, or
• n is 0;
• Y is hydrogen, C1–C4 alkanoyl, C1–C4 haloalkanoyl, C1–C4 alkyl, or C1–C4 haloalkyl;
• R1is C1–C6 alkoxy, C3–C6 branched alkoxy, C3–C6 cycloalkoxy, phenoxy, benzyloxy, or C2–C6 alkynyloxy;
• R2 and R3 are each, independently, hydrogen, halogen, C1–C6 haloalkyl, C1–C6 alkyl, or C1–C6 alkoxy;
• R4 is C1–C6 alkyl;
• and
• Z1 and Z2 are carbon.