Fungicidal phenoxyphenylhydrazine derivatives
View Patent ↗A fungicidally active 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, C 1 –C 4 alkanoyl, C 1 –C 4 haloalkanoyl, C 1 –C 6 straight chain or branched alkoxycarbonyl, C 1 –C 4 alkoxy(C 1 –C 4 )alkoxycarbonyl, C 1 –C 4 alkyl, or C 1 –C 4 haloalkyl; R 1 is C 1 –C 6 alkoxy, C 3 –C 6 branched alkoxy, C 3 –C 6 cycloalkoxy, phenoxy, benzyloxy, C 2 –C 6 alkenyloxy, C 2 –C 6 alkynyloxy, C 1 –C 6 haloalkoxy, silyloxy, (C 1 –C 6 alkoxy)-carbonylmethoxy, C 1 –C 6 thioalkoxy, C 1 –C 6 alkylamino, C 1 –C 6 alkyl, C 3 –C 6 branched alkyl, (C 1 –C 6 alkoxy) C 1 –C 6 alkoxy, or (C 1 –C 6 alkoxy)carbonyl; R 2 and R 3 are each, independently, hydrogen, halogen, C 1 –C 6 alkyl, C 3 –C 6 branched alkyl, C 1 –C 6 haloalkyl, C 1 –C 6 alkoxy, C 1 –C 6 haloalkoxy, cyano, or (C 1 –C 6 alkoxy)carbonyl; R 4 is C 1 –C 6 alkyl; and Z 1 and Z 2 are each independently, carbon or nitrogen, with the proviso that when Z 1 is carbon, X is oxygen, and R 2 is hydrogen, then R 3 cannot be hydrogen; b) wherein R 5 is C 1 –C 6 alkoxy; and R 6 and R 7 are, independently, halo or C 1 –C 6 haloalkyl; or c) wherein R 8 is C 1 –C 6 alkyl; and R 9 and R 10 , independently, are halo or C 1 –C 6 haloalkyl. and a method for controlling fungi using the compound.
1. A phenoxyphenylhydrazine compound of the formula:
a)
wherein
Q is —NY—NH—, —N═N—, or
X is oxygen, sulfoxide, or sulfone;
n is 1;
Y is hydrogen, C 1 –C 4 alkanoyl, C 1 –C 4 haloalkanoyl, C 1 –C 6 straight chain alkoxycarbonyl, C 1 –C 4 alkoxy(C 1 –C 4 )alkoxycarbonyl, C 1 –C 4 alkyl, or C 1 –C 4 haloalkyl;
R 1 is C 1 –C 6 alkoxy, C 3 –C 6 branched alkoxy, C 3 –C 6 cycloalkoxy, phenoxy, benzyloxy, C 2 –C 6 alkenyloxy, C 2 –C 6 alkynyloxy, C 1 –C 6 haloalkoxy, silyloxy, (C 1 –C 6 alkoxy)-carbonylmethoxy, C 1 –C 6 thioalkoxy, C 1 –C 6 alkylamino, C 1 –C 6 alkyl, C 3 –C 6 branched alkyl, or (C 1 –C 6 alkoxy)C 1 –C 6 alkoxy;
R 2 and R 3 are each, independently, hydrogen, halogen, C 1 –C 6 alkyl, C 3 –C 6 branched alkyl, C 1 –C 6 haloalkyl, C 1 –C 6 alkoxy, C 1 –C 6 haloalkoxy, cyano, or (C 1 –C 6 alkoxy)carbonyl;
R 4 is C 1 –C 6 alkyl; and
Z 1 and Z 2 are each independently, carbon or nitrogen,
with the proviso that when Z 1 is carbon, X is oxygen, and R 2 is hydrogen, then R 3 cannot be hydrogen; or
b)
wherein R 5 is C 1 –C 6 alkoxy; and R 6 and R 7 are, independently, halo or C 1 –C 6 haloalkyl.
2. A compound as recited in claim 1 having the formula:
wherein X, n, Y, Z 1 , Z 2 , and R 1 –R 2 are as defined in claim 1 .
3. A compound as recited in claim 1 having the formula:
wherein X, n, Z 1 , Z 2 , and R 1 –R 3 are as defined in claim 1 .
4. A compound as recited in claim 1 having the formula:
wherein X, n, Z 1 , Z 2 , and R 1 R 4 are as defined in claim 1 .
5. A compound as recited in claim 1 having the formula:
wherein R 5 , R 6 , and R 7 are as recited in claim 1 .
6. 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, C 1 –C 4 alkanoyl, C 1 –C 4 haloalkanoyl, C 1 –C 6 straight chain or branched alkoxycarbonyl, C 1 –C 4 alkoxy(C 1 –C 4 )alkoxycarbonyl, C 1 –C 4 alkyl, or C 1 –C 4 haloalkyl;
R 1 is C 1 –C 6 alkoxy, C 3 –C 6 branched alkoxy, C 3 –C 6 cycloalkoxy, phenoxy, benzyloxy, C 2 –C 6 alkenyloxy, C 2 –C 6 alkynyloxy, C 1 –C 6 haloalkoxy, silyloxy, (C 1 –C 6 alkoxy)-carbonylmethoxy, C 1 –C 6 thioalkoxy, C 1 –C 6 alkylamino, C 1 –C 6 alkyl, C 3 –C 6 branched alkyl, (C 1 –C 6 alkoxy)C 1 –C 6 alkoxy, or (C 1 –C 6 alkoxy)carbonyl;
R 2 and R 3 are each, independently, hydrogen, halogen, C 1 –C 6 alkyl, C 3 –C 6 branched alkyl, C 1 –C 6 haloalkyl, C 1 –C 6 alkoxy, C 1 –C 6 haloalkoxy, cyano, or (C 1 –C 6 alkoxy)carbonyl;
R 4 is C 1 –C 6 alkyl; and
Z 1 and Z 2 are each independently, carbon or nitrogen,
with the proviso that when Z 1 is carbon, X is oxygen, and R 2 is hydrogen, then R 3 cannot be hydrogen; or
b)
wherein R 5 is C 1 –C 6 alkoxy; and R 6 and R 7 are, independently, halo or C 1 –C 6 haloalkyl.
7. A method as recited in claim 6 comprising contacting the fungi with a fungicidally effective amount of a compound having the formula:
wherein X, n, Y, Z 1 , Z 2 , and R 1 –R 3 are as defined in claim 6 .
8. A method as recited in claim 4 comprising contacting the fungi with a fungicidally effective amount of a compound having the formula:
wherein X, n, Z 1 , Z 2 , and R 1 –R 3 are as defined in claim 6 .
9. A method as recited in claim 6 comprising contacting the fungi with a fungicidally effective amount of a compound having the formula:
wherein X, n, Z 1 , Z 2 , and R 1 –R 4 are as defined in claim 6 .
10. A method as recited in claim 6 comprising contacting the fungi with a fungicidally effective amount of a compound having the formula:
wherein R 5 , R 6 , and R 7 are as recited in claim 6 .
11. 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, C 1 –C 4 alkanoyl, C 1 –C 4 haloalkanoyl, C 1 –C 6 straight chain or branchd alkoxycarbonyl, C 1 –C 4 alkoxy(C 1 –C 4 )alkoxycarbonyl, C 1 –C 4 alkyl, or C 1 –C 4 haloalkyl;
R 1 is C 1 –C 6 alkoxy, C 3 –C 6 branched alkoxy, C 3 –C 6 cycloalkoxy, phenoxy, benzyloxy, C 2 –C 6 alkenyloxy, C 2 –C 6 alkynyloxy, C 1 –C 6 haloalkoxy, silyloxy, (C 1 –C 6 alkoxy)-carbonylmethoxy, C 1 –C 6 thioalkoxy, C 1 –C 6 alkylamino, C 1 –C 6 alkyl, C 3 –C 6 branched alkyl, (C 1 –C 6 alkoxy) C 1 –C 6 alkoxy, or (C 1 –C 6 alkoxy)carbonyl;
R 2 and R 3 are each, independently, hydrogen, halogen, C 1 –C 6 alkyl, C 3 –C 6 branched alkyl, C 1 –C 6 haloalkyl, C 1 –C 6 alkoxy, C 1 –C 6 haloalkoxy, cyano, or (C 1 –C 6 alkoxy)carbonyl;
R 4 is C 1 –C 6 alkyl; and
Z 1 and Z 2 are each independently, carbon or nitrogen,
with the proviso that when Z 1 is carbon, X is oxygen, and R 2 is hydrogen, then R 3 cannot be hydrogen; or
b)
wherein R 5 is C 1 –C 6 alkoxy; and R 6 and R 6 are, independently, halo or C 1 –C 6 haloalkyl.
12. A phenoxyphenylhydrazine compound of the formula:
wherein
Q is —NY—NH—, —N═N—, or
X is sulfur;
n is 1;
Y is hydrogen, C 1 –C 4 alkanoyl, C 1 –C 4 haloalkanoyl, C 1 –C 6 straight chain or branched alkoxycarbonyl, C 1 –C 4 alkoxy(C 1 –C 4 )alkoxycarbonyl, C 1 –C 4 alkyl, or C 1 –C 4 haloalkyl;
R 1 is C 1 –C 6 alkoxy, C 3 –C 6 branched alkoxy, C 3 –C 6 cycloalkoxy, phenoxy, benzyloxy, C 2 –C 6 alkenyloxy, C 2 –C 6 alkynyloxy, C 1 –C 6 haloalkoxy, silyloxy, (C 6 –C 6 alkoxy)-carbonylmethoxy, C 1 –C 6 thioalkoxy, C 1 –C 6 alkylamino, (C 1 –C 6 alkoxy) C 1 –C 6 alkoxy, or (C 1 –C 6 alkoxy)carbonyl;
R 2 and R 3 are each, independently, hydrogen, halogen, C 1 –C 6 haloalkyl, C 1 –C 6 alkoxy, C 1 –C 6 haloalkoxy, cyano, or (C 1 –C 6 alkoxy)carbonyl;
R 4 is C 1 –C 6 alkyl; and
Z 1 and Z 2 are each independently, carbon or nitrogen.
13. A phenoxyphenylhydrazine compound as recited in claim 12 having the formula:
wherein X, n, Y, Z 1 , Z 2 , and R 1 –R 3 are as defined in claim 12 .
14. A phenoxyphenylhydrazine compound of the formula:
wherein
Q is —NY—NH—, —N═N—, or
n is 0;
Y is hydrogen, C 1 –C 4 alkanoyl, C 1 –C 4 haloalkanoyl, C 1 –C 4 alkyl, or C 1 –C 4 haloalkyl;
R 1 is C 1 –C 6 alkoxy, C 3 –C 6 branched alkoxy, C 3 –C 6 cycloalkoxy, phenoxy, benzyloxy, or C 2 –C 6 alkynyloxy;
R 2 and R 3 are each, independently, hydrogen, halogen, C 1 –C 6 haloalkyl, C 1 –C 6 alkyl, or C 1 –C 6 alkoxy;
R 4 is C 1 –C 6 alkyl; and
Z 1 and Z 2 are carbon.