Fungicidal oxadiazoles
Disclosed are compounds of Formula 1, including all geometric and stereoisomers, tautomers, N-oxides, and salts thereof, wherein R 1 , Z 1 , W, Z 2 and J are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.
1. A compound selected from Formula 1, N-oxides, and salts thereof,
wherein R 1 is H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 2 -C 4 alkylcarbonyl or C 2 -C 4 alkoxycarbonyl; or U-50
wherein R 3 is selected from R 3a ; and k is 0, 1 or 2;
Z 1 is —(CH 2 ) n NR 4a , wherein the bond projecting to the left is attached to R 1 , and the bond projecting to the right is attached to C=W;
W is O or S;
Z 2 is —O(CH 2 )m-, —OCH 2 CH 2 O- or —NR 5 N═CH-, wherein the bond projecting to the left is attached to C=W, and the bond projecting to the right is attached to J;
J is
wherein the bond projecting to the left is bonded to Z 2 , and the bond projecting to the right is bonded to the oxadiazole ring in Formula 1; and each R 7a is H;
each R 3a is independently methyl, C 2 -C 4 alkylcarbonyl or C 2 -C 4 alkoxycarbonyl;
R 4a is H;
R 5 is H;
n is 0; and
m is 1,2 or 3;
provided that:
(b) the compound of Formula 1 is not:
[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl N-methylcarbamate;
[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl N-ethylcarbamate;
[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl N-propylcarbamate;
[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl N-(1-methylethyl)carbamate;
[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl N-(2-methylpropyl)carbamate; and
[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl N-butylcarbamate.
2. A compound of claim 1 wherein:
Z 2 is —O(CH 2 ) m —;
W is O;
J is J-50; and
m is 1 or 2.
3. A compound which is selected from the group:
[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-
yl]phenyl]methyl carbamate (Compound 17);
2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-
3-yl]phenyl]ethyl N-ethylcarbamate
(Compound 43); and
methyl 2-[[4-[5-(trifluoromethyl)-1,2,4-
oxadiazol-3-yl]phenyl]methylene]-
hydrazinecarboxylate (Compound 105).
4. A fungicidal composition comprising (a) a compound of claim 1 ; and (b) at least one other fungicide.
5. A fungicidal composition comprising (a) a compound of claim 1 ; and (b) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.
6. A method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of a compound of claim 1 .
7. A method for controlling plant diseases caused by Basidiomycetes fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of a compound of claim 1 .
8. A compound of claim 1 which is selected from:
wherein
R 1 is CH≡CCH 2 and Z 2 is OCH 2 ; or
R 1 is H and Z 2 is OCH 2 ; or
R 1 is CH≡CCH 2 CH 2 and Z 2 is OCH 2 ; or
R 1 is CH 3 CCCH 2 and Z 2 is OCH 2 ; or
R 1 is H and Z 2 is OCH 2 CH 2 ; or
R 1 is CH 3 and Z 2 is OCH 2 CH 2 ; or
R 1 is CH 3 CH 2 and Z 2 is OCH 2 CH 2 ; or
R 1 is CH≡CCH 2 and Z 2 is OCH 2 CH 2 ; or
R 1 is CH 2 =CHCH 2 and Z 2 is OCH 2 ; or
R 1 is CH 3 C≡CCH 2 and Z 2 is OCH 2 CH 2 ; or
R 1 is CH 3 C≡CCH 2 and Z 2 is OCH 2 CH 2 CH 2 ; or
R 1 is CH≡CCH 2 CH 2 and Z 2 is OCH 2 CH 2 CH 2 ; or
R 1 is CH≡CCH 2 CH 2 and Z 2 is OCH 2 CH 2 ; or
R 1 is CH 3 CH 2 OC(=O) and Z 2 is OCH 2 CH 2 ; or
R 1 is CH 3 CH 2 OC(=O) and Z 2 is OCH 2 .
9. A compound of claim 1 which is selected from:
wherein
R 1 is CH 3 , CH 3 CH 2 , CH 3 CH 2 CH 2 or CH≡CCH 2 .