Fungicidal mixtures containing pyrazole derivatives

Patent metadata

Field	Value
Publication number	US-2023148599-A1
Application number	US-202117910051-A
Country	US
Kind code	A1
Filing date	Mar 11, 2021
Priority date	Mar 11, 2020
Publication date	May 18, 2023
Grant date	—

Abstract

Disclosed is a fungicidal composition comprising (a) at least one compound selected from the compounds of Formula 1, including all geometric and stereoisomers, tautomers, iV-oxides, and salts thereof, (I) wherein R1, R2, R3, R4, R5, R6, m and n are as defined in the disclosure and (b) at least one additional fungicidal compound. Also disclosed is 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 Formula 1, an A-oxide, or salt thereof (e.g., as a component in the aforesaid composition). Also disclosed is a composition comprising: (a) at least one compound selected from the compounds of Formula 1 described above, A-oxides, and salts thereof; and at least one invertebrate pest control compound or agent.

First claim

What is claimed is:

1 . 1. A fungicidal composition comprising:
(a) at least one compound selected from the compounds of Formula 1, N-oxides, and salts thereof:

wherein
R 1 is C 1 -C 2 alkyl;
R 2 is cyano, halogen, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;
R 3 is halogen or methyl;
each R 4 is independently halogen, cyano, nitro, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 cyanoalkoxy, C 2 -C 6 alkoxyalkyl or C 2 -C 6 alkoxyalkoxy;
each R 5 is independently halogen, C 1 -C 3 alkyl, C 2 -C 6 alkoxyalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 cyanoalkoxy or C 2 -C 6 alkoxyalkoxy;
m and n are each independently 0, 1, 2 or 3;
R 6 is H; or C 1 -C 3 alkyl or C 1 -C 3 haloalkyl, each optionally substituted with up to 2 substituents independently selected from R 6a ; or amino, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, CH(═O), S(═O) 2 OM, S(═O) u R 7 , (C═W)R 8 or OR 9 ;
each R 6a is independently cyano, C 3 -C 6 cycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl or C 1 -C 3 alkylsulfonyl;
M is K or Na;
u is 0, 1 or 2;
R 7 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
W is O or S;
R 8 is C 1 -C 3 alkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylaminoalkyl, C 3 -C 6 dialkylaminoalkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio or C 2 -C 4 alkylthioalkyl;
R 9 is H; or C 1 -C 3 alkyl or C 1 -C 3 haloalkyl, each optionally substituted with up to 2 substituents independently selected from R 9a ; or CH(═O), C 3 -C 6 cycloalkyl, S(═O) 2 OM or (C═W)R 10 ;
each R 9a is independently cyano, C 3 -C 6 cycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl or C 1 -C 3 alkylsulfonyl; and
R 10 is C 1 -C 3 alkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylaminoalkyl, C 3 -C 6 dialkylaminoalkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio or C 2 -C 4 alkylthioalkyl; and

(b) at least one additional fungicidal compound;
provided that the compound of Formula 1 is not:
4-(2,6-difluoro-4-methoxyphenyl)-N-(2,4-difluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-N-(2-nitrophenyl)-1H-pyrazol-5-amine;
4-(2-chloro-4-fluorophenyl)-N-(2,4-difluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
4-(2-chloro-4-fluorophenyl)-3-ethyl-1-methyl-N-(2-nitrophenyl)-1H-pyrazol-5-amine;
4-(2-chloro-4-fluorophenyl)-1-methyl-N-(2-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-amine;
4-(2,6-difluoro-4-methoxyphenyl)-N-(2-methoxy-6-nitrophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
4-(2-chloro-4-fluorophenyl)-N-(2-methoxy-6-nitrophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
N-(2-chloro-6-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
N-(2-chloro-3-fluoro-6-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-N-(2-methyl-6-nitrophenyl)-1H-pyrazol-5-amine;
N-(2-bromo-4-fluoro-6-nitrophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
4-(2-chloro-4-fluorophenyl)-N-(4-methoxy-2-nitrophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
4-(2,6-difluoro-4-methoxyphenyl)-N-(4-fluoro-2-nitrophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
4-(2,6-difluoro-4-methoxyphenyl)-N-(4-methoxy-2-nitrophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
N-(4-chloro-2-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-[2-nitro-4-(2-propyn-1-yloxy) phenyl]-1H-pyrazol-5-amine;
4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-[2-nitro-4-(2-propen-1-yloxy) phenyl]-1H-pyrazol-5-amine;
N-(4-bromo-2-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
N-(4-chloro-2-fluoro-6-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazol-5-amine;
3-chloro-4-(2-chloro-4-fluorophenyl)-N-(2,4-difluoro-6-nitrophenyl)-1-methyl-1H-pyrazol-5-amine;
4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-[4-methyl-2-nitrophenyl]-1H-pyrazol-5-amine;
4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-N-(4-methyl-2-nitrophenyl)-1H-pyrazol-5-amine; and
N-(4-bromo-2-fluoro-6-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

2 . The composition of claim 1 wherein component (a) comprises a compound of Formula 1 or salt thereof, wherein
R 1 is methyl;
R 2 is cyano, halogen or C 1 -C 2 alkyl;
R 3 is halogen;
each R 4 is independently halogen, cyano, methyl, methoxy, halomethoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy or C 2 -C 4 cyanoalkoxy;
each R 5 is independently halogen, methyl, methoxy, halomethoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy or C 2 -C 4 cyanoalkoxy;
R 6 is H; or C 1 -C 2 alkyl or C 1 -C 2 haloalkyl, each optionally substituted with up to 1 substituent selected from R 6a ; or S(═O) u R 7 or OR 9 ;
R 6a is cyano, C 3 -C 6 cycloalkyl or C 1 -C 3 alkoxy;
R 7 is methyl or halomethyl;
R 9 is H; or C 1 -C 2 alkyl or C 1 -C 2 haloalkyl, each optionally substituted with up to 1 substituent selected from R 9a ; and
R 9a is cyano, C 3 -C 6 cycloalkyl or C 1 -C 3 alkoxy.

3 . The composition of claim 2 wherein component (a) comprises a compound of Formula 1 or salt thereof, wherein
R 2 is methyl or ethyl;
R 3 is Br, Cl or F;
each R 4 is independently halogen, cyano, methyl or methoxy;
m is 1 and R 4 is at the para position; or m is 1 and R 4 is at the ortho position; or m is 2 and one R 4 is at the para position, and the other is at the ortho position;
each R 5 is independently halogen, methyl or methoxy;
n is 1 and R 5 is at the para position; or n is 1 and R 5 is at the ortho position; or n is 2 and one R 5 is at the para position, and the other is at the ortho position; and
R 6 is H or methyl.

4 . The composition of claim 3 wherein component (a) comprises a compound of Formula 1 or salt thereof, wherein
R 2 is methyl;
each R 4 is independently Br, Cl, F, cyano or methoxy;
each R 5 is independently Br, Cl, F, methyl or methoxy; and
R 6 is H.

5 . The composition of claim 4 wherein component (a) comprises a compound of Formula 1 or salt thereof, wherein
each R 4 is independently Br, Cl or F; and
m and n are each 1 and R 4 is at the para position and R 5 is at the ortho position; or m is 1 and R 4 is at the para position, and n is 2 and one R 5 is at the para position and the other is at the ortho position; or m is 2 and one R 4 is at the para position and the other is at the ortho position, and n is 1 and R 5 is at the ortho position.

6 . The composition of claim 5 wherein component (a) comprises a compound of Formula 1 or salt thereof, wherein
R 4 is Cl or F;
each R 5 is independently Cl, F or methyl; and
m and n are each 1 and R 4 is at the para position and R 5 is at the ortho position; or m is 1 and R 4 is at the para position, and n is 2 and one R 5 is at the para position and the other is at the ortho position.

7 . The composition of claim 1 wherein component (a) comprises a compound of Formula 1 or salt thereof, wherein
R 1 is methyl;
R 2 is methyl or ethyl;
R 3 is halogen;
each R 4 is independently Br, Cl, F, cyano or methoxy;
m is 1 and R 4 is at the para position; or m is 1 and R 4 is at the ortho position; or m is 2 and one R 4 is at the para position, and the other is at the ortho pos

Assignees

• Fmc Corp

Inventors

• Long Jeffrey Keith
• Chittaboina Srinivas
• Mcmahon Travis Chandler

Classifications

• C07D231/38 Primary

  Nitrogen atoms (nitro radicals C07D231/16) · CPC title

• A01N43/56 Primary

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title

• A01P3/00

  Fungicides · CPC title

• A01C1/06

  Coating or dressing seed · CPC title

• A01G13/00

  Protection of plants (greenhouses A01G9/14) · CPC title