Fungicidal 4-methylanilino pyrazoles

1. A compound selected from Formula 1, N-oxides and salts thereof,

wherein

R 1 is F, Cl or Br;

R 2 is H, F, Cl or Br; and

R 3 is F, Cl or Br.

2. A compound of claim 1 wherein:

R 1 is F or Cl; and

R 2 is F, Cl or Br.

3. The compound of claim 1 which is selected from the group:

N-(2-bromo-6-fluoro-4-methylphenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-chloro-4-fluorophenyl)-N-(2-chloro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-bromo-4-methylphenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-bromo-4-fluorophenyl)-N-(2-chloro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-bromo-4-fluorophenyl)-N-(2-bromo-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-bromo-6-fluoro-4-methylphenyl)-4-(2-bromo-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-bromo-6-fluoro-4-methylphenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2,6-difluoro-4-methylphenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-chloro-4-fluorophenyl)-N-(2,6-difluoro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluoro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine and

N-(2-chloro-6-fluoro-4-methylphenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

4. The compound of claim 1 which is selected from the group:

N-(2-bromo-6-fluoro-4-methylphenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-chloro-4-fluorophenyl)-N-(2-chloro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-bromo-4-methylphenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-bromo-4-fluorophenyl)-N-(2-chloro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-bromo-4-fluorophenyl)-N-(2-bromo-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-bromo-6-fluoro-4-methylphenyl)-4-(2-bromo-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-bromo-6-fluoro-4-methylphenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2,6-difluoro-4-methylphenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-chloro-4-fluorophenyl)-N-(2,6-difluoro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluoro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

N-(2-chloro-6-fluoro-4-methylphenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-chloro-4-fluorophenyl)-N-(2,6-dichloro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-bromo-4-fluorophenyl)-N-(2,6-difluoro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine,

4-(2-bromo-4-fluorophenyl)-N-(2,6-dichloro-4-methylphenyl)-1,3-dimethyl-1H-pyrazol-5-amine and

N-(2,6-dichloro-4-methylphenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

5. A fungicidal composition comprising (a) a compound of claim 1 ; and (b) at least one other fungicide.

6. The fungicidal composition of claim 5 wherein component (b) comprises at least one fungicidal compound selected from the group consisting of

(b1) methyl benzimidazole carbamate (MBC) fungicides;

(b2) dicarboximide fungicides;

(b3) demethylation inhibitor (DMI) fungicides;

(b4) phenylamide fungicides;

(b5) amine/morpholine fungicides;

(b6) phospholipid biosynthesis inhibitor fungicides;

(b7) carboxamide fungicides;

(b8) hydroxy(2-amino-)pyrimidine fungicides;

(b9) anilinopyrimidine fungicides;

(b10) N-phenyl carbamate fungicides;

(b11) quinone outside inhibitor (QoI) fungicides;

(b12) phenylpyrrole fungicides;

(b13) quinoline fungicides;

(b14) lipid peroxidation inhibitor fungicides;

(b15) melanin biosynthesis inhibitors-reductase (MBI-R) fungicides;

(b16) melanin biosynthesis inhibitors-dehydratase (MBI-D) fungicides;

(b17) hydroxyanilide fungicides;

(b18) squalene-epoxidase inhibitor fungicides;

(b19) polyoxin fungicides;

(b20) phenylurea fungicides;

(b21) quinone inside inhibitor (QiI) fungicides;

(b22) benzamide fungicides;

(b23) enopyranuronic acid antibiotic fungicides;

(b24) hexopyranosyl antibiotic fungicides;

(b25) glucopyranosyl antibiotic: protein synthesis fungicides;

(b26) glucopyranosyl antibiotic: trehalase and inositol biosynthesis fungicides;

(b27) cyanoacetamideoxime fungicides;

(b28) carbamate fungicides;

(b29) oxidative phosphorylation uncoupling fungicides;

(b30) organo tin fungicides;

(b31) carboxylic acid fungicides;

(b32) heteroaromatic fungicides;

(b33) phosphonate fungicides;

(b34) phthalamic acid fungicides;

(b35) benzotriazine fungicides;

(b36) benzene-sulfonamide fungicides;

(b37) pyridazinone fungicides;

(b38) thiophene-carboxamide fungicides;

(b39) pyrimidinamide fungicides;

(b40) carboxylic acid amide (CAA) fungicides;

(b41) tetracycline antibiotic fungicides;

(b42) thiocarbamate fungicides;

(b43) benzamide fungicides;

(b44) host plant defense induction fungicides;

(b45) multi-site contact activity fungicides;

(b46) fungicides other than fungicides of component (a) and components (b1) through (b45); and

salts of compounds of (b1) through (b46).

7. A fungicidal composition of claim 6 ; and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

8. 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 .