IP Library Granted Patent US 8,449,898
Granted Patent B2
US 8,449,898 · App. 12/679,361 · Granted May 28, 2013

Fungicidal mixtures

Inventors: Vann Gregory (Newark, DE); Robert James Pasteris (Newark, DE); Mary Ann Hanagan (Newark, DE)
Assignee: E I du Pont de Nemours and Company
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Quick Facts
Patent No.
US 8,449,898
App. No.
12/679,361
Granted
May 28, 2013
Kind
B2
Abstract

Disclosed is a fungicidal composition comprising (a) at least one compound selected from the compounds of Formula 1 N-oxides, and salts thereof, wherein R 1 , R 2 , A, G, W, Z 1 , X, J, 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 the aforesaid composition. Also disclosed is a composition comprising component (a) of aforesaid composition and at least one insecticide. Also disclosed are compounds of Formula 1A, 1B and 1C, wherein R 1 , R 2 , A, G, W, Z 1 , X, J, n, Z 3 , M and J 1 are as defined in the disclosure.

Claims (166)

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

each R 4a is independently C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, halogen, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy;

each R 4b is independently C 1 -C 2 alkyl or C 1 C 2 haloalkyl;

A is CH 2 or NH;

W is O;

X is a radical selected from

wherein the bond of X 1 or X 3 , which is identified with “t” is connected to the carbon atom identified with “q” of Formula 1, the bond which is identified with “u” is connected to the carbon atom identified with “r” of Formula 1, and the bond which is identified with “v” is connected to G;

each R 2 is independently methyl, methoxy, cyano or hydroxy;

G is

wherein the bond projecting to the left is bonded to X, and the bond projecting to the right is bonded to Z 1 ; each R 3a is independently selected from H or R 3 ;

each R 3 is independently methyl or halogen;

J is

wherein the bond shown projecting to the left is bonded to Z 1

each R 5 is independently H, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 2 -C 6 alkoxalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 alkoxyaloxy, C 2 -C 6 alkylcarbonloxy, C 2 -C 6 haloalkylcarbonyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloakylthio, C 3 -C 10 trialkylsilyl, —NR 25 R 26 or Z 2 Q;

each R 25 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl or C 2 -C 6 haloalkoxycarbonyl;

each R 26 is independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkoxycarbonyl or —Z 4 Q;

Q is one of Q-1 through Q-102

each R 7 is independently halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, hydroxy, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy; or

each R 12 is independently H, C 1 -C 3 alkyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl or C 1 -C 3 alkoxy;

Z 1 is a direct bond;

Z 2 is a direct bond or NR 21 ;

each Z 4 is C(═O);

each R 21 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl or C 2 -C 6 haloalkoxycarbonyl;

k is 1 or 2;

x is an integer from 0 to 5;

p is 0, 1, 2, or 3; and

n is 0, and

(b) at least one additional fungicidal compound;

provided that:

(i) when R 4 is attached to a carbon ring member, said R 4 is selected from R 4a ; and

(ii) when R 4 is attached to a nitrogen ring member, said. R 4 is selected from R 4b .

2. The composition of claim 1 wherein component (a) is a compound of Formula 1 or a salt thereof, wherein

A is CH 2 ;

G is selected from G-1, G-2, G-15, G-26, G-27, G-36, G-37 and G-38; and G is unsubstituted;

J is selected from J-4, J-5, J-8, J-11, J-15, J-16, J-20, J-29, J-30, J-37, J-38, and J-69;

Q is selected from Q-1, Q-45, Q-63, Q-64, Q-65, Q-68, Q-69, Q-70, Q-71, Q-72, Q-73, Q-76, Q-78, Q-79, Q-84, Q-85, Q-98, Q-99, Q-100, Q-101 and Q-102;

X is X 1 and the ring comprising X is saturated;

R 1 is U-1 or U-50;

each R 4a is independently C 1 -C 2 alkyl, trifluoromethyl, Cl, Br, I or methoxy;

each R 4b is independently C 1 -C 2 alkyl or trifluoromethyl; and

each R 5 is independently H, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, —NR 25 R 26 or Z 2 Q.

3. The composition of claim 2 wherein component (a) is a compound of Formula 1 or a salt thereof, wherein

G is selected from G-1, G-2, G-15, G-26 and G-36;

J is selected from J-4, J-5, J-11, J-20, J-29, J-37, J-38, and J-69; and

Q is selected from Q-45, Q-63, Q-64, Q-65, Q-68, Q-69, Q-70, Q-71, Q-72 and Q-85.

4. The composition of claim 1 wherein component (a) is selected from the group consisting of

4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]piperidine and its enantiomer,

1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-[4-(5-phenyl-3-isoxazolyl)-2-thiazolyl]piperidine,

1-[4-[4-[(5R)-4,5-dihydro-5-methyl-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-[4-[4-[(3aS,9bR), 3a,4,5,9b-tetrahydronaphth[2,1-d]isoxazol-3-yl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,

1-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-ethyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

2-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]-1-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,

1-[4-[4-[(5R)-3′,4′-dihydrospiro[isoxazole-5(4H),1′,(2′H)-naphthalen]-3-yl]-2-thiazolyl]-1-piperidinyl]-2[-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

1-[4-[4-[(5R)-2,3-dihydrospiro[1H-indene-1,5′(4′H )-isoxazol]-3′-yl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

2-[5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazoly]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,

2-[(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl-5-isoxazolyl]-1H-isoindole-1,3(2H)-dione and its enantiomer,

2-[5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-[4-[4-[(1R)-2,3-dihydrospiro[1H-indene-1,5′(4′H)-isoxazol]-3′-yl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,

2-[5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-[4-[4-[(1′R)-3′,4′-dihydrospiro[isoxazole-5(4H),1′(2H )-naphthalen]-3-yl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,

2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-[4-[4-(3R)-spiro[benzofuran-3(2H),5′(4′H)-isoxazol]-3′-yl-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,

1-[4-[4-[(1R)-2,3-dihydrospiro[1H-indene-1,5′(4′H)-isoxazol]-3′-yl]-2-thiazolyl]-1-piperidinyl-2-(3,5-dimethyl-1H-pyrazol-1-yl)ethatione and its enantiomer,

2-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]-1-[4-[4-[(1′R)-3′,4′-dihydrospiro[isoxazole-5(4H ),1′(2H )-naphthalen]-3-yl]-2-thiazolyl]-1-piperidinyl]ethatione and its enantiomer,

2-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]-1-[4-[4-[(1R)-2,3-dihydrospiro[1H-indene-1,5′(4′H)-isoxazol]-3′-yl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,

1-[4-[4-[(5R)-5-(2,6-dichlorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

1-[4-[4-[(5R)-4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluorornethyl)-1H-pyrazol-1-yl]etharione and its enantiomer,

1-[4-[4-[(5R)-4,5-dihydro-5-(2-methylphenyl)-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

1-[4-[4-[(5R)-5-(2,6-dimethylphenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

1-[4-[4-[(5R)-4,5-dihydro-5-(2,4,6-trimethylphenyl)-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

1-[4-[4-[(1′R)-3′,4′-dihydrospiro[isoxazole-5(4H),1′(2′)-naphthalen]-3-yl]-2-thiazolyl]-1-piperidinyl]-2-(3,5-dimethyl-1H-pyrazol-1-yl)ethanone and its enantiomer,

1-[4-[4-[(5R)-4,5-dihydro-5-(2,4,6-trimethoxyphenyl)-3-isoxazolyl]-2-thiazoly]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

3-[(5R)-4,5-dihydro-3-2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-5-isoxazoly]-2(3H)-benzoxazolone and its enantiomer,

1-[4-[4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

2-[(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-5-isoxazolyl]benzonitrile and its enantiomer,

2-[5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-[4-[4-[(5R)-4,5-dihydro-5-methyl-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,

2-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]-1-[4-[4-[(5R)-4,5-dihydro-5-methyl-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,

1-[4-[4-[(5R)-5-(2-ehlorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazoly]-1-piperidinyl]-2-[5-methyl-3-(trilluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

1-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazoly]-1-piperidinyl]-2-[3-methyl-5-(tritluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

1-[4-[4-[(4S)-2,3-dihydrospiro[4H-1-benzopyran-4,5′(4′H)-isoxazol]-3′-yl)-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-5-phenyl-5-isoxazolecarbonitrile and its enantiomer,

1-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

1-[(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(triflnoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-5-isoxazolyl]-1,3-dihydro-3-methyl-2H-benzimidazol-2-one and its enantiomer,

N-[(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-5-isoxazolyl]-N-phenylacetamide and its enantiomer,

4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazoly]-N-(2,5-dimethylphenyl)-1-piperidineearboxamide and its enantiomer,

3-[(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-5-isoxazolyl]-2(3H)-benzothiazolone and its enantiomer,

1-acetyl-3-[(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-5-isoxazolyl]-1,3-dihydro-2H-benzimidazol-2-one and its enantiomer,

4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-N-[5-methyl-3-(trifluoromethyl)-1H-pyrazolyl-1-yl]-1-piperidinecarboxamide and its enantiomer, and

1-[4-[4-[(5R)-5-(2-bromophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer.

5. The composition of claim 1 wherein component (a) is 4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]piperidine, its enantiomer or a mixture thereof.

6. The composition of claim 1 wherein component (a) is 1-[4-[4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, its enantiomer or a mixture thereof.

7. The composition of claim 1 wherein component (b) includes at least one compound selected from the group consisting of

(b1) methyl benzimidazole carbamate fungicides;

(b2) dicarboximide fungicides;

(b3) demethylation inhibitor 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 fungicides;

(b12) phenylpyrrole fungicides;

(b13) quinoline fungicides;

(b14) lipid peroxidation inhibitor fungicides;

(b15) melanin biosynthesis inhibitors-reductase fungicides;

(b16) melanin biosynthesis inhibitors-dehydratase fungicides;

(b17) hydroxyanilide fungicides;

(b18) squalene-epoxidase inhibitor fungicides;

(b19) polyoxin fungicides;

(b20) phenylurea fungicides;

(b21) quinone inside inhibitor 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 fungicides;

(b41) tetracycline antibiotic fungicides;

(b42) thioearbamate fungicides;

(b43) benzamide fungicides;

(b44) host plant defense induction fungicides;

(b45) multi-site contact activity fungicides; and

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

8. The composition of claim 1 further comprising at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent.

9. The composition of claim 1 wherein weight ratio of component (a) to component (b) is from about 125:1 to about 1:125.

10. The composition of claim 1 wherein component (a) is selected from the group consisting of

4-[4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazoly]-N-(2,5-dimethylphenyl)-1-piperidinecarboxamide and its enantiomer,

2-(3,5-dimethyl-1H-pyrazol-1-yl)-1-[4-[4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazoly]-2-thiazoly]-1-piperidinyl]ethanone and its enantiomer,

2-(2,5-dimethylphenyl)-1-[4-[4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]ehanone and its enantiomer, and

1-[4-[4-[(5R)-4,5-dihydro-5-[2-(trifluoromethyl)phenyl]-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer.

11. The composition of claim 1 wherein component (a) is selected from the group consisting of

2-[3,5-bis(trifluorornethyl)-1H-pyrazol-1-yl]-1-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,

1-[4-[4-[(5R)-3′,4′-dihydrospiro[isoxazole-5(4H),1′,(2′H)-naphthalen]-3-yl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

1-[4-[4-[(5R)-2,3-dihydrospiro[1H-indene-1,5′(4′H)-isoxazol]-3′-yl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

2-[(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl-5-isoxazolyl]-1H-isoindole-1,3(2H)-dione and its enantiomer,

1-[4-[4-[(5R)-4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl]-2-thiazoly]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

1-[4-[4-[(5R)-5-(2,6-dimethylphenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

3-[(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-5-isoxazolyl]-2(3H)-benzoxazolone and its enantiomer,

1-[4-[4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

2-[(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-5-isoxazolyl]benzonitrile and its enantiomer,

(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazoly]-5-phenyl-5-isoxazolecarbonitrile and its enantiomer,

1-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-N-(2,5-dimethylphenyl)-1-piperidinecarboxamide and its enantiomer,

1-[4-[4-[(5R)-4,5-dihydro-5-[2-(trifluoromethyl)phenyl]-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone and its enantiomer,

1-[4-[4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-(3,5-dimethyl-1H-pyrazol-1-yl]ethanone and its enantiomer,

[4-[4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-N-(2,5-dimethylphenyl)-1-piperidinecarboxamide and its enantiomer,

1-[4-[4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-(2,5-dimethylphenyl)ethanone and its enantiomer and

1-[4-[4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-(2,5-dimethylphenyl)-2-hydroxy-ethanone and its enantiomer.

12. The composition of claim 1 wherein component (b) includes at least one compound selected from acibenzolar-S-methyl, aldimorph, amisulbrom, anilazine, azaconazole, azoxystrobin, benalaxyl, benalaxyl-M, benodanil, benomyl, benthiavalicarb, benthiavalicarb-isopropyl, bethoxazin, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), boscalid, brornuconazole, bupirimate, captafol, captan, carbendazim, carboxin, carpropamid, chloroneb, chlorothalonil, chlozolinate, clotrimazole, copper oxychloride, copper salts such as copper sulfate and copper hydroxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dichlolluanid, diclocyrnet, diclomezine, dicloran, diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole M, dinocap, dithianon, dodemorph, dodine, edifenphos, enestroburin, epoxiconazole, ethaboxam, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, feripiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin chloride, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorph, fluopicolide, fluopyram, fluoromide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, folpet, fosetyl-aluminum, fuberidazole, furalaxyl, furametpyr, guazatine, hexaconazole, hymexazol, imazalil, imibenconazole, iodocarb, ipconazole, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isotianil, kasugamycin, kresoxim-methyl, mancozeb, mandipropamid, maneb, mefenoxam, mepanipyrim, mepronil, meptyldinocap, metalaxyl, metalaxyl-M, metconazole, methasulfocarb, metiram, metominostrobin, metrafenone, myclobutanil, naftifine, neo-asozin (ferric methanearsonate), nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxolinic acid, oxpoconazole, oxycarboxin, oxytetracycline, pefurazoate, penconazole, pencycuron, penthiopyrad, phosphorous acid and salts, phthalide, picoxystrobin, piperalin, polyoxin, probenazole, prochloraz, procymidone, propamocarb, propamocarb-hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyroquilon, pyrrolnitrin, quinmethionate, quinoxyfen, quintozene, silthiofam, simeconazole, spiroxamine, streptomycin, sulfur, tebuconazole, tecloftalam, tecnazene, terbinafine, tetraconazole, thiabendazole, thifluzamide, thiophanate, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrohin, triflumizole, triforine, trimorphamide, triticonazole, uniconazole, validamycin, valiphenal, vinclozolin, zineb, ziram, zoxamide, 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine, N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dirnethyl-1H-pyrazol-4-carboxamide, N-[2-4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)amino]butanarnide, N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(ethylsulfonyl)aminol]butanamide, 2-butoxy-6-iodo-3-propyl-4H-1-benzopyran-4-one, 3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl]pyridine, 4-fluorophenyl N-[1-[[[1-(4-cyanophenyl)ethyl]sulfonyl]methyl]propyl]carbamate, N-[[(cyclopropylmethoxy)amino][6-(difluoromethoxy)-2,3-difluorophenyl]methylene]benzeneacetamide, α-[methoxyimino]-N-methyl-2-[[[1-[3-(trifluoromethyl)phenyl]ethoxy]imino]methyl]benzeneacetamide, N-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide, N-[2-(1S,2R)-[1,1′-bicyclopropyl]-2-ylphenyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide and N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide.

13. The composition of claim 1 wherein component (b) includes at least one compound selected from azoxystrobin, benthiavalicarb, boscalid, chlorothalonil, copper hydroxide, cyazofamid, cymoxanil, dimethomorph, ethaboxam, famoxadone, fenamidone, fluazinam, fluopicolide, folpet, fosetyl-aluminum, iprovalicarb, kresoxim-methyl, mancozeb, mandipropamid, mefenoxarn, penthiopyrad, propamocarb, proquinazid, pyraclostrobin, quinoxyfen, trifloxystrobin, valiphenal and 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine.

14. A method for controlling a plant disease caused by a fungal plant pathogen comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of the composition of claim 1 .

Assignments (2)
NUNC PRO TUNC ASSIGNMENT Recorded Nov 29, 2022
From: E.I. DU PONT DE NEMOURS AND COMPANY
To: CORTEVA AGRISCIENCE LLC
Reel/Frame 063141/0155 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2012
From: GREGORY, VANN; HANAGAN, MARY ANN; PASTERIS, ROBERT JAMES
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 029495/0681 →
Continuity (3)
Provisional Application 61000002 · Oct 23, 2007
Provisional Application 61062400 · Jan 25, 2008
Related Publication 20100240619A1 · Sep 23, 2010