IP Library Granted Patent US 8,618,137
Granted Patent B2
US 8,618,137 · App. 13/127,809 · Granted Dec 31, 2013

Fungicidal heterocyclic compounds

Inventor: Robert James Pasteris (Newark, DE)
Assignee: E I du Pont de Nemours and Company
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Quick Facts
Patent No.
US 8,618,137
App. No.
13/127,809
Granted
Dec 31, 2013
Kind
B2
Abstract

Disclosed are compounds of Formula 1, including all geometric and stereoisomers, tautomers, N-oxides, and salts thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , A, W, X, G, Z, J and n 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.

Claims (47)

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

wherein

A is —O—,

wherein the bond projecting to the left is connected to the nitrogen atom of Formula 1, and the bond projecting to the right is connected to the carbon atom of Formula 1;

W is O;

G is

Z is a direct bond;

J is

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 of Formula 1;

R 1 is methyl, trifluoromethyl or CF 3 CH 2 ;

R 2 is H, methyl, or trifluoromethyl;

R 3 is H;

R 4 is H;

each R 5 is independently cyano, methyl or methoxy;

R 6 is —Z 2 Q;

Z 2 is a direct bond;

Q is selected from

each R 6a is independently F, Cl, Br, hydroxy, cyano, methyl or methoxy;

each R 6b is independently phenyl optionally substituted with up to 3 substituents independently selected from halogen, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy and C 1 -C 2 haloalkoxy; or

a 5- to 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, the ring optionally substituted with up to 3 substituents independently selected from halogen, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy and C 1 -C 2 haloalkoxy on carbon atom ring members and cyano, C 1 -C 2 alkyl and C 1 -C 2 alkoxy on nitrogen atom ring members; or

a 3- to 7-membered nonaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon atom ring members are independently selected from C(═O) and C(═S), the ring optionally substituted with up to 3 substituents independently selected from halogen, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy and C 1 -C 2 haloalkoxy on carbon atom ring members and cyano, C 1 -C 2 alkyl and C 1 -C 2 alkoxy on nitrogen atom ring members;

R 26 is hydrogen, halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

p is an integer from 0 to 5;

g is an integer from 0 to 1;

each m is independently 0, 1 or 2;

n is 0 or 1; and

x is 1.

2. The compound of claim 1 wherein:

Q is Q-45;

p is 1 or 2; and

each R 6a is F.

3. The compound of claim 1 wherein:

Q is Q-45;

p is 1; and

R 6a is cyano or methyl.

4. A compound of claim 1 selected from the group consisting of:

2-[4,5-dihydro-3-[2-[1-[2-[[(2,2,2-trifluoroethylidene)amino]oxy]acetyl]-4-piperidinyl]-4-thiazolyl]-5-isoxazolyl]benzonitrile;

2,2,2-trifluoroacetaldehyde, O-[2-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-oxoethyl]oxime;

2,2,2-trifluoroacetaldehyde, O-[2-[4-[4-[4,5-dihydro-5-(2-oxo-3(2H)-benzoxazolyl)-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-oxoethyl]oxime;

1,1,1-trifluoro-2-propanone, O-[2-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-oxoethyl]oxime;

2-propanone, O-[2-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-oxoethyl]oxime;

2-[4,5-dihydro-3-[2-[1-[2-[[(2,2,2,-trifluoro-1-methylethylidene)amino]oxy]acetyl]-4-piperidinyl]-4-thiazolyl]-5-isoxazolyl]benzonitrile;

1,1,1-trifluoro-2-propanone, O-[2-[4-[4-[4,5-dihydro-5-(2-oxo-3-(2H)-benzoxazolylidene)-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-oxoethyl]oxime; and

2-propanone, O-[2-[4-[4-[5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,5-dihydro-3-isoxazoly]-2-thiazolyl]-1-piperidinyl]-2-oxoethyl]oxime.

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 Oomycete 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 .

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 Oct 22, 2013
From: PASTERIS, ROBERT JAMES
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 031449/0265 →
Continuity (2)
Provisional Application 61119137 · Dec 2, 2008
Related Publication 20110224258A1 · Sep 15, 2011