IP Library › Granted Patent US 8,642,634

Granted Patent B2

US 8,642,634 · App. 12/303,256 · Granted Feb 4, 2014

Fungicidal azocyclic amides

Inventors: 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 8,642,634
App. No.: 12/303,256
Granted: Feb 4, 2014
Kind: B2

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Abstract

Disclosed are compounds of Formulae 1, 1A, 1B and 1C including all geometric and stereoisomers, N-oxides, and salts thereof, wherein R 1 , R 2 , R 4a1 , R 4a2 , A, A a , G, M, W, Z 1 , Z 3 , X, J, J 1 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 (452)

1. A compound selected from Formula 1, an N-oxide and salt thereof,

wherein

R 1 is an optionally substituted phenyl, naphthalenyl or 5- or 6-membered heteroaromatic ring;

A is CHR 15 or NR 16 ;

R 15 is H, halogen, cyano, hydroxy, —CHO, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylthioalkyl, C 2 -C 4 alkylsulfinylalkyl, C 2 -C 4 alkylsulfonylalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 5 alkoxycarbonyl, C 3 -C 5 alkoxycarbonylalkyl, C 2 -C 5 alkylaminocarbonyl, C 3 -C 5 dialkylaminocarbonyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl or C 1 -C 4 haloalkylsulfonyl;

R 16 is H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylthioalkyl, C 2 -C 4 alkylsulfinylalkyl, C 2 -C 4 alkylsulfonylalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 5 alkoxycarbonyl, C 3 -C 5 alkoxycarbonylalkyl, C 2 -C 5 alkylaminocarbonyl, C 3 -C 5 dialkylaminocarbonyl, C 1 -C 4 alkylsulfonyl or C 1 -C 4 haloalkylsulfonyl;

W is O or S;

X is a radical selected from

wherein the bond of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 or X 9 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 C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, halogen, cyano or hydroxy; or

two R 2 are taken together as C 1 -C 4 alkylene or C 2 -C 4 alkenylene to form a bridged bicyclic or fused bicyclic ring system; or

two R 2 attached to adjacent ring carbon atoms joined by a double bond are taken together as —CH═CH—CH═CH— optionally substituted with 1 to 3 substituents selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, halogen, hydroxy, amino, cyano and nitro;

G is an optionally substituted 5-membered heteroaromatic ring or 5-membered saturated or partially saturated heterocyclic ring;

J is a 5-, 6- or 7-membered ring, a 8- to 11-membered bicyclic ring system or a 7- to 11-membered spirocyclic ring system, each ring or ring system containing ring members selected from carbon and optionally 1 to 4 heteroatoms selected from up to 2 O, up to 2 S and up to 4 N, and optionally including 1 to 3 ring members selected from the group consisting of C(═O), C(═S), S(O), S(O) 2 and SiR 17 R 18 , each ring or ring system optionally substituted with 1 to 5 substituents independently selected from R 5 ;

each R 5 is independently H, halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —NR 25 R 26 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 6 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 6 alkylthioalkyl, C 2 -C 6 alkylsulfinylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 alkylaminoalkyl, C 3 -C 8 dialkylaminoalkyl, C 2 -C 6 haloalkylaminoalkyl, C 4 -C 10 cycloalkylaminoalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 4 -C 8 cycloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 4 -C 8 cycloalkoxycarbonyl, C 5 -C 10 cycloalkylalkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 8 dialkylaminocarbonyl, C 4 -C 8 cycloalkylaminocarbonyl, C 2 -C 6 haloalkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 2 -C 6 alkoxyalkoxy, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 haloalkylcarbonyloxy, C 4 -C 8 cycloalkylcarbonyloxy, C 3 -C 6 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 3 -C 10 trialkylsilyl, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 haloalkylsulfonylamino 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;

each R 17 and R 18 is independently C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 cycloalkyl, C 3 -C 6 halocycloalkyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 7 alkylcycloalkyl, C 5 -C 7 alkylcycloalkylalkyl, C 1 -C 5 haloalkyl, C 1 -C 5 alkoxy or C 1 -C 5 haloalkoxy;

each Q is independently phenyl, benzyl, naphthalenyl, a 5- or 6-membered heteroaromatic ring or an 8- to 11-membered heteroaromatic bicyclic ring system, each optionally substituted with 1 to 5 substituents independently selected from R 7 on carbon atom ring members and R 12 on nitrogen atom ring members; or

each Q is independently a 3- to 7-membered nonaromatic carbocyclic ring, a 5-, 6- or 7-membered nonaromatic heterocyclic ring or an 8- to 11-membered nonaromatic bicyclic ring system, each optionally including ring members selected from the group consisting of C(═O), C(═S), S(O), S(O) 2 and SiR 17 R 18 , and optionally substituted with 1 to 5 substituents independently selected from R 7 on carbon atom ring members and R 12 on nitrogen atom ring members;

each R 7 is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 10 alkylcycloalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 6 cycloalkylamino, C 2 -C 4 alkoxyalkyl, C 1 -C 4 hydroxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 alkylcarbonylthio, C 2 -C 6 alkylaminocarbonyl, C 3 -C 8 dialkylaminocarbonyl or C 3 -C 6 trialkylsilyl; or

R 5 and R 7 are taken together with the atoms linking R 5 and R 7 to form an optionally substituted 5- to 7-membered ring containing ring members selected from carbon and optionally 1 to 3 heteroatoms selected from up to 1 O, up to 1 S and up to 1 N and optionally including 1 to 3 ring members selected from the group consisting of C(═O), C(═S), S(O), S(O) 2 and SiR 17 R 18 ;

each R 12 is independently H, C 1 -C 3 alkyl, C 2 -C 3 alkylcarbonyl, C 1 -C 3 alkoxy or C 2 -C 3 alkoxycarbonyl;

each Z 1 and Z 2 is independently a direct bond, O, S(O) m , CHR 20 or NR 21 ;

each Z 4 is independently O, C(═O), S(O) m or CHR 20 ;

each R 20 is independently H, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

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;

each m is independently 0, 1 or 2; and

n is 0, 1 or 2;

provided that:

(a) when R 1 is unsubstituted thienyl, X is X 1 and the ring containing X is saturated, G is an unsubstituted thiazole ring connected at its 2-position to X and at its 4-position to Z 1 in Formula 1, A is CHR 15 , R 15 is H, and J is an isoxazole ring connected at its 4-position to Z 1 and substituted at its 5-position with methyl and at its 3-position with meta-substituted phenyl, then Z 1 is O, S(O) m , CHR 20 or NR 21 ;

(b) when A is NR 16 , X is X 1 or X 2 , Z 1 is a direct bond, and J is phenyl, then J is substituted with at least one R 5 other than H, F, Cl, CN, OCH 3 , CF 3 and CH 3 ;

(c) when A is CHR 15 , R 15 is H, W is O, X is X 1 , n is 0, G is a thiazole ring connected at its 2-position to X, and at its 4-position to Z 1 in Formula 1, and bonded at its 5-position to H, F, Cl or Br, Z 1 is a direct bond, and R 1 is

then when J is a substituted phenyl or substituted pyrimidin-4-yl, it is substituted with at least one R 5 other than H, SCF 3 , OCF 3 , C(CH 3 ) 3 , S(O) 2 CF 3 , OCH 3 , CF 3 , Br, cyclopropyl, 1-methylcyclopropyl, OH or CF 2 CH 3 , and when J is a 2,3-dihydro-1H-inden-4-yl or 5,6,7,8-tetrahydronaphthalen-2-yl, it is substituted with at least one R 5 other than H, CH 3 or C(CH 3 ) 3 ; and

(d) the compound is not

1-[4-[4-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-2-thiazolyl]-1-piperidinyl]-2-(4-hydroxy-3,5-dinitrophenyl)ethanone,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1-[(2,4-dimethyl-1H-imidazol-1-yl)acetyl]piperidine,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1-[(2,5-dimethyl-1H-imidazol-1-yl)acetyl]piperidine,

[1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-2-methyl-1H-imidazol-4-yl]methanol,

[1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-2-methyl-1H-imidazol-5-yl]methanol,

[1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-4-methyl-1H-pyrazol-3-yl]acetic acid methyl ester,

[1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-4-methyl-1H-pyrazol-3-yl]acetate bis(hydrotrifluoroacetate),

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1 {[4-methyl-2-(methylsulfonyl)-1H-imidazol-1-yl]acetyl}piperidine,

1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-1,3-dihydro-2H-imidazol-2-one,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1H-[(4-methoxy-1-imidazol-1-yl)acetyl]piperidine,

4-[2-(8-tert-butyl-4,4-dimethyl-3,4-dihydro-2H-chromen-6-yl)-1,3-thiazol-4-yl]-1-[(2,4-dimethyl-1H-imidazol-1-yl)acetyl]piperidine,

1-[(4-chloro-2-methyl-1H-imidazol-1-yl)acetyl]-4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidine,

1-[(4-chloro-2,5-dimethyl-1H-imidazol-1-yl)acetyl]-4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidine,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1-[(2-ethyl-4-methyl-1H-imidazol-1-yl)acetyl]piperidine,

2,6-di-tent-butyl-4-(4-{1-[(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetyl]piperidin-4-yl}-1,3-thiazol-2-yl)phenol,

[1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-5-methyl-1H-imidazol-4-yl]methanol,

[1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-4-methyl-1H-imidazol-5-yl]methanol,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1-{2-(methylthio)-1H-imidazol-1-yl]acetyl}piperidine,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1-{2-(methylsulfonyl)-1H-imidazol-1-yl]acetyl}piperidine,

[1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-5-methyl-1H-imidazol-4-yl]acetic acid methyl ester,

[1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-5-methyl-1H-imidazol-4-yl]acetic dihydrochloride,

[1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-4-methyl-1H-imidazol-5-yl]acetic dihydrochloride,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1-[(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetyl]piperidine,

4-[2-(3,5-di-tert-butylphenyl)-1,3-thiazol-4-yl]-1-[(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetyl]piperidine,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1-[(4-methyl-1-imidazol-1-yl)acetyl]piperidine,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1-[(5-methyl-1-imidazol-1-yl)acetyl]piperidine,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1-[(3,5-dimethyl-1H-pyrazol-1-yl)acetyl]piperidine,

4-[2-(3,5-di-tert-butylphenyl)-1,3-thiazol-4-yl]-1-[(3,5-dimethyl-1H-pyrazol-1-yl)acetyl]piperidine,

4-[2-(3,5-di-tert-butylphenyl)-1,3-thiazol-4-yl]-1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidine,

1-{[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}-4-[2-(3,5-di-tert-butylphenyl)-1,3-thiazol-4-yl]piperidine,

1-[(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)acetyl]-4-[2-(3,5-di-tert-butylphenyl)-1,3-thiazol-4-yl]piperidine,

1-[(4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)acetyl]-4-[2-(3,5-di-tert-butylphenyl)-1,3-thiazol-4-yl]piperidine,

[1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-1H-imidazol-2-yl]methanol,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1-{[2-(trifluoromethyl)-1H-imidazol-1-yl]acetyl}piperidine,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1-{[2-methyl-1H-imidazol-1-yl]acetyl}piperidine,

4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]-1-(1H-imidazol-1-ylacetyl)piperidine,

[1-(2-{4-[2-(3,5-di-tert-butylphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-5-methyl-1H-pyrazol-3-yl]acetic acid methyl ester,

[1-(2-{4-[2-(3,5-di-tert-butylphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-5-methyl-1H-pyrazol-3-yl]acetic acid,

(1-{2-[4-(2-{3-tert-butyl-5-[(trifluoromethyl)thio]phenyl}-1,3-thiazol-4-yl)piperidin-1-yl]-2-oxoethyl}-5-methyl-1H-pyrazol-3-yl)acetic acid methyl ester,

potassium (1-{2-[4-(2-{3-tert-butyl-5-[(trifluoromethyl)thio]phenyl}-1,3-thiazol-4-yl)piperidin-1-yl]-2-oxoethyl}-5-methyl-1H-pyrazol-3-yl)acetate,

4-[2-(3,5-di-tert-butylphenyl)-1,3-thiazol-4-yl]-1-[(2,4-dimethyl-1H-imidazol-1-yl)acetyl]piperidine,

4-{2-[3,5-bis(trifluoromethyl)phenyl]-1,3-thiazol-4-yl}-1-[(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetyl]piperidine,

1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-1H-imidazole-2-carboxylic acid ethyl ester,

1-(2-{4-[2-(3,5-di-tert-butyl-4-methoxyphenyl)-1,3-thiazol-4-yl]piperidin-1-yl}-2-oxoethyl)-1H-imidazole-2-carboxylic acid dihyrdrochloride,

4-(1-benzylpyrrolidin-3-yl)-N-(3,4-dichlorophenyl)piperazine-1-carboxamide,

4,4-diphenyl-1-[1-(2-phenylacetyl)-4-piperidinyl]-2-imidazolidinone,

4-(2-oxo-4,4-diphenyl-1-imidazolidinyl)-N-phenyl-1-piperidinecarboxamide,

N-pyridin-3-yl-4-(3-pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide,

4-[3-(3-furyl)-1,2,4-thiadiazol-5-yl]-N-pyridin-3-ylpiperazine-1-carboxamide,

N-pyridin-4-yl-4-(3-pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide,

4[3-(3-furyl)-1,2,4-thiadiazol-5-yl]-N-pyridin-4-ylpiperazine-1-carboxamide,

N-pyridin-3-yl-4-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamide,

N-pyridin-3-yl-4-[3-(3-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamide,

N-pyridin-4-yl-4-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamide,

N-pyridin-4-yl-4-[3-(3-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamide,

N-(3,4-dimethylisoxazol-5-yl)-4-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamide,

2-((1S,2S,4R)-bicyclo [2.2.1]heptan-2-ylamino)-5-methyl-5-(1-(2-(pyridin-4-yl)acetyl)piperidin-4-yl)thiazol-4(5H)-one,

2-((1S,2S,4R)-bicyclo [2.2.1]heptan-2-ylamino)-5-methyl-5-(1-(2-(pyridin-3-yl)acetyl)piperidin-4-yl)thiazol-4(5H)-one,

2-((1S,2S,4R)-bicyclo [2.2.1]heptan-2-ylamino)-5-methyl-5-(1-(2-phenylacetyl)piperidin-4-yl)thiazol-4(5H)-one,

1-[4-[4-(4-chlorophenyl)-5-(2H-1,2,3-triazol-2-ylmethyl)-4H-1,2,4-triazol-3-yl]-1-piperidinyl]-2-(2,5-dimethyl-4-thiazolyl)-ethanone,

2-[1,1′-biphenyl]-4-yl-1-[4-[4-(4-chlorophenyl)-5-(2H-1,2,3-triazol-2-ylmethyl)-4H-1,2,4-triazol-3-yl]-1-piperidinyl]-ethanone,

2-(4-chlorophenyl)-1-[4-[4-(4-chlorophenyl)-5-(2H-1,2,3-triazol-2-ylmethyl)-4H-1,2,4-triazol-3-yl]-1-piperidinyl]-1-propanone,

2-(2-chloro-4-fluorophenyl)-1-[4-[4-(4-chlorophenyl)-5-(2H-1,2,3-triazol-2-ylmethyl)-4H-1,2,4-triazol-3-yl]-1-piperidinyl]-ethanone,

2-(3-chlorophenyl)-1-[4-[4-(4-chlorophenyl)-5-(2H-1,2,3-triazol-2-ylmethyl)-4H-1,2,4-triazol-3-yl]-1-piperidinyl]-ethanone,

1-[4-[4-(4-chlorophenyl)-5-(2H-1,2,3-triazol-2-ylmethyl)-4H-1,2,4-triazol-3-yl]-1-piperidinyl]-2-(4-fluorophenyl)-ethanone,

4-[4-(4-chlorophenyl)-5-(2H-1,2,3-triazol-2-ylmethyl)-4H-1,2,4-triazol-3-yl]-1-[(2-methoxyphenyl)acetyl]-piperidine, or

1-[4-[4-(4-chlorophenyl)-5-(2H-1,2,3-triazol-2-ylmethyl)-4H-1,2,4-triazol-3-yl]-1-piperidinyl]-2-(2-naphthalenyl)-ethanone.

2. A compound of claim 1 wherein

G is a 5-membered heteroaromatic ring or 5-membered saturated or partially saturated heterocyclic ring, each ring optionally substituted with up to 2 substituents selected from R 3 on carbon ring members and selected from R 11 on nitrogen ring members;

R 1 is a phenyl or 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 2 substituents independently selected from R 4a on carbon ring members and R 4b on nitrogen ring members;

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

each R 3 is independently C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or halogen;

each R 4a is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 10 alkylcycloalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 6 cycloalkylamino, C 2 -C 4 alkoxyalkyl, C 1 -C 4 hydroxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 alkylcarbonylthio, C 2 -C 6 alkylaminocarbonyl, C 3 -C 8 dialkylaminocarbonyl or C 3 -C 6 trialkylsilyl;

each R 4b is independently C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 3 -C 6 haloalkenyl, C 3 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl or C 2 -C 4 alkoxyalkyl;

each R 11 is independently C 1 -C 3 alkyl;

R 15 is H, halogen, cyano, hydroxy, —CHO, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 2 -C 5 alkoxycarbonyl;

R 16 is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl or C 2 -C 4 alkoxycarbonyl;

when R 5 and R 7 are taken together with the atoms linking R 5 and R 7 to form an optionally substituted 5- to 7-membered ring, then R 5 and R 7 are taken together with the atoms linking R 5 and R 7 to form a 5- to 7-membered ring containing ring members selected from carbon and optionally 1 to 3 heteroatoms selected from up to 1 O, up to 1 S and up to 1 N, and optionally including 1 to 3 ring members selected from the group consisting of C(═O), C(═S), S(O), S(O) 2 and SiR 17 R 18 , the ring optionally substituted on ring members other than the atoms linking R 5 and R 7 with up to 4 substituents selected from R 8 ;

each R 8 is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 10 alkylcycloalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 6 cycloalkylamino, C 2 -C 4 alkoxyalkyl, C 1 -C 4 hydroxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 alkylcarbonylthio, C 2 -C 6 alkylaminocarbonyl, C 3 -C 8 dialkylaminocarbonyl or C 3 -C 6 trialkylsilyl; and

each Z 4 is independently C(═O) or S(O) 2 .

3. A compound of claim 2 wherein

G is

wherein the bond projecting to the left is bonded to X, and bond projecting to the right is bonded to Z 1 ;

J is

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

Q is

R 1 is

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

each R 3a is independently selected from H and R 3 ;

each R 5 is independently H, cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 2 -C 6 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 6 alkylthioalkyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 2 -C 6 alkoxyalkoxy, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 haloalkylcarbonyloxy, C 4 -C 8 cycloalkylcarbonyloxy, C 3 -C 6 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 3 -C 10 trialkylsilyl, —NR 25 R 26 or Z 2 Q;

R 11a is selected from H and R 11 ;

R 15 is H, cyano, hydroxy, methyl or methoxycarbonyl;

R 16 is H, methyl, methylcarbonyl or methoxycarbonyl;

each Z 4 is C(═O);

k is 0, 1 or 2;

p is 0, 1,2 or 3; and

x is an integer from 0 to 5;

provided that:

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

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

(d) when G is G-25 or G-31, then at least one R 3a is H; and

(e) when G is one of G-31 through G-35, then Z 1 is a direct bond or CHR 20 .

4. A compound of claim 3 wherein

G is selected from G-1, G-2, G-7, G-8, G-14, G-15, G-23, G-24, G-26, G-27, G-36, G-37, G-38, G-49, G-50 and G-55;

J is selected from J-1, J-2, J-3, J-4, J-5, J-7, J-8, J-9, J-10, J-11, J-12, J-14, J-15, J-16, J-20, J-24, J-25, J-26, J-29, J-30, J-37, J-38, J-45 and J-69;

each Q is independently Q-1, Q-20, Q-32 through Q-34, Q-45 through Q-47, Q-60 through Q-73, Q-76 through Q-79, Q-84 through Q-94 or Q-98 through Q-102;

A is CH 2 or NH;

W is O;

X is X 1 , X 2 or X 3 ;

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 alkoxyalkyl, 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 alkoxyalkoxy, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 haloalkylcarbonyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 10 trialkylsilyl, —NR 25 R 26 or Z 2 Q;

Z 1 is a direct bond;

each Z 2 is independently a direct bond or NR 21 ;

R 1 is selected from U-1 through U-3, U-11, U-13, U-20, U-22, U-23, U-36 through U-39 and U-50;

each R 3 is independently methyl or halogen;

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;

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;

k is 1 or 2; and

n is 0.

5. A compound of claim 4 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 or X 2 ; 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; 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.

6. A compound of claim 5 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;

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; and

X is X 1 .

7. A compound of claim 1 wherein

R 1 is an optionally substituted phenyl or 5- or 6-membered heteroaromatic ring;

A is CH 2 or NH;

X is X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 or X 8 ;

each R 2 is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, halogen, cyano or hydroxy; or

two R 2 are taken together as C 1 -C 3 alkylene or C 2 -C 3 alkenylene to form a bridged bicyclic ring system; or

J is a 5- or 6-membered ring or a 8- to 11-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon and optionally 1 to 3 heteroatoms selected from up to 1 O, up to 1 S and up to 3 N, and optionally including 1 to 3 ring members selected from the group consisting of C(═O), C(═S), S(O), or S(O) 2 , each ring or ring system optionally substituted with 1 to 5 substituents independently selected from R 5 ;

each R 5 is independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 10 alkylcycloalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, hydroxy, amino, cyano, nitro, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 alkylaminocarbonyl, C 3 -C 8 dialkylaminocarbonyl, C 3 -C 6 trialkylsilyl or —Z 2 Q;

each Q is independently an optionally substituted phenyl, benzyl, naphthalenyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl or 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 3 substituents selected from R 7 on carbon ring members and R 12 on nitrogen ring members;

R 5 and R 7 are taken together with the atoms linking R 5 and R 7 to form an optionally substituted 5- to 7-membered ring containing as ring members 2 to 7 carbon atoms and optionally 1 to 3 heteroatoms selected from up to 1 O, up to 1 S and up to 1 N;

R 12 is C 1 -C 3 alkyl; and

R 21 is H or C 1 -C 3 alkyl.

8. A compound of claim 7 wherein

R 1 is a phenyl or 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 2 substituents independently selected from R 4a on carbon ring members and R 4b on nitrogen ring members;

each R 3 is independently C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or halogen;

each R 11 is independently C 1 -C 3 alkyl; and

when R 5 and R 7 are taken together with the atoms linking R 5 and R 7 to form an optionally substituted 5- to 7-membered ring, then R 5 and R 7 are taken together with the atoms linking R 5 and R 7 to form a 5- to 7-membered ring containing as ring members 2 to 7 carbon atoms and optionally 1 to 3 heteroatoms selected from up to 1 O, up to 1 S and up to 1 N, optionally substituted with up to 2 substituents selected from R 8 ; and each R 8 is independently C 1 -C 3 alkyl.

9. A compound of claim 8 wherein

G is

J is

Q is

R 1 is

each R 3a is independently selected from H and R 3 ;

R 11a is selected from H and R 11 ;

k is 0, 1 or 2;

p is 0, 1 or 2; and

x is an integer from 0 to 5;

provided that:

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

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

(d) when G is G-25 or G-31, then at least one R 3a is H; and

(e) when G is one of G-31 through G-35, then Z 1 is a direct bond or CHR 20 .

10. A compound of claim 9 wherein

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

J is selected from J-1, J-2, J-3, J-4, J-5, J-7, J-8, J-9, J-10, J-11, J-12, J-14, J-15, J-16, J-20, J-24, J-25, J-26, J-29, J-30, J-45 and J-69;

each Q is independently Q-1, Q-20, Q-32 to Q-34, Q-45 Q-46 or Q-47;

W is O;

X is X 1 , X 2 or X 3 ;

each Z 1 and Z 2 is a direct bond;

R 1 is selected from U-1 through U-3, U-11, U-13, U-20, U-22, U-23, U-36 through U-39 and U-50;

each R 3 is independently methyl or halogen;

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

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

one instance of R 5 is Z 2 Q and other instances of R 5 are independently selected from H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and halogen;

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

k is 1 or 2; and

n is 0.

11. A compound of claim 10 wherein

A is CH 2 ;

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

J is selected from J-11, J-25, J-26, J-29 and J-30;

Q is selected from Q-1 and Q-45;

X is X 1 or X 2 ; and the ring comprising X is saturated;

R 1 is U-1 or U- 50; and

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

12. A compound of claim 11 wherein

J is selected from J-11 and J-29;

X is X 1 ; and

each R 4a is independently C 1 -C 2 alkyl, trifluoromethyl or Cl.

13. A compound of claim 1 wherein

R 1 is U-1 or U-50 wherein when R 4 is attached to a carbon ring member, said R 4 is selected from R 4a ;

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

A is CH 2 ;

W is O;

X is X 1 or X 2 and ring comprising X is saturated;

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

G is selected from G-1, G-2, G-15, G-26 and G-36 wherein the bond projecting to the left is bonded to X, and bond projecting to the right is bonded to Z 1 ;

each R 3a is independently selected from H and R 3 ;

each R 3 is independently methyl or halogen;

J is selected from J-11, J-25, J-26, J-29 and J-30; wherein the bond shown projecting to the left is bonded to Z 1 ;

each R 5 is independently H, halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —NR 25 R 26 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 6 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 6 alkylthioalkyl, C 2 -C 6 alkylsulfinylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 alkylaminoalkyl, C 3 -C 8 dialkylaminoalkyl, C 2 -C 6 haloalkylaminoalkyl, C 4 -C 10 cycloalkylaminoalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 4 -C 8 cycloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 4 -C 8 cycloalkoxycarbonyl, C 5 -C 10 cycloalkylalkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 8 dialkylaminocarbonyl, C 4 -C 8 cycloalkylaminocarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 2 -C 6 alkoxyalkoxy, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 haloalkylcarbonyloxy, C 4 -C 8 cycloalkylcarbonyloxy, C 3 -C 6 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 3 -C 10 trialkylsilyl, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 haloalkylsulfonylamino or —Z 2 Q;

each Q is independently selected from Q-1, Q-45 and Q-63;

R 5 and R 7 are taken together with the atoms linking R 5 and R 7 to form a 5- to 7-membered ring containing as ring members 2 to 7 carbon atoms and optionally 1 to 3 heteroatoms selected from up to 1 O, up to 1 S and up to 1 N and optionally including 1 ring member selected from SiR 17 R 18 , the ring optionally substituted on ring members other than the atoms linking R 5 and R 7 with up to 4 substituents selected from R 8 ;

each Z 1 and Z 2 is a direct bond;

each Z 4 is independently C(═O) or S(O) 2 ;

n is 0, 1 or 2;

k is 0, 1 or 2;

p is 0, 1 or 2; and

x is an integer from 0 to 5.

14. A compound of claim 1 wherein

each R 5 is independently H, halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —NR 25 R 26 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 6 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 6 alkylthioalkyl, C 2 -C 6 alkylsulfinylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 alkylaminoalkyl, C 3 -C 8 dialkylaminoalkyl, C 2 -C 6 haloalkylaminoalkyl, C 4 -C 10 cycloalkylaminoalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 4 -C 8 cycloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 4 -C 8 cycloalkoxycarbonyl, C 5 -C 10 cycloalkylalkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 8 dialkylaminocarbonyl, C 4 -C 8 cycloalkylaminocarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 2 -C 6 alkoxyalkoxy, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 haloalkylcarbonyloxy, C 4 -C 8 cycloalkylcarbonyloxy, C 3 -C 6 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 3 -C 10 trialkylsilyl, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 haloalkylsulfonylamino or —Z 2 Q;

each R 12 is independently C 1 -C 3 alkyl.

15. A compound of claim 14 wherein

R 1 is a phenyl or 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 2 substituents independently selected from R 4a on carbon ring members and R 4b on nitrogen ring members;

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

each R 3 is independently C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or halogen;

each R 11 is independently C 1 -C 3 alkyl;

R 15 is H, halogen, cyano, hydroxy, —CHO, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 2 -C 5 alkoxycarbonyl;

R 16 is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl or C 2 -C 4 alkoxycarbonyl;

when R 5 and R 7 are taken together with the atoms linking R 5 and R 7 to form an optionally substituted 5- to 7-membered ring, then R 5 and R 7 are taken together with the atoms linking R 5 and R 7 to form a 5- to 7-membered ring containing as ring members 2 to 7 carbon atoms and optionally 1 to 3 heteroatoms selected from up to 1 O, up to 1 S and up to 1 N and optionally including 1 ring member selected from SiR 17 R 18 , the ring optionally substituted on ring members other than the atoms linking R 5 and R 7 with up to 4 substituents selected from R 8 ;

each Z 4 is independently C(═O) or S(O) 2 .

16. A compound of claim 1 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′(2′H)-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)ethanone and its enantiomer,

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

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(triflyoromethyl)-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-chlorophenyl)-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-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[3-methyl-5-(trifluoromethyl)-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, and

(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.

17. 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 selected from the group consisting of the compounds of claim 1 , compounds within the scope of exclusion of proviso (a) of claim 1 , compounds within the scope of exclusion of proviso (b) of claim 1 , compounds within the scope of exclusion of proviso (c) of claim 1 , and compounds within the scope of exclusion of proviso (d) of claim 1 .

18. A fungicidal composition comprising (1) a compound selected from the group consisting of the compounds of claim 1 , compounds within the scope of exclusion of proviso (a) of claim 1 , compounds within the scope of exclusion of proviso (b) of claim 1 , compounds within the scope of exclusion of proviso (c) of claim 1 , and compounds within the scope of exclusion of proviso (d) of claim 1 ; and (2) at least one other fungicide.

19. A fungicidal composition comprising (1) a fungicidally effective amount of a compound selected from the group consisting of the compounds of claim 1 , compounds within the scope of exclusion of proviso (a) of claim 1 , compounds within the scope of exclusion of proviso (b) of claim 1 , compounds within the scope of exclusion of proviso (c) of claim 1 , and compounds within the scope of exclusion of proviso (d) of claim 1 ; and (2) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

20. A compound selected from Formula 1, an N-oxide and salt thereof,

wherein

R 1 is

wherein when R 4 is attached to a carbon ring member, said R 4 is selected from R 4a ;

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

A is CH 2 ;

W is O;

X is

wherein the bond of X 1 or X 2 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, and ring comprising X is saturated;

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

G is

wherein the bond projecting to the left is bonded to X, and bond projecting to the right is bonded to Z 1 ;

each R 3a is independently selected from H and 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, halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —NR 25 R 26 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 6 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 6 alkylthioalkyl, C 2 -C 6 alkylsulfinylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 alkylaminoalkyl, C 3 -C 8 dialkylaminoalkyl, C 2 -C 6 haloalkylaminoalkyl, C 4 -C 10 cycloalkylaminoalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 4 -C 8 cycloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 4 -C 8 cycloalkoxycarbonyl, C 5 -C 10 cycloalkylalkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 8 dialkylaminocarbonyl, C 4 -C 8 cycloalkylaminocarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 2 -C 6 alkoxyalkoxy, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 haloalkylcarbonyloxy, C 4 -C 8 cycloalkylcarbonyloxy, C 3 -C 6 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 3 -C 10 trialkylsilyl, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 haloalkylsulfonylamino 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 Q is independently selected from

R 5 and R 7 are taken together with the atoms linking R 5 and R 7 to form a 5- to 7-membered ring containing as ring members 2 to 7 carbon atoms and optionally 1 to 3 heteroatoms selected from up to 1 O, up to 1 S, up to 1 Si and up to 1 N, the ring optionally substituted on ring members other than the atoms linking R 5 and R 7 with up to 4 substituents selected from R 8 ;

each Z 1 and Z 2 is a direct bond;

each Z 4 is independently C(═O) or S(O) 2 ;

n is 0, 1 or 2;

k is 0, 1 or 2;

p is 0, 1 or 2; and

x is an integer from 0 to 5.

21. A compound of claim 20 wherein

R 1 is U-1;

X is X 1 ;

G is G-1, and G is unsubstituted;

J is J-29;

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

n is 0.

22. A compound of claim 21 wherein the 3-position of J-29 is connected to Z 1 and the 5-position of J-29 is connected to Z 2 Q;

R 5 is Z 2 Q;

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

each R 7 is independently methyl, F, Cl, Br, hydroxy, cyano or methoxy; and

x is 1.

23. The compound of claim 22 which 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 and its enantiomer.

24. A compound which 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 and its enantiomer.

25. 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 selected from Formula 1, an N-oxide and salt thereof,

wherein

R 1 is an optionally substituted phenyl, naphthalenyl or 5- or 6-membered heteroaromatic ring;

A is CHR 15 or NR 16 ;

W is O or S;

X is a radical selected from

each R 2 is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, halogen, cyano or hydroxy; or

two R 2 are taken together as C 1 -C 4 alkylene or C 2 -C 4 alkenylene to form a bridged bicyclic or fused bicyclic ring system; or

G is an optionally substituted 5-membered heteroaromatic ring or 5-membered saturated or partially saturated heterocyclic ring;

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 12 is independently H, C 1 -C 3 alkyl, C 2 -C 3 alkylcarbonyl, C 1 -C 3 alkoxy or C 2 -C 3 alkoxycarbonyl;

Z 1 is a direct bond, O, S(O) m , CHR 20 or NR 21 ;

each Z 2 is independently a direct bond, O, C(═O), S(O) m , CHR 20 or NR 21 ;

each Z 4 is independently O, C(═O), S(O) m or CHR 20 ;

each R 20 is independently H, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

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;

each m is independently 0, 1 or 2; and

n is 0, 1 or 2.

26. The method of claim 25 , wherein the compound 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 and its enantiomer.

27. A fungicidal composition comprising (1) a compound selected from Formula 1, an N-oxide and salt thereof,

wherein

R 1 is an optionally substituted phenyl, naphthalenyl or 5- or 6-membered heteroaromatic ring;

A is CHR 15 or NR 16 ;

W is O or S;

X is a radical selected from

each R 2 is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, halogen, cyano or hydroxy; or

two R 2 are taken together as C 1 -C 4 alkylene or C 2 -C 4 alkenylene to form a bridged bicyclic or fused bicyclic ring system; or

G is an optionally substituted 5-membered heteroaromatic ring or 5-membered saturated or partially saturated heterocyclic ring;

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 12 is independently H, C 1 -C 3 alkyl, C 2 -C 3 alkylcarbonyl, C 1 -C 3 alkoxy or C 2 -C 3 alkoxycarbonyl;

Z 1 is a direct bond, O, S(O) m , CHR 20 or NR 21 ;

each Z 2 is independently a direct bond, O, C(═O), S(O) m , CHR 20 or NR 21 ;

each Z 4 is independently O, C(═O), S(O) m or CHR 20 ;

each R 20 is independently H, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

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;

each m is independently 0, 1 or 2; and

n is 0, 1 or 2; and

(2) at least one other fungicide.

28. A fungicidal composition comprising (1) a fungicidally effective amount of a compound selected from Formula 1, an N-oxide and salt thereof,

wherein

R 1 is an optionally substituted phenyl, naphthalenyl or 5- or 6-membered heteroaromatic ring;

A is CHR 15 or NR 16 ;

R 15 is H, halogen, cyano, hydroxy, —CHO, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl,

C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylthioalkyl, C 2 -C 4 alkylsulfinylalkyl, C 2 -C 4 alkylsulfonylalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 5 alkoxycarbonyl, C 3 -C 5 alkoxycarbonylalkyl, C 2 -C 5 alkylaminocarbonyl, C 3 -C 5 dialkylaminocarbonyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl or C 1 -C 4 haloalkylsulfonyl;

W is O or S;

X is a radical selected from

each R 2 is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, halogen, cyano or hydroxy; or

two R 2 are taken together as C 1 -C 4 alkylene or C 2 -C 4 alkenylene to form a bridged bicyclic or fused bicyclic ring system; or

G is an optionally substituted 5-membered heteroaromatic ring or 5-membered saturated or partially saturated heterocyclic ring;

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 12 is independently H, C 1 -C 3 alkyl, C 2 -C 3 alkylcarbonyl, C 1 -C 3 alkoxy or C 2 -C 3 alkoxycarbonyl;

Z 1 is a direct bond, O, S(O) m , CHR 20 or NR 21 ;

each Z 2 is independently a direct bond, O, C(═O), S(O) m , CHR 20 or NR 21 ;

each Z 4 is independently O, C(═O), S(O) m or CHR 20 ;

each R 20 is independently H, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

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;

each m is independently 0, 1 or 2; and

n is 0, 1 or 2; and

(2) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

29. The composition of claim 27 , wherein the compound 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 and its enantiomer.

30. The composition of claim 28 , wherein the compound 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 and its enantiomer.

31. The compound of claim 13 , wherein the compound 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 and its enantiomer.

32. The compound of claim 16 , wherein the compound 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 and its enantiomer.

Assignments (1)

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 →

Continuity (4)

Continuation In Part PCTUS2007014647 · Jun 22, 2007

Provisional Application 60833824 · Jul 27, 2006

Provisional Application 60897173 · Jan 24, 2007

Related Publication 20090156592A1 · Jun 18, 2009