IP Library › Granted Patent US 9,643,963

Granted Patent B2

US 9,643,963 · App. 15/036,335 · Granted May 9, 2017

Antiparasitic compounds

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Patent No.: US 9,643,963
App. No.: 15/036,335
Granted: May 9, 2017
Kind: B2

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Abstract

The invention relates to 1,2,4-thiadiazole derivatives and their use to treat parasites.

Claims (314)

1. A compound of formula (I)

wherein:

A is C═O or SO 2 ;

X is R 1 or NHR 1 ;

R 1 is:

phenyl optionally substituted by from one to three substituents, which are the same or different, each selected from the group consisting of nitro, —NR 3 R 4 , cyano, —NR 3 COR 5 , alkyl, —SO 2 R 5 , —NR 3 SO 2 R 5 , —SO 2 NR 3 R 4 , —CONR 3 R 4 , —CONHC 6 H 5 , hydroxy, alkoxy, aryloxy, aryl, heterocyclyl, haloalkyl, haloalkoxy, mercapto, thioalkyl and halogen;

naphthyl optionally substituted by from one to three substituents, which are the same or different, each independently selected from the group consisting of nitro, —NR 3 R 4 , cyano, —NR 3 COR 5 , alkyl, —SO 2 R 5 , —NR 3 SO 2 R 5 , —SO 2 NR 3 R 4 , —CONR 3 R 4 , —CONHC 6 H 5 , hydroxy, alkoxy, aryloxy, aryl, heterocyclyl, haloalkyl, haloalkoxy, mercapto, thioalkyl and halogen;

quinoxolinyl optionally substituted by from one to three substituents, which are the same or different, each independently selected from the group consisting of nitro, —NR 3 R 4 , cyano, —NR 3 COR 5 , alkyl, —SO 2 R 5 , —NR 3 SO 2 R 5 , —SO 2 NR 3 R 4 , —CONR 3 R 4 , —CONHC 6 H 5 , hydroxy, alkoxy, aryloxy, aryl, heterocyclyl, haloalkyl, haloalkoxy, mercapto, thioalkyl and halogen;

quinolinyl optionally substituted by from one to three substituents, which are the same or different, each independently selected from the group consisting nitro, —NR 3 R 4 , cyano, —NR 3 COR 5 , alkyl, —SO 2 R 5 , —NR 3 SO 2 R 5 , —SO 2 NR 3 R 4 , —CONR 3 R 4 , —CONHC 6 H 5 , hydroxy, alkoxy, aryloxy, aryl, heterocyclyl, haloalkyl, haloalkoxy, mercapto, thioalkyl and halogen;

or thionyl or furyl optionally substituted by from one to three substituents which are the same or different, each selected from the group consisting of nitro, —NR 3 R 4 , cyano, —NR 3 COR 5 , alkyl, —SO 2 R 5 , —NR 3 SO 2 R 5 , —SO 2 NR 3 R 4 , —CONR 3 R 4 , —CONHC 6 H 5 , hydroxy, alkoxy, aryloxy, aryl, heterocyclyl, haloalkyl, haloalkoxy, mercapto (—SH), thioalkyl and halogen;

R 2 is hydrogen, halogen, alkyl, alkoxy, haloalkyl or haloalkoxy, aminoalkyl, alkylaminoalkyl, aryl, heterocyclyl or —CONR 3 R 4 ; or R 2 , together with two adjacent carbons of the pyridyl ring to which it is attached, forms a saturated or unsaturated ring containing from 4 to 6 ring atoms;

R 3 and R 4 , which are the same or different, each independently represent hydrogen or alkyl; or when R 3 and R 4 are each attached to a nitrogen atom, they may form a saturated or unsaturated heterocyclic ring containing from 4 to 6 ring atoms

R 5 is alkyl or haloalkyl;

or a pesticidally acceptable salt thereof.

2. The compound of claim 1 , where R 2 is hydrogen or halogen.

3. The compound of claim 1 , where R 1 is phenyl substituted by from one to three substituents which are the same or different, each selected from the group consisting of halogen, cyano, haloalkyl, alkoxy and haloalkoxy; or R 1 is naphthyl optionally substituted by from one to three substituents which are the same or different, each selected from the group consisting of halogen, cyano, haloalkyl, alkoxy and haloalkoxy.

4. The compound of claim 1 , where:

A is C═O;

X is NHR 1 ;

R 1 is phenyl optionally substituted by from one to three substituents which are the same or different, each selected from the group consisting of trifluoromethyl, trifluoromethoxy, halogen, cyano, methyl, ethyl, methoxy, ethoxy, thiomethyl, —SO 2 CH 3 , —SO 2 NH 2 , —SO 2 NHCH 3 , —SO 2 N(CH 3 ) 2 and —NHSO 2 CH 3 ;

and R 2 is hydrogen, fluoro, methyl, trifluoromethyl, methoxy or trifluoromethoxy.

5. The compound of claim 1 , where:

A is C═O;

X is R 1 ;

R 1 is phenyl substituted by from one to three substituents which are the same or different selected from the group consisting of trifluoromethyl, trifluoromethoxy, chloro, fluoro, cyano, methyl, ethyl, methoxy, ethoxy, aryloxy, thiomethyl, —SO 2 CH 3 , —SO 2 NH 2 , —SO 2 NHCH 3 , —SO 2 N(CH 3 ) 2 and —NHSO 2 CH 3 ; and

R 2 is hydrogen, fluoro, methyl, trifluoromethyl, methoxy, trifluoromethoxy, morpholino, aminoalkyl or dimethylaminomethyl.

6. The compound of claim 1 , where:

A is SO 2 ;

X is R 1 ;

R 1 is phenyl substituted by from one to three substituents which are the same or different selected from the group consisting of trifluoromethyl, trifluoromethoxy, chloro, fluoro, cyano, methyl, ethyl, methoxy, ethoxy, thiomethyl, methanesulfonyl, sulfonamide, methylsulfonamide, dimethylsulfonamide, and methylsulfonanilide; and

R 2 is hydrogen.

7. The compound of claim 1 , where:

A is C═O or SO 2 ;

X is R 1 or NHR 1 ;

R 1 is:

phenyl optionally substituted by from one to three substituents which are the same or different, each selected from the group consisting of nitro, —NR 3 R 4 , cyano, —NR 3 COR 5 , alkyl, alkoxy, aryl, heterocyclyl, aryloxy, haloalkyl, haloalkoxy, mercapto (—SH), thioalkyl and halogen;

R 2 is hydrogen, fluoro, methyl, trifluoromethyl, methoxy, trifluoromethoxy, morpholino, aminoalkyl or dimethylaminomethyl.

8. A compound selected from:

1-(4-methoxyphenyl)-3-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]urea;

1-(2-chlorophenyl)-3-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]urea;

1-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-[4-(trifluoromethyl)phenyl]urea;

1-(3-methoxyphenyl)-3-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]urea;

1-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-[4-(trifluoromethoxy)phenyl]urea;

1-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-[3-(trifluoromethyl)phenyl]urea;

4-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-cyano-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-fluoro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]naphthalene-2-carboxamide;

4-trifluoromethoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide;

2-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide;

4-cyano-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide;

4-methoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide;

2-methoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-(trifluoromethyl)benzenesulfonamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzenesulfonamide;

N-[3-(3-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(4-morpholino-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[benzyl(methyl)amino]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(dimethylamino)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[2-methoxyethyl(methyl)amino]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-methoxy-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(4-methoxy-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(triazolo[4,5-b]pyridin-3-yloxy)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-bromo-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

methyl 2-[5-[[4-(trifluoromethyl)benzoyl]amino]-1,2,4-thiadiazol-3-yl]pyridine-4-carboxylate;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]isoquinoline-7-carboxamide;

4-acetamido-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-fluoro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-nitro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]quinoxaline-6-carboxamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]thiophene-2-carboxamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]thiophene-3-carboxamide;

N-[3-(4-isopropyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(3-isoquinolyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-methyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

3-chloro-4-fluoro-N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethoxy)benzamide;

4-tert-butyl-N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]-3,5-bis(trifluoromethyl)benzamide;

N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-(trifluoromethyl)benzamide;

3,4-dichloro-N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-methylsulfonyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]isoquinoline-5-carboxamide;

3-chloro-4-(4-methylpiperazin-1-yl)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

methyl 4-[[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]carbamoyl]benzoate;

4-(diethylsulfamoyl)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-methyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]thiophene-2-carboxamide;

3-chloro-4-fluoro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

2-fluoro-3-methoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-(trifluoromethyl)benzamide;

2,5-dimethyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]furan-3-carboxamide;

4-tert-butyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-1,3-benzodioxole-5-carboxamide;

3,4-dichloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3,5-bis(trifluoromethyl)benzamide;

4-methoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-phenoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-fluoro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-2-(trifluoromethyl)benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-[[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]carbamoyl]benzoic acid;

4-iodo-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-morpholino-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-(morpholine-4-carbonyl)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

tert-butyl 4-[4-[[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]carbamoyl]benzoyl]piperazine-1-carboxylate;

tert-butyl 4-[[4-[[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]carbamoyl]benzoyl]amino]piperidine-1-carboxylate;

4-(piperidine-1-carbonyl)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-(piperazine-1-carbonyl)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N1-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]terephthalamide;

4-(2-pyridylamino)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

tert-butyl 4-[4-[[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]carbamoyl]anilino]piperidine-1-carboxylate;

4-phenyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-piperazin-1-yl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-(4-piperidylamino)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

tert-butyl 4-[4-[[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]carbamoyl]phenyl]piperazine-1-carboxylate;

3-chloro-2-fluoro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-5-(trifluoromethyl)benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(1,1,2,2-tetrafluoroethoxy)benzamide;

2-methoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethoxy)benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-5-(trifluoromethyl)furan-2-carboxamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-5-(trifluoromethyl)thiophene-2-carboxamide;

4-formyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-[hydroxy(phenyl)methyl]-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-bromo-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-benzyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N4-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]terephthalamide;

4-bromo-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethoxy)benzamide;

N-[3-(4-phenyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

4-(trifluoromethyl)-N-[3-[5-(trifluoromethyl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]benzamide;

N4-phenyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]terephthalamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-2-(trifluoromethyl) benzamide;

2-fluoro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethoxy)benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-2-(trifluoromethoxy)benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-(trifluoromethoxy)benzamide;

4-(4-fluorophenoxy)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-hydroxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-5-(trifluoromethyl)thiophene-2-carboxamide;

4-(2,4-difluorophenoxy)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-[4-(trifluoromethyl)phenoxy]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-[4-(trifluoromethyl)phenoxy]benzamide;

3-(4-fluorophenoxy)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-phenoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N1-(4-piperidyl)-N4-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]terephthalamide;

N-[3-(5-piperazin-1-yl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

4-(4-piperidyloxy)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]pyridine-2-carboxamide;

N-[3-(6-piperazin-1-yl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

4-(3-pyridyl)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(5-phenyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

4-(trifluoromethyl)-N-[3-(5-vinyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-[5-(3,6-dihydro-2H-pyran-4-yl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(6-phenyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[6-(3-pyridyl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-trifluoromethyl)benzamide;

4-anilino-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-(benzylamino)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-anilino-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-[5-(3-pyridylamino)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-morpholino-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[5-[2-methoxyethyl(methyl)amino]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-pyrrolidin-1-yl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[5-(2-pyridylamino)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[5-(4-methylpiperazin-1-yl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

tert-butyl 4-[6-[5-[[4-(trifluoromethyl)benzoyl]amino]-1,2,4-thiadiazol-3-yl]-3-pyridyl]piperazine-1-carboxylate;

N-[3-[5-(1-piperidyl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-anilino-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[5-(4-hydroxy-1-piperidyl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[6-(4-methylpiperazin-1-yl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

tert-butyl 4-[6-[5-[[4-(trifluoromethyl)benzoyl]amino]-1,2,4-thiadiazol-3-yl]-2-pyridyl]piperazine-1-carboxylate;

N-[3-(4-Methyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(6-Methyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(dimethylaminomethyl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[methyl-[2-(1-piperidyl)ethyl]amino]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[methyl(2-morpholinoethyl)amino]-2-pyridyl]-1,2,4-tiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(4-pyrrolidin-1-yl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(4-methylpiperazin-1-yl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[2-hydroxyethyl(methyl)amino]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[2-(1-piperidyl)ethoxy]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(2-methoxyethoxy)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(2-dimethylaminoethyloxy)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(2,2-dimethylpropoxy)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[(1-methyl-4-piperidyl)oxy]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(4-tetrahydropyran-4-yloxy-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(oxetan-3-yloxy)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide; and

N-[3-[4-(hydroxymethyl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide

or a pesticidally acceptable salt thereof.

9. The compound of claim 8 , selected from the group consisting of: