IP Library › Granted Patent US 10,772,331

Granted Patent B2

US 10,772,331 · App. 16/420,627 · Granted Sep 15, 2020

Antiparasitic compounds

Inventors: Jason D. Speake (Winston-Salem, NC); Joe B. Perales (Durham, NC); Weiming Fan (Chapel Hill, NC); Solene Clarisse Rolland (Lyons, FR)

Assignee: Avista Pharma Solutions, Inc.

A01N43/90 A01N43/80 C07D491/107

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Quick Facts

Patent No.: US 10,772,331
App. No.: 16/420,627
Granted: Sep 15, 2020
Kind: B2

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Abstract

The present invention relates to isothiazoline compounds of formula (I). The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to veterinary compositions comprising said compounds.

Claims (159)

1. A method for treating or preventing a parasitic infection or infestation on a plant in need thereof, comprising treating the plant with a compound of Formula (I), or a pesticidal acceptable salt thereof:

wherein

each R 1A , R 1B , and R 1C individually is hydrogen, alkyl, halogen, or haloalkyl;

R 2 is haloalkyl;

X is bond, C(O), SO 2 , or C(O)NH;

R 3 is hydrogen, optionally substituted alkyl, optionally substituted haloalkyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl.

2. The method of claim 1 , wherein:

each R 1A , R 1B , and R 1C individually is halogen, haloalkyl, or alkyl;

R 2 is haloalkyl;

X is a bond, C(O), SO 2 , or C(O)NH; and

R 3 is alkyl, haloalkyl, or aryl.

3. The method of claim 1 , wherein:

each R 1A , R 1B , and R 1C individually is halogen;

R 2 is perfluoroalkyl;

X is —C(O)—, —SO 2 —, or —C(O)NH—; and

R 3 is haloalkyl.

4. The method of claim 1 , wherein:

each R 1A and R 1C is a halogen and R 1B is a different halogen;

R 2 is haloalkyl;

X is —C(O)—; and

R 3 is haloalkyl.

5. The method of claim 1 , wherein:

each R 1A and R 1C is —Cl and R 1B is —F;

R 2 is —CF 3 ;

X is —C(O)—; and

R 3 is haloalkyl.

6. The method of claim 1 , wherein:

each R 1A and R 1C is —Cl and R 1B is —F;

R 2 is —CF 3 ;

X is a bond, C(O), SO 2 , or C(O)NH; and

7. The method of claim 1 , wherein R 3 is alkyl; alkyl substituted with one or more alkoxy, alkylsulfonyl, cyano, or aryl; haloalkyl; cycloalkyl; cycloalkyl substituted with one or more alkyl, alkenyl, haloalkyl, haloalkenyl, alkoxy, or ═O; heterocyclyl; aryl; aryl substituted with one or more halogen; or heteroaryl.

8. The method of claim 1 , wherein the compound is selected from:

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-3,3,3-trifluoro-propan-1-one;

6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-N-(2,2,2-trifluoroethyl)spiro[1H-isobenzofuran-3,3′-azetidine]-1′-carboxamide;

6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-1′-(4-fluorophenyl)sulfonyl-spiro[1H-isobenzofuran-3,3′-azetidine];

[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-phenyl-methanone;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-2-methylsulfonyl-ethanone;

6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine];

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-3,3-dimethyl-butan-1-one;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]butan-1-one;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-2-phenyl-ethanone;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-4,4,4-trifluoro-butan-1-one;

[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-(1-naphthyl)methanone;

[(3Z,4Z)-4-allylidene-3-ethylidene-cyclohexa-1,5-dien-1-yl]-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]methanone;

[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-(4-morpholinophenyl)methanone;

6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-1′-propylsulfonyl-spiro[1H-isobenzofuran-3,3′-azetidine];

6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-1′-(3,3,3-trifluoropropylsulfonyl)spiro[1H-isobenzofuran-3,3′-azetidine];

6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-N-ethyl-spiro[1H-isobenzofuran-3,3′-azetidine]-1′-carboxamide;

6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-N-phenyl-spiro[1H-isobenzofuran-3,3′-azetidine]-1′-carboxamide;

[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-[3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropyl]methanone;

[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-tetrahydropyran-4-yl-methanone;

1′-butyl-6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine];

6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-1′-(3,3-dimethylbutyl)spiro[1H-isobenzofuran-3,3′-azetidine];

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-2-methoxy-ethanone;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-2-isopropoxy-ethanone;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-2-ethoxy-ethanone;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-2-methyl-propan-1-one;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]propan-1-one;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]ethanone;

3-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-4-ethoxy-cyclobut-3-ene-1,2-dione;

3-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-3-oxo-propanenitrile;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-2,2,3,3,3-pentafluoro-propan-1-one;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-2,2-difluoro-propan-1-one;

[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-[1-(trifluoromethyl)cyclopropyl]methanone;

[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-[1-(trifluoromethyl)cyclobutyl]methanone;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-3,3,3-trifluoro-2,2-dimethyl-propan-1-one;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]pentan-1-one;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]hexan-1-one;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]heptan-1-one;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]octan-1-one;

1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]nonan-1-one;

6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-1′-pyrimidin-2-yl-spiro[1H-isobenzofuran-3,3′-azetidine]; and

6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-N-methyl-spiro[1H-isobenzofuran-3,3′-azetidine]-1′-carboxamide,

or a pesticidal acceptable salt thereof.

9. The method of claim 1 , wherein the compound is 1-[6-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]spiro[1H-isobenzofuran-3,3′-azetidine]-1′-yl]-3,3,3-trifluoro-propan-1-one or a pesticidal acceptable salt thereof.

10. A method for treating or preventing a parasitic infection or infestation on an interior or exterior surface in need thereof, comprising treating the interior or exterior surface with a compound of Formula (I), or a pesticidal acceptable salt thereof:

wherein

each R 1A , R 1B , and R 1C individually is hydrogen, alkyl, halogen, or haloalkyl;

R 2 is haloalkyl;

X is bond, C(O), SO 2 , or C(O)NH; and

11. The method of claim 10 , wherein:

each R 1A , R 1B , and R 1C individually is halogen, haloalkyl, or alkyl;

R 2 is haloalkyl;

X is a bond, C(O), SO 2 , or C(O)NH; and

R 3 is alkyl, haloalkyl, or aryl.

12. The method of claim 10 , wherein:

each R 1A , R 1B , and R 1C individually is halogen;

R 2 is perfluoroalkyl;

X is —C(O)—, —SO 2 —, or —C(O)NH—; and

R 3 is haloalkyl.

13. The method of claim 10 , wherein:

each R 1A and R 1C is a halogen and R 1B is a different halogen;

R 2 is haloalkyl;

X is —C(O)—; and

R 3 is haloalkyl.

14. The method of claim 10 , wherein:

each R 1A and R 1C is —Cl and R 1B is —F;

R 2 is —CF 3 ;

X is —C(O)—; and

R 3 is haloalkyl.

15. The method of claim 10 , wherein:

each R 1A and R 1C is —Cl and R 1B is —F;

R 2 is —CF 3 ;

X is a bond, C(O), SO 2 , or C(O)NH; and

16. The method of claim 10 , wherein

R 3 is alkyl; alkyl substituted with one or more alkoxy, alkylsulfonyl, cyano, or aryl; haloalkyl; cycloalkyl; cycloalkyl substituted with one or more alkyl, alkenyl, haloalkyl, haloalkenyl, alkoxy, or ═O; heterocyclyl; aryl; aryl substituted with one or more halogen; or heteroaryl.

17. The method of claim 10 , wherein the compound is selected from: