Heterocyclic compounds as pesticides

Patent metadata

Field	Value
Publication number	US-10271552-B2
Application number	US-201615741758-A
Country	US
Kind code	B2
Filing date	Jul 5, 2016
Priority date	Jul 6, 2015
Publication date	Apr 30, 2019
Grant date	Apr 30, 2019

Abstract

The present application relates to thiadiazole compounds, compositions containing such compounds, their use for controlling animal pests including arthropods, insects and nematodes, and to processes and intermediates for the preparation of the thiadiazole compounds.

First claim

The invention claimed is:

1. A compound of formula (I-1)

in which
D represents a radical selected from the group consisting of

 in which the broken line represents the bond to the carbon atom in C=Q,
E represents hydrogen, a Li-, Na-, K-, Mg-, Ca-ion, or an ammonium ion of formula

 wherein R 5 , R 6 , R 7 and R 8 independently represent hydrogen, methyl, ethyl or benzyl,
Q represents oxygen,
R 1 represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl, trifluoromethyl, chloro-difluoromethyl, pentafluoroethyl, cyclopropyl, methoxy, ethoxy,-difluoromethoxy, trifluoromethoxy, chloro-difluoro-methoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, difluoroethylthio, trifluoroethylthio, methylsulphinyl, ethylsulphinyl, trifluoromethylsulphinyl, difluoromethylsulphinyl, difluoroethylsulphinyl, trifluoroethylsulphinyl, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, difluoromethylsulphonyl, difluoroethylsulphonyl, or trifluoroethylsulphonyl,
R 2 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl, trifluoromethyl, chloro-difluoromethyl, pentafluoroethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, chloro-difluoro-methoxy, difluoroethoxy, trifluoroethoxy methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, difluoroethylthio, trifluoroethylthio, trifluoromethylsulphinyl, difluoromethylsulphinyl, difluoroethylsulphinyl, trifluoroethylsulphinyl, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, difluoromethylsulphonyl, difluoroethylsulphonyl, or trifluoroethylsulphonyl,
R 3 represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl, trifluoromethyl, chloro-difluoromethyl, pentafluoroethyl, cyclopropyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, chloro-difluoro-methoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, difluoroethylthio, trifluoroethylthio, methylsulphinyl, ethylsulphinyl, trifluoromethylsulphinyl, difluoromethylsulphinyl, difluoroethylsulphinyl, trifluoroethylsulphinyl, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, difluoromethylsulphonyl, difluoroethylsulphonyl, or trifluoroethylsulphonyl, and
R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, nitro, cyano, methyl, ethyl, difluoromethyl, trifluoromethyl, chloro-difluoromethyl, pentafluoroethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, chloro-difluoro-methoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, difluoroethylthio, trifluoroethylthio, trifluoromethylsulphinyl, difluoromethylsulphinyl, difluoroethylsulphinyl, trifluoroethylsulphinyl, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, difluoromethylsulphonyl, difluoroethylsulphonyl, or trifluoroethylsulphonyl.

2. A composition comprising at least one compound according to claim 1 and one or more extenders and/or surfactants.

3. A method for controlling one or more pests, comprising allowing a compound of the formula (I) according to claim 1 to act on the pests and/or a habitat thereof, provided that methods for the therapeutic treatment of an animal body are excluded.

4. A method for controlling one or more arthropodal parasites on animals, comprising allowing a compound of the formula (I) according to claim 1 to act on the parasites and/or a habitat thereof.

5. A compound according to claim 1 , wherein R 1 is chlorine, fluorine, difluoromethyl, or trifluoromethyl.

6. A compound according to claim 1 , wherein D is B-1.

7. A compound according to claim 1 , wherein D is B-2.

8. A compound according to claim 1 , wherein D is B-3.

9. A compound according to claim 1 , wherein D is B-7.

10. A compound according to claim 1 , wherein D is B-8.

11. A compound according to claim 1 , wherein D is B-12.

12. A compound according to claim 5 , wherein D is B-3.

13. A compound according to claim 1 , wherein R 3 is chlorine, fluorine, difluoromethyl, or trifluoromethyl.

14. A compound according to claim 12 , wherein R 3 is chlorine, fluorine, difluoromethyl, or trifluoromethyl.

15. A compound according to claim 14 , wherein R 4 is hydrogen.

16. A compound according to claim 1 , of the structure

17. A compound according to claim 1 of the structure

18. A compound according to claim 1 of the structure

19. A compound according to claim 1 of the structure

20. A compound according to claim 1 , which is N-[3-(2,6-difluorophenyl)-1,2,4-thiadiazol-5-yl]-2-(trifluoromethyl)benzamide.

21. A compound according to claim 1 , which is N-[3-(2,6-difluorophenyl)-1,2,4-thiadiazol-5-yl]-3-(trifluoromethyl)pyrazine-2-carboxamide.

22. A compound according to claim 1 , which is 2-(difluoromethyl)-N-[3-(2,6-difluorophenyl)-1,2,4-thiadiazol-5-yl]nicotinamide.

23. A compound according to claim 1 , which is 2-(trifluoromethyl)-N-{3-[2-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl}nicotinamide.

24. A compound according to claim 1 , which is 2-chloro-N-[3-(2,6-difluorophenyl)-1,2,4-thiadiazol-5-yl]nicotinamide.

25. A compound according to claim 1 , which is sodium 3-(2,6-difluorophenyl)-N-{[2-(trifluoromethyl)pyridin-3-yl]carbonyl}-1,2,4-thiadiazol-5-aminide.

26. A compound according to claim 1 , which is N-[3-(2-chlorophenyl)-1,2,4-thiadiazol-5-yl]-2-(trifluoromethyl)nicotinamide.

27. A compound according to claim 1 , which is N-{3-[2-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl}-2-(trifluoromethyl)nicotinamide.

28. A compound according to claim 1 , which is N-{3-[4-fluoro-2-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl}-2-(trifluoromethyl)nicotinamide.

29. A compound according to claim 1 , which is N-{3-[3-fluoro-2-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl}-2-(trifluoromethyl)nicotinamide.

30. A compound according to claim 1 , which is N-{3-[2-chloro-3-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl}-2-(trifluoromethyl)nicotinamide.

31. A compound according to claim 1 , which is N-{3-[5-fluoro-2-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl}-2-(trifluoromethyl)nicotinamide.

Assignees

• Bayer Cropscience Ag

Inventors

• Schwarz Hans-Georg
• Decor Anne
• Greul Joerg
• Trautwein Axel
• Heilmann Eike Kevin
• Fischer Reiner
• Loesel Peter
• Malsam Olga
• Portz Daniela
• Ilg Kerstin
• Sommer Herbert
• Eilmus Sascha
• Scharwey Melanie
• Lishchynskyi Anton
• Geibel Sven
• Goergens Ulrich
• Herbert Simon Anthony
• Turberg Andreas

Classifications

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A01N43/82 Primary

  five-membered rings with three ring hetero atoms · CPC title

• C07D417/14

  containing three or more hetero rings · CPC title

• C07D285/08 Primary

  1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles · CPC title

• C07D417/12

  linked by a chain containing hetero atoms as chain links · CPC title