Processes for the preparation of pesticidal compounds

Patent metadata

Field	Value
Publication number	US-9447048-B2
Application number	US-201614989269-A
Country	US
Kind code	B2
Filing date	Jan 6, 2016
Priority date	Oct 17, 2013
Publication date	Sep 20, 2016
Grant date	Sep 20, 2016

Abstract

The present application provides processes for making pesticidal compounds and compounds useful both as pesticides and in the making of pesticidal compounds.

First claim

What is claimed is:

1. A process for the preparation of pesticidal thioethers (3b) useful in the preparation of pesticidal thioethers (3c) and pesticidal sulfoxides (3d),

wherein R 1 is selected form the group consisting of C 1 -C 4 haloalkyl and C 1 -C 4 alkyl-C 3 -C 6 halocycloalkyl which comprises heteroarylation of thioether (3a)

with a halopyridine in the presence of a copper salt, an amine, and a base.

2. The process of claim 1 , wherein the halopyridine is 3-bromopyridine.

3. The process of claim 1 , wherein the copper salt is selected from the group consisting of copper(I) chloride, copper(II) chloride, and copper(I) iodide.

4. The process of claim 2 , wherein the copper salt is selected from the group consisting of copper(I) chloride, copper(II) chloride, and copper(I) iodide.

5. The process of claim 1 , wherein the base is potassium phosphate or potassium carbonate.

6. The process of claim 4 , wherein the base is potassium phosphate or potassium carbonate.

7. The process of claim 1 , wherein the amine is N,N′-dimethylethane-1,2-diamine.

8. The process of claim 6 , wherein the amine is N,N′-dimethylethane-1,2-diamine.

9. The process of claim 1 , wherein the heteroarylation is carried out in a polar solvent.

10. The process of claim 9 , wherein the polar solvent is acetonitrile, dioxane or N,N-dimethylformamide.

11. The process of claim 8 , wherein the heteroarylation is carried out in a polar solvent.

12. The process of claim 11 , wherein the polar solvent is acetonitrile, dioxane or NN-dimethylformamide.

13. The process of claim 1 , wherein the heteroarylation is carried out at a temperature between about 50° C. and about 110° C.

14. The process of claim 12 , wherein the heteroarylation is carried out at a temperature between about 50° C. and about 110° C.

15. The process of claim 1 , wherein the R 1 is C 1 -C 4 haloalkyl.

16. The process of claim 15 , wherein C 1 -C 4 haloalkyl is 3,3,3-trifluoropropyl.

17. The process of claim 14 , wherein R 1 is C 1 -C 4 haloalkyl.

18. The process of claim 17 , wherein C 1 -C 4 haloalkyl is 3,3,3-trifluoropropyl.

19. The process of claim 1 , wherein C 1 -C 4 alkyl is ethyl.

20. The process of claim 18 , wherein C 1 -C 4 alkyl is ethyl.

Assignees

• Dow Agrosciences Llc

Inventors

• Yang Qiang
• Lorsbach Beth
• Whiteker Greg
• Deamicis Carl
• Gray Kaitlyn
• Zhang Yu
• Muhuhi Joseck M

Classifications

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D231/40 Primary

  Acylated on said nitrogen atom · CPC title

• C07D401/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D231/38

  Nitrogen atoms (nitro radicals C07D231/16) · CPC title

• A01N43/56 Primary

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title