Processes for the preparation of pesticidal compounds

• US 9,540,342 B2
• Filed: 01/06/2016
• Issued: 01/10/2017
• Est. Priority Date: 10/17/2013
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Yang, Qiang, Lorsbach, Beth, Whiteker, Gregory, Roth, Gary, DeAmicis, Carl, Clark, Thomas, Gray, Kaitlyn, Canturk, Belgin, Kane, Elisabeth J., Zhang, Yu, Muhuhi, Joseck M.
• Primary Examiner(s): Morris, Patricia L
• Application Number:
  US14/989,295
• Publication Number:
  US 20160152594A1
• Time in Patent Office: 370 Days
• Field of Search: 546/275.4
• US Class Current: 1/1
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 321/14 of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 321/16 of a saturated carbon skeleton containing rings
• CPC Class Codes: C07D 231/38 Nitrogen atoms nitro radicals C07D231/16
• CPC Class Codes: C07D 231/40 Acylated on said nitrogen atom
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond

Abstract

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

Claims

1. A process for the preparation of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide (1c)

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

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

4. The process of claim 2, wherein the halopyridine is 3-iodopyridine.

5. The process of claim 1, wherein the base is an inorganic base.

6. The process of claim 5, wherein the inorganic base is K₃PO₄.

7. The process of claim 1, wherein the anime N,N′

-dimethylethane-1,2-diamine.

8. The process of claim 1, wherein the copper salt is selected from the group consisting of copper(I) chloride (CuCl), copper(II) chloride (CuCl₂) and copper(I) iodide (CuI).

9. The process of claim 8, wherein the copper salt is CuCl.

10. The process of claim 8, wherein the copper salt is CuCl₂.

11. The process of claim 8, wherein the copper salt is CuI.

12. The process of claim 1, wherein the step of reacting is carried out in the presence of a polar solvent.

13. The process of claim 12, wherein the polar solvent is acetonitrile, dioxane or DMF.