Processes for the preparation of pesticidal compounds

• US 9,434,712 B2
• Filed: 01/06/2016
• Issued: 09/06/2016
• Est. Priority Date: 10/17/2013
• Status: Expired due to Fees

• Current Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Yang, Qiang, Lorsbach, Beth, Roth, Gary, Niyaz, Noormohamed M., Nissen, Jeffrey, Ross, Ronald Jr., Whiteker, Greg, DeAmicis, Carl, Gray, Kaitlyn, Zhang, Yu
• Primary Examiner(s): Morris, Patricia L
• Application Number:
  US14/988,786
• Publication Number:
  US 20160137625A1
• Time in Patent Office: 244 Days
• Field of Search: 546/275.4
• US Class Current: 1/1
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: C07D 213/77 Hydrazine radicals
• 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 comprising reacting (E)-2-(2-(pyridin-3-yl)hydrazono)acetic acid (6a) with acrylonitrile and a source of chlorine, in the presence of a base, to yield 3-chloro-1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole-5-carbonitrile (6b)

2. The process of claim 1, wherein the source of chlorine is N-chlorosuccinimide.

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

4. The process of claim 1, wherein the base is a metal carbonate, metal hydroxide, metal phosphate, or metal hydride.

5. The process of claim 1, wherein the base is a metal carbonate.

6. The process of claim 1, wherein the base is potassium bicarbonate.

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

8. The process of claim 7, wherein the polar aprotic solvent is ethyl acetate.