Processes for the preparation of pesticidal compounds

• US 9,862,702 B2
• Filed: 04/27/2017
• Issued: 01/09/2018
• Est. Priority Date: 10/17/2013
• Status: Active Grant

• 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, Jr., Ronald, Whiteker, Greg, DeAmicis, Carl, Gray, Kaitlyn, Zhang, Yu
• Primary Examiner(s): Morris, Patricia L
• Application Number:
  US15/498,691
• Publication Number:
  US 20170226078A1
• Time in Patent Office: 257 Days
• Field of Search: 5462754
• 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 dehydrocyanating 3-chloro-1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole-5-carbonitrile (6b) in the presence of a base, to yield 3-(3-chloro-1H-pyrazol-1-yl)pyridine (5b)

2. The process of claim 1, wherein the base is an organic base.

3. The process of claim 1, wherein the base is 1, 8-diazabicyclo-[5.4.0] undec-7-ene (DBU) or 1,5-diazabicyclo [4.3.0] non-5-ene (DBN).

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

5. The process of claim 1, wherein the base is potassium hydroxide.

6. The process of claim 1, wherein the dehydrocyanating is conducted in the presence of a polar solvent.

7. The process of claim 2, wherein the dehydrocyanating is conducted in the presence of a polar solvent.

8. The process of claim 4, wherein the dehydrocyanating is conducted in the presence of a polar solvent.

9. The process of claim 1, wherein the dehydrocyanating is conducted in the presence of a polar solvent selected from the group consisting of N,N-dimethyl-formamide (DMF), ethanol (EtOH), and tetrahydrofuran (THF).

10. The process of claim 2, wherein the dehydrocyanating is conducted in the presence of a polar solvent selected from the group consisting of N,N-dimethyl-formamide (DMF), ethanol (EtOH), and tetrahydrofuran (THF).

11. The process of claim 4, wherein the dehydrocyanating is conducted in the presence of a polar solvent selected from the group consisting of N,N-dimethyl-formamide (DMF), ethanol (EtOH), and tetrahydrofuran (THF).

12. The process of claim 1, wherein the dehydrocyanating is conducted at a temperature of from about −

10°

C. to about 30°

C.

13. The process of claim 2, wherein the dehydrocyanating is conducted at a temperature of from about −

10°

C. to about 30°

C.

14. The process of claim 4, wherein the dehydrocyanating is conducted at a temperature of from about −

10°

C. to about 30°

C.

15. The process of claim 7, wherein the dehydrocyanating is conducted at a temperature of from about −

10°

C. to about 30°

C.

16. The process of claim 8, wherein the dehydrocyanating is conducted at a temperature of from about −

10°

C. to about 30°

C.