Processes for the preparation of pesticidal compounds

• US 9,255,082 B2
• Filed: 05/20/2015
• Issued: 02/09/2016
• 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, Roth, Gary, DeAmicis, Carl, Clark, Thomas, Gray, Kaitlyn, Canturk, Belgin, Kane, Elisabeth J., Zhang, Yu, Muhuhi, Joseck M., Whiteker, Gregory
• Primary Examiner(s): Morris, Patricia L
• Application Number:
  US14/717,296
• Publication Number:
  US 20150252016A1
• Time in Patent Office: 265 Days
• Field of Search: 548/372.5
• 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 selective mono-acylation of 3-chloro-1H-pyrazol-4-amine hydrochloride (1a)

2. The method of claim 1, wherein the base is an inorganic base.

3. The process of claim 1, wherein the base is sodium bicarbonate.

4. The process of claim 1, wherein the acylating is carried out at a temperature of from about 0°

C. to about 10°

C.

5. The process of claim 4, wherein the acylating is carried out at a temperature of about 5°

C.

6. The process of claim 1, wherein the base is an inorganic base and the acylating is carried out at a temperature of from about 0°

C. to about 10°

C.

7. The process of claim 6, wherein the inorganic base is sodium bicarbonate and the temperature is about 5°

C.

8. The process of claim 1, further comprising halogenating and reducing 4-nitropyrazole

9. The process of claim 8, wherein the halogenating and reducing is conducted in a polar protic solvent.

10. The process of claim 9, wherein the polar protic solvent is methanol or ethanol.

11. The process of claim 8, wherein the triethylsilane is used in an amount of about 2.5 equivalents to about 3.5 equivalents.