Processes for the preparation of pesticidal compounds

• US 9,102,655 B2
• Filed: 10/17/2014
• Issued: 08/11/2015
• 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, Whiteker, Gregory T., Roth, Gary, DeAmicis, Carl, Clark, Thomas P., Gray, Kaitlyn, Zhang, Yu, Muhuhi, Joseck M., Canturk, Belgin, Kane, Elisabeth J.
• Primary Examiner(s): Morris, Patricia L
• Application Number:
  US14/517,600
• Publication Number:
  US 20150112076A1
• Time in Patent Office: 298 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 comprising:

(a) halogenating and reducing 4-nitropyrazole to produce

2. The process according to claim 1, wherein R¹ is C₁-C₄ haloalkyl.

3. The process according to claim 1, wherein R¹ is CH₂CH₂CF₃.

4. The process according to claim 1, wherein R¹ is CH₂(2,2-difluorocyclopropyl).

5. The process according to claim 1 further comprising oxidizing 1(e) with an oxidizing agent comprising hydrogen peroxide to yield

6. The process according to claim 1, wherein R¹ is CH₂CH₂CF₃ and the suitable activated carboxylic acid, carboxylic acid anhydride, or acid chloride of a carboxylic acid is prepared from