# US 9,434,712 B2 · Processes for the preparation of pesticidal compounds

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- Number: US 9,434,712 B2
- Document ID: US9434712B2
- Status: Granted
- Kind: B2
- Application number: 14/988,786
- Filed: 2016-01-06
- Published: 2016-05-19
- Granted: 2016-09-06
- Earliest claimed: 2013-10-17
- Assignees: Dow AgroSciences LLC
- Applicants: Dow AgroSciences LLC
- Inventors: Qiang Yang; Beth Lorsbach; Gary Roth; Noormohamed M. Niyaz; Jeffrey Nissen; Ronald Ross, Jr.; Greg Whiteker; Carl DeAmicis; Kaitlyn Gray; Yu Zhang
- Web page: https://patentgrep.com/patent/US9434712B2

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- A01N 43/40: six-membered rings
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- C07D 213/77: Hydrazine radicals
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

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

## Claims

### Claim 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)

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 7)

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