# US 12,599,135 B2 · Composition and method for preparing N-phenylpyrazole-1-carboxamides

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- Number: US 12,599,135 B2
- Document ID: US12599135B2
- Status: Granted
- Kind: B2
- Application number: 18/017,275
- Filed: 2021-07-22
- Published: 2023-08-24
- Granted: 2026-04-14
- Earliest claimed: 2020-07-23
- Assignees: Fmc Corporation Fmc IP Technology GmbH
- Applicants: FMC Corporation; FMC Agro Singapore Pte. Ltd.
- Inventors: Kåre Søndergaard; Jack K. Vinther
- Web page: https://patentgrep.com/patent/US12599135B2

## CPC

- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01P 7/00: Arthropodicides
- A01N 25/02: containing liquids as carriers, diluents or solvents
- C07D 231/14: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- 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
- A01P: BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

An improved method is disclosed for preparing an organic pesticide of Formula 4-A from (1) a composition comprising: (a) a crystalline organic pesticide; (b and c) compounds of Formulae 1 and 2; (d) an amine base and (e) an aprotic solvent; (2) reacting with a sulfonyl chloride of Formula 3; and (3) allowing the mixture to proceed to an organic pesticide of Formula 4-A. wherein R1, R2, R3, R4, R5, R6, R7 and R8 are as defined in the disclosure.

## Claims

### Claim 1

A composition comprising:
(a) a crystalline organic pesticide, wherein the crystalline organic pesticide is a crystalline compound of Formula 4,
wherein
R1 is CH3;
R2 is CN;
R3 is CH3;
R4 is Br;
R5 is Cl;
R6 is H; and
Z is N;
(b) a carboxylic acid compound of Formula 1,
wherein
R4 is Br;
R5 is Cl;
R6 is H; and
Z is N;
(c) an aniline compound of Formula 2,
wherein
R1 is CH3;
R2 is CN;
R3 is CH3;
(d) an amine base and
(e) an aprotic solvent,
wherein the amount of crystalline compound of Formula 4 is 5 mol % to 30 mol % per mol of the carboxylic acid compound of Formula 1.

### Claim 2 (depends on 1)

The composition of claim 1 wherein the amine base is selected from optionally substituted pyridines.

### Claim 3 (depends on 1)

The composition of claim 1 wherein the amine base is 3-picoline.

### Claim 4 (depends on 1)

The composition of claim 1 wherein the aprotic solvent is acetonitrile.

### Claim 5 (depends on 1)

The composition of claim 1 wherein the amount of crystalline compound of Formula 4 is 10 mol % to 25 mol % per mol of the carboxylic acid compound of Formula 1.

### Claim 6 (depends on 1)

The method to prepare a compound of Formula 4-A,
wherein
R1 is CH3;
R2 is CN;
R3 is CH3;
R4 is Br;
R5 is Cl;
R6 is H; and
Z is N;
the method comprising the steps of:
(1) forming the composition of claim 1;
(2) reacting the composition of claim 1 with a sulfonyl chloride compound of Formula 3,
R8S(O)2Cl 3
wherein
R8 is carbon-based radical; and
(3) allowing the coupling of the acid activated mixture to proceed for the formation of a compound of Formula 4-A.

### Claim 7 (depends on 6)

The method of claim 6 wherein the sulfonyl chloride compound of Formula 3 is methanesulfonyl chloride.

### Claim 8 (depends on 6)

The method of claim 6 further comprising the step of:
(4) adding water to the reaction.

### Claim 9 (depends on 1)

The composition of claim 1 wherein the amount of the aprotic solvent is at least 600 mL aprotic solvent per mol of the carboxylic acid compound of Formula 1.

### Claim 10 (depends on 1)

The composition of claim 1 wherein the amount of the aprotic solvent is between 1800 to 600 mL aprotic solvent per mol of the carboxylic acid compound of Formula 1.

### Claim 11 (depends on 1)

The composition of claim 1 wherein the amount of the aprotic solvent is between 1200 to 600 mL aprotic solvent per mol of the carboxylic acid compound of Formula 1.