# US 11,897,847 B2 · Crystalline form of ethyl 2-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]acetate

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- Number: US 11,897,847 B2
- Document ID: US11897847B2
- Status: Granted
- Kind: B2
- Application number: 17/058,709
- Filed: 2019-05-29
- Published: 2021-07-08
- Granted: 2024-02-13
- Earliest claimed: 2018-06-13
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Martin Viertelhaus; Rolf Hellmann; Tobias Seiser; Cyrill Zagar; Gregory Armel; Ulrich Steinbrenner
- Web page: https://patentgrep.com/patent/US11897847B2

## CPC

- C07D 239/54: as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- 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
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present invention relates to one crystalline form A of ethyl 2-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]acetate, a process for the production of this crystalline form, formulations for plant protection and herbicidal compositions comprising such form A.

## Claims

### Claim 1

A crystalline form A of ethyl 2-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-pyrimidin-1-yl]phenoxy]phenoxy]acetate, which in an X-ray powder diffraction diagram at 25° C. and Cu-Kc radiation displays at least 3 of the following reflections, quoted as 2θ values: 10.0±0.2°, 11.2±0.2°, 11.5±0.2°, 11.9±0.2°, 12.6±0.2°, 14.4±0.2°, 15.3±0.2°, 16.3±0.2°, 17.6±0.2°, 18.1±0.2°, 19.0±0.2°, 19.2±0.2°, 20.3±0.2°, 20.9±0.2°, 21.5±0.2°, 21.9±0.2°, 22.4±0.2° 23.0±0.2°, 24.4±0.2°, 24.7±0.2°, 25.3±0.2°, 26.1±0.2°, and 29.1±0.2°.

### Claim 2 (depends on 1)

The crystalline form A as claimed in claim 1 with a content of ethyl 2-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]-phenoxy]acetate of at least 94 wt. %.

### Claim 3 (depends on 1)

Ethyl 2-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]acetate consisting of at least 90 wt. % of the crystalline form A as claimed in claim 1.

### Claim 4 (depends on 1)

A process for the production of the crystalline form A as claimed in claim 1, comprising:
i) preparation of a solution of ethyl 2-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]acetate,
ii) effecting a crystallization of ethyl 2-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]acetate.

### Claim 5 (depends on 1)

A plant protection agent containing ethyl 2-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]acetate which comprises at least 90 wt. % of the crystalline form A as claimed in claim 1, and one or more additives customary for the formulation of plant protection agents.

### Claim 6 (depends on 5)

The plant protection agent as claimed in claim 5 in the form of an aqueous suspension concentrate.

### Claim 7 (depends on 5)

The plant protection agent as claimed in claim 5 in the form of a non-aqueous suspension concentrate.

### Claim 8 (depends on 5)

The plant protection agent as claimed in claim 5 in the form of a powder or granules dispersible in water.

### Claim 9 (depends on 1)

A method for combating undesired plant growth, wherein ethyl 2-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]acetate comprising at least 90 wt. % of the crystalline form A as claimed in claim 1 is used on plants, the habitat thereof and/or on seeds.