Crystalline forms of ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate

Patent metadata

Field	Value
Publication number	US-11311014-B2
Application number	US-201816497938-A
Country	US
Kind code	B2
Filing date	Mar 27, 2018
Priority date	Mar 31, 2017
Publication date	Apr 26, 2022
Grant date	Apr 26, 2022

Abstract

The present invention relates to crystalline forms of ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6), herein after also referred to as “compound of formula (I)”.The invention also relates to a process for the production of these crystalline forms, formulations for plant protection and herbicidal compositions which contain one of these crystalline forms.

First claim

The invention claimed is:

1. An ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate, consisting of at least 90 wt. % of the crystalline form A, which in an X-ray powder diffraction diagram at 25° C. and Cu-Kα radiation displays at least 3 of the following reflections, quoted as °2θ values: 10.42±0.10, 12.65±0.10, 16.64±0.10, 18.09±0.10, 18.44±0.10, 19.41±0.10, 22.17±0.10, 23.61±0.10, 24.06±0.10, 24.88±0.10, 25.20±0.10, 26.17±0.10, 27.86±0.10, 29.08±0.10.

2. The ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate as claimed in claim 1 , wherein form A displays at least 5 of the following reflections, quoted as °2θ values: 10.42±0.10, 12.65±0.10, 16.64±0.10, 18.09±0.10, 18.44±0.10, 19.41±0.10, 22.17±0.10, 23.61±0.10, 24.06±0.10, 24.88±0.10, 25.20±0.10, 26.17±0.10, 27.86±0.10, 29.08±0.10.

3. The ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate as claimed in claim 1 , wherein form A displays at least 7 of the following reflections, quoted as °2θ values: 10.42±0.10, 12.65±0.10, 16.64±0.10, 18.09±0.10, 18.44±0.10, 19.41±0.10, 22.17±0.10, 23.61±0.10, 24.06±0.10, 24.88±0.10, 25.20±0.10, 26.17±0.10, 27.86±0.10, 29.08±0.10.

4. The ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate as claimed in claim 1 , wherein form A displays the following reflections, quoted as °2θ values: 10.42±0.10, 12.65±0.10, 16.64±0.10, 18.09±0.10, 18.44±0.10, 19.41±0.10, 22.17±0.10, 23.61±0.10, 24.06±0.10, 24.88±0.10, 25.20±0.10, 26.17±0.10, 27.86±0.10, 29.08±0.10.

5. The ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate as claimed in claim 1 , consisting of at least 98 wt. % of the crystalline form A.

6. The ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate as claimed in claim 1 , consisting of at least 99 wt. % of the crystalline form A.

7. The ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate as claimed in claim 1 , consisting of 100 wt. % of the crystalline form A.

8. A herbicidal composition comprising a herbicidal active amount of the ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate as claimed in claim 1 , and at least one further active compound selected from
B) herbicides of class b1) to b15):
b1) lipid biosynthesis inhibitors;
b2) acetolactate synthase inhibitors (ALS inhibitors);
b3) photosynthesis inhibitors;
b4) protoporphyrinogen-IX oxidase inhibitors,
b5) bleacher herbicides;
b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);
b7) glutamine synthetase inhibitors;
b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);
b9) mitosis inhibitors;
b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);
b11) cellulose biosynthesis inhibitors;
b12) decoupler herbicides;
b13) auxinic herbicides;
b14) auxin transport inhibitors; and
b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters;
including their agriculturally acceptable salts or esters thereof.

9. A plant protection agent comprising the ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate as claimed in claim 1 , and one or more additives customary for the formulation of plant protection agents.

10. The plant protection agent as claimed in claim 9 in the form of an aqueous suspension concentrate.

11. The plant protection agent as claimed in claim 9 in the form of a non-aqueous suspension concentrate.

12. The plant protection agent as claimed in claim 9 in the form of a powder or granules dispersible in water.

13. A method for combating undesired plant growth, wherein the ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate as claimed in claim 1 is used on plants, the habitat thereof and/or on seeds.

Assignees

• Basf Se

Inventors

• Viertelhaus Martin
• Koulelis Dennis
• Seiser Tobias
• Zagar Cyrill
• Armel Gregory
• Steinbrenner Ulrich
• Parra Rapado Liliana
• Paehler Saskia
• Souillart Laetitia

Classifications

• C07D401/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• A01N61/00

  Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action · CPC title

• A01N25/32

  Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions · CPC title

• A01N43/54 Primary

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title