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
Inventors
Viertelhaus, Martin • KOULELIS, Dennis • SEISER, Tobias • Zagar, Cyrill • ARMEL, Gregory • Steinbrenner, Ulrich • Parra Rapado, Liliana • PAEHLER, Saskia • Souillart, Laetitia
Assignees
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Publication Number
US-11311014-B2
Publication Date
2022-04-26
Expiration Date
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.
Core Innovation
The invention concerns 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, including stable crystalline forms identified as crystalline form A, crystalline form B, form C as mixtures of polymorphs, and also crystalline forms D and E. The crystalline forms are characterized by X-ray powder diffraction at 25 °C using Cu-Kα radiation, including specified reflection sets and associated 2θ values, and are further supported by melting/DSC behavior.
The invention also describes crystallization and production guidance intended to obtain high-purity discrete crystals of the polymorphs. The guidance includes crystallization from solution under specified conditions, including seeding and slow or controlled crystallization approaches, to obtain polymorph-defined material rather than amorphous material or mixtures.
The disclosed discrete crystalline forms, in particular crystalline form A and crystalline form B, are related to plant protection and herbicidal use. Herbicidal compositions are described in which crystalline form A and/or form B/C functions as component A and includes additional herbicide actives as component B from multiple modes of action classes, with optional safeners as component C and formulation types including suspension concentrate and other listed solid or granule formats.
Claims Coverage
The independent claims cover crystalline form A 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 defined by X-ray powder diffraction criteria and high wt. % purity, together with use for combating undesired plant growth and herbicidal compositions. Across the claim set, there are 3 inventive features.
Crystalline form A defined by X-ray powder diffraction reflections
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 crystalline form A, wherein in an X-ray powder diffraction diagram at 25 °C and Cu-Kα radiation it displays at least 3 specified reflections quoted as 2θ values.
Method for combating undesired plant growth
A method for combating undesired plant growth by using the specified ethyl compound on plants, their habitat, and/or on seeds.
Herbicidal composition with additional herbicide actives
A herbicidal composition containing an herbicidal active amount of the ethyl compound and at least one additional herbicidal active compound selected from specified herbicide classes or from listed other herbicides, including agriculturally acceptable salts or esters.
The claims center on crystalline form A defined by specified Cu-Kα X-ray powder diffraction reflection criteria and purity, and extend to combating undesired plant growth and to herbicidal compositions that combine the ethyl active with additional herbicidal active compounds, including non-aqueous suspension concentrate formulations.
Stated Advantages
Improve handling and formulation stability over amorphous material or mixtures.
Documented Applications
Plant protection, including herbicidal use, by combating undesired plant growth on plants, their habitat, and/or on seeds.
Herbicidal compositions comprising the crystalline forms as component A and additional herbicide actives as component B, optionally with safeners as component C, in suspension concentrate and other listed solid or granule formats.
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