Crystallized forms of herbicides and their compositions

Abstract

The present invention relates to formula (I): [Formula 1] This relates to the solid form of the compound JPEG2026522965000015.jpg44160, compositions containing this solid form, and methods of using them as herbicides.

Claims

1. Formula (I), referred to as Form 1 【Chemistry 1】 A crystalline polymorph of the compound, with the following lattice parameters: a = 55.3 Å ± 0.5 Å, b = 9.4 Å ± 0.5 Å, c = 24.9 Å ± 0.5 Å, α = 90° ± 0.1°, β = 98.6° ± 0.1°, γ = 90° ± 0.1°, and volume = 12728 Å 3 ±127 Å 3 A crystalline polymorph possessing the following characteristics.

2. The polymorph is characterized by a powder X-ray diffraction pattern expressed with respect to the 2θ angle, and the powder X-ray diffraction pattern is a) At least one 2θ angular value in 6.5 ± 0.2, b) At least one 2θ angular value in 7.2 ± 0.2, c) At least one 2θ angular value in 7.4 ± 0.2, and d) At least one, preferably two, more preferably three, and more preferably four 2θ angular values ​​selected from the group including 8.9±0.2, 12.9±0.2, 14.3±0.2, 14.8±0.2, 16.1±0.2, 17.3±0.2, 19.4±0.2, 20.5±0.2, 23.5±0.2, 25.0±0.2, 26.2±0.2, 28.2±0.2, and 29.4±0.2 A crystalline polymorph according to claim 1, including the above.

3. A crystalline polymorph according to claim 1 or claim 2, having a melting point of 81°C ± 5°C.

4. Formula (I), referred to as Form 2 【Chemistry 2】 A crystalline polymorph of the material, with the following lattice parameters: a = 57.7 Å ± 0.5 Å, b = 9.5 Å ± 0.5 Å, c = 24.9 Å ± 0.5 Å, α = 90° ± 0.1°, β = 96.0° ± 0.5°, γ = 90° ± 0.1°, and volume = 13532 Å 3 ±135 Å 3 It has the following steps: ix) Adding a mixture of methylcyclohexane and toluene to the compound of formula (I); x) Heat and stir the resulting mixture until the solid of the compound of formula (I) dissolves; xi) The step of gradually cooling the mixture so that an oil phase is formed; xi) The step of stirring the obtained oil phase until crystalline polymorphs are formed. A crystalline polymorph characterized by being prepared by the method described above.

5. The polymorph is further characterized by a powder X-ray diffraction pattern expressed with respect to the 2θ angle, and the powder X-ray diffraction pattern is a) At least one 2θ angular value in 6.1 ± 0.2, b) At least one 2θ angular value in 7.0 ± 0.2, and c) At least one, preferably two, more preferably three 2θ angular values ​​selected from the group including 10.9±0.2, 12.3±0.2, 13.5±0.2, 14.1±0.2, 14.7±0.2, 15.3±0.2, 15.9±0.2, 16.9±0.2, 17.1±0.2, 19.4±0.2, 19.7±0.2, 20.1±0.2, 20.4±0.2, 20.8±0.2, 21.4±0.2, 23.4±0.2, 24.1±0.2, 25.0±0.2, and 26.0±0.

2. A crystalline polymorph according to claim 4, including the above.

6. A crystalline polymorph according to claim 4 or claim 5, having a melting point of 70°C ± 5°C.

7. A pesticide composition, i) a polymorph referred to as form 1 according to any one of claims 1 to 3; ii) A polymorph referred to as form 2 according to any one of claims 4 to 6 An agricultural composition containing the following:

8. An agricultural composition comprising at least one polymorph according to any one of claims 1 to 6, further comprising an amorphous form of the compound of formula (I).

9. The agricultural composition according to claim 7, further comprising an amorphous form of the compound of formula (I).

10. An agricultural composition comprising a polymorph according to any one of claims 1 to 6 and at least one agriculturally acceptable carrier or diluent.

11. The composition according to claim 10, further comprising at least one herbicide.

12. The agricultural composition according to any one of claims 7 to 11, which is a suspension concentrate formulation.

13. Use of the polymorph according to any one of claims 1 to 6, or the composition according to any one of claims 7 to 12, on crops resistant to the compound of formula (I).

14. Use of a polymorph according to any one of claims 1 to 6, or a composition according to any one of claims 7 to 12, for controlling weeds that are resistant to PPO herbicides except for the compound of formula (I).

15. A method for controlling weeds in a crop of useful plants, comprising treating the useful plant, its seeds or cuttings, or the habitat of the useful plant simultaneously or separately with a composition containing the polymorph described in any one of claims 1 to 6, or a composition described in any one of claims 7 to 12.

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