Crystalline forms

Patent metadata

Field	Value
Publication number	US-11053201-B2
Application number	US-201916969798-A
Country	US
Kind code	B2
Filing date	Feb 11, 2019
Priority date	Feb 13, 2018
Publication date	Jul 6, 2021
Grant date	Jul 6, 2021

Abstract

The invention relates to crystalline forms of N-[2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide of formula (I), compositions comprising said crystalline forms and methods of their use as nematicides or fungicides.

First claim

The invention claimed is:

1. A crystalline form of N-[(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide of formula (I)

characterized by an X-ray powder diffraction pattern comprising four or more 2-theta angle values selected from the group of 6.1±0.2, 11.2±0.2, 14.0±0.2, 16.7±0.2, 17.2±0.2, 18.5±0.2, 20.8±0.2, 21.3±0.2, 22.3±0.2, 23.6±0.2, 23.9±0.2 and 24.5±0.2 at a temperature of 21-26° C.

2. The crystalline form according to claim 1 , characterized by an X-ray powder diffraction pattern comprising six or more 2-theta angle values selected from the group of 6.1±0.2, 11.2±0.2, 14.0±0.2, 16.7±0.2, 17.2±0.2, 18.5±0.2, 20.8±0.2, 21.3±0.2, 22.3±0.2, 23.6±0.2, 23.9±0.2 and 24.5±0.2 at a temperature of 21-26° C.

3. The crystalline form according to claim 1 ,
characterized by the following unit cell parameters:
a=15.52 ű0.01 Å, b=7.24 ű0.01 Å, c=16.64 ű0.01 Å, α=90°±0.01°, ß=105.03±0.01°, γ=90°±0.01°, Z=4.

4. The crystalline form according to claim 1 ,
wherein the melting peak is at about 65° C.

5. A crystalline form of cis-N-[2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide of formula (I)

characterized by an X-ray powder diffraction pattern comprising four or more 2-theta angle values selected from the group of 10.8±0.2, 14.5±0.2, 17.5±0.2, 19.0±0.2, 23.5±0.2, 24.5±0.2, 26.0±0.2, 30.2±0.2, 32.6±0.2, 33.3±0.2, 34.1±0.2 and 35.5±0.2 at a temperature of 21-26° C.

6. The crystalline form according to claim 5 , characterized by an X-ray powder diffraction pattern comprising six or more 2-theta angle values selected from the group of 10.8±0.2, 14.5±0.2, 17.5±0.2, 19.0±0.2, 23.5±0.2, 24.5±0.2, 26.0±0.2, 30.2±0.2, 32.6±0.2, 33.3±0.2, 34.1±0.2 and 35.5±0.2 at a temperature of 21-26° C.

7. The crystalline form according to claim 5 , wherein the melting peak is at about 85° C.

8. The crystalline form according to claim 5 , characterized by the following unit cell parameters:
a=7.27 ű0.01 Å, b=9.32 ű0.01 Å, c=14.11 ű0.01 Å, α=75.53°±0.01°, ß=87.03±0.01°, γ=71.48°±0.01°, Z=2.

9. An agricultural or pharmaceutical composition comprising the crystalline form according to claim 1 and at least one acceptable carrier or diluent.

10. The composition according to claim 9 , further comprising one or more insecticidally, acaricidally, nematicidally or fungicidally active agents.

11. A method of protecting crops of useful plants against damages caused by nematode pests, which comprises treating the plants or the locus thereof with a composition according to claim 9 .

12. A method of protecting a plant propagation material against damages caused by nematode pests, which comprises treating the material with a composition according to claim 9 .

13. A method of protecting crops of useful plants against damages caused by fungi, which comprises treating the plants or the locus thereof with a composition according to claim 9 .

14. A method of protecting plant propagation material against damages caused by fungi, which comprises treating this material with a composition according to claim 9 .

Assignees

• Syngenta Participations Ag

Inventors

• Hone John
• Jones Ian Kevin

Classifications

• A01P3/00

  Fungicides · CPC title

• A01P7/04

  Insecticides · CPC title

• A01P5/00

  Nematocides · CPC title

• C07D213/82 Primary

  in position 3 · CPC title

• A01N43/40

  six-membered rings · CPC title