Polymorphs

Patent metadata

Field	Value
Publication number	US-11104672-B2
Application number	US-201816955497-A
Country	US
Kind code	B2
Filing date	Dec 14, 2018
Priority date	Dec 19, 2017
Publication date	Aug 31, 2021
Grant date	Aug 31, 2021

Abstract

The present invention relates to solid forms of the insecticide of formula (I): compositions comprising the solid forms and methods of their use as insecticides.

First claim

What is claimed is:

1. A crystalline polymorph of the compound of formula IA

which has a powder X-ray diffraction pattern comprising at least three 2θ angle values selected from the group consisting of 6.0±0.2, 8.8±0.2, 9.4±0.2, 10.1±0.2, 11.9±0.2, 14.5±0.2, 15.9±0.2, 20.2±0.2, 20.7±0.2, 21.2±0.2, 21.7±0.2, 22.1±0.2 and 22.7±0.2.

2. The crystalline polymorph of claim 1 , which has the following lattice parameters: a=5.06 ű0.01 Å, b=18.92 ű0.01 Å, c=24.17 ű0.01 Å, α=90°±0.01°, β=90°±0.01°, γ=90°±0.01° and volume=2315 Å 3 ±1 Å 3 .

3. The crystalline polymorph of claim 1 , which has a melting point of 141° C.±2° C.

4. A crystalline polymorph of the compound of formula IA,

which is a hydrate and which has a powder X-ray diffraction pattern comprising at least three 2θ angle values selected from the group consisting of 4.4±0.2, 7.0±0.2, 8.7±0.2, 10.3±0.2, 11.0±0.2, 12.4±0.2, 12.7±0.2, 13.3±0.2, 14.1±0.2, 15.9±0.2, 17.1±0.2, 18.6±0.2, 19.0±0.2 and 19.6±0.2.

5. The crystalline polymorph of claim 4 , which has the following lattice parameters: a=8.03 ű0.01 Å, b=16.10 ű0.01 Å, c=20.37 ű0.01 Å, α=90°±0.01°, β=97.02°±0.01°, γ=90°±0.01° and volume=2615 Å 3 ±1 Å 3 .

6. A crystalline polymorph of the compound of formula IB or IC

which has a powder X-ray diffraction pattern comprising at least three 2θ angle values selected from the group consisting of 4.1±0.2, 8.3±0.2, 10.2±0.2, 12.4±0.2, 15.5±0.2, 16.5±0.2, 18.2±0.2, 18.4±0.2, 18.7±0.2, 19.0±0.2, 20.5±0.2, 21.0±0.2 and 21.4±0.2.

7. The crystalline polymorph of claim 6 , which has a melting point of 206° C.±2° C.

8. A crystalline polymorph of the racemate of the compounds of formula IA and

which has a powder X-ray diffraction pattern comprising at least three 2θangle values selected from the group consisting of 4.0±0.2, 8.1±0.2, 9.7±0.2, 11.1±0.2, 12.7±0.2, 15.3±0.2, 15.9±0.2, 16.2±0.2, 16.7±0.2, 18.4±0.2, 19.5±0.2, 19.8±0.2, 20.3±0.2, 21.8±0.2 and 23.9±0.2.

9. The crystalline polymorph of claim 8 , which has a melting point of 173° C.±2° C.

10. An agricultural composition comprising a polymorph as claimed in claim 1 and at least one agriculturally acceptable carrier or diluent.

11. The composition of claim 10 , which further comprises a polymorph of the compound of formula IB or IC

or a polymorph of the racemate of the compounds of formula IA and ID

12. The composition of claim 10 , which is enriched for a polymorph of the compound of formula IA.

13. The composition of claim 12 , wherein the polymorph of the compound of formula IA has the following lattice parameters: a=5.06 ű0.01 Å, b=18.92 ű0.01 Å, c=24.17 ű0.01 Å, α=90°±0.01°,β=90°±0.01°,γ90°±0.01° and volume=2315 Å 3 ±1 Å 3 .

14. The composition of claim 10 , which comprises at least one further insecticide or nematicide.

15. A method of preventing or controlling insect infection on plants or plant propagation material comprising treating the plant or plant propagation material with an insecticidally effective amount of an agricultural composition as claimed in claim 10 .

16. An agricultural composition comprising a polymorph as claimed in claim 6 and at least one agriculturally acceptable carrier or diluent.

17. A method of preventing or controlling insect infection on plants or plant propagation material comprising treating the plant or plant propagation material with an insecticidally effective amount of an agricultural composition as claimed in claim 16 .

18. An agricultural composition comprising a polymorph as claimed in claim 8 and at least one agriculturally acceptable carrier or diluent.

19. A method of preventing or controlling insect infection on plants or plant propagation material comprising treating the plant or plant propagation material with an insecticidally effective amount of an agricultural composition as claimed in claim 18 .

20. The composition of claim 11 , wherein:
the polymorph of the compound of formula IB or IC has a powder X-ray diffraction pattern comprising at least three 2θ angle values selected from the group consisting of 4.1±0.2, 8.3±0.2, 10.2±0.2, 12.4±0.2, 15.5±0.2, 16.5±0.2, 18.2±0.2, 18.4±0.2, 18.7±0.2, 19.0±0.2, 20.5±0.2, 21.0±0.2 and 21.4±0.2; and
the polymorph of the racemate of the compounds of formula IA and ID has a powder X-ray diffraction pattern comprising at least three 2θ angle values selected from the group consisting of 4.0±0.2, 8.1±0.2, 9.7±0.2, 11.1±0.2, 12.7±0.2, 15.3±0.2, 15.9±0.2, 16.2±0.2, 16.7±0.2, 18.4±0.2, 19.5±0.2, 19.8±0.2, 20.3±0.2, 21.8±0.2 and 23.9±0.2.

Assignees

• Syngenta Participations Ag

Inventors

• George Neil
• Jones Ian Kevin
• Hone John

Classifications

• C07D413/12 Primary

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

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07D261/04 Primary

  having one double bond between ring members or between a ring member and a non-ring member · CPC title

• A61K31/42 Primary

  Oxazoles · CPC title

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title