Method for producing an aqueous suspension concentrate formulation of a pyripyropene insecticide

Patent metadata

Field	Value
Publication number	US-9861104-B2
Application number	US-201314383731-A
Country	US
Kind code	B2
Filing date	Mar 11, 2013
Priority date	Mar 12, 2012
Publication date	Jan 9, 2018
Grant date	Jan 9, 2018

Abstract

The present invention relates to a method for producing an aqueous suspension concentrate formulation and novel suspension concentrate formulations of the compound of formula I.

The method comprises:
a) providing an aqueous slurry of coarse particles of the compound of the formula I, where the compound of the formula I is at least partially present in its crystalline form B, which, in an X-ray powder diffractogram at 25° C. and Cu-K α radiation, shows at least three, preferably at least four, in particular at least 5 or at least 7 or at least 9 or all of the following reflexes, given as 2θ values: 8.0±0.2°, 9.5±0.2°, 10.7±0.2°, 11.0±0.2°, 11.2±0.2°, 11.7±0.2°, 14.2±0.2°, 15.6±0.2°, 16.5±0.2°, 17.7±0.2°, 21.5±0.2°; b) comminuting the coarse particles in the slurry of the compound of formula I, which is at least partially present in its form B, in the presence of the at least one surfactant.

First claim

We claim:

1. A method for producing an aqueous suspension concentrate formulation of a compound of formula I in the form of fine particles;

in which the fine particles contain the compound of formula I, at least one surfactant and water, which method comprises:
a) providing an aqueous slurry of coarse particles of the compound of the formula I, where the compound of the formula I is at least partially present in its crystalline form B, which, in an X-ray powder diffractogram at 25° C. and Cu-K α radiation, shows at least three of the following reflexes, given as 2θ values: 8.0±0.2°, 9.5±0.2°, 10.7±0.2°, 11.0±0.2°, 11.2±0.2°, 11.7±0.2°, 14.2±0.2°, 15.6±0.2°, 16.5±0.2°, 17.7±0.2°, 21.5±0.2°;
b) comminuting the coarse particles in the slurry of the compound of formula I, which is at least partially present in its form B, in the presence of the at least one surfactant;
except for a formulation containing from 6 to 20 wt %, based on the total weight of the formulation, of at least one anionic polymeric surfactant having a plurality of SO 3 − groups.

2. The method as claimed in claim 1 , which comprises;
a1) suspending a solid form of the compound of formula I, which is different from said form B, in water to obtain an aqueous slurry of coarse particles of the compound of formula I;
a2) keeping the aqueous slurry of coarse particles of the compound of formula I for a time sufficient to achieve at least partial conversion of the compound of formula I into its form B;
a3) addition of at least one surfactant during steps a1) or a2) or after step a2), and
b) comminuting the coarse particles in the slurry of the compound of formula I, which is at least partially present in its form B, after the addition of the at least one surfactant.

3. The method as claimed in claim 2 , where the major amount of surfactant is added after completion of step a2.

4. The method as claimed in claim 2 , where the aqueous slurry of the coarse particles of the compound of formula I is kept until at least 70% by weight of the compound of the formula I, based on the total amount of the compound of formula I in the suspension, are present in the form B.

5. The method as claimed in claim 2 , where the at least partial conversion of the compound of formula I into its form B is achieved by keeping the aqueous slurry of the coarse particles of the compound of formula I for at least 0.5 h up to 8 days at a temperature in the range of from 25 to 95° C.

6. The method as claimed in claim 1 , where step b) is performed to achieve a volume average diameter of the particles of not more than 8 μm.

7. The method as claimed in claim 1 , where in the slurry the volume average diameter of the coarse particles is greater than 10 μm and up to 1000 μm.

8. The method as claimed in claim 1 , where in the slurry at least 70% by weight of the compound of the formula I, based on the total amount of the compound of formula I, are present in the form B prior to comminution.

9. The method as claimed in claim 1 , where in step b) comminution of the coarse particles is performed at a temperature of not more than 50° C.

10. The method as claimed in claim 1 , where the concentration of the compound of formula I in the aqueous suspension during step b) is from 5 to 50% by weight, based on the total weight of the suspension.

11. The method as claimed in claim 1 , where the concentration of the at least one surfactant in the aqueous suspension during step b) is from 1 to 30% by weight, based on the total weight of the aqueous suspension.

12. The method as claimed in claim 1 , where the compound of the formula I has a purity of at least 97%.

13. The method as claimed in claim 1 , where the surfactant comprises at least one anionic surfactant.

14. The method as claimed in claim 13 , where the anionic surfactant comprises at least one anionic polymeric surfactant having a plurality of SO 3 − groups.

15. The method as claimed in claim 13 , where the anionic polymeric surfactant having a plurality of SO 3 − groups is selected from the group consisting of salts of naphthalene sulfonic acid formaldehyde condensates, salts of alkylnaphthalene sulfonic acid formaldehyde condensates, and the salts of naphthalene sulfonic acid formaldehyde urea co-condensates.

16. The method as claimed in claim 13 , where the surfactant further comprises at least one non-ionic surfactant.

17. The method as claimed in claim 16 , where the non-ionic surfactant is selected from poly(C 2 -C 4 )alkylenoxide polymers.

18. An aqueous suspension concentrate formulation of the compound of the formula I as defined in claim 1 , wherein the compound of the formula I is at least partially present in its form Y, which, in an X-ray powder diffractogram at 25° C. and Cu-K α radiation, shows at least three of the following reflexes, given as 2θ values: 9.7±0.2°, 10.3±0.2°, 11.3±0.2°, 14.0±0.2°, 15.5±0.2°, 16.4±0.2°, 17.6±0.2°.

19. The formulation of claim 18 , which contains
a) 1 to 30 wt %, based on the total weight of the formulation, of the pesticide compound of formula I, which is at least partially present in its form Y;
b) 0.1 to 20 wt %, based on the total weight of the formulation, of at least one anionic surfactant,
c) 0.1 to 20 wt %, based on the total weight of the formulation, of at least one non-ionic surfactant,
d) 40 to 98.8 wt %, based on the total weight of the formulation, by weight of water.

20. The formulation of claim 18 , where the volume average diameter of the pesticide particles is from 0.5 to 5 μm.

21. The formulation of claim 18 , where the anionic surfactant comprises at least one anionic polymeric surfactant having a plurality of SO 3 − groups.

22. The formulation of claim 21 , where the anionic polymeric surfactant having a plurality of SO 3 − groups is selected from the group consisting of salts of naphthalene sulfonic acid formaldehyde condensates, salts of alkylnaphthalene sulfonic acid formaldehyde condensates, and the salts of naphthalene sulfonic acid formaldehyde urea co-condensates.

23. The formulation of claim 18 , where the non-ionic surfactant is selected from poly(C 2 -C 4 )alkylenoxide polymers.

24. The formulation of claim 18 , where the non-ionic surfactant is selected from poly(ethyleneoxide-co-propyleneoxide) polymers having a HLB in the range of 12-20.

25. A method for protecting plants from attack or infestation by insects, acarids or nematodes comprising contacting the plant, or the soil or water in which the plant is growing, with an aqueous pesticide formulation according to claim 18 in pesticidally effective amounts.

26. A method for controlling insects, arachnids or nematodes comprising contacting an insect, acarid or nematode or their food supply, habitat, breeding grounds or their locus with an aqueous pesticide formulation according to claim 18 in pesticidally effective amounts.

27. A method for protection of plant propagation material comprising contacting the plant propagation material with an aqueous pesticide formulation according to claim 18 in pesticidally effective amounts.

28. Seed treated with the composition according to claim 18 .

29. The method as claimed in claim 6 , where step b) is performed to achieve a volume average dia

Assignees

• Basf Se

Inventors

• Knieriem Torsten
• Chiodo Tiziana
• Koradin Christopher
• Weber Tanja
• Weishaar Walter

Classifications

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• A01N53/00 Primary

  Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof · CPC title

• A01N25/08

  containing solids as carriers or diluents · CPC title

• A01N2300/00

  Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48 · CPC title

• A01N25/04

  Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16) · CPC title