Solvates of abscisic acid and liquid compositions containing abscisic acid

Patent metadata

Field	Value
Publication number	US-12338216-B2
Application number	US-202017777558-A
Country	US
Kind code	B2
Filing date	Oct 28, 2020
Priority date	Nov 19, 2019
Publication date	Jun 24, 2025
Grant date	Jun 24, 2025

Abstract

The invention relates to new modifications of abscisic acid, to liquid compositions of abscisic acid and to their use in agrochemical applications. The modifications and compositions of the invention contain abscisic acid in the form of a solvate with at least one N-alkyl pyrrolidone, wherein the N-alkyl group has 3 to 6 carbon atoms. These solvates enable formulations with high concentrations of abscisic acid.

First claim

The invention claimed is:

1. A solvate of abscisic acid with a N-substituted pyrrolidone of the formula (I)

wherein R is a linear or branched, saturated alkyl group with 3 to 6 carbon atoms.

2. The solvate according to claim 1 , wherein the solvate is in an amorphous state.

3. The solvate according to claim 1 , wherein the abscisic acid is the naturally occurring form (S)-(+)-abscisic acid.

4. An agrochemical composition comprising the solvate according to claim 1 .

5. A spray liquid formulation comprising the solvate according to claim 1 .

6. The spray liquid formulation according to claim 5 , further comprising one or more solvents selected from water, glycerin, a vegetable oil-based liquid carrier, and combinations of these.

7. A method of treating a plant, the method comprising contacting the plant with a composition comprising the solvate according to claim 1 .

8. A method for preparing the solvate according to claim 1 , the method comprising the steps of (i) dissolving a precursor molecule of abscisic acid in an N-substituted pyrrolidone of formula (I); and
(ii) generating abscisic acid in situ from the precursor molecule.

9. The solvate according to claim 1 , wherein the abscisic acid and the N-substituted pyrrolidone of the formula (I) are present in a stoichiometric ratio of 1:1.

10. The solvate according to claim 1 , wherein the N-substituted pyrrolidone of the formula (I) is N-n-butylpyrrolidone.

11. The solvate according to claim 10 , wherein the abscisic acid is (S)-(+)-abscisic acid.

12. The solvate according to claim 10 , wherein the solvate is characterized by a desolvation peak at an average of approximately 125° C., as determined by differential scanning calorimetry.

13. The solvate according to claim 10 , wherein the solvate is characterized by two peaks in a differential thermographic analyses curve at an average turning point of approximately 180° C. and 262° C.

14. The agrochemical composition according to claim 4 , wherein the composition comprises
a) 10 to 50% by weight, based on the total weight of the composition, of abscisic acid; and
b) 0.1 to 90% by weight, based on the total weight of the composition, of one or more N-substituted pyrrolidones of the formula (I).

15. The agrochemical composition according to claim 14 , wherein the composition comprises 10 to 40 wt % of a) and 10 to 90 wt % of b).

16. The agrochemical composition according to claim 14 , wherein the composition further comprises
c) 0 to 50% by weight, based on the total weight of the composition, of one or more co-solvents;
d) 0 to 50% by weight, based on the total weight of the composition, of one or more formulation auxiliaries; and
e) 0 to 50% by weight, based on the total weight of the composition, of one or more additional active ingredients.

17. The agrochemical composition according to claim 14 , wherein the composition comprises 10 to 50 wt % of a), 0.1 to 85 wt % of b), and at least 0.1 wt % of one or more of c), d), and e).

18. The agrochemical composition according to claim 17 , wherein the composition comprises from 0.1 to 30 wt % of c), from 0.1 to 40 wt % of d), and from 0.1 to 40 wt % of e).

19. The agrochemical composition according to claim 16 , wherein the one or more formulation auxiliaries is selected from the group consisting of acidifiers, adjuvants, dispersing agents, emulsifiers, photodegradation stabilizer, spontaneity agents, and wetting agents.

Assignees

• Clariant Int Ltd

Inventors

• Giessler-Geiss Stephanie
• Baur Peter
• Arnold Roland
• Neckermann Jennifer
• Staiger Siegfried
• Dario Luri Stefano Negrisiolo

Classifications

• A01N43/36

  five-membered rings · CPC title

• A01N25/06

  Aerosols · CPC title

• A01N37/42

  containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids · CPC title

• A01N25/02

  containing liquids as carriers, diluents or solvents · CPC title

• C07C59/90

  containing singly bound oxygen-containing groups · CPC title