Compositions and methods for stabilizing cyclopropene in solutions

Patent metadata

Field	Value
Publication number	US-9867370-B2
Application number	US-201414760815-A
Country	US
Kind code	B2
Filing date	Jan 14, 2014
Priority date	Jan 15, 2013
Publication date	Jan 16, 2018
Grant date	Jan 16, 2018

Abstract

This invention is based on surprising results that certain concentrations of certain sugars stabilize cyclopropene formulation in aqueous solutions. Provided are compositions comprising an aqueous solution of at least one cyclopropene and at least one sugar. Also provided are methods of using such compositions for inhibiting an ethylene response in a plant.

First claim

We claim:

1. A stable liquid composition comprising an aqueous solution of a cyclopropene molecular complex and at least one sugar,
wherein the cyclopropene molecular complex comprises a cyclopropene and a molecular encapsulating agent,
wherein the molecular encapsulating agent is selected from the group consisting of substituted cyclodextrins, unsubstituted cyclodextrins, crown ethers, zeolites, and combinations thereof, and
wherein the aqueous solution is at least 25% saturated with the at least one sugar.

2. The stable liquid composition of claim 1 , wherein the cyclopropene molecular complex is an inclusion complex.

3. The stable liquid composition of claim 2 , wherein the molecular encapsulating agent forms a cavity and the cyclopropene or a portion of the cyclopropene is located within the cavity.

4. The stable liquid composition of claim 1 , wherein the molecular encapsulating agent comprises a cyclodextrin.

5. The stable liquid composition of claim 4 , wherein the cyclodextrin is selected from the group consisting of alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, and combinations thereof.

6. The stable liquid composition of claim 1 , wherein the aqueous solution is 90-100% saturated with the at least one sugar.

7. The stable liquid composition of claim 1 , wherein the at least one sugar is selected from the group consisting of monosaccharides, disaccharides, and combinations thereof.

8. The stable liquid composition of claim 1 , wherein the at least one sugar comprises sucrose.

9. The stable liquid composition of claim 1 , wherein the cyclopropene is of the formula:

wherein R is a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl, or naphthyl group; wherein the substituents are independently halogen, alkoxy, or substituted or unsubstituted phenoxy.

10. The stable liquid composition of claim 9 , wherein R is C 1-8 alkyl.

11. The stable liquid composition of claim 9 , wherein R is methyl.

12. The stable liquid composition of claim 1 , wherein the cyclopropene is of the formula:

wherein R 1 is a substituted or unsubstituted C 1 -C 4 alkyl, C 1 -C 4 alkenyl, C 1 -C 4 alkynyl, C 1 -C 4 cycloalkyl, cylcoalkylalkyl, phenyl, or napthyl group; and R 2 , R 3 , and R 4 are hydrogen.

13. The stable liquid composition of claim 1 , wherein the cyclopropene is 1-methylcyclopropene (1-MCP).

14. A method of inhibiting an ethylene response in a plant, the method comprising treating the plant with the stable liquid composition of claim 1 .

15. The method of claim 14 , wherein the cyclopropene is part of a cyclopropene inclusion complex, the cyclopropene inclusion complex comprising a cyclopropene located in a cavity of the inclusion complex.

16. The method of claim 14 , wherein the aqueous solution is 90-100% saturated with the at least one sugar.

17. The method of claim 14 , wherein the cyclopropene is 1-methylcyclopropene (1-MCP).

18. A stable liquid composition comprising:
(a) an aqueous solution of at least one cyclopropene molecular complex comprising a cyclopropene and a molecular encapsulating agent selected from the group consisting of substituted cyclodextrins, unsubstituted cyclodextrins, crown ethers, zeolites, and combinations thereof; and
(b) at least one sugar selected from the group consisting of monosaccharides, disaccharides, trisaccharides, oligosaccharides, polysaccharides, and combinations thereof,
wherein the aqueous solution is at least 25% saturated with the at least one sugar.

Assignees

• Agrofresh Inc

Inventors

• Coles Jeffrey Alan
• Zhen Yueqian

Classifications

• A01N27/00 Primary

  Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons · CPC title

• A01N25/02

  containing liquids as carriers, diluents or solvents · CPC title

• A23B7/154

  Organic compounds; Microorganisms; Enzymes · CPC title

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title

• A01N25/22

  containing ingredients stabilising the active ingredients · CPC title