Compositions and methods for blocking ethylene response in plants using 3-cyclopropyl-1-enyl-propanoic acid salt

• US 9,023,761 B2
• Filed: 07/17/2008
• Issued: 05/05/2015
• Est. Priority Date: 07/19/2007
• Status: Expired due to Fees

• Current Assignee: Yissum Research Development Company of the Hebrew University of Jerusalem Ltd. (Hebrew University of Jerusalem)
• Original Assignee: Yissum Research Development Company of the Hebrew University of Jerusalem Ltd. (Hebrew University of Jerusalem), North Carolina State University (University of North Carolina System)
• Inventors: Goren, Raffi, Apelbaum, Akiva, Goldschmidt, Eliezer, Huberman, Moshe, Riov, Joseph, Sisler, Edward C.
• Primary Examiner(s): Pak, John
• Assistant Examiner(s): Holt, Andriae M
• Application Number:
  US12/669,600
• Publication Number:
  US 20120004106A1
• Time in Patent Office: 2,483 Days
• Field of Search: 504/114, 504/320, 562/506, 562/510, 514/572
• US Class Current: 504/114
• CPC Class Codes: A01N 3/00 Preservation of plants or parts thereof, e.g. inhibiting evaporation, improvement of the appearance of leaves or protection against physical influences such as UV radiation using chemical compositions preservation or chemical ripening of fruit or vegetables A23B7/00; Grafting wax
• CPC Class Codes: A01N 3/02 Keeping cut flowers fresh chemically
• CPC Class Codes: A01N 37/06 Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
• CPC Class Codes: A23B 7/154 Organic compounds; Microorganisms; Enzymes

Abstract

The present invention discloses a method of inhibiting an ethylene response in a plant, comprising step of applying to at least one portion of the plant an effective ethylene response-inhibiting amount of a H1-cyclopropene-1-propanoic acid salt (CPAS). A method of prolonging the life of a cut flower, comprising applying to the cut flower an effective life-prolonging amount of CPAS and a method for the production a CPAS, comprising steps of (i) preparing 4-bromo-4-pentenoic acid or derivatives thereof; (ii) producing 1-cyclopropene-1-propanoic acid; and (iii), converting this acid into its water soluble salt, especially its sodium salt are presented. Additionally, a new family of water soluble CPAS inhibitors for ethylene response in a plant is disclosed.

Claims

1. A method of inhibiting an ethylene response in a plant, the method comprising applying to at least one portion of said plant an effective ethylene response-inhibiting amount of a water-soluble sodium salt of 3-(1-cyclopropenyl) propanoic acid, wherein said sodium salt of 3-(1-cyclopropenyl)propanoic acid is provided in an aqueous solution at a concentration of 0.1-200 μ

g/ml, and wherein said applying comprising preparing said aqueous solution of said sodium salt of 3-(1-cyclopropenyl)propanoic acid and applying said aqueous solution to the plant.

2. The method according to claim 1, wherein said applying is carried out by dipping at least a part of said plant in said solution.

3. The method according to claim 1, wherein said applying is carried out by spraying at least part of said plant with said solution.

4. The method according to claim 1, wherein said applying is carried out by irrigating or drop emitting at least a part of said plant with said solution.

5. The method according to claim 1, wherein said applying is carried out by brushing at least a part of said plant with said solution.

6. The method according to claim 1, wherein said ethylene response is fruit ripening.

7. The method according to claim 1, wherein said ethylene response is vegetable ripening.

8. The method according to claim 1, wherein said ethylene response is flower senescence.

9. The method according to claim 1, wherein said ethylene response is abscission.

10. The method according to claim 1, wherein said plant is a harvested fruit.

11. The method according to claim 1, wherein said plant is a harvested vegetable.

12. The method according to claim 1, additionally comprising admixing the sodium salt of 3-(1-cyclopropenyl) propanoic acid with a surfactant such that a surface-active aqueous solution containing said sodium salt of 3-(1-cyclopropenyl) propanoic acid is obtained.

13. The method according to claim 1, wherein said water soluble sodium salt of 3-(1-cyclopropenyl) propanoic acid is provided in the form of a powder.

14. A method of prolonging the life of a harvested fruit, the method comprising applying to the harvested fruit an effective life-prolonging amount of a water-soluble sodium salt of 3-(1-cyclopropenyl)propanoic acid, wherein said sodium salt of 3-(1-cyclopropenyl)propanoic acid is provided in an aqueous solution at a concentration of 0.1-200 μ

g/ml, and wherein said applying comprising preparing said aqueous solution of said sodium salt of 3-(1-cyclopropenyl)propanoic acid and applying said aqueous solution to the plant.

15. The method according to claim 14, wherein said applying is carried out by dipping at least a part of said harvested fruit in said solution.

16. The method according to claim 14, wherein said applying is carried out by spraying at least part of said harvested fruit with said solution.

17. The method according to claim 14, wherein said applying is carried out by brushing at least a part of said harvested fruit with said solution.

18. The method according to claim 14, wherein said applying is carried out by irrigating or drop emitting at least a part of said harvested fruit with said solution.

19. The method according to claim 14, wherein said water soluble sodium salt of 3-(1-cyclopropenyl) propanoic acid is provided in the form of a powder.

20. A method of prolonging the life of a cut flower, the method comprising applying to the cut flower an effective life-prolonging amount of a water-soluble sodium salt of 3-(1-cyclopropenyl)propanoic acid, wherein said sodium salt of 3-(1-cyclopropenyl)propanoic acid is provided in an aqueous solution at a concentration of 0.1-200 μ

g/ml, and wherein said applying comprising preparing said aqueous solution of said sodium salt of 3-(1-cyclopropenyl)propanoic acid and applying said aqueous solution to the plant.

21. The method according to claim 20, wherein said applying is carried out by dipping at least a part of said cut flower into said solution.

22. The method according to claim 20, wherein said applying is carried out by spraying at least part of said cut flower with said solution.

23. The method according to claim 20, wherein said applying is carried out by irrigating or drop emitting at least a part of said cut flower with said solution.

24. The method according to claim 20, wherein said applying is carried out by brushing at least a part of said cut flower with said solution.

25. The method according to claim 20, wherein said water soluble sodium salt of 3-(1-cyclopropenyl) propanoic acid is provided in the form of a powder.

26. A water soluble sodium salt of 3-(1-cyclopropenyl)propanoic acid.

27. The water soluble sodium salt of 3-(1-cyclopropenyl) propanoic acid according to claim 26, provided in the form of a powder.

28. A composition comprising the water soluble sodium salt of 3-(1-cyclopropenyl) propanoic acid according to claim 26, and a surfactant, wherein said water soluble salt is provided as a surface-active water soluble sodium salt of 3-(1-cyclopropenyl) propanoic acid.

29. A method of producing the water soluble sodium salt of 3-(1-cyclopropyl)propanoic acid according to claim 26, the method comprising (i) preparing 4-bromo-4-pentenoic acid or derivatives thereof;

(ii) reacting said 4-bromo-4-pentenoic acid or derivatives thereof with dibromocarbene to produce a 1,2,2-tribromocyclopropane compound, which is used to produce 3-(1-cyclopropenyl) propanoic acid; and

(iii) converting the 3-(1-cyclopropenyl) propanoic acid into its water soluble sodium salt.