Synthesis methods, complexes and delivery methods for the safe and convenient storage, transport and application of compounds for inhibiting the ethylene response in plants

• US 6,313,068 B1
• Filed: 08/20/1999
• Issued: 11/06/2001
• Est. Priority Date: 08/20/1998
• Status: Expired due to Term

• Current Assignee: AgroFresh Inc. (AgroFresh Solutions, Inc.)
• Original Assignee: AgroFresh Inc. (AgroFresh Solutions, Inc.)
• Inventors: Daly, James, Kourelis, Bob
• Primary Examiner(s): Lambkin, Deborah C.
• Application Number:
  US09/367,654
• Time in Patent Office: 809 Days
• Field of Search: 504/114, 504/115, 504/320, 504/326, 504/353, 504/356, 585/23, 585/365, 585/379, 585/380
• US Class Current: 504/114
• CPC Class Codes: A01N 2300/00 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 Class Codes: A01N 25/08 containing solids as carriers or diluents
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 25/18 Vapour or smoke emitting compositions with delayed or sustained release
• CPC Class Codes: A01N 27/00 Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
• CPC Class Codes: A01N 3/02 Keeping cut flowers fresh chemically
• CPC Class Codes: A01N 33/26 containing nitrogen-to-nitrogen bonds, e.g. azides, diazo-amino compounds, diazonium compounds, hydrazine derivatives
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: A01N 61/00 Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action

Abstract

The present invention generally relates to the regulation of plant physiology, in particular to methods for inhibiting the ethylene response in plants or plant products, and has three embodiments. The first embodiment relates to methods of minimizing impurities capable of reversibly binding to plant ethylene receptor sites during the synthesis of cyclopropene and its derivatives such as methylcyclopropene, thereby avoiding the negative effects these impurities have on plants treated with cyclopropene and its derivatives. The second embodiment relates to complexes formed from molecular encapsulation agents such as cyclodextrin, and cyclopropene and its derivatives such as methylcyclopropene, in addition to cyclopentadiene and diazocyclopentadiene and their derivatives, thereby providing a convenient means for storing and transporting these compounds capable of inhibiting the ethylene response in plants, which are reactive gases and highly unstable because of oxidation and other potential reactions. The third embodiment relates to convenient methods of delivering to plants these compounds capable of inhibiting the ethylene response in the plants in order to extend their shelf life.

Claims

1. A complex formed from a molecular encapsulation agent and a compound having the following structure

wherein n is a number from 1 to 10 and R is selected from the group consisting of hydrogen, saturated or unsaturated C1 to C10 alkyl, hydroxy, halogen, C1 to C10 alkoxy, amino and carboxy.

2. The complex of claim 1 wherein the molecular encapsulation agent is selected from the group consisting of a cyclodextrin, a crown ether, a polyoxyalkylene, a prophorine, a polysiloxane, a phophazene and a zeolite.

3. The complex of claim 1 wherein the compound is selected from the group consisting of cyclopropene and dimethylcyclopropene.

4. The complex of claim 1 wherein the molecular encapsulation agent is cyclodextrin.

5. The complex of claim 4 wherein the cyclodextrin is alpha-cyclodextrin.

15. The complex of claim 1 wherein n is a number from 5-10 and R is selected from the group consisting of hydrogen, saturated or unsaturated C5 to C10 alkyl, hydroxy, halogen, C5 to C10 alkoxy, amino and carboxy.

16. The complex of claim 15 wherein the molecular encapsulation agent is selected from the group consisting of a cyclodextrin, a crown ether, a polyoxyalkylene, a prophorine, a polysiloxane, a phosphazene and a zeolite.

17. The complex of claim 15 wherein the compound is selected from the group consisting of cyclopropene and dimethylcyclopropene.

18. The complex of claim 15 wherein the molecular encapusulation agent is cyclodextrin.

19. The complex of claim 18 wherein the cyclodextrin is alpha-cyclodextrin.

6. A method of delivering a compound to a plant to inhibit an ethylene response in the plant, the method comprising the step of contacting a complex formed from a molecular encapsulation agent and a compound having the following structure

wherein n is a number from 1 to 10 and R is selected from the group consisting of hydrogen, saturated or unsaturated C1 to C10 alkyl, hydroxy, halogen, C1 to C10 alkoxy, amino and carboxy, with a solvent capable of dissolving the molecular encapsulation agent, and thereby liberating the compound from the molecular encapsulation agent so that it can contact the plant.

7. The method of claim 6 wherein the molecular encapsulation agent is selected from the group consisting of a cyclodextrin, a crown ether, a polyoxyalkylene, a prophorine, a polysiloxane, a phophazene and a zeolite.

8. The method of claim 6 wherein the compound is selected from the group consisting of cyclopropene and dimethylcyclopropene.

9. The method of claim 6 wherein the molecular encapsulation agent is cyclodextrin.

10. The method of claim 9 wherein the cyclodextrin is alpha-cyclodextrin.

11. The method of claim 6 wherein the solvent comprises water.

12. The method of claim 11 wherein the water additionally comprises an acidic or alkaline agent.

13. The method of claim 6 further comprising bubbling a gas through the solvent while it is in contact with the complex.

14. The method of claim 6 further comprising applying heat to the solvent either before it contacts the complex or during that contact.