IP Library Granted Patent US 9,867,370
Granted Patent B2
US 9,867,370 · App. 14/760,815 · Granted Jan 16, 2018

Compositions and methods for stabilizing cyclopropene in solutions

Inventors: Jeffrey Alan Coles (Brown Mills, NJ); Yueqian Zhen (Paoli, PA)
Assignee: AGROFRESH INC.
A01N27/00A01N3/02A01N25/02A01N25/22A01N43/16A23B7/154A23V2002/00
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Quick Facts
Patent No.
US 9,867,370
App. No.
14/760,815
Granted
Jan 16, 2018
Kind
B2
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.

Claims (26)

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.

Assignments (6)
AGREEMENT OF AGENT RESIGNATION, APPOINTMENT AND ACCEPTANCE & MASTER ASSIGNMENT OF SECURITY DOCUMENTS Recorded Jun 24, 2024
From: JPMORGAN CHASE BANK, N.A.
To: ALTER DOMUS US LLC
Reel/Frame 067914/0941 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT REEL 053316, FRAME 0561 Recorded Apr 3, 2023
From: BANK OF MONTREAL
To: AGROFRESH, INC.
Reel/Frame 063238/0901 →
SECURITY INTEREST Recorded Mar 31, 2023
From: AGROFRESH INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063214/0683 →
PATENT SECURITY AGREEMENT Recorded Jul 27, 2020
From: AGROFRESH, INC.
To: BANK OF MONTREAL, AS COLLATERAL AGENT
Reel/Frame 053316/0561 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 7, 2016
From: COLES, JEFFREY A.; ZHEN, YUEQIAN
To: AGROFRESH INC.
Reel/Frame 038221/0854 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 28, 2016
From: COLES, JEFFREY A.; ZHEN, YUEQIAN
To: AGROFRESH INC.
Reel/Frame 037611/0402 →
Continuity (2)
Provisional Application 61752611 · Jan 15, 2013
Related Publication 20160000072A1 · Jan 7, 2016