Patent Application
20250017224
The invention relates to methods of treating a mixed type of produce with a cyclopropene. The invention also relates to methods of treating plant or plant parts in an environment comprising exogenous ethylene.
The presence of produce is a common sight in most refrigerators around the world. For example, produce can be found in the household refrigerators of most consumers as well as in industrial distribution centers, retailers, and restaurants. Further, the produce is typically present in the refrigerators in mixed types such that more than one type of produce can be found in the refrigerator at any given time. For instance, several different types of produce can be present as a mixed type in a single enclosure inside a refrigerator.
It is well known that produce exposed to exogenous ethylene results in ripening or undesired aging of the produce. For instance, exposure of produce to ethylene results in increased ripening of the produce, thus reducing the freshness of the produce. Furthermore, it is known the sensitivity of different types of produce to exogenous ethylene vary widely.
Importantly, produce itself gives off endogenous ethylene. However, the endogenous production of ethylene by different types of produce also varies widely. When several different types of produce are present as a mixed type in an enclosure, the various types of produce will give off endogenous ethylene at different rates.
One problem facing consumers that store a mixed type of different types of produce in an enclosure is the unpredictable ripening or undesired aging of the various produce. First, the different types of produce in the enclosure each have varying sensitivities to exogenous ethylene, resulting in uneven ripening or undesired aging of the types of produce in the enclosure. Second, the different types of produce in the enclosure each have different levels of endogenous ethylene production given off by the produce itself. As a result, a single enclosure including a variety of produce can present a challenging environment for the different types of produce to remain fresh for consumption. Thus, there is exists a need for consumers to be able to store different types of produce in an enclosure in which the produce can preserve quality and extend freshness.
Accordingly, the present disclosure provides methods of treating a mixed type of produce with a cyclopropene, as well as methods of treating plant or plant parts in an environment comprising exogenous ethylene methods with a cyclopropene. The methods described herein exhibit desirable properties and provide related advantages to benefit the quality and extend the freshness of produce and also reduce waste associated with the over-ripening or undesired aging of produce. For instance, when the mixed type of produce comprises fresh produce and over-ripened and/or aged produce, the cyclopropene can provide a preserving and/or extending quality of the fresh produce even in the presence of over-ripened and/or aged produce. Further, when the mixed type of produce comprises non-climacteric produce and climacteric produce, the cyclopropene can provide a preserving and/or extending quality of the non-climacteric produce even in the presence of climacteric produce. Finally, when the mixed type of produce comprises fresh produce and high ethylene-emitting produce, the cyclopropene can provide a preserving and/or extending quality of the fresh produce even in the presence of high ethylene-emitting produce.
Other objects, features and advantages of the present disclosure will become apparent from the following detailed description. It should be understood, however, that the detailed description and the specific examples, while indicating specific embodiments of the invention, are given by way of illustration only, since various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description.
The following numbered embodiments are contemplated and are non-limiting:
Various embodiments of the invention are described herein as follows. In one aspect described herein, a method of treating a mixed type of produce is provided. The method comprises administering a composition comprising a cyclopropene to the mixed type of produce.
As used herein, a “mixed type of produce” refers to at least two items of produce, including a first item of produce and a second item of produce that are not the same. For instance, at least two different types of produce are included in a “mixed type of produce.”
In an embodiment, the mixed type of produce comprises produce is present in an enclosed space or a partially enclosed space. For instance, the enclosed space/partially enclosed space can be a refrigerator.
In an embodiment, the composition comprising the cyclopropene is placed in the enclosed space/partially enclosed space. Any delivery method or delivery system associated with delivery of cyclopropene can be utilized and several are described herein.
As used herein, a cyclopropene refers to any compound with the formula
where each R1, R2, R3 and R4 is independently selected from the group consisting of H and a chemical group of the formula:
-(L)n-Z
where n is an integer from 0 to 12. Each L is a bivalent radical. Suitable L groups include, for example, radicals containing one or more atoms selected from B, C, N, O, P, S, Si, or mixtures thereof. The atoms within an L group may be connected to each other by single bonds, double bonds, triple bonds, or mixtures thereof. Each L group may be linear, branched, cyclic, or a combination thereof. In any one R group (i.e., any one of R1, R2, R3 and R4) the total number of heteroatoms (i.e., atoms that are neither H nor C) is from 0 to 6. Independently, in any one R group the total number of non-hydrogen atoms is 50 or less. Each Z is a monovalent radical. Each Z is independently selected from the group consisting of a C1-C8 alkyl, hydrogen, halo, cyano, nitro, nitroso, azido, chlorate, bromate, iodate, isocyanato, isocyanido, isothiocyanato, pentafluorothio, and a chemical group G, wherein G is a 3- to 14-membered ring system.
The R1, R2, R3, and R4 groups are independently selected from the suitable groups. Among the groups that are suitable for use as one or more of R1, R2, R3, and R4 are, for example, aliphatic groups, aliphatic-oxy groups, alkylphosphonato groups, cycloaliphatic groups, cycloalkylsulfonyl groups, cycloalkylamino groups, heterocyclic groups, aryl groups, heteroaryl groups, halogens, silyl groups, and mixtures and combinations thereof. Groups that are suitable for use as one or more of R1, R2, R3, and R4 may be substituted or unsubstituted.
Among the suitable R1, R2, R3, and R4 groups are, for example, aliphatic groups. Some suitable aliphatic groups include, for example, alkyl, alkenyl, and alkynyl groups. Suitable aliphatic groups may be linear, branched, cyclic, or a combination thereof. Independently, suitable aliphatic groups may be substituted or unsubstituted.
As used herein, a chemical group of interest is said to be “substituted” if one or more hydrogen atoms of the chemical group of interest is replaced by a substituent.
Also among the suitable R1, R2, R3, and R4 groups are, for example, substituted and unsubstituted heterocyclyl groups that are connected to the cyclopropene compound through an intervening oxy group, amino group, carbonyl group, or sulfonyl group; examples of such R1, R2, R3, and R4 groups are heterocyclyloxy, heterocyclylcarbonyl, diheterocyclylamino, and diheterocyclylaminosulfonyl.
Also among the suitable R1, R2, R3, and R4 groups are, for example, substituted and unsubstituted heterocyclic groups that are connected to the cyclopropene compound through an intervening oxy group, amino group, carbonyl group, sulfonyl group, thioalkyl group, or aminosulfonyl group; examples of such R1, R2, R3, and R4 groups are diheteroarylamino, heteroarylthioalkyl, and diheteroarylaminosulfonyl.
Also among the suitable R1, R2, R3, and R4 groups are, for example, hydrogen, fluoro, chloro, bromo, iodo, cyano, nitro, nitroso, azido, chlorate, bromate, iodate, isocyanato, isocyanido, isothiocyanato, pentafluorothio, acetoxy, carboethoxy, cyanato, nitrato, nitrito, perchlorato, allenyl, butylmercapto, diethylphosphonato, dimethylphenylsilyl, isoquinolyl, mercapto, naphthyl, phenoxy, phenyl, piperidino, pyridyl, quinolyl, triethylsilyl, trimethylsilyl, and substituted analogs thereof.
As used herein, the chemical group G is a 3- to 14-membered ring system. Ring systems suitable as chemical group G may be substituted or unsubstituted; they may be aromatic (including, for example, phenyl and naphthyl) or aliphatic (including unsaturated aliphatic, partially saturated aliphatic, or saturated aliphatic); and they may be carbocyclic or heterocyclic. Among heterocyclic G groups, some suitable heteroatoms are, for example, nitrogen, sulfur, oxygen, and combinations thereof. Ring systems suitable as chemical group G may be monocyclic, bicyclic, tricyclic, polycyclic, spiro, or fused; among suitable chemical group G ring systems that are bicyclic, tricyclic, or fused, the various rings in a single chemical group G may be all the same type or may be of two or more types (for example, an aromatic ring may be fused with an aliphatic ring).
In one embodiment, one or more of R1, R2, R3, and R4 is hydrogen or C1-C10 alkyl. In another embodiment, each of R1, R2, R3, and R4 is hydrogen or a C1-C8 alkyl. In another embodiment, each of R1, R2, R3, and R4 is hydrogen or C1-C4 alkyl. In another embodiment, each of R1, R2, R3, and R4 is hydrogen or methyl. In another embodiment, R1 is C1-C4 alkyl and each of R2, R3, and R4 is hydrogen. In another embodiment, R1 is methyl and each of R2, R3, and R4 is hydrogen, and the cyclopropene compound is known herein as 1-methylcyclopropene or “1-MCP.”
In various embodiments, 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. In one embodiment, R is C1-C8 alkyl. In another embodiment, R is methyl.
In another embodiment, the cyclopropene is of the formula:
wherein R1 is a substituted or unsubstituted C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, cycloalkylalkyl, phenyl, or naphthyl group; and R2, R3, and R4 are hydrogen. In another embodiment, the cyclopropene comprises 1-methylcyclopropene (1-MCP).
In one embodiment, the cyclopropene comprises 1-methylcyclopropene (1-MCP). The cyclopropenes applicable to this invention may be prepared by any method. Some suitable methods of preparation of cyclopropenes are the processes disclosed in U.S. Pat. Nos. 5,518,988 and 6,017,849, herein incorporated by reference in their entirety.
In another aspect of the present disclosure, a method of treating plant or plant parts in an environment comprising exogenous ethylene is provided. The method comprises administering a composition comprising a cyclopropene to the produce. The previously described embodiments of the method of treating a mixed type of produce are applicable to the method of treating plant or plant parts in an environment comprising exogenous ethylene described herein.
Treatment of a mixed type of produce with and within a cyclopropene can be evaluated. For the instant example, 1-MCP can be utilized as the exemplary cyclopropene. Any of the described delivery methods can be utilized according to the instant example. Likewise, any of the described produce can comprise the mixed type of produce for the instant example.
Four groups can be utilized for the instant example, with each group including Subset A that is treated with 1-MCP and Subset B that is not treated with 1-MCP. For groups 1, 2, and 3, a single type of produce can be tested in each group. As an exemplary example, Group 1 can include apples alone, Group 2 can include pears alone, and Group 3 can include blueberries alone. Then, Group 4 can include a mixed type of the three types of produce together (e.g., apples, pears, and blueberries).
The four groups can be described as follows:
Treatment of a produce in the presence of exogenous ethylene with and within a cyclopropene can be evaluated. For the instant example, 1-MCP can be utilized as the exemplary cyclopropene. Any of the described delivery methods can be utilized according to the instant example. Likewise, any of the described produce can comprise the mixed type of produce for the instant example.
Four groups can be utilized for the instant example:
Different types of produce have varying ethylene properties. For instance, different types of produce can produce endogenous ethylene at various rates. Furthermore, different types of produce have varying sensitivity to exogenous ethylene, thus influencing the degree of ripening (e.g., freshness) of the produce when it is exposed to ethylene.
The following table lists various types of produce and their associated i) production of endogenous ethylene, ii) sensitivity to exogenous ethylene, and iii) responsiveness to 1-MCP. For production of endogenous ethylene, each type of produce is identified as very low production (“VL”), low production (“L”), medium production (“M”), high production (“H”), and very high production (“VH”), if such values are known. For sensitivity to exogenous ethylene, each type of produce is identified as low sensitivity (“L”), medium sensitivity (“M”), or high sensitivity (“H”), if such values are known. For responsiveness to 1-MCP, each type of produce is identified as low sensitivity (“L”), medium sensitivity (“M”), or high sensitivity (“H”), if such values are known.
Different types of produce have varying ethylene properties. For instance, different types of produce can produce endogenous ethylene at various rates. Furthermore, different types of produce have varying sensitivity to exogenous ethylene, thus influencing the degree of ripening (e.g., freshness) of the produce when it is exposed to ethylene.
The following table lists various types of produce or plant/plant part and their associated i) production of endogenous ethylene and ii) sensitivity to exogenous ethylene. For production of endogenous ethylene, each type of produce is identified as very low production (“VL”), low production (“L”), medium production (“M”), high production (“H”), and very high production (“VH”), if such values are known. For sensitivity to exogenous ethylene, each type of produce is identified as low sensitivity (“L”), medium sensitivity (“M”), or high sensitivity (“H”), if such values are known.
For Examples 6-24, several composition comprising cyclopropene were evaluated for effectiveness on various types of produce or plant/plant parts. For instance, the following exemplary compositions were evaluated:
Bananas were placed in a gas tight 35.4 L plastic chamber with 1 unit of 1-MCP Formulation D supplying 0.0875 mg 1-MCP. The control bananas were placed in a gas tight 35.4 L plastic chamber with a small amount of water in a container. The test was conducted at room temperature. The doors were set ajar the next day.
Tomato variety one was placed in a gas tight 6 L plastic chamber with 1 unit of 1-MCP Formulation D supplying 0.0875 mg 1-MCP. The control tomato was placed in a gas tight 6 L plastic chamber with a small amount of water in a container. The test was conducted at 5° C. The chamber was left closed until evaluation on day 10.
Tomato variety two was placed in a gas tight 6 L plastic chamber with 1 unit of 1-MCP Formulation D supplying 0.0875 mg 1-MCP. The control tomato was placed in a gas tight 6 L plastic chamber with a small amount of water in a container. The test was conducted at 5° C. The chamber was left closed until evaluation on day 10.
Avocados were placed in a gas tight 6 L plastic chamber with 1 unit of 1-MCP Formulation A supplying 2.65 mg 1-MCP. The control avocados were placed in a gas tight 6 L plastic chamber. Each chamber received 1 ml of water in a container. The test was conducted at room temperature. The doors were set ajar the next day.
Bananas were placed in a gas tight 35.4 L plastic chamber with 1 unit of 1-MCP Formulation A supplying 2.65 mg 1-MCP. The control bananas were placed in a gas tight 35.4 L plastic chamber. Each chamber received 1 ml of water in a container. The test was conducted at room temperature. The doors were set ajar the next day.
Green bell peppers and papayas were placed in a gas tight 35.4 L plastic chamber with 1 unit of 1-MCP Formulation A supplying 2.65 mg 1-MCP. The control green bell peppers and papayas were placed in a gas tight 35.4 L plastic chamber. Each chamber received 1 ml of water in a container. The test was conducted at room temperature. The doors were opened at evaluation on day 8.
Bananas and avocados were placed in a gas tight 35.4 L plastic chamber with 2 units of 1-MCP Formulation D supplying 0.175 mg 1-MCP. The control bananas and avocados were placed in a gas tight 35.4 L plastic chamber with a small amount of water in a container. The test was conducted at room temperature. The doors were opened the next day.
Bananas were placed in a gas tight 6 L plastic chamber with 1 unit of 1-MCP Formulation A supplying 2.65 mg 1-MCP. 25% of the surface area of the top 5 sides was left open at the top of the chamber. The control bananas were placed in a gas tight 6 L plastic chamber. Each chamber received 1 ml of water in a container. The test was conducted at room temperature. The chambers were opened the next day.
Bananas were placed in a gas tight 35.4 L plastic chamber with 1 unit of 1-MCP Formulation B divided in fourths supplying 0.026 mg 1-MCP to each banana. The control bananas were placed in a gas tight 35.4 L plastic chamber. Each chamber received 1 ml of water in a container. The test was conducted at room temperature. The chambers were opened the next day.
Bananas were placed in a gas tight 6 L plastic chamber with a 90-minute half-life with 1 unit of 1-MCP Formulation A supplying 2.65 mg 1-MCP. The control bananas were placed in a gas tight 6 L plastic chamber. Each chamber received 1 ml of water in a container. The test was conducted at room temperature. The chambers were opened the next day.
Bananas were placed in a gas tight 6 L plastic chamber with 1.97 g of 1-MCP Formulation C directly onto the bananas supplying 0.590 mg 1-MCP. The control bananas were placed in a gas tight 6 L plastic chamber with 1 ml of water in a container. The test was conducted at room temperature. The chambers were opened the next day.
Cut-up pears, strawberries, apples, and mangos were placed in a gas tight 6 L plastic chamber with 2 units of 1-MCP Formulation D supplying 0.175 mg 1-MCP. The control cut up pears, strawberries, apples and mangos were placed in a gas tight 6 L plastic chamber with a small amount of water in a container. The test was conducted at room temperature. The chambers were opened on day 2.
Cut-up lettuce, cauliflower, and broccoli were placed in a gas tight 6 L plastic chamber with 2 units of 1-MCP Formulation D supplying 0.175 mg 1-MCP. The control cut up lettuce, cauliflower and broccoli were placed in a gas tight 6 L plastic chamber with a small amount of water in a container. The test was conducted at room temperature. The chambers were opened on day 4.
Broccoli, blueberries, and kiwi were placed in a gas tight 35.4 L plastic chamber with 2 units of 1-MCP Formulation A supplying 5.30 mg 1-MCP. The control broccoli, blueberries and kiwi were placed in a gas tight 35.4 L plastic chamber. Each chamber received 1 ml of water in a container. The test was conducted at room temperature. The doors were opened the next day.
Sliced apples were placed in a gas tight 6 L plastic chamber with 2 units of 1-MCP Formulation D supplying 0.175 mg 1-MCP. The sliced apples were placed in a gas tight 6 L plastic chamber with a small amount of water in a container. The test was conducted at room temperature.
Sliced apples were placed in a gas tight 6 L plastic chamber with 2 units of 1-MCP Formulation D supplying 0.175 mg 1-MCP. The sliced apples were placed in a gas tight 6 L plastic chamber with a small amount of water in a container. The test was conducted at 5° C.
Bananas were placed in a gas tight 6 L plastic chamber with Formulation E applied onto a liner under the bananas supplying 2.73 mg 1-MCP. The control bananas were placed on a liner in a gas tight 6 L plastic chamber. Each chamber received 1 ml of water onto the liner. The test was conducted at room temperature. The chambers were opened the next day.
Bananas were placed in a gas tight 6 L plastic chamber with Formulation C applied directly onto the chamber floor supplying 1.03 mg 1-MCP. The control bananas were in a gas tight 6 L plastic chamber with 1 ml of water. The test was conducted at room temperature. The chambers were opened the next day.
Bananas were placed in a gas tight 6 L plastic chamber with Formulation C applied onto a liner under the bananas supplying 0.964 mg 1-MCP. The control bananas were placed on a liner in a gas tight 6 L plastic chamber with 1 ml of water applied onto the liner. The test was conducted at room temperature. The chambers were opened the next day.
This application claims the benefit of U.S. Provisional Patent Application No. 63/282,942, filed Nov. 24, 2022, the entire disclosure of which is hereby incorporated by reference.
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/US2022/050667 | 11/22/2022 | WO |
| Number | Date | Country | |
|---|---|---|---|
| 63282942 | Nov 2021 | US |
