Stable 1-methylcyclopropene compositions and uses thereof

Abstract

Provided are stable compositions comprising 1-methylcyclopropene and a low volatile stabilizer, as well as methods of using the compositions. Methods of delaying maturation of plants, such as fruits, vegetables and flowers, using the compositions are also provided.

Description

[0001] Cross - reference to related applications

[0002] This application claims the priority of U.S. Provisional Application No. 62 / 969,260, filed on February 3, 2020, the content of which is incorporated herein by reference in its entirety. Technical field

[0003] The present invention relates to compositions comprising 1 - methylcyclopropene and low - volatility compounds such as cis - 2 - butene, and to the use of such compositions in delaying the ripening of plants such as fruits, vegetables, and flowers. Background art

[0004] Ethylene affects a wide range of physiological processes in plants, including fruits, vegetables, flowers, ornamental plants, herbs, seeds, nuts, fungi, and grains, such as drooping, senescence and ripening, chlorophyll loss, softening, physiological disorders, germination, coumarin synthesis, lignification, discoloration (browning), decomposition, and stimulation of the defense system. When growing and storing plants and plant products, it is necessary to control the effects of ethylene to extend the shelf - life of these products, delay their ripening period, and slow down browning and senescence.

[0005] One of the methods used is to inhibit the action of ethylene by blocking ethylene receptors in plant cells. 1 - methylcyclopropene (1 - MCP) is a gas that has been used to block ethylene receptors in plant cells. Liquid or gaseous 1 - MCP decomposes rapidly at room temperature through a free - radical process to form dimers, oligomers, degradation products, and / or oxidation products, and thus cannot be stored in pure form for a long time. Therefore, 1 - MCP is usually complexed with host compounds such as cyclodextrins, cucurbit[6]urils, and metal - organic frameworks for storage and use. When used as a complex with cyclodextrin, it is necessary to expose the complex to water (e.g., in the form of humidity) in order to release 1 - MCP from the cyclodextrin. Summary of the invention

[0007] In a first aspect, the composition disclosed herein comprises:

[0008] 1 - methylcyclopropene, and

[0009] a stabilizer;

[0010] wherein the concentration of 1 - methylcyclopropene remains substantially unchanged after at least 4 hours.

[0011] Provided that 1 - methylcyclopropene is not complexed with other molecules.

[0012] In some embodiments, the stabilizer is selected from the group consisting of lower alkanes, lower alkenes, lower dialkyl ethers, lower trialkylamines, and combinations thereof.

[0013] In some embodiments, the stabilizer comprises cis-2-butene.

[0014] In some embodiments, the composition comprises from about 0.1 wt % to about 50 wt % 1-methylcyclopropene.

[0015] In some embodiments, the composition comprises from about 0.1 wt % to about 10 wt % of a stabilizer.

[0016] In some embodiments, the composition is a liquid.

[0017] In some embodiments, the concentration of 1-methylcyclopropene remains substantially unchanged after at least 4 weeks.

[0018] In some embodiments, the composition further comprises:

[0019] Solvents; and

[0020] At least one component selected from the group consisting of a polymer, a plasticizer, a surfactant and an adjuvant.

[0021] In some embodiments, the composition is a gas and further comprises nitrogen, oxygen, and carbon dioxide.

[0022] In some embodiments (when the composition is a gas and further comprises nitrogen, oxygen, and carbon dioxide), the composition comprises from about 1 wt % to about 10 wt % 1-methylcyclopropene.

[0023] In some embodiments (when the composition is a gas and further comprises nitrogen, oxygen, and carbon dioxide), the composition comprises from about 1% to about 10% by volume of 1-methylcyclopropene.

[0024] In some embodiments (when the composition is a gas and further comprises nitrogen, oxygen, and carbon dioxide), the composition comprises about 80 wt % to about 94 wt % nitrogen; about 3 wt % to about 10 wt % oxygen; and about 3 wt % to about 10 wt % carbon dioxide.

[0025] In some embodiments (when the composition is a gas and further comprises nitrogen, oxygen, and carbon dioxide), the composition comprises about 80 vol% to about 94 vol% nitrogen; about 3 vol% to about 10 vol% oxygen; and about 3 vol% to about 10 vol% carbon dioxide.

[0026] In some embodiments (when the composition is a gas and further comprises nitrogen, oxygen, and carbon dioxide), the composition comprises from about 0.1 wt % to about 10 wt % of a stabilizer.

[0027] In some embodiments (when the composition is a gas and further contains nitrogen, oxygen, and carbon dioxide), the composition contains from about 0.1% to about 10% by volume of a stabilizer.

[0028] In a second aspect, an aerosol dispensing container containing the composition of the first aspect is disclosed herein, wherein the composition is at a pressure greater than 1 atm.

[0029] In some embodiments of the aerosol dispensing container, the composition further contains a propellant.

[0030] In some embodiments of the aerosol dispensing container, the composition further contains:

[0031] a solvent; and

[0032] at least one component selected from the group consisting of polymers, plasticizers, surfactants, and adjuvants.

[0033] In some embodiments of the aerosol dispensing container, the composition is stored at a pressure of about 2 atm to about 10 atm. In some embodiments of the aerosol dispensing container, the composition is stored at a pressure of about 10 atm to about 100 atm.

[0034] In some embodiments of the aerosol dispensing container, the interior of the container is substantially free of transition metals.

[0035] In a third aspect, a method of maintaining the freshness of a plant is disclosed herein, comprising contacting the plant with the composition of the first aspect.

[0036] In some embodiments, the plant is a fruit or vegetable. In some embodiments, the plant is a flower.

[0037] In some embodiments, the contacting comprises spraying the composition of the first aspect onto the plant.

[0038] In a fourth aspect, a method of packaging a plant is disclosed herein, comprising:

[0039] placing the plant in a chamber;

[0040] adding the composition of the first aspect (when the composition further contains nitrogen, oxygen, and carbon dioxide) to the interior of the chamber; and

[0041] packaging the plant in the chamber.

[0042] In some embodiments, the plant is a fruit or vegetable. In some embodiments, the plant is a flower.

[0043] A stabilizer can be understood to inhibit the free radical oligomerization reaction (such as dimerization) and oxidation that often occur in 1-MCP, thereby preventing the decomposition of 1-MCP. In addition, in a stabilized 1-MCP composition further containing oxygen, the reaction of oxygen with the stabilizer is faster than the reaction with 1-methylcyclobutene. Therefore, the compositions described herein provide an alternative method for storing and using 1-MCP, which does not require complexing with the main compound, thereby avoiding the costs associated with complexing and additional handling. In addition, when cis-2-butene or isobutene is used as a stabilizer, the composition is more effective in maintaining plant freshness than using 1-MCP or cis-2-butene alone (i.e., a synergistic effect between 1-MCP and cis-2-butene is observed).

[0044] For the sake of clarity, it should be understood that "the concentration of 1-methylcyclopropene remains substantially unchanged after at least 4 hours" means that the concentration of 1-methylcyclopropene changes little (e.g., less than 10%, less than 9%, less than 8%, less than 7%, less than 6%, less than 5%, less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, less than 0.2%, less than 0.1%, less than 0.05%, less than 0.02% or less than 0.01% change) after at least 4 hours from the initial measurement, where the initial measurement is carried out within 1 hour after the composition is formed. The concentration of 1-methylcyclopropene (e.g., the molar concentration of the initial measurement of 1-methylcyclopropene and the molar concentration of the measurement carried out at least one day after the initial measurement) is measured by gas chromatography (GC), using cis-2-butene as an internal standard. In addition, (i) the amount of the internal standard contained in the sample for each measurement is the same, and (ii) the volume of the sample injected into the gas chromatograph for each measurement is the same.

[0045] The term "lower alkane" as used herein refers to alkanes containing 1 to 4 carbon atoms. Lower alkanes include, for example, methane, ethane, propane, butane (e.g., n-butane or isobutane), cyclopropane, and cyclobutane.

[0046] The term "lower olefin" as used herein refers to olefins containing 3 to 4 carbon atoms. Lower olefins include, for example, propene and butenes (e.g., 1-butene, 2-butene (e.g., cis-2-butene and trans-2-butene), and isobutene). The olefin may optionally be substituted with one or more halogens (such as one or more fluorines). Optionally, substituted lower olefins include, for example, 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene.

[0047] The term "lower dialkyl ether" as used herein refers to dialkyl ethers containing 2 to 4 carbon atoms. Lower dialkyl ethers include, for example, dimethyl ether, methyl ethyl ether, diethyl ether, methyl isopropyl ether, and methyl n-propyl ether.

[0048] The term "lower trialkylamine" as used herein refers to a trialkylamine comprising 3 to 6 carbon atoms. The lower trialkylamine includes, for example, trimethylamine, dimethylethylamine, methyldiethylamine and triethylamine.

[0049] The accompanying drawings and the following description further illustrate one or more embodiments of the present invention in detail. Other features, objectives and advantages of the present invention can be clearly seen from the description, drawings and claims. BRIEF DESCRIPTION OF THE DRAWINGS

[0050] Figure 1 is a graph of the percentage of dimer as a function of time as measured by GC in a composition comprising 10 wt % 1-MCP, 5 wt % cis-2-butene (relative to 1-MCP), propane, and butane.

[0051] Figure 2 is a graph of the dimer percentage as a function of time as measured by GC in a composition comprising 10 wt % 1-MCP, 7 wt % cis-2-butene (relative to 1-MCP), and 83 wt % propane and butane.

[0052] Figure 3 is a graph of the dimer percentage as a function of time as measured by GC in a composition including 10 wt % 1-MCP, 3 wt % cis-2-butene (relative to 1-MCP), and isobutane.

[0053] Figure 4 is a graph of the dimer percentage as a function of time as measured by GC in a composition including 5 wt % 1-MCP, 3 wt % cis-2-butene (relative to 1-MCP), and isobutane.

[0054] Figure 5 is a graph showing changes in the peak area ratio of 1-MCP:cis-2-butene over time in a composition including 0.1% by volume 1-MCP, 0.1% by volume cis-2-butene, and carbon dioxide.

[0055] Figure 6 is a graph showing changes in the peak area ratio of 1-MCP:cis-2-butene over time over 59 days in a composition including 0.1% v / v 1-MCP, 0.1% v / v cis-2-butene, and nitrogen.

[0056] Figure 7 is a graph showing changes in the peak area ratio of 1-MCP:cis-2-butene over time over 182 days in a composition including 0.1% v / v 1-MCP, 0.1% v / v cis-2-butene, and nitrogen.

[0057] Figure 8 is a graph showing the change in the peak area ratio of 1-MCP:cis-2-butene over time in a composition including 5% v / v 1-MCP, 5% v / v cis-2-butene, and nitrogen.

[0058] Fig. 9 is a graph showing changes in the peak area ratio of 1-MCP:cis-2-butene over time in a composition including 10% v / v 1-MCP, 10% v / v cis-2-butene, and nitrogen.

[0059] Fig. 10A Contains (1) a graph of the percentage of dimers measured by GC as a function of hours in a composition comprising 10 wt % 1-MCP, 1 wt % cis-2-butene (relative to 1-MCP), and nitrogen. (2) a graph of the percentage of dimers measured by GC as a function of hours in a composition comprising 10 wt % 1-MCP, 10 wt % cis-2-butene (relative to 1-MCP), and nitrogen; and (3) a graph of the percentage of dimers measured by GC as a function of hours in a composition comprising 10 wt % 1-MCP, 50 wt % cis-2-butene (relative to 1-MCP), and nitrogen.

[0060] Fig. 10B The present invention covers (1) a curve of the percentage of dimers measured by GC over days in a composition comprising 10 wt% 1-MCP, 1 wt% cis-2-butene (relative to 1-MCP) and nitrogen. (2) a curve of the percentage of dimers measured by GC over time in a composition comprising 10 wt% 1-MCP, 10 wt% cis-2-butene (relative to 1-MCP) and nitrogen; and (3) a curve of the percentage of dimers measured by GC over time in a composition comprising 10 wt% 1-MCP, 50 wt% cis-2-butene (relative to 1-MCP) and nitrogen.

[0061] Fig.11 Covered are (1) a graph of the dimer percentage measured by GC as a function of time in a composition comprising 1-MCP and butane in a 1:1 volume ratio, and (2) a graph of the dimer percentage measured by GC as a function of time in 1-MCP.

[0062] Like reference numbers in the drawings represent like elements. DETAILED DESCRIPTION

[0063] Described herein are compositions comprising 1-methylcyclopropene (1-MCP) and a stabilizer for maintaining the freshness of plants.

[0064] Composition

[0065] In one aspect, the compositions disclosed herein comprise:

[0066] 1-Methylcyclopropene, and

[0067] Stabilizer.

[0068] In another aspect, the composition disclosed herein comprises:

[0069] 1-Methylcyclopropene, and

[0070] Stabilizers;

[0071] Among them, the concentration of 1-methylcyclopropene remained essentially unchanged after at least 4 hours;

[0072] In another aspect, the composition disclosed herein comprises:

[0073] 1-Methylcyclopropene; and

[0074] Stabilizers;

[0075] Among them, the concentration of 1-methylcyclopropene remained basically unchanged after at least 4 hours.

[0076] The prerequisite is that 1-methylcyclopropene does not complex with other molecules.

[0077] In some embodiments, the stabilizer has low volatility. For example, the stabilizer has a vapor pressure of about 1700 to about 9000Torr (for example, about 1750Torr to about 8750Torr, about 1750Torr to about 1950Torr, about 3200Torr to about 3600Torr, about 8400Torr to about 8800Torr, about 1875Torr, about 3430Torr, or about 8700Torr) at about 50°C normal pressure. In some embodiments, the stabilizer is selected from the group consisting of lower alkanes, lower olefins, lower dialkyl ethers, lower trialkylamines, and combinations thereof. In some embodiments, the stabilizer is a lower alkane. Lower alkanes include, for example, methane, ethane, propane, butane (for example, n-butane or isobutane), cyclopropane, and cyclobutane. In some embodiments, the stabilizer is a lower olefin. Lower olefins include, for example, propylene and butene (e.g., 1-butene, 2-butene (e.g., cis-2-butene and trans-2-butene) and isobutylene), 1,3,3,3-tetrafluoropropylene and 2,3,3,3-tetrafluoropropylene. In some embodiments, the stabilizer is a dialkyl ether. Lower dialkyl ethers include, for example, dimethyl ether, methyl ethyl ether, diethyl ether, methyl isopropyl ether and methyl n-propyl ether. In some embodiments, the stabilizer is a lower trialkylamine. Lower trialkylamines include, for example, trimethylamine, dimethylethylamine, methyldiethylamine and triethylamine. In some embodiments, the stabilizer comprises cis-2-butene. For example, the stabilizer is cis-2-butene.

[0078] In some embodiments, the composition comprises about 0.01% to about 50% by weight of 1-methylcyclopropene. For example, by weight, the composition comprises about 0.01% to about 0.1%, from about 0.1% to about 1%, from about 1% to about 3%, from about 3% to about 5%, from about 5% to about 10%, from about 10% to about 20%, from about 20% to about 30%, from about 30% to about 40%, from about 40% to about 50%, from about 0.01% to about 5%, about 0.01% to about 10%, about 0.01% to about 25%, about 0.01% to about 40%, about 0.1% to about 50%, about 5% to about 50%, about 10% to about 50%, about 30% to about 50%, about 5% to about 40%, or about 10% to about 30% of 1-methylcyclopropene. For example, the composition comprises about 0.01%, about 0.1%, about 1%, about 3%, about 5%, about 7.5%, about 10%, about 12.5%, about 15%, about 17.5%, about 20%, about 22.5%, about 25%, about 27.5%, about 30%, about 32.5%, about 35%, about 37.5%, about 40%, about 42.5%, about 45%, about 47.5%, or about 50% 1-methylcyclopropene by weight.

[0079] In some embodiments, the composition comprises about 0.1% to about 50% by weight of a stabilizer. For example, by weight, the composition comprises about 0.01% to about 1%, about 0.1% to about 0.8%, about 0.1% to about 1%, about 1% to about 2%, about 2% to about 3%, about 3% to about 4%, about 4% to about 5%, about 5% to about 6%, about 6% to about 7%, about 7% to about 8%, about 8% to about 9%, about 9% to about 10%, about 0.1% to about 5%, about 0.1% to about 10%, about 0.1% to about 20%, about 0.1% to about 30%, about 0.1% to about 40%, about 0.1% to about 50%, about 10% to about 50%, about 20% to about 50%, about 30% to about 50%, about 40% to about 50% of a stabilizer. For example, by weight, the composition comprises about 0.1%, about 0.15%, about 0.3%, about 0.5%, about 0.7%, about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9% or about 10% stabilizer. For example, the composition comprises about 1% by weight stabilizer.

[0080] In some embodiments, the composition is a liquid.

[0081] In some embodiments, the concentration of 1-methylcyclopropene is substantially unchanged after at least 4 hours. For example, the concentration of 1-methylcyclopropene is substantially unchanged after at least 4 hours, at least 8 hours, at least 12 hours, at least 16 hours, at least 20 hours, at least 24 hours, at least 28 hours, at least 32 hours, at least 36 hours, at least 40 hours, at least 44 hours, at least 48 hours, at least 2.5 days, at least 3 days, at least 3.5 days, at least 4 days, at least 5 days, at least 6 days, at least 7 days, at least 8 days, at least 9 days, at least 10 days, at least 20 days, at least 4 weeks, at least 2 months, at least 3 months, at least 4 months, at least 5 months, at least 6 months, at least 7 months, at least 8 months, at least 9 months, at least 10 months, at least 11 months, at least 1 year, at least 1.5 years, at least 2 years, at least 3 years, at least 4 years, at least 5 years, or at least 10 years.

[0082] In some embodiments, the composition does not substantially contain water. In some of these embodiments, the composition comprises less than 5% by weight of water. For example, by weight, the composition comprises less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5% or less than 0.1% water. In some embodiments, the composition does not contain water. In some embodiments (when the composition is in the form of a gas), the humidity of the gas is less than 100%. For example, the humidity of the gas is less than 90%, less than 80%, less than 50%, less than 30%, less than 20%, less than 10%, less than 5%, less than 2%, or less than 1%.

[0083] In some embodiments, the composition further comprises a solvent.

[0084] In some embodiments, the composition comprises about 1% to about 99% by weight of a solvent. For example, by weight, the composition comprises about 40% to about 99%, about 50% to about 99%, about 60% to about 99%, about 70% to about 99%, about 75% to about 99%, about 80% to about 99%, about 85% to about 99%, about 90% to about 99%, about 90% to about 96%, about 93% to about 96%, about 80% to about 96%, about 84% to about 92%, about 83% to about 89%, about 83%, about 85%, about 87%, about 89%, about 92%, or about 95% of a solvent.

[0085] In some embodiments, the composition further comprises a propellant. Propellants include but are not limited to argon, methane, ethane, propane, butane (such as n-butane or isobutane), propylene, 1-butene, cis-2-butene, trans-2-butene, nitrous oxide, nitrogen, carbon dioxide, dimethyl ether, methyl ethyl ether, 1,3,3,3-tetrafluoropropylene, 2,3,3,3-tetrafluoropropylene, chlorofluorocarbons (for example, trichloromonofluoromethane, dichlorodifluoromethane, dichlorotetrafluoroethane, chlorodifluoromethane, trifluoromonofluoroethane, chlorodifluoroethane, difluoroethane and heptafluoropropane), air and combinations thereof. In some embodiments, the composition comprises propane and butane.

[0086] In some embodiments, the composition comprises about 1% to about 99% by weight of a propellant. For example, by weight, the composition comprises about 40% to about 99%, about 50% to about 99%, about 60% to about 99%, about 70% to about 99%, about 75% to about 99%, about 80% to about 99%, about 85% to about 99%. About 90% to about 99%, about 90% to about 96%, about 93% to about 96%, about 80% to about 96%, about 84% to about 92%, about 83% to about 89%, about 83%, about 85%, about 87%, about 89%, about 92%, or about 95% of a propellant.

[0087] In some embodiments, the composition comprises from about 4 wt % to about 13 wt % of 1-methylcyclopropene, from about 0.1 wt % to about 1 wt % of a stabilizer, and from about 81 wt % to about 96 wt % of a propellant.

[0088] In some embodiments, the composition comprises from about 8 wt % to about 11 wt % of 1-methylcyclopropene, from about 0.1 wt % to about 1 wt % of a stabilizer, and from about 81 wt % to about 96 wt % of a propellant.

[0089] In some embodiments, the composition comprises from about 4 wt % to about 13 wt % of 1-methylcyclopropene, from about 2 wt % to about 8 wt % of a stabilizer, and from about 81 wt % to about 96 wt % of a propellant.

[0090] In some embodiments, the composition comprises from about 8 wt % to about 11 wt % of 1-methylcyclopropene, from about 2 wt % to about 8 wt % of a stabilizer, and from about 81 wt % to about 96 wt % of a propellant.

[0091] In some embodiments, the composition comprises from about 4 wt % to about 13 wt % of 1-methylcyclopropene, from about 0.1 wt % to about 1 wt % of a stabilizer, and from about 81 wt % to about 96 wt % of a propellant.

[0092] In some embodiments, the composition comprises from about 8 wt % to about 11 wt % of 1-methylcyclopropene, from about 0.1 wt % to about 1 wt % of a stabilizer, and from about 81 wt % to about 96 wt % of a propellant.

[0093] In some embodiments, the composition comprises from about 4 wt % to about 13 wt % of 1-methylcyclopropene, from about 2 wt % to about 8 wt % of a stabilizer, and from about 81 wt % to about 96 wt % of a propellant.

[0094] In some embodiments, the composition comprises from about 8 wt % to about 11 wt % of 1-methylcyclopropene, from about 2 wt % to about 8 wt % of a stabilizer, and from about 81 wt % to about 96 wt % of a propellant.

[0095] In some embodiments, the composition further comprises at least one component selected from the group consisting of a polymer, a plasticizer, a surfactant, and an adjuvant. It should be understood that the polymer, plasticizer, surfactant, and / or adjuvant enable the composition to adhere to the plant surface and, in certain embodiments, release 1-MCP over time.

[0096] In some embodiments, the composition further comprises:

[0097] Solvents; and

[0098] At least one component selected from the group consisting of a polymer, a plasticizer, a surfactant and an adjuvant.

[0099] Solvents include, but are not limited to, acetone, acetonitrile, dichloromethane, methanol, ethanol, isopropanol, chloroform, diethyl ether, methyl tert-butyl ether, methyl ethyl ketone, glycerol, carbon tetrachloride, cyclohexane, toluene, anisole, pyridine, acetic acid, hexane, lignin, dimethyl sulfoxide, N,N-dimethylacetamide, N,N-dimethylformamide, tetrahydrofuran, and petroleum ether.

[0100] The polymer includes, but is not limited to, shellac, polyvinyl pyrrolidone, polyvinyl pyrrolidone-vinyl acetate copolymer, vinyl acetate-crotonic acid, methylvinyl-ethyl maleate copolymer, butyl maleate, tert-butylacrylamide-ethyl acrylate-acrylic acid copolymer, acrylate-acrylamide copolymer, vinyl caprolactam-vinyl pyrrolidone-dimethylaminoethyl methacrylate copolymer, and any combination thereof.

[0101] Plasticizers include, but are not limited to, aminomethyl propanol, aminomethyl propanediol, triisopropylamine, dimethyl octadecylamine, triethanolamine, di(2-ethylhexyl) phthalate (DEHP), di(2-propylheptyl) phthalate (DPHP), diisononyl phthalate (DINP), di-n-butyl phthalate (DnBP or DBP), butyl benzyl phthalate (BBzP), diisodecyl phthalate (DIDP), dioctyl phthalate (DOP or DnOP), diisooctyl phthalate (DIOP), diethyl phthalate (DEP), diisobutyl phthalate (DIBP), di-n-hexyl phthalate, trimethyl trimellitate (TMTM), tri(2-ethyl) trimellitate (TMTM), tri(2-ethyl) trimellitate (DTP), diisobutyl phthalate (DIBP ... trimellitic acid ester (TEHTM) (TOTM), tri (n-octyl, n-decyl) trimellitic acid ester (ATM), tri (heptyl, nonyl) trimellitic acid ester (LTM), n-octyl trimellitic acid ester (OTM), di (2-ethylhexyl) adipate (DEHA), dimethyl adipate (DMAD), monomethyl adipate (MMAD), dioctyl adipate (DOA), dibutyl sebacate (DBS), dibutyl maleate (DBM), diisobutyl maleate (DIBM), azelaic acid esters, benzoic acid esters, terephthalic acid esters (e.g., dioctyl terephthalate / DEHT), diisononyl 1,2-cyclohexanedicarboxylate, phenyl alkyl sulfonates (ASE), sulfonamides (e.g., N-ethyl toluenesulfonamide (o / p ETSA), N-(2-hydroxypropyl)benzenesulfonamide (HP BSA), or N-(n-butyl)benzenesulfonamide (BBSA-NBBS)), organic phosphates (e.g., tricresyl phosphate (TCP) or tributyl phosphate (TBP)), glycols and polyethers (e.g., triethylene glycol dihexanoate (3G6 or 3GH) and tetraethylene glycol diheptanoate (4G7)), polymeric plasticizers, polybutene, acetylated monoglycerides, alkyl citrates (e.g., triethyl citrate (TEC), acetylated triethyl citrate (ATEC), tributyl citrate (TBC), acetylated tributyl citrate (ATBC), trioctyl citrate (TOC), acetyl trioctyl citrate (ATOC), trihexyl citrate (THC), acetyl trihexyl citrate (ATHC), butyryl trihexyl citrate (BTHC or O-butyryl trihexyl citrate) and trimethyl citrate (TMC)), methyl ricinoleate, epoxidized soybean oil (ESBO), epoxidized vegetable oil, nitroglycerin, butane trinitrate (BTTN), dinitrotoluene (DNT), and any combination thereof.

[0102] Surfactants include, but are not limited to, polysorbates (e.g., tweens), sodium dodecyl sulfate (sodium lauryl sulfate), dodecyldimethylamine oxide, cetyltrimethylammonium bromide (CTAB), polyethoxylated alcohols, polyoxyethylene sorbitan, octoxynol, N,N-dimethyldodecylamine-N-oxide, cetyltrimethylammonium bromide (HTAB), polyoxyethylene 10 dodecyl ether, bile salts (e.g., sodium deoxycholate and sodium cholate), polyethylene glycol castor oil, nonylphenol polyoxyethylene ether, cyclodextrin, lecithin, benzethonium chloride, benzalkonium chloride, dimethyl siloxane, and any combination thereof.

[0103] Adjuvants include, but are not limited to, oils (e.g., crop oils (e.g., paraffin oil or petroleum) and vegetable oils), compatibilizers, buffers (e.g., potassium dihydrogen phosphate, sodium dihydrogen phosphate, disodium hydrogen phosphate, potassium dihydrogen phosphate, dipotassium hydrogen phosphate, calcium carbonate), conditioners (e.g., polyquaternium salts), defoamers (e.g., kerosene, fuel oil, vegetable oil, fatty alcohol, polydimethylsiloxane, hydrophobic silica, ethylene bis stearamide, paraffin, ester wax, polyethylene glycol-polypropylene glycol, alkyl polyacrylate, dimethyl silicone oil), anti-precipitation agents (e.g., fumed silica), deposition agents, spray drift inhibitors (e.g., drift control agents). agents (such as polyacrylamide), thickeners (such as alginic acid, agar, carrageenan, locust bean gum, pectin, gelatin, polyurethanes (such as acrylic polymers, latex, styrene, butadiene, etc.), polyvinyl alcohol, clays (such as attapulgite, bentonite, montmorillonite clay, cellulose, sulfonates, guar gum, xanthan gum, cellulose, acacia gum, pullulan, konjac, casein, collagen, albumin, modified castor oil, and silicones (such as silicone resins, dimethyl siloxanes and modified siloxanes), fertilizers (such as nitrogen fertilizers, phosphate fertilizers and potash fertilizers), foam markers, tank cleaners, colorants, suspending agents (such as alginates, methylcellulose, hydroxyethylcellulose, carboxymethylcellulose, sodium carboxymethylcellulose, microcrystalline cellulose, gum arabic, tragacanth, xanthan gum, bentonite, carbomer, carrageenan, powdered cellulose and gelatin), tackifiers (such as rosin, terpenes, modified terpenes, hydrogenated hydrocarbon resins, terpene-phenolic resins and phenolic resins), and any combination thereof.

[0104] In some embodiments, the composition is a gas. In some such embodiments, the composition further comprises nitrogen, oxygen, carbon dioxide, argon, and combinations thereof. For example, the composition comprises nitrogen, oxygen, and / or carbon dioxide. For example, the composition comprises nitrogen. For example, the composition comprises carbon dioxide. For example, the composition comprises oxygen. For example, the composition comprises argon. In some embodiments, the composition is a gas and further comprises nitrogen, oxygen, and carbon dioxide.

[0105] In some embodiments (when the composition is a gas), the composition comprises about 0.1% to about 20% by weight of 1-methylcyclopropene. For example, by weight, the composition comprises about 1% to about 10%, about 1% to about 3%, about 3% to about 6%, or about 6% to about 10% of 1-methylcyclopropene. For example, by weight, the composition comprises about 0.1%, about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, or about 10% of 1-methylcyclopropene.

[0106] In some embodiments (when the composition is a gas), the composition comprises about 0.1% to about 20% by volume of 1-methylcyclopropene. For example, by volume, the composition comprises about 1% to about 10%, about 1% to about 3%, about 3% to about 6%, or about 6% to about 10% of 1-methylcyclopropene. For example, by volume, the composition comprises about 0.1%, about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, or about 10% of 1-methylcyclopropene.

[0107] In some embodiments (when the composition is a gas), the composition comprises about 40% to about 98% by weight of nitrogen. For example, by weight, the composition comprises about 50% to about 96%, about 60% to about 96%, about 70% to about 96%, or about 80% to about 94% nitrogen. For example, the composition comprises about 80% to about 94% by weight of nitrogen. For example, by weight, the composition comprises about 50%, about 60%, about 70%, about 80%, about 82.5%, about 85%, about 87.5%, about 90%, about 92.5%, or about 94% nitrogen.

[0108] In some embodiments (when the composition is a gas), the composition comprises about 40% to about 98% by volume of nitrogen. For example, by volume, the composition comprises about 50% to about 96%, about 60% to about 96%, about 70% to about 96%, or about 80% to about 94% nitrogen. For example, the composition comprises about 80% to about 94% by volume of nitrogen. For example, by volume, the composition comprises about 50%, about 60%, about 70%, about 80%, about 82.5%, about 85%, about 87.5%, about 90%, about 92.5%, or about 94% nitrogen.

[0109] In some embodiments (when the composition is a gas), the composition comprises about 0.1% to about 20% by weight of oxygen. For example, by weight, the composition comprises 1% to about 20%, about 1% to about 15%, about 3% to about 10%, about 3% to about 6%, about 6% to about 10%, or about 5% to about 8% of oxygen. For example, the composition comprises about 3% to about 10% by weight of oxygen. For example, by weight, the composition comprises about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10% of oxygen.

[0110] In some embodiments (when the composition is a gas), the composition comprises about 0.1% to about 20% by volume of oxygen. For example, by volume, the composition comprises 1% to about 20%, about 1% to about 15%, about 3% to about 10%, about 3% to about 6%, about 6% to about 10%, or about 5% to about 8% oxygen. For example, the composition comprises about 3% to about 10% by volume of oxygen. For example, by volume, the composition comprises about 0.1%, about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9% or about 10% oxygen.

[0111] In some embodiments (when the composition is a gas), the composition comprises about 0.1% to about 20% by weight of carbon dioxide. For example, by weight, the composition comprises about 1% to about 20%, about 1% to about 15%, about 3% to about 10%, about 3% to about 6%, about 6% to about 10%, or about 5% to about 8% carbon dioxide. For example, the composition comprises about 3% to about 10% by weight of carbon dioxide. For example, by weight, the composition comprises about 0.1%, about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9% or about 10% carbon dioxide.

[0112] In some embodiments (when the composition is a gas), the composition comprises about 0.1% to about 20% by volume of carbon dioxide. For example, by volume, the composition comprises about 1% to about 20%, about 1% to about 15%, about 3% to about 10%, about 3% to about 6%, about 6% to about 10%, or about 5% to about 8% carbon dioxide. For example, the composition comprises about 3% to about 10% by volume of carbon dioxide. For example, by volume, the composition comprises about 0.1%, about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9% or about 10% carbon dioxide.

[0113] In some embodiments (when the composition is a gas), nitrogen, oxygen, and carbon dioxide are present in the amounts described above individually and in any combination.

[0114] In some embodiments (when the composition is a gas), the composition comprises from about 80% to about 94% by weight nitrogen; from about 3% to about 10% by weight oxygen; and from about 3% to about 10% by weight carbon dioxide.

[0115] In some embodiments (when the composition is a gas), the composition comprises about 80 vol% to about 94 vol% nitrogen; about 3 vol% to about 10 vol% oxygen; and about 3 vol% to about 10 vol% carbon dioxide.

[0116] In some embodiments (when the composition is a gas), the composition comprises about 0.1% to about 50% by weight of a stabilizer. For example, by weight, the composition comprises about 0.1% to about 20%, about 0.1% to about 15%, about 0.1% to about 12%, about 0.1% to about 10%, about 0.1% to about 8%, about 0.1% to about 6%, about 0.1% to about 5%, about 0.1% to about 4%, about 0.1% to about 2%, about 0.1% to about 1%, about 0.5% to about 7%, about 0.5% to about 5%, about 0.5% to about 2%, or about 0.5% to about 1.5% of a stabilizer. For example, by weight, the composition comprises about 0.1% to about 10% by weight of a stabilizer. For example, the composition comprises about 0.1%, about 0.5%, about 1%, about 2%, about 3%, about 4%, about 5%, about 7%, about 8%, about 9% or about 10% of a stabilizer. For example, the composition comprises about 1% by weight of a stabilizer.

[0117] In some embodiments (when the composition is a gas), the composition includes about 0.1% to about 50% by volume of a stabilizer. For example, by volume, the composition includes about 0.1% to about 20%, about 0.1% to about 15%, about 0.1% to about 12%, about 0.1% to about 10%, about 0.1% to about 8%, about 0.1% to about 6%, about 0.1% to about 5%, about 0.1% to about 4%, about 0.1% to about 2%, about 0.1% to about 1%, about 0.5% to about 7%, about 0.5% to about 5%, about 0.5% to about 2%, or about 0.5% to about 1.5% of a stabilizer. For example, by volume, the composition includes about 0.1% to about 10% by volume of a stabilizer. For example, by volume, the composition comprises about 0.1%, about 0.5%, about 1%, about 2%, about 3%, about 4%, about 5%, about 7%, about 8%, about 9% or about 10% stabilizer. For example, the composition comprises about 1% by volume stabilizer.

[0118] In some embodiments (when the composition is a gas), the composition comprises from about 0.1% to about 10% by volume of 1-methylcyclopropene; from about 0.1% to about 10% by volume of a stabilizer; and from about 80% to about 98.8% by volume of a propellant.

[0119] In some embodiments (when the composition is a gas), the concentration of 1-methylcyclopropene is substantially constant after at least 4 hours. For example, the concentration of 1-methylcyclopropene is substantially constant after at least 3.25 hours, at least 4 hours, at least 5 hours, at least 8 hours, at least 12 hours, at least 16 hours, at least 20 hours, at least 23.25 hours, at least 24 hours, at least 28 hours, at least 32 hours, at least 36 hours, at least 40 hours, at least 44 hours, at least 48 hours, at least 95.25 hours, at least 172 hours, at least 197.25 hours, at least 1483.25 hours, at least 2.5 days, at least 3 days, at least 3.5 days, at least 4 days, at least 5 days, at least 6 days, at least 7 days, at least 8 days, at least 9 days, at least 10 days, at least 16 days, at least 17 days, at least 18 days, at least 19 days, at least 20 days, at least 21 days, at least 23 days, at least 24 days, at least 28 hours, at least 32 hours, at least 36 hours, at least 40 hours, at least 44 hours, at least 48 hours, at least 95.25 hours, at least 172 hours, at least 197.25 hours, at least 1483.25 hours, at least 2.5 days, at least 3 days, at least 3.5 days, at least 4 days, at least 5 days, at least 6 days, at least 7 days, at least 8 days, at least 9 days, at least 10 days, at least 16 days, At least 20 days, at least 23 days, at least 24 days, at least 4 weeks, at least 36 days, at least 39 days, at least 43 days, at least 50 days, at least 56 days, at least 57 days, at least 59 days, at least two months, at least 64 days, at least 71 days, at least 105 days, at least 3 months, at least 147 days, at least 182 days, at least 269 days, at least 310 days, at least 557 days, at least 4 months, at least 5 months, at least 6 months, at least 7 months, at least 8 months, at least 9 months, at least 10 months, at least 11 months, at least 1 year, at least 1.5 years, at least 2 years, at least 3 years, at least 4 years, at least 5 years or at least 10 years.

[0120] In some embodiments, the composition comprises an insecticide. In some embodiments, the insecticide comprises an insecticide, a nematicide, a molluscicide, a rodenticide, a bactericide, an anthelmintic, a driving agent, an antimicrobial and / or a fungicide. Non-limiting examples of insecticides include carbofuran, phorate, chlorpyrifos, monocrotophos, carbaryl, fenbutacarb, ethoprolin, endosulfan, dichlorvos, cartap hydrochloride, quinalphos, acephate, carbosulfan, methyl demeton, dimethoate, methyl parathion and triazophos. Non-limiting examples of fungicides include activator, antifungal, benomyl, binacarb, tetrafluconazole, tebuconazole, propioconazole, oxepiconazole, bifenthrin, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, ethiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imipenem, methiconazole, metconazole, myclobutanil, tebuconazole, prothioconazole, silanil, silanil, chlor ... Fluazole, triadimefon, triadimenol, thiamethoxam, imazalil, oxpoconazole, pyraclostrobin, prochloraz, triflumizole, chlorfenapyr, nuarimol, chlorfenapyr, pyrifenox, azoxystrobin, enestrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, etherstrobin, fenoxystrobin, oxadiazine, oxadiazine, oxadiazine, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin. Non-limiting examples of nematicides include aldicarb, halogenated hydrocarbons DBCP, 1,3-dichloropropylene, chloropicrin, methyl bromide, ethylene dibromide, 1,2-dibromo-3-chloropropane, sodium metamethane, dazomethon, methyl isothiocyanate, sodium tetrathiocarbonate, chloranil, chloranil, cadusin, aldicarb, carbofuran, oxamyl or thiathioate. Non-limiting examples of antimicrobials include benzalkonium chloride and triclosan.

[0121] In some embodiments, the composition comprises from about 0.1% to about 30% by weight of the pesticide. For example, the composition comprises from about 0.1% to about 25%, about 0.1% to about 20%, about 0.1% to about 15%, about 0.1% to about 10%, about 0.1% to about 5%, about 0.1% to about 3%, about 0.1% to about 2%, about 0.1% to about 1%, about 0.1% to about 0.5%, about 2% to about 10%, about 5% to about 15%, about 10% to about 20%, about 0.1%, about 0.2%, about 0.4%, about 0.5%, about 0.7%, about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 12.5%, about 15%, about 17.5%, about 20%, about 22.5% or about 25% of the pesticide by weight.

[0122] In some embodiments, the composition comprises from about 0.1% to about 30% by volume of the pesticide. For example, the composition comprises from about 0.1% to about 25%, about 0.1% to about 20%, about 0.1% to about 15%, about 0.1% to about 10%, about 0.1% to about 5%, about 0.1% to about 3%, about 0.1% to about 2%, about 0.1% to about 1%, about 0.1% to about 0.5%, about 2% to about 10%, about 5% to about 15%, about 10% to about 20%, about 0.1%, about 0.2%, about 0.4%, about 0.5%, about 0.7%, about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 12.5%, about 15%, about 17.5%, about 20%, about 22.5% or about 25% of the pesticide by volume.

[0123] In some embodiments, the 1-methylcyclopropene is not compounded with other molecules. For example, 1-methylcyclopropene is not compounded with a host compound or a metal complex. For illustration purposes, the compounding of 1-methylcyclopropene with a host compound refers to that due to the Gibbs free energy of the complex, the free energy of 1-methylcyclopropene and the host compound is lower, and 1-methylcyclopropene is combined with the host compound by intermolecular forces (for example, ionic bonds, hydrogen bonds, halogen bonds, van der Waals forces, hydrophobic interactions and any combination thereof). The non-limiting examples of host compounds include cyclodextrins (α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin), carbohydrates, porphyrins, phosphazenes, macrocyclic polyethers (for example, crown ethers), calixarene and cucurbituril (for example, cucurbituril [6] uril). In some embodiments, these compositions do not include 1-MCP being adsorbed on an adsorbent. Non-limiting examples of compounds or materials that adsorb 1-MCP include carbon (e.g., any carbon allotrope (e.g., carbon black, lamp black carbon, activated carbon, charcoal, anthracite, coal, coke, vitreous carbon, glassy carbon, ash, activated carbon, soot, and bone char)), metal organic frameworks (e.g., basolite C300 and basolite A520), silicate materials (e.g., polysiloxanes, polyalkylsiloxanes, polyalkylenesiloxanes, polyoxyalkylene materials), metal oxides, zeolites (e.g., zeolite Z13X), metal coordination polymer networks, and silica (e.g., silica gel). In some embodiments, the composition does not include a complex of 1-methylcyclopropene with a host compound (e.g., cyclodextrin (e.g., α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin)), a carbohydrate, a porphyrin, a phosphazene, a macrocyclic polyether (e.g., a crown ether), a calixarene, a metal organic framework (e.g., basolite C300 and basolite A520), a cucurbituril (e.g., cucurbit [6] uril) or a complex with a metal complex; and 1-MCP adsorbed onto an adsorbent (including carbon (e.g., any carbon allotrope (e.g., carbon black, lampblack carbon, activated carbon, charcoal, anthracite, coal, coke, vitreous carbon, glassy carbon, ash, reactivated carbon, soot, and bone char))), a metal organic framework (e.g., basolite C300 and basolite A520), a cucurbituril (e.g., cucurbit [6] uril) or a complex with a metal complex. A520), silicate materials (e.g., polysiloxanes, polyalkylsiloxanes, polyalkylenesiloxanes, and polyoxyalkylene materials), metal oxides, zeolites (e.g., zeolite Z13X), metal coordination polymer networks, and silica (e.g., silica gel).

[0124] Products

[0125] In another aspect, an aerosol dispensing container containing any of the compositions described herein is described.

[0126] wherein the composition is a liquid; and

[0127] wherein the composition is under a pressure greater than 1 atm.

[0128] In some embodiments, the composition contained in the aerosol dispensing container also includes a propellant. Propellants include but are not limited to argon, methane, ethane, propane, butane (such as n-butane or isobutane), propylene, 1-butene, cis-2-butene, trans-2-butene, nitrous oxide, nitrogen, carbon dioxide, dimethyl ether, methyl ethyl ether, 1,3,3,3-tetrafluoropropylene, 2,3,3,3-tetrafluoropropylene, chlorofluorocarbons (for example, trichloromonofluoromethane, dichlorodifluoromethane, dichlorotetrafluoroethane, chlorodifluoromethane, trifluoromonofluoroethane, chlorodifluoroethane, difluoroethane and heptafluoropropane), air and combinations thereof. In some embodiments, the propellant includes propane. In some embodiments, the propellant includes butane. In some embodiments, the propellant includes isobutane.

[0129] In some embodiments, the composition comprises from about 1% to about 99% propellant by weight. For example, the composition comprises from about 40% to about 99%, from about 50% to about 99%, from about 60% to about 99%, from about 70% to about 99%, from about 75% to about 99%, from about 80% to about 99%, from about 85% to about 99%. From about 90% to about 99%, from about 90% to about 96%, from about 93% to about 96%, from about 80% to about 96%, from about 84% to about 92%, from about 83% to about 89%, from about 83%, from about 85%, from about 87%, from about 89%, from about 92%, or from about 95% propellant.

[0130] In some embodiments, the composition comprises about 1% to about 99% propellant by volume. For example, the composition comprises about 40% to about 99%, about 50% to about 99%, about 60% to about 99%, about 70% to about 99%, about 75% to about 99%, about 80% to about 99%, about 85% to about 99%. About 90% to about 99%, about 90% to about 96%, about 93% to about 96%, about 80% to about 96%, about 84% to about 92%, about 83% to about 89%, about 83%, about 85%, about 87%, about 89%, about 92%, or about 95% propellant.

[0131] In some embodiments, the concentration of 1-methylcyclopropene is substantially unchanged after at least 4 hours. For example, the concentration of 1-methylcyclopropene is substantially unchanged after at least 4 hours, at least 8 hours, at least 12 hours, at least 16 hours, at least 20 hours, at least 24 hours, at least 28 hours, at least 32 hours, at least 36 hours, at least 40 hours, at least 44 hours, at least 48 hours, at least 2.5 days, at least 3 days, at least 3.5 days, at least 4 days, at least 5 days, at least 6 days, at least 7 days, at least 8 days, at least 9 days, at least 10 days, at least 20 days, at least 4 weeks, at least 2 months, at least 3 months, at least 4 months, at least 5 months, at least 6 months, at least 7 months, at least 8 months, at least 9 months, at least 10 months, at least 11 months, at least 1 year, at least 1.5 years, at least 2 years, at least 3 years, at least 4 years, at least 5 years, or at least 10 years.

[0132] In some embodiments, the composition contained in the aerosol dispensing container is stored at a pressure of about 2 atm to about 200 atm. For example, the composition contained in the aerosol dispensing container is stored at a pressure of about 2 atm to about 160 atm, about 2 atm to about 120 atm, about 2 atm to about 100 atm, about 2 atm to about 90 atm, about 2 atm to about 60 atm, about 2 atm to about 40 atm, about 2 atm to about 20 atm, about 2 atm to about 10 atm, about 10 atm to about 200 atm, about 30 atm to about 200 atm, about 50 atm to about 200 atm, about 70 atm to about 200 atm, about 90 atm to about 200 atm, about 120 atm to about 200 atm, about 150 atm to about 200 atm, about 10 atm to about 160 atm, about 30 atm to about 160 atm, about 60 atm to about 120 atm, about 10 atm to about 100 atm, or about 30 atm to about 90 atm. For example, the composition contained in the aerosol dispensing container is stored at a pressure of about 2 atm, about 3.5 atm, about 10 atm, about 20 atm, about 30 atm, about 40 atm, about 50 atm, about 60 atm, about 70 atm, about 80 atm, about 90 atm, about 100 atm, about 110 atm, about 120 atm, about 130 atm, about 140 atm, about 150 atm, about 160 atm, about 170 atm, about 180 atm, about 190 atm, or about 200 atm.

[0133] In some embodiments, the interior of the aerosol dispensing container is lined with an inert polymer.

[0134] In some embodiments, the interior of the aerosol dispensing container is substantially free of transition metals (e.g., the interior of the container does not include transition metals). For example, the interior of the container does not substantially include salts and complexes containing transition metals. In some embodiments, the interior of the container is substantially free of chromium, manganese, copper, iron, cobalt, zinc, silver and / or mercury. For example, the interior of the container is substantially free of chromium. For example, the interior of the container is substantially free of manganese. For example, the interior of the container is substantially free of copper. For example, the interior of the container is substantially free of iron. For example, the interior of the container is substantially free of cobalt. For example, the interior of the container is substantially free of zinc. For example, the interior of the container is substantially free of silver. For example, the interior of the container is substantially free of mercury.

[0135] In some embodiments, the aerosol dispensing container comprises metal (eg, stainless steel or aluminum).

[0136] In certain embodiments, the aerosol dispensing container comprises an outlet valve through which the composition is dispensed. In some of these embodiments, the aerosol dispensing container further comprises a nozzle. In some of these embodiments, activating the nozzle (e.g., pressing or pushing down the nozzle) opens the outlet valve to dispense the composition.

[0137] method

[0138] In another aspect, disclosed herein is a method of maintaining the freshness of a plant, comprising contacting the plant with a composition described herein.

[0139] In some embodiments, the contacting comprises spraying the composition on the plant.

[0140] In some embodiments, the contact occurs before the plant is harvested by contacting (e.g., spraying) the composition on the plant. For example, the composition is sprayed in a field or orchard. In some other embodiments, the contact occurs after the plant is harvested. For example, the composition is sprayed on the plant stored in a room, chamber, container or truck. In some embodiments thereof, the plant is packaged in, for example, boxes, baskets, flower baskets, pallet containers, cartons, lugs, flat panels, crates, bags, sacks, sandwich containers and / or bulk boxes. In some embodiments thereof, the packaging is ventilated. In other embodiments thereof, the packaging is airtight.

[0141] In some embodiments, the plant is a fruit or vegetable. For example, the plant is a fruit. For example, the fruit is a banana, apple, pear, peach, plum, melon (such as cantaloupe, honeydew or watermelon), orange, grape, strawberry, blueberry, kiwi, apricot, mango, nectarine, papaya, plum, persimmon, lime or pineapple. For example, the fruit is a banana, peach, grape, strawberry or blueberry. For example, the plant is a vegetable. For example, the vegetable is a tomato, onion, cucumber, avocado, broccoli, carrot, gherkin, cabbage, radish, eggplant, aubergine, bell pepper, pepper, lettuce, chicory, spinach or garlic. For example, the vegetable is a tomato.

[0142] In some embodiments, the plant is a flower. For example, the flower is a rose, carnation, tulip, daisy, sunflower, daffodil, orchid, iris, lilac, gardenia, jasmine, magnolia, hyacinth or lily of the valley.

[0143] In another aspect, disclosed herein is a method of packaging a plant, comprising:

[0144] Place the plant in the chamber;

[0145] adding any composition described herein to the interior of the chamber, wherein the composition is a gas; and

[0146] Pack the plants in the chamber.

[0147] In some of these embodiments, the packaging is selected from the group consisting of a box, a basket, a flower basket, a pallet container, a carton, an ear bag, a flat panel, a crate, a bag, a sack, a sandwich container, and / or a bulk box. In some of these embodiments, the packaging is ventilated. In some of these embodiments, the packaging is ventilated. In other of these embodiments, the packaging is airtight.

[0148] In some embodiments, the plant is a fruit or vegetable. For example, the plant is a fruit. For example, the fruit is a banana, apple, pear, peach, plum, melon (such as cantaloupe, honeydew or watermelon), orange, grape, strawberry, blueberry, kiwi, apricot, mango, nectarine, papaya, plum, persimmon, lime or pineapple. For example, the fruit is a banana, peach, grape, strawberry or blueberry. For example, the plant is a vegetable. For example, the vegetable is a tomato, onion, cucumber, avocado, broccoli, carrot, gherkin, cabbage, radish, eggplant, aubergine, bell pepper, pepper, lettuce, chicory, spinach or garlic. For example, the vegetable is a tomato.

[0149] In some embodiments, the plant is a flower. For example, the flower is a rose, carnation, tulip, daisy, sunflower, daffodil, orchid, iris, lilac, gardenia, jasmine, magnolia, hyacinth or lily of the valley.

[0150] In another aspect, disclosed herein is a method of storing 1-methylcyclopropene, comprising:

[0151] Add 1-methylcyclopropene to the container;

[0152] adding a stabilizer into the container;

[0153] Among them, the concentration of 1-methylcyclopropene remained essentially unchanged after at least one day.

[0154] The prerequisite is that 1-methylcyclopropene does not complex with other molecules.

[0155] In some embodiments, the stabilizer is as defined above. In some embodiments, the amount of 1-methylcyclopropene is as defined above. In some embodiments, the amount of stabilizer is as defined above.

[0156] In some embodiments, the concentration of 1-methylcyclopropene is substantially unchanged after at least 4 hours. For example, the concentration of 1-methylcyclopropene is substantially unchanged for at least 4 hours, at least 8 hours, at least 12 hours, at least 16 hours, at least 20 hours, at least 24 hours, at least 28 hours, at least 32 hours, at least 36 hours, at least 40 hours, at least 44 hours, at least 48 hours, at least 2.5 days, at least 3 days, at least 3.5 days, at least 4 days, at least 5 days, at least 6 days, at least 7 days, at least 8 days, at least 9 days, at least 10 days, at least 20 days, at least 4 weeks, at least 2 months, at least 3 months, at least 4 months, at least 5 months, at least 6 months, at least 7 months, at least 8 months, at least 9 months, at least 10 months, at least 11 months, at least 1 year, at least 1.5 years, at least 2 years, at least 3 years, at least 4 years, at least 5 years, or at least 10 years.

[0157] In some embodiments, the composition comprises substantially no water (e.g., the composition comprises no water). In some embodiments, the composition comprises less than 5% by weight of water. For example, the composition comprises less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, or less than 0.1% water by weight. In some embodiments (when the composition is in the form of a gas), the humidity of the gas is less than 100%. For example, the humidity of the gas is less than 90%, less than 80%, less than 50%, less than 30%, less than 20%, less than 10%, less than 5%, less than 2%, or less than 1%.

[0158] In some embodiments, the container is a canister. In other embodiments, the container is a tank. In some embodiments, the container is a gas cylinder. In some embodiments, the container is a flask. In some embodiments, the container is a bag. In some embodiments, a valve is attached to the container so that the composition can enter or leave the container. In some embodiments, the container comprises aluminum. In some embodiments, the container comprises steel. In some embodiments, the interior of the container is lined with an inert polymer. In some embodiments, the interior of the container is substantially free of transition metals (e.g., the interior of the container is free of transition metals). For example, the interior of the container is substantially free of salts and complexes of transition metals. In certain embodiments, the interior of the container is substantially free of chromium, manganese, copper, iron, cobalt, zinc, silver and / or mercury. For example, the interior of the container is substantially free of chromium. For example, the interior of the container is substantially free of manganese. For example, the interior of the container is substantially free of copper. For example, the interior of the container is substantially free of iron. For example, the interior of the container is substantially free of cobalt. For example, the interior of the container is substantially free of zinc. For example, the interior of the container is substantially free of silver. For example, the interior of the container is substantially free of mercury.

[0159] In some embodiments (when the container is a bag), the bag is inside a metal can, metal box, or metal cylinder. In some embodiments (when the container is a bag inside a metal can, metal box, or metal cylinder), a valve is attached to the bag that can open and close the bag. In some of these embodiments, the composition can be released from the bag by pushing air inside the metal can, metal box, or metal cylinder.

[0160] In another aspect, disclosed herein is a method of storing 1-methylcyclopropene comprising cooling the 1-methylcyclopropene to a temperature below -40°C, wherein less than 10% of the 1-methylcyclopropene decomposes after one day.

[0161] In some embodiments, the 1-methylcyclopropene is cooled to less than -50° C., less than -60° C., less than -70° C., less than -80° C., less than -90° C., less than -100° C., less than -110° C., less than -120° C., less than -130° C., less than -140° C., less than -150° C., less than -160° C., less than -170° C., less than -180° C., or less than -190° C. In some embodiments, the 1-methylcyclopropene is cooled to a temperature of about -78° C. or about -195° C.

[0162] In some embodiments, less than 10% of the 1-methylcyclopropene decomposes after one day. For example, less than 9%, less than 8%, less than 7%, less than 6%, less than 5%, less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, or less than 0.1% of the 1-methylcyclopropene decomposes after one day.

[0163] In some embodiments, less than 10% of the 1-methylcyclopropene decomposes after one day. For example, less than 10% of the 1-methylcyclopropene decomposes after 2 days, 3 days, 5 days, 1 week, 2 weeks, 4 weeks, 2 months, 3 months, 4 months, 5 months, 6 months, 7 months, 8 months, 9 months, 1 year, 1.5 years, or 2 years.

[0164] In another aspect, disclosed herein is a method of improving the health of a plant comprising contacting the plant with a composition described herein.

[0165] In another aspect, disclosed herein is a method for preparing 1-methylcyclopropene, comprising:

[0166] reacting a base with 3-chloro-2-methylpropene to form 1-methylcyclopropene; and

[0167] The 1-methylcyclopropene was condensed at a temperature below -40°C.

[0168] In some embodiments, the base is sodium amide, potassium amide, sodium hydride, potassium hydride, n-butyl lithium, phenyl lithium, lithium diisopropylamide, lithium diethylamide, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide. In some embodiments, the base is sodium amide.

[0169] In some embodiments, 1-methylcyclopropene is condensed at a temperature below -50°C, below -60°C, or below -70°C. In some embodiments, 1-methylcyclopropene is condensed at a temperature of about -78°C.

[0170] In some embodiments, the reaction is carried out in a solvent such as toluene or benzene. For example, the reaction is carried out in toluene.

[0171] In some embodiments, the concentration of the base in the solvent is about 0.1 to about 5 g / mL, for example, about 0.1 to about 0.5 g / mL, about 0.5 to about 1 g / mL, about 1 g / mL to about 2 g / mL, about 2 g / mL to about 3 g / mL, about 3 g / mL to about 4 g / mL, about 4 g / mL to about 5 g / mL, about 0.5 g / mL to about 2 g / mL, about 0.5 g / mL, about 1 g / mL, or about 2 g / mL.

[0172] In some embodiments, the reaction comprises adding 3-chloro-2-methylpropene to a base. In some of these embodiments, the reaction comprises adding 3-chloro-2-methylpropene dropwise to a base. In some embodiments, the molar ratio of 3-chloro-2-methylpropene to the base is 2:1. In some embodiments, about 0.3 to about 5 molar equivalents of base are used, equivalent to 3-chloro-2-methylpropene. For example, about 0.3 to about 3 molar equivalents, about 0.67 to about 2 molar equivalents, about 0.67 to about 1 molar equivalent, about 1 to about 2 molar equivalents, about 0.67 molar equivalents, about 1 molar equivalent, about 1.5 molar equivalents, or about 2 molar equivalents of base are used, equivalent to 3-chloro-2-methylpropene.

[0173] In some embodiments, after the reaction, 1-methylcyclopropene is passed through an acid (e.g., sulfuric acid) and / or water. For example, after the reaction, 1-methylcyclopropene is first passed through an acid (e.g., sulfuric acid) and then through water.

[0174] In some embodiments, condensing comprises collecting the 1-methylcyclopropene in a container (e.g., a glass container) cooled to less than -40° C. (e.g., less than -50° C., less than -60° C., less than -70° C., or about -78° C.). In some embodiments, condensing comprises passing the 1-methylcyclopropene through a glass-filled condenser system prior to collecting the 1-methylcyclopropene in the container (e.g., a glass container).

[0175] In another aspect, disclosed herein is a method of preparing any of the compositions disclosed herein, comprising:

[0176] At a temperature below -40°C, 1-methylcyclopropene is condensed into a container containing a stabilizer.

[0177] In some embodiments, the stabilizer is as defined above. In some embodiments, the amount of 1-methylcyclopropene is as defined above. In some embodiments, the amount of stabilizer is as defined above. In some embodiments, the other features of the composition are as described anywhere herein.

[0178] In some embodiments, the method further comprises reacting a base with 3-chloro-2-methylcyclopropene to form 1-methylcyclopropene prior to condensing the 1-methylcyclopropene.

[0179] In some embodiments, the base is sodium amide, potassium amide, sodium hydride, potassium hydride, n-butyl lithium, phenyl lithium, lithium diisopropylamide, lithium diethylamide, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide. In some embodiments, the base is sodium amide.

[0180] In some embodiments, 1-methylcyclopropene is condensed at a temperature below -50°C, below -60°C, or below -70°C. In some embodiments, 1-methylcyclopropene is condensed at a temperature of about -78°C.

[0181] In some embodiments, the reaction is carried out in toluene or benzene. For example, the reaction is carried out in toluene.

[0182] In some embodiments, the reaction comprises adding 3-chloro-2-methylpropene to a base. In some of these embodiments, the reaction comprises adding 3-chloro-2-methylpropene dropwise to a base.

[0183] In some embodiments, after the reaction, 1-methylcyclopropene is passed through an acid (eg, sulfuric acid) and / or water. For example, after the reaction, 1-methylcyclopropene is first passed through an acid (eg, sulfuric acid) and then through water.

[0184] In some embodiments, the condensing comprises collecting the 1-methylcyclopropene in a container (e.g., a glass container) cooled to less than -40°C (e.g., less than -50°C, less than -60°C, less than -70°C, or about -78°C). In some embodiments, the condensing comprises passing the 1-methylcyclopropene through a condenser system filled with glass before collecting the 1-methylcyclopropene in the container (e.g., a glass container).

[0185] The present invention will be further described by the following examples.

[0186] Example 1. Preparation of 1-methylcyclopropene

[0187]

[0188] Toluene (300-2000 ml) and sodium amide (20 g-180 g; equivalent to about 0.67 to 2 molar equivalents of 3-chloro-2-methylpropene, dissolved in toluene at a concentration of about 0.75 g / ml) are placed in a reactor (1-6 L capacity) equipped with a high-efficiency condenser and a closed stirrer in argon. After the mixture is brought to reflux, 2-200 ml of 3-chloro-2-methylpropene is added dropwise until all 3-chloro-2-methylpropene is consumed. The escaping gas can be passed through sulfuric acid to remove ammonia. The gaseous 1-MCP is then passed through a scrubber filled with water. Subsequently, the 1-MCP is passed through a condenser system filled with glass and collected by condensation in a glass container cooled to -78°C (by immersion in a dry ice / acetone bath). The liquid 1-methylcyclopropene is expanded into a gas in a 500 ml Tedlar bag.

[0189] To a 250 ml amber glass bottle equipped with a nitrogen-flushed gas-tight valve was added 250 L of cis-2-butene and 250 L of 1-methylcyclopropene gas obtained from a Tedlar sampling bag. The mixture was analyzed by gas chromatography (GC) and the concentration of 1-methylcyclopropene was tested to determine its stability in the presence of cis-2-butene. Cis-2-butene can also be used as a reference for gas chromatography because it reacts the same as 1-methylcyclopropene in the FID detector. 250 μL of the 1-methylcyclopropene and cis-2-butene mixture was collected with a gas-tight syringe and injected into the gas chromatograph. The gas chromatograph was equipped with a PoraBONDQ column: 25 m × 0.255 mm inner diameter (id) × 3 μm and a flame ionization detector (FID). The conditions used were as follows: 10 split / splitless injector temperature 120°C; isothermal temperature 120°C, FID detector temperature 240°C, split 20:1, carrier gas (helium) flow 50 cm / s.

[0190] Liquid composition

[0191] Example 2

[0192] The 1-MCP formed by the synthesis process described in Example 1 was condensed into the container previously containing the liquid propellant. Then, cis-2-butene was condensed into the container.

[0193] The resulting composition contained 10% by weight of 1-methylcyclopropene and 0.5% by weight of cis-2-butene (equivalent to 5% of 1-methylcyclopropene). The liquid propellant was a mixture of propane and butane.

[0194] The weight percentage of dimer (which is the product of 1-MCP decomposition) in the samples was measured at different time points by gas chromatography. The results are shown in Tables 1 and Figure 1 middle.

[0195] Figure 1 .Relationship between the weight percentage of dimer in the sample and time

[0196] Time (hours) Dimer % 4.0 0.654 67.0 2.058 75.0 5.682 91.0 6.510 99.0 5.871 115.0 8.953 123.0 14.440 139.0 46.003

[0197] Example 3

[0198] A composition was prepared containing 10 wt% of 1-methylcyclopropene, 0.7 wt% of cis-2-butene (equivalent to 7% of 1-methylcyclopropene) and 89.3 wt% of a mixture of propane and butane.

[0199] The weight percentage of dimer in the samples was measured at different time points by gas chromatography. The results are shown in Tables 2 and Figure 2 It can be seen that increasing the amount of cis-2-butene to 7% (from 5% as described in Example 2) slows down the rate of dimer formation.

[0200] Figure 2 .Relationship between the percentage of dimers in the sample and time

[0201]

[0202]

[0203] Example 4

[0204] A composition comprising 10 wt% of 1-methylcyclopropene, 0.3 wt% of cis-2-butene (equivalent to 3% of 1-methylcyclopropene), and isobutane was prepared.

[0205] The percentage of dimers in the samples was measured at different time points by gas chromatography. The results are shown in Tables 3 and Figure 3 middle.

[0206] Figure 3 .Relationship between the percentage of dimers in the sample and time

[0207] Time (hours) Dimer % 18.0 0.488 26.0 0.439 42.0 0.937 50.0 8.030 66.0 8.165 74.0 9.563 90.0 11.522 115.0 1.588 122.0 6.040 139.0 3.403 146.0 2.237 332.0 4.334 400.0 5.254

[0208] Example 5

[0209] A composition comprising 5 wt% of 1-methylcyclopropene, 0.15 wt% of cis-2-butene (equivalent to 3% of 1-methylcyclopropene), and isobutane was prepared.

[0210] The percentage of dimers in the samples was measured at different time points by gas chromatography. The results are shown in Tables 4 and Figure 4 middle.

[0211] Figure 4 .The relationship between the percentage of dimers in the sample and time.

[0212] Time (hours) Dimer % 15.00 0.429 22.00 0.439 39.00 0.824 46.00 0.538 232.00 1.584

[0213] Gaseous composition

[0214] Example 6

[0215] The 1-MCP formed by the synthesis process described in Example 1 is expanded (i.e. allowed to become gas) into a glass container with an airtight valve and supplemented with appropriate gases (such as nitrogen, oxygen, carbon dioxide and / or argon) and stabilizers.

[0216] The composition comprises 1-MCP, cis-2-butene and carbon dioxide, wherein the concentrations of 1-MCP and cis-2-butene are 0.1% volume / volume respectively.

[0217] Table 5 and Figure 5The changes in the peak area ratio of 1-MCP:cis-2-butene measured by gas chromatography at different time points are shown. Table 6 compares the peak area ratios at the first measurement (day 1) and the 59th day measurement, which shows that the concentration of 1-MCP remains essentially unchanged after 59 days.

[0218] Table 5. Relationship between the GC peak area ratio of 1-MCP:cis-2-butene and time in the presence of carbon dioxide

[0219]

[0220] Table 6. Changes in 1-MCP concentration after 59 days

[0221]

[0222]

[0223] Example 7

[0224] 1-MCP formed by the synthesis process described in Example 1 was expanded (ie, allowed to become gas) into a glass container with an airtight valve and supplemented with appropriate gas and stabilizers.

[0225] The composition comprises 1-MCP, cis-2-butene and nitrogen (250 mL). The concentrations of 1-MCP and cis-2-butene are 0.1% v / v, respectively.

[0226] Table 7 and Figure 6 The changes in the peak area ratio of 1-MCP:cis-2-butene measured by gas chromatography at different time points are shown. Table 8 compares the peak area ratios at the first measurement (day 1) and the 59th day measurement, which shows that the concentration of 1-MCP remains essentially unchanged after 59 days.

[0227] Table 7. GC peak area ratio of 1-MCP:cis-2-butene versus time in the presence of nitrogen

[0228]

[0229]

[0230] Table 8. Changes in 1-MCP concentration after 59 days

[0231] Days 1-MCP% 1 100.0 59 95.17

[0232] Example 8

[0233] 1-MCP formed by the synthesis process described in Example 1 was expanded (ie, allowed to become gas) into a glass container with an airtight valve and supplemented with appropriate gas and stabilizers.

[0234] The composition comprises 1-MCP, cis-2-butene and nitrogen. The concentrations of 1-MCP and cis-2-butene are 0.1% v / v respectively.

[0235] Table 9 and Figure 7 1-MCP measured by gas chromatography: the peak area ratio of cis-2-butene changes at different time points. Table 10A compares the peak area ratios measured for the first time (day 1) and the 182nd day, showing that the concentration of 1-MCP remains essentially unchanged after 182 days. Table 10B compares the peak area ratios measured for the first time (day 1) and the 557th day, showing that the concentration of 1-MCP changes very little after 557 days.

[0236] Table 9. GC peak area ratio of 1-MCP:cis-2-butene versus time in the presence of nitrogen

[0237]

[0238]

[0239] Table 10A. Changes in 1-MCP concentration after 182 days

[0240] Days 1-MCP% 1 100.0 182 97.15

[0241] Table 10B. Changes in 1-MCP concentration after 557 days

[0242] Days 1-MCP% 1 100.0 557 89.82

[0243] Example 9

[0244] 1-MCP formed by the synthesis process described in Example 1 was expanded (ie, allowed to become gas) into a glass container with an airtight valve and supplemented with appropriate gas and stabilizers.

[0245] The composition comprises 1-MCP, cis-2-butene and nitrogen. The concentrations of 1-MCP and cis-2-butene are 5% volume / volume respectively.

[0246] Table 11 and Figure 8 1-MCP measured by gas chromatography: the peak area ratio of cis-2-butene changes at different time points. Table 12A compares the peak area ratios measured for the first time (day 1) and the 182nd day, showing that the concentration of 1-MCP remains essentially unchanged after 182 days. Table 12B compares the peak area ratios measured for the first time (day 1) and the 310th day, showing that the concentration of 1-MCP remains essentially unchanged after 310 days.

[0247] Table 11. Relationship between the GC peak area ratio of 1-MCP:cis-2-butene and time in the presence of nitrogen

[0248]

[0249]

[0250] Table 12A. Changes in 1-MCP concentration after 182 days

[0251] Days 1-MCP% 1 100.0 182 95.10

[0252] Table 12B. Changes in 1-MCP concentration after 310 days

[0253] Days 1-MCP% 1 100.0 310 89.34

[0254] Example 10

[0255] 1-MCP formed by the synthesis process described in Example 1 was expanded (ie, allowed to become gas) into a glass container with an airtight valve and supplemented with appropriate gas and stabilizers.

[0256] The composition comprises 1-MCP, cis-2-butene and nitrogen. The concentrations of 1-MCP and cis-2-butene are 10% volume / volume, respectively.

[0257] Table 13 and Fig. 9 The changes in the peak area ratio of 1-MCP:cis-2-butene measured by gas chromatography at different time points are shown. Table 14 compares the peak area ratios at the first measurement (day 1) and the 182nd day measurement, which shows that the concentration of 1-MCP remains essentially unchanged after 182 days.

[0258] Table 13. GC peak area ratio of 1-MCP:cis-2-butene versus time in the presence of nitrogen

[0259]

[0260]

[0261] Table 14. Changes in 1-MCP concentration after 182 days

[0262]

[0263] Example 11.

[0264] 1-MCP formed by the synthesis described in Example 1 was expanded (ie allowed to become a gas) into a glass container with an airtight valve. Cis-2-butene and nitrogen were added.

[0265] The resulting composition contained 1-MCP, cis-2-butene and nitrogen. The concentration of 1-MCP was 10% v / v and the concentration of cis-2-butene was 0.1% v / v (equivalent to 1% of the added volume of 1-MCP).

[0266] Table 15A and Fig. 10A (Graph with circular data points) shows the percentage of dimers in samples measured by gas chromatography at different time points over 219.5 hours. Table 15B and Fig. 10B (Graph with circular data points) shows the percentage of dimer in samples measured by gas chromatography at different time points over 147 days.

[0267] Table 15A. Percent Dimer in Sample vs. Time (in Hours)

[0268] Time (hours) Dimer % 0.25 0.145 24.25 0.135 47.5 0.275 120 0.600 148.75 0.882 194.25 0.936 219.5 1.507

[0269] Table 15B. Percent dimer in samples versus time (in days).

[0270]

[0271]

[0272] Example 12.

[0273] 1-MCP formed by the synthesis described in Example 1 was expanded (ie allowed to become a gas) into a glass container with an airtight valve. Cis-2-butene and nitrogen were added.

[0274] The resulting composition contained 1-MCP, cis-2-butene and nitrogen. The concentration of 1-MCP was 10% v / v and the concentration of cis-2-butene was 1% v / v (equivalent to 10% of the added volume of 1-MCP).

[0275] Table 16A and Fig. 10A (Graph with square data points) shows the percentage of dimers in samples measured by gas chromatography at different time points over 219.5 hours. Table 16B and Fig. 10B (Graph with square data points) shows the percentage of dimer in samples measured by gas chromatography at different time points over 147 days.

[0276] Table 16A. Percent Dimer in Samples vs. Time (in Hours)

[0277] Time (hours) Dimer % 0.5 0.128 24.5 0.172 47.75 0.307 120.25 0.777 149 0.952 194.5 1.184 219.5 1.732

[0278] Table 16B. Relationship between the percentage of dimers in samples and time (in days)

[0279]

[0280]

[0281] Example 13.

[0282] 1-MCP formed by the synthesis described in Example 1 was expanded (ie allowed to become a gas) into a glass container with an airtight valve. Cis-2-butene and nitrogen were added.

[0283] The resulting composition contained 1-MCP, cis-2-butene and nitrogen. The concentration of 1-MCP was 10% v / v and the concentration of cis-2-butene was 5% v / v (equivalent to 50% of the added volume of 1-MCP).

[0284] Table 17A and Fig. 10A (Graph with triangle data points) shows the percentage of dimer measured by gas chromatography at different time points over 219.75 hours. Table 17B and Fig. 10B (Graph with triangular data points) shows the percentage of dimer in samples measured by gas chromatography at different time points over 147 days.

[0285] Table 17A. Percent dimer in samples versus time (in hours).

[0286] Time (hours) Dimer % 0.75 0.146 24.75 0.236 48.25 0.317 120.5 0.786 149.25 0.896 194.75 1.155 219.75 1.864

[0287] Table 17B. Percent dimer in samples versus time (in hours).

[0288]

[0289]

[0290] Example 14.

[0291] The liquid 1-MCP produced by the reaction of Example 1 was expanded into a glass container with an airtight valve and supplemented with appropriate gas and stabilizer.

[0292] 1-MCP and butane were mixed in a liquid form at a ratio of 1:1 (volume ratio). The mixture was then transferred to a glass container.

[0293] Table 18 and Fig.11 (Graph with circular data points) shows the percentage of dimer in the composition measured by gas chromatography at different time points. The dashed line is the trend line, which is extrapolated to the 1-MCP / butane graph. A negative control containing only 1-MCP was used as a comparison. Table 19 and Fig.11(Graph with square data points) shows the percentage of dimer in the negative control measured by gas chromatography at the same time points as the composition was measured. Tables 18-19 and Fig.11 It is shown that the presence of butane greatly reduces the rate of dimer formation, thereby stabilizing 1-MCP. Table 20 shows the percentage of 1-MCP in the sample versus time, indicating that its concentration does not change significantly over time.

[0294] Table 18. Relationship between the percentage of dimers in samples and time

[0295]

[0296] Table 19. Percent dimer in negative control group versus time.

[0297] Time (hours) Dimer % 1 0.229 3.75 0.401 25.75 4.013 123.5 49.588

[0298] Table 20. Percent 1-MCP in samples versus time.

[0299] Time (hours) 1-MCP% 0 44.79 3.25 40.34 5 42.70 23.25 43.19 95.25 42.20 172 38.81 197.25 41.56 1483.25 41.96

[0300] Exemplary Embodiments

[0301] 1. A composition comprising:

[0302] 1-Methylcyclopropene; and

[0303] Stabilizers;

[0304] Among them, the concentration of 1-methylcyclopropene remained essentially unchanged after at least 4 hours;

[0305] The prerequisite is that 1-methylcyclopropene does not complex with other molecules.

[0306] 2. The composition as described in embodiment 1, wherein the stabilizer is selected from the group consisting of lower alkanes, lower olefins, lower dialkyl ethers, lower trialkylamines, and combinations thereof.

[0307] 3. A composition as described in any of embodiments 1-2, wherein the stabilizer comprises cis-2-butene.

[0308] 4. The composition of any one of embodiments 1-3, wherein the composition comprises from about 0.1 wt % to about 50 wt % 1-methylcyclopropene.

[0309] 5. The composition of any one of embodiments 1-4, wherein the composition comprises from about 0.1 wt % to about 10 wt % of a stabilizer.

[0310] 6. The composition of any one of embodiments 1-5, wherein the composition is a liquid.

[0311] 7. The composition of any one of embodiments 1-6, wherein the concentration of 1-methylcyclopropene remains substantially unchanged after at least 4 weeks.

[0312] 8. The composition as described in embodiment 6, further comprising:

[0313] Solvents; and

[0314] At least one component selected from the group consisting of a polymer, a plasticizer, a surfactant and an adjuvant.

[0315] 9. The composition of any one of embodiments 1-5 and 7, wherein the composition is a gas and further comprises nitrogen, oxygen and carbon dioxide.

[0316] 10. The composition of embodiment 9, wherein the composition comprises about 1 wt % to about 10 wt % of 1-methylcyclopropene.

[0317] 11. The composition of embodiment 9, wherein the composition comprises about 1% to about 10% by volume of 1-methylcyclopropene.

[0318] 12. A composition as described in any of embodiments 9-10, wherein the composition comprises about 80 wt % to about 94 wt % nitrogen; about 3 wt % to about 10 wt % oxygen; and about 3 wt % to about 10 wt % carbon dioxide.

[0319] 13. A composition as described in any of embodiments 9 and 11, wherein the composition comprises about 80 volume % to about 94 volume % nitrogen; about 3 volume % to about 10 volume % oxygen; and about 3 volume % to about 10 volume % carbon dioxide.

[0320] 14. The composition of any one of embodiments 9-10 and 12, wherein the composition comprises from about 0.1 wt % to about 10 wt % of a stabilizer.

[0321] 15. The composition of any one of embodiments 9, 11, and 13, wherein the composition comprises about 0.1% to about 10% by volume of a stabilizer.

[0322] 16. An aerosol dispensing container containing the composition of any one of embodiments 1-8, wherein the composition is under a pressure greater than 1 atm.

[0323] 17. An aerosol dispensing container as described in embodiment 16, wherein the composition further comprises a propellant.

[0324] 18. An aerosol dispensing container according to any one of embodiments 16-17, wherein the composition further comprises:

[0325] Solvents; and

[0326] At least one component selected from the group consisting of a polymer, a plasticizer, a surfactant and an adjuvant.

[0327] 19. The aerosol dispensing container of any one of embodiments 16-18, wherein the composition is stored at a pressure of about 2 atm to about 10 atm.

[0328] 20. The aerosol dispensing container of any one of embodiments 16-18, wherein the composition is stored at a pressure of about 10 atm to about 100 atm.

[0329] 21. An aerosol dispensing container as described in any of embodiments 16-20, wherein the interior of the container is substantially free of transition metals.

[0330] 22. A method for maintaining the freshness of a plant, comprising contacting the plant with the composition of any one of embodiments 1-15.

[0331] 23. The method of embodiment 22, wherein the plant is a fruit or a vegetable.

[0332] 24. The method of embodiment 22, wherein the plant is a flower.

[0333] 25. The method of any one of embodiments 22-24, wherein the contacting comprises spraying the composition of any one of embodiments 1-15 onto the plant.

[0334] 26. A method of packaging plants, comprising:

[0335] Place the plant in the chamber;

[0336] adding the composition of any one of embodiments 9-15 to the interior of the chamber; and

[0337] Pack the plants in the chamber.

[0338] 27. The method of embodiment 26, wherein the plant is a fruit or a vegetable.

[0339] 28. The method of embodiment 26, wherein the plant is a flower.

Claims

1. A composition comprising: 1-Methylcyclopropene, and Stabilizers; in, The concentration of 1-methylcyclopropene remained essentially unchanged after at least 4 hours; The prerequisite is that 1-methylcyclopropene does not complex with other molecules.

2. The composition according to claim 1, in, The stabilizer is selected from the group consisting of lower alkanes, lower olefins, lower dialkyl ethers, lower trialkylamines and combinations thereof.

3. The composition according to any one of claims 1 to 2, in, The stabilizer comprises cis-2-butene.

4. The composition according to any one of claims 1 to 3, in, The composition comprises from about 0.1 wt % to about 50 wt % 1-methylcyclopropene.

5. The composition according to any one of claims 1 to 4, in, The composition comprises from about 0.1 wt % to about 10 wt % of a stabilizer.

6. The composition according to any one of claims 1 to 5, in, The composition is a liquid.

7. The composition according to any one of claims 1 to 6, in, The concentration of 1-methylcyclopropene remained essentially unchanged after at least 4 weeks.

8. The composition of claim 6, further comprising Solvents; and At least one component selected from the group consisting of a polymer, a plasticizer, a surfactant and an adjuvant.

9. The composition according to any one of claims 1 to 5 and 7, in, The composition is a gas and further comprises nitrogen, oxygen and carbon dioxide.

10. The composition according to claim 9, in, The composition comprises from about 1 wt % to about 10 wt % 1-methylcyclopropene.

11. The composition according to claim 9, in, The composition comprises from about 1% to about 10% by volume of 1-methylcyclopropene.

12. The composition according to any one of claims 9 to 10, in, The composition comprises from about 80 wt % to about 94 wt % nitrogen; from about 3 wt % to about 10 wt % oxygen; and from about 3 wt % to about 10 wt % carbon dioxide.

13. The composition according to any one of claims 9 and 11, in, The composition comprises from about 80% to about 94% by volume nitrogen; from about 3% to about 10% by volume oxygen; and from about 3% to about 10% by volume carbon dioxide.

14. A composition as claimed in any one of claims 9 to 10 and 12, in, The composition comprises from about 0.1 wt % to about 10 wt % of a stabilizer.

15. The composition according to any one of claims 9, 11 and 13, in, The composition comprises from about 0.1% to about 10% by volume of a stabilizer.

16. An aerosol dispensing container containing a composition according to any one of claims 1 to 8, in, The composition is under a pressure greater than 1 atm.

17. An aerosol dispensing container according to claim 16, in, The composition further comprises a propellant.

18. An aerosol dispensing container according to any one of claims 16 to 17, in, The composition further comprises: Solvents; and At least one component selected from the group consisting of a polymer, a plasticizer, a surfactant and an adjuvant.

19. An aerosol dispensing container according to any one of claims 16 to 18, in, The composition is stored at a pressure of about 2 atm to about 10 atm.

20. An aerosol dispensing container according to any one of claims 16 to 18, in, The composition is stored at a pressure of about 10 atm to about 100 atm.

21. An aerosol dispensing container according to any one of claims 16 to 20, in, The interior of the container is substantially free of transition metals.

22. A method for maintaining the freshness of plants, comprising contacting the plants with the composition of any one of claims 1-15.

23. The method of claim 22, in, The plant is a fruit or a vegetable.

24. The method of claim 22, in, The plants are flowers.

25. The method of any one of claims 22-24, wherein the contacting comprises spraying the composition of any one of claims 1-15 onto the plant.

26. A method of packaging plants, comprising: Place the plant in the chamber; adding the composition of any one of claims 9-15 to the interior of the chamber; and Pack the plants in the chamber.

27. The method of claim 26, in, The plant is a fruit or a vegetable.

28. The method of claim 26, in, The plants are flowers.

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