NZ718340B2 - Systems and methods for solvent-free delivery of volatile compounds - Google Patents
Systems and methods for solvent-free delivery of volatile compounds Download PDFInfo
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- NZ718340B2 NZ718340B2 NZ718340A NZ71834014A NZ718340B2 NZ 718340 B2 NZ718340 B2 NZ 718340B2 NZ 718340 A NZ718340 A NZ 718340A NZ 71834014 A NZ71834014 A NZ 71834014A NZ 718340 B2 NZ718340 B2 NZ 718340B2
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- cyclodextrin
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- 150000001875 compounds Chemical class 0.000 title abstract description 17
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- 244000018676 Rosa sp Species 0.000 description 1
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- 241000109329 Rosa xanthina Species 0.000 description 1
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- 235000004191 Rubus ursinus Nutrition 0.000 description 1
- 240000000856 Rubus ursinus Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000203383 Schefflera Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
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- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
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- 240000008529 Triticum aestivum Species 0.000 description 1
- 241000722921 Tulipa gesneriana Species 0.000 description 1
- 241000191891 Tulipa hybrid cultivar Species 0.000 description 1
- 235000004224 Typha angustifolia Nutrition 0.000 description 1
- 235000005391 Typha capensis Nutrition 0.000 description 1
- 235000019026 Typha domingensis Nutrition 0.000 description 1
- 235000005324 Typha latifolia Nutrition 0.000 description 1
- 240000000260 Typha latifolia Species 0.000 description 1
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 1
- 240000000851 Vaccinium corymbosum Species 0.000 description 1
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
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- 241000219094 Vitaceae Species 0.000 description 1
- 229920004482 WACKER® Polymers 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- OVIUDBHLSJZYPU-UHFFFAOYSA-N [N-]=[N+]=NCl(=O)=O Chemical compound [N-]=[N+]=NCl(=O)=O OVIUDBHLSJZYPU-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000017585 alfalfa Nutrition 0.000 description 1
- 235000017587 alfalfa Nutrition 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000000676 alkoxyimino group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 1
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- 125000005282 allenyl group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- 235000021014 blueberries Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 235000008984 brauner Senf Nutrition 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
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- 125000001651 cyanato group Chemical group [*]OC#N 0.000 description 1
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
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- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 1
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- 150000002118 epoxides Chemical class 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 235000002532 grape seed extract Nutrition 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
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- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 1
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- 235000002741 hibiscus rosa-sinensis Nutrition 0.000 description 1
- 235000002294 holly Nutrition 0.000 description 1
- 235000002296 holly Nutrition 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 1
- 235000006677 lemon beebalm Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 235000004383 oregano Nutrition 0.000 description 1
- 210000000056 organs Anatomy 0.000 description 1
- 235000018838 origanum vulgare Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 125000005493 quinolyl group Chemical group 0.000 description 1
- 235000021013 raspberries Nutrition 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QXTIBZLKQPJVII-UHFFFAOYSA-N triethylsilicon Chemical group CC[Si](CC)CC QXTIBZLKQPJVII-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 235000021307 wheat Nutrition 0.000 description 1
- 235000005765 wild carrot Nutrition 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/20—Combustible or heat-generating compositions
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N27/00—Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
- A23B7/144—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of gases, e.g. fumigation; Compositions or apparatus therefor
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B9/00—Preservation of edible seeds, e.g. cereals
- A23B9/16—Preserving with chemicals
- A23B9/18—Preserving with chemicals in the form of gases, e.g. fumigation; Compositions or apparatus therefor
Abstract
Provided are systems and methods for solvent-free delivery of volatile compounds, where an energy source is used to release the volatile compounds. The systems and methods provided herein have the features of (1) no solvent (for example water) is required; (2) immediate release of volatile compounds (for example 1-MCP can be released from a complex with alpha-cyclodextrin within milliseconds or seconds instead of minutes or hours of the existing method using water); and/or (3) instantly starting and stopping the delivery of the volatile compound. (for example 1-MCP can be released from a complex with alpha-cyclodextrin within milliseconds or seconds instead of minutes or hours of the existing method using water); and/or (3) instantly starting and stopping the delivery of the volatile compound.
Description
SYSTEMS AND S FOR SOVLENT-FREE DELIVERY
OF VOLATILE COMPOUNDS
BACKGROUND OF THE INVENTION
Previous experiments showed that when molecular complexes of volatile
compounds (for e 1-methylcyclopropene ) complexed with alphacyclodextrin
, the powder of which is also known as High Active Ingredient Product (HAIP))
are heated, there is significant weight loss which has been uted to the decomposition of
the volatile compound. Since it is known that 1-MCP (a typical active volatile compound)
decomposes when heated, it is assumed that 1-MCP is degraded when its molecular complex
is heated to high temperatures (for example - 200 °C).
It is well known that 1-MCP is liberated froman alpha-cyclodextrin/1-MCP
x with humidity. Currently all commercial generators of 1-MCP use water to generate
1-MCP for treating a variety of fruits and vegetables. However, the existing method has a
drawback in that the release of 1-MCP requires an ed period of time (for example one
hour), and is sensitive to the quality of the water used.
Thus, there remains a need for systems and methods for solvent-free delivery of
volatile compounds including 1-MCP.
SUMMARY OF THE INVENTION
This invention is based on surprising results that heating a molecular complex of
1-MCP and alpha-cyclodextrin (for example HAIP) can generate pure 1-MCP without
significant loss. Provided are systems and methods for solvent-free delivery of volatile
compounds, where an source is used to e the volatile compounds. The s and
methods ed herein have at least one advantage of (1) no solvent (for e water) is
required; (2) immediate release of volatile compounds (for example 1-MCP can be released
from HAIP within econds or seconds instead of minutes or hours of the existing method
using water); and/or (3) instantly starting and stopping the delivery of the volatile compound.
In one aspect, provided is a solvent-free system for delivery of a volatile
compound. The system comprises (a) a molecular x of the volatile compound with a
molecular encapsulating agent; (b) a treatment compartment; and (2) an energy source.
In another aspect, provided is a solvent-free system for ry of a volatile
compound. The system comprises (a) a molecular complex of the volatile compound with a
molecular encapsulating agent; (b) a treatment compartment; and (2) means of energy source.
In one embodiment, the system further ses an mer. In a further
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embodiment, the elastomer comprises ethylene vinyl acetate. Additional suitable mers
are described in US Patent ations 2006/0233857 and 2012/0273586, the contents of
which are incorporated by reference in their entireties.
In one embodiment, the cyclopropene is of the formula:
I>—R
wherein R is a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl,
cycloalkylalkyl, phenyl, or naphthyl group; n the substituents are ndently
halogen, alkoxy, or tuted or unsubstituted phenoxy.
In a further embodiment, R is C1-C8 alkyl. In another embodiment, R is methyl.
In one embodiment, the cyclopropene is of the formula:
R3 R4
R1 R2
wherein R1 is a substituted or unsubstituted C1—C4 alkyl, C1-C4 alkenyl, C1-C4 alkynyl, C1-C4
cycloalkyl, cycloalkylalkyl, phenyl, or napthyl group; and R2, R3, and R4 are hydrogen.
In a further embodiment, the cyclopropene is l-methylcyclopropene (l—MCP).
In one embodiment, the ropene is part of a cyclopropene molecular
complex. In another embodiment, the cyclopropene molecular complex is an inclusion
complex. In another embodiment, the cyclopropene molecular complex comprises a
ropene and a lar encapsulating agent. In a r embodiment, the molecular
encapsulating agent is selected from the group consisting of substituted cyclodextrins,
unsubstituted cyclodextrins, crown ethers, zeolites, and combinations thereof. In a further
embodiment, the molecular encapsulating agent comprises a cyclodextrin. In another
embodiment, the molecular encapsulating agent is selected from the group consisting of
alpha-cyclodextrin, beta-cyclodextrin, gamma—cyclodextrin, and combinations thereof. In a
further embodiment, the molecular encapsulating agent comprises alpha-cyclodextrin.
In one embodiment, the treatment compartment is selected from the group
ting of a thermal desorption tube, a glass , a Tedlar bag, an aluminum cup, and
ations thereof. In another ment, the energy source comprises at least one of
electrical , magnetic energy, electromagnetic energy, ultrasonic energy, acoustic
energy, and thermal energy. In another embodiment, the energy source comprises at least
one energy characteristic of waveform, frequency, amplitude, or duration. In a further
embodiment, the energy source comprises ultraviolet (UV) radiation. In another
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embodiment, the energy source does not comprise UV radiation.
In one embodiment, the energy source is provided by heating to a ature
between 100 °C and 300 °C; 150 0C and 250 0C; 180 OC and 220 °C; or about 200 0C. In
r embodiment, the means of energy source comprises heating to a temperature between
100 °C and 300 0C; 150 0C and 250 0C; 180 0C and 220 °C; or about 200 °C. In another
ment, the means of energy source is performed in an ed environment. In a
further embodiment, the enclosed environment the enclosed environment includes a cold
storage room/facility, a refrigerator, a shipping container, and combinations thereof. In a
further embodiment, the enclosed environment is ed from the group consisting of a cold
storage room/facility, a refrigerator, a shipping container, and combinations thereof. In
another embodiment, the means of energy source is performed in an environment at a
temperature between -30 0C and 10 °C; between -20 °C and 5 °C; between -10 0C and 0 0C; or
about 4 0C. In a further embodiment, the means of energy source is performed in a cold
storage room or cold storage facility.
In another embodiment, the energy source is provided by passing a hot air. In
r embodiment, the means of energy source comprising passing a hot air. In one
embodiment, the hot air ses an inert gas. In a further ment, the inert gas is
. In another embodiment, the hot air is at a temperature n 100 0C and 300 °C;
150 0C and 250 0C; 180 0C and 220 0C; or about 200 0C.
In another aspect, provided is method for delivery of a volatile compound. The
method comprises (a) providing a lar complex of the volatile compound with a
molecular ulating agent; (b) placing the molecular complex into a ent
compartment; and (c) applying an energy source to the treatment compartment, thereby
releasing the volatile compound from the molecular complex.
In another aspect, provided is method for delivery of a volatile compound. The
method comprises (a) providing a lar complex of the volatile compound with a
molecular encapsulating agent; (b) placing the molecular complex into a treatment
compartment; and (c) applying means of energy source to the treatment compartment,
thereby releasing the volatile compound from the molecular complex.
In one embodiment, loss of the volatile compound is less than 40%, 30%; 20%;
%; or 5%. In another embodiment, loss of the volatile compound is between 40% and
0.5%; between 30% and 1%; n 20% and 3%; or between 10% and 5%. In another
embodiment, the systems provided herein are used. The loss of the volatile compound is
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defined as comparison between amount of encapsulated volatile compound and amount of
recovered volatile compound after release.
In one embodiment, the cyclopropene is of the formula:
[>—R
n R is a substituted or unsubstituted alkyl, alkenyl, alkynyl, lkyl,
cycloalkylalkyl, phenyl, or naphthyl group; wherein the tuents are independently
halogen, alkoxy, or substituted or unsubstituted phenoxy.
In a further embodiment, R is C1-C3 alkyl. In r embodiment, R is .
In one embodiment, the cyclopropene is of the formula:
R3 R4
R1 R2
wherein R1 is a substituted or unsubstituted C1-C4 alkyl, C1-C4 alkenyl, C1-C4 alkynyl, C1—C4
cycloalkyl, cycloalkylalkyl, phenyl, or napthyl group; and R2, R3, and R4 are hydrogen.
In a further ment, the cyclopropene is l-methylcyclopropene (l-MCP).
In one embodiment, the cyclopropene is part of a ropene molecular
complex. In another ment, the cyclopropene molecular complex is an inclusion
complex. In another embodiment, the cyclopropene molecular complex comprises a
cyclopropene and a molecular encapsulating agent. In a r embodiment, the molecular
encapsulating agent is selected from the group consisting of substituted cyclodextrins,
unsubstituted cyclodextrins, crown ethers, zeolites, and combinations thereof. In a further
embodiment, the molecular encapsulating agent comprises a cyclodextrin. In another
embodiment, the molecular encapsulating agent is selected from the group consisting of
alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, and combinations thereof. In a
further ment, the molecular encapsulating agent comprises cyclodextrin.
In one embodiment, the treatment compartment is selected from the group
consisting of a thermal desorption tube, a glass bottle, a Tedlar bag, an um cup, and
combinations thereof. In r embodiment, the energy source comprises at least one of
electrical , magnetic energy, electromagnetic energy, ultrasonic energy, acoustic
energy, and thermal energy. In another embodiment, the energy source comprises at least
one energy characteristic of waveform, frequency, ude, or duration. In a further
embodiment, the energy source comprises UV radiation. In another embodiment, the energy
source does not comprise UV radiation.
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In one embodiment, the energy source is provided by heating to a temperature
between 100 0C and 300 0C; 150 0C and 250 °C; 180 0C and 220 0C; or about 200 0C. In
another embodiment, the means of energy source comprises g to a temperature between
100 0C and 300 0C; 150 0C and 250 0C; 180 °C and 220 0C; or about 200 0C. In another
embodiment, the means of energy source is med in an ed environment. In a
further embodiment, the enclosed environment the enclosed environment includes a cold
storage room/facility, a refrigerator, a shipping container, and combinations thereof. In a
further embodiment, the enclosed environment is selected from the group consisting of a cold
storage room/facility, a refrigerator, a shipping container, and combinations thereof. In
another ment, the means of energy source is performed in an environment at a
temperature between —30 0C and 10 0C; n —20 °C and 5 0C; between —10 0C and 0 0C; or
about 4 0C. In a further embodiment, the means of energy source is performed in a cold
storage room or cold storage facility.
In another embodiment, the energy source is provided by g a hot air. In
another embodiment, the means of energy source comprising passing a hot air. In one
embodiment, the hot air comprises an inert gas. In a r embodiment, the inert gas is
helium. In another embodiment, the hot air is at a temperature between 100 0C and 300 0C;
150 °C and 250 0C; 180 0C and 220 °C; or about 200 °C.
In another aspect, provided is a method of ng ripening for the plant or plant
parts. In one ment, the method comprises treating the plant or plant part using the
systems provided . In another embodiment, the method comprises treating the plant or
plant part using the methods provided herein.
In another , provided is a device for solvent-free delivery of volatile
compounds. In one embodiment, the device ses components disclosed in the systems
provided herein. Additional suitable devices are described in US Patent Numbers 7,540,286,
7,832,410, US Patent Application 2006/0037998, and international patent application WO
2013/034453, the contents of which are incorporated by nce in their entireties.
BRIEF DESCRIPTION OF THE DRAWINGS
shows a representative schematic of a vaporizer as part of the systems
provided herein, where 101 refers to the Air inlet, 102 refers to the Fan, 103 refers to the
Heater, 104 refers to the Sample holder, 105 refers to the Air outlet.
shows a representative schematic of a generator as part of the systems
provided herein, where 201 refers to the Sample cup, 202 refers to the Gas outlet, 203 refers
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to the Aluminum top, 204 refers to the Nitrogen (N2) inlet, 205 refers to the Silicone gasket,
206 refers to the tion, 207 refers to the Aluminum block, 208 refers to the .
DETAILED DESCRIPTION OF THE INVENTION
This invention relates to generating l-MCP gas by heating HAIP (l-MCP/alpha-
cyclodextrin complex). Results of the subject invention show that upon heating the 0i-
cyclodextrin/l-MCP complex, it is possible to quantitatively generate l-MCP. In one
ment, surprising data from thermogravimetric analysis—mass spectrometry (TGA-MS)
show that heating HAIP to a ature of about 200 0C can generate pure l-MCP. In
another embodiment, provided are treatment protocols that do not e water but can
generate l-MCP in milliseconds. In another embodiment, delivery systems and/or device to
generate l-MCP by heating the HAIP are provided.
The results of the subject invention are surprising because a number of studies
have established the fact that at temperatures higher than 100 °C l-MCP degrades to other
molecules. (See e. g., Srinivasan, R. Journal of the American Chemical Society, 1969, 91,
6250-6253; Hopf, H.; Wachholz, G.; Walsh, R. Chemische Berichte, 1985, 118, 3579-3587).
As used herein, a cyclopropene is any compound with the formula
R3 R4
R1‘ ‘RZ
wherein 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
wherein n is an integer from 0 to 12. Each L is a bivalent radical. Suitable L groups e,
for example, radicals containing one or more atoms selected from H, 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 R], 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 drogen atoms is 50 or less.
Each 2 is a monovalent l. Each Z is ndently selected from the group consisting
of hydrogen, halo, cyano, nitro, o, azido, chlorate, bromate, iodate, isocyanato,
nido, isothiocyanato, luorothio, and a chemical group G, wherein G is a 3 to 14
membered ring system.
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The R1, R2, R3, and R4 groups are independently selected from the suitable groups.
The R1, R2, R3, and R4 groups may be the same as each other, or any number of them may be
different from the others. Among the groups that are le for use as one or more of R],
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, ns, silyl groups, other , and
es and combinations thereof. Groups that are suitable for use as one or more of R1, R2,
R3, and R4 may be substituted or unsubstituted. Independently, groups that are suitable for
use as one or more of R1, R2, R3, and R4 may be connected directly to the cyclopropene ring
or may be ted to the cyclopropene ring through an intervening group such as, for
example, a heteroatom-containing group.
Among the le R1, R2, R3, and R4 groups are, for example, aliphatic groups.
Some suitable aliphatic groups include, but are not limited to, alkyl, alkenyl, and alkynyl
groups. Suitable aliphatic groups may be , branched, cyclic, or a combination f.
Independently, suitable aliphatic groups may be substituted or unsubstituted.
As used herein, a chemical group of interest is said to be ituted" if one or
more hydrogen atoms of the chemical group of interest is replaced by a substituent. It is
contemplated that such substituted groups may be made by any method, including but not
limited to making the unsubstituted form of the chemical group of st and then
performing a substitution. Suitable substituents include, but are not limited to, alkyl, alkenyl,
acetylamino, alkoxy, alkoxy, carbonyl, alkoxyimino, carboxy, halo, haloalkoxy,
hydroxy, alkylsulfonyl, alkylthio, trialkylsilyl, dialkylamino, and ations thereof. An
additional suitable substituent, which, if present, may be present alone or in combination with
another suitable substituent, is
-(L)m-Z
wherein m is 0 to 8, and L and Z are defined . If more than one substituent is present
on a single chemical group of interest, each substituent may replace a different hydrogen
atom, or one substituent may be attached to another substituent, which in turn is attached to
the chemical group of interest, or a combination thereof.
Among the suitable R1, R2, R3, and R4 groups are, without limitation, substituted
and tituted aliphatic-oxy groups, such as, for example, alkenoxy, alkoxy, alkynloxy,
and alkoxycarbonyloxy.
Also among the suitable R], R2, R3, and R4 groups are, without limitation,
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substituted and unsubstituted alkylphosphonato, substituted and unsubstituted
alkylphosphato, substituted and tituted alkylamino, substituted and unsubstituted
alkylsulfonyl, substituted and unsubstituted alkylcarbonyl, and substituted and tituted
alkylaminosulfonyl, including, Without limitation, alkylphosphonato, dialkylphosphato,
lthiophosphato, dialkylamino, alkylcarbonyl, and dialkylaminosulfonyl.
Also among the le R], R2, R3, and R4 groups are, Without limitation,
substituted and unsubstituted lkylsulfonyl groups and cycloalkylamino groups, such as,
for example, dicycloalkylaminosulfonyl and dicycloalkylamino.
Also among the suitable R], R2, R3, and R4 groups are, Without limitation,
substituted and unsubstituted heterocyclyl groups (i.e., aromatic or non-aromatic cyclic
groups with at least one heteroatom in the ring).
Also among the suitable R], R2, R3, and R4 groups are, Without limitation,
substituted and unsubstituted cyclyl groups that are connected to the cyclopropene
compound h 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, Without limitation,
substituted and unsubstituted aryl groups. Suitable substituents include those described
herein above. In some embodiments, one or more substituted aryl group may be used in
which at least one tuent is one or more of alkenyl, alkyl, alkynyl, acetylamino,
alkoxyalkoxy, , alkoxycarbonyl, carbonyl, alkylcarbonyloxy, carboxy, arylamino,
haloalkoxy, halo, hydroxy, trialkylsilyl, dialkylamino, alkylsulfonyl, ylalkyl, alkylthio,
thioalkyl, arylaminosulfonyl, and haloalkylthio.
Also among the suitable R1, R2, R3, and R4 groups are, without limitation,
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 roarylaminosulfonyl.
Also among the suitable R], R2, R3, and R4 groups are, Without limitation,
hydrogen, fluoro, chloro, bromo, iodo, cyano, nitro, nitroso, azido, chlorato, o, iodato,
isocyanato, isocyanido, isothiocyanato, pentafluorothio, acetoxy, carboethoxy, cyanato,
nitrato, nitrito, perchlorato, allenyl, butylmercapto, lphosphonato, dimethylphenylsilyl,
isoquinolyl, mercapto, naphthyl, phenoxy, phenyl, piperidino, pyridyl, quinolyl, triethylsilyl,
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trimethylsilyl, and substituted analogs thereof.
As used herein, the chemical group G is a 3- to l4-membered ring system. Ring
systems suitable as chemical group G may be substituted or unsubstituted; they may be
aromatic ding, for example, phenyl and napthyl) or aliphatic (including unsaturated
tic, partially saturated aliphatic, or saturated aliphatic); and they may be carbocyclic or
heterocyclic. Among cyclic G , some suitable heteroatoms are, without
limitation, 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 ic ring may be fused with an aliphatic ring).
In some embodiments, G is a ring system that contains a ted or unsaturated
3 membered ring, such as, without tion, a substituted or unsubstituted cyclopropane,
cyclopropene, epoxide, or aziridine ring.
In some embodiments, G is a ring system that contains a 4-membered heterocyclic
ring; in some of such embodiments, the heterocyclic ring contains exactly one heteroatom. In
some embodiments, G is a ring system that contains a heterocyclic ring with 5 or more
members; in some of such embodiments, the heterocyclic ring contains 1 to 4 heteroatoms.
In some embodiments, the ring in G is tituted; in other ments, the ring system
contains 1 to 5 substituents; in some embodiments in which G contains substituents, each
substituent may be independently chosen from the substituents described herein above. Also
suitable are embodiments in which G is a carbocyclic ring system.
In some embodiments, each G is independently a substituted or unsubstituted
, pyridyl, cyclohexyl, cyclopentyl, cycloheptyl, yl, furyl, thiophenyl, triazolyl,
pyrazolyl, 1,3-dioxolanyl, or morpholinyl. Among these embodiments are included those
embodiments, for example, in which G is unsubstituted or substituted phenyl, cyclopentyl,
cycloheptyl, or cyclohexyl. In some embodiments, G is cyclopentyl, cycloheptyl, cyclohexyl,
phenyl, or tuted phenyl. Among embodiments in which G is substituted phenyl are
embodiments, without limitation, in which there are l, 2, or 3 substituents. In some
embodiments in which G is substituted phenyl are embodiments, without limitation, in which
the substituents are independently selected from , y, and halo.
Also contemplated are embodiments in which R3 and R4 are combined into a
single group, which may be attached to the number 3 carbon atom of the cyclopropene ring
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by a double bond. Some of such compounds are described in US Patent Publication
2005/0288189.
In some embodiments, one or more ropenes may be used in which one or
more of R1, R2, R3, and R4 is hydrogen. In some embodiments, R1 or R2 or both R1 and R2
may be hydrogen. In some embodiments, R3 or R4 or both R3 and R4 may be hydrogen. In
some embodiments, R2, R3, and R4 may be en.
In some ments, one or more of R1, R2, R3, and R4 may be a structure that
has no double bond. Independently, in some embodiments, one or more of R1, R2, R3, and R4
may be a structure that has no triple bond. In some embodiments, one or more of R1, R2, R3,
and R4 may be a structure that has no halogen atom substituent. In some embodiments, one
or more of R1, R2, R3, and R4 may be a structure that has no substituent that is ionic.
In some embodiments, one or more of R1, R2, R3, and R4 may be hydrogen or (C1-
C10) alkyl. In some embodiments, each of R1, R2, R3, and R4 may be hydrogen or (C1-C8)
alkyl. In some embodiments, each of R1, R2, R3, and R4 may be hydrogen or (C1-C4) alkyl.
In some embodiments, each of R1, R2, R3, and R4 may be hydrogen or methyl. In some
embodiments, R1 may be ) alkyl and each of R2, R3, and R4 may be hydrogen. In some
embodiments, R1 may be methyl and each of R2, R3, and R4 may be hydrogen, and the
cyclopropene is known herein as “l-methylcyclopropene” or “l-MCP.”
In some embodiments, a cyclopropene may be used that has a boiling point at one
atmosphere pressure of 50°C or lower; or 25°C or lower; or 15°C or lower. In some
embodiments, a cyclopropene may be used that has a boiling point at one atmosphere
pressure of -100°C or higher; -50°C or higher; or -25°C or higher; or 0°C or higher.
The cyclopropenes may be prepared by any method. Some suitable methods of
preparation of cyclopropenes include, but are not limited to, the processes disclosed in U.S.
Patent Nos. 5,518,988 and 6,017,849.
In some embodiments, the composition may include at least one molecular
encapsulating agent for the cyclopropene. In some embodiments, at least one molecular
encapsulating agent may ulate one or more cyclopropene or a portion of one or more
ropene. A complex that contains a cyclopropene le or a portion of a
cyclopropene molecule encapsulated in a le of a molecular encapsulating agent is
known herein as a “cyclopropene molecular complex” or “cyclopropene nd
complex.” In some embodiments, ropene molecular complexes may comprise at least
1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 20, 30, 32, 40, 50, 60, 70, 80, or 90% weight by weight (w/w) of
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the solution.
In some embodiments, at least one cyclopropene molecular complex may be
present as an inclusion complex. In such an inclusion x, the molecular encapsulating
agent forms a , and the cyclopropene or a n of the cyclopropene is located within
that cavity. In some embodiments of inclusion complexes, there may be no covalent bonding
between the cyclopropene and the molecular encapsulating agent. In some ments of
inclusion complexes, there may be no ionic g between the cyclopropene and the
molecular encapsulating agent, whether or not there is any electrostatic attraction between
one or more polar moiety in the cyclopropene and one or more polar moiety in the molecular
encapsulating agent.
In some embodiments of inclusion complexes, the interior of the cavity of the
molecular encapsulating agent may be substantially apolar or hobic or both, and the
cyclopropene (or the portion of the cyclopropene located within that cavity) is also
substantially apolar or hydrophobic or both. While the present invention is not limited to any
particular theory or mechanism, it is contemplated that, in such apolar cyclopropene
molecular complexes, van der Waals forces, or hydrophobic interactions, or both, cause the
cyclopropene molecule or portion thereof to remain within the cavity of the molecular
encapsulating agent.
The cyclopropene molecular complexes may be prepared by any means. In one
method of preparation, for example, such complexes may be prepared by ting the
cyclopropene with a solution or slurry of the molecular encapsulating agent and then isolating
the complex, using, for example, processes disclosed in U. S. Patent No. 6,017,849. For
e, in another method of making a complex in which cyclopropene is encapsulated in a
molecular encapsulating agent, the cyclopropene gas may be bubbled through a on of
molecular encapsulating agent in water, from which the complex first itates and is then
isolated by filtration. In some embodiments, complexes may be made by either of the above
methods and, after isolation, may be dried and stored in solid form, for e as a powder,
for later addition to useful compositions.
The amount of molecular encapsulating agent may be characterized by the ratio of
moles of molecular encapsulating agent to moles of ropene. In some embodiments, the
ratio of moles of molecular encapsulating agent to moles of cyclopropene may be 0.1 or
larger; 0.2 or larger; 0.5 or larger; or 0.9 or larger. In some embodiments, the ratio of moles
of molecular ulating agent to moles of cyclopropene may be 2 or lower; or 1.5 or
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lower.
Suitable molecular encapsulating agents include, without limitation, organic and
inorganic lar encapsulating agents. Suitable organic lar encapsulating agents
include, without limitation, substituted cyclodextrins, unsubstituted extrins, and crown
ethers. le inorganic molecular encapsulating agents include, without limitation,
zeolites. Mixtures of suitable molecular encapsulating agents are also suitable. In some
embodiments, the encapsulating agent may be alpha-cyclodextrin, beta-cyclodextrin,
gamma-cyclodextrin, or a mixture thereof. In some embodiments, alpha-cyclodextrin may be
used. In some embodiments, the encapsulating agent may vary depending upon the structure
of the cyclopropene or cyclopropenes being used. Any cyclodextrin or mixture of
cyclodextrins, cyclodextrin polymers, modified cyclodextrins, or mixtures thereof may also
be ed. Some cyclodextrins are available, for example, from Wacker Biochem Inc.,
Adrian, MI or Cerestar USA, Hammond, IN, as well as other s.
Energy sources - suitable main sources of energy that can be utilized include
conduction, convection and radiation. Conduction energy can be generated by electrical
resistance (6. g., cartridge heaters, formed resistance wire, ceramic heaters, band heaters, wire
film heaters and thin flexible heaters). Convection heating can be achieved by flowing
heated gas or by flowing heated . Radiation energy sources include lasers, microwave
and infra red for example.
Embodiments e s of treating plants with the systems and/or s
described herein. In some embodiments, ng the plant or plant parts with the systems
and/or methods provided inhibits the ethylene response in the plant or plant parts. The term
” is used generically to also e woody-stemmed plants in addition to field crops,
potted plants, cut flowers, harvested fruits and vegetables and ornamentals. Examples of
plants that can be treated by embodiments include, but are not limited to, those listed below.
In some embodiments, a plant or plant part may be treated with levels of
cyclopropene that t the ethylene response in the plant or plant part. In some
embodiments, a plant or plant part may be treated at levels that are below phytotoxic levels.
The phytotoxic level may vary not only by plant but also by cultivar. Treatment may be
performed on growing plants or on plant parts that have been harvested from growing plants.
It is contemplated that, in performing the treatment on growing plants, the composition may
be contacted with the entire plant or may be contacted with one or more plant parts. Plant
parts include any part of a plant, including, but not limited to, flowers, buds, blooms, seeds,
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cuttings, roots, bulbs, fruits, vegetables, leaves, and combinations f. In some
embodiments, plants may be treated with compositions described herein prior to or after the
harvesting of the useful plant parts.
Suitable treatments may be performed on a plant or plant parts in a field, in a
garden, in a building (such as, for example, a greenhouse), in an ed container or in
another location. Suitable treatments may be performed on a plant that is planted in open
ground, in one or more containers (such as, for example, a pot, planter, or vase), in confined
or raised beds, or in other places. In some embodiments, ent may be performed on a
plant that is in a location other than in a building. In some embodiments, a plant may be
treated while it is growing in a container such as, for example, a pot, flats, or portable bed. In
another embodiment, the systems and methods provided are performed within an enclosed
nment. In a further embodiment, the enclosed environment es a cold storage
room, a erator, a shipping ner, or combinations thereof.
When correctly used, the systems and s described herein prevent numerous
ne effects, many of which have been disclosed in US. Patent Nos. 5,518,988 and
3,879,188, both of which are orated herein by reference in their ties. The
embodiments described herein may be employed to influence one or more of the plant
ethylene responses. Ethylene responses may be initiated by either exogenous or endogenous
sources of ethylene. Ethylene responses include, but are not limited to, (i) the ripening and/or
senescence of flowers, fruits and vegetables, (ii) the abscission of foliage, flowers and fruit,
(iii) the prolongation of the life of ornamentals, such as potted plants, cut flowers, shrubbery
and dormant seedlings, (iv) the inhibition of growth in some plants such as the pea plant, and
(v) the stimulation of plant growth in some plants such as the rice plant.
Vegetables which may be treated to inhibit senescence include, but are not limited
to, leafy green vegetables such as lettuce (e. g., Lactuca sativa), h (Spinacia oleracea)
and cabbage (Brassica oleracea); various roots such as potatoes (Solanum tuberosum) and
carrots (Daucus carota); bulbs such as onions (Allium sp.); herbs such as basil (0cimum
basilicum), oregano (Origanum e) and dill (Anethum graveolens); as well as soybean
(Glycine max), lima beans (Phaseolus limensis), peas (Lathyrus sp.), corn (Zea mays),
broccoli (Brassica oleracea italica), cauliflower (Brassica oleracea botrytis) and asparagus
(Asparagus oflicinalis).
Fruits which may be treated by the methods of the present invention to inhibit
ripening include, but are not limited to, tomatoes (Lycopersicon esculentum), apples (Malus
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ica), bananas (Musa sapientum), pears (Pyrus communis), papaya (Carica papaya),
mangoes (Mangifera indica), peaches (Prunus persica), apricots (Prunus armeniaca),
nectarines (Prunus persica nectarina), oranges (Citrus sp.), lemons s limonia), limes
(Citrus aurantifolia), grapefruit (Citrus paradisi), tangerines (Citrus nobilis deliciosa), kiwi
(Actinidia chinensis), melons such as cantaloupes (C. cantalupensis) and musk melons (C.
melo), pineapples (Ananas comosus), persimmon (Diospyros sp.) and raspberries (e. g.,
Fragaria or Rubus ursinus), blueberries (Vaccinium sp.), green beans (Phaseolus vulgaris),
members of the genus Cucumis such as cucumber (C. sativus) and avocados (Persea
americana).
Ornamental plants which may be treated by the methods of the present invention
to inhibit ence and/or to prolong flower life and appearance (such as the delay of
wilting), include, but are not limited to, potted omamentals and cut flowers. Potted
ntals and cut flowers which may be treated include, but are not limited to, azalea
(Rhododendron spp.), hydrangea (Hydrangea macrophylla), hibiscus (Hibiscus rosa-
sinensis), snapdragons (Antirrhinum sp.), poinsettia (Euphorbia pulcherrima), cactus (e. g.,
Scnlumbergera truncata), begonias (Begonia sp.), roses (Rosa sp.), tulips (Tulipa sp.),
daffodils (Narcissus sp.), petunias (Petunia hybrida), ion (Dianthus caryopnyllus), lily
(e. g., Lilium sp.), gladiolus (Gladiolus sp.), Alstroemeria (Alstroemeria brasiliensis),
anemone (e.g., Anemone blanda), ine (Aquilegia sp.), aralia (e. g., Aralia chinesis),
aster (e. g., Aster carolinianus), nvillea (Bougainvillea sp.), camellia (Camellia sp.),
bellflower (Campanula sp.), cockscomb (Celosia sp.), falsecypress (Chamaecyparis sp.),
Chrysanthemum (Chrysanthemum sp.), clematis (Clematis sp.), cyclamen (Cyclamen sp.),
freesia (e. g., Freesia refracta), and s of the family Orchidaceae.
Plants which may be treated to inhibit abscission of foliage, flowers, and fruit
include, but are not limited to, cotton pium spp.), apples, pears, cherries (Prunus
avium), pecans (Carva illinoensis), grapes (Vitis vinifera), olives (e. g., Olea europaea),
coffee (Coflea arabica), snapbeans (Phaseolus vulgaris), and weeping fig (Ficus benjamina),
as well as dormant seedlings ing, but not limited to, those of various fruit trees
ing apple, ornamental plants, ery, and tree seedlings.
In addition, shrubbery which may be treated to inhibit abscission of foliage
include, but are not limited to, privet (Ligustrum sp.), photinea (Photina sp.), holly (Ilex sp.),
ferns of the family Polypodiaceae, schefflera ‘lera sp.), aglaonema (Aglaonema sp.),
cotoneaster (Cotoneaster sp.), barberry (Berberis sp.), waxmyrtle (Myrica sp.), abelia (Abelia
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sp.), acacia (Acacia sp.), and bromeliads of the family Bromeliaceae.
As used herein, the phrase “plant” includes dicotyledonous plants and
tyledonous plants. Examples of dicotyledonous plants, dicotyledon plants,
ledons, or dicots, include tobacco, Arabidopsis, soybean, tomato, papaya, canola,
er, cotton, alfalfa, potato, grapevine, pigeon pea, pea, Brassz'ca, chickpea, sugar beet,
rapeseed, watermelon, melon, pepper, peanut, pumpkin, radish, spinach, squash, li,
cabbage, carrot, cauliflower, celery, Chinese e, cucumber, eggplant, and lettuce.
Examples of monocotyledonous plants, monocotyledon plants, monocotyledons, or ts
e corn, rice, wheat, sugarcane, barley, rye, sorghum, orchids, bamboo, banana, cattails,
lilies, oat, onion, millet, and triticale.
As used herein, the phrase “plant al” refers to leaves, stems, roots, flowers
or flower parts, fruits, pollen, egg cells, zygotes, seeds, cuttings, cell or tissue cultures, or any
other part or product of a plant. In some ment, plant material es cotyledon and
leaf.
A used herein, the phrase “plant tissue” refers to a group of plant cells organized
into a structural and functional unit. Any tissue of a plant in planta or in e is included,
for example: whole plants, plant organs, plant seeds, tissue culture and any groups of plant
cells organized into structural and/or functional units.
Also provided are devices for solvent-free delivery of volatile compounds. In one
embodiment, the device comprises components disclosed in the systems provided .
Additional suitable devices are described in US Patent Nos 7,540,286 (inhalation device for
aerosol particles), 7,832,410 (device for e-cigarette), US Patent Application 2006/0037998
(thermally controlled actuator device), and international patent application
(new e-cigarette ), the contents of which are incorporated by reference in their
ties. Modification of these devices can be achieved based on properties of particular
volatile compounds to be delivered.
The present invention is further described in the following examples, which are
offered by way of illustration and are not intended to limit the invention in any manner.
EXAMPLES
Example 1
10.38 g of (x-cyclodextrin/l—MCP complex (supplied by AgroFresh, l-MCP =
3.8%) is put in a thermal desorption tube and desorbed, under a flow of 9.8 mL/min helium at
200 0C into a bag pre-filled with 800 ml of air. Total final volume of bag is 900 mL. The
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ce of 1-MCP is confirmed by mass spectrometry. The 1-MCP concentration,
determined by gas chromatography, is found to be 153 ppm. If all the 1-MCP present in the
starting sample is ted (with no degradation) then the concentration in the bag would be
197 ppm. Thus 78% of the theoretical amount of 1-MCP is obtained in the bag.
Example 2
0.57 mg of HAIP SF08016 (AgroFresh, 4.33% l-MCP) is added into a 123 mL
glass bottle and the bottle is closed (air-tight seal) with a port to draw gas sample for is
(HAIP stands for High Active ient Product which is the complex between 0t—
cyclodextrin and 1-MCP where the 1-MCP concentration is between 3.5 - 4.6 %). The bottle
is then heated at different temperatures for 30 min and the 1-MCP concentration in the bottle
is measured by gas chromatography and shown in Table 1.
Table 1. Percent (%) of recovery of 1-MCP at ent
temperatures
Temperature (°C) 1-MCP (ppm) % Recovered
0
50 0
0.66 mg of HAIP SF08016 (AgroFresh, 4.33% 1-MCP) is added into a 123 mL
glass bottle and the bottle is closed (air-tight seal) with a port to draw gas sample for analysis.
The bottle is then heated at 180 0C for 30 min and the 1—MCP concentration in the bottle is
measured by gas chromatography. The l-MCP concentration is 121 ppm. The calculated
value is 105 ppm.
Example 4
Using a commercial vaporizer (Extreme Q Vaporizer; see , a series of
experiments is performed using ent sources and amounts of HAIP. For all the
experiments listed below the heater is kept at 230 0C and the fan speed is set at the lowest
setting (F-l) which provides a flow rate of 954 milliliters per minute (mLfmin). The outlet
air is collected in Tedlar bags and the content is analyzed by gas chromatography to
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determine the l-MCP concentration using isobutylene as an external standard (A1203 refers to
aluminum oxide).
Table 2. Percent (%) l-MCP recovery from various HAIP preparations
Sample ID Amount (mg) HAIP form (additive) 1-MCP Yield (%)
TG2135-l 10.2 Powder (none) 18.7
TG2135-2 1.9 Powder (none) 36.8
TG2137-1A Powder (A1203, 10%) 43.3
-2A Powder (A1203, 50%) 74.1
TG2l4l-l Tablet (none) 66.1
TG2135-l Powder (none) 52.8
TG2141-1 190 Tablet (none) 66.1
Results in Table 2 indicate that by heating the complex between or-cyclodextrin
and l-MCP, pure l-MCP can be generated in high yields which can then be used to treat
fruits and vegetables.
Example 5
The cial vaporizer (Extreme Q Vaporizer; see is modified to
obtain lower flow rate. A series of experiments is performed using different sources and
amounts of HAIP.
For all the experiments listed below the heater is kept at 230 0C and a flow rate of
254 mL/min. The outlet air is collected in Tedlar bags, and the t is analyzed by gas
chromatography to determine the l-MCP concentration using ylene as an external
standard.
Table 3. Percent (%) l-MCP recovery from various HAIP preparations
Sample ID Amount (mg) HAIP form (additive) Time (min) l-MCP Yield (%)
TG2150—l 23.9 Powder (none) 15 85
TG2152-2 20.7 Powder (iron 67%)
TG2153-1 48.3 Powder (iron, 6.7%)_&
TG2154—2 17.1 Powder (iron, 6.7%)_—
Results in Table 3 indicate that by lowering the flow rate from 954 mL/min to 254
mL/min and by adding iron to the (x-cyclodextrin and l-MCP, the yield of l-MCP generated
can be increased.
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Using a newly designed generator that can heat tens of grams of HAIP (see , a series of experiments is performed using different amounts of HAIP and different block
temperatures. The outlet air is collected in large Tedlar bags (40 liter (L)), and the content is
analyzed by gas chromatography to determine the 1-MCP concentration using isobutylene as
an external standard.
Table 4. t (%) 1-mcp recovery from various amounts of HAIP and ent block
temperatures
1-MCP
Experiment '
- sed Outcome
lDi,2,3 (Mass
balance)
85% of l-hggljnliilliberated 1n
WJZ6544 2 (375) 1.61
89% of 1-MCP is ted in
92 8%
WJZ6545 2 (3.75) 180 0.27 9360/ 30 min. <0.1% 2-Butyne is
( ' 0) collected.
97.8% 95% of 1-MCP is liberated in30
WJZ6546 2 (3 62). 200 0 08. .
(92.9%) rmn.
91% of 1-MCP is liberated in
96 7%
WJZ6548 10 (3.65) 200 0.12 30 min. 0.2% 2-Butyne is
(96170) collected.
75% of 1-MCP is liberated in
93 2%
WJZ6552 20 (3.82) 200 0.26 86 (7 30 min. 0.1% 2-Butyne is
( 0) collected.
81% of 1-MCP is liberated in
97 9%
3 20 (3.78) 220 0.08 86.77 30 min. 0.4% 2-Butyne is
( ‘ 0) collected.
71.5% of 1-MCP is liberated in
min. The 1-MCP
concentration in the 3rd sample
92.5%
WJZ6555 30 (3.86) 200 0.29 bag is 946 ppm, so l-MCP is
(81 7(7)' 0
coming out during cool down
(~40 min). 0.3% 2-Butyne is
collected.
75.5% of 1-MCP is liberated in
min. The 1—MCP
concentration in the 3"d sample
96.2%
WJZ6557 30 (3.86) 220 0.15 bag is 637 ppm, so 1-MCP is
(795%)
coming out during cool down
(~40 min). 0.4% 2-Butyne is
collected.
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%AI = percent active ingredient
1Collection begins when block temperature is 120 OC
2N2 flow is 1 liter per minute (L/min)
3Run time is 90 min, with samples being collected at 30 minute intervals
The data in Table 4 clearly indicate that large quantities of HAIP can be heated to
te 1-MCP in high yields and in less than 60 min. In all of the ments, at least
71% of the l-MCP is liberated in 30 min. As the amount of HAIP is increased, the formation
of 2—butyne, albeit in very small quantities (S 0.4%), is observed.
To understand the heat flow from the heater block to the HAIP in a newly
designed generator that can heat tens of grams of HAIP (see , a series of experiments
is performed using different amounts of HAIP and different block temperatures. The
temperature of the bulk powder is measured throughout the heating process.
Table 5. Temperature profiles
Experiment Weight of Block Inside Tray Temperature (0C) after
ID HAIP Temperature
(0C)
WJZ6544 140
WJZ6546 200
WJZ6552 20 200 105.9 148.3 154.6
WJZ6553 20 220 112.8 169.3 174.8
30 200 102.4 147.8 165.0
7 30 220 109.1 162.4 181.3
Since alpha-cyclodextrin has a low thermal conductivity (0.0681 watts per meter
Kelvin (w/mOK at 20 OC and 0.0841 w/m0K at 150 OC) there is a sharp drop of temperature
from the outside of the sample cup to the bulk powder. With the block temperature set at 200
0C, the temperature of the bulk powder (after 30 min) drops from 140.5 0C, for a 2 g sample
46), to 105.9 0C for a 30 g sample (WJZ6552). In the 2 g experiment (WJZ6546), no
2-butyne is observed. Thus increasing the rate of 1-MCP generation by increasing the heat
transfer efficiency should reduce and possibly ate the formation of 2-butyne.
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In some embodiments, the present invention can be further modified within the
spirit and scope of this disclosure. This application is therefore intended to cover any
variations, uses, or tions of the invention using its general principles. Further, this
application is intended to cover such departures from the present disclosure as come within
known or customary ce in the art to which this invention pertains and which fall within
the limits of the appended claims.
1003212755
Claims (26)
1. A solvent-free system for ry of a volatile compound, comprising (a) a molecular complex of 1-methyl cyclopropene (1-MCP) and an inclusion complex comprising cyclodextrin; (b) a treatment compartment; and (c) means of energy source, wherein the solvent-free system is configured to release the volatile compound from the molecular complex t water.
2. The system of claim 1, r comprising an elastomer.
3. The system of claim 2, wherein the elastomer comprises ethylene vinyl acetate.
4. The system of any one of claim 1 to 3, n the cyclodextrin is selected from the group consisting of alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, and combinations thereof.
5. The system of any one of claims 1 to 4, wherein the treatment compartment is selected from the group consisting of a thermal desorption tube, a glass , a Tedlar bag, an aluminum cup, and combinations thereof.
6. The system of any one of claims 1 to 5, wherein the energy source comprises at least one of electrical energy, ic energy, electromagnetic energy, ultrasonic energy, acoustic energy, and thermal energy.
7. The system of any one of claims 1 to 6, n the energy source ses at least one energy characteristic of waveform, frequency, amplitude, or duration.
8. The system of any one of claims 1 to 7, wherein the means of energy source comprises heating to a temperature between 100 oC and 300 oC. 1003212755
9. The system of claim 8, wherein the means of energy source comprises heating to a ature between 150 oC and 250 oC.
10. The system of any one of claims 1-9, wherein the means of energy source is performed in an enclosed environment.
11. The system of any one of claims 1-10, wherein the means of energy source is performed in an environment at a temperature between -30 oC and 10 oC.
12. The system of any one of claims 1-11, wherein the means of energy source is performed in a cold storage room or cold storage facility.
13. A method for delivery of a volatile compound, comprising: (a) providing a molecular complex of 1-methyl ropene (1-MCP) and an inclusion complex comprising cyclodextrin; (b) placing the molecular complex into a ent compartment; and (c) applying means of energy source to the treatment compartment, thereby releasing the volatile compound from the molecular complex, wherein the method es the volatile compound from the molecular complex without water.
14. The method of claim 13, wherein loss of the volatile compound is less than 20%.
15. The method of claim 13 or 14, wherein the system of claim 1 is used.
16. The method of any one of claims 13 to 15, wherein the cyclodextrin is selected from the group consisting of alpha-cyclodextrin, yclodextrin, gamma-cyclodextrin, and ations thereof. 1003212755
17. The method of any one of claims 13 to 16, wherein the treatment compartment is selected from the group consisting of a thermal desorption tube, a glass bottle, a Tedlar bag, and an aluminum cup, combinations thereof.
18. The method of any one of claims 13 to 17, wherein the energy source comprises at least one of electrical energy, magnetic energy, electromagnetic energy, ultrasonic energy, acoustic energy, and thermal energy.
19. The method of any one of claims 13 to 18, wherein the energy source comprises at least one energy characteristic of waveform, frequency, amplitude, or duration.
20. The method of any one of claims 13 to 19, n the means of energy source comprises g to a temperature between 100 oC and 300 oC.
21. The method of any one of claims 13 to 20, wherein the means of energy source comprises heating to a temperature between 150 oC and 250 oC.
22. The method of any one of claims 13 to 21, wherein the means of energy source is performed in an enclosed environment.
23. The method of any one of claims 13 to 22, n the means of energy source is performed in an environment at a temperature between -30 oC and 10 oC.
24. The method of claims 13 to 23, wherein the means of energy source is med in a cold storage room or cold storage facility.
25. A method of delaying ripening for a plant or plant part, comprising ng the plant or plant part using the system of any one of claims 1 to 12.
26. A method of ng ripening for a plant or plant part, comprising treating the plant or plant part using the method of claim 13 to 24.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201361882378P | 2013-09-25 | 2013-09-25 | |
US61/882,378 | 2013-09-25 | ||
PCT/US2014/056488 WO2015047897A1 (en) | 2013-09-25 | 2014-09-19 | Systems and methods for solvent-free delivery of volatile compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ718340A NZ718340A (en) | 2020-10-30 |
NZ718340B2 true NZ718340B2 (en) | 2021-02-02 |
Family
ID=
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