ZA200505855B - Compositions with cyclopropenes and adjuvants - Google Patents

Compositions with cyclopropenes and adjuvants Download PDF

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Publication number
ZA200505855B
ZA200505855B ZA200505855A ZA200505855A ZA200505855B ZA 200505855 B ZA200505855 B ZA 200505855B ZA 200505855 A ZA200505855 A ZA 200505855A ZA 200505855 A ZA200505855 A ZA 200505855A ZA 200505855 B ZA200505855 B ZA 200505855B
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South Africa
Prior art keywords
composition
agents
adjuvants
metal
cyclopropenes
Prior art date
Application number
ZA200505855A
Inventor
Richard M Basel
Edward C Kostansek
Bridget M Stevens
Original Assignee
Rohm & Haas
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Publication date
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Priority to ZA200505855A priority Critical patent/ZA200505855B/en
Publication of ZA200505855B publication Critical patent/ZA200505855B/en

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Description

COMPOSATIONS WITH CYCLOPROPENES AND ADJUVANTS
BACKGROUND:
Ethylene can cause the premature death of plants or plant parts inclucling, for example, flowers, leaves, fruits, and vegetables through binding with certain receptors in the plant. Ethylene also promotes leaf yellowing and stunted growth as well as premature fruit, flower, and leaf drop. Cyclopropenes (i.e., substituted and unsubstituted cyclopropene and its derivatives) are effective agents for block ang the effects of ethylene. One difficulty in effectively contacting a plant or plant part with cyclopropeness is that many useful cyclopropenes are gasses at ambient conditions (10 to 35°C and approximately 1 atmosphere pressure); thus, in some cases, the cyclopropene tends to escape into the atmosphere instead of remaining in contact with the plant or pelant part (either on the surface or in the interior or the plant or plzant part). US 5,518,988 discloses applying mixtures of cyclopropenes and wettin_g agents to plants. It i s desired to provide compositions that can be contacted with plants or plant parts an d that have improved the effectiveness of cyclopropenes at blockzing the effects of ethylene.
STATEMENT OF THE INVENTION:
In the present invention, there is provided a composition comprising (2) one or more molecular encapsulation agents within each of which is encapsulated one or more cyclopropenes of the formula
CH
CH wherein said R is hydrogen or a substituted or unsubstituted alkyl, alkenyl. alkynyl, cycloalkyl, cycloalkylalkyl, phenyl, or naphthyl group; wherein thee substituents, when present, are independently halogen, alkoxy, or substituted or unsubstitu ted phenoxy; and } (b) one or more adjuvants sclected from the group consisting of surfactants, alcohols, hydrocarbon oils, and mixtures thereof.
SE to , 2005 ‘ones
DETAILED DESCRIPTION:
As used herein, all percentages are percent b-y weight and all parts are parts by weight, unless otherwise specified, and are inclusives and combinable. All ratios are by weight and all ratio ranges are inclusive and com binable. All molar ranges are inclusive and combinable.
As used herein, the term “alkyl” means straight chain, branched chain , or cyclic (C-Cyo) radicals which include, for example, methyl, ethyl, n-propyl, isopropyl, l-ethylpropyl, n-butyl, tert-butyl, isobutyl , 2,2-dimethylpropyl, pentyl, octyl, and decyl. The terms “alkenyl” and “alkynyl” mean (C3-Cyo) alkenyl and (Cs-
Cao) alkynyl groups such as, for example, 2-propenyl, 2-butenyl, 3-butenyl, 2-methyl- 2-propenyl, and 2-propynyl. The term “cycloalkylallxyl” means a (C-Cs) alkyl group substituted with a (C3-C7) cycloalkyl group such as, for example cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, and cyclopentylethyl. The term “haloalkyl” means an alkyl radical wherein one or more of the hydrogen atoms have been replaced by a halogen atom. The term “halogen” means one or more of fluorine, chlorine, bromine, and iodine.
The practice of the present invention involves the use of onc or more cyclopropenes. As used herein, "cyclopropene” mearrs any compound with the formula
CH ve
CHa where R is hydrogen or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl, or naphthyl group ; wherein the substituents, when present, are independently halogen, alkoxy, or substituted or unsubstituted phenoxy.
As used herein, when the compound of the above structure when R is a hydrogen is meant, the phrase "unsubstituted cyclopropene” will be used.
In some embodiments, R has no double bond. Independently, in some embodiments, R has no triple bond. Independently, in some embodiments, there is no halogen atom substituent on R. Independently, in some embodiments, R has no substituents that are ionic. Independently, in some embodiments, R is not capable of generating oxygen compounds.
Co oo ) 2005 "nsw . | SVEN
In some embodiments of the invention, R is (C-Cyp) alkyl. In some embodiments, R is (C,-Cs) alkyl, or (C,-C4) alkyl, or methyl. When R is methyl, the cyclopropene is known herein as "1-MCP."
The cyclopropenes applicable to this invention are known materials, which may be prepared by any method. Some suitable methods of prepa ration of cyclopropenes are the processes disclosed in U. S. Patents No. 5,5 13,988 and 6,017,849.
The amount of cyclopropene in compositions of the present invention may vary widely, depending on the type of composition and the intended method of use.
In some embodiments, the amount of cyclopropene, based on the t otal weight of the composition, is 4% by weight or less; or 1% by weight or less; or 0.5% by weight or less; or 0.05% by weight or less. Independently, in some embodirments, the amount of cyclopropene, based on the total weight of the composition, is 0 .000001% by weight or more; or 0.00001% by weight or more; or 0.0001% by weight or more; or 0.001% by weight or more.
In compositions of the present invention that include water, the amount of cyclopropene may be characterized as parts per million (i.e., parts by weight of cyclopropene per 1,000,000 parts by weight of water, "ppm") or as parts per billion (i.c., parts by weight of cyclopropene per 1,000,000,000 parts by weight of water, "ppb"). In some embodiments, the amount of cyclopropene is 1 ppb or more; or 10 ppb or more; or 100 ppb or more. Independently, in some embodixnents, the amount of cyclopropene is 10,000 ppm or less; or 1,000 ppm or less.
In some embodiments, the practice of the present invention involves the use of one or more metal-complcxing agents. A metal-complexing agent &s a compound that contains one or more electron-donor atoms capable of forming coordinate bonds with a metal atoms. Some metal-complexing agents are chelating agents . As used herein, a "chelating agent” is a compound that contains two or more electro n-donor atoms that are capable of forming coordinate bonds with a metal atom, and a single molecule of the chelating agent is capable of forming two or more coordinate bonds with a single metal atom. Suitable chelating agents include, for example, organic and inorganic chelating agents. Among the suitable inorganic chelating agents are, for example, phosphates such as, for example, tetrasodium pyrophosphate, sodium : tripolyphos phate, and hexametaphosphoric acid. Among the suitable organic chelating agents are those with macrocyclic structures and non-macr-ocyclic
~~ a a
Coe 2005/0505 5 structure s. Among the suitable macrocyclic organic chelating agents ar-e, for example, porphine. compounds, cyclic polyethers (also called crown ethers), and mnacrocyclic compourads with both nitrogen and oxygen atoms.
S ome suitable organic chelating agents that have non-macrocyckEic structures
S are, for example, aminocarboxylic acids, 1,3-diketones, hydroxycarbox wylic acids, polyamimes, aminoalcohols, aromatic heterocyclic bases, phenol, amino-phenols, oximes, Shiff bases, sulfur compounds, and mixtures thereof. In some embodiments, the chelating agent includes one or more aminocarboxylic acids, one or more hydroxyc arboxylic acids, one or more oximes, or a mixture thereof. Somme suitable aminocarboxylic acids include, for example, ethylenediaminetetraacetic acid (EDTA), hydroxyethylethylenediaminetriacetic acid (HEDTA), nitrilotriacetic acid (NTA), N- dihydrox sethylglycine (2-HxG), ethylenebis(hydroxyphenylglycine) (EEHPG), and mixtures hereof. Some suitable hydroxycarboxylic acids include, for example, tartaric acid, citric acid, gluconic acid, 5-sulfoslicylic acid, and mixtures thereof. :
Some suitable oximes include, for example, dimethylglyoxime, salicylal doxime, and mixtures thereof. In some embodiments, EDTA is used.
Sosme additional suitable chelating agents are polymeric. Some suitable polymeric chelating agents include, for example, polyethyleneimines, polymethaicryloylacetones, poly(acrylic acid), and poly(methacrylic acid ). Poly(acryEic acid) is used in some embodiments.
So me suitable metal-complexing agents that are not chelating agents are, for cxample, alkaline carbonates, such as, for example, sodium carbonate.
Metal-complexing agents may be present in neutral form or in the form of one or more salts. Mixtures of suitable metal-complexing agents are also suitable.
Also contemplated are embodiments of the present invention in w~hich no metal-com_plexing agent is used.
Sorne embodiments of the present invention do not contain water
In some embodiments, the composition of the present invention docs contain water; in some of such embodiments, the water contains one Or more metal ions, such as, for exarnple, iron ions, copper ions, other metal ions, or mixtures thereof. In some embodimemts, the water contains 0.1 ppm or more of one or more metal icons.
Among embodiments that use one or more metal-complexing agers, the amount of ametal-complexing agent used in the present invention also may” vary widely. In some embodiments, the amount of metal-complexing agent wi ll be
(a adjustexd to be sufficient to complex the amount of metal ior that is present or expect ed to be present in those embodiments. For example, in some embodiments in which the composition of the present invention includes water, if a relatively efficient chelati ng agent is used (i.c., a chelating agent that will form a complex with all or
S nearly all the metal ions in the water), the ratio of moles of chelating agent to moles of metal ion will be 0.1 or greater; or 0.2 or greater; or 0.5 or greater; or 0.8 or greater.
Among such embodiments that use a relatively efficient cheE ating agent, the ratio of moles of chelating agent to moles of metal ion will be 2 or less; or 1.5 or less; or 1.1 or less.
Independently, in some embodiments, the amount of metal-complexing agent is, base=d on the total weight of the composition, 25% by wei ght or less; or 10% by weight or less; or 1% by weight or less. Independently, in some embodiments, the amount of metal-complexing agent is, based on the total weight of the composition, 0.00001 % or more; or 0.0001% or more; or 0.01% or more.
Independently, in some embodiments in which the co mposition of the present invention includes water, the amount of metal-complexing agzent can usefully be determi ned by the molar concentration of metal-complexing gent in the water. In some ernbodiments, the concentration of metal-complexing a gent is 0.00001 mM (i.e, milli-M olar) or greater; or 0.0001 mM or greater; or 0.001 rmM or greater; or 0.01 mM or greater; or 0.1 mM or greater. Independently, in som.e embodiments in which the com position of the present invention includes water, the concentration of metal- complexing agent is 100 mM or less; or 10 mM or less; or I mM or less. “The composition of the present invention includes at | east one molecular encapsu lating agent. Useful molecular encapsulating agents include, for example, organic and inorganic molecular encapsulating agents. Suitable organic molecular encapsu lating agents include, for example, substituted cyclodextrins, unsubstituted cyclodextrins, and crown ethers. Suitable inorganic molecular encapsulating agents include, for example, zeolites. Mixtures of suitable molecular encapsulating agents are also suitable. In some embodiments of the invention, the encapsulating agent is a-cyclodextrin ("a-CD"), B-cyclodextrin, y-cyclodextrin, or a mixture thereof. In another embodiment of the invention, particularly when the cy/clopropene is 1- methylcyclopropene, the encapsulating agent is a-cyclodextrir. The preferred encapsul ating agent will vary depending upon the size of the RR group. However, as

Claims (10)

  1. « Ln 16 20057 050z - REY We claim:
    I. A composition comprising (a) one or more molecular encapsulation agents within each of which is encapsulated one or more cyclopropenes of the formula CH — , wherein said R is hydrogen or a substituted or unsubstitut ed alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl, or naphthyl group; wherein the substituents, when present, are independently halogen, alkoxy, or substituted or unsubstituted phenoxy; and (b) ome or more adjuvants selected from the group consisting of surfactants, alcohols, hydrocarbon oils, and mixtures thereof.
  2. 2. The co mposition of claim 1, wherein said R is (Ci-Cyalkyl.
  3. 3. The co mposition of claim {, wherein said one or more molectalar cncapsulation agents comprises a cyclodextrin or a mixture of cyclodextrins .
  4. 4. The composition of claim 1, wherein said one or more adjuvamts comprises at least ome alkyl alcohol.
  5. 5. The composition of claim 1, wherein said one or more adjuvamts comprises at least o ne hydrocarbon oil.
  6. 6. The composition of claim 1, wherein said one or more adjuvants comprises at least o ne surfactant.
  7. 7. The composition of claim 6, wherein said one or more adjuvants further comprises at least one alkyl alcohol; or at least one hydrocarbon oil; or both of at leas t one alkyl alcohol and at least one hydrocarbon oil.
  8. 8. The composition of claim 1, wherein said composition further comprises water.
  9. 9. The composition of claim 1, wherein said composition furthe T comprises one or more mnetal-complexing agents.
  10. 10. A method comprising the step of contacting the composition of claim 1 with one or mo re plants or plant parts. Dated this 21st day of July 2005 Aad BOWMAN GILFILLAN JOHN & KERNICK FOR THE APPLICANT
ZA200505855A 2005-07-21 2005-07-21 Compositions with cyclopropenes and adjuvants ZA200505855B (en)

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Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ZA200505855A ZA200505855B (en) 2005-07-21 2005-07-21 Compositions with cyclopropenes and adjuvants

Publications (1)

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ZA200505855B true ZA200505855B (en) 2006-04-26

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