Plant protecting and regulating compositions – Compositions for preservation or maintenance of cut flowers
Reexamination Certificate
1999-11-23
2001-02-27
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Compositions for preservation or maintenance of cut flowers
C504S357000
Reexamination Certificate
active
06194350
ABSTRACT:
FIELD OF THE INVENTION
The present invention generally relates to methods of blocking ethylene responses in plants and plant materials, and particularly relates to methods of inhibiting various ethylene responses including plant maturation and degradation by applying cyclopropene derivatives and compositions thereof to plants.
BACKGROUND OF THE INVENTION
Ethylene is known to mediate a variety of growth phenomena in plants. See generally Fritz et al. U.S. Pat. No. 3,879,188. This activity is understood to be achieved through a specific ethylene receptor in plants. Many compounds other than ethylene interact with this receptor: some mimic the action of ethylene; others prevent ethylene from binding and thereby counteract its action.
Many compounds that block the action of ethylene do so by binding to the ethylene binding site. Unfortunately, they often diffuse from the binding site over a period of several hours. See E. Sisler and C. Wood, Plant Growth Reg. 7, 181-191 (1988). These compounds may be used to counteract ethylene action. A problem with such compounds, however, is that exposure must be continuous if the effect is to last for more than a few hours.
Photoaffinity labeling has been used in biological studies to label binding sites in a permanent manner: usually by generating a carbene or nitrene intermediate. Such intermediates are very reactive and react rapidly and indiscriminately with many things. A compound already bound, however, would react mostly with the binding site. In a preliminary study, it was shown that cyclopentadiene was an effective blocking agent for ethylene binding. See E. Sisler et al., Plant Growth Reg. 9, 157-164 (1990). Methods of combating the ethylene response in plants with diazocyclopentadiene and derivatives thereof are disclosed in U.S. Pat. No. 5,100,462 to Sisler et al. U.S. Pat. No. 5,518,988 to Sisler et al. describes the use of cyclopropenes having a C
1
to C
4
alkyl group to block the action of ethylene.
Notwithstanding these efforts, there remains a need in the art for improved plant maturation and degradation regulation.
SUMMARY OF THE INVENTION
Methods of inhibiting an ethylene response in a plant are disclosed herein. According to the present invention, one such method comprises applying to the plant an effective ethylene response-inhibiting amount of a cyclopropene derivative or a composition thereof described further in detail herein. Long-chain cyclopropene derivatives are particularly preferred as described below.
Another aspect of the present invention is a method of blocking ethylene receptors in plants by applying to the plants an effective ethylene receptor-blocking amount of a cyclopropene derivative or a composition thereof.
Also disclosed is a method of inhibiting abscission in a plant, comprising applying to the plant an effective abscission-inhibiting amount of a cyclopropene derivative or a composition thereof.
Also disclosed is a method of prolonging the life of a cut flower, comprising applying to the cut flower an effective life-prolonging amount of a cyclopropene rivative or a composition thereof.
The methods described herein may be carried out in a number of suitable manner, such as by contacting the plant with a cyclopropene derivative or a composition thereof, whether in solid, liquid, or gaseous form, or by introducing the plant or cut flower into an atmosphere infused with the cyclopropene derivative or a composition thereof. These and other suitable methods of application are discussed in detail below.
Also disclosed is the use of a cyclopropene derivative as described herein for the preparation of an agricultural composition for carrying out any of the methods described above.
DETAILED DESCRIPTION OF THE INVENTION
Cyclopropene derivatives which may be used to carry out the present invention are defined by Formula I:
wherein:
n is a number from 1 to 4. Preferably n is 1 or 2, and most preferably n is 1.
R is a saturated or unsaturated, linear or branched-chain, unsubstituted or substituted, C
6
to C
20
alkyl, alkenyl, or alkynyl.
The terms “alkyl”, “alkenyl”, and “alkynyl”, as used herein, refer to linear or branched alkyl, alkenyl or alkynyl substituents. The terms should be interpreted broadly and may include compounds in which one or more of the carbons in the chain is replaced by heteroatoms such as oxygen or nitrogen, ester groups, nitrites and their salts, acids and their salts and esters, or where such chains include halogen, amino, alkoxy, carboxy, alkoxycarbonyl, or hydroxy substituents. Examples include, but are not limited to, hexyl, heptyl, octyl, nonyl, and decyl. Alkyl groups of the present invention are preferably linear and saturated.
Cyclopropene derivatives which may be used to carry out the present invention may be prepared by various methods known to those skilled in the art. For example, 1-substituted cyclopropenes can be prepared from 1,1,3-tribromo substituted cyclopropanes as described by Baird et al. in
Preparation and Lithiation of
1-
Halogenocyclopropenes,
J. CHEM. SOC. PERKIN TRANS. I 1845-53 (1986). Additionally, 3,3-Substituted clyclopropenes can be prepared using methods described by N. I. Yakushkina and I. G. Bolesov in
Dehydrohalogenation of Monohalogenocyclopropanes as a Method for the Synthesis of Sterically Screened Cyclopropenes,
RUSSIAN J. OF ORGANIC CHEM. 15:853-59 (1979).
Agricultural compositions comprising the compounds defined by Formula (I) described above are also encompassed by the invention. Preferably the compositions comprise between 0.005 to 99% by weight of the active compounds of the present invention may be formed. These compositions may optionally include various additives typically found in agricultural compositions including, but not limited to, carriers, adjuvants, wetting agents and the like.
Numerous organic solvents may be used as carriers for the active compounds of the present invention, e.g., hydrocarbons such as hexane, benzene, toluene, xylene, kerosene, diesel oil, fuel oil and petroleum naphtha, ketones such as acetone, methyl ethyl ketone and cyclohexanone, chlorinated hydrocarbons such as carbon tetrachloride, esters such as ethyl acetate, amyl acetate and butyl acetate, ethers, e.g., ethylene glycol monomethyl ether and diethylene glycol monomethyl ether, alcohols, e.g., ethanol, methanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol, butyl carbitol acetate and glycerine.
Mixtures of water and organic solvents, either as solutions or emulsions, can also be employed as inert carriers for the active compounds.
The active compounds of the present invention may also include adjuvants or carriers such as talc, pyrophyllite, synthetic fine silica, attapulgus clay (attaclay), kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite, fuller's earth, cottonseed hulls, wheat flour, soybean flour pumice, tripoli, wood flour, walnut shell flour, redwood flour and lignin.
It may be desirable to incorporate a wetting agent in the compositions of the present invention. Such wetting agents may be employed in both the solid and liquid compositions. The wetting agent can be anionic, cationic or nonionic in character.
Typical classes of wetting agents include alkyl sulfonate salts, alkylaryl sulfonate salts, alkyl sulfate salts, alkylamide sulfonate salts, alkylaryl polyether alcohols, fatty acid esters of polyhydric alcohols and the alkylene oxide addition products of such esters, and addition products of long chain mercaptans and alkylene oxides. Typical examples of such wetting agents include the sodium alkylbenzene sulfonates having 10 to 18 carbon atoms in the alkyl group, alkylphenol ethylene oxide condensation products, e.g., p-isooctylphenol condensed with 10 ethylene oxide units, soaps, e.g., sodium stearate and potassium oleate, sodium salt of propylnaphthalene sulfonic acid (di-2-ethylhexyl), ester of sodium sulfosuccinic acid, sodium lauryl sulfate, sodium stearate and potassium oleate, sodium salt of the sulfonated monoglyceride of coconut fatty acids, sorbitan, sesquioleate, lauryl trimethyl am
Clardy S. Mark
Myers Bigel & Sibley & Sajovec
North Carolina State University
LandOfFree
Methods of blocking ethylene response in plants using... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Methods of blocking ethylene response in plants using..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Methods of blocking ethylene response in plants using... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2585707