Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2002-02-26
2003-04-15
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C206S423000, C504S207000, C504S326000, C504S349000, C504S351000, C504S357000, C047S065700, C047S065800, C047S066700, C047S087000
Reexamination Certificate
active
06548448
ABSTRACT:
The present invention relates to new delivery systems for cyclopropenes in which the cyclopropene, either free or encapsulated within a molecular encapsulation agent, is incorporated into packaging materials for agricultural produce and ornamental plants.
It is well known that ethylene can cause the premature death of plants or plant parts including, for example, flowers, leaves, fruits, and vegetables through binding with certain receptors in the plant. Ethylene is known to promote leaf yellowing and stunted growth as well as premature fruit, flower, and leaf drop. In addition, ethylene is also known to induce or accelerate the ripening of harvested fruits and vegetables. Because of these ethylene-induced problems, very active and intense research presently concerns the investigation of ways to prevent or reduce the deleterious effects of ethylene on plants. U.S. Pat. No. 5,518,988 discloses the use of cyclopropene and its derivatives, including methylcyclopropene, as effective blocking agents for ethylene binding. However, a major problem with these compounds is that they are typically unstable gases which present explosive hazards when compressed. U.S. Pat. No. 6,017,849 discloses a method of incorporating these gaseous compounds into a molecular encapsulation agent complex in order to stabilize their reactivity and thereby provide a convenient and safe means of storing, transporting and applying or delivering the active compounds to plants as a way to alleviate these problems. For the most active cyclopropene derivative disclosed in U.S. Pat. No. 5,518,988, 1-methylcyclopropene (“1-MCP”), the preferred molecular encapsulation agent is a cyclodextrin, with &agr;-cyclodextrin being the most preferred. The application or delivery of these active compounds to plants is accomplished by simply adding water to the molecular encapsulation agent complex. The complex is prepared according to the methods disclosed in U.S. Pat. No. 6,017,849 which provides the material in the form of a powder.
The powdered complex is usually added to water to release the 1-MCP into the atmosphere where plants or plant parts to be treated are stored, that is, a treatment container or room. Typical treatment concentrations are 0.1 to 1.0 ppm (vol/vol) in the atmosphere surrounding the plant or plant parts. In order to accomplish this release large amounts of water are required, at least ten times and preferably twenty times the weight of the 1-MCP/&agr;-cyclodextrin complex. It would advantageous to have a delivery system in which 1-MCP is incorporated into packaging materials which often surround plants or plant parts and in which 1-MCP is released without the need for adding water.
We have surprisingly found that the low concentrations of cyclopropenes needed to treat fruits, vegetables, and flowers (“produce”) can be released from packaging materials which incorporate the cyclopropene. The cyclopropene can be incorporated directly into many types of packaging materials or it can first be encapsulated into a molecular encapsulation agent which is then subsequently incorporated into packaging materials. We have found that moisture from humid air surrounding produce is often sufficient to release the amounts of cyclopropene required for effective treatment of the produce. In one form of the invention the powdered complex is prepared as part of the film or container. The powder can be compounded within, or laminated between, different thermoplastic packaging plastics such as polyethylene, ethyl vinylacetate, polyvinyl alcohol or with rigid plastics such as polystyrene, polycarbonate, and polymethyl methacrylate. In addition, it can be incorporated into various waxes and coated papers and cardboard or it can be incorporated into an adhesive component of packaging materials.
The present invention is, therefore, a composition comprising
a) a compound of the formula:
wherein:
1) each R
1
, R
2
, R
3
, and R
4
is independently a group of the formula:
—(L)
n
—Z
wherein:
i) n is an integer from 0 to 12;
ii) each L is independently selected from a member of the group D, E or J wherein:
D is of the formula:
E is of the formula:
J is of the formula:
wherein:
A) each X and Y is independently a group of the formula:
—(L)
m
—Z;
and
B) m is an integer from 0 to 8; and
C) no more than two E groups are adjacent to each other and no J groups are adjacent to each other;
iii) each Z is independently selected from:
A) hydrogen, halo, cyano, nitro, nitroso, azido, chlorate, bromate, iodate, isocyanato, isocyanido, isothiocyanato, pentafluorothio, or
B) a group G, wherein G is an unsubstituted or substituted; unsaturated, partially saturated, or saturated; monocyclic, bicyclic, tricyclic, or fused; carbocyclic or heterocyclic ring system wherein;
1) when the ring system contains a 3 or 4 membered heterocyclic ring, the heterocyclic ring contains 1 heteroatom;
2) when the ring system contains a 5, or more, membered heterocyclic ring or a polycyclic heterocyclic ring, the heterocyclic or polycyclic heterocyclic ring contains from 1 to 4 heteroatoms;
3) each heteroatom is independently selected from N, O, and S;
4) the number of substituents is from 0 to 5 and each substituent is independently selected from X;
2) the total number of non-hydrogen atoms in each compound is 50 or less; and
its enantiomers, stereoisomers, salts, and mixtures thereof;
b) a packaging material.
For the purposes of this invention, in the structural representations of the various L groups each open bond indicates a bond to another L group, a Z group, or the cyclopropene moiety. For example, the structural representation
indicates an oxygen atom with bonds to two other atoms; it does not represent a dimethyl ether moiety.
Another embodiment of this invention is a method to inhibit an ethylene response in a plant comprising the step of enclosing the plant in packaging which incorporates the composition of this invention.
A further embodiment is a method to prolong the life of a plant comprising the step of enclosing the plant in packaging which incorporates the composition of this invention.
Another embodiment of this invention is a method to deliver a cyclopropene compound to a plant to inhibit an ethylene response in the plant comprising the step of enclosing the plant in the composition of this invention.
As used herein, the term “halo” means fluorine, chlorine, bromine, and iodine.
Preferably, the number of non-hydrogen atoms in each compound is less than 25. More preferably, the number of non-hydrogen atoms in each compound is less than 20. Even more preferably, the number of non-hydrogen atoms in each compound is less than 13. Most preferably, the number of non-hydrogen atoms in the compound is less than 7.
Preferably, two of R
1
, R
2
, R
3
, and R
4
are hydrogen. More preferably, R
1
and R
2
are hydrogen or R
3
and R
4
are hydrogen. Even more preferably, R
2
, R
3
, and R
4
are hydrogen or R
1
, R
2
, and R
4
are hydrogen. Most preferably, R
2
, R
3
, and R
4
are hydrogen.
Preferably, R
1
is (C
1
-C
10
) alkyl and R
2
, R
3
, and R
4
are hydrogen. More preferably, R
1
is (C
1
-C
8
) alkyl and R
2
, R
3
, and R
4
are hydrogen. Even more preferably R
1
is (C
1
-C
4
) alkyl and R
2
, R
3
, and R
4
are hydrogen. Most preferably, R
1
is methyl and R
2
, R
3
, and R
4
are hydrogen.
Typical R
1
, R
2
, R
3
, and R
4
groups include, for example: alkenyl, alkyl, alkynyl, acetylaminoalkenyl, acetylaminoalkyl, acetylaminoalkynyl, alkenoxy, alkoxy, alkynoxy, alkoxyalkoxyalkyl, alkoxyalkenyl, alkoxyalkyl, alkoxyalkynyl, alkoxycarbonylalkenyl, alkoxycarbonylalkyl, alkoxycarbonylalkynyl, alkylcarbonyl, alkylcarbonyloxyalkyl, alkyl(alkoxyimino)alkyl, carboxyalkenyl, carboxyalkyl, carboxyalkynyl, dialkylamino, haloalkoxyalkenyl, haloalkoxyalkyl, haloalkoxyalkynyl, haloalkenyl, haloalkyl, haloalkynyl, hydroxyalkenyl, hydroxyalkyl, hydroxyalkynyl, trialkylsilylalkenyl, trialkylsilylalkyl, trialkylsilylalkynyl, dialkylphosphonato, dialkylphosphato, dialkylthiophosphato, dialkylaminoalkyl, alkylsulfonylalkyl, alkylthlio
Clardy S. Mark
Rogerson Thomas D.
Rohm and Haas Company
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