Method of protecting plants from cold injury

Plant husbandry – Frost preventing

Reexamination Certificate

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C047SDIG001, C047S05810R

Reexamination Certificate

active

06367193

ABSTRACT:

FIELD OF THE INVENTION
The present invention concerns methods of protecting plants such as citrus trees, peanuts, peaches and strawberries from cold injury, such as damage by frost or freezing.
BACKGROUND OF THE INVENTION
Frost, freeze and other cold damage to plants is a serious agricultural problem. Plants that flower early in the growing season are susceptible to late winter or early spring frost, and plants that are harvested late in the growing season are susceptible to late fall or early winter frost. It has been estimated that approximately 1.5 billion dollars worth of agricultural products are annually lost to freezing temperatures in the United States alone (see U.S. Pat. No. 5,276,006). Among other things, frost injury causes significant damage to citrus, strawberry, peanut and peach crops. Accordingly, there is a need for new ways to combat frost injury to plants.
A variety of approaches to protecting plants from frost and freezing have been suggested. For example, U.S. Pat. No. 5,276,006 to Shin et al. (assigned to Great Lakes Chemical Corp.) describes an aqueous plant cryoprotectant containing a tetrahydrofurfuiryl alcohol or tetrahydrofurfuryl amine. U.S. Pat. No. 4,207,091 to Fischer (assigned to Ciba-Geigy Corp.), describes a method of combating frost damage in plants by treating the plants prior to frost with certain hydroxamic acid derivatives. U.S. Pat. No. 4,432,160 to Lindow (assigned to the University of California) suggests inhibiting frost damage by treating plants with antagonistic ice nucleation deficient bacteria to inhibit colonization of the plant by ice nucleation capable bacteria. U.S. Pat. No. 5,133,891 to Barr et al. (assigned to Rhone Poulenc AG Co.), describes a method for combating frost damage by applying aluminum tris-[O-ethyl phosphonate], or fosetyl-Al, apparently to kill ice nucleating bacteria. Nevertheless, there remains a need for new ways to treat plants to reduce damage from frost and freezing.
SUMMARY OF THE INVENTION
The present invention provides a method of reducing cold injury or damage to a plant, including individual plants and plants existing as a crop of like plants. The method comprises applying a pyridylaniline active agent to the plant in an amount effective to reduce cold injury to the plant. A particularly preferred active agent is fluazinam. The methods may be carried out to reduce any type of cold injury, including frost injury and freezing injury.
The present invention is explained in greater detail below. This explanation is not intended to be an exhaustive catalog of all the different embodiments and manners in which the present invention may be carried out, but is intended to be illustrative of particular embodiments of the invention. Numerous variations will be apparent to those skilled in the art.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present invention may be used to protect any type of plant from frost or freeze injury, including trees, shrubs, herbaceous plants, etc. Plants treated by the invention are typically frost or cold sensitive plants, in that they are susceptible to frost, freezing or cold damage or injury in economically or aesthetically significant amounts. Specific plants that may be protected by the method of the invention include, but not limited to, peanuts, peaches, strawberries, citrus trees (lemon, lime, orange, etc.), cherries, apples, etc, as well as vegetable crops (e.g., beans, peas), as well as ornamental plants. The term “plant” as used herein includes the complete plant or a portion thereof, such as a flowers, fruits, leaves, stems vegetables, roots, tubers, etc. “Alkyl” as used herein refers to an alkyl group, which may be linear or branched, and saturated or unsaturated. Alkyl groups, as used herein, are preferably saturated.
“Lower alkyl” as used herein refers to an an alkyl group which contains 1 to 4 carbon atoms.
“Alkoxy” as used herein refers to a group —O—R, wherein R is alkyl.
“Lower alkoxy” as used herein refers to an alkoxy group which contains 1 to 4 carbon atoms.
“Halogen” as used herein refers to any halogen group, such as fluoro, chloro, bromo, or iodo, preferably chloro.
“Cold injury” means any type of injury to a plant or plant part caused by a decrease in temperature that results in an economic or aesthetic damage to that plant. Such injury may be by frost injury, freezing injury, or a decrease in temperature below that tolerated by the plant even if the temperature does not decrease below freezing (32° F.; 0° C.) (e.g., as seen in orchids).
“Frost injury” as used herein refers to any type of damage to a plant or plant part that results from the deposition of frost on the surface thereof, whether that frost is natural frost or frozen water or water vapor deposited upon the plant or plant part by artificial means. Such damage includes, but is not limited to, reduced yield, blemishes or other damage that decreases the quality or value of the plant or plant part without reducing yield, etc.
“Freeze injury” as used herein refers to any type of damage to a plant or plant part that results from the formation of ice crystals in at least some cells of that plant, whether or not the ice crystals are formed by natural means due to decreased ambient temperature or artificial cooling or refrigeration. Again, such damage includes, but is not limited to, reduced yield, blemishes or other damage that decrease the quality or value of the plant or plant part without reducing yield, etc.
Active compounds that may be used to carry out the present invention are, in general, pyridylanilines of Formula I:
wherein X is a trifluoromethyl group, a halogen atom, a lower alkyl group or a lower alkoxy group; n is an integer of 0 to 4; R is a hydrogen atom or an acetyl group; Y is a hydrogen atom, a halogen atom, a lower alkoxy group, a lower alkylthio group, a hydroxy group, an azido group or a phenoxy group of which the phenyl ring may be substituted by a hydroxy group; and Z
1
, Z
2
, and Z
3
are independently a trifluoromethyl group or a nitro group; provided that at least one of X is a trifluoromethyl group or a lower alkyl group when n is an integer of 3 or 4.
Preferred compounds of Formula I are those wherein X is a trifluoromethyl group, a halogen atom, a lower alkyl group or a lower alkoxy group; n is an integer of 1 to 4; R is a hydrogen atom or an acetyl group; Y is a hydrogen atom, a halogen atom, a lower alkoxy group, a lower alkylthio group or a hydroxy group; Z
1
, Z
2
, and Z
3
are a trifluoromethyl group or a nitro group, with the proviso that at least one X is trifluoromethyl and with the proviso that when the X substitution pattern is 3-chloro-5-trifluoromethyl, Y in addition optionally is azido or 2, 3, or 4-hydroxyphenoxy.
Compounds of Formula I are known, and can be made as described in U.S. Pat. No. 4,331,670 to Nishiyama et al. It is specifically intended that all United States patent references cited herein be incorporated herein by reference.
A particularly preferred active compound for carrying out the present invention is fluazinam (or 3-chloro-N-[3-chloro-2,6-dinitro-4-trifluoromethyl)phenyl]-5-trifluoromethyl-2-pyridinamine) (See Merck Index No. 4153 (12th Ed. 1996)), which has the structure of Formula II:
Compounds of Formula II may be made in the same manner as compounds of Formula I above.
Active compounds used herein may be formulated together with agricultural adjuvants and/or carriers into various forms such as dusts, granules, water dispersible granules, wettable powders, emulsifiable concentrations, suspension concentrates, soluble concentrates, water soluble powders, flowables, aerosols or pastes, ultra low-volume formulations, etc. When such formulations are to be actually used, they may be used as is or after being diluted with suitable diluents or carriers such as water.
Such formulations may be composed of 0.01 or 0.1 to 90 or 99 parts by weight of active ingredient, 0.0 or 0.1 to 99.9 parts by weight of agricultural adjuvants, and 0.0 or 0.1 to 99.9 parts by weight of agricultural carrier.
Suitable adjuvants in

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