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
  • 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
  • A01N25/02—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 containing liquids as carriers, diluents or solvents
  • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
• • 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
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids

Definitions

• the present invention is related generally to the field of agri ⁇ culture and specifically to compositions and use of plant growth regulators.
• Agriculture workers actively seek ways to improve the economic output of commercial crops. For example, in cotton crops, workers seek to improve such growth factors as an increased in boll set, increased in floral initiation, decreased floral abscission, de- creased boll abscission, and enhanced root growth. Workers also seek to a increase plant in tolerance to environmental stress.
• Formulations containing plant growth regulators have been developed to improve the economic yield of agricultural plants.
• Plant growth retardants and inhibitors of ethylene biosynthesis or action are two types of PGRs.
• Some plant growth retardants have been shown to inhibit gibberellin biosynthesis resulting in the reduction of shoot height in small grains and cotton. This reduction in shoot height has a strong economic benefit since it provides for less lodging in small grains and reduction of exces ⁇ sive vegetative growth. It also provides more uniform ripening in cotton.
• the first group encompasses compounds with quaternary ammonium, phosphonium or sulphonium moieties.
• mepiquat chloride described in U.S. Patent No. 3,905,798 and incorporated herein by .reference.
• Mepiquat chloride increases cotton yields, boll load, lint yield and seed yield.
• Mepiquat chloride is also known to reduce vegetative growth, plant height and boll rot. Mepiquat chloride also induces uniform ripeness if the plants are treated early during their de ⁇ velopment.
• Chloromequat chloride is also a representative compound of this group.
• the second group of plant growth retardants encompasses compounds with a nitrogen containing heterocycle such as flurprimidol, pa ⁇ clobutrazol, uniconazole and ancymidol.
• the third group encompasses acylcylcohexanediones (such as tri- nexapac-ethyl and prohexadione-Ca) and daminozide.
• ethylene is involved in plant senescence and plant stress reactions. Ethylene is also involved in leaf, flower, and fruit abscission.
• agents that inhibit or regu ⁇ late the production of ethylene or control its action in plants have been developed in an effort to improve the yield of agri ⁇ cultural crops.
• Inhibitors of ethylene biosynthesis include sub ⁇ stituted oxime-ethers as described in U.S. Patent No. 4,744,811, incorporated herein by reference. These compounds are also de ⁇ scribed in PCT Application WO 95-02211, incorporated herein by reference, as being soil amendment compositions that increase the assimilation of nitrogen by higher plants.
• AVG ami- noethoxyvinylglycine
• AOA aminooxyacetic acid
• MVG methoxyvinyl glycine
• Silver ions e. g. silver thiosulfate
• 2, 5-norbornadiene inhibit ethylene ac ⁇ tion.
• Plant growth regulators have also been used to protect crops from the effects of environmental stress. Gianfagna, T.J. et al. "Mode of Action and Use of Growth Retardants in Reducing the Effects of Environmental Stress on Horticultural Crops: Karssen CN. et al . (eds.) Progress in Plant Growth Regulation, pp. 778-87 (1992). For example, researchers found that if ethephon was applied at a low rate (0.08 mM) it significantly delayed bloom in peach and reduced side effects. researchers also found that ethephon in ⁇ creased the yields and hardiness of several horticultural plants.
• PGRs have been developed as a means to improve agri- cultural crop yields, certain obstacles make the actual use of the PGR prohibitive. For example, many of the compounds display phytotoxicity. Other compounds are difficult to synthesize.
• PCT Application WO 93/07747 describes an improvement in a plant growth factor by applying aminoethoxyvinylglycine CAVG", an inhibitor of ethylene biosynthesis, to cotton plants. As the rate of AVG treatment increased, so did the improvement. (WO 93/07747, Exam- pies 2-4) . Assuming that a spray volume of 500 1/ha was used, the rates of application described in WO 93/07747 would be approxi ⁇ mately 62.5 to 500 g ai/ha. The maximum rate response occurs at the highest rates.
• High rate applications may result in a significant waste of mate ⁇ rial and may result in the discharge of the PGRs into the sur ⁇ rounding environment. Also, although many of these compounds may induce a beneficial growth habit, they do not provide consistent improvement in plant growth factors. Other compounds may lose their effectiveness or cause a reduction in yield when applied to species which are under some form of environmental stress.
• Polyvinyl alcohol has been described as: a protective colloid in an emulsion formed by the dispersion of an organic solution containing a plant growth regulator, U.S. Pat.
• U.S. Pat No. 4,997,642 discloses stable oil-in-water emulsions containing a PVA, a surfactant, a salt, and a water-insoluble oily compound, such as a plant growth regulator, wherein the compound is dispersed as a particle having an average size of less than one micron.
• a plant growth regulator formulation comprising a plant growth regulator dispersed in polycinyl alcohol (“PVA”) particles having a mean diameter greater than 1 micron.
• the present invention also includes an emulsion containing an aqueous dispersion of PVA en ⁇ capsulated plant growth regulator particles wherein said par ⁇ ticles have a mean diameter greater than 1 micron.
• present invention is directed to a particle comprising a plant growth regulator contained in a polyvinyl alcohol matrix.
• composition in provided comprising a plant growth regulator contained in a polyvinyl alcohol matrix as defined before and, as a second com ⁇ ponent, a plant growth retardant.
• the above formulations are useful in methods of improving a plant growth factor in a plant comprising administering to said plant a plant growth regulator formulation comprising the formulations of the present invention, i.e., a plant growth regulator dispersed in polyvinyl alcohol ("PVS") particles having a mean diameter greater than 1 micron.
• the methods also include applying an emul ⁇ sion containing an aqueous dispersion of PVA encapsulated plant growth regulator particles wherein said particles have a mean di ⁇ ameter greater than 1 micron.
• An improvement in a plant growth factor is defined as an agro ⁇ nomic improvement of plant growth such as increased floral ⁇ square) initation, increased flower retention, increased root growth, decreased internode length, darker green pigmentation, increased germination rate, increased tolerance to low and high temperatures, and increased crop yield. That is, a favorable al ⁇ ternation of the physiology or growth of plants or an increase or decrease in plant growth which leads to an economic or agronomic benefit. Improvement in growth factors that result from the in ⁇ hibition of ethylene production is preferred.
• the emulsions of the present invention are particularly suitable for formulations containing pVA encapsulated inhibitors of ethylene biosynthesis or action, preferably substituted oxime- ethers having the formula:
• R 1 and R 2 independently of one another are C ⁇ -C 6 -akyl, n is 2 or 3 and R 3 is hydrogen or Ci-C ⁇ alkyl.
• AOA aminooxyacetic
• H 2 N-0 Preferred oxime-ethers for use in the method include the follow ⁇ ing compounds:
• the most preferred compound for carrying out the present inven ⁇ tion comprises ⁇ [isopropylidene)-amino]oxy ⁇ -acetic acid- 2- (methoxy)-2-oxoethyl ester.
• water-soluble and water-insoluble compounds may be en ⁇ capsulated according to the present invention
• the preferred compounds for carrying-out the invention are substantially water-
• compositions of the invention generally contain, by weight, about 0.1 % to about 90% plant growth regulator, about 0.1% to about 30% PVA, about 1% to about 10% buffer, and about 50% to about 99% water.
• Preferred formulations contain, by weight, about 1% to about 10%
• 35 plant growth regulator, about 2% to about 8% PVA, about 2% to about 6% buffer with the remaining weight of ingredients contain ⁇ ing water and optionally a biocide and a surfactant.
• the range, by weight, of biocide useful in carrying-out the invention is up to about 25%, preferably from about 0.1 to about 5%.
• the surfactant is preferably up to about 20%, most preferably from about 2 to about 6%.
• the PVA for use in the invention also includes those with partial hydrolysis of 87-89% and 78-82%; intermediate hydrolysis of 95.5-96.5%; full hydroly- sis of 98-98,8%; and super hydrolysis of greather than 99.3%.
• Preferred PVA include those with percent hydrolysis greater than 85%.
• the most preferred formulation is a plant growth regulator formulation consisting essentially of about 5% of ⁇ [isopropyli ⁇ dene)amino]oxy ⁇ -acetic acid-2- (methoxy ⁇ 2-oxoethyl ester, about 5% of polyvinyl alcohol, about 0.26 % sodium phosphate dibasic and about 90% water.
• This embodiment of the invention may further include a biocide.
• the particles dispersed in the formulation are greater than about one micron and typically have a mean volume diameter of about greater than 1 micron to about 80 microns. Further embodiments of the invention include particles having a size of about greater than one micron to about 50 microns. Another range of particle size useful in practicing the present invention is a particle that has a mean volume diameter greater than about five microns to about 15 microns. A preferred particle size (mean diameter) is about 6 microns to about 10 microns.
• the surfactants of this invention include salts of alkyl sul ⁇ fates, alkyl or aryl sulfonates, dialkylsulfosuccinates, salts of polyoxyethylene alkyl aryl ether, phosphoric acid, esters, naph- thalenesulfonic acid/formaldehyde condensates, polyoxyethylene alkyl ether, polyoxyethylenepolyoxypropylene block copolymers, sorbitan fatty acid esters, or polyoxyethylene sorbitan fatty acid, esters, monalkyl quaternary salts, dialkyl quaternary salts, di uaternary salts, ethoxylated monoquaternary salts, ethoxylated diquaternary salts, and lauryl betaine.
• An additional release slowing component may be added or dissolved in the water-insoluble plant growth regulator. This component acts to slow the rate of release of the plant growth regulator from the PVA matrix.
• the preferred release slowing component is polyvinyl acetate having a molecular weight of from about 10K to about 200K.
• the formulations are particularly useful as they provide signifi ⁇ cant improvements in a plant growth factor and are stable, not any against particle aggregation, but the PVA also acts to stabi ⁇ lize the plant growth regulator compound.
• These formulations pro ⁇ vides this benefit in the substantial absence of the following ingredients: 1) a thickener; 2) a surfactant (preferably less than 0.1 weight percent); 3) a salt (preferably less than 1%); 4) a xanthate; 5) a starch; and 6) a hydrocarbon (as described in U.S. Patent No. 4,871,766).
• the formulations of the invention are particularly useful as sus- tained release formulations. Further benefits are that the for ⁇ mulations provide significant improvement in a plant growth fac ⁇ tor and also provide a formulation that has low phytotoxicity.
• said plant growth retar ⁇ dant is preferably selected from compounds comprising quaternary ammonium, phosphonium or sulphonium moieties.
• Preferred examples of such plant growth retardants are mepiquat chloride and chloromequat chloride.
• suitable plant growth retardants include compounds containing a nitrogen containing heterocycle, e.g. flurprimidol, paclobutrazol, uniconazol and ancymidol.
• Suitable are furthermore acyclcyclohexanediones (e.g. trinexapac- ethyl and prohexadione-Ca) and da inozide.
• acyclcyclohexanediones e.g. trinexapac- ethyl and prohexadione-Ca
• da inozide e.g. trinexapac- ethyl and prohexadione-Ca
• Mepiquat chloride is the most preferred plant growth retardant.
• the weight ratio of the active ingredients in the inventive mix ⁇ tures is not particularly limited and usually in the range of from 1:50 to 50:1, preferably 1:10 to 10:1.
• Preferred formulations of the invention also provide a signifi ⁇ cant benefit in that they produce a significant improvement in a plant growth factor when applied at low rate.
• Low rate application is defined as a single application rate lower than about 50 g ai/ha (grams of active ingredient per hectacre) .
• An effective number of low rate applications can be made throughout the growing season.
• the low rate application is per ⁇ formed from one to about ten times during the growing season, most preferably from one to about ten times during the growing season.
• Preferred embodiments of the present invention comprise single application rates ranging from about 100 mg ai/ha to about 50 g ai/ha applied from one to four times during a growing season and ranging from about 500 mg ai/ha to about 10 g ai/ha applied from one to four times during a growing season.
• Other rates use- ful for carrying-out the invention include a rate of less than or equal to about 2 g ai/ha and down to about 100 mg ai/ha applied from one to four times during a growing seasons.
• the most pre- 9 ferred single application rate is about 500 mg ai/ha to about 1.5 g ai/ha applied from one to four times during a growing sea ⁇ son.
• the present invention finds its best results in horticultural and agricultural plants and crops.
• the invention provides most con ⁇ sistent improvement of at least one plant growth factor in the following plants: cotton, soybean, peanut, pepper, tomato, wheat, barley, rice plant, apple, citrus, grape, corn and canola.
• the formulations described in this invention are generally applied to the foliage prior to bud and flower development but they can also be applied to the foliage, buds, flowers, or fruits beginning at early bud development (e.g., matchhead square in cotton) in one to four sequential applications. If sequential, ap ⁇ plications are used, applications are preferably timed at approx ⁇ imately 10 to 14 days apart.
• the active ingredient is generally mixed with water as a carrier solution in a dilution sufficient to cover the area.
• the spray volume of the aqueous treatment solution would be about 150 to 500 1/ha for arable crops and up to about 1,500 1/ha fruit trees. Soil drenching is another method of application that is useful when practicing the invention.
• the present invention provides a method which im ⁇ proves the economic or agronomic output of agricultural crops and decreases the amount of material that needs to be used to obtain improvement in a plant growth factor.
• Cotton trials Field tests with Cotton plants were conducted as follows: Cotton plots were laid out about four rows wide and 30 to 40 feet long. The center two rows of each four row plot were treated sprayed over the foliage, buds, blooms, and fruits with the respective applications and the outer two rows were not treated in order to provide a buffer row between plots. In most experiments each treatment was repli ⁇ cated four times and organized in randomized complete block design.
• the first treatments were applied when the plant squares [??] flower buds (i.e., "squares") reached the size of a "match ⁇ head", i.e. when the first square of a typical cotton plant was about the size of a matchhead, and when 50% of the plants had one or more matchhead squares.
• the formula ⁇ tions, except for the mepiquat chloride were applied at 1, 20, 20, 50 and 100 g ai/ha.
• the amount of formulated material to be applied to each treatment was calculated on the basis of the amount of the area to be treated with each rate. For example, a treatment applied at a rate of 1 g of the active ingredient required four applications of 0.022 g ai/ha when four plots (2133 square feet) were treated.
• 0.022 g of active material was mixed with one liter of water or the amount of water necessary for the treated area for the spray volume to be equivalent to about 150 to 205 1/ha.
• Soybean trials Soybean trials were conducted in a green ⁇ house. Soybean seeds were planted in 1000 ml pots in loamy sand soil, fertilized with a slow release fertilizer and al ⁇ lowed to germinate. Plants were thinned to tow two per pot. When the plants reached the third trifoliate stage, equivalent to 11 true leaves, the plants were treated with the appropriate spray solutions AND applied over the top of the plants to the foliage.
• the plants were placed inside a laboratory spray chamber (Al ⁇ len Machine Works, Midland MI) . As noted above, the foliage was sprayed over the top in order to mimic a typical field application. The plants were returned to the greenhouse. Pe ⁇ riodic height measurements, pod numbers, and general plant vigor assessments were conducted. At maturity (approximately six to eight weeks after spraying) the pods were harvested, counted, and the dry-weights recorded.
• Control plants were either those completely untreated or those 5 treated with mepiquat chloride (Pix® plant growth regulator ”) alone. Mepiquat chloride was applied either alone or in combina ⁇ tion with the ethylene biosynthesis inhibitors was used as the control and was applie at a rate of 100 to 200 g ai/ha. When applied in combination, the two compounds were applied using the 10 same "tank-mix" spray solution. However, combinations of mepiquat chloride and ethylene biosynthesis inhibitors may also include separate applications made within 72 hours of each other on the same plants.
• Formulations containing polyvinyl alcohol (PVA) encapsulated ⁇ [isopropylidene)-amino]oxy ⁇ -acetic acid-2-(methoxy) -2-oxoethyl ester were prepared by 20 first making a 10% solution of PVA in an aqueous solution of so ⁇ dium phosphate dibasic buffer.
• PVA Polyvinyl alcohol
• Various PVA Air Products, Inc. was used having different molecular weights and various degrees of hydrolysis. Table 1 lists the different PVA used.
• the pH of the 10% PVA solutions was adjusted to about 4.1.
• the 40 oxime-ether was mixed into the PVA solution under A high shear until a finely dispersed emulsion was obtained.
• a biocide Pro- xel ® GXI biocide
• the solu ⁇ tions were passed once through a high shear Eiger Mini 50 (e.g., a bead mill with an 85% chamber loading of 1 mm glass beads) at ⁇ 5 3000 RMP.
• a milky solution was obtained and passed through a 0.45 micron screen.
• the formulations prepared contained about 5% sub- stituted oxi e-ether, about 5% PVA, about 0.12% biocide, about 0.26% sodium phosphate dibasic and about 89.62% water.
• Particle size was measured using an Accusizer Optical Particle Sizer. The particle size measured (mean volume) for each formulation was about ten microns.
• Encapsulated ⁇ [isoprnpylidene) -amino)oxy ⁇ -acetic acid-2- (methoxy)-2-oxoethyl ester formulations were prepared as in Example 1 and combined with mepiquat chloride and mixed in one liter of water. Two formulations were prepared. The first formulation contained PVA with a molecular weight of 44-66K and partial degree of hydrolysis (87-89%) (AIRVOL ® 523 S polyvinyl al- cohol) . The second formulation contained PVA with a molecular of 70-90k and was partially hydrolyzed (87-89%) . Cotton plants were treated as described above.
• the formulations were also tested in soybeans at rates of 1, 10 and 20 g ai/ha (greenhouse) and compared to an untreated control. The formulations showed an improvement over the untreated control and were comparable to the plants treated with mepiquat chloride.
• the germination media was placed in growth chambers.
• the growth media consisted of either a loamy sand or an absorbent foam cores (OASIS ® CELAN START ® grow- ing media) .
• the seeds were placed at uniform depth in the media.
• Growth chamber temperatures were held at approximately 70°F night/80°F day (12h/12h) for the warm treatments, and approxi- ately 55°F night/70°F day (12h/12h) for the cool treatments. Emerged seedlings were counted on a regular basis. Radiant energy was provided by fluorescent and incandescent light sources for the daytime period. The results for the cool treatments are listed Table 6.
• Table 6 shows an improvement in the rate of germination at cool 5 temperature. Signification improvement was seen with the 205S formulation at about five days (e.g., about a two-fold increase in germination rate up to a four-fold increase in germination rate) .
• Soybean seeds were planted in loamy sand soil in 1 liter pots in the greenhouse and thinned to three plants per pot after emer- 5 gence.
• 100 ml of a solution containing the equivalent of 0, 30, or 100 or 300 g ai/ha ⁇ [isopropyli- dene) -amino ⁇ -acetic acid-2- (methoxy) -2-oxoethyl ester (99% Tech ⁇ nical Grade ("tech.”); BASF Corporation) (free and encapsulated) 10 was applied, directly to the soil around the base of the plants. Plant heights were measured at regular intervals and upon matu ⁇ rity, the plants were harvested for fresh and dry weights of the shoots and the bean pods. The results are displayed in Tabeles 8 & 9.
• Ethylene inhibition was determined in barley leaves treated with ⁇ [isopropylidene) -amino] oxy ⁇ -acetic acid-2- (methoxy) -2-oxoethyl ester (99% Technical Grade ("tech.”); BASF Corporation) (both en ⁇ capsulated and free) using various formulations ad described in Example 1.
• the formulations were applied to seven-day-old green ⁇ house grown barley leaves at rates of 30 g ai/ha and 300 g ai/ha.
• the treatments were carried out in a spray chamber at 750 1/has in aqueous solutions made with 0.1 M potassium phosphate buffer.

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  • 1996-12-17 TR TR1998/01143T patent/TR199801143T2/xx unknown
  • 1996-12-17 WO PCT/EP1996/005669 patent/WO1997023130A1/en not_active Application Discontinuation
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  • 1996-12-17 EP EP96943984A patent/EP0874545A1/de not_active Withdrawn
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