MXPA97000137A - Application of low regime of biosynthesis inhibitors or etil action - Google Patents

Abstract

The present invention relates to: The method of the invention provides an improvement of a plant growth factor, by providing an ethylene inhibitor plant growth regulator or a plant, such as cotton or soybean at a low rate. Plant growth regulators of specific plants include compounds covered by the general formula (I) or (II), wherein R1 and R2 independently of each other are C1-C6 alkyl, n is 2 or 3, and R3 is hydrogen or C1 alkyl. -C6 The specific compounds employed by the method of the invention include 2- (methoxy) -2-oxoethyl ester of. { [(isopropylidene) -amino] oxy} -acetic acid, 2- (hexyloxy) -2-oxoethyl ester of. { [(isopropylidene) -amino] oxyl} -acetic acid, 2- (isopropyloxy) -2-oxyethyl ester of. { [(cyclohexylidene) -amino] oxy} -acetic, [(isopropylidene) amino] oxyacetic acid, and aminooxyacetic acid

Description

"APPLICATION TO LOW INJURY REGIME OF BIOSYNTHESIS OR ETHYLENE ACTION" This application claims the benefit of the 5 Provisional North American Application Number 06/009050 filed on December 21, 1995.

NOTICE OF COPENDING PATENT APPLICATIONS r-Z The following patent applications are co-pending with the United States Patent and Trademark Office with this application: 1. Plant Growth Retardants in Combination with Biosynthesis Inhibitors or Action Ethylene, US Patent Application Number of Series, filed on the same date as the present one and incorporated herein by reference; 2. Encapsulated Plant Growth Regulatory Formulations, North American Patent Application Serial Number, filed on the same date as the present one and incorporated herein by reference; 3. Regulatory Formulations of Encapsulated Plant Growth and Applications, Patent Application North American Serial Number filed on the same date as the present one and incorporated herein by reference. 4. Plant Growth Regulatory Formulations Encapsulated in Combination with Plant Growth Retardants, North American Patent Application Serial number, presented on the same date as the present one and incorporated herein by reference.

. Plant Growth Regulators in Pyrrolidone Solvents, American Patent Application Number, filed on the same date as the present one and incorporated herein by reference; 6. Improvement of the Seed Germination Regime With Application of Ethylene Biosynthesis Inhibitors, North American Patent Application Number, filed on the same date as the present one and incorporated herein by referendum; and 7. Aminoethoxyvinylglycine in combination with a Plant Growth Regulator, North American Patent Application Number, filed on the same date as the present one and incorporated herein by reference.

APPLICATIONS IN FIELD OF THE INVENTION 4 - It has an intense economic benefit, since it provides less lodging in small grains and reduction of excessive vegetative growth. It also provides more uniform maturation in cotton. Three groups of inhibitors of gibberiline biosynthesis are known. The first group includes compounds with quaternary ammonium, phosphonium or sulfonium residues. An example of a compound of this group is mepiquat chloride, described in U.S. Patent No. 3,905,798 and incorporated herein by reference. Mepiquat chloride can increase cotton yields, capsule loading, cotton fiber yield and seed yield. Mepiquat chloride is also known to reduce vegetative growth, height of the plant and rot or decay of the capsule. Mepiquat chloride also induces early uniform maturity if the plants are treated early during their development. 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, paclobutrazol, uniconazole and ancymidol.

The present invention relates generally to the field of agriculture and specifically to compositions and use of plant growth regulators.

BACKGROUND OF THE INVENTION Agricultural workers actively seek ways to improve the economic performance of commercial crops. For example, in cotton crops, workers seek to improve such growth factors as increased capsule solidification, increased flower initiation, decreased floral cut or abscission, decreased abscission or capsule cutting, and improved root growth. The workers also seek to increase the tolerance of the plants to the environmental effort. Formulations containing plant growth regulators (PGRs) have been developed to improve the economic performance of agricultural plants. The retarders and growth inhibitors of biosynthesis or ethylene action plants are of two types of PGRs. Some plant growth retardants have been shown to inhibit the biosynthesis of gibberilin, resulting in the reduction of shoot height in small grains and cotton. This reduction at shoot height The third group encompasses acylcyclohexanediones (such as trinexapac-ethyl and prohexanedione-Ca) and gives inozide. It is known that ethylene is involved in plant stress reactions and plant senescence. Ethylene is also involved in abscission or cutting of leaves, flowers and fruits. Therefore, agents that inhibit or regulate the production of ethylene or control its action in plants have been developed in an effort to improve the yield of agricultural crops. Ethylene biosynthesis inhibitors include substituted oxime-ethers as described in U.S. Patent No. 4,744,811, incorporated herein by reference. These compounds are also described in PCT Application WO 95-02211, which is incorporated herein by reference as being soil modification compositions that increase nitrogen uptake by higher plants. Other inhibitors of ethylene biosynthesis or action include aminoethoxyvinylglycine ("AVG"), aminooxyacetic acid ("AOA"), rhizobitoxin, and methoxyvinyl glycine ("MVG"). Silver ions (e.g., silver thiosulfate) and 2,5-norbornadiene inhibit the action of ethylene.

Regulators of plant growth have also been used to protect crops from the effects of environmental stress. T.J. Gianfagna et al., "Mode or Action and Use of Growth Retardants in Reducing the Effects on Environmental Stress in Horticultural Crops: Karssen CN et al. (Editors) Progress in Plant Growth Regulation, pp. 778-87 (1992). Researchers found that if ethephon is applied at a low rate (0.08 mM) it significantly retards flowering in the peach and reduces side effects.The researchers also found that ethephon increased the yields and resistance of several horticultural plants. have been developed as a means to improve yields of the agricultural crop, certain obstacles make the effective use of PGR prohibitive, for example, many of the compounds exhibit phytotoxicity, and other compounds are difficult to synthesize. be effective, for example, PCT Application Number WO 93/07747, incorporated herein by reference The invention relates to an improvement in a plant growth factor by applying aminoethoxyvinylglycine ("AVG"), an inhibitor of ethylene biosynthesis, to cotton plants. As the AVG treatment regimen increased, so did the improvement (WO 93/07747, Examples 2 to 4). Assuming that a spray volume of 500 liters per hectare was used, the application regimes described in Patent Number WO 93/07747 would be from about 62.5 to 500 grams ai / hectare (ai = active ingredient). The response of the maximum regime occurs at the highest rates. High-speed applications can result in significant waste of material and can result in the discharge of PGRs into the surrounding environment. Also, even though many of these compounds can induce a habit of beneficial growth, they do not provide a consistent improvement in plant growth factors. Other compounds may lose their effectiveness or cause a reduction in performance when applied to species that are under some form of environmental stress. Therefore, an object of the invention is to formulate a PGR that not only improves a plant growth factor, but also reduces toxicity. It is also an object of the present invention to provide in a PGR that has lower application regimes and has limited environmental impact.

COMPENDIUM OF THE INVENTION A method is provided herein for improving at least one growth factor in a plant comprising applying an ethylene biosynthesis inhibitor or ethylene action to the plant, at a low rate. An improvement in a plant growth factor is defined as an agronomic improvement of plant growth such as increased floral initiation (square), increased flower retention, increased fruit retention, increased frame retention, increased capsule retention, growth increased root, decreased internode length, increased stress tolerance, decreased wilting, decreased senescence, darker green pigmentation, increased germination regime, increased tolerance at low and high temperatures and increased crop yield, ie, a favorable alteration of the physiology or growth of plants or an increase or decrease in the growth of plants that leads to an economic or agronomic benefit, the best in the growth factors that result from the inhibition of ethylene production is of course preferred.

DETAILED DESCRIPTION OF THE INVENTION It has surprisingly been found that a low-oxime-substituted ether application, having the formula: wherein R1 and R2 independently of one another are alkyl of 1 carbon atom to 6 carbon atoms, n is 2 or 3 and R3 is hydrogen or alkyl of 1 carbon atom at -6 carbon atoms improving at least one factor of plant growth on a consistent basis. Other compounds of the present invention provide an improvement in at least one plant growth factor. Examples of the other compounds that may be used include [(isopropylidene) -amino] oxy-acetic acid, represented by the structure: - Another example of a compound that can be used in the present invention is aminooxyacetic acid ("AOA"), represented by the following structure: HO ~ (IV) H-.N- Preferred oxime-ethers for use in the method include the following compounds: 1) ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl, represented by the structure: 2) ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (hexyloxy) -2-oxoethyl, represented by the structure: (VI) and 3) ester of. { [(cyclohexylidene) -amino] oxy} -acetic acid-2- (isopropyloxy) -2-oxyethyl-ester of (methoxy) -2-oxoethyl, represented by the structure: The compound especially preferred for carrying out the present invention comprises the ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -oxoethyl. The low-regime application is defined as a single application regime of less than approximately 50 grams of ai / ha (grams of active ingredient per hectare). An effective number of low-rate applications can be made through the growing season. Preferably, the low rate application is carried out from one to ten times during the growing season and more preferably from one to about four times during the growing season. Preferred embodiments of the present invention comprise individual application regimes ranging from about 100 milligrams of ai / ha to about 50 grams of ai / ha that are applied one to four times during a growing season and varying from about 500 milligrams. from the active ingredient per hectare to approximately 10 grams of the active ingredient per hectare applied one to four times during a growing season. Other regimens useful for carrying out the invention include a regimen of less than or equal to about 2 grams of the active ingredient per hectare and up to about 100 milligrams of the active ingredient per hectare that is applied one to four times during a growing season. The particularly preferred individual application regimen is from about 500 milligrams of the active ingredient per hectare to about 1.5 grams of the active ingredient per hectare from one to four times during a growing season. The present invention finds its best results in horticultural and agricultural plants and crops. The invention provides a very consistent improvement of at least one plant growth factor in the following plants: cotton, soybeans, peanuts, pepper, tomatoes, wheat, barley, rice plants, apples, citrus fruits, grapes and cañola of corn. There is also improvement in peat or turf. Preferred formulations of the low-rate application include those formulations that provide an ethylene inhibitor in an effective amount to obtain a compatible improvement in a plant growth factor, ie, those formulations that provide a statistically significant improvement (v. ., where P = 0.15 or less) when compared to untreated plants where the improvement is obtained more than about 50 percent of the time, preferably more than 60 percent of the time, more preferably more 75 percent of the time and most preferred, more than 90 percent of the time. In a preferred embodiment of the invention, the enhancement of the plant growth factor varies from about 4 percent to about 60 percent relative to untreated plants or those plants treated with mepiquat chloride. Tests carried out at 50 grams of the active ingredient per hectare and larger quantities gave incompatible results. Accordingly, the present invention provides surprising and unexpected results since they obtain superior results at low regimes. The formulations described in this invention, usually, they are applied to the foliage before the buds or buds, flowers or fruits that begin the development of bud or bud early (eg, head of equalization in the cotton) in one or more applications in sequence . If applications are used in sequence, the applications are preferably synchronized at a distance of approximately 10 to 14 days, when applied by spraying, the active ingredient is usually mixed with water as a carrier solution at a dilution sufficient to cover the area. Typically, the spray volume of the aqueous treatment solution would be about 150 to 500 liters per hectare for harvests capable of plowing and up to about 1500 liters per hectare for fruit trees. Soaking the soil is another method of application that is useful when the invention is practiced. Therefore, the present invention provides a method that improves the economic or agronomic performance of agricultural crops and decreases the amount of material that needs to be used to obtain the improvement in a plant growth factor. The following examples are illustrative only and are not intended to limit the invention in any way.

EXPERIMENTS 1. Cotton tests. Field trials with cotton plants were carried out as follows: the cotton plots were placed at approximately four to six rows wide and from 9,144 to 12,192 meters long. In two trials, the two middle rows of four row plots were sprinkled over foliage, buds or buds, flowers and fruit with respective applications and the two outside rows were not treated to provide a buffer row between the parcels. In the remaining trials, all the rows were sprayed on top of the foliage, buds or buds, flowers and fruits but only the two centered rows were harvested. In most of the experiments, each treatment doubled four times and was organized in randomized complete block design. The first treatments were applied when the buds or buds of the flower (ie, "frames") reached the size of a "matching head", that is, when the first frame of a typical cotton plant was about the size of a matching head and when 50 percent of the plants had one or more matching head squares, In general, the formulations except mepiquat chloride were applied at 1, 10, 20, 50 and 100 grams of the active ingredient per hectare . The amount of the formulated material to be applied to each treatment was calculated based on the amount of the area to be treated with each regimen. For example, a treatment applied to a regimen of 1 gram of the active ingredient required four applications of 0.022 gram of active ingredient per hectare when four plots (137.58 square meters) were treated. Therefore, the 0.022 gram of active material was mixed with one liter of water or the amount of water needed for the treated area so that the spraying volume was equivalent to approximately 150 to 250 liters per hectare. Subsequently, to the second and / or the final applications, the numbers and locations in the plant of the boxes, flowers and capsules were recorded and when possible capsule weights or yields of the seed cotton were obtained. The tests in the greenhouse were carried out in the following way: the cotton was grown in pots of 2 to 5 liters in the greenhouse, approximately one plant per pot either in the field land or a mixture for land-free planting . The plants permenecided in the greenhouse and the matching head frame stage described in the field methods above, the treatments were applied to the foliage, the frames, the flowers and / or the capsules either by spraying in a laboratory chamber sprayer (e.g., Alien Machine Works, of Midland, MI) or by placing the pots on the ground outside the greenhouse and spraying with a hand spraying device. The spraying volumes were approximately equivalent to those described in the field methods. The plants were then returned to the greenhouse and capsule beads, capsule weights or seed cotton yields were obtained from the plants. 2. Soy bean trials. Bean bean trials were carried out in a greenhouse. The soybeans seeds were planted in pots of 1000 milliliter capacity in sandy clay soil, fertilized with a slow release fertilizer and allowed to germinate. The plants were thinned to two per pot. When the plants reached the third step of trifoliate, equivalent to 11 true leaves, the plants were treated with appropriate spray solutions applied above the top of the plants to the foliage. The plants were placed inside a laboratory spraying chamber (Alien Machine, of Midland, MI). As mentioned above, the foliage was sprayed above the top in order to mimic a typical field application. The plants were returned to the greenhouse. The periodic height measurements, the pod numbers and the general assessments of plant vigor were carried out. During maturity (approximately six to eight weeks after spraying) the pods were harvested, counted and recorded by their dry weights. The control plants were those either completely untreated or those treated with mepiquat chloride alone ("plant growth regulator" Pix®). Mepiquat chloride was applied either alone or in combination with the ethylene biosynthesis inhibitors at a rate of 12 to 200 grams of the active ingredient per hectare. When applied in combination the two compounds were applied using the same "tank mix" spraying solution, however, combinations of mepiquat chloride and ethylene biosynthesis inhibitors may also include separate applications made within 72 hours, a of the other in the same plants. Other methods and applications for cotton, soybeans and other crops will be described below.

EXAMPLE 1 The ester of was mixed. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl unencapsulated (99 percent Technical Quality; BASF) either manually or with a magnetic stirrer in a volume of water equivalent to 150 to 250 liters per hectare for the area what is going to be The formulations were tested in cotton at 10 grams of the active ingredient per hectare and 100 grams of the active ingredient per hectare (a single ;/ application; in the greenhouse). They were used for control 10 untreated plants. The weight of the capsules was obtained approximately six weeks after the first treatment. The formulations were also treated in soybeans to 1, 10 and 20 grams of the active ingredient by hectares (only one application, in the greenhouse) and compared with an untreated control group to a group treated with mepiquat chloride (Pix® plant growth regulator). The results of the tests are disclosed in Tables 1 and 2.

Table 1 (Cotton) Capsule weight Regime kilograms of active ingredient / hectare 0.010 0.10 e (0.200 kilograms of active ingredient / hectare) tec. 99% 93 e = mepiquat chloride Table 2 5 (Soybeans) Number of pods Regimen kilogram of,. 'active ingredient / hectare 0.0010 0.010 0.02 control 18.2 18.2 18.2 me (0.012 gram of active ingredient / hectare) 19.2 19.2 19.2 (105%) (105%) (105%) 5 technical class 23.2 18.4 21.6 (127%) (101% ) (119%) me = mepiquat chloride The results of the cotton test show improvement when compared to those plants treated with mepiquat chloride alone at both regimes of 1 and 20 grams per hectare, with the greatest improvement at a rate of 1 gram of the ingredient active per hectare. The data did not show an improvement of mepiquat chloride with respect to the untreated test. The experiment was also carried out with two applications at the same regimes and comparable results were obtained. Soy bean data show a considerable improvement of a plant growth factor at 20 and 1 gram regimes of active ingredient per hectare (19 percent and 27 percent). Surprisingly, the application at low regime to 1 gram of active ingredient per hectare showed a significant improvement (27 percent) in relation to the untreated test.

EXAMPLE 2 Formulations containing ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl encapsulated with polyvinyl alcohol (PVA) (99 percent Technical Grade; BASF Corporation) as described in the North American Patent Application entitled "Encapsulated Plant Growth Regulator Formulations" on the same date as the present one. Briefly, a 10 percent solution of PVA in water was prepared and the pH adjusted to about 4.1 using dibasic sodium phosphate as a stabilizer system. The oxime-ether was mixed with the PVA solution under high shear until a finely dispersed emulsion was obtained. A biocide (Proxel® GXI biocide) was added to the emulsion and mixed. The solution was passed once through a high-shear Eiger Mini 50 mill (v.gr., a bead mill with a chamber load at 85 percent glass beads of 1 millimeter) at 3000 revolutions per minute. A milky solution was obtained and passed through a 0.45 micron sieve. The typical particle size obtained was 10 microns. The formulations prepared contained about 5 percent 5-percent substituted oxime-ether, about 5 percent PVA, about 0.12 percent of the biocide, about 0.26 percent of the dibasic sodium phosphate, and about 89.62 percent of water. Three encapsulated formulations were prepared using a different PVA. The first formulation contained PVA having a molecular weight of 15-27K and partial hydrolysis of 87 percent to 89 percent (AIRVOL® 205 S, Air Products). The second formulation contained PVA having a molecular weight of 45-65K and a partial hydrolysis of 87 percent to 89 percent (AIRVOL® 523 S, Air Products). The third formulation contained PVA that has a molecular weight of 70 to 90K and a partial hydrolysis of 87 to 89 percent (AIRVOL® 540 S, Air Products). The formulations were tested on soybeans, regimes of 1, 10 and 20 grams of active ingredient per hectare (in the greenhouse) and compared with a control and the ester. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl unencapsulated (99% Technical Quality); BASF Corporation). The results are reported in Table 3.

Table 3 (Soybeans) Number of pods Kg regime of active ingredient / hectare 0.0010 0.010 0.020 control 18.2 18.2 18.2 technical quality 23.2 18.4 21.6 (127%) (101%) (119%) encapsulated technical quality 23.2 21.8 21.3 (205S) (127%) (120%) (118 %) encapsulated technical quality 20.4 22.6 23.0 (523S) (112%) (124%) (126%) encapsulated technical quality 25.8 19.2 19.2 (540S) (142%) (105%) (105%) The results establish that at low levels, the ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl encapsulated significantly and consistently improves the number of pods in the soybean plant. Performance studies on cotton were also carried out using encapsulated PVA compositions (540S as described above). Thirty-seven trials were conducted, usually as described above for cotton field studies. The average relative yields were calculated in comparison with the values obtained from the untreated plants. The results are shown in Table 4.

Table 4 (Cotton) performance Regime (gram / hectare) 0.5 1 10 20 50 Relative performance 96% 100% 105% 97% 95% Frequency of positive performance 18% 43% 59% 18% 25% The best results (5 percent) were obtained at application rates of 10 grams per hectare. Also, the formulation applied to 10 grams per hectare had the highest frequency of positive results. The yields for the formulations applied at 0.5, 20 and 50 grams per hectare regimes were lower than for the untreated plants. The results for the plants treated with application regimes of 1 gram per hectare were equal to the results obtained for the untreated plants.

EXAMPLE 3 Formulations containing an ester mixture were prepared. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl (99% Technical Quality; BASF Corporation) and mepiquat chloride (PIX® plant growth regulator) by adding both active ingredients to an aqueous spray solution. The cotton plants were treated with from 1 to 100 grams per hectare of the substituted oxime-ether and 12, 100 or 200 grams of the active ingredient per hectare of mepiquat chloride (Pix® plant growth regulator) when used alone or in combination with oxime-ether. The formulations were applied with either two, three or four applications during the course of the experiment at the field test sites and in a greenhouse. Mepiquat chloride was used as a control. The number of frames, the number of capsules, the yield, the height of the plant and the capsule weight were calculated. Performance data were measured either as kilograms per plot or pounds per area. The results are listed in Tables 5 to 8. The results show as a percentage of the plants treated with mepiquat chloride ("me") alone.

Table 5 Number of Tables1 Regime (kilograms of active ingredient / hectare) 0.001 0.010 0.020 0.050 0.10 me 8.3 8.3 8.3 8.3 8.3 me + tec. 10.3 8.2 8.11 9.0 8.3 (124%) (99%) (98%) (108%) (99%) 1 the map data made after the second of four applications (Field Data); me = mepiquat chloride Table 6 Number of buds Regimen (kilogram of active ingredient / hectare) 0.001 0.010 0.020 0.050 0.10 me1 7.8 7.8 7.8 7.8 7.8 me + tec1 10.7 9.5 8.3 8.5 9.3 (137%) (122%) (106%) (109%) (119%) mc 4.1 4.1 4.1 4.1 4.1 me + tec-1 4.9 4.4 (122%) (107%) (129%) (134%) (129%) me7.2 7.2 7.2 7.2 7.2 mo + tec- 5.5 6.5 5.5 5.8 5.8 (77% ) (90%: (77%) (80%) (80%) me + tec- 86% 82% 1 Four applications (field test) 2 Three applications (field test) 3 Four applications (greenhouse) 4 Two applications (greenhouse) me = mepiquat chloride Table 7 performance Regime (kilograms of active ingredient / hectare) 0.0010 0.010 0.020 0.050 0.1 mc1 3.6 3.6 3.6 3.6 3.6 c + tec1 4.0 4.1 4.3 3.7 3.4 (111%) (114%) (119%) (103%) (94%) mc 2.18 2.18 2.18 2.18 2.18 me + tec ^ 2.66 2.33 2.67 2.88 2.39 (123%) (107%) (122%) (132%) (109%) 1 Four applications (field test) 2 Three applications (field test) me = mepiquat chloride Table 8 Weight of capsules1 Regime (kilogram of active ingredient / hectare) 0.010 0.10 me (0.200 kilogram of active ingredient / hectare) 87% 83% e + tec 116% 97% tec 99% 93% 1 Two applications (greenhouse) me = mepiquat chloride The data shows that the application regimes of less than 50 grams of the active ingredient per hectare provided the most consistent and maximum response. Two thirds of the cases for the number of capsules showed an improvement at application regimes of less than 50 grams of the active ingredient per hectare. Similarly, two thirds of the cases for the performance data showed a considerable improvement. An improvement was demonstrated in more than half of the tests for substituted oxime-ether applied to regimes less than 50 grams of the active ingredient per hectare. Eleven additional field trials were carried out on the cotton. The plants were treated with mepiquat chloride alone and in combination with ester. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl (99 percent Technical Quality; BASF). Mepiquat chloride was applied at a rate of 12 grams per hectare in all applications. The ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl (99 percent Technical Quality, BASF ("technical quality")) was applied at regimes of 1 gram per hectare, 10 grams per hectare, 20 grams per hectare and 50 grams per hectare. The mean values (yield) for the treated plants were calculated and compared with the average values obtained for the untreated plants. The results are presented in Table 9.

Table 9 (Cotton) performance Regime (gram / hectare) 1 10 20 me only me (12 grams / hectare) 101% Relative performance of me + technical class 106% 104% 85% 101% Positive performance frequency 73% 54% 36% me = mepiquat chloride The data in Table 9 indicates that the best results were obtained at the lowest regimes, that is, less than or equal to 10 grams per hectare. The highest frequency of positive yield was obtained at 1 gram per hectare. The same formulations were used to treat the soybean plants and were compared with the untreated plants, the plants treated with mepiquat chloride and the plants treated with the ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl. The results are listed in Table 10. Table 10 (Soybeans) Number of pods1 Regime (kilograms of active ingredient / hectare) 0.001 0.010 0.020 control 18.2 18.2 18.2 e (0.012 kilogram of active ingredient / hectare) 19.2 19.2 19.2 (105%) (105%) (105%) technical quality 23.2 18.4 21.6 (127%) (101%) (119%) tec + me 22.6 16.8 19.6 (124%) (92%) (108%) 1 One application (greenhouse) me = mepiquat chloride In this experiment, treatment at low rate (1 gram of active ingredient per hectare) using the combination of oxime-ether and mepi'quat chloride provided a significant improvement (27 percent) in the number of pods when compared to the untreated control and compared with application regimes greater than 1 gram of the active ingredient per hectare.

EXAMPLE 4 Ester formulations were prepared. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl encapsulated as in Example 2 and combined with mepiquat chloride and mixed in one liter of water.

Three formulations were prepared. The first formulation contained PVA with a molecular weight of 44 to 66K and a degree of partial hydrolysis (87 percent to 89 percent) (AIRVOL® 523 S, polyvinyl alcohol). The second formulation contained PVA with a molecular weight of 70 to 90K and was partially hydrolyzed (87 percent to 89 percent) (Airvol 540®, polyvinyl alcohol). The third contained PVA with a molecular weight of 15 to 27 K and was also partially hydrolyzed (87 percent to 89 percent) (Airvol® 205S, polyvinyl alcohol). The cotton plants were treated as described above. The plants were treated and the plants treated with mepiquat chloride were used as a comparison (Application rate of approximately 0.012 kilogram of active ingredient per hectare in all studies). The number of frames and capsules was measured and the results as a percentage of the plants treated with chloride mepiquat are only displayed in Tables 11 to 13.

Table 11 (Cotton) 15 Number of tables1 r- Diet (kilograms of ingredient 20 active / hectare) 0.001 0.010 0.020 0.050 0.10 e 8.3 8.3 8.3 8.3 8.3 me + encap with / 523S 11.3 10.7 8.7 9.8 8.9 (136%) (129% ) (105%) (115%) (107%) me + encap with / 540S 9.8 10.5 8.2 10.1 7.0 (118%) (126%) (99%) (122%) (84%) 1 Measured after two applications in sequence (field test) me = mepiquat chloride Table 12 (Cotton) Number of capsules -.0 Diet (kilograms of active ingredient / hectare) 0.001 0.010 0.020 me 1 7.8 7.8 7.8 me + encap with / 523 S 10.0 8.1 7.3 (128%) (104%) 15 me + 3encap with / 54031 9.9 7.6 9.0 (127 %) (97%) (115%) me 4.1 4.1 4.1 me + encap with / 523S2 5.7 5.3 5.8 (139%) (202%) (149%) i9 ^ me + encap with 5 OS2 6.2 8.3 6.1 (151%) (202%) (149%) me3 7.2 7.2 7.2 me + encap with / 523S3 6.2 7.2 6.5 (86%) (100%) (90%) me + encap with / 540S3 9.0 7.0 7.8 (125%) (97%) (94%) me4 3.35 3.35 me + encap with / 523S4 3.65 3.90 (109%) (116%) 30 me + encap with / 540S4 4.22 3.60 (126%) (108%) Table 12 (Continued) Number of capsules Diet (kilograms of active ingredient / hectare) 0.050 0.10 me1 7.8 7.8 me + encap with / 523 S 7.6 9.2 me + 3encap with / 54031 7.3 6.9 (94%) (88%) me2 4.1 4.1 me + encap with / 523S2 6.2 6.4 (151%) (156%) me + encap with 540S2 6.2 5.9 (151%) (144%) me3 7.2 7.2 me + encap with / 523S3 6.5 6.2 (80%) (86%) me + encap with / 540S3 6.8 7.3 (94%) (101%) me4 3.35 e + encap with / 523S4 3.95 (118%) me + encap with 540S4 3.30 (99%) Four applications (field data) 2 Three applications (field data) 3 Four applications (field data) 4 Collected after the second of the two applications in sequence e = mepiquat chloride Table 13 (Cotton) performance Regime (kilograms of: active ingredient / hectare) 0.001 0.010 0.020 0.050 0.10 me 1 1365 1365 1365 1365 1365 me + 523S1 1669 1252 1290 1138 1252 (122%) (92%) (94%) (83%) (92%) me + 540S1 1024 1290 1328 1138 1100 (75%) (94%) (97%) (83%) (81%) me2 2.18 2.18 2.18 2.18 2.18 me + 523S2 2.87 3.25 2.8 2.76 2.82 (131%) (149%) (128%) (127%) (129%) me + 540S2 3.43 3.44 3.57 3.4 3.27 (157%) (158%) (164%) (156%) (150%) 1 Four applications (field test) 2 Three applications (field test) me = mepiquat chloride Examination of the data in Tables 10 to 14 confirms that the present invention provides a consistent improvement in plant growth factor at low regimes. For example, during the application of low regimen of 1 gram of active ingredient per hectare, the formulation provides significant improvement (from about 5 percent to about 60 percent) in relation to the plants treated with mepiquat chloride. Thirty-four additional field tests were carried out using the formulations encapsulated with PVA (54OS) in combination with mepiquat chloride. Mepiquat chloride was applied for all tests at a rate of 12 grams per hectare. The ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl was applied at 0.5 gram per hectare, 1 gram per hectare, 10 grams per hectare, 20 grams per hectare and 50 grams per hectare. The results are presented as a percentage in Table 14.

Table 14 Relative performance percentage Regimen (gram / hectare) 0.5g lg lOg 20g 50g me (12 grams / hectare) 103% 103% 103% 104% 103% me + Forms of PVA Encapsulated 110% 105% 106% 99% 90% Frequency of Positive Returns 64 % 72% 77% 56% 25% me = mepiquat chloride The results for plants treated with mepiquat chloride alone had a mean value of 103 percent when compared with untreated plants with a positive frequency of 60 percent of those not treated. The maximum yield for the combination was at a rate of 0.5 gram per hectare. There was a significant increase with the combination of less than 20 grams per hectare. The formulations were also tested on soybeans at rates of 1, 10 and 20 grams per hectare (greenhouse) and were compared with an untreated control. The formulations showed an improvement relative to the untreated control and were comparable to plants treated with mepiquat chloride. Another study of greenhouse soybeans was repeated with the 54OS formulations. An average yield data (seed weight) was obtained at 10 and 50 grams per hectare, the data obtained showed a decrease in yield when measured as the percentage of untreated plants (26 percent, 30 percent and 24 percent at regimes of 1, 10 and 50 grams per hectare, respectively).

EXAMPLE 5 A greenhouse test was carried out on cotton plants (Delta Pine 50 cv.). The individual plants were grown on a peat-based substrate in 5 liter containers. Uniformly applied as needed was water and nutritional compounds. The plants were treated in their leaves with aqueous sprays of the ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl encapsulated with PVA (540S) in combination with metiquat chloride and the plants were treated in the growth stage 61 (beginning of flowering) using approximately 500 liters per hectare of liquid . The plants were also treated with mepiquat chloride alone.

For all studies, mepiquat chloride was applied at regimes of 10 and 100 grams per hectare. The ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl was applied at regimes of 10 and 100 grams per hectare. Two days after imposing the one-week treatment subjected to drought on part of the plants reducing the water supply to approximately 30 percent of the regular dosage. The leaves of the plants in this way wilted permanently but did not die. The capsules were harvested fresh when the old ones from the control plants had reached their final size. The length of the shoot, the number of capsules per plant and the fresh weight of the capsules per plant were assessed and calculated. The results did not show a compatible improvement in relation to those not treated. Even though some improvement was observed in relation to the untreated plants and the plants treated with mepiquat, a decrease in the length of the shoot and the number of capsules at both regimes were also observed. For outbreak length measurements, the results of the combination were 84 percent to 93 percent (which are measured as the percentage of untreated plants). In the treated plants subjected to drought, the results for the combination varied from 93 percent to 99 percent of the untreated ones. The results for the 540S formulations were 100 percent of those not treated at 10 grams per hectare and 103 percent of those not treated at 100 grams per hectare (108 percent and 97 percent at regimes of 10 grams per hectare and 100 grams per hectare, respectively for plants subjected to drought). The plants treated with mepiquar chloride showed only a decrease in the length of the shoot, 95 percent of the untreated to 10 grams per hectare and 85 percent of the untreated to 100 grams per hectare (97 percent and 96 percent for plants submitted to water, the number of capsules varied from 84 percent to 102 percent of those not treated for the plants treated with the combination (94 percent to 100 percent for plants subjected to drought, respectively) The number of capsules for plants treated with 540S was 100 percent of those not treated at 10 grams per hectare and 97 grams per hectare of those not treated at 100 grams per hectare (106 percent and 103 percent for plants subjected to drought.) The results for plants treated with mepiquat chloride alone were 92 percent of those not treated for treated plants at 10 grams per hectare and 87 percent of those not treated at 100 g per hectare (102 percent and 95 percent for plants subject to drought, respectively).

The fresh weight of the capsules per plant was measured and varied from 89 percent to 95 percent of the untreated plants for the plants treated with the combination (from 87 percent to 101 percent for plants subjected to drought, respectively). The results for plants treated with 540S was 97 percent of the np treated at a regimen of 10 grams per hectare and 91 percent of those not treated at 100 grams per hectare (from 96 percent to 103 percent for plants subjected to drought). The results for plants treated with mepiquat chloride were only 95 percent for those not treated at 10 grams per hectare and 87 percent of those not treated at 100 grams per hectare (96 percent and 113 percent for plants submitted to drought, respectively).

EXAMPLE 6 Winter wheat on dry land (not irrigated) was grown in the field. Ester was applied. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl encapsulated with PVA prepared as described in Example 2 (540S), as a foliar treatment in wheat at rates of 1, 10, 20 and 50 grams of the active ingredient per hectare beginning during the lengthening and continuing every 14 days later for four applications in sequence. The tests were carried out in a randomized complete block design, plots of 3,048 meters by 12,192 meters duplicated four times. The compositions were applied with a counterbalanced CO2 sprayer, 20 GPA in an aqueous carrier. At maturity, the wheat grain was harvested with a combination of pods and the grain yield was recorded. The average yield values of the treated plants compared to the values obtained for the untreated plants were recorded and the data is presented in Table 15. Table 15 (Wheat) Regimen 1 gram 10 grams of ingredient of active ingredient / active hectare / hectare Performance 110% 107% Table 15 (Continued) Regimen 20 grams 50 grams of ingredient of active ingredient / active hectare / hectare Performance 113% 111% (The schemes express according to the application and each application is a total of four times) The results show an improvement in performance up to 13 percent of the untreated control. However, the results were not significant at p = 0.05.

EXAMPLE 7 The cherry tomatoes were grown in a greenhouse in large pots and treated with foliar spraying applications (20 GPA) of the ester. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl encapsulated with PVA prepared as described in Example 2 (540S). The plants were treated when the third bunch of fruit (younger at the time of application) was in the small button stage. The first and second clusters were flowering. The foliar applications were of regimes of 1, 3, 10, 30 and 100 grams per hectare in aqueous solutions. Fruits were harvested, during maturity were counted and fresh weights were recorded and compared with untreated plants. The results in relation to the untreated plants are presented in Table 16.

Table 16 5 (Tomatess) Regime 1 3 10 30 100 gram grams grams grams - • Performance of the third cluster 97% 121% 105% 85% 85% # of Fruit 127% 110% 103% 11% 79% Yield 5 of the second cluster 89% 109% 109% 93% 90% # of Fruit 92% 96% 98% 91% 95% Yield 0 of the first cluster 101% 86% 90% 94% 98% # of Fruit 97% 82% 100% 100% 105% Fresh weight improvement was obtained at 3 and 10 grams of the active ingredient per hectare and the second and third bunches and the number of fruits improved in the first bunch (30-100 grams per hectare) and the third cluster (1 gram per hectare). The best results were obtained with foliar application in the button or young bud stage at regimes equal to or less than 10 grams of the active ingredient per hectare. A similar trial carried out in the greenhouse on beefsteak tomatoes did not result in any improvement in fruit yields or fruit numbers.

EXAMPLE 8 Ester was applied. { [(isopropolidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl (Technical Quality, BASF Corporation) as a foliar spraying application to pepper plants (button stage) that were grown in the greenhouse. Aqueous ester solutions were applied. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl at regimes of 1, 3, 10, 30 and 100 grams of the active ingredient per hectare. Fruit was harvested at maturity, counted and fresh weights recorded. The results were calculated as the percentage of the untreated plants and are presented in Table 17.

TABLE 17 Regime (gram / 1 3 10 30 100 hectare) # Fruit 121% 115% 124% 112% 117% Yield 118% 110% 123% 107% 95% Improvements were obtained both in the number of fruits and the fresh weight yields, particularly at regimes of 10 grams of the active ingredient per hectare and lower (not significantly at p = 0.05).

EXAMPLE 9 The ester of. { [(isoprppiliden) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl (99 percent Technical Grade, BASF) and the encapsulated formulations (205S, 523S, 540S) prepared as described under Example 2, were applied in 4 to 6 foliar applications in sequence in field trials of three small plots in the established turfgrass (fescue, compressed poa and zoysia grass). Experiments were carried out in a randomized complete block with four duplicates. The treatments were applied as a foliar spraying application with a spray volume of approximately 373.60 liters per hectare in an aqueous dilution at rates of 1, 5, 10 and 20 grams of the active ingredient per hectare per application. After the final application, two ground cores of 5.08 centimeters of the first duplicate of each test were taken. The cores were washed and visually evaluated to determine increases in root mass. The visually evident increases in the root mass were observed in fescue in the treatments with the formulations 523S and 540S, in the poa compressed with technical quality (10 grams and less) and in zoysia (technical quality less than 10 grams per hectare and 523S formulations to all regimes). Additional controlled studies were carried out in the greenhouse on common agrostis and white granules that had been established and cut several times in 10.16 centimeter pots. The study doubled seven times. The PVA 523S formulation was applied to 1, 5, 10 and 20 grams of the active ingredient per hectare, in a treatment method, the compound was applied in an aqueous foliar spraying 24 hours before being cut and transplanted from the original container. In the second treatment method, the grass was cut and transplanted and then sprayed by an aqueous foliar application. In a third treatment method, the turf was cut and transplanted and treated with a volume of 50 milliliters of aqueous solution with the equivalent active ingredient as applied in the spraying applications. The transplanted grass was removed from the pots, washed and visual observations made. Dry root and shoot weights and measured root lengths were measured. The results for common agrostis are presented in Table 18.

Table 18 Regime 1 5 10 20 (gram / hectare) gram gram grams gram Dry weight of the root 205% 331% * 131% 280% * Root length 134% 153% * 144% * 123% Dry weight of the shoot 149 * 129 ^ 115 * 145 * All values in relation to the control were treated with equivalent water quantities. * represents significant value at p = 0.05.

The data shows a significant increase (p = 0.05) in the dry weight of the root and the length and dry weight of the shoot in the common agrostis when the drought method was used. The data also show a significant increase in the dry weight of the root and the length in the white granule with the application of drought (20 grams of the active ingredient per hectare) and an increase in the dry weight of the root with application before of cutting (1 gram of the active ingredient per hectare). For example, the dry weight of the treated turf shoot showed an increase relative to the untreated of 49 percent, 29 percent, 15 percent and 45 percent at 1, 5, 10 and 20 grams per hectare regimes. Of applications.

EXAMPLE 10 A composition containing the ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl (99 percent Technical Grade, BASF) in a solvent having an emulsifier system was then prepared. A C8 pyrrolidone solvent (AGSOLEX® 8, 1-octylpyrrolidone, ISP) was mixed with an emulsifier system containing a block copolymer (PLURAFAC® LF-700, BASF) and an emulsifier comprising a mixture of 80 percent ethoxylate of nonylphenol (MAKON®, Stepan Chemical) and 20 percent dioctyl sulfosuccinate (AERSOL® OT 100). The resulting solution was mixed until a homogeneous crystalline solution was formed. The ester of. { [) isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl (99 percent Technical Grade, BASF) to the crystalline solution and mixed until a homogeneous crystalline solution was formed. The resulting composition contained about 82.6 percent of C8 pyrrolidone, about 8.3 percent of a block copolymer emulsifier, about 4.1 percent emulsifier and about 5.0 percent of the ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl. This resulting composition was mixed with the plant growth regulator PIX® of mepiquat chloride (BASF Corporation) in such a way that the mepiquat chloride was applied to the cotton in field studies at the rate of 12 grams per hectare and the ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl content in the solvent with an emulsifier system was applied at 1 and 10 grams per hectare. The results are presented in Table 19.

Table 19 (Cotton) performance Regime (gram per hectare) 1 10 me Relative performance 103% 106% 102% (percentage compared to untreated)) Positive Performance Frequency 62% 62% 38% me = mepiquat chloride The results show that the treated plants had an increase of 3 percent and 6 percent in relation to the untreated plants at rates of 1 and 10 grams per hectare respectively - with a positive yield frequency of 62 percent.

EXAMPLE 11 Field studies were carried out with mepiquat chloride (PIX ® plant growth regulator) in combination with the ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl - in three formulations: 1) 99 percent Technical Quality, BASF Corporation; 2) encapsulated with PVA (540S); and 3) solvent containing an emulsifier system (as described in Example 10). Mepiquat chloride was applied at 12 grams per hectare for all applications. Plants treated with mepiquat chloride alone were also evaluated for their performance. The mean value for the mepiquat chloride samples was 103 percent in relation to the untreated ones. The mean values for all combinations (as a percentage of yield for plants treated with mepiquat chloride) were obtained for all trials and are summarized below in Table 20.

Table 20 Performance Rate Number of Frequency (gram / hectare) (percentage) comparisons of positives 0. 5 108 11 64í 1.0 104 75 63Í 10 104 83 55Í The results show that the average value of the plants treated with the combination had improvements of 8 percent, 4 percent and 4 percent at the 0.5, 1 and 10 gram regimes per hectare, respectively, when compared with plants treated with mepiquat chloride. When the trials included an untreated control, the combinations had improvements of 10 percent, 5 percent, and 6 percent when compared to the untreated controls. The mepiquat chloride applied alone resulted in an increase in the average yield of 3 percent relative to the untreated control when all the field trials carried out are summarized. The experiments were also carried out on cotton subjected to drought. The mean values for all combinations (as a percentage of plants treated with mepiquat chloride) were obtained for all trials and are summarized below in Table 21.

Table 21 Performance Rate Frequency Number (gram / hectare) (percentage) positive comparisons 0. 5 115 3 67% 1.0 113 14 86% 10 114 14 64% The results show that the average value of the plants treated with the combination had improvements of 15 percent, 13 percent and 14 percent at rates of 0.5, 1 and 10 grams per hectare, respectively, when compared with the plants treated with Mepiquat chloride Because plants treated with mepiquat chloride only showed an average (average) increase of 9 percent (80 percent positive response, average of seven trials) relative to those not treated, these results indicated an improvement of 6 percent. percent, 4 percent and 5 percent in relation to untreated plants at rates of 0.5, 1 and 10 grams per hectare, respectively. The invention has been described with reference to different specific modalities. However, many variations and modifications can be made as long as they remain within the scope and spirit of the invention

Claims (12)

CLAIMS:

1. A method for improving at least one growth factor in a plant comprising applying a substituted oxime-ether having the formula: wherein R 1 and R 2 independently of one another are alkyl of 1 carbon atom to 6 carbon atoms, n is 2 or 3 and R 3 is hydrogen or alkyl of 1 carbon atom to 6 carbon atoms to a plant at a low rate .

2. A method for improving at least one plant growth factor comprising applying a compound to a plant at a low rate wherein the compound is selected from the group consisting of [((isopropylidene) amino] oxy acetic acid and aminooxyacetic acid.

3. The method according to claim 1, wherein the oxime-ether is selected from the group consisting of ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl, ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (hexyloxy) -2-oxoethyl and ester of. { [(cyclohexylidene) -amino] oxy} -acetic acid-2- (isopropyloxy) -2-oxoethyl.

4. The method according to claim 1, wherein the oxime-ether comprises ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl. The method according to claim 1, wherein the regimen ranges from about 100 milligrams of the active ingredient per hectare to about 50 grams of the active ingredient per hectare. 6. The method according to claim 2, wherein the regimen ranges from about 100 milligrams of the active ingredient per hectare to about 50 grams of the active ingredient per hectare. The method according to claim 3, wherein the regimen ranges from about 100 milligrams of the active ingredient per hectare to about 50 grams of the active ingredient per hectare. The method according to claim 4, wherein the regimen ranges from about 100 milligrams of the active ingredient per hectare to about 50 grams of the active ingredient per hectare. The method according to claim 5, wherein the regimen ranges from about 500 milligrams of the active ingredient per hectare to about 10 grams of the active ingredient per hectare. The method according to claim 6, wherein the regimen ranges from about 500 milligrams of the active ingredient per hectare to about 10 grams of the active ingredient per hectare. The method according to claim 7, wherein the regimen ranges from about 500 milligrams of the active ingredient per hectare to about 10 grams of the active ingredient per hectare. The method according to claim 8, wherein the regimen ranges from about 500 milligrams of the active ingredient per hectare to about 10 grams of the active ingredient according to any of claims 1 to 12, wherein the plant is selected of the group consisting of a cotton plant, a soybean plant, a peanut plant, a pepper plant, a tomato plant, a wheat plant, a barley plant, a rice plant, a plant of apple, a citrus fruit plant, a grape plant or a canola plant. SUMMARY OF THE INVENTION The method of the invention provides improvement of a plant growth factor by spraying an ethylene inhibitor plant growth regulator, such as cotton or soybeans, at a plant at a low rate. Regulators of specific plant growth are included in the compounds covered by the general formula: wherein R 1 and R 2 independently of one another are alkyl of 1 carbon atom to 6 carbon atoms, n is 2 or 3 and R 3 is hydrogen or alkyl of 1 carbon atom to 6 carbon atoms. The specific compounds employed by the method of the invention include ester. { [(isopropylidene) -amino] oxy} -acetic acid-2- (methoxy) -2-oxoethyl, ester of. { [(isopropylidene) -amino] oxy} -acetic acid-2- (hexyloxy) -2-oxoethyl, ester of . { [(cyclohexylidene) -amino] oxy} -acetic acid-2- (isopropyloxy) -2-oxoethyl, [((isopropylidene) amino] oxyacetic acid and aminooxyacetic acid.