MXPA97008252A - Use of a n-arilpirazol or n-heteroarylpirazol compound to regulate plan growth - Google Patents

Abstract

The present invention relates to a method for regulating the growth of plants, characterized in that it comprises applying to the plants, the seeds from which they grow, or the site in which they grow, an effective and non-phytotoxic amount, which regulates the growth of the plant, of a compound that has the formula

Description

USE OF A COMPOSITE OF N-ARILPIRAZOL OR N-HETEROARILPIRAZOL TO REGULATE PLANT GROWTH DESCRIPTION OF THE INVENTION The present invention relates to a new method for the treatment of plants, to induce responses that regulate growth. The term "peer method regulating plant growth" or the term "plant regulation process", or the use of the words "growth regulation", or other terms that use the word "regular" as used herein Specification, are related to a variety of responses of plants that try to improve some characteristics of the plant, distinguishing itself from the pesticidal action, the intention of which is to destroy or atrophy the growth of a plant or a living being. For this reason, the compounds used in the practice of this invention are used in amounts that are non-phytotoxic with respect to the plant being treated. The regulation of plant growth is a desirable way to improve plants and cultivate them, in order to obtain better plants and better conditions of agricultural practice. The present invention provides a method for regulating plant growth, which comprises applying to REF: 25959 the plants, the seeds from which they grow, or the place where they grow, a non-phytotoxic, effective amount that regulates the growth of the plants, of a compound that has the formula: (D where: Ri is CN or methyl; R3 is alkyl or haloalkyl; R is selected from the group comprising a hydrogen atom, a halogen atom, and a radical which may be -NR5R6, C (0) 0R7, -S (0) mR7, alkyl, haloalkyl, -OR8, or -N = N (R9) (Rio); R is preferably an amino group, which is unsubstituted, or bears one or two substituents selected from the group consisting of alkyl, haloalkyl, acyl or alkoxycarbonyl; R5 and R6 are independently selected from a hydrogen atom, alkyl, haloalkyl, -C (O) alkyl, -S (0) CCF3; or R5 and R5 together form a divalent radical, which may be interrupted by one or more heteroatoms; R7 is selected from alkyl or haloalkyl; R8 is selected from alkyl, haloalkyl or the hydrogen atom; R9 is selected from the hydrogen atom and alkyl; Ro is selected from phenyl or heteroaryl, which is optionally substituted by one or more of hydroxy, a halogen atom, -O-alkyl, -S-alkyl, cyano, or alkyl, or combinations thereof; X is selected from the nitrogen atom and the radical C-R12; Rp and Ri2 are independently selected from a halogen atom or the hydrogen atom; R13 is selected from a halogen atom, haloalkyl, haloalkoxy, -S (0) qCF3, -SF5 preferably from a halogen atom, haloalkyl, haloalkoxy, -SF5; m, n, q, r are independently selected from 0, 1 and 2; provided that when Ri is methyl, R3 is haloalkyl, R4 is NH2, Rp is Cl, Ra3 is CF3, and X is N. The alkyl and alkoxy groups of the formula (I) are preferably lower alkyl and alkoxy groups, that is, radicals having from one to four carbon atoms. The haloalkyl and haloalkoxy groups also preferably have from one to four carbon atoms. The groups haloalkyl and haloalkoxy can carry one or more halogen atoms; Preferred groups of this type include -CF3 and -OCF3. A preferred group of 1-phenylpyrazoles that regulate the growth of plants for use in the present invention are those of formula (I) wherein: R? and R6 are independently selected from the hydrogen atom, alkyl, haloalkyl, -C (O) alkyl, C (0) 0R7, * and / or R13 is selected from a hydrogen atom, haloalkyl, haloalkoxy, or -SF5. A particularly preferred group of 1-phenylpyrazoles that regulate the growth of plants for use in the present invention are those of formula (I) wherein: Ri is CN; R 4 is -NR 5 R 6; R5 and R6 are independently selected from the hydrogen atom, alkyl, haloalkyl, -C (O) alkyl, C (0) 0R7; X is C-R? 2; R13 is selected from a hydrogen atom, haloalkyl, haloalkoxy, or -SF5.

Specific pyrazole derivatives usable in the method for regulating the growth of plants falling within the scope of the present invention include 5-amino-3-cyano-1- (2,6-dichloro-4-trifluoromethylphenyl) -4 -tri-fluoromethylsulfinylpyrazole. This plant growth regulator especially preferred for use in the present invention is hereafter referred to as compound A. According to another aspect of the present invention, a method of regulating the growth of a plant is provided, at a site where there are no insects, or in which it is expected that they are not, or are not expected to pass, or pass through, or inhabit, or visit or fly, the method is characterized by comprising the application to the same or the seed of the plant of a non-phytotoxic, effective amount, which regulates the growth of the plant, of a compound of formula (I). Another aspect of the invention is a method for regulating the growth of plants selected from the group consisting of rice, corn, cereal, vegetable and soybean and turf plants, the method comprising applying to the plants, the seeds from which they grow, or to the place where they grow, a non-phytotoxic, effective amount that regulates the growth of the plants, of a compound that has the formula (I).

Another aspect of the invention is a method for regulating the growth of soybean plants, characterized in that it comprises applying to the seeds from which the soybean plants grow, before seeding the seeds, a non-phytoxic, effective amount, which regulates the growth of the plants, of a compound having the formula (I). Another aspect of the invention is a method for treating plants that need growth regulation, characterized in that it comprises applying to the plants, the seeds from which they grow, or the site in which they grow, a non-phytotoxic, effective amount, which regulates the growth of plants, of a compound having the formula (I). This need for growth regulation is particularly great when the plants or seeds thereof are weak or brittle, or subject to tension, or are not in favorable growing conditions for plant growth. The preparation of the compounds of formula (I) can be carried out according to any process described in International Patent Publications Nos. WO 37/03781, WO 93/06089 and WO 94/21606, as well as in the Patent Publications. European Nos. 0295117, 0403300, 0385809, and 0679650, German Patent Publication 19511269 and the Patents of the United States of America 5,232,940 and 5,236,938. The 1-phenylpyrazoles of formula (I) used in the method of the present invention fall within a larger group of compounds, which have been previously described as insecticides. It has been found that, surprisingly, the compounds of formula (I), and more especially compound (A), exhibit a wide variety of growth regulating properties in plants, depending on the concentration used, the formulation employed and the type of species of treated plant. By virtue of the practice of the present invention, a wide variety of responses can be induced in the growth of plants, including the following: a. more developed root system b. increase in shoot production c. increase in the height of the plant d. Larger limbo e. minus dead basal leaves f. Stronger shoots g. leaf color more green h. Fewer fertilizers needed i. less seeds needed j. more productive shoots k. less non-productive tertiary shoots 1. earlier flowering m. maturity of the earliest grain n. enos bedded plant (plantation) or. larger panicles p. Increased growth of the stem q. improved vigor of the plant r. earlier germination s. more fruits, and better yield (weight) of fruit. It is proposed that as used in the present specification, the term "method to regulate the growth of the plant" or "method to regulate the growth of plants" means the realization of any of the nineteen categories mentioned above of response, or any other modification of the plant, seed, fruit or vegetable (whether the fruit or vegetable is not harvested, or harvested), provided that the net result is to increase growth or to benefit any property of the plant, seed, fruit or vegetable, distinguishing itself from any pesticide action (unless the present invention is practiced in conjunction with, or in the presence of a pesticide, for example a herbicide). The term "fruit" as used in the present specification is to be understood as meaning anything of economic value that is produced by the plant. Suitable formulations for compositions that regulate plant growth are known. A description of suitable formulations that can be used in the method of the invention can be found in the international patent publications WO 87/3781, 93/6089, 94/21606, as well as in the European Patent Application 295117 and the Patent. No. 5232940. The formulations described in the prior art are proposed primarily for insecticidal purposes. The formulations or compositions for uses in plant growth regulation can be made in a similar manner, by adapting the ingredients, if necessary, to make them more suitable for the plant or soil to which the application is to be made. The 1-phenylpyrazoles of formula (I) can be applied for purposes of regulating the growth of plants to the foliage of plants and / or to the soil in which the plants are growing. Soil applications are often in the form of granules, which are usually applied in sufficient quantity to provide a proportion from about 0.005 kg / ha to about 0.5 kg / ha of active ingredient, preferably between 0.01 and 0.2 kg / ha. A preferred embodiment of the invention is a method for regulating the growth of plants, which comprises applying to the seeds from which the plant grows, before sowing the seeds, a non-phytotoxic, effective amount that regulates the growth of the plants. plants, of a compound having the formula (I). The seed can be treated, especially by coating or embedding or impregnation or wetting or immersion in liquid or paste formulations, which are known per se, and are subsequently dried. Seeds comprising from 2 to 1000 grams per 46 kilograms (one quintal) of a compound of formula (I), preferably from 5 to 800 g / q, more preferably from 5 to 250 g / q are particularly suitable for this purpose. Advantageously, the compounds of formula (I) can also be formulated as flowable compositions, wettable powders, microemulsions and the like, which lend themselves to application to the soil, water and / or foliage, and provide the growth regulating action requirement of the plant. Such formulations include the compounds of the invention mixed with solid diluents or inert liquids, acceptable from the agricultural point of view.

The formulations may comprise other active ingredients, in addition to the compound of formula (I). For example, mixtures with an active ingredient can be used from the fungal view point. Wettable powders and concentrated granular formulations for use in the method of the invention can be prepared by grinding together a 1-phenylpyrazole compound of formula (I), with about 1% to 20% by weight of a solid anionic surfactant. A suitable anionic surfactant is a dioctyl ester of suifosuccinic sodium acid. About 85% to 95%, by weight, of an inert solid diluent, such as montmorillonite, attapuigite, chalk, talc, kaolin, diatomaceous earth, limestone, silicates or the like is also included in such formulations, as well as other adjuvants , co or ios previously indicated. In addition to the formulations of granules and wettable powders described above, the fluid formulations can be used, since they are readily dispersible in water, and can be applied to the appropriate site, where the plant growth regulating action is required. The pyrazole derivatives used in the method of the present invention have a low solubility in water, but can be used at low doses. Thus, they can be applied to the plants in aqueous solutions or emulsions or, preferably, suspensions comprising water and, optionally, other adjuvants. Partial aqueous media include those formed of water and, for example, acetone or methyl ethyl ketone. Any liquid medium can be used, provided it is not toxic to the plant, and preferably not to the environment. When any particular pyrazole derivative is less soluble in water, it can be solubilized by the use of co-solvents or wetting agents, or it can be suspended by means of dispersing agents, which can be used simultaneously with for example surfactants and diluents. Other means, including solids, such as talc, will occur to those skilled in the art. The compounds used in the process of this invention can be absorbed onto solid carriers, such as vermiculite, clay, talc and the like, for application via a granular carrier. The application of diluted or solid aqueous formulations is achieved using conventional equipment, which is well known in the art. As will be demonstrated in connection with certain examples in this specification, the compounds used in the process of the present invention have been effective in regulating the growth and development of plants, in connection with a wide variety of plant species in various concentrations of pyrazole active compounds. The precise amount of pyrazole compound to be used will depend, inter alia, on the particular species of plant being treated. A suitable dose can be determined by the man skilled in the art by routine experimentation. The response of the plant will depend on the total amount of compound used, as well as on the particular species of plant that is being treated. Of course, the amount of pyrazole compound must be non-phytotoxic with respect to the plant being treated. Although the preferred method of application of the compounds used in the process of this invention is directly to the foliage and stems of plants, the compounds can be applied to the soil in which the plants are growing. Such compounds will be absorbed by the roots, to a degree sufficient to result in plant responses according to the teachings of this invention. The process of the present invention is often preferably carried out on growing plants, as is disclosed in many of the examples in this specification. However, the process of the present invention is advantageously carried out as a treatment for seeds, for example, of rice seeds, lettuce seeds, oat seeds and soybeans. The following examples are illustrative of methods of regulating the growth of plants according to the invention, but should not be understood as limiting the invention, since the modifications in materials and methods will be apparent to the skilled worker. All measurements of the effects of plant growth regulation were determined using seeds and / or untreated plants as controls. EXAMPLE 1 Rice seeds were treated by mixing the seeds with a suspension concentrate containing 5% w / w of compound A. This mixing resulted in a coated seed, which was immediately seeded over an area of 1000 nr, in order to have 30 g / ha of active ingredient. The results were observed from the emergence of the seedling to the harvest. Some insects were present and were killed. The results were observed 35 days after sowing. An increase of 5.4% in yield was observed, with the following regulatory effects of plant growth: greener plants, taller plants, fewer dead basal leaves, larger limbs, flowering 2 days earlier. EXAMPLE 2 Example 1 was repeated. The results were observed 60 days after sowing. An increase of 7 ° or in the yield was observed with the following effects of regulation of the growth of the plants; greener plants, taller plants, fewer dead basal leaves, larger limbs, flowering 2 days earlier, larger panicules, brighter grain color. EXAMPLE 3 Example 1 was repeated, except that 40 g / ha of active ingredient was applied. The same results were obtained, but also stronger shoots, as well as less plant bedding. EXAMPLE 4 Example 1 was repeated, except that 50 g / ha of active ingredient was applied. The same results were obtained, but also an increase of 15% of shoots grown, as well as an increase of 9.5% yield.

EXAMPLE 5 Rice seeds were sown, and the seed bed (acid sulfate soil) was treated (soil treatment) by rolling it with a suspension concentrate containing 5% w / w of compound A. After treatment, transplantation of rice was done as usual. Treatment of the seed bed was done 24 days before the transplant. The following effects of regulation of the growth of the plants were observed: stronger seedlings, flowering 6 days earlier, 25% increase in shoots, harvest 6 days earlier, 100% increase in yield. EXAMPLE 6 Rice seeds were sown, and the flooded bed of the seeds was treated (soil treatment) by spraying granules containing 0.3% w / w of compound A on it. After the treatment, the rice transplant was done as usual. Treatment of the seed bed was done 11 days before the transplant. The following effects of regulation of the growth of the plants were observed: stronger seedlings, 50% increase in shoots, fertilizers reduced by. 40 kg of urea and 50 kg / ha of superphosphate, and 7% increase in yield.

EXAMPLE 7 Corn seeds were planted in 3.5 liter pots (six plants per pot). Immediately after sowing, granules containing compound A were sprayed on the soil. The granules contained 1.5% w / w of active ingredient, and were sprayed in order to have a dose of 120 g / ha of active ingredient on the soil. The plants were irrigated properly. One month and one week later, the weight of the dried roots was measured. The weight of the roots is about 42 g for the treated pots, and 30 g for the untreated pots. EXAMPLE 8 Rice seeds were germinated 48 hours in water at 30 ° C, and then planted in pots. After the emergence of the seedlings, granules containing 0.3% w / w of compound A, in proportions of 200 and 100 g / ha, were applied to the soil. No phytotoxicity was observed with any of the formulations or proportions. Periodically, groups of pots were harvested, and the dry weights of the roots were determined. Pyrazole treatments increased the mass of dried roots per pot, by an average of 36% over that of untreated seedlings 28 days after treatment.

EXAMPLE 9 Soybean seed was treated with a mixture of an insecticidally active compound together with an active compound from the fungicidal point of view. The soybean was planted at 60 kg / ha in a lot that had, after growing, 1000 plants per batch. The seeds germinated and the plants were cultivated, until the time of harvest, and observations were made throughout that time. The results in the following Table clearly show that the growth regulation activity of the plants of compound A is not simply attributable to their insecticidal activity. Other comparable insecticides do not produce regulation of plant growth, while the results obtained with compound A clearly show a regulating effect of plant growth. The following active ingredients and doses were applied: The following observations were made: the control of the bean fly was greater than 95% with both, compound A and Carbosulfan. The growth of the plant with compound A was much faster during the first month after sowing. The plants treated with compound A were taller and healthier, the leaves were wider, greener and brighter, the branches were stronger, and there were more branches, and the development of plant foliage was faster than in the other treatments, so there was less weed. The number of pods / plant was 24 to 37% higher with compound A than with Carbosulfan. The yield was much higher when compound A was applied. Both the yield and the average number of pods per plant they were also higher using compound A than when thiodicarb and methomyl were used. EXAMPLE 10 Rice seeds were treated with a formulation of compound A, in a proportion of 40 g / hectare of planted field, in a proportion of 150 kg / hectare, and covered with a thin layer of soil. After this, the seed was allowed to germinate, and the plants were grown to maturity, and the rice crop was harvested. An increase in yield of 660 kg / hectare was found above the normal conditions (seeded seeds not treated with compound A). The amount of fertilizer savings were as follows: Nitrogen - 18 kg / hectare, this is 18% less than the standard protocol; Phosphates - 7 kg / hectare, this is 16% less than the standard protocol. When the experimental conditions of examples 1 to 10 were repeated with places where insects were not expected, or that passed, which inhabited, visited or flew through them, the same results were obtained: the effects of regulation of the growth of the plant of compound A were the same as with the conditions in which the insects were present in the place. The insects, if there was some, were eliminated by the application of compound A. When no insects were expected, there was no reason to apply compound A as an insecticidally active ingredient or composition. The application of compound A for purposes of regulating the growth of the plant was producing the effects indicated in examples 1 to 10. While the invention has been described in terms of several preferred embodiments, the skilled artisan will appreciate that various modifications can be made. , substitutions, omissions and changes without departing from the spirit of the same. Accordingly, it is proposed that the scope of the present invention be limited only by the scope of the following claims, including the equivalents thereof.

It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Having described the invention as above, property is claimed as contained in the following:

Claims (15)

1. A method for regulating the growth of plants, characterized in that it comprises applying to the plants, the seeds from which they grow, or the site in which they grow, an effective and non-phytotoxic quantity, which regulates the growth of plants. the plant, of a compound that has the formula: (D where: R: is CN or methyl;: is S (0) -R;; R3 is alkyl or haloalkyl, is selected from the group comprising a hydrogen atom, a halogen atom, and a radical which can be - R, R, C (0) 0R7, -S (0) -R-, alkyl, haloalkyl, -0R, or R = and R are independently selected from a hydrogen atom, alkyl, haloalkyl, -C (O) alkyl, -S (0) rCF3; or R; and R¿ form, together, a divalent radical, which may be interrupted by one or more heteroatoms; R- is selected from alkyl or haloalkyl; RA is selected from alkyl, haloalkyl or the hydrogen atom; R? it is selected from the hydrogen atom and alkyl; R :: is selected from phenyl or heteroaryl, which is optionally substituted by one or more of hydroxy, a halogen atom, -O-alkyl, -S-alkyl, cyano, or alkyl, or combinations thereof; X is selected from the nitrogen atom and the radical C-R? 2; R-: and R-.z are independently selected from a halogen atom or the hydrogen atom; :? is selected from a halogen atom, haloalkyl, haloalkoxy, -S (0) qCF3, -SF5; m, n, q, r are independently selected from 0, 1 and 2; provided that when R. is methyl, R3 is haloalkyl, R4 is NH :, R- .: is Cl, 13 is CF3, and X is N.

2. A method to regulate the growth of a plant in a place where there are no insects, or in which it is expected that they are not, or are not expected to pass, or pass through, or inhabit, or visit or fly, the method is characterized by comprising the application to the same or the seed of the plant of a quantity not phytotoxic, effective, which regulates the growth of the plant, of a compound of formula: (D wherein all the substituents are defined as in claim 1.

3. A method for regulating the growth of plants, characterized in that it comprises applying to the seeds from which the plant grows, before planting the seeds, an amount non-phytotoxic, effective, which regulates the growth of plants, of a compound that has the formula: (D wherein all substituents are defined as in claim 1.

4. A method for regulating the growth of plants selected from the group consisting of rice, corn, cereal, vegetable and soybean and turf plants, the method is characterized in that it comprises applying to the plants, to the seeds from which they grow, or to the site in which they grow, a non-phytotoxic, effective amount that regulates the growth of the plants, of a compound that has the formula: (D wherein all the substituents are defined as in claim 1.

5. A method for regulating the growth of soybean plants, characterized in that it comprises applying to the seeds from which the soybean plants grow, a non-phytotoxic amount. , effective, which regulates the growth of plants, of a compound that has the formula: (I) wherein all substituents are defined as in claim 1.

6. A method for treating plants that need growth regulation, characterized by comprising applying to the plants, the seeds from which they grow, or to the site in which they grow, a non-phytotoxic, effective amount that regulates the growth of plants, of a compound that has the formula: (D wherein all substituents are defined as in claim 1.

7. A method according to any of the preceding claims, characterized in that: R 4 is -NR 5 R 6; and / or R; and R6 are independently selected from the hydrogen atom, alkyl, haloalkyl, -C (O) alkyl, C (0) 0R7; I R: 3 is selected from a hydrogen atom, haloalkyl, haloalkoxy, or -SF5.

8. A method according to any of the preceding claims, characterized in that: Rx is CN; R "and R6 are independently selected from the hydrogen atom, alkyl, haloalkyl, -C (O) alkyl, C (0) 0R7; R-.3 is selected from a hydrogen atom, haloalkyl, haloalkoxy, or -SF5.

9. A method according to any of the preceding claims, characterized in that the compound of formula (I) is 5-amino-3-cyano-1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylsulfinylpyrazole.

10. A method according to any of the preceding claims, characterized in that the amount regulating the growth of the plant of the compound of formula (I) applied is sufficient to provide at least one effect that regulates the growth of the plant, selected from the group consisting of: a. more developed root system b. increase in shoot production c. increase in the height of the plant d. Larger limbo e. minus dead basal leaves f. Stronger shoots g. leaf color more green h. Fewer fertilizers needed i. less seeds needed j. more productive shoots k. less non-productive tertiary shoots 1. earlier flowering m. maturity of the earliest grain n. less bedding of the plant (plantation) or. larger panicles p. Increased growth of the stem q. improved vigor of the plant r. earlier germination s. more fruits, and better yield (weight) of fruit.

11. A method according to any of the preceding claims, characterized in that a compound of formula (I) is applied to the plants, or to the site in which they grow, in the form of granules, in an application rate from 0.005 kg / ha to 0.5 kg / ha.

12. A method according to any of the preceding claims, characterized in that a compound of formula (I) is applied to the plants, or to the site in which they grow, in the form of granules, in an application rate from 0.01 kg. / ha at 0.2 kg / ha.

13. A method according to any of the preceding claims, characterized in that a compound of formula (I) is applied to the seeds, in an application rate from 2 to 1000 grams per quintal of seeds. A method according to any of the preceding claims, characterized in that a compound of formula (I) is applied to the seeds, in an application rate from 5 to 800 grams per quintal of seeds. 15. A method according to any of the preceding claims, characterized in that a compound of formula (I) is applied to the seeds, in an application rate from 5 to 250 grams per quintal of seeds.