JP6842082B2 - Plant growth regulator - Google Patents

Description

The present invention relates to plant growth regulators.

In the agricultural field, controlling plant growth is an important technique for improving productivity. Currently, various types of plant growth regulators for the purpose of controlling plant growth have been put into practical use, and plant growth regulators contribute to improving the yield of crops and the quality of products. Plant growth regulators include both those that promote and suppress the growth of any tissue in the plant. Therefore, a wide range of materials such as a rooting promoter, a fruit set promoter, a fruit hypertrophy promoter, a fruit tree plucking agent, a fruit coloring promoter, a dwarfing agent, and a herbicide are included as plant growth regulators.

In the tissue of plants, roots play very important roles such as plant colonization, water absorption, nutrient absorption, and prevention of lodging, so it is important to promote their development.
The roots of plants are composed of taproots, lateral roots, and adventitious roots, which are collectively called the root system. The taproot is already developed at the seed stage and grows at the same time as germination. Therefore, if the growth of taproots can be promoted, the absorption of water and nutrients in the soil can be promoted from the initial stage, the initial growth can be promoted, and the initial drought stress tolerance can be imparted. Lateral roots differentiate and develop from taproot. Therefore, if the growth of lateral roots can be promoted, the surface area of the roots can be dramatically increased, the absorption of water and nutrients in the soil is promoted, the overall growth can be promoted, and the resistance to drought stress is imparted. can do. Adventitious roots differentiate and develop from tissues other than roots such as stems and leaves. For this reason, roots generated from cultured plant cells and roots generated from above-ground tissue sections such as cuttings and cuttings are classified as adventitious roots, and in order to promote so-called vegetative propagation efficiently, the development of adventitious roots should be promoted. Has become an important industrial technology. In monocotyledonous plants such as grasses, the growth of radicles stops shortly after germination, and most roots except seed roots are adventitious roots that develop from stems and are also called coronary roots. Promoting the development of these adventitious roots is important for ensuring the stable growth of grasses. Adventitious root formation is especially important for the growth and lodging prevention of major crops such as rice, wheat and corn.

A plant growth regulator having an action of promoting the development of these roots is desired. However, the number of plant growth regulators that promote rooting is small and the effect is not sufficient, and the conventional substances that promote root development often have an unfavorable effect. For example, auxin compounds widely used as rooting agents at present are toxic to plants depending on the type and condition of the plant and the concentration to be applied, and exert unfavorable effects such as chlorosis of stems and leaves and death. Sometimes.
The following can be exemplified as the prior art.
WO2011 / 136285 (Patent Document 1) describes that a compound having a dichlorophenyl group, a difluorophenyl group, or the like causes adventitious roots of eucalyptus.
Further, Japanese Patent Application Laid-Open No. 5-260869 (Patent Document 2) describes that adventitious roots can be induced in sweet potato stems by using auxin and α-naphthalene acetic acid in combination.
Further, Japanese Patent Application Laid-Open No. 5-49484 (Patent Document 3) describes a technique for inducing adventitious roots by culturing lemon balm callus in a medium supplemented with auxin.
In addition, 4-chloro is used as a fruit set promoting action of auxin, a fruit setting promoting agent utilizing the fruit hypertrophy action, a fruit hypertrophy promoting agent, a fruit tree picking agent utilizing the ethylene generation promoting action of auxin, and a fruit coloring promoting agent. Phenoxyacetic acid, dichloroprop, ethylene and the like have been put into practical use. 2,4-D, 2,4-PA, MCPA, etc. have also been put into practical use as herbicides for broad-leaved plants utilizing the disturbing action of auxin's endogenous hormone. However, these plant growth regulators are also small in number, have insufficient effects, and often have more unfavorable effects.
As described above, among the plant hormones having a rooting promoting action, those having a rooting promoting action are auxins. A typical natural auxin is indole-3-acetic acid. Indole-3-butyric acid has also been put into practical use as a rooting promoter. On the other hand, it has been clarified that indole-3-carboxylic acid is contained in the plant body as an analog compound (Non-Patent Document 1), but it is said that there is no auxin activity including rooting promoting activity (non-patent document 1). Patent Document 2). That is, among the compounds having an indole skeleton, some compounds in which the carboxyalkyl group is substituted at the 3-position have auxin activity, but the compounds in which the carboxyl group is directly substituted at the 3-position have a rooting promoting action. Has been thought not to be recognized. Similarly, no rooting promoting activity was observed for the compound in which the carboxyl group was substituted at the 7-position.

International Publication No. 2011/136285 Pamphlet Japanese Unexamined Patent Publication No. 05-260869 Japanese Unexamined Patent Publication No. 05-049484

Bottcher et al. 2014. The biosynthetic pathway of indole-3-carbaldehyde and indole-3-carboxylic acid derivatives in arabidopsis. Plant Physiol. 165: 841-853. Borgati and Boaventura 2011. Effects of indole amides on lettuce and onion germination and growth. Z. Naturforsch C. 66: 485-490.

An object of the present invention is to provide a novel plant growth regulator.

As a result of diligent research to solve the above problems, the present inventors have found that an indole-7-carboxylic acid derivative promotes rooting and further promotes root system development, leading to the completion of the present invention. It was.

That is, the present invention has the following configuration.
1. 1. A plant growth regulator containing a compound represented by the general formula 1 or a salt or ester thereof as an active ingredient.

However, R1 to R3 of the general formula 1 have any of the following structures.
R1 = hydrogen atom, halogen atom, hydroxyl group, alkyl group, or alkoxy group R2 = hydrogen atom, halogen atom, hydroxyl group, alkyl group, or alkoxy group R3 = hydroxy group, alkoxy group, or amino group 2. The plant growth regulator according to 1, wherein R1 is a hydrogen atom, R2 is a halogen atom, and R3 is a hydrogen atom.
3. 3. The plant growth regulator according to 2, wherein R2 is either a chlorine or a bromine atom.
4. The plant growth regulator according to 1, wherein R1 and R2 are hydrogen atoms and R3 is an alkoxy group.
5. The plant growth regulator according to 4, wherein the alkoxy group is a methoxy group.
6. A plant growth regulator containing any one or more of indole-7-carboxylic acid, 5-chloroindole-7-carboxylic acid, 5-bromoindole-7-carboxylic acid, and methyl indole-7-carboxylate.
A rooting agent comprising the plant growth regulator according to any one of 7.1 to 6.
A fertilizer containing the plant growth regulator according to any one of 8.1 to 6.
A pesticide containing the plant growth regulator according to any one of 9.1 to 6.

The present invention provides a novel plant growth regulator. The plant growth regulator of the present invention has high rooting promoting activity and does not have side effects such as chlorosis of stems and leaves. Further, the plant growth regulator of the present invention is useful as a rooting promoter at the time of cutting, raising seedlings, and transplanting. In addition, in order to promote root system development, the absorption efficiency of fertilizer components is improved, the growth of plants is promoted, and the yield is increased.

The present invention is a plant growth regulator containing a compound represented by the general formula 1 or a salt or ester thereof as an active ingredient.

However, R1 to R3 of the general formula 1 have any of the following structures.
R1 = hydrogen atom, halogen atom, hydroxyl group, alkyl group, or alkoxy group R2 = hydrogen atom, halogen atom, hydroxyl group, alkyl group, or alkoxy group R3 = hydroxy group, alkoxy group, or amino group

The above compound is a compound known as indole-7-carboxylic acid, a derivative thereof, or a salt thereof.
Substituents R1 and R2 are a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, and a hydroxyl group. As the halogen atom, a chlorine atom, a bromine atom and an iodine atom are preferable.
Examples of the lower alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an i-pentyl group and an i-hexyl group. Alkyl groups 1 to 6 can be mentioned. A methyl group is particularly preferable. The lower alkoxy group includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group and an i-pentyloxy group. An alkoxy group having 1 to 6 carbon atoms such as a group and an i-hexyloxy group is preferable. A methoxy group is particularly preferable.

Examples of the salt of the compound represented by the general formula 1 include alkali metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as calcium salt and magnesium salt, inorganic base salts such as ammonium salt, triethylamine salt and pyridine. Examples thereof include salts with organic base salts such as salts, picolin salts, ethanolamine salts, triethanolamine salts, dicyclohexylamine salts, and organic amine salts of N, N'-dibenzylethylenediamine salts.
In addition, salts such as inorganic acid salts such as hydrochlorides, sulfates and nitrates, and organic acid salts such as nitates, acetates, propionates, butyrates and lactates can be mentioned.

Examples of the ester of the compound represented by the general formula 1 include lower alkyl esters.

For the synthesis of the compound represented by the general formula 1, methyl anthranilate having an arbitrary substituent at the 5-position is used as a raw material as a method for synthesizing the indole-7-carboxylic acid having an arbitrary substituent at the 5-position (R2). Can be synthesized by a known method disclosed in US Pat. No. 7,259,183 or the like. The main synthetic reaction proceeds with the following chemical reaction.

式中、Ｒは任意の置換基を表す。

In the formula, R represents any substituent.

That is, it is synthesized by the following steps.
The compound represented by the formula (I), which is methyl anthranilate having an arbitrary substituent at the 5-position, is dissolved in acetic acid, mixed with N-iodosuccinimide, and iodinated by stirring at room temperature. The compound represented by the formula (II) can be obtained. At this time, the amount of acetic acid dissolved with respect to the mass of the anthranilic acid derivative is preferably 300 to 1000% by mass, and the amount of N-iodosuccinimide added is preferably 100 to 150 mol%. After the reaction, in order to collect the purified product from the reaction solution, the reaction solution may be neutralized by adding a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained compound represented by the formula (II) is dissolved in a base such as triethylamine, and a palladium catalyst such as bis (triphenylphosphine) palladium (II) dichloride, a copper catalyst such as copper (I) iodide, and trimethylsilylacetylene are used. And are mixed and stirred at room temperature to obtain the compound represented by the formula (III). At this time, the amount of trimethylsilylacetylene added to the compound represented by the formula (III) is 100 to 150% by molar mass, and the amount of bis (triphenylphosphine) palladium (II) dichloride and copper (I) iodide added is 2 to 2. It is preferably 10% molar mass. After the reaction, in order to collect the purified product from the reaction solution, the reaction solution may be diluted with dichloromethane, washed with water and saturated sodium chloride, and then the solvent may be distilled off. The compound represented by the formula (III) is dissolved in N-methyl-2-pyrrolidone in a mother liquor in which a base such as potassium tert-butoxide is mixed with N-methyl-2-pyrrolidone, added dropwise, and stirred. The compound represented by (IV) can be obtained. At this time, the molar mass of potassium tert-butoxide added to the compound represented by the formula (III) is preferably 200 to 300%. The amount of N-methyl-2-pyrrolidone dissolved is preferably 2000 to 4000% by mass with respect to the compound represented by the formula (III). After the reaction, in order to collect the purified product from the reaction solution, the residue obtained by extracting with diethyl ether, washing with water and saturated aqueous sodium chloride solution, and distilling off the solvent is purified by silica gel column chromatography. do it. The target compound represented by the formula (V) can be obtained by dissolving the compound represented by the formula (IV) in a mixture of a base and ethanol such as an aqueous sodium hydroxide solution and stirring at 40 ° C. At this time, the compound represented by the formula (IV) is preferably 0.1 to 5% by mass. After the reaction, in order to collect the purified product from the reaction solution, the pH of the reaction solution is acidified with hydrochloric acid, sodium chloride is added to a saturated state, and the mixture is extracted with ethyl acetate. Impurities can be removed by distilling off ethyl acetate, dissolving it in ethyl acetate, and adding activated carbon. The purified product can be further purified by a recrystallization method.
In addition to the above reaction steps, it can be synthesized by a known method disclosed in US Pat. No. 7,259,183, Patent No. 4870171, US Pat. No. 8063071, and the like.

Next, a substitution reaction for substituting R3 with an alkyl group will be described as an example of the substitution reaction for R1 to R3 of the compound of the general formula 1.
R3 is replaced with an alkyl group by heating and refluxing indolu-7-carboxylic acid as a raw material in an alcohol such as methanol, ethanol or propanol in the presence of an acid catalyst such as sulfuric acid or p-toluenesulfonic acid. Obtain the compound. At this time, the indolecarboxylic acid derivative is preferably 1 to 20% by mass, particularly preferably 5 to 10% by mass.
Further, a compound in which R3 is substituted with a methyl group can be obtained by reacting with an indolecarboxylic acid derivative as a raw material in methanol in the presence of a methyl esterifying agent such as trimethylsilyldiazomethane.
After the reaction, in order to collect the product from the reaction solution, the reaction solvent is distilled off, a product-soluble organic solvent that is not mixed with water and water are added, the pH of the aqueous phase is adjusted appropriately, and the solvent is extracted to perform organic. After recovering the solvent layer, it is dried, the organic solvent is distilled off, and then it may be recrystallized from a single solvent or a mixed solvent, if necessary. Further, if necessary, it may be isolated by a separation means such as high performance liquid chromatography (HPLC).
Substitution reactions other than the above can be easily carried out by known chemical reactions.
These compounds are preferably water-soluble, but in the case of water-insoluble compounds, they can be used in the form of being dispersed in water.

The names and general formulas of typical compounds useful as plant growth regulators in the present invention are illustrated below. Naturally, the present invention is not limited to these compounds.

Compound 1
Indole-7-carboxylic acid

Compound 2
5-Chloroindole-7-carboxylic acid

Compound 3
5-Bromoindole-7-carboxylic acid

Compound 4
Indole-7-carboxylic acid methyl ester

The plant growth regulator of the present invention can also be used in combination of two or more of the above-mentioned plurality of compounds. It can also be used in combination with plant hormones such as auxin.

The term "plant growth regulation" used in the present invention includes, for example, plant dwarfing (inhibition of elongation), regulation of flowering time, induction of upright leaves (and accompanying improvement of photosynthetic efficiency, biomass increasing action). Pollen growth suppression, flower freshness maintenance, plant anti-stress agents (heat, dryness, cold, etc.), weed control by reproductive control, plant aging control, root enlargement, fruit set promotion, fruit growth promotion, fruit drop prevention, It needs to be interpreted in the broadest sense, including promotion of pollen coloring. For example, a rooting promoter, a plant growth regulator, a root system development promoter, etc. are typical examples of the plant growth regulator of the present invention, but the plant growth regulator of the present invention is not limited to these. Absent.

In the plant growth regulator of the present invention, an aqueous solution or an aqueous dispersion of the above compound can be used as it is as a plant growth regulator, but ordinary plants such as wettable powders, emulsions, granules, powders and surfactants can be used. It may be formulated using the carrier used in the growth regulator. For example, as solid carriers, mineral powders (kaolin, bentonite, clay, montmorillonite, talc, keiso soil, mica, vermiculite, sekko, calcium carbonate, phosphorus lime, etc.), vegetable powders (soybean flour, wheat flour, wood flour, tobacco) Powders, starch, crystalline cellulose, etc.), polymer compounds (petroleum resin, polyvinyl alcohol resin, polyvinyl acetate resin, polyvinyl chloride, ketone resin, etc.), alumina, waxes, etc. can be used. Examples of the liquid carrier include alcohols (methanol, ethanol, propanol, butanol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (toluene, benzene, xylene, etc.), and chlorinated hydrocarbons (chloroform, etc.). Carbon tetrachloride, monochlorobenzene, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, etc.), esters (ethyl acetate, butyl acetate, etc.), acid amides (N, N-dimethylacetamide, etc.) , Ether alcohols (ethylene glycol ethyl ether, etc.), water, etc. can be used.

As the surfactant used for the purpose of emulsification, dispersion, diffusion and the like, any of nonionic, anionic, cationic and amphoteric surfactants can be used. Examples of surfactants that can be used in the present invention include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, and oxyethylene polymer. , Oxypropylene polymer, polyoxyethylene alkyl phosphate, fatty acid salt, alkyl sulfate, alkyl sulfonate, alkylaryl sulfonate, alkyl phosphate, alkyl phosphate, polyoxyethylene alkyl sulfate, It is a quaternary ammonium salt, oxyalkylamine, lecithin, saponin and the like. Further, if necessary, gelatin, casein, sodium alginate, starch, agar, polyvinyl alcohol and the like can be used as an auxiliary agent.

The plant growth regulator of the present invention is not limited in the form of the formulation, and can be molded into any formulation form such as powder, granule, granule, wettable powder, flowable agent, emulsion and paste. It can be produced by mixing, stirring, spray-drying and the like other components according to a conventional method.
When applied to plants, it can be used as a soil treatment agent, a foliage treatment agent, a seed treatment agent before sowing, a treatment agent for plants before transplantation, a treatment agent for plants at the time of transplantation, and the like. Further, in hydroponics, it may be mixed with a hydroponic solution and used, and in tissue culture, it may be suspended or dissolved in a medium.
When the plant growth regulator of the present invention is applied to a target plant, the root amount and root density increase as the number of roots such as the number of lateral roots and the number of adventitious roots increases. The effects of growing, promoting growth, improving water absorption, improving fertilizer absorption, improving fertilizer component utilization rate, maintaining green color, improving photosynthetic ability, improving water stress tolerance, preventing lodging, and increasing yield can be obtained. In addition, since the heat climbing of gramineous plants is improved, the yield of rice and the like can be improved.

When the plant growth regulator of the present invention is used for spraying, the concentration used can be preferably in the range of 0.01 to 10000 ppm, more preferably 1 to 5000 ppm, and particularly preferably 5 to 1000 ppm. In particular, when used for seedlings in the seedling raising period, it is desirable to spray 50 to 200 mL of the diluted solution having the above concentration per 1 L of potting soil. In this case, a spreading agent may be used, and the type and amount of the spreading agent used are not particularly limited. It is also effective when sprayed on the foliage.
The amount to be used when directly applied to soil, including when mixed with fertilizer, is preferably 100 to 10000 g, particularly 500 to 5000 g per hectare. In particular, when used for seedlings in the seedling raising period, it is desirable to use 0.001 to 10 g per 1 L of potting soil. In this case, it may be mixed in advance with the culture soil before sowing, or may be sprayed during the seedling raising period.

When used for seed treatment before sowing, water, alcohols (methanol, ethanol, etc.), ketones (acetone, etc.), aromatic hydrocarbons (toluene, benzene, etc.), chlorinated hydrocarbons (chloroform, chloride, etc.) Dilute to 0.01-100,000 ppm on a liquid carrier such as methylene), ethers (diethyl ether, etc.), esters (ethyl acetate, etc.) and spray on dried seeds, or immerse the dried seeds in a diluted solution. It can also be absorbed by the seeds. The immersion time is not particularly limited, but is preferably 1 second to 120 minutes. In addition, the treated seeds may be air-dried, vacuum-dried, heat-dried, vacuum-dried, or the like to evaporate the liquid carrier. It is also possible to use a product prepared by using a solid carrier of mineral powder such as clay by adhering it to the seed surface. It can also be mixed with a commonly used seed coating agent or seed coating film to coat the seeds.
When used in tissue culture or cell culture, the concentration in the medium is preferably 0.01 to 10000 ppm, particularly preferably 0.01 to 10,000 ppm, in a medium for plant tissue culture (MS medium, white medium, Gamborg's B5 medium, etc.) that is usually used. It can be used by dissolving or suspending in the range of 0.1 to 1000 ppm. In this case, as is usually done, sugars as carbon sources (sucrose, glucose, etc.), cytokinins (benzyladenine, kinetin, etc.), auxins (indoleacetic acid, naphthalene acetic acid, etc.), diberelin (GA3) as various plant hormones. , GA4, etc.), abscisic acid, etc. can be added as appropriate.
When directly absorbed by a plant before transplantation, the root or the whole of the plant can be immersed in a solution diluted or suspended at a concentration of 0.1 to 1000 ppm. Further, if it is a cutting, a cutting, a cutting, or the like, the base or the whole can be immersed and used. In this case, the immersion time is preferably 1 second to 1 week, particularly 1 minute to 3 days. A product formulated using a solid carrier of mineral powder may be attached to the root, or in the case of cuttings, cuttings, cuttings, etc., may be attached to the stem base.
The plant growth regulator of the present invention can be used at any time during the growing period, but when applied as a plant growth regulator, it is used before sowing, at the time of sowing, at the time of growing seedlings, and at the time of transplantation. It is especially effective before and after work involving cultivating root cutting, such as when root growth is hindered or root damage occurs due to meteorological factors.

The plant to which the plant growth regulator of the present invention is applied is not particularly limited, but for example, eggplants such as tomatoes, peppers, corns and eggplants, melons such as cucumbers, pumpkins, melons and watermelons, cereals and parsley. , Raw vegetables and spicy vegetables such as lettuce, green onions such as onions, onions and garlic, beans such as soybeans, lacquer, green beans, pea and azuki, other fruit vegetables such as strawberries, direct fruits such as corn, cub, carrot and gobo Roots, sweet potatoes, cassava, potatoes, sweet potatoes, potatoes and other potatoes, asparagus, spinach, honeybees and other soft vegetables, Turkish ginkgo, stock, carnation, kiku and other grains, rice, corn and other grains, bentgrass , Turbs such as melon, oil crops such as rapeseed and sunflower, sugar crops such as sugar beet and sugar beet, fiber crops such as cotton and igusa, forage crops such as clover, sorghum and dent corn, apples and pears. , Grains, deciduous fruit trees such as peach, citrus fruits such as unshu mikan, lemon and grapefruit, and woody plants such as satsuki, tsutsuji and sugi. Of these, tomatoes, peppers, peppers, eggplants, cucumbers, pumpkins, melons, watermelons, celluris, parsleys, lettuce, onions, onions, asparagus, Turkish guikyo, stocks, rice, bentgrass, azaleas, tensai, igusa, etc. are being cultivated. It is particularly effective for plants that are transplanted to tomatoes and plants that grow by rooting from cuttings or cuttings such as cucumbers, carnations, watermelons, azaleas, and grapes. In addition, examples of gramineous plants for the purpose of preventing lodging include rice, wheat, barley, rye, and corn. In particular, when rice and wheat are sprayed during the division period, many adventitious roots are generated, the growth of the entire root system is promoted, and the absorption efficiency of nutrients is improved. preferable.

Further, for the purpose of improving the effect of the present invention, it can be used in combination with another plant growth regulator (plant hormone agent) as described above, and in some cases, a synergistic effect can be expected. For example, when raising seedlings under extremely long-term conditions such as high planting density, high humidity, and lack of sunshine, it has a strong stem elongation inhibitory effect for the purpose of growing high-quality seedlings with a small above-ground and underground weight ratio. It may be used in combination with an anti-gibberellin agent (paclobutrazol, uniconazole P, ansimidol, etc.), a growth inhibitor (daminozide, etc.), and an ethylene generator (ethephon, etc.). In cuttings, cuttings, cuttings, and tissue culture, it may be used in combination with an auxin-based compound (indoleacetic acid, indolebutyric acid, naphthylacetamide, naphthaleneacetic acid, etc.) for the purpose of enhancing the rooting promoting effect. At the time of seed treatment before sowing, it may be used in combination with a gibberellin agent having a germination promoting action.

The plant growth regulator of the present invention can also be mixed or used in combination with various insecticides, fungicides, microbial pesticides, fertilizers and the like. In particular, when used in combination with a fungicide, it is effective to use in combination with hydroxyisoxazole, metasulfocarb, metalaxil, etc., which have been reported to have a rooting promoting action in addition to the bactericidal action. It is particularly effective when used in combination with an insecticide that treats seeds directly or that is used during the seedling raising period (thiamethoxam, fludioxonyl, metalaxil, chlorantraniliprole, etc.).
When used in combination with fertilizer, it is particularly effective to use it in combination with a fertilizer for raising seedlings for the purpose of growing healthy seedlings and a fertilizer applied immediately before transplanting for the purpose of promoting survival. Mixing with a slow-release fertilizer for the purpose of sustaining the efficacy of the plant growth regulator of the present invention for a long period of time and improving the utilization rate of fertilizer components is also particularly effective.

Next, the present invention will be described in more detail with reference to Production Examples of Compounds 2 to 4, Test Examples of Compounds 1 to 4, and Examples, but the present invention is not limited to these Examples.

Production example <Compound 2>
925.3 mg of methyl 5-chloroanthranilate was placed in an argon atmosphere and dissolved in 5 mL of acetic acid. To this, 1.24 g of N-iodosuccinimide was added, and the mixture was stirred at room temperature for 17 hours. The reaction solution was added dropwise to 12.5 mL of a saturated aqueous sodium hydrogen carbonate solution to neutralize acetic acid. The ethyl acetate phase obtained by extracting this with ethyl acetate was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure.
The obtained substance was placed in an argon atmosphere and dissolved in 17 mL of triethylamine. To this, 176.6 mg of bis (triphenylphosphine) palladium (II) dichloride, 47.8 mg of copper (I) iodide, and 0.85 mL of trimethylsilylacetylene were added, and the mixture was stirred at room temperature for 90 minutes. The reaction mixture was diluted with dichloromethane, washed successively with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure.
The obtained substance was dissolved in 8 mL of N-methyl-2-pyrrolidone, and 1.28 g of potassium tert-butoxide was added dropwise to the mother liquor containing 16 mL of N-methyl-2-pyrrolidone at 0 ° C. under an argon atmosphere. After stirring for 1 hour, the mixture was stirred at room temperature for 90 minutes. The reaction solution was brought to 0 ° C. again, 80 mL of water was added, and the temperature was returned to room temperature. The diethyl ether phase extracted with diethyl ether was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then under reduced pressure. The solvent was distilled off at. The residue was purified by silica gel column chromatography using a 10% ethyl acetate 90% hexane mixed solution as a developing solvent, and the solvent was distilled off.
111.1 mg of the obtained substance was placed in an argon atmosphere, 5.3 mL of 2N sodium hydroxide and 5.3 mL of ethanol were added to bring the temperature to 40 ° C., and the mixture was stirred for 2 hours. The reaction mixture was brought to room temperature, the pH was adjusted to the acidic side with 3N hydrochloric acid, sodium chloride was added until saturated, and the ethyl acetate phase eluted with ethyl acetate was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the solvent was dissolved in ethyl acetate, activated carbon was added to adsorb impurities, and the activated carbon was removed by filtration. The residue obtained by distilling off the solvent was dissolved in diethyl ether, the insoluble material was filtered off, and the solvent was distilled off to obtain 85.0 mg (yield 8.7%) of the compound. For this compound, NMR, mass spectrum, and melting point were measured, and compound 2 having the structure of the general formula 3 was confirmed.

<Compound 3>
463.5 mg of methyl 5-bromoanthranilate was placed in an argon atmosphere and dissolved in 2 mL of acetic acid. To this, 499.5 mg of N-iodosuccinimide was added, and the mixture was stirred at room temperature for 17 hours. The reaction solution was added dropwise to 5 mL of a saturated aqueous sodium hydrogen carbonate solution to neutralize acetic acid. The ethyl acetate phase obtained by extracting this with ethyl acetate was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure.
The obtained substance was placed in an argon atmosphere and dissolved in 6.6 mL of triethylamine. To this was added 74.2 mg of bis (triphenylphosphine) palladium (II) dichloride, 22.3 mg of copper (I) iodide, and 0.34 mL of trimethylsilylacetylene, and the mixture was stirred at room temperature for 90 minutes. The reaction mixture was diluted with dichloromethane, washed successively with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure.
The obtained substance was dissolved in 9 mL of N-methyl-2-pyrrolidone, and 512.3 mg of potassium tert-butoxide was added dropwise to the mother liquor containing 7 mL of N-methyl-2-pyrrolidone at 0 ° C. under an argon atmosphere. After stirring for 1 hour, the mixture was stirred at room temperature for 90 minutes. The reaction solution was brought to 0 ° C. again, 32 mL of water was added, and the temperature was returned to room temperature. The diethyl ether phase extracted with diethyl ether was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then under reduced pressure. The solvent was distilled off at. The residue was dissolved in methanol, the insoluble material was removed by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using 10% ethyl acetate / hexane as a developing solvent, and the solvent was distilled off. ..
62.5 mg of the obtained substance was placed in an argon atmosphere, 2.4 mL of 2N sodium hydroxide and 2.4 mL of ethanol were added to bring the temperature to 40 ° C., and the mixture was stirred for 2 hours. The reaction mixture was brought to room temperature, the pH was adjusted to the acidic side with 3N hydrochloric acid, sodium chloride was added until saturated, and the ethyl acetate phase eluted with ethyl acetate was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the solvent was suspended in diethyl ether, the brown solid content of the insoluble material was removed, and the remaining insoluble material was washed with warm hexane. The solvent was distilled off and dissolved in ethyl acetate, activated carbon was added to adsorb impurities, and the activated carbon was removed by filtration. The residue obtained by distilling off the solvent was dissolved in diethyl ether, the insoluble material was filtered off, and the solvent was distilled off to obtain 54.2 mg (yield 11.3%) of the compound. For this compound, NMR, mass spectrum, and melting point were measured, and compound 3 having the structure of the general formula 4 was confirmed.

<Compound 4>
Methylindole-7-carboxylic acid 1 g of indole-7-carboxylic acid was dissolved in 10 ml of methanol. 5 ml of trimethylsilyldiazomethane was added, and the mixture was allowed to stand at room temperature for 30 minutes. 1N acetic acid was added until the reaction solution became colorless, and the solvent was distilled off. The obtained substance was dissolved in distillation, adjusted to pH 8, extracted with ethyl acetate, and the obtained ethyl acetate phase was dried over anhydrous magnesium sulfate. This was dissolved in acetone and recrystallized, and the solvent was distilled off to obtain 148.7 mg (yield 13.7%) of the compound. For this compound, NMR, mass spectrum, and melting point were measured, and compound 4 having the structure of the general formula 5 was confirmed.
The NMR measurement results and melting point measurement results of compounds 2 to 4 are shown in Table 1 below.

Test example <Confirmation test of adzuki bean root generation induction action by adzuki bean cut edge immersion treatment>
Dilute the above compounds 1 to 4 with distilled water to prepare aqueous solutions with concentrations of 0.03 mM, 0.1 mM and 1 mM, adjust the pH to 7 using dilute hydrochloric acid and sodium hydroxide aqueous solution, and perform the Azuki rooting promotion assay (Itagaki et. al. 2003. Biological activities and structure-activity relationship of substitution compounds of N- [2- (3-indolyl) ethyl] succinamic acid and N- [2- (1-naphthyl) ethyl] succinamic acid, derived from a new category Of root-promoting substance, N- (phenethyl) succinamic acid analogs. Plant Soil 255: 67-75.) Was performed. The azuki bean section, which was not tested using a solution of 0.1 mM and 1 mM only for compound 4, was generated after 7 days by immersing the base in each test solution of 0.03 mM, 0.1 mM and 1 mM for 48 hours. I counted the number of adzuki beans. The number of repetitions was 5. When measuring the activity of each compound, those treated with distilled water were cultured as a control, and the number of adventitious roots was measured in the same manner. Therefore, the control group showed the total mean value measured multiple times.
The test results are shown in Table 2 below.

As shown in Table 2, the solutions containing compounds 1 to 4 were found to have a high adventitious rooting inducing effect and a rooting promoting effect as compared with the number of adventitious rooting in the control group. In particular, compounds 1 to 3 showed a strong effect. In addition, at a concentration of 0.03 mM, the rooting rate of compounds 2 and 3 was 200% or more with respect to the control distilled water. Furthermore, the rooting rate was 400% or more with respect to distilled water at a concentration of 1 mM and the compound 1 was the control. In addition, no signs such as chlorosis of stems and leaves were observed.

<Effect in the field>
Compounds 1 to 3 were mixed with fertilizer and sprayed on corn being cultivated in the field. For each compound, it was confirmed that the root system development and growth were significantly promoted and the yield was increased as compared with the field where only fertilizer was applied. In addition, the occurrence of chlorosis on stems and leaves due to spraying was not observed.

<Corn support root increase effect test>
For feed corn (variety LG3215; Snow Brand Seed Co., Ltd.), 1/1000 amount of spreading agent in 1 mM indol-7-carboxylic acid solution (approach BI: polyoxyethylene hexitane fatty acid ester: Maruwa Biochemical Co., Ltd.) The product to which the company) was added was foliar sprayed four times every two weeks from the third week after sowing.
Supporting roots were counted for 20 plants 4 months after sowing, and the average value was calculated.
The test results are shown in Table 3 below.

As shown in Table 3, the solution containing 1 mM indole-7-carboxylic acid showed a strong supporting rooting action as compared with the control group. It was clear that the compound used in the present invention was effective even in soil hydroponics.

<Confirmation test of root system development effect on Arabidopsis thaliana>
Wild-type Arabidopsis thaliana (Col.-0) was sown in a 1/2 concentration MS medium containing 30 μM indole-7-carboxylic acid, and cultivated at 22 ° C. in a bright place for 12 hours and in a dark place for 12 hours. The total root length was measured for the individual after 2 weeks using the root system image analysis software WinRhizo Reg. The control group was a 1/2 concentration MS medium, and the average value of 3 individuals was calculated.
The test results are shown in Table 4 below.

As shown in Table 4, root length elongation was promoted in the medium containing 1 mM indole-7-carboxylic acid as compared with the control group.

Claims (4)

A plant growth modifier containing any one or more of indole-7-carboxylic acid, 5-chloroindole-7-carboxylic acid, 5-bromoindole-7-carboxylic acid, and methyl indole-7-carboxylic acid. A rooting agent containing the plant growth regulator according to claim 1. A fertilizer containing the plant growth regulator according to claim 1. A pesticide containing the plant growth regulator according to claim 1.