JP2001139405A - Plant growth regulator - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an amide derivative having high activities for promoting rooting of a plant and substantially having no side effect, and further to prepare a plant growth regulator containing the amide derivative as an active ingredient. SOLUTION: This plant growth regulator contains a compound represented by general formula (1) (wherein, R1 is 3-indolyl, 1-naphthyl or the like; A is methylene or the like; B is methylene or the like; and R2 is hydroxy or the like) or a salt thereof as an active ingredient. The amide derivative is represented by general formula (2) (wherein, D is methylene or the like; E is methylene or the like; and R3 is hydroxy or the like).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a plant growth regulator having a high rooting promoting activity of a plant, useful as an agricultural chemical or a fertilizer additive, and a novel amide derivative having such an effect.

[0002]

BACKGROUND OF THE INVENTION In the agricultural field, controlling the growth of plants is an important technique for improving productivity. At present, various types of plant growth regulators for the purpose of suppressing plant growth have been put to practical use, contributing to the improvement of crop yield and product quality.

[0003] Roots of plants are diverse, such as absorbing water and nutrients necessary for growth and supporting the above-ground parts to prevent lodging, and it is important to fully develop the roots of plants in the agricultural field. It has been pointed out before [Bo
Ote et al., Physiology and Dete
rmination of Crop Yield65
-93 (1994), ed., Encyclopedia of editors, ed., Pp. 261-289 (1998)].

[0004] However, plant growth regulators that promote the development of roots are small in number, have insufficient effects, and often have unfavorable effects. For example, auxin-based compounds widely used as rooting agents are currently dependent on the type and condition of the plant and the concentration of the applied plant, inducing epistatic bending of the leaves, inducing torsion and cracking of the stem, inducing root knots, and more. May have undesirable effects such as withering. For this reason, the method of use and the amount of use are limited, and the effect of promoting root development has not been sufficiently satisfactory.

[0005] Also, in plant tissue culture, it is common to add an auxin-based compound to the medium when it is desired to induce root differentiation. In addition, the induction rate may be extremely low, which has been a problem.

Therefore, the present invention has high activity of promoting rooting of plants and has side effects such as upgrowth of leaves from the viewpoint of raising and raising seedlings and seedlings of agricultural crops, establishment of lawn vegetation and the like, and utilization in tissue culture. It is an object of the present invention to provide an amide derivative substantially having no amide and a plant growth regulator containing the amide derivative as an active ingredient.

[0007]

Means for Solving the Problems The inventors of the present invention have made intensive studies to solve the above-mentioned problems, and as a result, unexpectedly, the compound represented by the following general formula (1) was found to have an unbalanced growth on leaves. They have found that they have substantially no side effects, have high rooting promoting activity of plants, are useful as plant growth regulators, and that some compounds in the general formula (1) are novel, The present invention has been completed.

That is, the present invention provides the following general formula (1)

[0009]

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(Wherein R ¹ may have a substituent;
A represents an indolyl group or a 1-naphthyl group, A represents a linear or branched lower alkylene group, B represents a linear or branched lower alkylene group or a lower alkenylene group which may have a substituent, R ² represents a hydroxy group, a lower alkoxy group or an amino group. ), Or a plant growth regulator containing the compound or a salt thereof as an active ingredient.

The present invention also provides the following general formula (2)

[0012]

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(Wherein D represents a methylene group or an ethylene group, E represents a methylene group, an ethylene group, a trimethylene group or a vinylene group, R ³ represents a hydroxy group, a methoxy group, an ethoxy group, an n-propoxy group, n-butoxy group,
It represents an n-pentyloxy group or an amino group. However, when D is a methylene group and E is an ethylene group, R ³ is a methoxy group. When both D and E are ethylene groups, R ³ is a hydroxy group. ) Is provided.

The present invention also relates to 3-oxo-3-[[2-
(3-indolyl) ethyl] amino] -propionic acid,
5-oxo-5-[[2- (3-indolyl) ethyl]
Amino] -methyl valerate, 5-oxo-5-[[2-
(3-Indolyl) ethyl] amino] -n-propyl valerate or 5-oxo-5-[[2- (5-methyl-3-
Indolyl) ethyl] amino] -valeric acid.

[0015]

BEST MODE FOR CARRYING OUT THE INVENTION The active ingredient of the plant growth regulator of the present invention (hereinafter referred to as "plant growth regulator") is a compound represented by the above general formula (1) or a salt thereof.

In the general formula (1), examples of the optionally substituted 1-naphthyl group represented by R ¹ include a halogen atom, a hydroxy group, a nitro group, a lower alkyl group and a lower alkyl group on the naphthalene ring. Examples thereof include a 1-naphthyl group which may be substituted by 1 to 7 groups selected from an alkoxy group. Such a 1-naphthyl group which may have a substituent is represented by the general formula (3).

[0017]

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(Wherein R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are the same or different and are each a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a lower alkyl group or a lower alkoxy group) Represents a group.)

In the general formula (1), the 3-indolyl group which may have a substituent represented by R ¹ includes:
For example, a 3-indolyl group may be substituted on the indole ring by 1 to 6 groups selected from a halogen atom, a hydroxy group, a nitro group, a lower alkyl group and a lower alkoxy group. 3 which may have such a substituent
-The indolyl group is represented by the general formula (4).

[0020]

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(Wherein, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ are the same or different and represent a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a lower alkyl group or a lower alkoxy group) .)

Here, the lower alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, i-propyl, i-butyl and i-pentyl. And an alkyl group having 1 to 6 carbon atoms such as a group and an i-hexyl group. Examples of the lower alkoxy group include 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,
Examples thereof include an alkoxy group having 1 to 6 carbon atoms such as an i-pentyloxy group and an i-hexyloxy group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Of these, 3-indolyl group and 5-
A methyl-3-indolyl group is particularly preferred.

When the 1-naphthyl group has a substituent, the substituent may be located at any of the 2- to 8-positions. Also,
When the 3-indolyl group has a substituent, the substitution position may be any of the 1-2 position and the 4-7 position.

A is a linear or branched lower alkylene group, for example, an alkylene group having 1 to 6 carbon atoms such as a methylene group, an ethylene group, a trimethylene group, a propylene group, a tetramethylene group, a pentamethylene group and a hexamethylene group. Groups. Among them, a methylene group or an ethylene group is preferred. B is a linear or branched lower alkylene group or a lower alkenylene group which may have a substituent, and examples of the lower alkylene group which may have a substituent include the same as the above A. As the lower alkenylene group which may have a substituent, for example, a vinylene group,
Carbon number 2 which may have a substituent such as a propenylene group, a butenylene group, a pentenylene group and a hexenylene group;
To 6 alkenylene groups. Among them, the lower alkylene group is preferably a straight-chain alkylene group having 1 to 3 carbon atoms. The lower alkenylene group which may have a substituent is preferably a vinylene group. The configuration around the alkenylene group may be either cis or trans, but cis is preferred. R ² is a hydroxy group, a lower alkoxy group or an amino group, and examples of the lower alkoxy group include the same as described above. R ² includes a hydroxy group, an amino group, a methoxy group, an ethoxy group, an n-
A propoxy group, an n-butoxy group and an n-pentyloxy group are preferred. 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, and triethylamine salt. And salts with organic bases such as pyridine salts, picoline salts, ethanolamine salts, triethanolamine salts, dicyclohexylamine salts, and organic amine salts such as N, N'-dibenzylethylenediamine salt.

Among the plant growth regulators, particularly preferred are
Is R¹Is a 1-naphthyl group, a 3-indolyl group or 5-
A methyl-3-indolyl group, wherein A is a methylene group or
An ethylene group, wherein B is a straight-chain alkylene having 1 to 3 carbon atoms
Or a vinylene group; ^TwoIs a hydroxy group, amino
Group, methoxy group, ethoxy group, n-propoxy group, n-
This is the case of a butoxy group or an n-pentyloxy group.

Particularly preferred among the plant growth regulators are the following combinations of R ¹ , A, B and R ² . That is, R ¹ , A, B and R ² are each a 3-indolyl group, an ethylene group, a methylene group, a hydroxy group;
3-indolyl, ethylene, methylene, methoxy; 3-indolyl, ethylene, ethylene, hydroxy; 3-indolyl, ethylene, ethylene, methoxy; 3-indolyl, ethylene, Trimethylene group, hydroxy group; 3-indolyl group, ethylene group, trimethylene group, methoxy group; 3-indolyl group, ethylene group, trimethylene group, ethoxy group; 3-indolyl group, ethylene group, trimethylene group, n-propoxy group; 3-indolyl group, ethylene group, cis-vinylene group, hydroxy group; 5-methyl-3-indolyl group, ethylene group, trimethylene group, hydroxy group; 1-
Naphthyl group, methylene group, methylene group, hydroxy group;
1-naphthyl group, methylene group, methylene group, methoxy group; 1-naphthyl group, methylene group, ethylene group, hydroxy group; 1-naphthyl group, methylene group, ethylene group, methoxy group; 1-naphthyl group, methylene group, Trimethylene group, hydroxy group; 1-naphthyl group, methylene group, trimethylene group, methoxy group; 1-naphthyl group, methylene group, trimethylene group, ethoxy group; 1-naphthyl group, methylene group, trimethylene group, n-propoxy group; 1-naphthyl group, methylene group, trimethylene group, n-butoxy group; 1-naphthyl group, methylene group, trimethylene group, n
1-naphthyl group, methylene group, trimethylene group, amino group; 1-naphthyl group, methylene group, cis-vinylene group, hydroxy group; 1-naphthyl group, ethylene group, methylene group, hydroxy group; 1-naphthyl group, ethylene group, methylene group, methoxy group; 1-naphthyl group, ethylene group, ethylene group, hydroxy group;
-A naphthyl group, an ethylene group, an ethylene group, a methoxy group;
1-naphthyl group, ethylene group, trimethylene group, hydroxy group; 1-naphthyl group, ethylene group, trimethylene group, methoxy group; 1-naphthyl group, ethylene group, trimethylene group, ethoxy group; 1-naphthyl group, ethylene group,
Trimethylene group, n-propoxy group; 1-naphthyl group,
Ethylene group, trimethylene group, n-butoxy group; 1-naphthyl group, ethylene group, trimethylene group, n-pentyloxy group; or 1-naphthyl group, ethylene group, cis-
It is a compound that is a vinylene group or a hydroxy group.

Specific examples of such particularly preferred plant growth regulators are shown below. 5-oxo-5-[[2- (3-indolyl) ethyl] amino] -valeric acid (Compound 01);
5-oxo-5-[[2- (3-indolyl) ethyl]
Amino] -methyl valerate (Compound 02); 5-oxo-
5-[[2- (3-Indolyl) ethyl] amino] -ethyl valerate (Compound 03); 5-oxo-5-[[2-
(3-Indolyl) ethyl] amino] -n-propyl valerate (compound 04); 5-oxo-5-[[(1-naphthyl) methyl] amino] -valeric acid (compound 05); 5-oxo-5 -[[(1-naphthyl) methyl] amino] -methyl valerate (Compound 06); 5-oxo-5-[[(1
-Naphthyl) methyl] amino] -ethyl valerate (compound 07); 5-oxo-5-[[(1-naphthyl) methyl] amino] -n-propyl valerate (compound 08); 5
-Oxo-5-[[(1-naphthyl) methyl] amino]
-N-butyl valerate; 5-oxo-5-[[(1-naphthyl) methyl] amino] -n-pentyl valerate; 5-oxo-5-[[(1-naphthyl) methyl] amino] -pentane Amide (compound 21); 5-oxo-5-[[2
-(1-naphthyl) ethyl] amino] -valeric acid (compound 09); 5-oxo-5-[[2- (1-naphthyl) ethyl] amino] -methyl valerate (compound 10); 5-oxo- 5-[[2- (1-naphthyl) ethyl] amino]
-Ethyl valerate (compound 20); 5-oxo-5-
[[2- (1-Naphthyl) ethyl] amino] -valeric acid n
-Propyl; 5-oxo-5-[[2- (1-naphthyl) ethyl] amino] -n-butyl valerate; 5-oxo-5-[[2- (1-naphthyl) ethyl] amino] -k 4-oxo-4-[[2- (3-indolyl) ethyl] amino] -butyric acid (compound 11);
-Oxo-4-[[(1-naphthyl) methyl] amino]
-Butyric acid (compound 12); (Z) -4-oxo-4-
[[(1-Naphthyl) methyl] amino] -butenoic acid (Compound 13); 5-oxo-5-[[2- (5-methyl-
3-Indolyl) ethyl] amino] -valeric acid (Compound 1
4); Methyl 3-oxo-3-[[2- (3-indolyl) ethyl] amino] -propionate (Compound 19);
3-oxo-3-[[2- (3-indolyl) ethyl]
Amino] -propionic acid; 4-oxo-4-[[2-
(3-Indolyl) ethyl] amino] -methyl butyrate; 4
-Oxo-4-[[2- (3-indolyl) ethyl] amino] -butenoic acid; 3-oxo-3-[[(1-naphthyl) methyl] amino] -propionic acid (compound 16);
Methyl 3-oxo-3-[[(1-naphthyl) methyl] amino] -propionate (compound 15); methyl 4-oxo-4-[[(1-naphthyl) methyl] amino] -butyrate; 3-oxo -3-[[2- (1-Naphthyl) ethyl] amino] -propionic acid (compound 18); 3-oxo-3-[[2- (1-naphthyl) ethyl] amino]-
Methyl propionate; 4-oxo-4-[[2- (1-
Naphthyl) ethyl] amino] -butyric acid; 4-oxo-4-
[[2- (1-naphthyl) ethyl] amino] -methyl butyrate; 4-oxo-4-[[2- (1-naphthyl) ethyl] amino] -butenoic acid; (Z) -4-oxo-4-
[[2- (3-Indolyl) ethyl] amino] -butenoic acid (Compound 17).

The novel amide derivative according to the present invention comprises a compound represented by the general formula (2) and 3-oxo-3-
[[2- (3-Indolyl) ethyl] amino] -propionic acid, 5-oxo-5-[[2- (3-Indolyl)
Ethyl] amino] -methyl valerate, 5-oxo-5-
[[2- (3-Indolyl) ethyl] amino] -n-propyl valerate, 5-oxo-5-[[2- (5-methyl-3-indolyl) ethyl] amino] -valeric acid.
In the general formula (2), D is a methylene group or an ethylene group, E is a methylene group, a trimethylene group, or a vinylene group, and R ³ is a hydroxy group, a methoxy group, an ethoxy group, an n-propoxy group, or an n-butoxy group. A n-pentyloxy group or an amino group. Provided that when D is a methylene group and E is an ethylene group, R ³ is a methoxy group;
When both D and E are ethylene groups, R ³ is a hydroxy group. In the amide derivative of the present invention, in the general formula (2), D, E and R ³ each represent a methylene group, a methylene group, a hydroxy group; a methylene group, a methylene group, a methoxy group; a methylene group, an ethylene group, Methoxy group; methylene group, trimethylene group, hydroxy group; methylene group, trimethylene group, methoxy group; methylene group, trimethylene group, ethoxy group; methylene group, trimethylene group, n-propoxy group; methylene group, trimethylene group;
n-butoxy group; methylene group, trimethylene group, n-pentyloxy group; methylene group, trimethylene group, amino group; methylene group, vinylene group, hydroxy group; ethylene group, methylene group, hydroxy group; ethylene group, methylene group; Methoxy group; ethylene group, ethylene group, hydroxy group; ethylene group, trimethylene group, hydroxy group; ethylene group, trimethylene group, methoxy group; ethylene group, trimethylene group, ethoxy group; ethylene group, trimethylene group, n-propoxy group; Ethylene group, trimethylene group,
n-butoxy group; ethylene group, trimethylene group, n-pentyloxy group; or a compound which is an amide derivative which is ethylene group, vinylene group, or hydroxy group; and 3-oxo-3-[[2- (3-indolyl) Ethyl] amino]
-Propionic acid, 5-oxo-5-[[2- (3-indolyl) ethyl] amino] -methyl valerate, 5-oxo-5-[[2- (3-indolyl) ethyl] amino]-
N-propyl valerate, 5-oxo-5-[[2- (5-
Methyl-3-indolyl) ethyl] amino] valeric acid is preferred.

The plant growth regulator used in the present invention can be produced, for example, by the following method.

[0030]

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[0031]

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[0032]

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[0033]

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(Wherein R ¹ , A and B are the same as described above. R ^1-1 is a protecting group for a hydroxy group, an amino group or a carboxyl group. X represents a hydroxy group.
And-may form a reactive derivative of a carboxylic acid such as an acid halide, an active ester, or an acid azide. R ^1-2 represents a lower alkyl group. X ′ represents a halogen atom such as chlorine and bromine. )

Next, Production Method 1 will be described. Compound (a) is a salt with an inorganic acid such as hydrochloride, hydrobromide, hydroiodide, sulfate, perchlorate, phosphate, nitrate or carbonate, acetate, oxalic acid It may be a salt with an organic acid such as a salt, a maleate, a fumarate, a succinate, a tartrate, a methanesulfonate, an ethanesulfonate, and a toluenesulfonate. As the anhydrides represented by the compound (b), for example, malonic anhydride [B
Is CH ₂ ], succinic anhydride [B is (CH ₂ ) ₂ ], maleic anhydride [B is CH = CH (cis)], glutaric anhydride [B is (CH ₂ ) ₃ ], adipic anhydride [B Is (C
H ₂ ) ₄ ] and pimelic anhydride [B is (CH ₂ ) ₅ ]. Compound (c-1) may be a salt with the above-mentioned acid or base.

In the production method 1, the compound (a) and the compound (b) are converted into an inert medium, for example, a ketone solvent such as acetone and methyl ethyl ketone, diethyl ether, 1,4
-Ether solvents such as dioxane and tetrahydrofuran; organic chlorinated solvents such as chloroform, methylene chloride and ethylene chloride; aprotic polar organic solvents such as N, N-dimethylacetamide, dimethylsulfoxide, N, N-dimethylformamide; The compound (c-1) can be synthesized by reacting in a solvent, an aromatic solvent such as benzene or toluene. The molar ratio of the compound (a) to the compound (b) is, for example, 0.5 to 1.5: 1.5.
The concentration is not particularly limited as long as it can react, but is preferably, for example, 1 to 30% (W / V), and particularly preferably the compound concentration is 5 to 0.5.
20% (W / V). Under such conditions, for example, 0 to 60
The reaction may be carried out by stirring at a temperature of 5 minutes to 24 hours. When the compound (a) is a salt, the compound (a) may be desalted in advance with an acid binder described below.

Next, Production Method 2 will be described. Compound
As (d), for example, malonic acid [B is CH_Two], Koha
C acid [B is (CH_Two)_Two], Maleic acid [B is CH = CH
(Cis)], fumaric acid [B is CH = CH (tran)
s)], glutaric acid [B is (CH _Two)_Three], Adipic acid
[B is (CH_Two)_Four], Pimelic acid [B is (CH_Two)_Five]But
No. When compound (d) is an active ester,
For example, cyanomethyl ester, phenylthioester,
p-Nitrophenylthioester, methanesulfonic acid
Ester, benzenesulfonic acid ester, toluenes
Sulfonic acid ester, p-nitrophenyl ester,
2,4-dinitrophenyl ester, 2,4,5-tri
Chlorophenyl ester, 2,4,6-trichlorophen
Nyl ester, pentachlorophenyl ester, N-
Droxysuccinimide ester, N-hydroxy phthalate
Luminimide ester, 1H-1-hydroxybenzotri
Azole esters, 8-hydroxyquinoline esters,
N-hydroxypiperidine ester and the like can be mentioned.
Protecting group R^1-1Is hydrolyzed with dilute alkaline or acidic solutions
Is particularly limited as long as it forms a carboxyl group
But not methoxy, ethoxy, propoxy
Group, isopropoxy group, butoxy group, isobutoxy group,
Lower alkoxy such as pentyloxy and hexyloxy
And aralkyloxy groups such as benzhydryl group.
And optionally these protecting groups are R¹May mean.
In addition to the active ester method described above, a known acid azide method
May go.

In the production method 2, when X is a hydroxyl group, in the reaction of the compound (a) with the compound (d), for example, 1,3-dicyclohexylcarbodiimide,
The compound (c-2) can be synthesized by reacting with a dehydrating condensing agent such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide. At this time, when the compound (a) is a salt, the compound (a) may be desalted in advance with an acid binder described below. Also,
When X is a halogen atom, compound (c-2) can be synthesized by reacting compound (d) with compound (a) in the presence of an acid binder described below. Solvents used in this method include, for example, organic chlorine solvents such as methylene chloride and chloroform, ether solvents such as diethyl ether and tetrahydrofuran, aromatic solvents such as benzene and toluene, heterocyclic solvents such as pyridine, N, N Aprotic polar solvents such as -dimethylformamide, N, N-dimethylacetamide and dimethylsulfoxide. Of these,
Pyridine is most preferred, but when using a solvent other than pyridine, an organic base such as triethylamine, tributylamine, dimethylamine, pyridine or the like as an acid binding agent,
Inorganic bases such as calcium carbonate, sodium carbonate and sodium hydroxide can be used.

When R ^1-1 is the above-mentioned protecting group, the reaction may be carried out using, for example, an equimolar to 1.5-fold molar amount of a dehydrating condensing agent with respect to compound (d). After completion of the reaction, if R ^1-1 is the above-mentioned protecting group,
Hydrolysis may be carried out using 10N NaOH, KOH or the like under alkaline conditions at room temperature or under heating for 30 minutes to 8 hours, and then neutralized with concentrated hydrochloric acid.

The reaction solution obtained in the production method 1 or 2 is appropriately cooled to precipitate and recover the desired product, and then water or a solubilized organic solvent such as acetone, methanol, ethanol, dimethyl sulfoxide, The desired product can be obtained by recrystallization from a single or mixed solvent of N, N-dimethylformamide, chloroform, methylene chloride, benzene, toluene and the like.

In the case of recovering the target substance from the reaction solution in the production method 1, after distilling off the reaction solvent, an alkaline aqueous solution, for example, a 5% to saturated aqueous solution of sodium hydrogencarbonate, and an organic solvent immiscible with water, for example, ethyl acetate After extraction with diethyl ether, methylene chloride, chloroform, etc.
The aqueous phase is adjusted to pH 2-3 with an acid such as concentrated hydrochloric acid, extracted with a water-miscible product-soluble organic solvent, the organic solvent layer is collected, dried, and the solvent is distilled off. Depending on,
It can be obtained by recrystallization from a single or mixed solvent or purification by silica gel column chromatography using a single or mixed solvent.

When the target product is recovered from the reaction solution in the production method 2, the reaction solution is extracted by adding a product-soluble organic solvent which does not mix with water and further with water, and then the organic solvent layer is diluted with a dilute acidic aqueous solution, for example, After washing with a 1-5N hydrochloric acid aqueous solution, washing with water, further washing with an alkaline aqueous solution, for example, a 5% to saturated sodium carbonate aqueous solution, finally washing with water sequentially, drying and evaporating the solvent, the solvent is removed as necessary. Accordingly, it can be obtained by recrystallization from a single or mixed solvent or purification by silica gel column chromatography using a single or mixed solvent.

Next, Production Method 3 will be described. For example, using compound (c-1) as a raw material, a lower alcohol or a lower alcohol is used in the presence of an acid catalyst such as sulfuric acid or p-toluenesulfonic acid.
For example, compound (c-3) can be obtained by heating to reflux in methanol, ethanol, propanol, n-butanol, or n-pentanol. At this time, the initial concentration of the compound (c-1) is not particularly limited.
It is preferably 20% by weight, particularly preferably 5 to 10% by weight. Compound (c-3) may be a salt with the above-mentioned acid or base.

To collect the product from the reaction solution after the reaction, the reaction solvent is distilled off, the product-soluble organic solvent immiscible with water and water are added, and the organic solvent layer is recovered. % To saturated aqueous solution of sodium hydrogencarbonate, then washed with water, dried, and evaporated to remove the organic solvent, and if necessary, recrystallized from a single solvent or a mixed solvent.

Next, Production Method 4 will be described. For example, the compound (c-1) is used as a raw material and, for example, thionyl chloride is used in an equimolar amount or more and reacted at room temperature for 5 to 30 minutes with stirring. After the reaction, thionyl chloride is distilled off to obtain a compound (e).
Then, the reaction mixture is added to aqueous ammonia in an organic solvent such as an inert organic solvent such as acetone, dimethyl sulfoxide, N, N-dimethylformamide, chloroform, methylene chloride, ethylene chloride, benzene, and toluene, and cooled with ice. To react for about 10 to 30 minutes, then collect the precipitated crystals, and recrystallize the obtained crystals from a single solvent or a mixed solvent, if necessary, to obtain a compound (c-
4) can be obtained. At this time, the initial concentration of the compound (c-1) is not particularly limited, but is, for example, 1 to 20% (W /
V), particularly preferably 5 to 10% (W / V). The initial concentration of the compound (e) in aqueous ammonia is not particularly limited, but is preferably, for example, 1 to 25% by weight, particularly preferably 4 to 15% by weight. Compound (c-4) may be a salt with the above-mentioned acid or base.

The plant growth regulator of the present invention may contain one or more of the above plant growth regulators or salts thereof. The plant growth regulator of the present invention may be the above-mentioned plant growth regulator itself, or may be formulated into a carrier such as a wettable powder, an emulsion, a granule, and a powder, which is used in a usual plant growth regulator.

For example, solid carriers include mineral powders (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate, phosphorus lime, etc.) and vegetable powders (soybean flour, flour, wood, etc.). Powder, tobacco powder, starch, crystalline cellulose and the like), high molecular compounds (petroleum resin, polyvinyl alcohol resin, polyvinyl acetate resin, polyvinyl chloride, ketone resin and the like), and alumina, waxes and the like can be used. As the liquid carrier, for example, alcohols (methanol, ethanol, propanol, butanol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (toluene, benzene, xylene, etc.), chlorinated hydrocarbons (chloroform, Carbon tetrachloride, monochlorobenzene, etc., ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexane, etc.), esters (ethyl acetate, butyl acetate, etc.), acid amides (N, N-dimethylacetamide) ), Ether alcohols (such as ethylene glycol ethyl ether), or water.

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 alkyl aryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester,
Polyoxyethylene sorbitan fatty acid ester, oxyethylene polymer, oxypropylene polymer, polyoxyethylene alkyl phosphate, fatty acid salt, alkyl sulfate, alkyl sulfonate, alkyl aryl sulfonate, alkyl phosphate, alkyl phosphate Ester salts, polyoxyethylene alkyl sulfates, quaternary ammonium salts, oxyalkylamines,
Lecithin, saponin and the like. Also, if necessary, gelatin, casein, sodium alginate, starch, agar,
Polyvinyl alcohol or the like can be used as an auxiliary.

There is no limitation on the shape of the preparation, and powders, granules,
It can be formed into any formulation such as granules, wettable powders, flowables, emulsions and pastes. The plant growth regulator of the present invention can be produced by mixing and stirring the above-mentioned plant growth regulator and other components according to a conventional method.

The plant growth regulator of the present invention has an effect of increasing the amount of roots and an effect of suppressing elongation of stems, and is particularly preferably used as an agent for promoting rooting.

When the plant growth regulator of the present invention is used,
It may be used directly as it is, or may be used after being diluted or suspended to a predetermined concentration with water.

When applied to plants, they can be used as soil treatment agents, foliage treatment agents, seed treatment agents before sowing, treatment agents for plants before transplantation, treatment agents for plants at the time of transplantation, and the like. In hydroponics, it may be used by mixing with a hydroponic solution, and in tissue culture, it may be used by suspending or dissolving it in a medium.

When the plant growth regulator of the present invention is used for spraying, the concentration used is preferably 0.01 to 1000.
The range may be 0 ppm, more preferably 1 to 5000 ppm, and particularly preferably 5 to 1000 ppm. In particular, when used for seedlings in the seedling raising stage, it is desirable to apply 50 to 200 ml of the diluted solution having the above concentration per liter of culture soil. In this case, a spreading agent may be used, and the type and amount of the spreading agent used are not particularly limited.

The amount used when applied directly to soil, including when mixed with fertilizers, is 10 ha / ha.
It is preferable to use 0 to 10000 g, particularly 500 to 5000 g. In particular, when used for seedlings in the nursery stage, culture soil 1
It is desirable to use 0.001 to 10 g per liter. In this case, the seeds may be previously mixed 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, methylene chloride, etc.), ethers (diethyl ether, etc.) It can also be diluted with a liquid carrier such as an ester (such as ethyl acetate) so as to have a concentration of 0.01 to 100000 ppm and sprayed on a dry seed, or immersed in a diluent to absorb the dry seed. The immersion time is not particularly limited, but is preferably 1 second to 30 minutes. Further, the treated seed may be subjected to air drying, reduced pressure drying, heat drying, vacuum drying, or the like to evaporate the liquid carrier. In addition, a formulation prepared using a solid carrier of a mineral substance powder such as clay can be used by attaching it to the seed surface. The seeds can also be mixed with commonly used seed coating agents and seed coating films to coat the seeds.

When used during tissue culture or cell culture,
It is dissolved or suspended in a commonly used plant tissue culture medium (MS medium, white medium, Gamborg's B5 medium, etc.) at a concentration of preferably 0.01 to 10000 ppm, particularly preferably 0.1 to 1000 ppm as the concentration in the medium. Can be used. In this case, saccharides (sucrose, glucose, etc.) as carbon sources, cytokinins (benzyladenine, kinetin, etc.), auxins (indole acetic acid,
Naphthalene acetic acid, etc.), gibberellin (GA3, GA4, etc.), abscisic acid, and the like can be appropriately added.

In the case of directly absorbing the plant before transplantation, the root or the whole of the plant can be used by immersing it in a solution diluted or suspended at a working concentration of 0.1 to 1000 ppm. In the case of cuttings, cuttings, cuttings, etc., the base or the whole can be immersed for use. In this case, the immersion time is desirably 1 second to 1 week, particularly 1 minute to 3 days. In addition, a preparation prepared using a solid carrier of mineral powder may be attached to the root or, in the case of cuttings, cuttings, cuttings, etc., to the stem base.

The plant growth regulator of the present invention can be administered at any time during the growth period.
Especially when applied as a rooting promoter, root growth is inhibited or root failure occurs before sowing, during sowing, when raising seedlings, before and after work involving cultivated rooting such as transplantation, or due to weather factors. This is particularly effective in the case where it is performed.

When the plant growth regulator of the present invention is applied to a plant, the root mass and root density increase through an increase in the number of roots such as the number of lateral roots and the number of adventitious roots. The effects of raising seedlings, promoting growth, improving water absorption, improving fertilizer absorption, improving fertilizer component utilization, retaining green, improving photosynthetic ability, improving water stress resistance, preventing lodging, increasing yield, and the like are obtained.

The plant to which the plant growth regulator of the present invention is applied is not particularly limited.
Eggplants such as peppers, peppers and eggplants, cucumber, cucumber, pumpkin, melon, watermelon etc., raw and spicy vegetables such as celery, parsley, lettuce, green onions such as leek, onion, garlic, soybean, peanut, kidney beans , Peas, beans such as adzuki beans, other fruits and vegetables such as strawberries, direct roots such as radish, turnip, carrot, burdock, taro,
Potatoes such as cassava, potato, sweet potato, and potato; soft vegetables such as asparagus, spinach, and honey;
Eustoma, stocks, carnations, flowers such as chrysanthemums, cereals such as rice and corn, grasses such as bentgrass and corngrass, oil crops such as rapeseed and sunflower, sugar crops such as sugar cane and sugar beet, cotton,
Fiber crops such as rush, forage crops such as clover, sorghum, and dent corn; deciduous fruit trees such as apple, pear, grape, and peach; citrus fruits such as unshiu mandarin, lemon, grapefruit, citrus, azalea, cedar, etc. Woody species.

Among these, tomato, pepper, capsicum, eggplant, cucumber, pumpkin, melon, watermelon, celery, parsley, lettuce, green onion, onion, asparagus, eustoma, stock, rice, bentgrass, corngrass, sugar beet, etc. Plants to be transplanted during cultivation, chrysanthemums, carnations, satsuki, azaleas,
It is particularly effective for plants that proliferate by rooting from cut branches or cuttings such as grapes.

For the purpose of improving the effects of the present invention, it can be used in combination with other plant growth regulators, and in some cases, a synergistic effect can be expected. For example, when raising seedlings under conditions that are extremely prone to growth, 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 low underground part weight ratio. It may be used in combination with an anti-gibberellin agent (paclobutrazol, uniconazole P, ancimidol and the like), a growth inhibitor (daminozide and the like), and an ethylene generator (ethephon and the like). In addition, in cuttings, cuttings, cuttings and tissue culture, auxin-based compounds (such as indoleacetic acid, indolebutyric acid, naphthyl acetamide, naphthalene acetic acid) may be used in combination for the purpose of enhancing rooting promoting effect. Further, at the time of seed treatment before sowing, it may be used in combination with a gibberellin agent having a germination promoting action. These are merely examples, and other plant growth regulators that can be used in combination with the plant growth regulator of the present invention are not limited to these.

The plant growth regulator of the present invention can be mixed with 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 it in combination with hydroxyisoxazole, metasulfocarb, metalaxyl, etc., which have been reported to have a rooting promoting effect in addition to the bactericidal effect. In addition, it is particularly effective to use it together with the insecticide fungicide used during the seedling raising period. When used in combination with a fertilizer, it is particularly effective to use the fertilizer in combination with a fertilizer for raising seedlings for the purpose of growing healthy seedlings, and with a fertilizer applied immediately before transplantation for the purpose of promoting survival. It is also particularly effective to mix the plant growth regulator of the present invention with a slow-release fertilizer for the purpose of maintaining the efficacy of the plant growth regulator for a long period of time and improving the utilization rate of fertilizer components.

[0064]

Next, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to the following Examples.

Production Example 1 5-oxo-5-[[2- (3-indolyl) ethyl]
Synthesis of amino] -valeric acid (compound 01) To 20.0 g of tryptamine, 100 ml of acetone was added and dissolved. While stirring at room temperature, a solution prepared by dissolving 14.2 g of glutaric anhydride in 100 ml of acetone was added, followed by stirring for 4 hours after addition. did. The solvent was removed under reduced pressure, and the residue was dissolved with a 5% aqueous sodium hydrogen carbonate solution and ethyl acetate, and separated in a separating funnel. After discarding the ethyl acetate layer, the aqueous phase was adjusted to pH 2.5 using concentrated hydrochloric acid, and extracted with ethyl acetate. After the ethyl acetate layer was dehydrated with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, acetone was added to the residue, and the mixture was allowed to cool at -10 ° C. The obtained crystals were repeatedly recrystallized twice with acetone, and the obtained crystals were dried under reduced pressure to obtain 14.8 g of Compound 01.

Production Example 2 5-oxo-5-[[2- (3-indolyl) ethyl]
Synthesis of Amino] -Methyl Valerate (Compound 02) To 10.0 g of tryptamine, 100 ml of methylene chloride was added and dissolved, and triethylamine 8.8 was stirred with ice cooling.
ml was added and further stirred. To this, 8.7 ml of glutaric acid methyl chloride dissolved in 25 ml of methylene chloride was added and stirred for 4 hours. After completion of the reaction, methylene chloride and water were added and the mixture was separated.
The mixture was washed sequentially with a 10% aqueous sodium hydrogen carbonate solution and water. The methylene chloride phase was dehydrated with anhydrous magnesium sulfate and dried, then, methylene chloride was distilled off under reduced pressure, acetone was added to the residue, and the mixture was allowed to cool at -10 ° C. The obtained crystals were repeatedly recrystallized twice with acetone, and the obtained crystals were dried under reduced pressure.
12.4 g of compound 02 were obtained.

Production Example 3 5-oxo-5-[[2- (3-indolyl) ethyl]
Synthesis of Amino] -ethyl valerate (Compound 03) To 5.0 g of Compound 01 was added 60 ml of ethanol, 0.35 g of paratoluenesulfonic acid was added with stirring at room temperature, and the mixture was heated to 71-74 ° C and heated for 1 hour. Stirred. After cooling,
The solvent was distilled off under reduced pressure, methylene chloride and water were added, and the mixture was separated.
Washed sequentially with water. The methylene chloride phase was dehydrated with anhydrous magnesium sulfate and dried, then, methylene chloride was distilled off under reduced pressure, acetone was added to the residue, and the mixture was allowed to cool at -10 ° C.
The obtained crystals were repeatedly recrystallized twice with acetone, and the obtained crystals were dried under reduced pressure to obtain 4.1 g of Compound 03.

Production Example 4 5-oxo-5-[[2- (3-indolyl) ethyl]
Synthesis of n-propyl amino] -valerate (Compound 04) 4.79 g of Production Example 3 was prepared in the same manner as in Production Example 3 except that 120 ml of n-propanol was used instead of ethanol and the mixture was heated to 78-80 ° C. Compound 04 was obtained.

Production Example 5 Synthesis of 5-oxo-5-[[(1-naphthyl) methyl] amino] -valeric acid (Compound 05) In Production Example 1, 25 g of 1-naphthalenemethylamine was used in place of tryptamine. 1 glutaric anhydride
29.5 g in the same manner as in Production Example 1 except that the amount was 8.2 g.
Compound 05 was obtained.

Preparation Example 6 Synthesis of methyl 5-oxo-5-[[(1-naphthyl) methyl] amino] -valerate (Compound 06) In Preparation Example 2, 5 g of 1-naphthalenemethylamine was used in place of tryptamine. , Triethylamine 4.
3.28 g of compound 06 was obtained in the same manner as in Production Example 2 except that 5 ml and glutaric acid methyl chloride were used in 4.4 ml.

Preparation Example 7 Synthesis of ethyl 5-oxo-5-[[(1-naphthyl) methyl] amino] -ethyl valerate (Compound 07) In Preparation Example 3, 10 g of Compound 05 was used in place of Compound 01. Then, 4.27 g of compound 07 was obtained in the same manner as in Production Example 3 except that ethanol was changed to 100 ml and paratoluenesulfonic acid was changed to 0.7 g.

Production Example 8 Synthesis of n-propyl 5-oxo-5-[[(1-naphthyl) methyl] amino] -valerate (Compound 08) In Production Example 3, 120 ml of n-propanol was used instead of ethanol. 0.7 g of paratoluenesulfonic acid
3.52 g of compound 08 was obtained in the same manner as in Production Example 3 except that the mixture was heated to 78 to 80 ° C.

Production Example 9 Synthesis of 5-oxo-5-[[2- (1-naphthyl) ethyl] amino] -valeric acid (compound 09) [2- (1-Naphthyl) ethyl] amine hydrochloride (25 g) and acetone 300 ml was added and suspended, and 16.9 ml of triethylamine was further added. A solution obtained by dissolving 15.2 g of glutaric anhydride in 100 ml of acetone was added with stirring at room temperature. After the addition, the mixture was stirred overnight. The solvent was removed under reduced pressure, and the residue was dissolved with a 5% aqueous sodium hydrogen carbonate solution and ethyl acetate, and separated in a separating funnel. After discarding the ethyl acetate layer, the aqueous phase was adjusted to pH 2.5 using concentrated hydrochloric acid, and extracted twice with ethyl acetate. After the ethyl acetate layer was dehydrated with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, acetone was added to the residue, and the mixture was allowed to cool at -10 ° C.
The obtained crystal was repeatedly recrystallized twice with acetone, and the obtained crystal was dried under reduced pressure to obtain 19.7 g of Compound 09.

Production Example 10 Synthesis of methyl 5-oxo-5-[[2- (1-naphthyl) ethyl] amino] -valerate (Compound 10) In Production Example 2, [2- (1-
[Naphthyl) ethyl] amine hydrochloride was used in an amount of 7.4 g in the same manner as in Production Example 2 except that 13.5 ml of triethylamine and 6.7 ml of methyl glutarate were used.
g of compound 10 were obtained.

Production Example 11 4-oxo-4-[[2- (3-indolyl) ethyl]
Synthesis of Amino] -butyric acid (Compound 11) 3.28 g of Compound 11 was prepared in the same manner as in Production Example 1 except that tryptamine was changed to 10 g in Example 1 and 6.25 g of succinic anhydride was used instead of glutaric anhydride. Obtained.

Preparation Example 12 Synthesis of 4-oxo-4-[[(1-naphthyl) methyl] amino] -butyric acid (Compound 12) In Preparation Example 11, 5 g of 1-naphthalenemethylamine was used in place of tryptamine, and anhydrous succinic acid was used. 3.18 acids
In the same manner as in Production Example 13, except that the amount was changed to 0.9 g, Compound 12 (0.96 g) was obtained.

Production Example 13 Synthesis of (Z) -4-oxo-4-[[(1-naphthyl) methyl] amino] -butenoic acid (compound 13) 10 ml of 1-naphthalenemethylamine and 100 ml of acetone
Then, a solution prepared by dissolving 6.4 g of maleic anhydride in 50 ml of acetone was added thereto while stirring under ice-cooling, and the mixture was stirred for 5 hours after the addition. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified and recrystallized in the same manner as in Production Example 1 to give 5.75 g.
Compound 13 was obtained.

Production Example 14 Synthesis of 5-oxo-5-[[2- (5-methyl-3-indolyl) ethyl] amino] -valeric acid (Compound 14) In Production Example 9, [2- (1-naphthyl) [2- (5-Methyl-3-indolyl) ethyl] amine hydrochloride (2 g) was used in place of [ethyl] amine hydrochloride, and triethylamine (1.33 ml) and glutaric anhydride (1.19 g) were used. The reaction time was further 5 hours. 1.38 g of compound 14 was obtained in the same manner as in Production Example 9 except that the above was changed.

Preparation Example 15 Synthesis of methyl 3-oxo-3-[[(1-naphthyl) methyl] amino] -propionate (Compound 15) In Preparation Example 2, 20 ml of 1-naphthalenemethylamine was used in place of tryptamine. , Triethylamine to 2
9.9 g of Compound 15 was obtained in the same manner as in Production Example 2 except that 0 ml and 15.4 ml of methyl malonate were used instead of methyl glutarate chloride.

Production Example 16 Synthesis of 3-oxo-3-[[(1-naphthyl) methyl] amino] -propionic acid (Compound 16) To 10 g of Compound 15 was added 50% ethanol containing 0.3 N sodium hydroxide. Heat to 80-81 ° C and add 14
Stirred for 0 minutes. After cooling, the solvent was distilled off under reduced pressure, water was added, and the mixture was adjusted to pH 8.0 with sodium hydroxide.
Ethyl acetate was added and the layers were separated. After discarding the ethyl acetate phase, the aqueous phase was adjusted to pH 2.5 with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate phase was dehydrated with anhydrous magnesium sulfate and dried, then, ethyl acetate was distilled off under reduced pressure, acetone was added to the residue, and the mixture was allowed to cool at 5 ° C. The obtained crystal was repeatedly recrystallized twice with acetone, and the obtained crystal was dried under reduced pressure to obtain 3.6 g of Compound 16.

Preparation Example 17 Synthesis of (Z) -4-oxo-[[2- (3-indolyl) ethyl] amino] -butenoic acid (Compound 17) In Preparation Example 13, tryptamine was used in place of 1-naphthaleneethylamine. Production Example 1 except that 4 g was used
In a similar manner to 3, 4.6 g of compound 17 was obtained.

Production Example 18 Synthesis of 3-oxo-3-[[2- (1-naphthyl) ethyl] amino] -propionic acid (compound 18) Chloride to 20 g of [2- (1-naphthyl) ethyl] amine hydrochloride 200 ml of methylene was added and dissolved, and 28.3 ml of triethylamine was added while stirring under ice cooling, followed by further stirring. To this, 10.8 ml of malonic acid methyl chloride dissolved in 100 ml of methylene chloride was slowly added dropwise so that the liquid temperature did not exceed 5 ° C, and the mixture was further stirred for 2 hours. After completion of the reaction, methylene chloride and water were added thereto, and the mixture was separated.
Washed sequentially with water. The methylene chloride phase was dehydrated with anhydrous magnesium sulfate and dried, and then methylene chloride was distilled off under reduced pressure. The residue was dissolved in 100 ml of 50% aqueous ethanol containing 0.5 N sodium hydroxide, heated to 79 ° C.
Minutes. After cooling, ethanol was distilled off under reduced pressure,
After adding water, the pH was adjusted to 8.0, ethyl acetate was added, and the mixture was separated. After discarding the ethyl acetate phase, the aqueous phase was adjusted to pH 2.5 and extracted with ethyl acetate. The ethyl acetate phase was dehydrated with anhydrous magnesium sulfate and dried, and then ethyl acetate was distilled off under reduced pressure. Acetone was added to the residue, and the mixture was left standing and cooled at 5 ° C. The obtained crystals were repeatedly recrystallized three times with acetone, and the obtained crystals were dried under reduced pressure to obtain 6.9 g of Compound 18.
I got

Production Example 19 3-oxo-3-[[2- (3-indolyl) ethyl]
Synthesis of amino] -propionic acid (compound 19) In Production Example 18, 20 g of tryptamine was used instead of [2- (1-naphthyl) ethyl] amine hydrochloride, 17.4 ml of triethylamine and 14.4 of methyl malonate were used. 2.4 g of compound 19 was obtained in the same manner as in Production Example 18 except that the amount was 7 ml.

Production Example 20 Synthesis of ethyl 5-oxo-5-[[2- (1-naphthyl) ethyl) amino] -ethyl valerate (Compound 20) 5.0 g of Compound 09 was dissolved in 60 ml of ethanol, and the mixture was dissolved at room temperature. While stirring, 0.33 g of paratoluenesulfonic acid was added, the mixture was heated to 71 to 74 ° C, and stirred for 1 hour. After cooling, the solvent was distilled off under reduced pressure, methylene chloride and water were added, and the mixture was separated. The methylene chloride phase was washed successively with a 5% aqueous sodium hydrogen carbonate solution and water. The methylene chloride phase was dehydrated with anhydrous magnesium sulfate and dried, and then methylene chloride was distilled off under reduced pressure. The obtained residue was 227 to 2 under reduced pressure of 1.5 mmHg.
The mixture was heated and distilled at 35 ° C. to obtain 1.9 g of Compound 20.

Production Example 21 Synthesis of 5-oxo-5-[[(1-naphthyl) methyl] amino] -pentanamide (Compound 21) To 10 g of Compound 05 was added 50 ml of thionyl chloride to dissolve and dissolved at room temperature. Stirred for minutes. Thionyl chloride was distilled off under reduced pressure, and 20 ml of acetone was added thereto and dissolved.
The mixture was added dropwise to ice-cooled 25% ammonia water and stirred for 20 minutes under ice cooling. After the precipitated crystals were collected by filtration, ethyl acetate and 1N aqueous hydrochloric acid were added to carry out liquid separation. After discarding the ethyl acetate phase, the aqueous phase was adjusted to pH 8.0 and extracted with ethyl acetate.
The ethyl acetate phase is dehydrated with anhydrous magnesium sulfate, dried,
Ethyl acetate was distilled off under reduced pressure. Acetone and methanol were added to the residue, and the mixture was left standing and cooled at -60 ° C. The obtained crystals were repeatedly recrystallized three times with a mixed solution of acetone and methanol, and the obtained crystals were dried under reduced pressure.
Compound 20 was obtained.

The physical properties of the compounds 01 to 21 obtained above are shown in Tables 1 to 4.

[0087]

[Table 1]

[0088]

[Table 2]

[0089]

[Table 3]

[0090]

[Table 4]

Example 1 Rooting promotion action by adzuki bean cut chemical solution immersion treatment Usually used seedling raising box (35 cm × 25 cm × 5 c deep)
m) filled with vermiculite (manufactured by Kushiro Coal Retoring Co., Ltd.) and adzuki seeds (variety name: Erimoshozu,
Snow Seed Seedling Co., Ltd.) was sown and cultivated under continuous light (2200 lux, 20 ° C.) using a fluorescent lamp for 12 days. The fully developed primary leaves were cut off at a height of 3 cm, and the shoots at the shoot apex were also cut off to prepare test materials. Production Examples 1 to 21
Of the 21 types of plant growth regulators produced in the above, compounds 02 to 04, 06 to 08, 10, 15, 20, and 21 were diluted with distilled water, and the others were distilled while neutralizing with sodium hydroxide. Diluted with water, 8ppm, 80p
A solution of pm was prepared. Ethanol was appropriately added to the hardly soluble compound so that the final concentration was 1% or less. The cut ends of the above-described test materials of adzuki beans were immersed in these solutions for 72 hours. After the treatment, the adzuki bean slices were washed with their bases, immersed in distilled water for 4 days and cultured, and the number of adventitious roots generated was measured in 5 replicates. In addition,
As a control, the cells were treated with distilled water and cultured similarly, and the number of adventitious roots was measured. The results are shown in Tables 5 and 6. The adzuki bean treated with the plant growth regulator showed a remarkably higher rooting number than the control. Especially concentration 8
At ppm, compounds 07 to 09 and 20 have high rooting promoting activity, and at 80 ppm, compounds 01 to 03 and 0
5, 17, 19 and 21 had high rooting promoting activities. In Tables 5 and 6, the relative value refers to the number of roots of the control of 10
The rooting number in the case of 0 is expressed in%.

[0092]

[Table 5]

[0093]

[Table 6]

Example 2 Comparison of root-promoting action with auxin by adzuki bean cut chemical solution immersion treatment Compounds 01 and 05 shown in Production Examples 1 and 5 and a control were known to have root-promoting action. The indole acetic acid, which is an auxin compound, was diluted with distilled water to various concentrations while neutralizing with an aqueous sodium hydroxide solution as in Example 1. The test for rooting promoting action was performed under the same conditions as in Example 1. As shown in Table 7, the compound 01 was at a concentration of 10 ppm or more, and the compound 05 was at a concentration of 30 ppm or more, and the number of roots was larger than that of indoleacetic acid. Note that the relative value is the rooting number as a percentage when the rooting number of the control is 100.

[0095]

[Table 7]

Example 3 Action of Promoting Upgrowth by Application of Radish Cotyledon Coat Treatment in a pot having a size of 3 cm in diameter and a height of 5 cm in a special culture soil containing peat as a main component (Scotts, Scotts-Sierra Horticul)
radish seeds (variety name: Harukafuta, sold by Snow Brand Seed Co., Ltd.) in a room at 25 ° C. under continuous light (2200 lux, 20
C). On day 4 after sowing, compound 01 and compound 05 diluted to a predetermined concentration were applied to the entire left and right cotyledons of the test seedling in an amount of 10 μl each, and 5 μl was further applied to the petiole.
1 was applied. In addition, distilled water was similarly treated as a control. Twenty-four hours after the treatment with the reagent, the test seedling is cut off from the base with scissors, cut on both sides along the middle rib of the cotyledon, the shadow is copied, and the bending angle of the tip of the leaf is determined by the Rafanas test A method [Takematsu, Plant Chemistry. Adjustment Volume 2: 132-141 (196
7)]. The results are shown in Table 8. Indolebutyric acid has a concentration of 50 ppm or more, and naphthylacetic acid has a concentration of 10 ppm.
At a concentration of ppm or more, the flexion angle exceeded 150 °, and remarkable upgrowth of cotyledons was observed. In contrast, Compound 0
In the case of Compound No. 1 and Compound 05, the bending angle did not exceed 70 ° even in the concentration range of 10 to 1000 ppm, and no upward growth that would be a problem in raising seedlings was observed.

[0097]

[Table 8]

Example 4 Effect of Cabbage on Cell-Forming Seedlings and Seedlings Using a hard plastic cell tray with a size of 1 hole of 4 cm × 4 cm and 128 holes, a dedicated culture soil mainly composed of peat (Scotts, Scotts-Sierra Horticultural Products)
And cabbage (variety Early Ball, sold by Sakata Corporation) were sown in a glass house, and cultivated with additional fertilization as appropriate. On day 10 and day 18 after seeding, compound 0 diluted to a predetermined concentration in the same manner as in Example 2
1, 500 ml of compound 05 and indolebutyric acid, an auxin compound, were sprayed per tray. Deionized water was used as a control. Twenty-four days after sowing, 8 individuals × 2 repetitions were sampled, and the plant height and root dry weight were measured.
The results are shown in Table 9. In addition, the numerical value in the parenthesis in a table | surface shows the relative value when the control group is set to 100 by%. The root dry weight increased in the 100 ppm and 1000 ppm treatments of compound 01 and in the treatments of all concentrations of compound 05, indicating that the root-promoting effect was high even in cabbage seedlings grown by a practical method. . The total dry weight is 10 ppm of compound 01 and compound 05, 100
It increased in the ppm treated area, and a growth promoting effect was also observed. In addition, the effect of shortening the plant height was also observed in the groups treated with the compound 01 and the compound 05 at 1000 ppm. Since these effects such as an increase in root mass, promotion of growth and suppression of growth are desirable at the time of raising seedlings, the usefulness of Compound 01 and Compound 05 was confirmed. On the other hand, indolebutyric acid, which was used as a control, caused phytotoxicity in the 1000 ppm treatment, and no effect on the dry weight of the root was observed in the treatments of other concentrations.

[0099]

[Table 9]

Example 5 Effect of Chrysanthemum on Cutting and Propagating Seedlings The parent strain of chrysanthemum (cultivar name: Hideyoshi's power, sold by Yamate Shuhoen) was excised at a position of about 7 cm at the tip of the stem, and further settled on the lower part. Two leaves were excised and used as cuttings. Compounds 01 and 05 were diluted with distilled water while adding ethanol so that the final concentration was 5% or less, and further neutralizing with sodium hydroxide.
The solutions were adjusted to 100 ppm and 1000 ppm, respectively. The cut ends of the cuttings were immersed in these solutions for 72 hours. After the treatment, the cuttings were mixed with fine-grained Kanuma soil and rice husk charcoal in a ratio of 2 to 1 and cut into a nursery box filled with a depth of 5 cm to sprout. Then, after raising the seedlings in a greenhouse for 30 days, the number of roots was measured by 5 individuals × 2 repetitions, the total root length was measured with a root scanner (manufactured by Comair), and the roots were measured after being dried. The results are shown in Table 10. It was found that the chrysanthemum treated with this plant growth regulator significantly increased the number of roots and the total root length as compared with the control group. Compound 01 also increased the root weight.

[0101]

[Table 10]

[0102]

EFFECT OF THE INVENTION The plant growth regulator of the present invention has a high activity of promoting rooting of plants and has extremely weak side effects such as an upward growth of leaves, so that it can be used as a plant growth regulator, particularly as a rooting promoting agent. It can be used over the entire growing period, and is particularly useful as a rooting promoting agent during the seedling raising and transplanting periods. It can also be used by adding it to a medium for the purpose of root differentiation in plant tissue culture.

Continuation of the front page (72) Inventor Tamji Sugiyama 3-1-1, Someji, Choji-shi, Tokyo Tamagawa Housing 6-305 room

Claims (7)

[Claims] [Claim 1] The following general formula (1) (In the formula, R ¹ represents a 3-indolyl group or a 1-naphthyl group which may have a substituent, A represents a linear or branched lower alkylene group, and B represents a substituent. A good linear or branched lower alkylene group or lower alkenylene group, and R ² represents a hydroxy group, a lower alkoxy group or an amino group) or a salt thereof as a plant growth regulator. . 2. R ¹ is a 3-indolyl group, 5-methyl-
A is a methylene group or an ethylene group, B is a linear alkylene group having 1 to 3 carbon atoms or a vinylene group; R ² is a hydroxy group, an amino group, a methoxy group; The plant growth regulator according to claim 1, which is a group, an ethoxy group, an n-propoxy group, an n-butoxy group or an n-pentyloxy group. 3. R ¹ , A, B and R ² each represent a 3-indolyl group, an ethylene group, a methylene group or a hydroxy group;
3-indolyl, ethylene, methylene, methoxy; 3-indolyl, ethylene, ethylene, hydroxy; 3-indolyl, ethylene, ethylene, methoxy; 3-indolyl, ethylene, Trimethylene group, hydroxy group; 3-indolyl group, ethylene group, trimethylene group, methoxy group; 3-indolyl group, ethylene group, trimethylene group, ethoxy group; 3-indolyl group, ethylene group, trimethylene group, n-propoxy group; 3-indolyl group, ethylene group, cis-vinylene group, hydroxy group; 5-methyl-3-indolyl group, ethylene group, trimethylene group, hydroxy group; 1-
Naphthyl group, methylene group, methylene group, hydroxy group;
1-naphthyl group, methylene group, methylene group, methoxy group; 1-naphthyl group, methylene group, ethylene group, hydroxy group; 1-naphthyl group, methylene group, ethylene group, methoxy group; 1-naphthyl group, methylene group, Trimethylene group, hydroxy group; 1-naphthyl group, methylene group, trimethylene group, methoxy group; 1-naphthyl group, methylene group, trimethylene group, ethoxy group; 1-naphthyl group, methylene group, trimethylene group, n-propoxy group; 1-naphthyl group, methylene group, trimethylene group, n-butoxy group; 1-naphthyl group, methylene group, trimethylene group, n
1-naphthyl group, methylene group, trimethylene group, amino group; 1-naphthyl group, methylene group, cis-vinylene group, hydroxy group; 1-naphthyl group, ethylene group, methylene group, hydroxy group; 1-naphthyl group, ethylene group, methylene group, methoxy group; 1-naphthyl group, ethylene group, ethylene group, hydroxy group;
-A naphthyl group, an ethylene group, an ethylene group, a methoxy group;
1-naphthyl group, ethylene group, trimethylene group, hydroxy group; 1-naphthyl group, ethylene group, trimethylene group, methoxy group; 1-naphthyl group, ethylene group, trimethylene group, ethoxy group; 1-naphthyl group, ethylene group,
Trimethylene group, n-propoxy group; 1-naphthyl group,
Ethylene group, trimethylene group, n-butoxy group; 1-naphthyl group, ethylene group, trimethylene group, n-pentyloxy group; or 1-naphthyl group, ethylene group, cis-
The plant growth regulator according to claim 1, which is a vinylene group or a hydroxy group. 4. The plant growth regulator according to claim 1, which is a plant rooting promoter. 5. The following general formula (2): (Wherein D represents a methylene group or an ethylene group, E represents a methylene group, an ethylene group, a trimethylene group or a vinylene group, and R ³ represents a hydroxy group, a methoxy group, an ethoxy group, an n-propoxy group, or an n-butoxy group. group, a n- pentyloxy group or an amino group. provided that R ³ when D is a methylene group is and E is ethylene group is a methoxy group and D, R ³ when E both ethylene groups are hydroxy groups An amide derivative represented by the formula: 6. D, E and R ³ each represent a methylene group, a methylene group, a hydroxy group; a methylene group, a methylene group, a methoxy group; a methylene group, an ethylene group, a methoxy group; a methylene group, a trimethylene group, a hydroxy group; Methylene group, trimethylene group, methoxy group; methylene group, trimethylene group, ethoxy group; methylene group, trimethylene group, n-propoxy group; methylene group, trimethylene group,
n-butoxy group; methylene group, trimethylene group, n-pentyloxy group; methylene group, trimethylene group, amino group; methylene group, vinylene group, hydroxy group; ethylene group, methylene group, hydroxy group; ethylene group, methylene group; Methoxy group; ethylene group, ethylene group, hydroxy group; ethylene group, trimethylene group, hydroxy group; ethylene group, trimethylene group, methoxy group; ethylene group, trimethylene group, ethoxy group; ethylene group, trimethylene group, n-propoxy group; Ethylene group, trimethylene group,
The amide derivative according to claim 5, which is an n-butoxy group; an ethylene group, a trimethylene group, an n-pentyloxy group; or an ethylene group, a vinylene group, or a hydroxy group. 7. 3-oxo-3-[[2- (3-indolyl) ethyl] amino] -propionic acid, 5-oxo-
5-[[2- (3-Indolyl) ethyl] amino] -methyl valerate, 5-oxo-5-[[2- (3-Indolyl) ethyl] amino] -n-propyl valerate or 5-oxo- 5-[[2- (5-Methyl-3-indolyl) ethyl] amino] -valeric acid.