JP4087942B2 - Plant growth regulator - Google Patents

Description

[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a plant growth regulator having high plant rooting promoting activity and useful as an agrochemical or fertilizer additive.
[0002]
[Prior art and problems to be solved by the invention]
In the agricultural field, controlling plant growth is an important technique for improving productivity. Control of growth by plant nutritional methods was performed mainly by applying chemical fertilizers as appropriate, and the spread of this technology dramatically increased crop yield. On the other hand, in recent years, growth control using various types of plant growth regulators has already been put into practical use, and it is known that it contributes to the improvement of yield and product quality.
[0003]
By the way, plant roots absorb various water and nutrients necessary for growth, support the above-ground part, prevent lodging, and supply the above-ground plant hormones essential for the healthy growth of plants. It is known to carry out various functions. [Waisel et al., Plant Roots-The Hidden Half- (1991)]. In particular, in transplantation cultivation, it is important to grow seedlings that have a large amount of roots during the seedling raising period and quickly root after planting. From these facts, the importance of sufficiently developing plant roots in the agricultural field has been pointed out in the past [Edited by Boote et al., Physiology and Determination of Crop Yield 65-93 (1994)].
[0004]
Conventionally, as techniques for promoting root growth, generally, moisture, temperature and fertilization management during cultivation, soil composition, soil improvement, etc. are mainly used, and sufficient effects are not necessarily obtained. Is the current situation. In addition, although a method using a plant growth regulator can be considered, auxin compounds such as indolebutyric acid, naphthylacetic acid, and naphthylacetamide, which are put into practical use as rooting promoters, depend on the type and state of the plant and the concentration applied. Undesirable effects such as epidermal bending, stem torsion and stem cracking, and even death may occur. For this reason, at the time of general seedling raising, the method of use, the amount of use, etc. were restricted, and the action of promoting root development was not fully satisfactory.
[0005]
Also, in plant tissue culture, it is common to add auxin compounds to the medium when it is desired to induce root differentiation. However, depending on the type of plant and the culture state, the root may not be induced or induced. The rate was extremely low, which was a problem. In this way, from the viewpoint of planting seedlings, seedling production, establishment of turf vegetation, etc., and use in tissue culture, the plant rooting promotion activity is high, and it has virtually no side effects such as the leaf overgrowth action. There has been a demand for a plant growth regulator that is completely different from conventional auxin compounds.
[0006]
[Means for Solving the Problems]
As a result of diligent research to solve such problems, the present inventors have surprisingly found that the compound represented by the following general formula (1) shows substantially no side effects such as the growth on the leaves, And it discovered that the rooting promotion activity of a plant was high, and came to complete this invention based on this knowledge.
[0007]
That is, the present invention provides the following general formula (1)
[0008]
[Chemical 2]
[0009]
(In the formula, Ar represents an optionally substituted phenyl group, A represents a linear or branched lower alkylene group, and B represents a linear or branched lower alkylene group or lower alkenylene group. R ¹ Represents a hydroxyl group, an amino group or a lower alkoxyl group)
The plant growth regulator which uses the compound represented by these, or its salt as an active ingredient is provided.
[0010]
DETAILED DESCRIPTION OF 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.
[0011]
In the general formula (1), the phenyl group which may have a substituent represented by Ar is, for example, 1 selected from a halogen atom, a hydroxyl group, a nitro group, a lower alkyl group and a lower alkoxyl group on the benzene ring. The phenyl group which -5 groups may be substituted is mentioned. The group represented by Ar is represented by the general formula (2).
[0012]
[Chemical 3]
[0013]
(Wherein R ² , R ^Three , R ^Four , R ^Five And R ⁶ Are the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a lower alkyl group, or a lower alkoxyl group. )
[0014]
Here, the lower alkyl group includes a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an i-pentyl group, and an i-pentyl group. -C1-C6 alkyl groups, such as a hexyl group, are mentioned, Among these, a methyl group is especially preferable. Moreover, as a lower alkoxyl group, a methoxy group, an ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, i-pentyloxy group C1-C6 alkoxyl groups, such as i-hexyl group, are mentioned, Among these, a methoxy group is especially preferable. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
[0015]
When these phenyl groups have a substituent, the substitution position may be any of the 2-6 positions, but is preferably the 2-position, 3-position and / or 4-position.
[0016]
More preferable Ar includes a phenyl group which may be substituted at the 2-position, 3-position and / or 4-position with a group selected from a halogen atom, hydroxyl group, nitro group, methyl group and methoxy group.
[0017]
A is a linear or branched lower alkylene group, and examples thereof include alkylene groups having 1 to 6 carbon atoms such as methylene group, ethylene group, trimethylene group, propylene group, tetramethylene group, pentamethylene group and hexamethylene group. It is done. Of these, a linear alkylene group having 1 to 4 carbon atoms is preferred. B is a linear or branched lower alkylene group or lower alkenylene group. Examples of the lower alkylene group are the same as those described above. Examples of the lower alkenylene group include alkenylene groups having 2 to 6 carbon atoms such as vinylene group, propenylene group, butenylene group, pentenylene group and hexenylene group. Of these, the lower alkylene group is preferably a straight-chain group having 1 to 4 carbon atoms. Moreover, as a lower alkenylene group, a C2-C4 linear thing is preferable. R ¹ Is a hydroxyl group, an amino group or a lower alkoxyl group, and examples of the lower alkoxyl group include the same groups as described above. R ¹ Among these, a hydroxyl group, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, and an amino group are preferable.
[0018]
Examples of the salt of the compound represented by the general formula (1) include alkali metal salts such as sodium salts and potassium salts, alkaline earth metal salts such as calcium salts and magnesium salts, inorganic base salts such as ammonium salts, and triethylamine salts. Pyridine salts, picoline salts, ethanolamine salts, triethanolamine salts, dicyclohexylamine salts, and salts with organic base salts such as organic amine salts such as N, N'-dibenzylethylenediamine salt.
[0019]
Ar, A, B and R ¹ Preferred combinations of are shown below.
Ar is phenyl group, 4-methylphenyl group, 4-methoxyphenyl group, 4-nitrophenyl group, 4-hydroxyphenyl group, 4-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl Group, 2-chlorophenyl group, 3-chlorophenyl group or 3,4-dichlorophenyl group, A is a linear alkylene group having 1 to 4 carbon atoms, and B is a linear alkylene group or carbon having 1 to 4 carbon atoms A linear alkenylene group of 2 to 4 and R ¹ Is preferably a hydroxyl group, amino group, methoxy group, ethoxy group, n-propoxy group or i-propoxy group.
[0020]
More preferably, Ar is a phenyl group, 4-methylphenyl group, 4-methoxyphenyl group, 4-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl group, 2-chlorophenyl group, 3 A chlorophenyl group or a 3,4-dichlorophenyl group, A is a linear alkylene group having 1 to 4 carbon atoms, and B is a linear alkylene group having 1 to 4 carbon atoms or a linear alkenylene having 2 to 4 carbon atoms R and R ¹ Is a hydroxyl group, a methoxy group, an ethoxy group, an n-propoxy group or an i-propoxy group.
[0021]
Particularly preferred is the following case.
Ar, A, B and R ¹ Each of 4-methylphenyl group, ethylene group, ethylene group and hydroxyl group; 4-methoxyphenyl group, ethylene group, ethylene group and hydroxyl group; 4-chlorophenyl group, ethylene group, ethylene group and hydroxyl group; phenyl group, Methylene group, ethylene group and hydroxyl group; phenyl group, trimethylene group, ethylene group and hydroxyl group; phenyl group, ethylene group, methylene group and hydroxyl group; phenyl group, ethylene group, trimethylene group and hydroxyl group; phenyl group, ethylene group Cis-vinylene group and hydroxyl group; phenyl group, ethylene group, trans-vinylene group and ethoxy group; phenyl group, ethylene group, ethylene group and hydroxyl group; phenyl group, ethylene group, ethylene group and methoxy group; phenyl , Trimethylene group, ethylene group and methoxy group; phenyl group, tetramethylene group, ethylene group and methoxy group; phenyl group, ethylene group, trimethylene group and methoxy group; phenyl group, ethylene group, tetramethylene group and methoxy group; phenyl group , Ethylene group, ethylene group and ethoxy group; phenyl group, ethylene group, ethylene group and n-propoxy group; phenyl group, ethylene group, ethylene group and i-propoxy group; 2-chlorophenyl group, ethylene group, ethylene group and methoxy 3-chlorophenyl group, ethylene group, ethylene group and methoxy group; 4-chlorophenyl group, ethylene group, ethylene group and methoxy group; 4-fluorophenyl group, ethylene group, ethylene group and methoxy group; 4-bromophenyl group , Ethylene group, ethylene group and 4-iodophenyl group, ethylene group, ethylene group and methoxy group; phenyl group, trimethylene group, trimethylene group and methoxy group; 3,4-dichlorophenyl group, ethylene group, ethylene group and methoxy group; phenyl group, tetra Methylene group, ethylene group and hydroxyl group; phenyl group, ethylene group, tetramethylene group and hydroxyl group; 2-chlorophenyl group, ethylene group, ethylene group and hydroxyl group; 3-chlorophenyl group, ethylene group, ethylene group and hydroxyl group; 4-fluorophenyl group, ethylene group, ethylene group and hydroxyl group; 4-bromophenyl group, ethylene group, ethylene group and hydroxyl group; 4-iodophenyl group, ethylene group, ethylene group and hydroxyl group, phenyl group, trimethylene group ,bird A methylene group and a hydroxyl group; or 3,4-dichlorophenyl group, ethylene group, ethylene group and hydroxyl group.
[0022]
Specific examples of plant growth regulators include the following. 4-oxo-4 [[2- (4-tolyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-tolyl) ethyl] amino] -butanoic acid, compound 01), 4- Oxo-4-[[2- (4-methoxyphenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-methoxyphenyl) ethyl] amino] -butanoic acid, compound 02), 4- Oxo-4-[[2- (4-chlorophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-chlorophenyl) ethyl] amino] -butanoic acid, compound 03), 4-oxo -4-[[2- (4-Nitrophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-nitrr phenyl) ethyl] amino] -butanoic acid, compound 04), 4-oxo-4-[[2- (4-hydroxyphenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4- hydroxyphenyl) ethyl] amino] -butanoic acid, compound 05), 4-oxo-4- (benzylamino) -butyric acid (4-Oxo-4-benzylamino) -butanoic acid, compound 06), 4-oxo-4- [ (3-Phenylpropyl) amino] -butyric acid (4-Oxo-4-[(3-phenylpropyl) amino] -butanoic acid, compound 07 (formula (2))), 3-oxo-3-[(2-phenyl Ethyl) amino] -propionic acid (3-Oxo-3-[(2 phenethyl) amino] -propanoic acid) compound 08), 5-oxo-5-[(2-phenylethyl) amino] -valeric acid (5-Oxo-5-[(2-phenylethyl) amino] -pentanoic acid, compound 09), (Z) -4-oxo-4-[(2-phenylethyl) amino] -butenoic acid ((Z) -4-oxo-4-[(2-phenylethyl) amino] -2-butenoic acid, Compound 10), (E) -4-oxo-4-[(2-phenylethyl) amino] -butenoate ((E) -ethyl 4-oxo-4-[(2-phenylethyl) amino] -2- butenoate, compound 11), (E) -4-oxo-4-[(2-phenylethyl) Amino] -butenoic acid ((E) -4-oxo-4-[(2-phenylethyl) amino] -2-butenoic acid, Compound 12), 4-oxo-4-[(2-phenylethyl) amino]- Butyric acid (4-Oxo-4-[(2-phenylethyl) amino] -butanoic acid, compound 13), methyl 4-oxo-4-[(2-phenylethyl) amino] -butyrate (Methyl 4-oxo-4-) [(2-phenylethyl) amino] -butanoate, compound 14 (formula (3))), 4-oxo-4-[(2-phenylethyl) amino] -butanamide (4-Oxo-4-[(2-phenylethyl) ) Amino] -butanamide, compound 15), 4-oxo-4-[(3-fur Nylpropyl) amino] -methyl butyrate (Methyl 4-oxo-4-[(3-phenylpropyl) amino] -butanoate, Compound 16), methyl 4-oxo-4-[(4-phenylbutyl) amino] -butyrate (Methyl) 4-oxo-4-[(4-phenylbutyl) amino] -butanoate, compound 17), 5-oxo-5-[(2-phenylethyl) amino] -methyl valerate (Methyl 5-oxo-5-[( 2-phenylethyl) amino] -pentanoate, compound 18), methyl 6-oxo-6-[(2-phenylethyl) amino] monocaproate (Methyl 6-oxo-6-[(2-phenylethyl) amino] -hexanoate Compound 19 4-oxo-4-[(2-phenylethyl) amino] -ethyl butyrate (Ethyl 4-oxo-4-[(2-phenylethyl) amino] -butanoate, compound 20), 4-oxo-4-[( 2-Phenylethyl) amino] -propyl butyrate (Propyl4-oxo-4-[(2-phenylethyl) amino] -butanoate, compound 21), isopropyl 4-oxo-4-[(2-phenylethyl) amino] butyrate ( Isopropyl 4-oxo-4-[(2-phenylethyl) amino] -butanoate, compound 22), 4-oxo-4-[[2- (2-chlorophenyl) ethyl] amino] -methyl butyrate (Methyl 4-oxo- 4-[[2- (2-Chlorophenyl) ) Ethyl] amino] -butanoate, compound 23), 4-oxo-4-[[2- (3-chlorophenyl) ethyl] amino] -methyl butyrate (Methyl 4-oxo-4-[[2- (3-chlorophenyl) ) Ethyl] amino] -butanoate, compound 24), 4-oxo-4-[[2- (4-chlorophenyl) ethyl] amino] -methyl butyrate (Methyl 4-oxo-4-[[2- (4-chlorophenyl) ) Ethyl] amino] -butanoate, compound 25), 4-oxo-4-[[2- (4-fluorophenyl) ethyl] amino] -methyl butyrate (Methyl 4-oxo-4-[[2- (4- fluorphenyl) ethyl] amino] -butanoate 26), 4-oxo-4-[[2- (4-bromophenyl) ethyl] amino] -methyl butyrate ([Methyl 4-oxo-4-[[2- (4-bromophenyl) ethyl] amino] -butanoate) , Compound 27), 4-oxo-4-[[2- (4-iodophenyl) ethyl] amino] -methyl butyrate ([Methyl 4-oxo-4-[[2- (4-iodophenyl) ethyl] amino]-) butanoate, compound 28), 5-oxo-5-[(3-phenylpropyl) amino] -methyl valerate (Methyl 5-oxo-5-[(3-phenylpropyl) amino] -pentanoate, compound 29), 4- Oxo-4-[[2- (3,4-dichlorophenyl) ethyl] amino] butyric acid Til (Methyl 4-oxo-4-[[2- (3,4-dichlorophenyl) ethyl] amino] -butanoate, compound 30), 4-oxo-4-[(4-phenylbutyl) amino] -butyric acid (4 -Oxo-4-[(4-phenylbutyl) amino] -butanoic acid, compound 31), 6-oxo-6-[(2-phenylethyl) amino] -caproic acid (6-Oxo-6-[(2- phenethyl) amino] -hexanoic acid, compound 32), 4-oxo-4-[[2- (2-chlorophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (2-chlorophenyl) ethyl) ] Amino] -butanoic acid, compound 33), 4-o So-4-[[2- (3-chlorophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (3-chlorophenyl) ethyl] amino] -butanoic acid, compound 34), 4-oxo -4-[[2- (4-Fluorophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-fluorophenyl) ethyl] amino] -butanoicacid, compound 35), 4-oxo- 4-[[2- (4-Bromophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-bromophenyl) ethyl] amino] -butanoic acid, compound 36), 4-oxo- 4-[[2- (4-Iodophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- ( -Iodophenyl) ethyl] amino] -butanoic acid, compound 37), 5-oxo-5-[(3-phenylpropyl) amino] -valeric acid (5-Oxo-5-[(3-phenylpropyl) amino] -pentanoic acid, compound 38), 4-oxo-4-[[2- (3,4-dichlorophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (3,4-dichlorophenyl) ethyl] amino). ] -Butanoic acid, compound 39). Of these, compounds 01 to 03, 06 to 11, 13, 14, and 16 to 39 are most preferable.
[0023]
The plant growth regulator used in the present invention can be produced, for example, by the method shown below.
Manufacturing method 1
[0024]
[Formula 4]
[0025]
Manufacturing method 2
[0026]
[Chemical formula 5]
[0027]
Production method 3
[0028]
[Chemical 6]
[0029]
Manufacturing method 4
[0030]
[Chemical 7]
[0031]
(In the formula, Ar, A and B are the same as defined above. R ^1-1 Is a protecting group for a hydroxyl group, an amino group, or a carboxyl group. X represents a hydroxyl group, but a reactive derivative of carboxylic acid such as acid halide, active ester, acid azide and the like may be formed together with CO-. X ′ represents a halogen atom such as chlorine or bromine. R ^1-2 Represents a lower alkyl group. )
[0032]
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, carbonate, acetate, oxalic acid It may be a salt with an organic acid such as a salt, maleate, fumarate, succinate, methanesulfonate, ethanesulfonate or toluenesulfonate.
[0033]
Examples of their anhydrides represented by the compound (b) include 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 ) _Three ] Adipic anhydride [B is (CH ₂ ) _Four ], Pimelic anhydride [B is (CH ₂ ) _Five ]. In addition, compound (c-1) may be a salt with the acid or base described above.
[0034]
In production method 1, compound (a) and compound (b) are mixed with an inert medium, for example, a ketone solvent such as acetone or methyl ethyl ketone, an ether solvent such as diethyl ether, 1,4-dioxane, or tetrahydrofuran, chloroform, or methylene chloride. Reaction in organic chlorinated solvents such as ethylene chloride, aprotic polar solvents such as N, N-dimethylacetamide, dimethyl sulfoxide, N, N-dimethylformamide, and aromatic solvents such as benzene and toluene Compound (c-1) can be synthesized. The molar ratio of the compound (a) to the compound (b) is preferably 0.5 to 1.5: 1.5 to 0.5, for example, and the concentration is not limited as long as it can be reacted. Is, for example, preferably 1 to 30% (W / V), particularly preferably a compound concentration of 5 to 20% (W / V). Under such conditions, for example, the stirring reaction may be performed at 0 to 60 ° C. for 10 minutes to 24 hours. When the compound (a) is a salt, the compound (a) may be desalted with an acid binder described later in advance.
[0035]
Next, production method 2 will be described. As the compound (d), for example, malonic acid [B is CH ₂ ], Succinic acid [B is (CH ₂ ) ₂ ], Maleic acid [B is CH = CH (cis)], fumaric acid [B is CH = CH (trans)], glutaric acid [B is (CH ₂ ) _Three ] Adipic acid [B is (CH ₂ ) _Four ], Pimelic acid [B is (CH ₂ ) _Five ]. When the compound (d) is an active ester, for example, cyanomethyl ester, phenylthioester, p-nitrophenylthioester, methanesulfonic acid ester, benzenesulfonic acid ester, toluenesulfonic acid ester, p-nitrophenyl ester, 2,4- Dinitrophenyl ester, 2,4,5-trichlorophenyl ester, 2,4,6-trichlorophenyl ester, pentachlorophenyl ester, N-hydroxysuccinimide ester, N-hydroxyphthalic acid imide ester, 1H-1-hydroxybenzo Examples include triazole ester, 8-hydroxyquinoline ester, N-hydroxypiperidine ester and the like. Protecting group R ^1-1 Is not particularly limited as long as it forms a carboxyl group by hydrolysis with a dilute alkali or acidic solution. For example, methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, pentyloxy group , A lower alkoxy group such as a hexyloxy group, and an aralkyloxy group such as a benzhydryl group. ¹ May mean. In addition to the above active ester method, a known acid azide method may be used.
[0036]
In the production method 2, when X is a hydroxyl group, for example, 1,3-dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide and the like are used in the reaction between the compound (a) and the compound (d). The compound (c-2) can be synthesized by reacting with a dehydrating condensation agent. In this case, when the compound (a) is a salt, the compound (a) may be desalted with an acid binder described later. 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 later. Examples of the solvent used in this method include 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, Examples include aprotic polar solvents such as N-dimethylformamide, N, N-dimethylacetamide, and dimethyl sulfoxide. Of these, pyridine is most preferred, but when a solvent other than pyridine is used, an acid binder such as triethylamine, tributylamine, dimethylamine, organic bases such as pyridine, calcium carbonate, sodium carbonate, sodium hydroxide, etc. Inorganic bases can be used.
[0037]
R ^1-1 In the case of the above-described protecting group, the compound (d) may be reacted with, for example, an equimolar to 1.5-fold molar amount of a dehydrating condensing agent. After the reaction, R ¹ In the case of a protecting group as described above, for example, it may be hydrolyzed with 1-10 N 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.
[0038]
The reaction solution obtained by the production method 1 or 2 is appropriately cooled to precipitate and recover the target product, and further water or a solubilized organic solvent such as acetone, methanol, ethanol, dimethyl sulfoxide, N, N- The desired product can be obtained by recrystallization from a single or mixed solvent such as dimethylformamide, chloroform, methylene chloride, ethylene chloride, benzene and toluene.
[0039]
In particular, when the target product is recovered from the reaction solution in the production method 2, a product-soluble organic solvent that is not mixed with water and further water are added to the reaction solution for extraction, and then the organic solvent layer is diluted with a dilute acidic aqueous solution such as 1 After washing with a 5N aqueous hydrochloric acid solution, followed by washing with water, further washing with an alkaline aqueous solution such as a saturated aqueous sodium carbonate solution, and finally washing with water in sequence, drying, distilling off the solvent, and if necessary, It can be obtained by recrystallization from one or a mixed solvent, or purification by silica gel column chromatography using a single or mixed solvent.
[0040]
Next, production method 3 will be described. For example, the compound (c-3) is heated and refluxed in a lower alcohol such as methanol, ethanol or propanol in the presence of an acid catalyst such as sulfuric acid or p-toluenesulfonic acid using the compound (c-1) as a raw material. Obtainable. At this time, the initial concentration of the compound (c-1) is not particularly limited, but is preferably 1 to 20% by weight, particularly 5 to 10% by weight. Compound (c-3) may be a salt with the acid or base described above.
[0041]
In order to collect a product from the reaction solution after the reaction, the reaction solvent is distilled off, a product-soluble organic solvent that does not mix with water and water are added, and after recovering the organic solvent layer, an alkaline aqueous solution such as a saturated sodium carbonate aqueous solution is collected. After washing with water, followed by washing with water and drying, after distilling off the organic solvent, it may be recrystallized from a single or mixed solvent as necessary.
[0042]
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 stirred at room temperature for 5 to 30 minutes. After the reaction, thionyl chloride is distilled off to obtain a compound (e). Then, in an inert organic solvent such as acetone, dimethyl sulfoxide, N, N-dimethylformamide, chloroform, methylene chloride, ethylene chloride, benzene, toluene, etc., it is added to aqueous ammonia and cooled with ice. The compound (c-4) can be obtained by reacting with stirring for about 10 to 30 minutes, collecting the precipitated crystals, and recrystallizing the obtained crystals from a single or mixed solvent as necessary. At this time, although there is no restriction | limiting in particular in the initial concentration of a compound (c-1), For example, 1-20% (W / V), Especially 5-10% (W / V) is preferable. The initial concentration of compound (e) in ammonia water is not particularly limited, but is preferably 1 to 25% by weight, particularly 4 to 15% by weight. Compound (c-4) may be a salt with the acid or base described above.
[0043]
The plant growth regulator of this invention can contain 1 type, or 2 or more types of said plant growth regulator or its salt. The plant growth regulator of the present invention may be the above plant growth regulator itself, but may be formulated with a carrier used in usual plant growth regulators such as wettable powders, emulsions, granules and powders.
For example, as a solid carrier, mineral powder (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate, phosphorus lime, etc.), vegetable powder (soy flour, wheat flour, wood flour, tobacco) Powder, starch, crystalline cellulose, etc.), polymer compounds (petroleum resin, polyvinyl chloride, ketone resin, etc.), alumina, waxes, etc. can be used. Examples of the liquid carrier include alcohols (methanol, ethanol, butanol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (toluene, benzene, xylene, etc.), chlorinated hydrocarbons (chloroform, tetrachloride, etc.). Carbon, monochlorobenzene, etc., ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), esters (ethyl acetate, butyl acetate, etc.), acid amides (N, N-dimethylacetamide, etc.) , Ether alcohols (such as ethylene glycol ethyl ether), or water can be used.
As the surfactant used for the purpose of emulsification, dispersion, diffusion, etc., any of nonionic, anionic, cationic and zwitterionic 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 ester, fatty acid salt, alkyl sulfate ester salt, alkyl sulfonate salt, alkyl aryl sulfonate salt, alkyl phosphate ester salt, polyoxyethylene alkyl sulfate ester, quaternary ammonium salt Oxyalkylamine, lecithin, saponin and the like. If necessary, gelatin, casein, sodium alginate, starch, agar, polyvinyl alcohol and the like can be used as an auxiliary agent.
[0044]
There is no restriction | limiting also in the shape of a formulation, It can shape | mold into all formulation forms, such as a powder agent, a granule, a granule, a wettable powder, a flowable agent, an emulsion, and a paste. The plant growth regulator of the present invention can be produced by mixing, stirring, etc., the above-mentioned plant growth regulator and other components according to a conventional method.
[0045]
The plant growth regulator of the present invention has an effect of increasing the amount of roots, an effect of suppressing stem elongation, and the like, and is particularly preferably used as a rooting promoter.
[0046]
When the plant growth regulator of the present invention is used, it may be used directly as it is, or may be used after diluting or suspending to a predetermined concentration with water.
[0047]
When applied to a plant, it can be used as a soil treatment agent, a foliar treatment agent, a seed treatment agent before sowing, a plant treatment agent before transplanting, and the like. In hydroponics, it may be used by mixing with a hydroponic solution, and in tissue culture, it may be suspended or dissolved in a medium.
[0048]
When the plant growth regulator of the present invention is used for spraying, it can be used in a range of 0.01 to 10000 ppm, preferably 1 to 5000 ppm, 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 liter of culture soil. In this case, a spreading agent may be used in combination, and the type and amount of the spreading agent to be used are not particularly limited.
[0049]
The amount used when directly applied to soil, including the case of mixing with fertilizer, is preferably 100 to 10,000 g, particularly 500 to 5000 g per hectare. In particular, when used for seedlings at the seedling raising stage, it is desirable to use 0.001 to 10 g per 1 liter of culture soil. In this case, it may be mixed in advance in the culture soil before sowing, or may be sprayed during the seedling raising period. .
[0050]
When used for seed treatment before sowing, dilute to a liquid carrier such as water, alcohols, and ketones to a concentration of 0.01 to 10000 ppm and spray on the dried seeds or immerse the dried seeds in the diluent. It can also be absorbed by seeds. In this case, the liquid carrier may be evaporated after absorption. Moreover, what was formulated using the solid support | carrier of mineral substance powders, such as clay, can also be used by making it adhere to the seed surface.
[0051]
When used at the time of tissue culture or cell culture, 0.01 to 10000 ppm as a concentration in a medium for plant tissue culture medium (MS medium, white medium, Gamborg's B5 medium, etc.) usually used, preferably 0.1 to It can be used by dissolving or suspending in the range of 1000 ppm. In this case, as usual, saccharides (sucrose, glucose, etc.) as carbon sources, cytokinins (benzyladenine, kinetin, etc.), gibberellins (GA) _Three , GA _Four ), Auxin (indole acetic acid, naphthalene acetic acid, etc.), apsidic acid and the like can be added as appropriate.
[0052]
When directly absorbed into a plant before transplantation, the root or whole of the plant can be immersed in a solution diluted or suspended to a concentration of 0.1 to 1000 ppm. Moreover, if it is a cutting head, it can immerse and use the base or the whole. In this case, the immersion time is preferably 10 seconds to 1 week, particularly 1 hour to 3 days. Moreover, what was formulated using the solid support | carrier of the mineral substance powder may be made to adhere to a root part, and in the case of cuttings, it may be made to adhere to a stem base.
[0053]
As the administration time of the plant growth regulator of the present invention, it can be used at any time during the growth period, but particularly when applied as a rooting promoter, before sowing, at the time of sowing, at the time of seedling growth, transplanting, etc. This is especially effective when the roots are damaged due to weather factors before and after work involving cultivated rooting.
If the plant growth regulator of the present invention is applied to a plant, the amount of roots and root density increase through an increase in the number of roots such as the number of lateral roots, the number of adventitious roots, etc. Effects such as growth promotion, improvement in water absorption, improvement in fertilization capacity, improvement in utilization of fertilizer components, retention of green color, improvement in photosynthetic ability, improvement in water stress resistance, prevention of lodging, and yield improvement can be obtained.
[0054]
The plant to which the plant growth regulator of the present invention is applied is not particularly limited. For example, eggplants such as tomatoes, peppers, peppers, eggplants, cucumbers, pumpkins, melons, cucumbers such as melons, watermelons, cabbages, broccoli , Vegetables such as Chinese cabbage, raw and spicy vegetables such as celery, parsley and lettuce, green onions such as leeks, onions and garlic, beans such as soybeans, peanuts, green beans, peas and azuki beans, and other fruit vegetables such as strawberries, Roots such as radish, turnip, carrot, burdock, potatoes such as taro, cassava, potato, sweet potato, potato, soft vegetables such as asparagus, spinach, honeybee, flower buds such as eustoma, stock, carnation, chrysanthemum Cereals such as rice and corn, turf such as bentgrass and corn, rape, Oil crops such as caustic, sugar crops such as sugar cane and sugar beet, fiber crops such as cotton and rush, feed crops such as clover, sorghum and dent corn, deciduous fruit trees such as apples, pears, grapes and peaches Citrus fruits such as Citrus unshiu, lemon and grapefruit, woody species such as satsuki, azalea and cedar.
[0055]
Further, for the purpose of improving the effect 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 very easy to grow, such as high planting density, high humidity, lack of sunlight, etc., it has a powerful stem growth inhibitory effect for the purpose of growing good-quality seedlings with a low underground weight ratio. It may be used in combination with a gibberellin agent (such as paclobutrazol, uniconazole P, ansimidol), a growth inhibitor (such as daminozide), or an ethylene generator (such as ethephon). For cuttings, cuttings, and tissue culture, auxin compounds that have rooting-promoting effects (such as indoleacetic acid, indolebutyric acid, naphthylacetamide, and naphthaleneacetic acid) are used in combination with the aim of enhancing rooting-promoting effects. May be. Moreover, you may use together with the gibberellin agent which has a germination promotion effect | action at the time of the seed treatment before sowing.
[0056]
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 thereto. The plant growth regulator of the present invention can also be used in combination with various insecticides, fungicides, microbial pesticides, fertilizers and the like. In particular, combined use with hydroxyisoxazole, metasulfocarb, metalaxyl and the like, which have been reported to promote rooting in addition to bactericidal action, is effective in combination with bactericides. In addition, when used in combination with a fertilizer, it is used in combination with a seedling fertilizer for the purpose of raising healthy seedlings, in combination with a fertilizer applied immediately before transplanting for the purpose of promoting survival, and a fertilizer that maintains the efficacy of the plant growth regulator of the present invention for a long period of time. The combined use with a slow-acting fertilizer for the purpose of improving the component utilization rate is particularly effective.
[0057]
【Example】
Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.
[0058]
Production Example 1
(1) 4-oxo-4-[[2- (4-tolyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-tolyl) ethyl] amino] -butanoic acid (Compound 01) ))
35 ml of acetone was added to 3.8 g of succinic anhydride, and 4.9 g of 2- (p-tolyl) ethylamine dissolved in 35 ml of acetone was added with stirring at room temperature. After the addition, the mixture was stirred for 10 minutes and allowed to cool at -15 ° C. The precipitated crystals were collected by filtration under reduced pressure, recrystallized by adding 80 ml of acetone, and the obtained crystals were washed with cold acetone and then dried under reduced pressure to obtain 6.0 g (yield 73%) of Compound 01. Obtained.
[0059]
Production Example 2
4-Oxo-4-[[2- (4-methoxyphenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-methoxyphenyl) ethyl] amino] -butanoic acid (Compound 02)) Synthesis of
In Production Example 1, the same procedure as in Production Example 1 except that succinic anhydride was changed to 5.4 g and 2- (p-methoxyphenyl) ethylamine 7.6 g was used instead of 2- (p-tolyl) ethylamine. 9.7 g (yield 77%) of compound 02 was obtained.
[0060]
Production Example 3
4-oxo-4-[[2- (4-chlorophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-chlorophenyl) ethyl] amino] -butanoic acid (compound 03)) Composition
In the same manner as in Production Example 1, except that 5.4 g of succinic anhydride was used and 7.8 g of 2- (4-chlorophenyl) ethylamine was used instead of 2- (p-tolyl) ethylamine, 6 0.4 g (yield 50%) of compound 03 was obtained.
[0061]
Production Example 4
4-Oxo-4-[[2- (4-nitrophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-nitrophenyl) ethyl] amino] -butanoic acid (Compound 04)) Synthesis of
3.6 g of 2- (4-nitrophenyl) ethylamine hydrochloride was dissolved in 356 ml of anhydrous acetone, and 2.7 g of triethylamine was added with stirring at room temperature. The precipitated triethylamine hydrochloride was filtered, and the filtrate was added to a solution of 2.7 g of succinic anhydride in 18 ml of anhydrous acetone and stirred at room temperature for 45 minutes. Subsequently, the solvent was distilled off under reduced pressure, and 25 ml of acetone was added for recrystallization. The obtained crystals were collected by filtration, washed with cold acetone, and dried under reduced pressure to obtain 1.3 g (yield 17%) of Compound 04.
[0062]
Production Example 5
4-Oxo-4-[[2- (4-hydroxyphenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-hydroxyphenyl) ethyl] amino] -butanoic acid (Compound 05)) Synthesis of
80 ml of acetone was added to 5.1 g of succinic anhydride, and a suspension of 6.9 g of 2- (p-hydroxyphenyl) ethylamine in 20 ml of acetone was added with stirring at room temperature. After the addition, the solution was stirred for 15 minutes, and the solution portion was decanted. Furthermore, the crystal obtained by removing the solvent under reduced pressure was recrystallized with water. The precipitated crystals were washed with cold water and then dried under reduced pressure to obtain 3.9 g (yield 32%) of compound 05.
[0063]
Production Example 6
Synthesis of 4-oxo-4- (benzylamino) -butyric acid (4-Oxo-4- (benzylamino) -butanoic acid (compound 06))
In Production Example 1, 17.1 g (yield 83%) was obtained in the same manner as in Production Example 1 except that 10.7 g of succinic anhydride was used and 10.9 g of benzylamine was used instead of 2- (p-tolyl) ethylamine. %) Of compound 06.
[0064]
Production Example 7
Synthesis of 4-oxo-4-[(3-phenylpropyl) amino] -butyric acid (4-Oxo-4-[(3-phenylpropyl) amino] -butanoic acid (Compound 07))
In Production Example 1, the amount of succinic anhydride was changed to 5.4 g, and 4.0 g (inclusive) was obtained in the same manner as in Production Example 1 except that 6.8 g of 3-phenylpropylamine was used instead of 2- (p-tolyl) ethylamine. 34%) of compound 07 was obtained.
[0065]
Production Example 8
Synthesis of 3-oxo-3-[(2-phenylethyl) amino] -propionic acid (3-Oxo-3-[(2-phenylethyl) amino] -propanoic acid (Compound 08))
50 ml of acetone was added to 4.2 g of malonic acid, and 6.3 g of diphenyldiazomethane was added with stirring under ice cooling, followed by stirring for 10 minutes. Acetone was distilled off under reduced pressure, methylene chloride and water were added for liquid separation, the methylene chloride phase was dehydrated with anhydrous magnesium sulfate, and methylene chloride was distilled off under reduced pressure. The obtained crystals were purified with a silica gel column to obtain 4.9 g of malonic acid monobenzhydryl ester (yield 56%). 3.1 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide was added to a solution of 4.9 g of malonic acid monobenzhydryl ester and 2.2 g of β-phenethylamine under ice-cooling and stirred at room temperature overnight. did. The reaction solution was washed successively with water, 1N HCl, water, saturated aqueous sodium hydrogen carbonate solution and water to obtain a methylene chloride solution of N-phenethylaminomalonic acid monobenzhydryl ester, and 39.5 g of trifluoroacetic acid was added to the solution. And 1.4 ml of water were added and stirred. The reaction mixture was washed with water and extracted with 1N aqueous sodium hydroxide solution and water. Concentrated hydrochloric acid was added to the aqueous phase under ice cooling to make the pH acidic. The mixture was extracted three times with ethyl acetate and washed with water, and then ethyl acetate was distilled off under reduced pressure. The obtained crystals were recrystallized from a mixed solvent of hexane-acetone and dried under reduced pressure to give 1.1 g (yield 28). %) Of compound 08.
[0066]
Production Example 9
Synthesis of 5-oxo-5-[(2-phenylethyl) amino] -valeric acid (5-Oxo-5-[(2-phenylethyl) amino] -pentanoic acid (Compound 09))
In Production Example 1, 6.1 g of glutaric anhydride was used in place of succinic anhydride, and 6.2 g of β-phenethylamine was used in place of 2- (p-tolyl) ethylamine. 3.5 g (yield 30%) of compound 09 was obtained.
[0067]
Production Example 10
(Z) -4-oxo-4-[(2-phenylethyl) amino] -2-butenoic acid ((Z) -4-oxo-4-[(2-phenylethyl) amino] -2-butenoic acid (compound) 10))
In Production Example 1, 2.5 g of maleic anhydride was used in place of succinic anhydride and 3.1 g of β-phenethylamine was used in place of 2- (p-tolyl) ethylamine. 3.6 g (yield 66%) of compound 10 was obtained.
[0068]
Production Example 11
(E) -4-Oxo-4-[(2-phenylethyl) amino] -2-butenoate ((E) -ethyl 4-oxo-4-[(2-phenylethyl) amino] -2-butenoate ( Synthesis of compound 11))
9.5 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride is added to a solution of 7.2 g of monoethyl fumarate and 5.6 g of β-phenethylamine in methylene chloride, and 6.9 ml of triethylamine is added. Stir overnight. The reaction mixture was washed successively with water, 1N HCl, water, saturated aqueous sodium hydrogen carbonate solution and water, dried over anhydrous magnesium sulfate, and methylene chloride was distilled off under reduced pressure. The obtained crystals were recrystallized with a mixed solvent of hexane, ethyl acetate, and acetone and then dried under reduced pressure to obtain 3.3 g (yield 45%) of Compound 11.
[0069]
Production Example 12
(E) -4-oxo-4-[(2-phenylethyl) amino] -2-butenoic acid ((E) -4-oxo-4-[(2-phenylethyl) amino] -2-butenoic acid (compound) 12))
2.0 g of the compound 11 obtained above, 30 ml of 8N sodium hydroxide and 10 ml of water were sequentially added, and the mixture was stirred at room temperature for 95 minutes. Concentrated hydrochloric acid was added to the reaction solution under ice cooling to make the pH acidic. The precipitated crystals were collected by filtration, washed successively with water and acetone, and then dried under reduced pressure to obtain 1.2 g (yield 68%) of Compound 12.
[0070]
Production Example 13
Synthesis of 4-oxo-4-[(2-phenylethyl) amino] -butyric acid (4-Oxo-4-[(2-phenylethyl) amino] -butanoic acid (Compound 13))
In Production Example 1, 15.8 g (yield) was obtained in the same manner as in Production Example 1 except that 10.7 g of succinic anhydride was used and 12.4 g of β-phenethylamine was used instead of 2- (p-tolyl) ethylamine. 72%) of compound 13 was obtained.
[0071]
Production Example 14
Synthesis of methyl 4-oxo-4-[(2-phenylethyl) amino] -butyrate (Compound 14)
4.8 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride is added to 5 g of the methanol solution of compound 13 obtained above, 2.5 g of triethylamine is added, and the mixture is stirred overnight at room temperature. did. The solvent was distilled off under reduced pressure, methylene chloride was added, washed successively with water, 1N HCl, water, saturated aqueous sodium hydrogen carbonate solution and water, dried over anhydrous magnesium sulfate, and methylene chloride was distilled off under reduced pressure. Left. The obtained crystals were recrystallized with a mixed solvent of hexane, ethyl acetate and acetone and then dried under reduced pressure to obtain 2.7 g (yield 51%) of Compound 14.
[0072]
Production Example 15
Synthesis of 4-oxo-4-[(2-phenylethyl) amino] -butanamide (4-Oxo-4-[(2-phenylethyl) amino] -butanamide (Compound 15))
To 5.0 g of the compound 13 obtained above, 50 ml of thionyl chloride was added and stirred at room temperature for 10 minutes. Thionyl chloride was distilled off under reduced pressure, and 15 ml of acetone was added thereto for dissolution, and then added to aqueous ammonia (28%) that had been iced in advance, followed by stirring for 15 minutes under ice cooling. The precipitated crystals were collected by filtration and washed successively with acetonitrile and acetone. The obtained crystals were recrystallized from methanol and dried under reduced pressure to obtain 1.3 g (yield 23%) of Compound 15.
[0073]
Production Example 16
Synthesis of methyl 4-oxo-4-[(3-phenylpropyl) amino] -butyrate (Methyl4-oxo-4-[(3-phenylpropyl) amino] -butanoate (Compound 16))
To 6.8 g of 3-phenylpropylamine, 40 ml of methylene chloride was added, and 5.3 g of triethylamine was added with stirring under ice cooling, followed by further stirring. To this, 8.0 g of methyl succinate dissolved in 40 ml of methylene chloride was added and stirred for about 4 hours. After completion of the reaction, water was added for liquid separation, and the methylene chloride phase was washed successively with 1N HCl, water, saturated aqueous sodium hydrogen carbonate solution and water, dried over anhydrous magnesium sulfate and dried, and then methylene chloride was distilled off under reduced pressure. did. The obtained crystals were purified with a silica gel column and dried under reduced pressure to obtain 8.8 g (yield 72%) of Compound 16.
[0074]
Production Example 17
Synthesis of methyl 4-oxo-4-[(4-phenylbutyl) amino] butyrate (Methyl 4-oxo-4-[(4-phenylbutyl) amino] -butanoate (Compound 17))
In Production Example 16, 10.0 g (yield 77%) of Compound 17 was obtained in the same manner as in Production Example 16 except that 7.5 g of 1-amino-4-phenylbutane was used instead of 3-phenylpropylamine. .
[0075]
Production Example 18
Synthesis of 5-oxo-5-[(2-phenylethyl) amino] -methyl valerate (Methyl5-oxo-5-[(2-phenylethyl) amino] -pentanoate (Compound 18))
In Production Example 16, 7.0 g of β-phenethylamine was used in place of 3-phenylpropylamine, 10.0 g of glutaric acid methyl chloride was used in place of methyl succinate, and 6.1 g of triethylamine was used. 8.9 g (yield 63%) of compound 18 was obtained.
[0076]
Production Example 19
Synthesis of methyl 6-oxo-6-[(2-phenylethyl) amino] caproate (Methyl 6-oxo-6-[(2-phenylethyl) amino] -hexanoate (Compound 19))
80 ml of methylene chloride was added to 10.0 g of monomethyl adipate, 7.0 g of β-phenethylamine was added thereto, and the mixture was stirred for 30 minutes under ice cooling. Next, a hydrochloric acid solution of 11.9 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 10 ml of methylene chloride and 6.3 g of triethylamine were sequentially added and stirred overnight at room temperature. Thereafter, water was added for liquid separation, and after-treatment was conducted in the same manner as in Production Example 16 to obtain 10.9 g (yield 74%) of Compound 19.
[0077]
Production Example 20
Synthesis of Ethyl 4-oxo-4-[(2-phenylethyl) amino] -butanoate (Compound 20)) 4-Oxo-4-[(2-phenylethyl) amino] -ethyl butyrate
In Production Example 16, 7.0 g of β-phenethylamine was used instead of 3-phenylpropylamine and 10.3 g of ethyl chloride succinate was used instead of methyl chloride, and 6.1 g of triethylamine was used. Thus, compound 20 was obtained.
[0078]
Production Example 21
Synthesis of 4-oxo-4-[(2-phenylethyl) amino] -propyl butyrate (Propyl4-oxo-4-[(2-phenylethyl) amino] -butanoate (Compound 21))
100 ml of n-propanol was added to 10.0 g of Compound 13, 0.87 g of paratoluenesulfonic acid was added while stirring at room temperature, and the mixture was stirred at 78 to 80 ° C. for 1 hour, then cooled and dried. Methylene chloride and water were added to the obtained crystals for liquid separation, and the methylene chloride phase was washed successively with a saturated aqueous sodium hydrogen carbonate solution and water, dried over anhydrous magnesium sulfate, and the methylene chloride was distilled off under reduced pressure. This was left at 40 ° C., and the solid-liquid was separated and crystallized to obtain 8.2 g (yield 69%) of Compound 21.
[0079]
Production Example 22
Synthesis of 4-oxo-4-[(2-phenylethyl) amino] -isobutyrate (Isopropyl 4-oxo-4-[(2-phenylethyl) amino] -butanoate (Compound 22))
The same procedure as in Production Example 21 was repeated until the methylene chloride was distilled off in Production Example 21, except that 100 ml of i-propanol was used instead of n-propanol. Next, the obtained crystals were purified with a silica gel column and dried under reduced pressure to obtain 6.1 g (yield 51%) of Compound 22.
[0080]
Production Example 23
4-oxo-4-[[2- (2-chlorophenyl) ethyl] amino] -methyl butyrate (Methyl 4-oxo-4-[[2- (2-chlorophenyl) ethyl] amino] -butanoate (Compound 23)) Synthesis of
In Production Example 16, 6.7 g (yield 50%) of Compound 23 was obtained in the same manner as in Production Example 16, except that 8.0 g of 2- (2-chlorophenyl) ethylamine was used instead of 3-phenylpropylamine. .
[0081]
Production Example 24
4-Oxo-4-[[2- (3-chlorophenyl) ethyl] amino] -methyl butyrate (Methyl 4-oxo-4-[[2- (3-chlorophenyl) ethyl] amino] -butanoate (Compound 24)) Synthesis of
In Production Example 16, 10.9 g (yield 79%) of Compound 24 was obtained in the same manner as in Production Example 16 except that 8.0 g of 2- (3-chlorophenyl) ethylamine was used instead of 3-phenylpropylamine. .
[0082]
Production Example 25
4-Oxo-4-[[2- (4-chlorophenyl) ethyl] amino] -methyl butyrate (Methyl 4-oxo-4-[[2- (4-chlorophenyl) ethyl] amino] -butanoate (Compound 25)) Synthesis of
In Production Example 16, 8.0 g of 2- (4-chlorophenyl) ethylamine was used instead of 3-phenylpropylamine, and the stirring time of about 4 hours was changed to 6.5 hours. 2 g (75% yield) of compound 25 was obtained.
[0083]
Production Example 26
4-Oxo-4-[[2- (4-fluorophenyl) ethyl] amino] -methyl butyrate (Compound 26)) Synthesis of
In Production Example 16, 11.2 g was used in the same manner as in Production Example 16 except that 6.9 g of 2- (4-fluorophenyl) ethylamine was used instead of 3-phenylpropylamine and the stirring time was about 4 hours. Compound (yield 89%) was obtained.
[0084]
Production Example 27
4-Oxo-4-[[2- (4-bromophenyl) ethyl] amino] -methyl butyrate (Compound 27) ) Synthesis
In Production Example 16, 8.0 g of 2- (4-bromophenyl) ethylamine was used instead of 3-phenylpropylamine, 6.4 g of succinic acid methyl chloride and 4.2 g of triethylamine were added, and the stirring time was about 4 hours. 10.9 g (yield 89%) of Compound 27 was obtained in the same manner as in Production Example 16 except that the time was changed to 2 hours.
[0085]
Production Example 28
4-Oxo-4-[[2- (4-iodophenyl) ethyl] amino] -methyl butyrate (Compound 28) ) Synthesis
In Production Example 16, 8.0 g of 2- (4-iodophenyl) ethylamine was used in place of 3-phenylpropylamine, 5.3 g of methyl succinate and 3.5 g of triethylamine, and a further stirring time of about 4 hours. In the same manner as in Production Example 16 except that the time was 2.5 hours, the operation of dehydration and drying with anhydrous magnesium sulfate in Production Example 16 was performed. Then, this was dried under reduced pressure at room temperature overnight to obtain 10.2 g (yield 87%) of compound 28.
[0086]
Production Example 29
Synthesis of 5-oxo-5-[(2-phenylpropyl) amino] -methyl valerate (Methyl 5-oxo-5-[(3-phenylpropyl) amino] -pentanoate (Compound 29))
In Production Example 16, 12.5 g in the same manner as in Production Example 16 except that 8.0 g of 3-phenylpropylamine and 6.2 g of triethylamine were used, and 10.2 g of methyl chloride glutarate was used instead of methyl chloride succinate. Compound (yield 82%) was obtained.
[0087]
Production Example 30
4-oxo-4-[[2- (3,4-dichlorophenyl) ethyl] amino] -methyl butyrate (Methyl 4-oxo-4-[[2- (3,4-dichlorophenyl) ethyl] amino] -butanoate ( Synthesis of compound 30))
In Production Example 16, 6.9 g of succinic acid methyl chloride and 5.3 g of triethylamine were used, and 8.0 g of 2- (3,4-dichlorophenyl) ethylamine was used instead of 3-phenylpropylamine, and stirring was continued for about 4 hours. 10.8 g (yield 84%) of Compound 30 was obtained in the same manner as in Production Example 16 except that the time was changed to 1 hour.
[0088]
Production Example 31
Synthesis of 4-oxo-4-[(4-phenylbutyl) amino] -butyric acid (4-Oxo-4-[(4-phenylbutyl) amino] -butanoic acid (Compound 31))
40 ml of acetone was added to 7.9 g of succinic anhydride, and 11.0 g of 1-amino-4-phenylbutyric acid dissolved in 15 ml of acetone and ice-cooled was added thereto, and the mixture was stirred at room temperature for 5 minutes, and then kept at -15 ° C. And left to cool. The precipitated crystals were collected by filtration under reduced pressure, recrystallized by adding 50 ml of acetone, and the obtained crystals were washed with cold acetone and then dried under reduced pressure to obtain 10.0 g (yield 56%) of Compound 31. Obtained.
[0089]
Production Example 32
Synthesis of 6-oxo-6-[(2-phenylethyl) amino] -caproic acid (6-Oxo-6-[(2-phenylethyl) amino] -hexanoic acid (Compound 32))
1. In the same manner as in Production Example 1 except that 1.3 g of adipic anhydride was used instead of succinic anhydride and 1.2 g of β-phenethylamine was used instead of 2- (p-tolyl) ethylamine in Production Example 1. 6 g (yield 65%) of compound 32 was obtained.
[0090]
Production Example 33
4-oxo-4-[[2- (2-chlorophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (2-chlorophenyl) ethyl] amino] -butanoic acid (compound 33)) Composition
To 7.5 g of succinic anhydride, 50 ml of acetone was added. To this, 11.0 g of 2- (2-chlorophenyl) ethylamine dissolved in 50 ml of acetone and ice-cooled was added, and the mixture was stirred at room temperature for 5 minutes. And left to cool. The precipitated crystals were collected by filtration under reduced pressure, recrystallized by adding 80 ml of acetone, washed with cold acetone and then dried under reduced pressure to obtain 6.4 g (yield 37%) of Compound 33. Obtained.
[0091]
Production Example 34
4-oxo-4-[[2- (3-chlorophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (3-chlorophenyl) ethyl] amino] -butanoic acid (Compound 34)) Composition
In Production Example 33, 7.9 g of succinic anhydride was used, 11.0 g of 2- (3-chlorophenyl) ethylamine was used instead of 2- (2-chlorophenyl) ethylamine, and the precipitated crystals were collected by filtration under reduced pressure. 12.3 g (69% yield) of Compound 34 was obtained in the same manner as in Production Example 33 except that 85 ml of acetone added later was used.
[0092]
Production Example 35
4-Oxo-4-[[2- (4-fluorophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-fluorophenyl) ethyl] amino] -butanoic acid (Compound 35)) Synthesis of
In Production Example 33, 8.4 g of succinic anhydride was used, 11.0 g of 2- (4-fluorophenyl) ethylamine was used instead of 2- (2-chlorophenyl) ethylamine, and the precipitated crystals were collected by filtration under reduced pressure. Then, 2.3 g (yield 12%) of compound 35 was obtained in the same manner as in Production Example 33 except that 20 ml of acetone was added.
[0093]
Production Example 36
4-Oxo-4-[[2- (4-bromophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (4-bromophenyl) ethyl] amino] -butanoic acid (Compound 36)) Synthesis of
50 ml of acetone was added to 2.1 g of succinic anhydride, 4.0 g of 2- (4-bromophenyl) ethylamine dissolved in 50 ml of acetone and ice-cooled was added thereto, and the mixture was stirred at room temperature for 5 minutes, and -15 ° C. And left to cool. The precipitated crystals were collected by filtration under reduced pressure, washed with cold acetone, and then dried under reduced pressure to obtain 3.8 g (yield 65%) of Compound 36.
[0094]
Production Example 37
4-Oxo-4-[[2- (4-iodophenyl) ethyl] amino] -butyric acid (4-0xo-4-[[2- (4-iodophenyl) ethyl] amino] -butanoic acid (Compound 37)) Synthesis of
100 g of acetone was added to 1.7 g of succinic anhydride, 4.0 g of 2- (4-iodophenyl) ethylamine dissolved in 100 ml of acetone and ice-cooled was added thereto, and the mixture was stirred at room temperature for 5 minutes, and -15 ° C. And left to cool. The precipitated crystals were collected by filtration under reduced pressure, washed with cold acetone, and then dried under reduced pressure to obtain 2.9 g (yield 52%) of Compound 37.
[0095]
Production Example 38
Synthesis of 5-oxo-5-[(3-phenylpropyl) amino] -valeric acid (5-Oxo-5-[(3-phenylpropyl) amino] -pentanoic acid (Compound 38))
Add 30 ml of acetone to 10.0 g of glutaric anhydride, add 11.0 g of 3-phenylpropylamine dissolved in 30 ml of acetone and ice-cooled, stir at room temperature for 5 minutes, and cool at -15 ° C. did. The precipitated crystals were collected by filtration under reduced pressure, recrystallized by adding 10 ml of acetone, washed with cold acetone and then dried under reduced pressure to obtain 2.3 g (yield 11%) of Compound 38. Obtained.
[0096]
Production Example 39
4-Oxo-4-[[2- (3,4-dichlorophenyl) ethyl] amino] -butyric acid (4-Oxo-4-[[2- (3,4-dichlorophenyl) ethyl] amino] -butanoic acid (compound) 39))
25 g of acetone was added to 2.3 g of succinic anhydride, and 4.0 g of 2- (3,4-dichlorophenyl) ethylamine dissolved in 20 ml of acetone and ice-cooled was added thereto, and the mixture was stirred at room temperature for 5 minutes. Cooled by standing at 0 ° C. The precipitated crystals were collected by filtration under reduced pressure, washed with cold acetone, and then dried under reduced pressure to obtain 5.0 g (yield 83%) of Compound 39.
[0097]
The physical properties of the compounds 01 to 39 obtained above are shown in Table 1, Table 2, Table 3, Table 4, Table 5, Table 6, and Table 7.
[0098]
[Table 1]
[0099]
[Table 2]
[0100]
[Table 3]
[0101]
[Table 4]
[0102]
[Table 5]
[0103]
[Table 6]
[0104]
[Table 7]
[0105]
Example 1
Rooting-promoting action by azuki bean cut chemical treatment
Azuki seeds (variety name: Erimoshozu, sold by Snow Brand Seed Co., Ltd.) are sown in a normal seedling box (35 cm x 25 cm x 5 cm deep) filled with vermiculite (Kushiro Coal Drying Co., Ltd.) The plants were cultivated under continuous light (2200 lux, 20 ° C.) with a fluorescent lamp for 12 days. The fully developed primary leaf was cut out at a height of 3 cm, and the shoots at the top of the stem were also excised to prepare a test material. Of the 39 types of plant growth regulators prepared in Production Examples 1 to 39, compounds 11, 14, 15 and 16 to 30 were diluted with distilled water as they were, and the others were neutralized with an aqueous sodium hydroxide solution. While diluting with distilled water, an aqueous solution of 7 ppm and 70 ppm was prepared. In each of these aqueous solutions, the cut end of the above Azuki test material was immersed for 72 hours. After the treatment, the base was washed with water, the base was immersed in distilled water for 4 days, and the number of adventitious roots generated was measured. In addition, what was treated with distilled water as a control was cultured, and the number of adventitious roots was similarly measured. As a result, as shown in Table 8, Table 9, and Table 10, a high rooting promoting effect was recognized as compared with the number of roots in the control group. In particular, at a concentration of 70 ppm, the compounds 01 to 03, 06 to 10, 13, 14, 16 to 26, 29, 31 to 36, 38 and 39 have a high rooting promoting activity, and at a concentration of 7 ppm, the compounds 03, 07, 09-11, 13, 14, 16, 17, 20, 32, 35-38 had high rooting promoting activity.
[0106]
[Table 8]
[0107]
[Table 9]
[0108]
[Table 10]
[0109]
Example 2
Comparison of rooting promotion effect with auxin by soaking treatment of azuki bean
Compound 13, Compound 14, and indoleacetic acid, which is an auxin compound, shown in Production Examples 13 and 14 were diluted with distilled water to various concentrations. The compound 13 and indoleacetic acid were diluted while neutralizing with an aqueous sodium hydroxide solution. The test for rooting promoting effect was performed under the same conditions as in Example 1. As a result, as shown in Table 11, the number of roots of compound 13 was significantly higher than that of indoleacetic acid at 20 ppm or more. Compound 14 had a higher rooting number than indoleacetic acid at all concentrations, and the rooting number was particularly high at a concentration of 6 to 60 ppm. Further, it was confirmed that Compound 13 and Compound 14 had no phytotoxicity at a concentration causing phytotoxicity with indoleacetic acid (60 ppm or more), and the applicable concentration was wide. The relative value represents the number of roots in% when the number of roots of the control is 100.
[0110]
[Table 11]
[0111]
Example 3
Effect of tomato cell molding seedling raising seedling
Using a hard plastic cell tray with a hole size of 4.5 cm x 4.5 cm and a hole of 4.5 cm, it is filled with special culture soil (Scotts, Scotts-Sierra Cultural Products) mainly composed of peat. Tomato seeds (variety name: Ochobo, Snow Brand Seedling Co., Ltd.) were cultivated with appropriate fertilization. On day 16 and day 23 after seeding, 500 ml of an aqueous solution of the compound 13, compound 14, indolebutyric acid (IBA), and commercially available ethyl 2-methyl-4-chlorophenoxybutyrate (MCPB) was sprayed per tray. . In preparing the aqueous solution, compound 14 was diluted with deionized water as it was, and compound 13 and indolebutyric acid were diluted with deionized water while neutralizing with an aqueous sodium hydroxide solution. As the 2-methyl 4-chlorophenoxybutyric acid ethyl ester (MCPB) agent, a commercially available Madec emulsion (manufactured by Agrokanesho Co., Ltd., containing 20% MCPB) was diluted as it was. Deionized water was used as a control.
[0112]
On the 29th day after sowing, the root dry weight, the total dry weight, the plant height and the cotyledon-first internode length were measured in 15 individuals × 2 repetitions. The results are shown in Table 12. In addition, the numerical value in the parenthesis in the table indicates the relative value in% when the control group is 100 (the same applies hereinafter). Since the root dry matter weight increased by 7% or more in the treatment groups of all concentrations of Compound 13 and Compound 14, it was confirmed that the rooting promoting effect was high also in actual tomato seedlings.
[0113]
The total dry weight was remarkably increased in the 10 ppm and 100 ppm treated areas of Compound 13 and Compound 14, and a growth promoting effect was also observed. In addition, the plant height shortening effect was also observed in the 1000 ppm treated section of Compound 13 and Compound 14. These effects such as increase in root mass, growth promotion, and length control are desirable at the time of seedling raising, and since no phytotoxicity is observed, the usefulness of Compound 13 and Compound 14 was confirmed. On the other hand, indole butyric acid used as a comparative control had a concentration of 100 ppm or more, 2-methyl-4-chlorophenoxybutyric acid ethyl ester had a phytotoxicity at 10 ppm or more, and 10 ppm indole butyric acid without phytotoxicity caused its root dry matter weight. The effect on was less than all concentrations of Compound 13 and 100 ppm of Compound 14.
[0114]
[Table 12]
[0115]
Example 4
Effects of broccoli on cell-shaped seedling raising seedlings
Broccoli seeds (variety name: green cocoon, Sakata Seed Sales Co., Ltd.) were sown in the same manner as in Example 3 using a hard plastic cell tray with a hole size of 4 cm × 4 cm and 128 holes. On the 14th and 21st days after sowing, 500 ml of an aqueous solution of Compound 13, Compound 14, indolebutyric acid and 2-methyl-4-chlorophenoxyacetic acid ethyl ester prepared in the same manner as in Example 3 was sprayed per tray. On the 29th day after sowing, each item was measured in the same manner as in Example 3 with 16 individuals × 2 repetitions. The results are shown in Table 13. The root dry matter weight increased in the treatment sections of 100 ppm and 1000 ppm of Compound 13 and all concentrations of Compound 14. From this, it was recognized that rooting promoting action was high even in actual broccoli seedlings. The total dry weight increased in the 10 ppm and 100 ppm treated areas of Compound 13 and Compound 14, and a growth promoting effect was also observed.
[0116]
Moreover, the shortening effect of the cotyledon node-first true leaf node length which was easy to grow in the long seedlings was also observed in the 1000 ppm treatment group of Compound 13 and Compound 14. These effects such as increase in root mass, growth promotion, and length control are desirable at the time of seedling raising, and since no phytotoxicity is observed, the usefulness of Compound 13 and Compound 14 was confirmed. On the other hand, indole butyric acid used as a comparative control has a concentration of 100 ppm or more, and 2-methyl-4-chlorophenoxybutyric acid ethyl ester causes phytotoxicity at all concentrations. The effect on dry weight and total dry weight was more suppressive and impractical than the control.
[0117]
[Table 13]
[0118]
Example 5
Effect of lettuce on cell molding seedling raising
Lettuce seeds (variety name: Kalmer MR, sold by Nitto Agricultural Seedling Co., Ltd.) were sown in the same manner as in Example 3 using a hard plastic cell tray with a hole size of 4 cm × 4 cm and 128 holes. On the 10th and 18th day after seeding, 500 ml of an aqueous solution of Compound 13, Compound 14, indolebutyric acid and 2-methyl-4-chlorophenoxyacetic acid ethyl ester prepared in the same manner as in Example 3 was sprayed per tray. On the 25th day after sowing, root dry weight and total dry weight were measured in 16 individuals × 2 repetitions.
[0119]
The results are shown in Table 14. The root dry matter weight was increased by the treatment with Compound 13 and Compound 14, and it was confirmed that the rooting promoting effect was high even in actual lettuce seedlings. The total dry weight increased, and the growth promoting effect was recognized. Since these effects are desirable at the time of raising seedlings and no phytotoxicity is observed, the usefulness of Compound 13 and Compound 14 was confirmed. On the other hand, 2-methyl-4-chlorophenoxybutyric acid ethyl ester caused phytotoxicity, and even indolebutyric acid, which did not cause phytotoxicity, had a lower effect than compounds 13 and 14.
[0120]
[Table 14]
[0121]
Example 6
Effect of bell pepper on cell-shaped seedling raising seedling
Pepper seeds (variety name: Ace, sold by Takii Seed Co., Ltd.) were sown in the same manner as in Example 3 using a hard plastic cell tray with a hole size of 4.5 cm × 4.5 cm and 98 holes. . On the 12th and 21st days after sowing, 500 ml of an aqueous solution of Compound 13 and Compound 14 prepared in the same manner as in Example 3 was sprayed per tray. On the 32nd day after sowing, the root dry weight, leaf area, total dry weight, and aboveground underground weight ratio were measured with 15 individuals × 2 repetitions. The results are shown in Table 15. As for the root dry matter weight, Compound 13 increased by 75% or more in the treatment groups of all concentrations, Compound 14 increased by 10 ppm or 100 ppm, and increased by 60% or more in the 100 ppm treatment group.
[0122]
From this, it was confirmed that the root-promoting action was also high in the actual sweet pepper seedlings. Leaf area and total dry weight increased in all treatment groups of Compound 13 and Compound 14, and a growth promoting effect was also observed. Moreover, it was confirmed that the root development was promoted without increasing the length because the above-ground and underground weight ratio was smaller than that of the control section in all treatment sections. These effects of increasing root mass, promoting growth, and lowering the above-ground underground weight ratio are desirable when raising seedlings, and no phytotoxicity is observed. Therefore, the usefulness of Compound 13 and Compound 14 was confirmed.
[0123]
[Table 15]
[0124]
Example 7
Effect on treatment of transplanted tomato cell seedlings
Tomatoes were bred in the same manner as in Example 3 using a hard plastic cell tray with a hole size of 4.5 cm × 4.5 cm and 98 holes. The seedlings 30 days later were sprayed with 500 ml of an aqueous solution of Compound 13 and Compound 14 prepared in the same manner as in Example 3. The day after spraying, the plant was transplanted to a vinyl pot having a diameter of 12 cm and a depth of 10 cm filled with 550 ml of Sankyo Horticulture (made by Sankai Sankyo). On the 11th day after the transplantation, each item was measured in the same manner as in Example 5 with 4 repetitions. The results are shown in Table 16. In Compound 13 and Compound 14, the root dry matter weight increased by 8% or more in the treatment groups of all concentrations, and it was confirmed that the rooting promoting effect was exhibited after transplantation even by treatment immediately before transplantation. The total dry weight and the number of leaves increased in all treatment groups, and the growth promoting effect after transplantation was also observed.
[0125]
[Table 16]
[0126]
Example 8
Effects of carnation on cuttings
About 5 cm of the tip of the stem was excised from the parent of two varieties of carnations (variety names: California Elf, California Cotillion, sold by Snow Brand Seed Co., Ltd.) and used as cuttings. The cutting head was immersed in an aqueous solution of Compound 13 prepared in the same manner as in Example 3 at a base of about 1 cm. The control group was immersed in deionized water under the same conditions. 24 hours after the start of soaking, the above is applied to a nursery bed filled with culture soil in which pearlite and peat are mixed in a ratio of 7: 3 to a hard plastic cell tray with a hole size of 2.6 cm × 2.6 cm and 162 holes. The cuttings were inserted and cultivated in a glass house.
34 days after cutting, the rooting individual ratio was measured by 5 individuals × 3 repetitions, and the root dry matter weight was also measured. The results are shown in Table 17. At all treatment concentrations, the root dry matter weight increased by over 450% in California Cotillon, more than 32% in California Elves, and the rooting ratio in elf increased by more than 20%. From these facts, it was confirmed that the rooting promotion effect was high also in the carnation cuttings.
[0127]
[Table 17]
[0128]
【The invention's effect】
The plant growth regulator of the present invention has a high rooting promoting activity of plants and has extremely weak side effects such as an action of promoting the growth of leaves on the leaves. Therefore, it is used throughout the growth period as a plant growth regulator, particularly as a rooting promoter. In particular, it is useful as a rooting promoter during seedling raising and transplanting. In addition, it can be added to a medium for the purpose of differentiating roots in plant tissue culture.

Claims (6)

The following general formula (1)
(In the formula, Ar represents a phenyl group optionally substituted by 1 to 5 groups selected from a halogen atom, a hydroxyl group, a nitro group, an alkyl group having 1 to 6 carbon atoms and an alkoxyl group having 1 to 6 carbon atoms. A represents a linear or branched alkylene group having 1 to 6 carbon atoms , B represents a linear or branched alkylene group having 1 to 6 carbon atoms or an alkenylene group having 2 to 6 carbon atoms , R ¹ represents a hydroxyl group, an amino group, or an alkoxyl group having 1 to 6 carbon atoms )
The plant growth regulator which uses the compound or its salt represented by these as an active ingredient. The plant growth regulator according to claim 1, wherein A is a linear alkylene group having 1 to 6 carbon atoms , and B is a linear alkylene group having 1 to 6 carbon atoms or an alkenylene group having 2 to 6 carbon atoms . Ar is phenyl group, 4-methylphenyl group, 4-methoxyphenyl group, 4-nitrophenyl group, 4-hydroxyphenyl group, 4-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl Group, 2-chlorophenyl group, 3-chlorophenyl group or 3,4-dichlorophenyl group, A is a linear alkylene group having 1 to 4 carbon atoms, and B is a linear alkylene group or carbon having 1 to 4 carbon atoms The plant growth regulator according to claim 1, which is a linear alkenylene group of 2 to 4, and R ¹ is a hydroxyl group, amino group, methoxy group, ethoxy group, n-propoxy group or i-propoxy group. Ar is a phenyl group, 4-methylphenyl group, 4-methoxyphenyl group, 4-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl group, 2-chlorophenyl group, 3-chlorophenyl group or 3,4-dichlorophenyl group, A is a linear alkylene group having 1 to 4 carbon atoms, B is a linear alkylene group having 1 to 4 carbon atoms or a linear alkenylene group having 2 to 4 carbon atoms, The plant growth regulator according to claim 1, wherein R ¹ is a hydroxyl group, a methoxy group, an ethoxy group, an n-propoxy group or an i-propoxy group. Ar, A, B and R ¹ are each 4-methylphenyl group, ethylene group, ethylene group and hydroxyl group; 4-methoxyphenyl group, ethylene group, ethylene group and hydroxyl group; 4-chlorophenyl group, ethylene group, ethylene Group and hydroxyl group; phenyl group, methylene group, ethylene group and hydroxyl group; phenyl group, trimethylene group, ethylene group and hydroxyl group; phenyl group, ethylene group, methylene group and hydroxyl group; phenyl group, ethylene group, trimethylene group and Phenyl group, ethylene group, cis-vinylene group and hydroxyl group; Phenyl group, ethylene group, trans-vinylene group and ethoxy group; Phenyl group, ethylene group, ethylene group and hydroxyl group; Phenyl group, ethylene group, ethylene Group and Phenyl group, trimethylene group, ethylene group and methoxy group; phenyl group, tetramethylene group, ethylene group and methoxy group; phenyl group, ethylene group, trimethylene group and methoxy group; phenyl group, ethylene group, tetramethylene group and Methoxy group; phenyl group, ethylene group, ethylene group and ethoxy group; phenyl group, ethylene group, ethylene group and n-propoxy group; phenyl group, ethylene group, ethylene group and i-propoxy group; 2-chlorophenyl group, ethylene group Ethylene group and methoxy group; 3-chlorophenyl group, ethylene group, ethylene group and methoxy group; 4-chlorophenyl group, ethylene group, ethylene group and methoxy group; 4-fluorophenyl group, ethylene group, ethylene group and methoxy group; 4-bromophenyl group, ethylene group 4-iodophenyl group, ethylene group, ethylene group and methoxy group; phenyl group, trimethylene group, trimethylene group and methoxy group; 3,4-dichlorophenyl group, ethylene group, ethylene group and methoxy group; Phenyl group, tetramethylene group, ethylene group and hydroxyl group; phenyl group, ethylene group, tetramethylene group and hydroxyl group; 2-chlorophenyl group, ethylene group, ethylene group and hydroxyl group; 3-chlorophenyl group, ethylene group and ethylene group 4-fluorophenyl group, ethylene group, ethylene group and hydroxyl group; 4-bromophenyl group, ethylene group, ethylene group and hydroxyl group; 4-iodophenyl group, ethylene group, ethylene group and hydroxyl group; phenyl Group, Rimechiren group, a trimethylene group and a hydroxyl group; or 3,4-dichlorophenyl group, an ethylene group, a plant growth regulator according to claim 1 is an ethylene group and hydroxyl group.   The plant growth regulator according to claim 1, which is a plant rooting promoter.