WO1999045774A1 - Plant growth regulating agents - Google Patents

Abstract

Plant growth regulating agents containing as the active ingredient compounds represented by general formula (1) or salt thereof; plant growth regulating compositions containing the above compounds or salts thereof and pesticide carriers or fertilizer carriers; and utilization of the above compounds or salts thereof in the production of plant growth regulating agents. The plant growth regulating agents, etc. have a high activity of promoting rooting and scarcely show any side effects such as leaf epinasty. Thus, they are useful particularly in raising of seedlings and production of seeds and seedlings of agricultural products, fixation of turf plants, etc. and tissue culture. In said formula, Ar represents optionally substituted phenyl; A represents lower alkylene; B represents lower alkylene, etc.; and R1 represents hydroxy, etc.

Description

 Description Plant growth regulator Technical field

 The present invention relates to a plant growth regulator having a high rooting promoting activity of a plant and useful as an agricultural chemical or a fertilizer additive. Background art

 In agriculture, controlling plant growth is an important technology for increasing productivity. Growth control by phyto-nutritional methods is mainly achieved through the appropriate application of chemical fertilizers, and the spread of this technology has dramatically increased crop yields. 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 has contributed to the improvement of yield and quality of products.

 By the way, plant roots absorb various water and nutrients necessary for growth, support the above-ground parts to prevent lodging, and supply plant hormones essential for healthy plant growth to the above-ground parts. It is known to have important functions. [Wai s e 1 et al., Ed., Plan Root s—The Hidden Ha 1 f— (1991)]. Also, especially in transplantation cultivation, it is important to grow seedlings that have a large root mass during the seedling raising stage and quickly root after planting. From these facts, the importance of sufficiently developing the roots of plants in the field of agriculture has been pointed out for a long time [B 00 te et al., Physiology and

 D e t e rm i n a t i o n o f C r o p Y i e l d 6 5— 9 3 (1 994)] o

Conventionally, techniques for promoting root growth generally involve controlling moisture and temperature during fermentation-fertilization management, cultivation soil composition, soil improvement, etc., and sufficient effects are not necessarily obtained. It is not at present. In addition, a method using a plant growth regulator can be considered, but auxin-based compounds such as indolebutyric acid, naphthylacetic acid, and naphthyl acetoamide, which have been put into practical use as rooting promoters, depend on the type and condition of the plant and the concentration to be applied. This may have undesired effects such as epinasal growth of leaves, twisting and cracking of stems, and even death. For this reason, during general seedling raising, the method of use and amount used are limited, and the effect of promoting root development has not been sufficiently satisfactory.

 Also, in plant tissue culture, it is common to add an auxin compound to the medium when it is desired to induce root differentiation, but the root is not induced depending on the type of plant or the culture state. In some cases, the induction rate was remarkably low, which was a problem.In this way, from the viewpoint of raising seedlings and seedlings of agricultural crops, establishing lawn vegetation plants, and using them in tissue culture, There is a need for a plant growth regulator that has a high rooting promoting activity, has substantially no side effects such as an upgrowth effect on leaves, and is completely different from conventional auxin compounds. Disclosure of the invention

 The present inventors have conducted intensive studies to solve such problems, and as a result, surprisingly, the compound represented by the following general formula (1) substantially shows almost no side effects such as leaf upgrowth. And found that the plant has high root-promoting activity, and based on this finding, completed the present invention.

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

_Ar (1)

(In the formula, Ar represents a phenyl group which may have a substituent, A represents a linear or branched lower alkylene group, and B represents a linear or branched lower alkylene group or lower. Represents an alkenylene group, and R ¹ is a hydroxyl group, an amino group or a lower alcohol.

Indicates a group)

And a plant growth regulator comprising a compound represented by the formula or a salt thereof as an active ingredient.

 The present invention also provides a composition for regulating plant growth comprising the compound represented by the general formula (1) or a salt thereof, and a carrier for agricultural chemicals or a carrier for fertilizer. The present invention still further provides use of the compound represented by the general formula (1) or a salt thereof for producing a plant growth regulator. BEST MODE FOR CARRYING OUT THE INVENTION

 The active ingredient (hereinafter referred to as “plant growth regulator”) of the plant growth regulator of the present invention is a compound represented by the above general formula (1) or a salt thereof.

 In the general formula (1), the phenyl group which may have a substituent represented by Ar includes, for example, a halogen atom, a hydroxyl group, a nitro group, a lower alkyl group and a lower alkoxyl group on the benzene ring. And a fuunyl group which may be substituted by 1 to 5 groups selected from The group represented by Ar is represented by the general formula (2).

(In the formula, R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are the same or different and represent a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a lower alkyl group, or a lower alkoxyl group.)

Here, the lower alkyl group is a methyl group, an ethyl group, an n-propyl group, an n- Alkyl groups having 1 to 6 carbon atoms such as butyl, n-pentyl, n-hexyl, i-propyl, i-butyl, i-pentyl and i-hexyl Of these, a methyl group is particularly preferred. The lower alkoxyl group includes methoxy, ethoxy, n-propoxy, n-butoxy, n-pentyloxy, n-hexyloxy, i-propoxy, i-butoxy, and i-pentyloxy. And an alkoxyl group having 1 to 6 carbon atoms such as an i-hexyl group or a methoxy group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

 When these phenyl groups have a substituent, the substitution position may be in the 2 to 6 position or may be shifted, but is preferably in the 2 position, 3 position and Z or 4 position.

 More preferred Ar is a phenyl group which may be substituted with a group selected from a halogen atom, a hydroxyl group, a nitro group, a methyl group and a methoxy group at the 2-, 3- and Z- or 4-positions. .

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. Can be Among them, a linear alkylene group having 1 to 4 carbon atoms is preferable. B is a linear or branched lower alkylene group or a lower alkylene group, and examples of the lower alkylene group are the same as those described above. Examples of the lower alkenylene group include an alkenylene group having 2 to 6 carbon atoms such as a vinylene group, a probenylene group, a butenylene group, a pentenylene group and a hexenylene group. Among them, the lower alkylene group is preferably a linear one having 1 to 4 carbon atoms. The lower alkylene group is preferably a straight chain having 2 to 4 carbon atoms. R ¹ is a hydroxyl group, an amino group or a lower alkoxyl group, and examples of the lower alkoxyl group are the same as those described above. R ¹ is preferably a hydroxyl group, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoquine group, or an amino group. 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, pyridine salt, picoline salt, ethanolamine salt, triethanolamine salt, dicyclohexylamine salt,

N, N′—Salts with organic base salts such as organic amine salts such as dibenzylethylenediamine salt.

 Preferred combinations of Ar, A, B and R 'are shown below.

 Ar is phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-hydroxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl , 4 monophenyl, 2-chlorophenyl, 3-chlorophenyl or 3,4-dichlorophenyl, A is a linear alkylene group having 1 to 4 carbon atoms, and B is 1 to 4 carbon atoms. A linear alkylene group of 4 or a linear alkylene group having 2 to 4 carbon atoms, and may be a hydroxyl group, an amino group, a methoxy group, an ethoxy group, an n-propoxy group or an i-propoxy group. preferable.

More preferably, Ar is a phenyl group, a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-fluorophenyl group, a 4-chlorophenyl group, a 4-bromophenyl group, a 4-iodophenyl group, a 2-chlorophenyl group, or a 3-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 It is a straight-chain alkylene group, and R ¹ is a hydroxyl group, a methoxy group, an ethoxy group, an n-propoxy group or an i-propoxy group.

 Particularly preferred are the following cases.

Ar, A, B and R ¹ force, 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 hydrid Methyl xyl group; phenyl group, methylene group, ethylene group and hydroxy group; phenyl group, trimethylene group, ethylene group and hydroxy group; phenyl group, ethylene group, methylene group and hydroxy group; phenyl group, ethylene Phenyl, ethylene, cis-vinylene and hydroxy groups; phenyl, ethylene, trans-vinylene and ethoxyquin groups; phenyl, ethylene, ethylene and hydroxy groups Groups; phenyl, ethylene, ethylene and methoxy; phenyl, trimethylene, ethylene and methoxy; phenyl, tetramethylene, ethylene and methoxy; phenyl, ethylene Group, trimethylene group and methoxy group; phenyl group, Ethylene group, tetramethylene group and methoxy group; phenyl group, ethylene group, ethylene group and ethoxyquin group; phenyl group, ethylene group, ethylene group and n-propoxy group; phenyl group, ethylene group, ethylene group and i-one group Propoxy group; 2-chlorophenyl group, ethylene group, ethylene group and methoxy group; 3-chlorophenyl group, ethylene group, ethylene group and methoxy group; 4 monochlorophenyl group, ethylene group, ethylene 4 monofluorophenyl group, ethylene group, ethylene group and methoxy group; 4 monobromo group, ethylene group, ethylene group and methoxy group; 4 monophenyl group, ethylene group, ethylene group and methoxy group Toxyl group; phenyl group, trimethylene group, trimethylene group and methoxy group; Lophenyl, ethylene, ethylene and methoxy; phenyl, tetramethylene, ethylene and hydroxy; phenyl, ethylene, tetramethylene and hydroxy xyl; 2-phenylphenyl Group, ethylene group, ethylene group and hydroxy group; 3-chlorophenyl group, ethylene group, ethylene group and hydroxy group; 4-fluorophenyl group, ethylene group, ethylene group and hydroxy group; 4 monobromophenyl group, ethylene group , An ethylene group and a hydroxy group; a 4-phenyl group, an ethylene group, an ethylene group and a hydroxy group, a phenyl group, a trimethylene group, a trimethylene group and a hydroxy group; or a 3,4-dichlorophenyl group, an ethylene group. , Ethylene and hydroxyl groups.

 Specific examples of the plant growth regulator include the following. 4 Oxo— 4 [[2- (4-Tolyl) ethyl] amino] Monobutyric acid

[[2- (4-I tolyl) ethyl] amino] butanoic acid, compound 0 1), 4-year-old xo-1 4-[[2- (4-Methoxyphenyl) ethyl] amino] -butyric acid Ox 0— 4— [L 2-(4 -methoxyphenyl) ethyl] amino] -butanoic acid, compound 0 2), 4-oxo-1-41 [[2- (4-one-phenyl) phenyl] methyl] Monobutyric acid (4-Oxo-4-[[2- (4-chlorophenyl) ethyl] amino] mono-butanoic acid, compound 03), 4-oxo-4-[[2- (4-torophenyl) ethyl ] Amino] —butyric acid (4-Oxo-4-1 [[2- (4-nitrophenyl) ethyl] amino] -amino] -butanoic acid, compound 04), 4-oxo2-[[2-

(4-Hydroxyphenyl) ethyl] amino] Monobutyric acid (4—Oxo— 4— [[2—

(4-Hydroxyphenyl) ethyl J amino] -butanoic acid compound 0 5), 4-oxo_ 4- (benzylamino) monobutyric acid (4—Oxo— 4-benzyloxy) -butanoic acid, compound 06, 4— Oxo—4 — [(3-Phenylpropyl) amino] monobutyric acid (4—Oxo—4 — [(3-phenylphenylpropyl) amino] -butanoic acid, compound

0 7 (Formula (2))), 3-oxo-l 3-[(2-phenylethyl) amino] -p-pionic acid (3-0-XO- 3 — [(2-phenylethyl) amino] -propanoic acid, Compound 0 8), 5-oxo-mono 5-— [(2-phenylethyl) amino] —valeric acid

(5-0x0—5 — [(2-phenylethyl) amino] -pentanoic acid, compound

0 9), (Z) — 4-oxo-1- 4- [(2-phenylethyl) amino] —butenoic acid ((Z) — 4-oxo— 4-L (2-phenylethyl) amino] Compound 10), (E) — 4-oxo — 4-[(2-phenylethyl) amino] Ethyl butenoate ((E) -ethyl 4- oxo — 41-[(2-phenylethyl) amino]-

2— butenoate ヽ Compound 1 1), (E) — 4-oxo-1-41 [(2-phenyldiethyl) Rino] Butenoic acid ((E) — 4--1-oxo— 4-[(2-phenylethyl) amino] ― 2-butenoic acid ヽ Compound 1 2), 4-oxo-4-[(2-phenylethyl) amino] monobutyric acid (4-Oxo-4-1-[(2-phenylethyl) amino] butanoic acid, compound 1 3), 4-oxo-4-[(2-phenylethyl) amino]-methyl butyrate (Methyl 4-oxo- 4-[(2-phenylethyl) amino] one butanoate. Compound 14 (Formula (3)) ), 4 -oxo- 4-[(2-phenylethyl) amino] -butanamide (4-Oxo-4-[(2 -phenylethyl) amino] -butanamide. Compound 15), 4 -oxo2 4-[(3 —Phenylpropyl) amino] methyl 4-butyrate (Methyl 4-oxo—4-[(3-phenylpropyl) amino] —butanoate, compound 16), 4-oxo—4 -— ((4-phenylbutyl) amino [No]-methyl butyrate (Methyl 4-oxo-l 4- [(4-phenylbutyl) amino] i-butanoate, compound 17), 5-oxo-5- [(2-phenylinethyl) amino] Ichikichi Methyl 5 -oxo- 5-[(2-phenylethyl) amino] -pentanoate, compound 18), 6-oxo-1 6-[(2-phenylethyl) amino] 6-oxo — 6— [(2-phenylethyl) amino] -hexanoate, compound 19), 4-oxo—4-[(2-phenylethyl) amino] ethyl ethyl butyrate (Ethyl 4 -oxo- 4-[( 2-phenylethyl) amino] butanoate, compound 20), 4-oxo- 4- [(2-phenylethyl) amino] propyl monobutyrate (Propyl 4- oxo-4-[(2-phenylethyl) amino] one butanoate. 2 1), 4-Okifu 4-[(2-phenylethyl) amino] Isopropyl butyrate (Isopropyl 4-oxo-4-[(2-phenylethyl) mino]-butanoate, compound 22), 4-Oki2 4-1 [ [2- (2-Chlorophenyl) ethyl] amino] —Methyl 4-oxo-4 — [[2- (2-chlorophenyl) ethyl] amino] -butanoate, compound 23), 4-oxo- 1-4-[[2- (3-chlorophenyl) ethyl] amino] Methyl mono-butyrate (Methyl 4-oxo- 4--[L2-C3-chlorophenyl) ethyl] amino "—butanoate , Compound 24), 4-oxo-1- 4-[[2- (4-chlorophenyl) ethyl] amino] Methyl 4-butyrate (Methyl 4-oxo—4-[[2— (4-chlorophenyl) ethyl] amino] -butanoate, compound 25), 4-oxo2 4-[[2- (4- (4-diphenyl) ethyl) ethyl ] Amino] —Methyl 4-butyrate [[2-

(4-fluorophenyl) ethyl] amino] -butanoate, compound 26), 4-oxo-4-[[2- (4-bromophenyl) ethyl] amino] —methyl butyrate

(Methyl 4-oxo—4 -— [[2- (4-bromophenyl) ethyl] amino ”one-butanoate, compound 27), 4-oxo—4-[[2- (4-one-phenyl) ethyl] amino] one Methyl butyrate (Methyl 4—oxo— 4— [[2— (4— iodophenyl) ethyl] amino] monobutanoate ヽ compound 28 8), 5-oxo-1 5—

[(3-Phenylpropyl) amino] —Methyl 5-oxo -5-

[(3-phenyl propyl) amino]-pentanoate, compound 2 9), 4-oxo2-4-[[2-(3, 4-dichloro-phenyl) ethyl] amino] methyl butyrate (Methyl

4-oxo-4-[[2-, 3, 4-dichloropheny 1) ethyl] mino "-butanoate, compound 30), 4-oxo 4-[(4-phenyl butyl) amino] monobutyric acid (4 Oxo—41-[(4-phenylbutyl) amino] -butanoic acid compound 3 1), 6-oxo—6 — [(2-phenylethyl) amino] —caproic acid (6—Oxo-6-[(2- phenylethyl) amino] -hexanoic acid. Compound 3 2), 4-oxo- 1 4 -— [[2- (2-chlorophenyl) ethyl] amino] monobutyric acid (4-Oxo-4-[[2- (2- chlorophenyl) ethyl] amino] -butanoic acid, compound 3 3), 4-oxo—4-[[2- (3-chlorophenyl) ethyl] amino] —butyric acid (4-0x0—4 — [[2 — (3-chlorophenyl) ethyl] amino] butanoic acid, compound 3 4), 4 oxo— 4— [[2- (4-fluorophenyl) ethyl] amino] —butyric acid (4—Oxo— 4 2-(4 -f luorophenyl;) ethyl] amino] -butanoic acid, Compound 3 5), 4-Okiso one 4 one [[2

(4—Promopanic) ethyl] Amino] monobutyric acid (4 Oxo— 4— [[2— (4-bromophenyl) ethyl] amino] amino] -butanoic acid, ί 合物 3 6), 4 1 year old Kiso 4-1-[[2- (4-iodophenyl) ethyl] amino] —butyric acid (4--0.XO-4-1 [[2- (4-iodophenyl) ethyl] amino] -butanoic acid ), 5-oxo2 5-((3-Phenylpropyl) amino) monovaleric acid (5-Oxo-5-[(3-phenylpropyl) amino] -pentanoic acid ヽ compound 38 8), 4-oxo4 1-[[2- (3,4-Dichloromouth phenyl) ethyl] amino] monobutyric acid (4-Oxo—4 — [[2- (3,4-dichlorophenyl) ethyl] amino] -butanoic acid, compound 3 9). Of these, compounds 01 to 03, 06 to 11, 13, 13, 14, 16 to 39 are most preferred.

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

Manufacturing method 1

0

Ar ^{x X} NH ₂

 (Compound (a))

 0

(Compound (b))

 Η

(Compound (c-1)) Manufacturing method 2

 (Compound (a))

 (Compound (d))

 H

 (Compound (c-1 2))

Manufacturing method 3

Ar /

(Compound (c-1)) (Compound (c-1))

Manufacturing method 4

(Compound (C-1))

 (Compound (e))

ΝΗ.

 (Compound (c-4))

(Wherein Ar, A and B are the same as above. R ¹ — ¹ is a protecting group for a hydroxyl group, an amino group or a carboxyl group. X represents a hydroxyl group, and together with CO—, an acid halide, . an active ester, can be coupled to form a reactive derivative of the force Rupon acids such SanRyo disilazide X 'is chlorine, R ¹ represents a halogen atom such as bromine - shows the ² lower alk kill group)..

 Next, Production Method 1 will be described. Compound (a) is a salt with an inorganic acid such as hydrochloride, hydrobromide, hydrobromide, sulfate, perchlorate, phosphate, nitrate or carbonate, acetate, It may be a salt with an organic acid such as oxalate, maleate, fumarate, succinate, methanesulfonate, ethanesulfonate, and toluenesulfonate.

Examples of those anhydrides represented by the compound (b) include, for example, malonic anhydride [B CH ₂ ), succinic anhydride [B is (CH ₂ ) 2], maleic anhydride [B is CH = CH (cis)], glutaric anhydride [B (CH ₂ ) ₃ ], adipic anhydride [B is (CH ₂ ) ₄ ] and pimelic anhydride [B is (CH ₂ ) ₅ ]. Further, the compound (c-11) may be a salt with the above-mentioned acid or base.

 In production method 1, compound (a) and compound (b) are converted into an inert medium, for example, a ketone solvent such as acetone or methyl ethyl ketone, or an ether such as getyl ether, 1,4-dioxane, or tetrahydrofuran. Organic solvents, organic solvents such as chloroform, methylene chloride, ethylene chloride, etc .; non-protonic polar solvents such as N, N-dimethylacetamide, dimethylsulfoxide, N, N-dimethylformamide The compound (c-11) can be synthesized by reacting in an aromatic solvent such as benzene, toluene or the like. The molar ratio of the compound (a) to the compound (b) is preferably, for example, 0.5 to 5: 1.5 to 0.5, and the concentration is not particularly limited as long as it is a concentration that can react. However, for example, the concentration is preferably 1 to 30% (W / V), particularly preferably the compound concentration is 5 to 20% (W / V). Under such conditions, for example, the reaction may be stirred at 0 to 60 ° C. for 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. Examples of the compound (d) include 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 ) ₃ ], adipic acid [B is (CH ₂ ) ₄ ], and pimelic acid [B is (CH ₂ ) ₅ ]. When compound (d) is an active ester, for example, cyano methyl ester, phenyl thioester, p-ditrophenyl thioester, methanes phonate, benzenesulfonate, toluenesulfonate, p-diester Trophenyl ester, 2,4-dinitrophenyl ester, 2,4,5-trichlorophenyl ester, 2,4,6-trichlorophenyl ester, pen phenyl ester, N-hydroxysuccinate Acid imidoester, Examples include N-hydroxyphthalic acid imido ester, 1H-1-hydroxybenzotriazole 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 with solution hydrolysis min in dilute Al force Li or acidic solution, for example, main butoxy group, an ethoxy group, a propoxy group, isopropoxy And a lower alkoxy group such as a butoxy group, an Ibutoxy group, a pentyloxy group, and a hexyloxy group, and an aralkyloxy group such as a benzhydryl group. These protecting groups may be R. In addition to the active ester method described above, a known acid azide method may be used.

 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, 1-ethyl-3- (3-dimethyla) The compound (c-12) can be synthesized by reacting with a dehydrating condensing agent such as minopropyl) amide. At this time, when the compound (a) is a salt, the compound (a) may be desalted in advance with an acid binder described below. When X is a halogen atom, the compound (c-12) can be synthesized by reacting the compound (d) with the compound (a) in the presence of an acid binder described below. Solvents used in this method include, for example, organic chlorinated solvents such as methylene chloride and chloroform, ether solvents such as dimethyl ether and tetrahydrofuran, aromatic solvents such as benzene and toluene, and heterocyclic rings such as pyridine. And aprotic polar solvents such as N, N-dimethylformamide, NN-diethylacetamide, and dimethylsulfoxide. Of these, pyridine is the most preferred. When a solvent other than pyridine is used, organic bases such as triethylamine, triptylamine, dimethylamine, and pyridine are used as acid binders, calcium carbonate, sodium carbonate, and sodium hydroxide. An inorganic base such as lime can be used.

In the case where R ¹ is the above-mentioned protecting group, the compound (d) may be, for example, The reaction may be carried out using 1.5 times the molar amount of a dehydrating condensing agent. After completion of the reaction, if R is the above-mentioned protecting group, hydrolysis treatment is preferably performed at room temperature or under heating for 30 minutes to 8 hours under alkaline conditions using, for example, 1 to 10 N NaOH or KOH. Then, it may be neutralized with concentrated hydrochloric acid.

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

 In particular, when the target substance is recovered from the reaction solution in the production method 2, the reaction solution is extracted by adding a product-soluble organic solvent which is not mixed with water and further water, and then the organic solvent layer is extracted with a dilute acidic aqueous solution such as 1 After washing with a 5N aqueous hydrochloric acid solution and then with water, further washing with an alkaline aqueous solution, for example, a saturated aqueous solution of sodium carbonate, finally washing with water sequentially, drying and evaporating the solvent, if necessary, It can be obtained by recrystallization from a single or mixed solvent or purification by silica gel gel chromatography using a single or mixed solvent.

 Next, Production Method 3 will be described. For example, by heating compound (c-11) as a raw material in a lower alcohol such as methanol, ethanol or propanol under reflux in the presence of an acid catalyst such as sulfuric acid or p-toluenesulfonic acid, the compound (c— 3) can be obtained. At this time, the initial concentration of the compound (c-11) is not particularly limited, but is preferably, for example, 1 to 20% by weight, particularly preferably 5 to 10% by weight. The compound (c-13) 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 collected, and then an aqueous alkaline solution, for example, saturated After washing with an aqueous solution of sodium carbonate, followed by washing with water and drying, the organic solvent is distilled off, and then, if necessary, recrystallization from a single solvent or a mixed solvent.

1 δ Next, Production Method 4 will be described. For example, the compound (c-11) is used as a raw material and, for example, an equimolar amount or more of thionyl chloride is used for a reaction at room temperature for 5 to 30 minutes with stirring. After the reaction, the 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. The mixture was reacted under stirring for about 10 to 30 minutes under ice-cooling, then the precipitated crystals were collected, and the obtained crystals were recrystallized from a single solvent or a mixed solvent, if necessary. ) Can be obtained. At this time, the initial concentration of the compound (c-11) is not particularly limited, but is preferably, 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. The compound (c-14) may be a salt with the above-mentioned acid or base.

 The plant growth regulator and the composition for regulating plant growth of the present invention may contain one or more of the above-mentioned plant growth regulators or salts thereof. The plant growth regulator and the composition for regulating plant growth of the present invention may be the above-described plant growth regulator itself, or a carrier acceptable as a carrier for agricultural chemicals or fertilizers such as wettable powders, emulsions, granules, and powders. May be blended.

For example, solid carriers include mineral powders (such as kaolin, bentonite, clay, montmorillonite, talc, clay, mica, vermiculite, Secco, calcium carbonate, phosphorous lime, etc.) and vegetable powders (soybean Flour, wheat flour, wood flour, tobacco flour, starch, crystalline cellulose, etc., high molecular compounds (petroleum resin, polychlorinated vinyl, ketone resin, etc.), and alumina, waxes, etc. can be used. Examples of the liquid carrier include alcohols (such as methanol, ethanol, butanol, ethylene glycol, and benzyl alcohol), aromatic hydrocarbons (such as benzene, benzene, and xylene), and chlorine. Hydrocarbons (chloroform, carbon tetrachloride, monochlorobenzene, etc.), ethers (dioxane, tetrahydrofuran) ), Ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), esters (ethyl acetate, butyl acetate, etc.), acid amides (N, N-dimethylacetamide, etc.), ether alcohols ( For example, ethylene glycol monoethyl ether) or water can be used.

 As the surfactant used for the purpose of emulsification, dispersion, diffusion and the like, 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 rubitane fatty acid ester, Oxyethylene polymer, oxypropylene polymer, polyoxyethylene alkyl phosphate, fatty acid salt, alkyl sulfate ester, alkyl sulfonate, alkyl aryl sulfonate, alkyl phosphate ester salt, polyoxy Ethylene alkyl sulfate, quaternary ammonium salt, oxyalkylamine, lecithin, saponin and the like. If necessary, gelatin, casein, tuda alginate, starch, agar, polyvinyl alcohol and the like can be used as adjuvants.

 There is no limitation on the form of the preparation, and it can be formed into any preparation form such as powders, granules, granules, wettable powders, flowables, emulsions and pastes. The plant growth regulator and the composition for regulating plant growth 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 and the composition for controlling plant growth of the present invention have an effect of increasing root mass, an effect of suppressing stem elongation, and the like, and are particularly preferably used as a rooting promoter.

When using the plant growth regulator or the composition for regulating plant growth of the present invention, the plant of the present invention may be used directly as it is, or may be used after being diluted or suspended to a predetermined concentration with water. Growth regulators and compositions for regulating plant growth include plants, seeds, tissue cultures, etc. It is particularly useful as a pesticide and fertilizer.

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

 When the plant growth regulator or the composition for regulating plant growth of the present invention is used for spraying, the concentration used is 0.01 to 100 ppm, preferably 1 to 500 ppm, particularly preferably. Can be used in the range of 5 to 100 ppm. In particular, when used for seedlings in the seedling raising stage, it is desirable to spray 50 to 20 OmL of the diluted solution of the above concentration per 11 culture soil. In this case, a spreading agent may be used in combination, and the type and amount of the spreading agent used are not particularly limited.

 When applied directly to the soil, including when mixed with fertilizers, it is preferable to use 100 to 100 g, preferably 500 to 500 g per hectare. . In particular, when used for seedlings in the seedling raising period, it is preferable to use 0.001 to 10 g per 11 of the culture soil.In this case, it may be mixed in advance with the culture soil before sowing, May be sprayed.

 When used for seed treatment before sowing, dilute it in a liquid carrier such as water, alcohols, and ketones to a concentration of 0.01 to 100 ppm, and spray or dry the dried seeds. It can be immersed in a diluent and absorbed by seeds. In this case, the liquid carrier may be evaporated after the absorption. In addition, a formulation prepared using a solid carrier of mineral powder such as clay can be used by adhering it to the seed surface.

When used for tissue culture or cell culture, the concentration in the culture medium is usually 0.01 to 100,000 in the commonly used plant tissue culture medium (MS medium, White medium, Gamborg B5 medium, etc.). It can be used by dissolving or suspending in the range of ppm, preferably in the range of 0.1 to 1000 ppm. In this case, as usual, saccharides (sucrose, glucose, etc.) as carbon sources and cytokins as various plant hormones are used. 'Adenine, etc. force Inechin) and gibberellins (GA _3, GA _4), O Kishin (indoleacetic acid, naphthoquinone evening etc. Ren acetate), it may be obtained as appropriate pressurizing the Apushijin acid.

 When directly absorbed into 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 100 ppm. If the cuttings are used, the base or the whole can be used after being crushed. In this case, the crushing time is preferably 10 seconds to 1 week, particularly 1 hour to 3 days. In addition, a formulation prepared using a solid carrier of a mineral powder may be attached to the root or, in the case of spikelets, to the stem base.

 The administration time of the plant growth regulator or the composition for regulating plant growth of the present invention can be used at any time during the growing period, but particularly before and after sowing when applied as a rooting promoter. It is especially effective when raising seedlings, before and after work involving cultivated rooting such as transplanting, or when root damage occurs due to weather factors.

 When the plant growth regulator or the composition for regulating plant growth of the present invention is applied to a plant, the root mass and root density increase through an increase in the number of lateral roots, the number of adventitious roots, etc. Improving and raising healthy seedlings, promoting growth, improving water absorption, improving fertilizer absorption, improving fertilizer component utilization, maintaining green color, improving photosynthetic capacity, improving water stress tolerance, preventing lodging, improving yield, etc. The effect is obtained.

The plant to which the plant growth regulator and the composition for controlling plant growth of the present invention are applied is not particularly limited. For example, eggplants such as tomato, pepper, tomato, eggplant, cucumber, pumpkin, melon, and watermelon And other vegetables, such as cabbage, broccoli, Chinese cabbage, celery, and so on. Fresh vegetables such as spices, lettuce, spices, leeks, evening onions, garlic, etc., soybeans, peanuts, green beans, endu, azuki, etc., other fruits and vegetables such as strawberries, radish, turnips, carrots, Direct roots such as burdock, potatoes such as taro, cassava, raisho, sweet potato, nagaimo, etc., asparagus, spinach, soft vegetables such as koku, eustoma, strike Flowers, such as rice, corn, etc., grasses, such as bentgrass and red rice, oil crops, such as rapeseed and peanut, sugar crops, such as sugar cane, sugar beet, and ivy , Ficus crops such as ixa, forage crops such as clover, sorghum, and dent corn, linco ", deciduous fruit trees such as pear, grape, peach, etc. And woody species such as cedar.

 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 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 good-quality seedlings with a low aboveground and underground weight ratio. It may be used in combination with anti- gibberellins (eg, butorazole, nicotinazole P, ancimidol, etc.), growth inhibitors (eg, daminozide), and ethylene generators (eg, ethephon). In cuttings, cuttings, and tissue culture, auxin-based compounds (indoleacetic acid, indolebutyric acid, naphthylacetoamide, naphthamide, etc.) that originally have a rooting-promoting effect are used to enhance the rooting-promoting effect. Acetic acid). Further, at the time of seed treatment before sowing, a gibberellin agent having a germination promoting effect may be used in combination.

These are merely examples, and other plant growth regulators that can be used in combination with the plant growth regulator or the plant growth regulating composition of the present invention are not limited thereto. Further, the plant growth regulator and the composition for regulating plant growth of the present invention can be used in combination with various insecticides, fungicides, microbial pesticides, fertilizers and the like. In particular, combination use with a fungicide, such as hydroxyisoxazole, metas focalp, or metalaxyl, which has been reported to promote rooting in addition to the bactericidal effect, is effective. When used in combination with fertilizer, it is used in combination with fertilizer for raising seedlings for the purpose of growing healthy seedlings, combined with fertilizer applied immediately before transplantation for the purpose of promoting survival, and maintaining the efficacy of the plant growth regulator of the present invention for a long time. Combination with slow-release fertilizer for the purpose of improving the utilization rate of fertilizer components is particularly effective. Example

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

Production Example 1

 (1) 4-oxii 4-[[2-(4-tri geometry;) ethyl] amino]-butyric acid (4-0x0-4 [[2-(4-tolyl) ethyl] amino]-butanoic acid (compound 0 1)) Synthesis of succinic anhydride (3.8 g), acetone (35 mL) was added, and while stirring at room temperature, 2- (p-tolyl) ethylamine (4.9 g) dissolved in acetone (35 mL) was added. After adding c, the mixture was stirred for 10 minutes and allowed to cool at 115 ° C. The precipitated crystals were collected by filtration under reduced pressure, recrystallized by adding 8 OmL of acetone, washed with cold acetone, and dried under reduced pressure to obtain 6.0 g (yield 73%). Compound 01 was obtained.

Production Example 2

 4- 4-[[2- (4-Methoxyphenyl) ethyl] amino] monobutyric acid (4-0x0-4-[[2- (4-niethoxyphenyl) ethyl] amino] -butanoic acid (Compound 02)) Synthesis

 Preparation Example 1 is the same as Preparation Example 1 except that 5.4 g of succinic anhydride was used and 7.6 g of 2- (p-methoxyphenyl) ethylamine was used instead of 2- (p-tolyl) ethylamine. In the same manner as in the above, 9.7 g (yield 77%) of compound 02 was obtained.

Production Example 3

 4-oxo2 4-[[2- (4-chlorophenyl) ethyl] Rinomino] butyric acid

Synthesis of (4-0x0-4-[[2- (4-chlorophenyl) ethyl] amino] -butanoic acid (Compound 03))

Production Example 1 was repeated except that succinic anhydride was changed to 5.4 g and 2- (4-tolyl) ethylamine was replaced by 7.8 g of 2- (4-chlorophenyl) ethylamine. In the same manner as in Example 1, 6.4 g (yield 50%) of compound 03 was obtained. Production Example 4

 Synthesis of 4-oxo-4-[[2- (4-nitrophenyl) ethyl] amino] monobutyric acid (4-0xo-4-[[2- (4-nitrophenylethyl] amino] -butanoic acid (Compound 04))

 3.6 g of 2- (4-nitrophenyl) ethylamine hydrochloride was suspended in aceton 356 m, and 2.7 g of triethylamine was added while 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 m of acetone, and the mixture was stirred at room temperature for 45 minutes. Next, 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.

Production Example 5

 4-1-oxo-1 4-[[2- (4-Hydroxyphenyl) ethyl] amino] Ichibutori (4-0x0-4-[[2- (4-hydroxyphenyl) ethyl] amino] -butanoic acid ( Synthesis of compound 05))

 To 5.1 g of succinic anhydride, 8 OmL of acetone was added, and while stirring at room temperature, a suspension of 6.9 g of 2- (p-hydroxyphenyl) ethylamine in Acetone 2 OniL was added. After the addition, the mixture was stirred for 15 minutes, and the solution was decanted. Further, the crystals obtained by removing the solvent under reduced pressure were recrystallized with water. The precipitated crystals were washed with cold water and dried under reduced pressure to obtain 3.9 g (yield 32%) of Compound 05. Production Example 6

 Synthesis of 4 Oxo-4-(be.nzylaminoV butanoic acid (Compound 06))

 In Preparation Example 1, 10.7 g of succinic anhydride was used, and 10.9 g of benzylamine was used in place of 2- (p-tolyl) ethylamine. 1 g (83% yield) of compound 06 was obtained.

Production Example 7

9 9 Synthesis of 4-oxo-1-[(3-phenylpropyl) amino] monobutyric acid (4-Oxo-4-[(3-phenylpropyl) amino] -butanoic acid (Compound 07))

 Production Example H Same as Production Example 1 except that 5.4 g of succinic anhydride was used, and 6.8 g of 3-phenylpropylamine was used instead of 2- (p-tolyl) ethylamine. Thus, 4.0 g (yield 34%) of a compound 07 was obtained.

Production Example 8

 Synthesis of 3-Oxo-3-([2-phenylethyl) amino] monopropionic acid (3-Oxo-3-[(2-phenylethyl) amino] -propanoic acid (Compound 08))

 50 mL of acetone was added to 4.2 g of malonic acid, 6.3 g of diphenyldiazomethane was added with stirring under ice cooling, and the mixture was stirred for 10 minutes. Acetone was distilled off under reduced pressure, methylene chloride and water were added, and the mixture was separated. The methylene chloride phase was dehydrated with anhydrous magnesium sulfate, and methylene chloride was distilled off under reduced pressure. The obtained crystals were purified by a silica gel column to obtain 4.9 g (yield 56%) of monobenzhydryl malonate. 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide 3.1 g under ice-cooling 4.9 g of monobenzhydryl malonate and 2.2 g of / 3-phenyleneamine in methylene chloride And stirred at room temperature overnight. The reaction solution was washed sequentially with water, 1N HC: ^, water, a saturated aqueous solution of sodium bicarbonate, and water to obtain a methylene chloride solution of N-funethylaminomalonic acid monobenzhydryl ester, and the solution was added to trifluorofluoride. 39.5 g of acetic acid and 1.4 mL of water were added and stirred. After the reaction solution was washed with water, it was extracted with a 1N aqueous solution of sodium hydroxide and water. Concentrated hydrochloric acid was added to the aqueous phase under ice-cooling to make the pH acidic. After extraction with ethyl acetate three times and washing with water, ethyl acetate was distilled off under reduced pressure, and the obtained crystals were recrystallized from a mixed solvent of hexane-aceton and dried under reduced pressure to obtain 1.1 g (yield 2 8%) of compound 08 was obtained.

Production Example 9

5—oxo— 5— [(2-phenylene) Rinomino] —valeric acid (5-Oxo 5-[(2- Synthesis of phenylethyl) amino] -pentanoic acid (1 compound 09)) In Production Example 1, 6. ig of glutaric anhydride was used instead of succinic anhydride, and 2- (p-tolyl) ethylamine was used instead of 2- (p-tolyl) ethylamine Except that 6.2 g of / 8-phenethylamine was used, 3.5 g (30% yield) of compound 09 was obtained in the same manner as in Production Example 1. Production Example 10

 (Z) — 4-oxo 4-([2-phenylethylamine) amino] — 2-butenoic acid ((Z) -4-oxo-4-[(2-phenylethyl) amino] -2-butenoic acid (compound 1 0).)

 Production Example 1 is the same as Production Example 1 except that 2.5 g of maleic anhydride was used instead of succinic anhydride and 3.1 g of phenethylamine was used instead of 2- (p-tolyl) ethylamine. Preparation Example 11 yielded 3.6 g (yield 66%) of compound 10

 (E) 14-oxo-1 4-— [(2-phenylethyl) amino] — 2-ethylbutenoate ((E) -ethyl 4-oxo-4-[(2-phenylethyl) amino] -2-butenoate (compound 1 1))

 1-Ethyl 3- (3-dimethylaminopropyl) carposimid 'hydrochloride 9.5 g was added to a methylene chloride solution of 7.2 g of monoethyl fumarate and 5.6 g of ^ -phenethylamine, and triethylamine &. 9 mL was added, and the mixture was stirred at room temperature overnight. The reaction solution was washed sequentially with water, 1N HCl, water, a saturated aqueous solution of sodium hydrogen carbonate 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 dried under reduced pressure to obtain 3.3 g (yield 45%) of Compound 11.

Production example 1 2

(E) 14-oxo2 4-[(2-phenylenyl) 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, 8 N sodium hydroxide 3 Om, and water 1 Om 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 adjust the pH to an acidic side. The precipitated crystals were collected by filtration, washed with water and acetone in that order, and dried under reduced pressure to obtain 1.2 g (yield 68%) of Compound 12.

Production example 1 3

 Synthesis of 4-oxo- 4-[(2-phenylethyl) amino] monobutyric acid (4-Oxo-4-[(2-phenylethyl) amino] -butanoic acid (Compound 13))

 In Preparation Example 1, the procedure was the same as in Preparation Example 1 except that succinic anhydride was changed to 10.7 g, and 2- (p-tolyl) ethylamine was replaced by —phenylethylamine 12.4 g. Thus, 15.8 g (yield 72%) of compound 13 was obtained.

Production example 1 4

 Synthesis of 4-oxo- 4-[(2-phenylethyl) amino]-methyl butyrate (Methyl 4 -0X0-4- [(2-phenylethyl) amino] -butanoate (Compound 14))

 4.8 g of 1-ethyl 3- (3-dimethylaminopropyl) hydroformamide hydrochloride was added to 5 g of the methanol solution of compound 13 obtained above, and 2.5 g of triethylamine was added. Was added and stirred at room temperature overnight. The solvent was distilled off under reduced pressure, methylene chloride was added, and the mixture was washed sequentially with water, 1N HCl, water, a saturated aqueous solution of sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate, and then methylene chloride under reduced pressure. Was removed. The obtained crystals were recrystallized with a mixed solvent of hexane, ethyl acetate and acetone, and dried under reduced pressure to obtain 2.7 g (yield 51%) of compound 14.

Production example 1 5

 Synthesis of 4-oxo-1 4-([2-phenylethyl) amino] -butanamide (4-Oxo-4-[(2-pheny 1 ethy 1) ami no] -bu tanami de (compound 15))

To 5.O g of the compound 13 obtained in Production Example 13 was added thionyl chloride 5 OniL, and the mixture was stirred at room temperature for 10 minutes. Thionyl chloride was distilled off under reduced pressure, and 15 mL of acetone was added and dissolved.Then, it was added to aqueous ammonia (28%) which had been ice-cooled beforehand. The mixture was stirred under cooling for 15 minutes. After the precipitated crystals were collected by filtration, they were sequentially washed with acetonitrile and aceton. The obtained crystals were recrystallized from methanol and dried under reduced pressure to obtain 1.3 g (yield: 23%) of compound 15.

Production Example 1 6

 4-oxo-4-1-[(3-phenylpropyl) amino] -methyl butyrate (Methyl

Synthesis of 4 -0X0- 4-[(3-phenyl propyl) amino] -butanoate (Compound 16)

 To 6.8 g of 3-phenylpropylamine, 4 OmL of methylene chloride was added, and 5.3 g of triethylamine was added while stirring under ice cooling, followed by further stirring. To this, 8.O g of methylsuccinyl chloride dissolved in 40 mL of methylene chloride was added, and the mixture was stirred for about 4 hours. After completion of the reaction, water was added and the mixture was separated. The methylene chloride phase was washed successively with 1N HCl, water, a saturated aqueous solution of sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate, and methylene chloride was distilled off under reduced pressure. . The obtained crystals were purified by a silica gel column and dried under reduced pressure to obtain 8.8 g (yield 72%) of compound 16.

Production Example 1 7

 Synthesis of 4-oxo2-[[(4-Phenylbutyl) amino] methyl butyrate (Methyl 4 — 0X0—4 — [(4-phenylbutyl) amino] -butanoate (compound 17)) 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 phenylpropylamine.

Production example 1 8

 5-oxo-one 5— [(2-phenylethyl) amino] Methyl monovalerate

Synthesis of 5 -0X0- 5— [(2-phenylethyl) amino] -pentanoate (Compound 18)

In Preparation Example 16, 7.0 g of / 3-phenylene-lamine was used instead of 3-phenylpropylamine, and methyl (4-chlorophos) was used instead of methylsuccinyl chloride. Mille) Butylate (10.0 g) was used to prepare triethylamine in the same manner as in 6.1 Production Example 16 to obtain 8.9 g (yield 63%) of compound 18.

Production example 1 9

 Synthesis of Methyl 6-oxo-6-[(2-phenylethyl) amino] -hexanoate (Compound 19) 6-oxo2 6-[(2-phenylethyl) amino] caproate

 Methylene chloride 8 On! Was added to 10.0 g of monomethyl adipate, 7.0 g of 3-phenethylamine was added, and the mixture was stirred for 30 minutes under ice cooling. Next, 6.3 g of triethylamine was added to a solution of 11.9 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride in 11.9 g of methylene chloride, and the mixture was stirred at room temperature overnight. Thereafter, water was added thereto, and the mixture was separated. The resulting mixture was post-treated in the same manner as in Production Example 16 to obtain 10.9 g (yield 74%) of compound 19.

Production Example 20

 Synthesis of 4- (1-phenyl) ethyl 4-butyrate (Ethyl 4--0X0- 4-[(2-phenylethyl) amino] -butanoate (Compound 20)) Preparation Example 16 Except that 7.0 g of 3-phenylethylamine was used instead of 3-phenylpropylamine and 10.3 g of ethylsuccinyl chloride instead of methylsuccinyl chloride, and that the amount of triethylamine was 6.1 g. In the same manner as in Production Example 16, compound 20 was obtained.

Production Example 2 1

 Synthesis of 4-oxo-41-[(2-phenylethyl) amino] propyl monobutyrate (Propyl 4--0X0- 4-[(2-phenylethyl) amino] -butanoate (Compound 21))

After adding 1.0 mL of n-propanol to 0.13 g of Compound 13 and adding 0.87 g of paratoluenesulfonic acid while stirring at room temperature, the mixture was stirred at 78 to 80 ° C for 1 hour. It was cooled and the solvent was distilled off. Methylene chloride and water are added to the obtained crystals, and liquid separation is performed. The methylene chloride phase was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate, and methylene chloride was distilled off under reduced pressure. This was left at room temperature and subjected to solid-liquid separation to obtain 8.2 g (yield 69%) of compound 21.

Production Example 2 2

 Synthesis of Isopropyl 4-I-oxo- 4-[(2-phenylethyl) amino] -butanoate (Compound 22) 4- (oxo-)-4-[(2-phenylethyl) amino]

 Production Example 21 was repeated in the same manner as in Production Example 21 except that isopropanol 10 OmL was used instead of n-propanol. Then, the obtained crystals were purified by a silica gel column and dried under reduced pressure to obtain 6.1 g (yield 51%) of compound 22.

Production example 2 3

 4-oxo- 4-— [[2- (2-chlorophenyl) ethyl '] amino] monobutyric acid Methinole (Methyl 4-oxo- 4 -— [[2- (2-chlorophenyl) ethyl] amino] monobutanoate (compound 23) Synthesis of)

 In Preparation Example 16, 6.7 g (yield) was obtained in the same manner as in Preparation Example 16 except that 8.0 g of 2- (2-chlorophenyl) ethylamine was used instead of 3-phenylpropylamine. 50%) of compound 23.

Production Example 24

 4-oxo-1 41-C [2- (3-chlorophenyl) ethyl] Rmino] methyl monobutyrate (Methyl 4-oxo- 4-[[2- (3-chlorophenyl) ethyl] amino] amino butanoate (compound 24 Synthesis of))

 10.9 g in the same manner as in Preparation Example 16 except that 8.0 g of 2- (3-chlorophenyl) ethylamine was used in Preparation Example 16 in place of 3-phenylpropylamine. Compound 24 was obtained (yield: 79%).

Production example 2 5 4-oxo-1 4 -— [[2- (4-Chlorophenyl) ethyl] amino] Methyl 4-butyrate (Methyl 4-oxo-4 — [[2- (4-chlorophenyl) ethyl] amino] aminobutanoate (Compound 25 Synthesis of))

 10.2 g of Production Example 16 in the same manner as in Production Example 16 except that 8.0 g of 2- (4-chlorophenyl) ethylamine was used instead of 3-phenylpropylamine. Compound 25 was obtained (yield: 75%).

Production Example 2 6

 Methyl 4-oxo- 4- [2- (4-fluorophenyl) ethyl] amino] butanoate (4- [4- (4-Fluorophenyl) ethyl] amino] Synthesis of compound 26)))

 11.2 g in the same manner as in Preparation Example 16 except that 6.9 g of 2- (4-fluorophenyl) ethylamine was used instead of 3-phenylpropylamine in Preparation Example 16 Compound 26 was obtained (yield 89%).

Production Example 2 7

 4- [2- (4-bromophenyl) ethyl] amino] -methyl butyrate (Methyl 4-oxo—4 — [[2- (4-bromophenyDethyl] amino] -butanoate (compound 27)) Synthesis

 In Preparation Example 16, 8.0 g of 2- (4-bromophenyl) ethylamine was used instead of 3-phenylpropylamine, and 6.4 g of methylsuccinyl chloride and 4.2 g of triethylamine were used. In the same manner as in Production Example 16 except that the amount was changed to 1 g, 10.9 g (yield 89%) of compound 27 was obtained.

Production Example 2 8

 Methyl 4-oxo- 4--[[2- (4-iodophenyl) ethyl] amino] butanoate (Compound 2) 4- (4- (4-iodophenyl) ethyl) amino] 8) Synthesis of)

In Preparation Example 16, 2- (4-phosphate) was used instead of 3-phenylpropylamine. (Fenyl) ethylamine. Dehydrated with anhydrous magnesium sulfate and dried in the same manner as in Production Example 16 except for using 8.O g of methylsuccinyl chloride in 5.3 g and triethylamine in 3.5 g. Then, this was dried overnight under reduced pressure at room temperature to obtain 10.2 g (yield 87%) of compound 28.

Production Example 2 9

 5 Synthesis of Methyl 5-oxo-5-[(3-phenylpropyl) amino]-pentanoate (Compound 29), 5-oxo-5-[(2-phenylpropyl) amino] monovalerate

 In Preparation Example 16, 3-genylpropylamine was 8.0 g and triethylamine was 6.2 g, and methyl (4-chloroformyl) butyrate was used instead of methylsuccinyl chloride. 12.5 g (yield 82%) of compound 29 was obtained in the same manner as in Production Example 16 except that 2 g was used.

Production Example 30

 4 一 1 一 4 41 2 [[2— (3,4 ー ジ -dichlorophenyl) ethyl] Amino] methyl monobutyrate (Methyl 4-—oxo—4 一 [[2— (3,4-dichlorophenyl) ethyl ] Synthesis of amino] -butanoate (Compound 30))

 In Preparation Example 16, 6.9 g of methylsuccinyl 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. Except for using it, 10.8 g (yield 84%) of compound 30 was obtained in the same manner as in Production Example 16.

Production example 3 1

Synthesis of 4-oxo2-[(4-phenylbutyl) amino] -butyric acid (4-Oxo-41-[(4-phenylphenylbutyl) amino] -butanoic acid (Compound 31)) Succinic anhydride to 7.9 g 4 OmL of acetone was added, dissolved in 15 m of acetone, and 1.1 Og of 1-amino-4-phenylbutyric acid was added. The mixture was stirred at room temperature for 5 minutes, and allowed to stand still at 15 ° C and cooled. . The precipitated crystals were collected by filtration under reduced pressure, and acetone 5 Onl was added. After recrystallization, the obtained crystals were washed with cold acetone and dried under reduced pressure.

10.0 g (yield 56%) of compound 31 was obtained.

Production example 3 2

 Synthesis of 6-oxo-1 6 — [(2-phenylethyl) amino] -cabronic acid (6-Oxo-6-[(2-phenylethyl) amino] -hexanoic acid (Compound 32)) 1.3 g of adipic anhydride was used instead of succinic acid, and 1.6 g of the same as in Preparation Example 1 except that 1.2 g of 3-phenethylamine was used instead of 2 (p-tolyl) ethylamine. Compound 32 was obtained (yield 65%).

Production example 3 3

 Of 4- [2- (2-chlorophenyl) ethyl] amino] -butyric acid (4-Oxo—4-[[2- (2-chlorophenyl) ethyl] amino] -butanoic acid (compound 33)) Synthesis

 To 7.5 g of succinic anhydride, add 5 OmL of acetone, dissolve in 50 m of acetone, add 11.0 g of 2- (2-chlorophenyl) ethylamine, and stir at room temperature for 5 minutes. It was allowed to cool at 15 ° C. The precipitated crystals were collected by filtration under reduced pressure, recrystallized by adding acetone 8 OiiiL, and the obtained crystals were washed with cold acetone and dried under reduced pressure to give 6.4 g (yield 31%). ) Was obtained.

Production example 3 4

 Synthesis of 4- [2- (3-chlorophenyl) ethyl] amino] monobutyric acid (4-0x0—4—L [2-3-chlorophenyl) ethyl] amino] -butanoic acid (compound 34)

 In Preparation Example 33, except that succinic anhydride was changed to 7.9 g and 1-1.0 g of 2- (3-chlorophenyl) ethylamine was used instead of 2- (2-chlorophenyl) ethylamine In the same manner as in Production Example 33, 12.3 g (yield 69%) of compound 34 was obtained.

Production example 3 5 4-oxo-1-41 [[2- (4-Fluorophenyl) ethyl] amino] -butyric acid (4-0x0—4-[[2- (4-fluorophenyl) ethylj amino] —butanoic acid (compound 3 5) Synthesis of)

 Production Example 33 Production Example 3 was repeated except that succinic anhydride was changed to 8.4 g, and 1-1.0 g of 2- (4-fluorophenyl) ethylamine was used instead of 2- (2-chlorophenyl) ethylamine. As in Example 33, 2.3 g (yield 12%) of compound 35 was obtained.

Production example 3 6

 4—oxo— 4 — [[2- (4-Bromophenyl) ethyl] amino] —Rooster

Synthesis of (4— Oxo— 4— [[2- (4-bromophenyl) ethyl] amino] -butanoic acid (Compound 36)

 To 2.1 g of succinic anhydride was added 5 OmL of acetone, dissolved in 50 mL of acetone, 4.0 g of 2- (4-promophenyl) ethylamine was added, and the mixture was stirred at room temperature for 5 minutes. It was left to cool at 5 ° C. The precipitated crystals were collected by filtration under reduced pressure, washed with cold acetone, and dried under reduced pressure to obtain 3.8 g (yield 65%) of compound 36.

Production example 3 7

 4- [2- (4-diphenyl) ethyl] amino] —butyric (4-0x0—4 — [[2- (4-iodophenyl) ethyl] amino] -butanoic acid (compound 37) Synthesis of

 To 1.7 g of succinic anhydride was added 100 mL of acetone, dissolved in 100 ml of acetone, and 4.0 g of 2- (4-phenylphenyl) ethylamine was added. The mixture was stirred and allowed to cool at 115 ° C. The precipitated crystals were collected by filtration under reduced pressure, washed with cold acetone, and dried under reduced pressure to obtain 2.9 g (yield 52%) of compound 37.

Production example 3 8 Synthesis of 5-oxo-5-[(3-phenylpropyl) amino] monovaleric acid (5-Oxo) 5-[(3-phenylpropyl) amino] -pentanoic acid (compound 38) Glutaric anhydride 10 To 30 g of acetone, add 30 m of acetone, dissolve in 30 m of acetone, add 11.0 g of 3-phenylpropylamine, stir at room temperature for 5 minutes, and add The solution was allowed to cool by standing at C. The precipitated crystals were collected by filtration under reduced pressure, recrystallized by adding 10 mL of acetone, washed with cold acetone, and dried under reduced pressure. g (yield 11%) of compound 38 was obtained.

Production example 3 9

 4-oxo2- 4-[[2- (3,4-dichlorophenyl) ethyl] amino] -butyric acid (4-Oxo-4-1 [[2- (3,4-dichlorophenyl) ethyl] amino] -butanoic acid (compound 3 9) Synthesis of)

 To 2.3 g of succinic anhydride, add 25 mL of acetone, dissolve in 20 ml of acetone, add 4.0 g of 2- (3,4-diclocophenyl) ethylamine, and stir at room temperature for 5 minutes And cooled by standing at −15 ° C. The precipitated crystals were collected by filtration under reduced pressure, washed with cold acetone, and dried under reduced pressure to obtain 5.0 g (yield 83%) of compound 39.

Compound 0 obtained above! Table 1, Table 2, Table 3, Table 4, and Table 5 show the physical properties of ~ 39.

table 1

^{Mass l H-NMR (200MHz,} DMSO- d 6 (5ppm) (FAB'M + l)

1, J π u 1 .on, mi> ι · viii, J ο. Ιΐώ

 7.08 (4Η, s), 3.27-3.17C2H, m),

 2.68-2.60 (2H, t, J = 7.3Hz),

 2.45-2.29 (4H, m), 2.26 (3H, s)

 _ / Ao

 1

,

m cr ΎΜ U dno, /, * 11, I (JJl

 7.32C2H, d, J = 8.5Hz), 7.22 (2H, d, J = 8.4Hz), 3.29-3.19C2H, m), 2.72-2.64C2H, †, J = 7.2Hz), 2.45-2.24 (4H, m)

 1¾J U ½ ΔΌ ί d \ i Ul 0 * i Ji,, O /. LllZ /

 7.98C1H, t, J = 5.4Hz 7.49C1H, d, J = 8.6Hz), 3.37-3.27 (2H, m), 2.85-2.52C2H, t, J = 7.0Hz, 2.45-2.24 (4H, m)

Compound 05 238 12.0C1H, brs), 9.2 (lH, brs),

 7.88C1H, t, J = 5.5Hz), 6.98 (2H, d, J = 8.2Hz), 6.67 (2H, d, J = 8.4Hz), 3.23-3.13C2H, m), 2.61-2.50 (2H, m ), 2.45-2.25 (4H, n0 compound 06 208 12.05 (1H, brs), 8.35C1H, t, J = 5.7Hz).

 7.34-7.18C5H, m), 4.26 (2H, d, J = 5.9Hz), 2.51-2.34 (4H, m)

Compound 07 236 12.05 (lH, brs), 7.86 (lH, t, J = 5.3Hz),

 7.31-7.12C5H, m), 3.09-3.00 (2H, m),

 2.60-2.50 (2H, m), 2.43-2.27 (4H, m),

 1.75-1.60 (2H, m)

Compound 08 208 12.0 (1H, brs), 8.14 (1H, t, J = 5.2Hz),

 7.33-7.16C5H, m), 3.33-3.23 (2H, m \

 3.ll (2H, s), 2.7lC2H, t, J = 7.4Hz

Compound 09 236 12.05 (lH, brs), 7.88 (1H, t, J = 5.4Hz),

 7.32-7.1 C5H, m), 3.31-3.21 (2H.m),

2.69 (2H, t, J = 7.4Hz), 2.21-2.04C4H, m), 1.76-1.61 (2H, m) Table 2

Mass-NMR (200MHz DMSO- d ₆ o ppm (FAB'M + l)

1 object 1 0 220 13 n (lH hrs) 9 19 (1H t 7 34 7 16 (5H n \)

 6.39C1H, d J = 12.5Hz), 6.23C1H, d, J = 12.5Hz \ 3.47-3.37C2H, m), 2.79 (2H, t, J = 7.4Hz) Compound 1 1 248 8.6K1H, t 7.34-7.20 (5H, m),

 6 99 (1H d J = 15 6Hz) 6 56 (1H d J = 15 6Hz

4.23-4.13 (2H, q, J = 7.

 3.46-3.39 (2H, m), 2.77 (2H, t J = 7.3Hz),

1.24C3H, t, J = 7.1Hz) Compound 1 2 220 12.8C1H, brs), 8.57 (lH, t, J = 5.5Hz),

 7.34-7.16 (5H m), 6.9K1H, d, J = 15.3Hz \ 6.5K1H, d, J = 15.3Hz 3.45-3.35 (2H,), 276C2H, t, J = 73Hz Compound 1 3 222 12.07 (brs 7.94 (1H, t J = 5.4Hz

 7.33-7.16C5H, m 3.30-3.20 (2H, m

 2.73-2.66C2H, m), 2.52-2.25 (4H, m)

Compound 1 4 236 7.96 (1H, t 7.32-7.18C5H, m 3.57 (3H, s

 3.30-3.19 (2H m), 2.68 (2H, t, J = 7.4Hz), 2.51-2.45 (2H, m), 2.36-2.30 (2H, m) Compound 1 5 221 7.94 (1H, t), 7.33C1H , brs), 7.29-7.19 (5H, m),

 6.74 (1H, brs), 3.30- 3.20 (2H m,

2.69C2H.t, J = 7.4Hz), 2.28 (4H, s

Three

4-NMR (200MHz CDC 3 o ppm)

1 Compound ΎΜ ^Γ > 270 7 26C2H d J = 8 4Hz 7 12 (2H d J = 8 4Hz

 5.75 (1H, brs), 3.67 (3H, s

 3.46C2H, q J = 6.9 Hz), 2.78 (2H, t J = 7.OHz), 2.65 (2H, t J = 6.7 Hz), 2.43 (2H, t, J = 6.5 Hz compound 2 6 254 7.19-7.12 (2H, m 7.03-6.94 (2H m,

 5.75C1H, brs), 3.67C3H, s

 3.46 (2H, q J = 6.9 Hz), 2.78 (2H, t J = 7.0 Hz 2.65 (2H, t, J = 6.7 Hz 2.43 (2H, t J = 6. 7Hz) Compound 2 7 315 7.43C2H, d, J = 8.3Hz), 7.07 (2H, d, J = 8.4Hz),

 5.72C1H, brs), 3.68 (3H, s

 3.46C2H, q, J = 6.9 Hz), 2.77 (2H.t, J = 7.OHz), 2.65 (2H, t, J = 6.7 Hz), 2.43 (2H, t J = 6.8 Hz) 1 ^ \ ¥ \ 2 £ 8 362 7 60 (2H d J = 8 3Hz) 6 93C2H d J = 8 3Hz

 5.82C1H, brs), 3.66 (3H, s)

 3.43 (2H, q, J = 6.9Hz), 2.70 (2H, t, J = 7.0Hz 2.63C2H, t, J = 6.5Hz), 2.43 (2H, t, J -6.5Hz) Compound 2 9 264 7.32-7.15C5H, m), 5.58C1H, brs), 3.66 (3Hs),

 3.46 (2H, q J = 6.9Hz 2.64 (2H, t J = 7.6Hz), 2.36C2H, t, J = 7.0Hz), 2.18 (2H t, J = 7. 2Hz), 2.00-1.76 (4H, m)

Compound 3 0 304 7.39-7.27 (2H, m 7.07-7.01 (1H m),

 5.78 (1H, brs), 3.68 (3H s

3.47C2H, q, J = 6.9 Hz), 2.77 (2H, t, J = 7.OHz), 2.65 (2H, t J = 6.8 Hz 2.42C2H, t J = 6.4 Hz )

Five

Mass ¹ H-NMR (200MHz, DMSO-d ₆ o ppm) (FAB.M + 1)

I 1 "· thing \ J 3 o] 250 11 g (iH hrs 779C1H t J = 54Hz)

 7.29-7.10C5H, m), 3.08-2.98 (2H, m, 2.58-2.48C2H, m), 2.40-2.22C4H, n

 1.58-1.33C4H, m)

Compound 32 259 11.95C1H, brs 7.84 (1Ht, J = 5.4Hz),

 7.30-7.16 (5H m), 3.29-3.19 (2H, m), 2.71-2.64 (2H m 2.20-1.99 (4H m

 1 46-1 42C4H, m)

Compound 33 256 12.04C1H, brs 7.96C1H, t, J = 5.4Hz),

 7.42-7.18C4H, m), 3.31-3.2K2H, m), 284-278C2H m) 244-207C4H m) Compound 34 256 12.04C1H, brs), 7.79 (1H, t, J = 5.4Hz),

 7.34-7.14C4H, m), 3.30-3.20 (2H, m), 2.72-2.65C2H, m), 2.44-2.07 (4H, m) Compound 35 240 12.04C1H, brs), 7.89 (lH, t J = 5.4 Hz

 7.24-7.01 (4H, m), 3.26-3.17 (2H, m), 2.69-2.62 (2H, m), 2.43-2.23 (4H, m) Compound 36 300 12.0 (1H, brs), 7.90 (1H, t J = 5.4Hz),

 7.44 (2H, d J = 8.4Hz), 7.15C2H, d J = 8.2Hz 3.27-3.17C2H, m), 2.69--2.61 (2H, m

 2.43-2.07C4H, m ')

 1 object Ί J 37 348 11 R (1H brs) 790C1H t J = 55Hz)

 7.60 (2H, d, J = 8.1Hz), 7.00 (2H, d J = 8.3Hz), 3.22 (2H, q, J = 6.9Hz), 2.64 (2H, t, J = 7.1Hz), 2.43-2.23 C4H, m)

Compound 38 250 12.0C1H, brs), 7.82 (1H, t, J = 5.4Hz

 7.31-7.13C5H, m), 3.09-2.99 (2H, m), 2.60-2.50 (2H, m 2.24-2.10 (4H, m), 2.06-1.60C4H, m)

Compound 39 290 12.05 (1H, brs), 7.92 (1H, t J = 5.4Hz),

 7.55-7.48 (2H, m, 7.23- 7.18 (1H, m

3.32-3.21 (2H, m), 2.74-2.67 (2H, m, 2.45-2.23 (4H, m) Example 1

 Rooting promotion effect by immersion treatment of azuki cut chemical solution

Azuki seeds (variety name: Erimoshozu, sold by Snow Brand Seed Co., Ltd.) are sown in a commonly used nursery box (35cm x 25cm x 5cm depth) filled with vermiculite (Kushiro Coal Drying Co., Ltd.). The plants were cultivated for 12 days under fluorescent light (2200 looks, 20 ° C). The fully developed primary leaves were cut off at a height of 3 cm, and the shoots at the shoot apex were also excised to prepare test materials. Among the 39 plant growth regulators prepared in Production Examples 1 to 39, Compounds 1, 14, 15, and 16 to 30 were directly diluted with distilled water, and the others were sodium hydroxide. The solution was diluted with distilled water while neutralizing with an aqueous solution to prepare an aqueous solution having a concentration of 7 ppm and 70 ppm. The cuts of the above-mentioned azuki test material were immersed in these aqueous solutions for 72 hours. After the treatment, the base was washed with water, and the base was immersed in distilled water for 4 days and cultured, and the number of adventitious roots generated was measured. As a control, those treated with distilled water were cultured, and the number of adventitious roots was similarly measured. As shown in Table 6, Table 7 and Table 8, a higher rooting promoting effect was observed as compared with the number of rooting in the control group. , Especially at a concentration of 7 Oppm, promote rooting of compounds 01 to 03, 06 to 10, 13, 14, 14, 16 to 26, 29, 31 to 36, 38, 39 Highly active, at 7 ppm, rooting promoting activity of compounds 03, 07, 09-11, 13, 14, 14, 16, 17, 20-32, 35-38 Was high.

W / 4577 Table 6 Test compound concentration Root number Relative value

 ppm (%) Compound 0 1 7 0 2 5.6 4 5 7

 7 1 4.4 2 5 7 Compound 0 2 7 0 2 7.2 4 8 6

 7 1 4.2 2 5 4 Compound 0 3 7 0 2 8.0.5 0 0

 7 1 6.6.2 9 6 Compound 0 4 7 0 2 1.6 3 8 6

 7 1 1.4 2 0 4 Compound 0 5 7 0 2 1.4 3 8 2

 7 1 1.2 2 0 0 Compound 0 6 7 0 2 9.6 5 2 8

 7 1 4.4 2 5 7 Compound 0 7 7 0 3 6.2 6 4 6

 7 1 9.6 3 5 0 Compound 0 8 7 0 2 6.6 4 7 5

 7 1 A A

 丄 ^. 4 o ς 7 Compound 0 9 7 0 3 1.8 5 6 8

 7 ί ο 4 υ Compound 1 0 7 0 3 1.4 5 6 1

 7 1 丄 o Q. 9 Q ο οι ο Compound 1 1 7 1 8.8 3 3 6 Compound 1 2 7 0 1 6.6 2 9 6

 7 1 4.2 2 5 4 Compound 1 3 7 0 2 6.6 4 7 5

 7 1 5.0 0 2 6 8 Compound 1 4 7 0 3 2.4 5 7 9

 7 2 4.04 2 9 Compound 1 5 7 0 1 8.0 0 3 2 1

7 1 0.8 1 9 3 Table Ί Test compound concentration (ppm) Root number Relative value (%) Compound 16 7 0 3 9.27 0 0

 7 2 6.0 4 6 4 Compound 1 7 7 0 4 6.0 0 8 2 1

 7 2 6.0 4 6 4 Compound 1 8 7 0 4 2.2 7 5 4

 7 1 4.6 2 6 1 Compound 1 9 7 0 4 1.8 7 4 6

 7 1 3.8 2 4 6 Compound 2 0 7 0 2 6.6 4 7 5

 7 1 8.8 3 3 6 Compound 2 1 7 0 2 7.4 4 8 9

 7 2 3.04 4 1 1 Compound 2 2 7 0 2 7.4 4 8 9

 7 1 5.0 2 6 8 Compound 2 3 7 0 3 1.2 5 5 7

 7 2 5.8 4 6 1 Compound 2 4 7 0 4 3.6 7 7 9

 7 2 5.4 4 5 4 Compound 2 5 7 0 3 4 8 6 2 1

 7 2 7. 0 4 8 2 Compound 2 6 7 0 3 7.8 6 7 5

 7 2 6.2 4 6 8 Compound 2 7 7 3 4.0 6 0 7 Compound 2 8 7 4 1. 8 7 4 6 Compound 2 9 7 0 5 0 .0 8 9 3

7 1 9.8 3 5 4 Compound 3 0 7 3 2.2 5 7 5 Table 8

Example 2

 Comparison of Rooting Promoting Effect with Auxin by Azuki Cut Chemical Dipping Treatment

Compound 13 shown in Production Examples 13 and 14, compound i4, and indoleacetic acid, which is an auxin-based compound, were diluted with distilled water to various concentrations. Compound 13 and indole acetic 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 shown in Table 9, the compound 13 had a significantly higher rooting number than indoleacetic acid at 20 ppm or more. Compound 14 also had a higher rooting number than indoleacetic acid at all concentrations, especially at a concentration of 600 ppm. Indole acetic acid is also harmful. Compounds 13 and 14 were found to be harmless at the resulting concentrations (at least 6 Oppm)-wide applicable concentrations. The relative value is the number of roots expressed in% when the number of roots of the control is 100.

 Table 9

 The tree died.

Example 3

 Effect of tomato on cell seedling raising seedlings

Using a hard plastic cell tray with a size of 4.5 cm x 4.5 cm and 98 holes per well, it is filled with a dedicated culture soil (Scotts, Scotts-Sierra Horticultural Products) containing peat as a main component. Tomato seeds (cultivar name: Ochiyobo, sold by Snow Brand Seed Co., Ltd.) were cultivated in a glass house with additional fertilization. On the 16th and 23rd days after seeding, the above compound 13, compound 14 and indolebutyric acid (IBA), a commercially available product 2-methyl-4 'Ethyl butyrate (MCPB) solution was sprayed at 50 Om per tray. In preparing the aqueous solution, compound 14 was directly diluted with deionized water, and compound 13 and indolebutyric acid were diluted with deionized water while neutralizing with an aqueous sodium hydroxide solution. The 2-methyl 4-chlorophenethyl butyrate (MCPB) was prepared by diluting commercially available Madec emulsion (manufactured by Agro-Kanesha Co., Ltd., containing 20% of MCPB). Deionized water was used as a control.

 On the 29th day after sowing, the root dry weight, the total dry weight, the plant height, and the length of the first cotyledon of the cotyledon were measured in 15 x 2 replicates of 15 individuals. The results are shown in Table 10. The values in parentheses in the table indicate the relative values in terms of% when the control group is 100 (the same applies hereinafter). Root dry weight increased by 7% or more in the treatments with all concentrations of compound 13 and compound 14, indicating that the root-promoting effect was also high in actual tomato seedlings.

The total dry weight was significantly increased in the 10 ppm and 100 ppm treatments of compound 13 and compound 14, and a growth promoting effect was also observed. In addition, the effect of shortening the plant height was also observed in the compound 13 and compound 14 treated with 100 ppm. These effects such as an increase in root mass, promotion of growth, and suppression of stunt growth are desirable at the time of raising seedlings, and no phytotoxicity was observed. Thus, the usefulness of Compounds 13 and 14 was confirmed. On the other hand, for control I, indolebutyric acid caused phytotoxicity at a concentration of 100 ppm or more, and 2-methyl-4 monoethyl phenoxybutyrate at 10 ppm or more, and no phytotoxicity. i O ppm Indole butyric acid also had less effect on root dry weight than compounds 13 at all concentrations and compound 14 at 100 ppm. Table 10

 * Leaf bent.

 ** Leaf withered, growth stopped

(Note) Diluted Madek emulsion (manufactured by Agro-Kaneshiyo Co., Ltd., containing 20% MCPB)

Example 4

 Effect of procoli on cell-grown seedlings.

 Using a hard plastic cell tray with a size of 4 cm x 4 cm and a size of 128 holes, the same method as in Example 3 was used for prococcoli one seed (variety name: Midorine, Sakata seed sales) ). On the 14th and 21st days after seeding, 500 mL of an aqueous solution of compound 13, compound 14, indolebutyric acid and 2-methyl 4-chlorophenyloxyacetic acid ethyl ester prepared in the same manner as in Example 3 was used for each tray. Sprayed. On the 29th day after the seeding, each item was measured in the same manner as in Example 3 with 16 individuals × 2 repetitions. The results are shown in Table 11. Root dry matter increased in the treated groups at 100 ppm and 100 ppm of Compound 13 and at all concentrations of Compound 14. From this, it was confirmed that the root-promoting effect was high even in the actual prococcy growing seedlings. The total dry weight increased in the 1 O ppm and 100 ppm treatments of Compound 13 and Compound 14, and a growth promoting effect was also observed.

In the 100 ppm treatment of Compound 13 and Compound 14, the effect of shortening the internode length between the cotyledon node and the first true leaf node, which was easily elongated in the seedlings, was also observed. These effects of increasing root mass, promoting growth, and suppressing stunt growth were desirable at the time of raising seedlings, and no phytotoxicity was observed, and the usefulness of Compounds 13 and 14 was confirmed. On the other hand, indolebutyric acid, which was used as a comparative control, caused phytotoxicity at a concentration of 100 ppm or more, and 2-methyl-4-octanol o-phenyloxybutyrate at all concentrations, and no phytotoxicity. Even at 1 O ppm indole butyric acid, its effect on root dry weight and total dry weight was more inhibitory and less practical than the control. Table 11

 * Abnormal growth of leaves and bending of stem were observed.

 ** Leaf withered.

(Note) Diluted emulsion (made by Agro Kanesho Co., Ltd., containing 20% MCPB)

Example 5

 Effect of lettuce on seedlings for cell formation

 Lettuce seeds in the same manner as in Example 3 using a hard plastic cell tray with a hole size of 4 cm x 4 cm and 128 holes (cultivar name: Karma MR, Nitto Agricultural Seedlings Co., Ltd.) Was sown. On days 10 and 18 after seeding, an aqueous solution of compound 13, compound 14, indolebutyric acid, and 2-methyl-4 monochlorophenoxyacetic acid ethyl ester prepared in the same manner as in Example 3 was added to 50 / tray. O mL was sprayed. On the 25th day after sowing, the root dry weight and total dry weight were measured in 16 individuals × 2 repetitions. The results are shown in Table 12. The dry weight of the roots was increased by the treatment of Compounds 13 and 14, and it was recognized that the rooting promoting effect was high even in the actual lettuce seedlings. The total dry weight also increased, and a growth promoting effect was also observed. Since these effects are desirable at the time of raising seedlings and no phytotoxicity was observed, the usefulness of compound 13 and compound 14 was confirmed. On the other hand, phytotoxicity was caused by 2-methyl-4-monochlorophenyloxybutyrate, and the effect of indolebutyric acid, which was not toxic, was lower than that of Compounds 13 and 14.

 Table 1 2

 ** Leaf withered.

(Note) Diluted Madek emulsion (manufactured by Agro-Kanesha Co., Ltd., containing 20% MCPB). Example 6

 Effect of green pepper seedling on seedling

 Using a plastic plastic tray with a size of 4.5 cm x 4.5 cm and 98 holes, the same method as in Example 3 is used for pepper seeds (variety name: Ace, Yuki Seed and Seed Co., Ltd.) Was sown. On the 12th day and 21st day after the seeding, 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 in 15 individuals × 2 replicates. The results are shown in Table 13. Regarding the root dry weight, Compound 13 showed an increase of 75% or more in all concentrations, and Compound 14 showed an increase of more than 60% in the O ppm and 100 ppm treatments.

 From this, it was confirmed that the actual root growth of seedlings was high, but the rooting promoting effect was high. The leaf area and the total dry weight were also increased in all of the compound 13 and compound 14 treatments, and a growth promoting effect was also observed. In addition, the ratios of the aboveground and underground weights in all treatment plots were smaller than those in the control plots, which confirmed that root development was promoted without lengthening. The effects of increasing root mass, promoting growth, and reducing the aboveground and underground weight ratios were desirable during seedling raising, and no phytotoxicity was observed, confirming the usefulness of Compounds 13 and 14.

 Table 13 Test Concentration Root Dry Matter Leaf Area Total Dry Matter Aboveground Compounds (ppm) (g / 15 individuals) (cm 2/15 individuals) (g / 15 individuals) Lower weight ratio Compound 1000 0.218 (198 %) 501.6 1.833 7.4

1 3 100 0.206 (187%) 613.1 2.032 8.9

 10 0.193 (175%) 546.2 1.948 9.1 Compound 1000 0.142 (129%) 448.0 1.644 10.6

1 4 100 0.197 (179%) 556.5 1.951 8.9

10 0.177 (160%) 513.0 1.731 8.9 Control 0 0.110 (100%) 403.4 1.346 11.3 Example 7

 Effect of tomato cell seedlings on treatment during transplantation

 Tomato seedlings were grown in the same manner as in Example 3 using a hard plastic cell tray having a size of 4.5 cm × 4.5 cm and 98 holes. An aqueous solution of compound 13 and compound 14 prepared in the same manner as in Example 3 was sprayed on the seedlings 30 days later at 50 OmL per tray. The day after spraying, the plants were transplanted to a 12 cm diameter x 1 Ocm deep vinyl pot filled with 55 Om of Sankyo Horticultural Soils (Hokkaido Sankyo Co., Ltd.). On the 1st day after transplantation, each item was measured in the same manner as in Example 5 in 4 repetitions. The results are shown in Table 14. Compounds 13 and 14 increased the dry weight of the roots by 8% or more in the treatments of all concentrations, and it was confirmed that the treatment immediately before transplantation also exerted rooting promoting effect after transplantation. The total dry weight and the number of leaves increased in all treatments, and the growth promotion effect after transplantation was also observed.

 Table 14

Example 8

 Effects of carnation on seedlings

Approximately 5 cm of the tip of the stem was cut off from the parent strain of two varieties of cultivars (variety names: California Elf, California Cotilion, and Snow Brand Seedlings Co., Ltd.), and used as sashimi. About 1 cm of the base of this cutting was immersed in an aqueous solution of compound i3 prepared in the same manner as in Example 3. The control was immersed in deionized water under the same conditions. Twenty-four hours after the start of immersion, the size of one hole is 2.6 cm x 2.6 cm and a 16-hole hard plate is used. The cuttings were cut and sprouted on a nursery bed filled with a culture soil in which perlite and peat were mixed at a ratio of 7: 3 to a plastic cell tray, and cultivated in a glass house. After cutting and buds, 34 to 4 days later, the ratio of rooting individuals was measured by 5 X3 repetitions, and the root dry weight was also measured. The results are shown in Table 15. At all treatment concentrations, root dry matter increased by more than 450% in California and Cotylion, and increased by more than 32% in California Elves, and the proportion of rooting individuals increased by more than 20% in Elves . From these results, it was confirmed that the rooting promoting effect was high also in the cut and raised seedlings of carnation.

 Table 15

Industrial applicability

INDUSTRIAL APPLICABILITY The plant growth regulator and the composition for regulating plant growth of the present invention have a high activity of promoting rooting of plants and have extremely weak side effects such as an action of promoting upgrowth on leaves. It can be used over the entire growing period and is particularly useful as a rooting promoting agent or a composition for promoting rooting at the time of seedling-transplanting. Also, plant tissue It can also be used by adding it to a medium for the purpose of culturing and differentiating roots.

Claims

1. The following general formula (1)

0 0

 ΑΓ 'people (1)

(In the formula, Ar represents a substituted or unsubstituted phenyl group which may be mainly substituted, A represents a linear or branched lower alkylene group, and B represents a linear or branched lower alkyl group. Alkylene or lower

R ¹ represents a hydroxyl group, an amino group or a lower alkoxy group.

A plant growth regulator comprising a compound represented by the formula or a salt thereof as an active ingredient.

 2. Ar force, a halogen atom, a hydroxyl group, a nitro group, a lower alkyl group and a lower alkoxy group, and 1 to 5 groups selected from a substituted or unsubstituted phenyl group. 2. The plant growth regulator according to claim 1, wherein the plant growth regulator is an alkylene group, and B is a linear lower alkylene group or a lower alkenylene group.

3. Ar is phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-hydroxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 4-phenyl A bromophenyl group, a 4-phenylphenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group or a 3,4-dichlorophenyl group, A is a linear alkylene group having 1 to 4 carbon atoms, and B is A straight-chain alkylene group having 1 to 4 carbon atoms or a straight-chain alkylene group having 2 to 4 carbon atoms, wherein R ¹ is a hydroxyl group, an amino group, a methoxy group, an ethoxy group, an n-propoxy group or 2. The plant growth regulator according to claim 1, which is a propoxy group.

4. Ar is phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-bromophenyl, 2 — Black phenyl group, 3 — Black phenyl group or 3, 4-dichloro A lolophenyl 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, and R i is 2. The plant growth regulator according to claim 1, which is a droxyl group, a methoxy group, an ethoxy group, an n-propoxy group, or an i-open oxy group.

5. Ar, A, B, and R ¹ each 4-methylphenyl group, ethylene group, ethylene group and hydroxy group; 4-methoxyphenyl group, ethylene group, ethylene group and hydroxy group; Phenyl group, ethylene group, ethylene group and hydroxy group; phenyl group, methylene group, ethylene group and hydroxy group; phenyl group, trimethylene group, ethylene group and hydroxyl group; phenyl group, ethylene group, Methylene group and hydroxy group; phenyl group, ethylene group, trimethylene group and hydroxy group; phenyl group, ethylene group, cis-vinylene group and hydroxy group; phenyl group, ethylene group, trans-vinylene group and ethoxy group Group; phenyl group, ethylene group, ethylene group and hydroxy group; phenyl group, ethylene Group, ethylene group and methoxy group; 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 and methoxy; 4 monofluorophenyl, ethylene, ethylene And methoxy groups; 4-bromophenyl group, ethylene group, ethylene group and methoxy group; 4-phenyl group, ethylene group, ethylene group and methoxy group; phenyl group, trimethylene group, trimethylene group and methoxy group Groups; 3,4-dichlorophenyl, ethylene, ethylene and methoxy; phenyl, tetramethylene Ethylene group and hydroxyl group; phenyl group, ethylene group, tetramethylene group and hydroxyl group; 2-chlorophenyl group, ethylene group, ethylene group and hydroxy group; 3-chlorophenyl group, ethylene group, ethylene group and 4-hydroxyphenyl group; 4 monofluorophenyl group, ethylene group, ethylene group and hydroxyl group; 4 monobromophenyl group, ethylene group, ethylene group and hydroxyl group; 4 monophenyl group, ethylene group, ethylene group and hydroxyl group; phenyl 2. The plant growth regulator according to claim 1, which is a group, a trimethylene group, a trimethylene group, and a hydroxyl group; or a 3,4-dichlorophenyl group, an ethylene group, an ethylene group, and a hydroxyl group.

 6. The plant growth regulator according to claim 1, which is a plant rooting promoter.

 7. The following general formula (1)

0 0

 , A \ people i

Ar ^Xヽ Ν ^κヽ Β ^κ \ (1)

 Η

(In the formula, Ar represents a fluorine group which may have a substituent, A represents a linear or branched lower alkylene group, and B represents a linear or branched lower alkylene group or lower. Represents an alkenylene group, and R ¹ represents a hydroxyl group, an amino group or a lower alkoxyl group)

A composition for adjusting plant growth comprising a compound represented by the formula or a salt thereof, and a carrier for agricultural chemicals or a fertilizer.

 8. Ar force, a halogen atom, a hydroxyl group, a nitro group, a lower alkyl group and a lower alkyl group and a phenyl group which may be substituted with 1 to 5 groups selected from a lower alkoxyl group, and A is a linear lower group The plant growth regulating composition according to claim 7, wherein the composition is an alkylene group, and B is a linear lower alkylene group or a lower alkenylene group.

9. Ar is phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-hydroxyphenyl, 4-fluorophenyl, 4- A phenyl group, 4-bromophenyl group, 4-chlorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group or 3,4-dichlorophenyl group, wherein 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, and R ′ is a hydroxyl group, an amino group, a methoxy group, an ethoxy group, n The plant growth regulating composition according to claim 7, which is a propoxy group or an i-propoxy group.

10. Ar is a phenyl group, a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-fluorophenyl group, a 4-chlorophenyl group, a 4-bromophenyl group, a 4-phenylphenyl group, a 2 — A chlorophenyl group, a 3-chlorophenyl group or a 3,4-dichlorophenyl group, wherein 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 8. The plant according to claim 7, wherein the plant is a straight-chain ke2ylene group having 2 to 4 carbon atoms, and R ¹ is a hydroxyl group, a methoxy group, an ethoxy group, an n-propoxy group, or an i-open mouth oxy group. Growth regulating composition.

11. Ar, A, B and R 'forces, respectively, 4-methylphenyl group, ethylene group, ethylene group and hydroxy group; 4-methoxyphenyl group, ethylene group, ethylene group and hydroxy group; 4-chlorophenyl group Phenyl, methylene, ethylene and hydroxy; phenyl, trimethylene, ethylene and hydroxy; phenyl, ethylene, methylene and hydroxy; ethylene, ethylene, ethylene and hydroxy; phenyl, methylene, ethylene and hydroxy; phenyl, trimethylene, ethylene and hydroxy; phenyl, ethylene, methylene and hydroxy Phenyl group, ethylene group, trimethylene group and hydroxy 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 hydroxy group; phenyl group, ethyl Phenyl, ethylene, methoxy and methoxyl groups; phenyl, trimethylene, ethylene and methoxyl groups; phenyl, tetramethylene, ethylene and methoxyl groups; phenyl, ethylene, trimethylene and methoxyl groups Groups: phenyl, ethylene, tetramethylene and methoxy; phenyl, ethylene, ethylene A phenyl group, an ethylene group, an ethylene group and an n-propoxy group; a phenyl group, an ethylene group, an ethylene group and an i-propoxy group; a 2-chlorophenyl group, an ethylene group, an ethylene group and a methoxy group; 3-chlorophenyl, ethylene, ethylene, and methoxy groups; 4 monocrocophenyl, ethylene, ethylene, and methoxy groups; 4 monofluorophenyl, ethylene, ethylene, and methoxy groups 4-bromophenyl, ethylene, ethylene and methoxy; 4-phenyl, ethylene, ethylene and methoxy; phenyl, trimethylene, trimethylene and methoxy; 3,4-dichlorophenyl Nyl, ethylene, ethylene and methoxy; phenyl, tetramethyl Groups-ethylene group and hydroxy group; phenyl group, ethylene group, tetramethylene group and hydroxy group: 2-chloro phenyl group, ethylene group, ethylene group and hydroxy group; 3-cyclo phenyl group , Ethylene group, ethylene group and hydroxy group; 4 monofluorophenyl group, ethylene group, ethylene group and hydroxy group; 4-bromophenyl group, ethylene group, ethylene group and hydroxyl group; 4 monophenyl group, ethylene group, ethylene group 8. The composition for regulating plant growth according to claim 7, which is a phenyl group, a trimethylene group, a trimethylene group, or a hydroxyl group; or a 3,4-dichlorophenyl group, an ethylene group, an ethylene group, or a hydroxyl group. object.

12. The following general formula (1)

(In the formula, Ar represents a phenyl group which may have a substituent, A represents a linear or branched lower alkylene group, and B represents a linear or branched lower alkylene group or lower. Represents an alkenylene group, and R ′ represents a hydroxyl group, an amino group or a lower alcohol group) Or a salt thereof for producing a plant growth regulator.

 13.Ar force, a halogen atom, a hydroxyl group, a nitro group, a lower alkyl group and a lower alkoxyl group-a phenyl group which may be substituted with up to 5 groups, and A is a linear group 13. The use for producing a plant growth regulator according to claim 12, wherein the plant growth regulator is a lower alkylene group, and B is a linear lower alkylene group or a lower alkenylene group.

14. Ar is phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-hydroxydiphenyl, 4-fluorophenyl, 4-cyclophenyl, 4-bromophenyl A 4-phenylphenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group or a 3,4-dichlorophenyl group, A is a straight-chain alkylene group having 1 to 4 carbon atoms, and B is a C1-C4 alkylene group. A linear alkylene group or a linear alkylene group having 2 to 4 carbon atoms, wherein R ¹ is a hydroxyl group, an amino group, a methoxy group, an ethoxy group, an n-propoxy group or an i-propoxy group. 12. Use for producing a plant growth regulator according to item 2.

 15. Ar is a phenyl group, 4-methylphenyl group, 4-methoxyphenyl group, 4-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-phenylphenyl group, 2 —Chlorophenyl group, 3 —Chlorophenyl group or 3,4-dichlorophenol 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 13. The plant growth regulator according to claim 12, wherein the group is a straight-chain alkenylene group having 2 to 4 carbon atoms, and R i is a hydroxyl group, a methoxy group, an ethoxyquin group, an n-propoxy group, or an i-open mouth oxy group. Use for agent manufacture.

16. Ar, A, B and R ¹ forces, respectively, 4-methylphenyl, ethylene, ethylene and hydroxyl; 4-methoxyphenyl, ethylene, ethylene and hydroxyl; 4-chlorophenyl Phenyl, methylene, ethylene and hydroxyl; phenyl, trimethylene, ethylene and hydroxyl; phenyl, ethylene, methylene and hydroxyl A phenyl group, an ethylene group, a trimethylene A phenyl group, an ethylene group, a cis-vinylene group and a hydroxyl group; a phenyl group, an ethylene group, a trans-vinylene group and an ethoxy group; a phenyl group, an ethylene group, an ethylene group and a hydroxyl group; Phenyl group, ethylene group, ethylene group and methoxy group; phenyl group, trimethylene group, ethylene group and methoxy group; phenyl group, tetramethylene group, ethylene group and methoxy group; phenyl group, ethylene group, trimethylene group Phenyl, ethylene, ethylene and ethoxy groups; phenyl, ethylene, ethylene and n-propoxy groups; phenyl, ethylene, ethylene and n-propoxy groups; phenyl, ethylene, ethylene and n-propoxy groups; , Ethylene group, ethylene group and i-propoxy group; 2-chloro Phenyl group, ethylene group, ethylene group and methoxy group; 3-chlorophenyl group, ethylene group, ethylene group and methoxy group; 4 monochlorophenyl group, ethylene group, ethylene group and methoxy group 4 monofluorophenyl group, ethylene group, ethylene group and methoxy group; 4 monobromophenyl group, ethylene group, ethylene group and methoxy group; 4-hydrophenyl 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 hydroxy group; phenyl group, ethylene group , Tetramethylene and hydroxyl; 2-chlorophenyl, ethylene, ethylene 4-hydroxyphenyl group, ethylene group, ethylene group and hydroxy group; 4 monofluorophenyl group, ethylene group, ethylene group and hydroxy group; 4-bromophenyl group, ethylene group, Ethylene group and hydroxy group; 4 phenyl group, ethylene group, ethylene group and hydroxy group; phenyl group, trimethylene group, trimethylene group and hydroxy group; or 3,4-dichlorophenyl group, ethylene 13. The use for producing a plant growth regulator according to claim 12, wherein the group is an ethylene group or a hydroxyl group.