JPS62240603A - Plant growth promoting agent and process therefor - Google Patents

Abstract

PURPOSE:To promote the growth of a plant, by using a relatively easily available inexpensive N-phenylglycylphenylglycine compound as an active component of a plant-growth promoter and applying the promoter to a plant or its living environment. CONSTITUTION:A compound of formula I [R<1> is -OR<11> (R<11> is H or alkyl) or group of formula II (R<12> and R<13> are H, alkyl or together with N form a heterocyclic group); R<2> and R<3> are H, alkyl or acyl; R<4> is H, halogen, OH, alkyl or alkoxy], its salt or acid addition salt is used as an active component of a plant-growth promoter and is applied to the whole plant, its leaf, root, stalk, seed, etc., or a field growing the plant at a rate of 0.1-500g (preferably 1-200g) per 10 are of the field. In the case of applying to seed or callus (for tissue culture), it is used as a solution having an active component concentration of 10ppm-1%.

Description

DETAILED DESCRIPTION OF THE INVENTION a. Field of Industrial Application The present invention relates to a plant growth promoter and a method for promoting plant growth. More specifically, the present invention relates to a plant growth promoter and a method for promoting plant growth using N-phenylglycylphenylglycine as an active ingredient for plant growth.

b. Prior Art Various active compounds have been proposed for the purpose of promoting growth, increasing yield, and enlarging fruits of ornamental plants and cultivated plants.
An example of this is plant hormones isolated from natural products. However, when such plant pornes are isolated from natural products, it is extremely difficult to obtain them in large quantities, and their synthesis is extremely expensive.

On the other hand, many proposals have been made to promote plant growth using artificially synthesized compounds, and among these, certain aminocarboxylic acids or derivatives thereof have a stimulating or promoting effect on plant growth. It has been known.

German Patent Publication No. 2217896 describes that L-methionine, DL-methionine, and their esters or salts are effective in enlarging fruits, increasing yield, increasing sugar content ω, and the like.

In addition, Japanese Patent Publication No. 49-3344 discloses that aliphatic carboxylic acids such as α-hydroxy-α-hexylmalonic acid represented by the following formula %, or their salts, esters, or amides are useful for plant growth or metabolism, especially for plant growth or metabolism. It has been described to have activities that affect water balance.

In addition, Japanese Patent Publication No. 46-23020 @ Publication states that DL-tryptophan is used for the growth of laver species that grow in seawater.

L-Leucine, Cystine, Aspartic acid, L
The application of -phenylalanine, -tyrosine or their salts is described.

C0 OBJECTS OF THE INVENTION Therefore, it is an object of the present invention to provide a novel plant growth promoter.

Another object of the present invention is to provide a plant growth promoter containing N-phenylglycylphenylglycines, which are relatively easily available and inexpensive compounds, as an active ingredient.

A further object of the present invention is to provide a plant growth promoter with excellent growth promoting effects and yield increasing effects.

Still another object of the present invention is to provide a plant growth promoter that is relatively versatile for various plants.

Still another object of the present invention relates to a method of promoting plant growth by applying the plant growth promoter of the present invention to living plants or their living environments.

Further objects and advantages of the present invention will become apparent from the description below.

d0 Structure and Effects of the Invention According to the present invention, the objects and advantages of the present invention are as follows: Alternatively, when R2 or R3 is a group other than an acyl group, this can be achieved by a plant growth promoter containing an acid addition salt of an amino group as an active ingredient for promoting plant growth.

In the above formula (I>), R1 is -Q Rll or R+2 alkyl group, and R12 and R11 are each independently a hydrogen atom or an alkyl group having 5 or less carbon atoms, or R
12 and lli may be bonded to each other and together with the nitrogen atom to which they are bonded, form a 5- or 6-membered heterocycle which may optionally contain a heteroatom.

The alkyl group having 5 or less carbon atoms in Rll may be linear or branched, such as methyl, ethyl, n-
Propyl, 1so-propyl, n-butyl, 5ec
-butyl, 1so-butyl, t-butyl.

n-pentyl and the like.

As the alkyl group having 5 or less carbon atoms in RI2 and Rll, the same group as the above example for l(I+ can be exemplified).

The 5- or 6-membered heterocycle formed by the bond R+2 and Rll can, for example, further contain a nitrogen atom, an oxygen atom or a sulfur atom as a heteroatom.

As the group -ORll, mention may be made, according to the definition of 1 (TI), for example groups such as hydroxyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy or n-pentoxy.

I2 Rll Monoalkylamines such as amino, methylamino, ethylamino, n-propylamine, 1so-propylamine, n-butylamino, 1so-butylamino, n-pentylamino; dimethylamine, diethylamine, monoalkylamine Such dialkylamines, piperidino, piperazino.

Groups such as morpholino and pyridyl can be mentioned.

In the above formula (I), R2 and R3 are each independently a hydrogen atom, an alkyl group having 5 or less carbon atoms, or an acyl group having 5 or less carbon atoms. Examples of the alkyl group having 5 or less carbon atoms include the same ones as exemplified for R1+. Examples of the acyl group having 5 or less carbon atoms include formyl, acetyl, propionyl, butyryl, iso-butyryl, valeryl, iso-valeryl, and the like.

Moreover, R4 is a hydrogen atom, a halogen atom, or a hydroxyl group.

It is an alkyl group having 5 or less carbon atoms or an alkoxy group having 5 or less carbon atoms. An example of a halogen atom is fluorine.

These are chlorine, bromine, and iodine. As the alkyl group having 5 or less carbon atoms, the same ones as those exemplified for II+ can be mentioned, and as the alkoxy group having 5 or less carbon atoms, the same ones as exemplified for -QR1+ can be mentioned.

When the N-phenylglycylphenylglycine represented by the above formula (I>) has a carboxyl group (formula (I)
>, when R1 is a hydroxyl group), the carboxyl group can be in the form of a salt. Such salts include, for example, sodium.

Salts of alkali metals such as potassium, calcium.

Examples include salts of alkaline earth metals such as magnesium, ammonium salts, and the like.

In addition, when the N-phenylglycylphenylglycine represented by the above formula (I>) is an amino group t<J, that is, a hydrogen atom or an alkyl group having 5 or less carbon atoms, the amino group is an acid addition salt thereof. Such acid addition salts include, for example, hydrochloride, mineral acid salts such as hydrogen bromide r1i salt, and lower aliphatic carboxylic acid salts such as acetate.

As the N-phenylglycylphenylglycines represented by the above formula (I>), compounds in which R2 is, for example, a hydrogen atom or an alkyl group having 5 or less carbon atoms are preferred.

Examples of such N-phenylglycylphenylglycines, salts thereof, or acid addition salts thereof include the following compounds.

(1) N-phenylglycylphenylglycine (2) N
-(4-hydroxyphenylglycyl) phenylglycine (3) N-(4-methoxyphenylglycyl) phenylglycine (4) N-(4-chlorophenylglycyl) phenylglycine (5) N-(4-methylphenyl glycyl) phenylglycine (6) N-(4-chlorophenylglycyl)-4-chlorophenylglycine (7) N-7enylglycylphenylglycine methyl ester (8) N-(4-hydroxyphenylglycyl) phenyl Glycine methyl ester (9) N-(4-methoxyphenylglycyl) phenylglycine methyl ester (10) N-(4-chlorophenylglycyl) phenylglycine methyl ester (11) N-(4-methylphenylglycyl) phenyl Glycine methyl ester (12) N-(4-chlorophenylglycyl)-4-chlorophenylglycine methyl ester (13) N-(N
-acetylphenylglycyl)phenylglycine (14)N -(N-acetylphenylglycyl)-4
-chlorophenylglycine (15)N ''-(N niacetylphenylglycyl-
Methylphenylglycine (1B) N-(N-acetyl-4-chlorophenylglycyl)-4-chlorophenylglycine (17) N-(N
-acetylphenylglycyl)phenylglycine methyl ester (18)N-(N-acedelphenylglycyl)-4=
Chlorophenylglycine medyl ester (19) N-(
N-acedelphenylglycyl) phenylglycine amide (20) N-(N-acetylphenylglycyl) phenylglycine sodium salt The plant growth promoter of the present invention comprises N-phenylglycylphenylglycine of the above formula (I>) , a salt thereof, or an acid addition salt thereof as an active ingredient for promoting plant growth.

The plant growth promoter of the present invention is usually used in a form combined with an inert carrier or adjuvant.

Such inert carriers or adjuvants include, for example, talc, bentonite, clay, phosphorus, diatomaceous earth.

Why carbon, vermiculite, slaked lime.

Solid carriers such as ammonium sulfate, urea, etc.; water, alcohol, dioquinane, acetone, xylene, cyclohexane.

Liquid carriers such as medylnaphthalene and dimethylformamide; alkyl sulfates, alkyl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene sorbitan monoalkylate, dinaphthyl methane Examples include surfactants such as disulfonate salts, emulsifiers or dispersants, and various auxiliary agents such as carboxymethylcellulose and gum arabic.

These inert carriers and adjuvants can be used alone or in combination of two or more.

The plant growth promoter of the present invention can be prepared by mixing the above-mentioned active ingredient with the above-mentioned inert carrier and/or adjuvant, for example, in a solution,
The preparations are prepared in conventional forms such as emulsions, suspensions, powders, pastes, or granules.

The plant growth promoter of the present invention, in the form of a preparation as described above, usually contains the active ingredient in an amount of 0.01 to 99% by weight, more preferably 0.1 to 96% by weight.

The plant growth promoter of the present invention promotes plant growth by applying it to living plants or their living environments in an effective manner to promote plant growth.

The application to living plants can be the whole or part of the living plant, such as leaves, roots,
It can be a stem, a bud, or a callus in tissue cultured plants.

The plant growth promoter of the present invention preferably contains the active compound in an amount of 0.1 to 500 (J
, more preferably 1 to 200 (1 part M).

Application can be carried out by conventional methods such as, for example, spraying, spraying, dusting.

When applied to seed Jakarus, 1 Dt) m to 10%
, more preferably as a solution with an active ingredient concentration of io ppm to 1%.

The plant growth promoter of the present invention has the activity of promoting the growth of various plants. For example, rice, wheat as useful plants,
In addition to major grains such as corn and soybeans, there are also cotton, sugarcane, millet, millet, radish, turnip, mizuna, Chinese cabbage, and cabbage.

When applied to broad-leaved crops such as spinach, lettuce, salad greens, and watercress, it exhibits an extremely significant growth promoting effect.

The present invention will be explained in further detail with reference to Examples below.

Example 1 Synthesis of N-(N-7cetylphenylglycyl)phenylglycine methyl ester; 0.96 parts by weight of N-acetylphenylglycine was added to 20 parts by weight of chloroform, and dicyclohexylcarbodiimide 1.0% was added under water cooling. Add 03 parts by weight and stir.

Phenylglycine methyl ester 0.83 deuterium was added to the colander, and after about 3 hours, the mixture was returned to room temperature and stirred overnight. After the reaction, the washed product was filtered and washed with chloroform. The furnace liquid was concentrated to dryness, the obtained solid was washed with ethyl acetate,
A portion soluble in a chloroform-petroleum ether mixed solvent was extracted from the solid remaining in the colander to obtain the above compound 1.2 heavy base. The melting points m and p of the compound were 198 to 200°C.

Examples 2 to 5 Five plants each of mizuna, Japanese radish, soybean, and Japanese radish were sown in vinyl pots with an area of 100 cm2, and 14 days after sowing (DAS), compound 17 (compound NO. (Means the same as No. of the compound shown in the specification) was treated with a hydrating agent using a hydrating agent. Also,
The "hydrating agent" consists of 1 part by weight of N-7 glycylphenylglycine derivative, 8.7 ffl of a mixture of equal amounts of talc and Pen 1 to Nai 1, and SOLPOR.
13 parts by weight of an equal suspension mixture O of SQLFOR 5060 (manufactured by Toho Chemical Industry Co., Ltd.) and SQLFOR 8008 (manufactured by Toho Chemical Industry Co., Ltd.) were thoroughly ground and mixed to prepare a wettable powder. The crop was grown as a control without treatment with active substance. After the above-mentioned foliage treatment (DAT > 20 days), cut the foliage part of the crop and compare its total fresh weight with the control example.
The promoting effect was measured by determining the weight ratio. The results are shown in Table 1 below.

Claims (1)

[Claims] 1. The following formula (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼... (I) [Here, R^1 is -OR^1^1 or ▲ Numerical formulas, chemical formulas, tables, etc. etc. ▼, where R^1^1 is a hydrogen atom or an alkyl group having 5 or less carbon atoms, and R^1^2 and R
^1^3 are each independently a hydrogen atom or an alkyl group having 5 or less carbon atoms, or R^1^2 and R^1^3 are bonded to each other and together with the nitrogen atom to which they are bonded. It may also form a 5- or 6-membered heterocycle which may further contain a heteroatom, and R^2 and R^3 each independently represent a hydrogen atom, an alkyl group having 5 or less carbon atoms, or a C5 or less alkyl group. It is an acyl group having 5 or less carbon atoms, and R^4 is a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group having 5 or less carbon atoms, or an alkoxy group having 5 or less carbon atoms. ] N-phenylglycylphenylglycines represented by, its salt in a carboxyl group when R^1 is a hydroxyl group, or its salt in an amino group when R^2 or R^3 is a group other than an acyl group A plant growth promoter containing an acid addition salt as an active ingredient for promoting plant growth. 2. In the above formula (I), the definition of R^1 is the same as above, R^2 is a hydrogen atom or an alkyl group having 5 or less carbon atoms, and the definitions of R^3 and R^4 are as above. The plant growth promoter according to item 1, which is the same as . 3. The following formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) [Here, R^1 is -OR^1^1 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ , R^1^1 is a hydrogen atom or an alkyl group having 5 or less carbon atoms, and R^1^2 and R
^1^3 are each independently a hydrogen atom or an alkyl group having 5 or less carbon atoms, or R^1^2 and R^1^3 are bonded to each other and together with the nitrogen atom to which they are bonded. Furthermore, it may form a 5- or 6-membered heterocycle which may further contain a Tehero atom, and R^2 and R^3 each independently represent a hydrogen atom, an alkyl group having 5 or less carbon atoms, or a C5 or less alkyl group. It is an acyl group having 5 or less carbon atoms, and R^4 is a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group having 5 or less carbon atoms, or an alkoxy group having 5 or less carbon atoms. ] N-phenylglycylphenylglycines represented by, its salt in a carboxyl group when R^1 is a hydroxyl group, or its salt in an amino group when R^2 or R^3 is a group other than an acyl group A method for promoting plant growth, which comprises applying an acid addition salt to living plants or their living environment in an amount effective for promoting plant growth. 4. The method according to item 3, wherein the amount effective for promoting plant growth is 0.1 to 500 g per 10 ares of area where plants live.