JPH03123706A - Plant growth-modulating agent - Google Patents

Abstract

PURPOSE:To provide the subject agent containing a mixture of a specified isonicotinic anilide-based compound and maleic hydrazide choline salt or (2- chroroethyl)trimethylammonium chloride and capable of dwarfing of lawn, rice, etc. CONSTITUTION:The subject agent composed of 5-45wt.% compound of the formula (R1 is H or lower alkyl; R2 is H or OH; X is halogen or lower alkyl; (n) is 0-2; Z is H or halogen), 1-25wt.% maleic hydrazide choline salt or (2- chloroethyl)trimethylammonium chloride, 0-15wt.% surfactant and 30-94wt.% carrier (e.g. talc or water). The above-mentioned agent has a prolonged applicable time and shows a synergism and no yield decrease is recognized, e.g. even when application as a loading-preventive agent for rice is carried out at any time before the heading time. The compounds of the formula are novel substances and obtained from an isonicotinic halide and an aniline derivative.

Description

Detailed Description of the Invention (In the formula, R1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R2 represents a hydrogen atom or a hydroxyl group, and X represents a halogen atom or a lower alkyl group having 1 to 2 carbon atoms. , n represents an integer from 0 to 2, and Z represents a hydrogen atom or a halogen atom.) and maleic acid hydrazide/cholic acid (hereinafter r
This invention relates to a plant growth regulator containing as an active ingredient a mixture of C-MHJ) or (2-chloroethyl)trimethylammonium chloride (hereinafter referred to as rCCCJ), particularly for effectively cyclizing grasses such as grasses and rice. The purpose is to provide a plant growth inhibitor with a wide range of applications and high practical value.

The isonicotinic acid anilide compound represented by the above general formula [I] is used as a plant growth inhibitor, for example, for rice, it is widely used in box raising, preventing elongation of seedlings, preventing aging, and preventing lodging of transplanted paddy fields. It can be used widely. Although it is effective against all types of grass, it exhibits a particularly strong growth-inhibiting effect on plants belonging to the Poaceae family.

Examples of effective plants include the above-mentioned rice, wheat, corn, and grass; however, broad-leaved plants also exhibit stable effects.

On the other hand, C-MH and CCC are substances known as plant growth regulators, and are already useful as lawn growth inhibitors, rice lodging prevention agents, and flower cyclization agents, but they are not very effective when used alone. Also, in high doses, the leaves of useful plants may turn brown, or the growth of new leaves may be delayed, resulting in unsightly appearance.

As a result of various studies for the purpose of supplementing these problems, the present inventors combined the isonicotinic acid anilide compound represented by the above general formula CI with the above-mentioned known growth regulator,
It has been found that when treated with plants, it does not harm useful plants at all and has an excellent growth regulating effect. That is, due to the additive effect, it exhibited a strong growth-inhibiting effect particularly on the grasses of the grass family, turf and rice, and in addition to extending the treatment period, unexpectedly, a synergistic effect was observed.

In other words, these compounds significantly increase the ability to suppress plant growth compared to when used alone, and exhibit a strong growth-inhibiting effect even on lawns where a thatch layer has been completed, thereby preventing lodging of rice. As an inhibitor, no decrease in yield was observed at any time of treatment before heading.

The present invention relates to a plant growth inhibitor and a lodging prevention agent, which are made by blending a plant growth regulator such as C-MH or CCC with an isonicotinic acid anilide compound as described above. It is characterized by significantly improved performance as a plant growth regulator due to its synergistic effect. Each of the above-mentioned plant growth regulators used in the mixture of the present invention is a known plant physiologically active substance as a plant growth regulator or herbicide. The development of synergistic effects of modulators is novel. The plant growth regulating effect of the mixed use of known plant growth regulators other than those mentioned above and the isonicotinic acid anilide compound used in the present invention was also investigated, and most of the combinations were found to be useful. However, the combination with the above drugs had the highest practical value.

The compound of the present invention represented by the general formula [I] is novel,
It can be manufactured by the method shown below.

(1) Isonicotinic acid halide represented by the general formula [II] (wherein Y represents a halogen atom) is dissolved in a suitable solvent. The compound represented by the general formula [I] is produced by reacting with the aniline derivative represented by (having the same meaning). In this case, the reaction will proceed more smoothly if a suitable deoxidizing agent is used.

Further, suitable solvents include pyridine, methanol, benzene, toluene, xylene, dichloromethane, and chloroform.

Examples include tetrahydrofuran, dioxane, acetone, and dimethylformamide. Pyridine, triethylamine, and hydric soda are used as deoxidizing agents.

Examples include potash, carbonated soda, and carbonated potash. Although the reaction proceeds at room temperature, it may be carried out with cooling or heating depending on the case. Preferably the temperature is 0 to 60°C. Although the reaction time depends on the selection of conditions, it is completed in 1 to 8 hours. After completion of the reaction, the desired product can be obtained by separating and purifying it by a conventional method.

(2) By reducing the isonicotinic acid derivative represented by the general formula [rV] (in which R1, Xl n and 2 have the same meanings as above) with a suitable reducing agent, the general formula [I ] A compound represented by the formula can be produced. Examples of the reducing agent include lithium aluminum hydride and sodium borohydride. In actual practice, it can be easily produced by using a conventional method for each reducing agent.

A manufacturing example will be given and explained below.

Production example 1゜N-methyl-inicotinic acid-(4-chloro-2-(α
-Hydroxybenzyl))anilide (compound number 3) 2-methylamino-5-chloropenthydrol 15 g
is dissolved in 30 ml of pyridine, the solution is cooled with ice while stirring, and 1.4 g of isonicotinic acid chloride hydrochloride is added in small portions. This takes about 30 minutes. 3 more
After stirring at room temperature for an hour, water 2001 was added to the reaction solution to precipitate crystals.

The crystals were collected and recrystallized from a mixed solvent of methanol and acetone, resulting in N-methyl-inicotinic acid-(4-chloro-
1.7 g of 2-(α-hydroxybenzyl))anilide are obtained. Melting point 199-201℃ Elemental analysis value: C20H1
7CρN202 (as molecular weight 351.81) CHN Calculated value (%) 88.08 4.8G 7
．． 94 Actual value (%) 67.96 4.98
7.79 The desired product was also obtained by replacing the solvent with pyridine and using benzene, toluene, xylene, dichloromethane, chloroform, tetrahydrofuran, dioxane, acetone, or dimethylformamide.

Production Example 2゜Isonicotinic acid-(4-ri00-2-(α-hydroxybenzyl))anilide (Compound No. 4) 1.9 g of isonicotinic acid-(4-chloro-2-benzoyl)anilide was added to methanol 201. Add 0.2 g of sodium borohydride little by little to the dissolved solution while stirring.

This will take approximately 30 minutes. Stirring was continued for an additional 2 hours at room temperature. After the reaction was completed, 200 ml of water was added to precipitate crystals. The crystals were collected by filtration and recrystallized from a dimethylformamide-methanol mixed solvent.
Chloro-2-(α-hydroxybenzyl)anilide 1.
8gwof1 elemental analysis value: C19H15cΩN202(
(as molecular weight 338.79) CHN Calculated value (%) 67.36 4.48 8.
27 Actual value (%) 87,18 4.5G
8.29 In addition, replacing the solvent with methanol and using pyridine,
Benzene, toluene, xylene, dichloromethane.

The desired product was obtained using chloroform, tetrahydrofuran, dioxane, acetone, and dimethylformamide.

Production example 3゜Isonicotine! -(4-Chloro-2-benzyl)anilide (Compound No. 1) 1.3 g of 4-chloro-2-benzylaniline was dissolved in pyridine 301, and this solution was cooled with ice, and while stirring, isonicotinic acid chloride hydrochloride Add 1.4g little by little. This takes about 30 minutes. After further stirring at room temperature for 3 hours, the reaction was completed. When water 2001 was added to this reaction solution, crystals were precipitated. The crystals are collected and recrystallized from ethanol to obtain isonicotinic acid-(4-chloro-2-benzyl)anilide L, Sg. Melting point: 178-73°C Elemental analysis value: Cl9H15CΩN20 (as molecular weight 322.79) CHN Calculated value (%) 70.70 4.68 8.
68 Actual value (%) 70,75 4.79
8.65 Next, representative examples of the compounds represented by the general formula [I] thus obtained are shown in Table 1. The present invention is not limited to these exemplified compounds. In addition,
The compound numbers are shown in the following examples and examples. Usually 100-3000g
1. It is appropriate to use preferably at a rate of 150 to 2000 g, but it goes without saying that the amount can be adjusted as appropriate depending on the cultivation conditions, growth status, and type of the plant. For example, when processing foliage, use 150 to 2 per lO are.
000 g is suitable, and a seedling raising box (30cm x fi
When processing 0 cm x 3 cm), use at a rate of 2 to 150 g per 10 are (20 boxes).

In addition, for formulation, it can be mixed with various solid and liquid carriers used in the preparation of general agricultural chemicals to produce wettable powders, emulsions, powders, granules, etc. Furthermore, auxiliary agents such as dispersants, diluents, emulsifiers, penetrants, and binders may be added to the drug. Further, depending on the purpose of use, the above constituent components can be used in combination with other herbicides, fungicides, insecticides, plant growth regulators, fertilizers, etc.

The carrier herein may be either solid or liquid. Examples of these include talc, clay carrion, diatomaceous earth, calcium carbonate, wood flour, and starch.

Gum arabic, water, alcohol, kerosene, naphtha, quidylol, xylene, cyclohexanone.

There are methylnaphthalene, benzene, acetone, etc., and nonionic agents (polyoxyethylene alkyl phenyl ether, ethylene oxide propylene oxide, copolymer, lignin sulfonate,
sorbitan esters, etc.), anionic (soaps, sulfated oils, alkyl sulfate ester salts, petroleum sulfonates, dioctyl sulfosuccinate salts, alkylaryl sulfonates, etc.), cationic (aliphatic amine salts, quaternary Examples include surfactants such as ammonium salts, alkylpyridinium salts, etc.) and amphoteric surfactants (alkylaminoethylglycine, alkyldimethylbetaine, polyglycol sulfate, alkylamine sulfonic acid, etc.).

However, it goes without saying that the embodiments of the present invention are not necessarily limited to the above-mentioned dosage forms.

In addition, in formulating the formulation, the mixing ratio is 5 to 45% of the compound represented by general formula [I]: 1 to 25% of the plant growth regulator.
: Surfactant: 0-15%: Carrier: 30-94% is optimal. Note that depending on the dosage form, it is not necessary to add a surfactant.

In addition, various insecticides and fungicides are used in the present invention.

Herbicides, plant growth regulators, acaricides, nematicides.

By using it in combination with attractants, repellents, plant nutrients, fertilizers, etc., a wider range of effects can be expected.

The season for using the chemical of the present invention may be, for example, the sowing stage, the seedling stage, or the growth stage (and depending on the target plant, treatments such as spraying on the ground, water surface or soil, and immersion can be performed).

Next, the effects of the present invention will be explained in detail with reference to experimental examples.

Experimental Example 1 A 115,000 are plastic pot was filled with sandy loam, sown with Kentara key bluegrass, grown using conventional methods for three years, and then cut to a height of 0.5 cm.
Using the formulation method shown in Example 1 below, the isonicotinic acid anilide compound, C-MH and CCC were prepared as a hydrating agent.
For single use, formulations were prepared in the same way, and the amount of clay was increased or decreased to maintain a constant concentration of 1 degree of active ingredient in the composition. ) was diluted with water and treated at a ratio of 1002/lea to give a predetermined dose.

Thereafter, they were kept in a glass greenhouse until the day of the survey. To investigate the effect, the height of the grass was measured 30 days after the chemical treatment, and at the same time, the grass was cut leaving 0.5 cm above ground, and its fresh weight was measured.

The results are shown in Table 2.

Experimental example 2゜The green of a golf course where bentgrass is cultivated (grown for 5 years) is divided into 182m x 2m, and the above-ground part is 0.5cm.
After harvesting to a height of 1, the isonicotinic acid anilide compound, C
-MH and CCC alone were formulated in the same way, and the amount of xylene was increased or decreased to keep the concentration of the active ingredient in the tissue constant.

) diluted with water to a predetermined amount and use a small feces container to make sure it adheres to the stems and leaves.1009. /
Sprayed at a rate of 10a. The effect was investigated at 3rd stage after drug treatment.
On day 0, the height of the grass and the fresh weight of the aboveground part (plant height 0°5c)
m) was measured.

Table 3 Continued Table 4 Rice short culm effect and lodging prevention effect Experimental example 3 Young rice seedlings (variety: Koshihikari) were mechanically transplanted in a paddy field using the conventional method (May 20, 1980), 42 days before heading.
The innicotinic acid anilide compound CCC was divided into 1 section 1O♂ and made into granules by the formulation method shown in Example 3 below.
A formulation for cars was prepared in the same way, and the concentration of the active ingredient in the composition was kept constant by increasing or decreasing bentonite. ) were sown in a predetermined amount.

Thereafter, the water depth was kept at 3 to 5 cm. The effect survey will be conducted on August 3rd.
The culm length was investigated on day 0, and the degree of lodging was investigated on October 10th.

The results are shown in Table 4.

Next, examples of the present invention will be shown, but the compounds, carriers, and proportions used are not limited to these examples.

Example 1 Compound Yin 4 40 parts by weight C-MH20
tt Sodium alkyl sulfate 5 Clay
35〃Mix these thoroughly until homogeneous and pulverize to obtain a wettable powder. When using this, dilute it with water to a predetermined concentration and spray.

Example 2 Compound Yin 1 20 parts by weight CCC5n Polyoxyethylene phenyl ether 7 Calcium alkylbenzenesulfone 3 Xylene
40 〃Cyclohexanone
25 Mix and dissolve these thoroughly until uniform to obtain an emulsion. When using this, dilute it with water to a predetermined concentration and spray.

Example 3 Compound Yin 5 10 parts by weight C-MH1
, 5 Bentonite 53 Diatom ± 35.5# These are mixed until homogeneous, pulverized and granulated by a conventional method, and used as granules.

Claims (1)

[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R1 represents a hydrogen atom or a lower alkyl group, R
2 represents a hydrogen atom or a hydroxyl group, X represents a halogen atom or a lower alkyl group, n represents an integer from 0 to 2, and Z represents a hydrogen atom or a halogen atom. 1. A plant growth regulator comprising, as an active ingredient, a mixture of one or more of the compounds represented by formula (1) and maleic acid hydrazide choline salt or (2-chloroethyl)trimethylammonium chloride.