JPH03128303A - Plant growth regulator - Google Patents

Abstract

PURPOSE:To provide the title regulator substantially improved in its performance due to the synergistic effect derived from the combination of specific isonicotinic anilide compound(s) and a specific plant growth regulator such as S-benzyl O,O-diisopropyl thiophosphate. CONSTITUTION:The objective plant growth regulator containing, as active ingredient, a mixture of (A) at least one compound of the formula (R1 is H or lower alkyl; R2 is B or OH; X is halogen or lower alkyl; (n) is 0, 1 or 2; Z is H or halogen) and (B) S-benzyl O,O-diisopropyl thiophosphate, 2,4- dichlorobenzyltributylphosphonium chloride or 2-chloroethyl phosphonic acid. The present regulator is entirely harmless to useful plants, having strong growth- inhibitory effects on the lawn and rice in true grasses, bringing no decrease in rice production when used as a rice falling-preventive agent at any time prior to ear emergence, and also having synergistic effect.

Description

Detailed Description of the Invention: represents a class alkyl group, R2 represents a hydrogen atom or a hydroxyl group, X represents a halogen atom or a lower alkyl group having 1 to 2 carbon atoms, n represents an integer from O to 2, Z represents a hydrogen atom or a halogen atom. ) 1 of the compound represented by
species or two or more species, and S-benzyl thiophosphate 0,0-
Diisopropyl (r I B PJ hereinafter), 2.4-
Dichlorobenzyl tributyl sulfonium chloride sulfon DJ) also relates to a plant growth regulator containing a mixture with 2-chloroethyl phosphonic acid (hereinafter referred to as ``Ethrel'') as an active ingredient, and is particularly effective for rice. The purpose is to effectively phosphorize family plants such as lawns and rice, and 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 [eco] is widely used as a plant growth inhibitor, for example, for rice, it is widely used for raising rice in boxes, preventing elongation of seedlings, preventing aging, and preventing lodging of transplanted paddy fields. It can be utilized. 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, IBP, phosphon D, and ethrel are known as plant growth regulators, and are already useful as lawn growth inhibitors, rice lodging prevention agents, and flower phosphatizing agents, but they are not effective when used alone. Decoys also have the disadvantage of turning leaves of useful plants brown, slowing the growth of new leaves, and impairing their aesthetic appearance when used in high doses.

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 [I] 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 comprising an isonicotinic acid anilide compound [Eco] combined with a plant growth regulator such as IBP, Phosphone D or Ethrel, as described above, and the present invention relates to a plant growth inhibitor and lodging prevention agent comprising an isonicotinic acid anilide compound [Eco] combined with a plant growth regulator such as IBP, Phosphone D or Ethrel. 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 agents 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 general formula [I] is novel,
It can be manufactured by the method shown below.

(1) Isonicotinic acid halide represented by the general formula [■]
21Xl n and Z have the same meanings as above. )
is reacted with an aniline derivative represented by the general formula [I
] is produced. In this case, the reaction will proceed more smoothly if a suitable deoxidizing agent is used. In addition, suitable solvents include helicin, methanol, benzene, and toluene.

Examples include xylene, dichloromethane, chloroform, tetrahydrofuran, dioxane, acetone, and dimethylformamide. Examples of deoxidizers include pyridine, triethylamine, sodium chloride, potassium chloride, soda carbonate, and potassium carbonate. Although the reaction proceeds at room temperature, it may be carried out with cooling or heating depending on the case.

Preferably it is 0 to 60°C. Although the reaction time depends on the selection of conditions, it is completed in 1 to 8 hours. After the reaction is completed, the desired product can be obtained by separation and purification using conventional methods.

(2) The isonicotinic acid derivative represented by the general formula [■C-0[■Co (in the formula, Rt+X+ n and Z have the same meanings as above)] can be easily reduced by reducing it with an appropriate reducing agent. A compound represented by the general formula [I] 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-isonicotinic acid-(4-chloro-2-(α
-Hydroxybenzyl))anilide (compound number 3) 2-methylamino-5-chlorobenzhydrol 15g
was dissolved in pyridine 30i+1, this solution was cooled with ice while stirring, and 1.4 g of isonicotinic acid chloride hydrochloride was added.
Add little by little. This takes about 30 minutes. After stirring for an additional 3 hours at room temperature, 200 ml of water was added to the reaction solution to precipitate crystals.

When the crystals were collected and recrystallized from a methanol-acetone mixed solvent, N-methyl-isonicotinic acid-(4-chloro-
2-(α-hydroxybenzyl))anilide 1.7g
get. Melting point 199-201℃ Elemental analysis value: C20H1
7C Father N202 (as molecular weight 351.81) CHN Calculated value m 68.08 4.8G 7.9
4 Actual measurement value (%) 87.9G 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-chloro-2-(α-hydroxybenzyl))anilide (Compound No. 4) Dissolve 1.9 g of isonicotinic acid-(4-chloro-2-benzoyl)anilide in 20 ml of methanol. Add 0.2 g of sodium borohydride little by little to the 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, 2 GG ml of water was added to precipitate crystals. The crystals were collected by filtration and recrystallized from a dimethylformamide-methanol mixed solvent.
10Rho 2-(α-hydroxybenzyl)anilide 1
．． Obtain 8g. Melting point: 210-212°C.

Elemental analysis value: Cl9HI5C received N202 (molecular weight 3
38.79) HN Calculated value (%) 87.38 4.4G 8
．． 27 Actual value (%) 87.18 4,58
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 Isonicotinic acid-<4-chloro-2-benzyl)anilide (compound number 1) 1.3g of 4-chloro-2-pencylaniline: Dissolved in 30ml of lysine and poured the solution on ice. Cool with stirring and
Add 1.4 g of isonicotinic acid chloride hydrochloride little by little. This takes about 30 minutes. After further stirring at room temperature for 3 hours, the reaction was completed. When 200 μl of water 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 IJg. Melting point! 78-179℃ Elemental analysis value: C19H15C father N20 (molecular weight 322
．． 79) CHN Total 'It (ti(%) 70.70 4J8
8.68 Actual value (%)? 0.75 4.7
9 8.85 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. The compound numbers are shown in the examples and actual examples below. Usually 100-3000g per are
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 grass leaves, it is per lOare! 50-2
000 g is appropriate, and a seedling box (30cm x 60
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 prepared into wettable powders, emulsions, powders, granules, etc. by combining it with various solid and liquid carriers used in the preparation of general agricultural chemicals. 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 betaine, 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 form.

In addition, in formulating the formulation, the mixing ratio is 5 to 45% of the compound represented by general formula CI: 1 to 25% of the plant growth regulator.
: Surfactant: 0-15%: Carrier: 30-34% 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 by showing experimental examples.

Experimental example 1.

1 Fill a 75,000 are plastic pot with sandy loam, sow Kentara Key bluegrass, grow it using a conventional method for 3 years, cut the lawn to a height of 0.5 cm, and then use the formulation method shown in Example 1 below. A similar formulation was prepared using only the isonicotinic acid anilide compound, Esrel, and Phosphone D without the use of a hydrating agent, and the concentration of the active ingredient in the composition was kept constant by increasing or decreasing the amount of clay. ) was diluted with water at a ratio of 100, Q/10a to give a predetermined dose and treated. 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.

Table 2 continued Experimental example 2゜The green of a golf course where bentgrass is cultivated (grown for 5 years) is divided into 1 section of 2m x 2m, and the above-ground part is 0.5cm.
After reaping to a height of 1, the emulsion was prepared using the formulation method shown in Example 2 below, and the isonicotinic acid anilide compound, Esrel and Phosphone D were formulated in the same manner, and the amount of xylene was increased or decreased. The concentration of the active ingredient in the tissue was kept constant. ) diluted with water to the specified amount,
10 minutes using a small poop container so that it fully adheres to the stems and leaves.
It was sprayed at a ratio of 0 (2/loa). The effectiveness was investigated by measuring the height of the grass and the fresh weight of the above-ground parts (cut to a height of 0.5 cm) on day 30 after the chemical treatment.

The results are shown in Table 3.

Experimental Example 3 Young rice seedlings (variety: Koshihikari) were mechanically transplanted in a paddy field using a conventional method (May 20, 1980), 42 days before heading.
Divided into 1 section ioI/, the formulation method shown in Example 3 below was used to formulate the isonicotinic acid anilide compound and IBP alone without making granules, and by increasing or decreasing bentonite, the formulation was made in the same way. The active ingredient concentration was kept constant. ) was sown in a predetermined quantity. After that, increase the water depth to 3 to 5 cm.
I kept it. The effect was investigated on August 30th by measuring the culm length and l
The degree of lodging was investigated on 0810th.

Table 4 Short culm effect and lodging prevention effect in rice Next, examples of the present invention are shown, but the compounds, carriers and usage ratios are not limited to these examples.

Example 1 Compound Na4 40 parts by weight IBP
20//alkyl sodium 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 temperature of 76 degrees and spray.

Example 2 Compound Yin 1 20 parts by weight Phosphone [
) 5 tt polyoxyethylene phenyl ether 7 Calcium alkylbenzene sulfonate 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 N115 10 parts by weight Ethrel 1.5 Bentonite 53 Diatomaceous earth
35.5//These are mixed until homogeneous, pulverized, and granulated by a conventional method to be 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. ) and S-benzyl 0,0-diisopropyl thiophosphate, 2,4-dichlorobenzyltributylphosphonium chloride or 2
- A plant growth regulator characterized by containing a mixture with chloroethylphosphonic acid as an active ingredient.