JPH0353281B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [] (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, X represents a halogen atom or a lower alkyl group having 1 to 2 carbon atoms, and n is 0 to represents an integer of 2, and Z represents a hydrogen atom or a halogen atom.)
and one or more of the compounds represented by S-benzyl 0,0-diisopropyl thiophosphate (hereinafter referred to as "IBP"), 2,4-dichlorobenzyltributylsulfosulfonium chloride (hereinafter referred to as "Phosphone D") Or, it relates to a plant growth regulator containing as an active ingredient a mixture with 2-chloroethylphosphonic acid (hereinafter referred to as "Ethrel"), and is particularly intended to effectively dwarf grasses, grasses, etc. It is said that
The present invention provides a plant growth inhibitor with a wide range of applications and high practical value. The isonicotinic acid anilide-based processed product represented by the above general formula [] is used as a plant growth inhibitor.
For example, for rice, it can be widely used for raising seedlings in boxes, preventing the growth of seedlings, preventing aging, and preventing lodging of transplanted paddy fields. 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 rice mentioned above, as well as wheat, corn, and grass.
It also exhibits stable effects on broad-leaved plants. On the other hand, IBP, Huon Huon D, and Ethrel are known plant growth regulators, and are already useful as lawn growth inhibitors, rice lodging prevention agents, and flower dwarfing 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 a loss of aesthetic appearance. As a result of various studies to address these problems, the present inventors have found that the isonicotinic acid anilide compound represented by the above general formula [] and the above-mentioned known growth regulator are combined and treated with plants. It was discovered that this method does not cause any harm to useful plants 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 have a significantly greater ability to inhibit plant growth than when used alone, exhibiting a strong growth-inhibiting effect even on lawns with a complete saturation layer, and inhibiting rice lodging. 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 an isonicotinic acid anilide compound [ ] with a plant growth regulator such as IBP, Fosphone D or Esrel, as described above. It is characterized by significantly improved performance as a plant growth regulator due to its synergistic effects. 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 was of high practical value. The compound of the present invention represented by the general formula [ ] is novel and can be produced by the method shown below. (1) General formula [] (In the formula, Y represents a halogen atom.) Isonicotinic acid halide represented by the general formula [] (In the formula, R1, R2, X, n and Z have the same meanings as above.) A compound represented by the general formula [] is produced by reacting with an aniline derivative represented by the formula []. In this case, the reaction will proceed more smoothly if a suitable deoxidizing agent is used. Suitable solvents include pyridine, methanol, benzene, toluene, xylene, dichloromethane, chloroform, tetrahydrofuran, dioxane, acetone, dimethylformamide, and the like. As a deoxidizing agent, pyridine, triethylamine, caustic soda, caustic potash, soda carbonate,
Examples include potassium carbonate. The reaction may proceed at room temperature, but may be carried out with cooling or heating as the case may be. The temperature is preferably 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) General formula [] The compound represented by the general formula [] is easily produced by reducing the isonicotinic acid derivative represented by the formula (in which R1, X, n and Z have the same meanings as above) with an appropriate reducing agent. be able to. 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 No. 3) Dissolve 15 g of 2-methylamino-5-chlorobenzhydrol in pyridine ml, cool the solution with ice while stirring, and dissolve isonicotinic acid chloride hydrochloride. Add 1.4g of salt 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 these crystals were collected and recrystallized from a methanol-acetone mixed solvent, N-methyl-isonicotinic acid-{4-chloro-2-(α-hydroxybenzyl)}anilide was obtained.
Obtain 1.7g. Melting point 199-201℃ Elemental analysis value: C20H17ClN2O2 (molecular weight 351.81) C H N Calculated value (%) 68.08 4.86 7.94 Actual value (%) 67.96 4.98 7.79 In addition, by changing the solvent to pyridine, benzene, toluene, xylene, dichloromethane, The desired product was also obtained using chloroform, tetrahydrofuran, dioxane, acetone, and dimethylformamide. Production Example 2 Isonicotinic acid-{4-chloro-2-(α-hydroxybenzyl)}anilide (Compound No. 4) A solution of 1.9 g of isonicotinic acid-(4-chloro-2-benzoyl)anilide dissolved in 20 ml of methanol. Add 0.2 g of sodium borohydride little by little 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 to give isonicotinic acid-{4-chloro-2-(α
-hydroxybenzyl)}anilide 1.8 g is obtained.
Melting point 210-212℃. Elemental analysis value: C19H15ClN2O2 (as molecular weight 338.79) C H N Calculated value (%) 67.36 4.46 8.27 Actual value (%) 67.18 4.56 8.29 In addition, the solvent was changed to methanol and 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 No. 1) Dissolve 1.3 g of 4-chloro-2-benzylaniline in 30 ml of pyridine, cool the solution with ice, and add 1.4 g of isonicotinyl chloride hydrochloride little by little while stirring. This will take 30 minutes. Further at room temperature 3
Continue stirring for an hour to complete the reaction. When 200 ml of water was added to this reaction solution, crystals were precipitated. The crystals were collected and recrystallized from ethanol to obtain 1.6 g of isonicotinic acid-(4-chloro-2-benzyl)anilide. Melting point 178-179℃ Elemental analysis value: C19H15ClN2O (molecular weight 322.79) C H N Calculated value (%) 70.70 4.68 8.68 Actual value (%) 70.75 4.79 8.65 Next, it is expressed by the general formula [] obtained in this way. Table 1 shows representative examples of the compounds that can be used. The present invention is not limited only to these exemplified compounds. Note that the compound numbers are also referred to in the following Examples and Experimental Examples.

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[Table] The plant growth regulator of the present invention has the general formula []
A mixture of one or more of the compounds represented by the above and each of the above plant growth regulators is usually added per 10 ares.
It is appropriate to use it at a rate of 100 to 3000 g, preferably 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, 10
150 to 2000 g per are is appropriate, and when processing into seedling boxes (30 cm 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 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. Also,
Depending on the purpose of use, the above 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, starch,
Gum arabic, water, alcohol, kerosene, naphtha, xylol, xylene, cyclohexanone,
These include methylnaphthalene, benzene, acetone, etc., and nonionic agents (polyoxyethylene alkyl phenyl ether, ethylene oxide propylene, oxide copolymers, lignin sulfonates, sorbitan esters, etc.), anionic types (soaps, sulfated oils, alkyl sulfate ester salts, petroleum sulfonates, dioctyl sulfosuccinate salts, alkylaryl sulfonates, etc.), Cationic (aliphatic amine salts, quaternary 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 form. In addition, when formulating, the mixing ratio is determined by the general formula []
5-45% of the compound represented by: 1-25% of the plant growth regulator: 0-15% of the surfactant: 30-94% of the carrier
is optimal. Note that depending on the dosage form, it is not necessary to add a surfactant. In addition, in the present invention, various insecticides, fungicides,
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 chemical of the present invention may be used during, for example, the sowing period, the seedling period, or the growing period, 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 A 1/5000 are plastic pot was filled with sandy loam soil, Kentucky bluegrass was sown, and the grass was cultivated using a conventional method for 3 years. After mowing the grass to a height of 0.5 cm, the formulation shown in Example 1 below was prepared. (Isonicotine acid anilide compounds, Sless, and Fosfone D alone were formulated in the same way, and the concentration of the active ingredient in the composition was kept constant by increasing or decreasing the amount of clay.) The solution was diluted with water at a rate of 100 liters/10 a to give the prescribed amount. From then on, the grass was kept in a glass greenhouse until the day of the survey.30 days after chemical treatment, the height of the grass was measured, and at the same time, the grass was cut leaving 0.5cm above ground.
The live weight was measured. The results are shown in Table 2.

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[Table] Experimental Example 2 The green of a golf course where bentgrass was cultivated (grown for 5 years) was divided into sections of 2m x 2m, and the above-ground part was cut to a height of 0.5cm.
Emulsions and non-emulsions (isonicotinic acid anilide compounds, Esrel, and Phosphone D alone) were formulated in the same manner using the formulation method shown in Figure 2, and the concentration of the active ingredient in the tissue was kept constant by increasing or decreasing the amount of xylene. )
Dilute the material with water to the specified amount and use a small feces container to make sure it adheres to the stems and leaves.
Sprayed at a rate of 100l/10a. To investigate the effectiveness, 30 days after chemical treatment, the height of the grass and the fresh weight of the above-ground part (plants cut to a height of 0.5 cm) were measured. The results are shown in Table 3.

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[Table] Experimental example 3 Young rice seedlings (variety: Koshihikari) were mechanically transplanted in a paddy field using the conventional method (May 20, 1980), and the ears appeared at 42
1 day in advance, divided into 10 cm ² sections, and prepared into granules using the formulation method shown in Example 3 below (Isonicotinic acid anilide compounds and IBP alone were formulated in the same way, and the composition was made by increasing or decreasing bentonite. The concentration of active ingredients in the mixture was kept constant. After that, the water depth was kept at 3 to 5 cm. To investigate the effects, culm length was investigated on August 30th, and the degree of lodging was investigated on October 10th. The results are shown in Table 4.

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[Table] Examples of the present invention are shown below, but the compounds, carriers, and proportions used are not limited to these examples. Example 1 Compound No. 4 40 parts by weight IBP 20 Sodium alkyl sulfate 5 Clay 35 These are thoroughly mixed until homogeneous and pulverized to obtain a wettable powder. When used, this is diluted to a predetermined concentration and sprayed. Example 2 Compound No. 1 20 parts by weight Phosphone D 5 Polyoxyethylene phenyl ether 7 Calcium alkylbenzenesulfonate
3. xylene 40. cyclohexanone 25. Mix and dissolve these ingredients thoroughly until uniform to obtain an emulsion. When using this, dilute it with water to a predetermined concentration and spray. Example 3 Compound No. 5 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] 1. General formula (In the formula, R1 represents a hydrogen atom or a lower alkyl group, R2 represents a hydrogen atom or a hydroxyl group, X represents a halogen atom or a lower alkyl group, and n is 0
represents an integer from 2 to 2, and Z represents a hydrogen atom or a halogen atom. ) and S-benzyl thiophosphate 0,0-
Diisopropyl, 2,4-dichlorobenzyltributylphosphonium chloride or 2-
A plant growth regulator characterized by containing a mixture with chloroethyl phosphor acid as an active ingredient.