JPS6341393B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [] (In the formula, R ₁ 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 methyl group, n represents an integer from 0 to 2, and Z represents a hydrogen atom or The present invention relates to an isonicotinic acid anilide derivative represented by (representing a halogen atom), a method for producing the same, and a plant growth regulator comprising one or more of the compounds. Furthermore, the compound of the present invention is effective against all kinds of plants, but shows particularly excellent effects against grasses. In recent years, a major change in rice cultivation has been the remarkable progress in mechanization of rice planting and harvesting. Therefore, in recent rice cultivation techniques, the development of cultivation techniques that can develop healthy seedlings suitable for mechanized transplantation and prevent lodging during harvest have become particularly important issues. In other words, Koshihikari, Sasanishiki, etc., which are said to be branded rice, have extremely high reputations for taste, but on the other hand, they are extremely susceptible to lodging and have the disadvantage of being susceptible to diseases. For these reasons, it is desired to establish a cultivation technique that can raise healthy rice seedlings and to have high mechanical adaptability during harvesting, or to develop a growth control method using drugs. The present inventors have repeatedly investigated compounds that have a growth regulating effect on various plants, mainly rice, for several years. As a result, the isonicotinic acid anilide derivative represented by the above general formula [] has been found to be effective against grasses. The present invention was completed based on the discovery that this substance exhibits an epoch-making growth regulating effect. The compound represented by the general formula [] can be widely used for rice, for example, to prevent elongation in seedling boxes and seedling beds, to prevent aging, to prevent lodging in transplanted paddy fields, and to increase yield. Furthermore, it can have the same effect on wheat, corn, sugarcane, etc. as it does on rice. It is also effective in preventing elongation of hypocotyls of eggplants, cucumber seedlings, etc. On the other hand, application to lawns is also one of the most effective methods of use.
It is one. In other words, in recent years, grass has been widely used in homes, gardens, golf courses, green areas, roadsides, green belts, etc., but not only is it troublesome to manage, but it also grows rapidly in the summer, making it difficult to cut it. It requires a lot of effort and also requires a huge amount of expense. In addition to grass, many grasses are used on general roads, highway shoulders, green belts, and slopes of highways and railways, and their management requires a great deal of effort and expense. Not only that, but maintenance work involves great danger. Therefore, the application of the compound according to the present invention to such situations is of great significance. Further, the compound represented by the general formula [] can be used for both grasses and broad-leaved plants as described above, and can be expected to increase resistance to poor environments and pests. In addition, the promotion of photosynthesis by increasing chlorophyll,
It has a wide range of effects, including promoting carbohydrate production and root growth. The major characteristics of the compound of the present invention are that it strongly suppresses plant growth, especially plant height growth, darkens the leaf color, and , dead leaves,
It is possible to grow healthy without causing any chemical damage such as dead plants. 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, R ₁ , R ₂ , 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 following. In this case, the reaction will proceed more smoothly if a suitable deoxidizing agent is used. Further, suitable solvents include benzene, toluene, xylene, dichloromethane, chloroform, tetrahydrofuran, dioxane, dimethylformamide, and the like. Examples of deoxidizers include pyridine, triethylamine, caustic soda, caustic potash, soda carbonate, and 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 [] (In the formula, R ₁ , X, n and Z have the same meanings as above.) By reducing the isonicotinic acid derivative represented by the formula with an appropriate reducing agent, the general formula []
A compound represented by 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 No. 3) Dissolve 1.5 g of 2-methylamino-5-chlorobenzhydrol in 30 ml of pyridine, cool the solution with ice while stirring, and dissolve isonicotinic acid chloride. Add 1.4 g of hydrochloride 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 1.7 g is obtained. Melting point 199-201℃ Elemental analysis value: C ₂₀ H ₁₇ ClN ₂ O ₂ (as molecular weight 351.81) C H N Calculated value (%) 68.08 4.86 7.94 Actual value (%) 67.96 4.98 7.79 Production example 2 Isonicotinic acid-{4 -Chloro-2-(α-hydroxybenzyl)}anilide (Compound No. 4) Add 0.2 g of sodium borohydride to a solution of 1.9 g of isonicotinic acid (4-chloro-2-benzoyl) anilide in 20 ml of methanol with stirring. Add little by little. 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. This crystal was collected and recrystallized from a dimethylformamide-methanol mixed solvent to give isonicotinic acid {4-chloro-2-(α
-Hydroxybenzyl)anilide 1.8 g are obtained.
Melting point 210-212℃ Elemental analysis value: C ₁₉ H ₁₅ ClN ₂ O ₂ (as molecular weight 338.79) C H N Calculated value (%) 67.36 4.46 8.27 Actual value (%) 67.18 4.56 8.29 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 isonicotinic acid chloride hydrochloride little by little while stirring. This will take approximately 30 minutes. Stirring was further continued at room temperature for 3 hours to complete the reaction. When 200 ml of water was added to this reaction solution, crystals were precipitated. When these crystals were collected and recrystallized with ethanol, 1.6 g of isonicotinic acid (4-chloro-2-benzyl)anilide was obtained.
get. Melting point 178-179°C Elemental analysis value: C ₃₉ H ₁₅ ClN ₂ O (as molecular weight 322.79) C H N Calculated value (%) 70.70 4.68 8.68 Actual value (%) 70.75 4.79 8.65 Next, the thus obtained Representative examples of compounds represented by the general formula [] are shown in Table 1. 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.

【table】

【table】

【table】

[Table] The plant growth regulator of the present invention contains one or a mixture of two or more compounds represented by the general formula [].
It is usually appropriate to use the drug at a rate of 50 to 1000 g per 10 ares, but it goes without saying that the amount can be adjusted as appropriate depending on the use situation, purpose of use, and plant condition. In addition, for formulation, it can be mixed with various solid and liquid carriers used in the formulation 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. Next, the effects of the present invention will be explained in detail by showing experimental examples. Experimental example 1 Growth inhibition test by pre-germination soil treatment on various plants A pot of 1/5000 are was filled with clay loam,
After sowing bentgrass, Kentucky bluegrass, cucumber, mung bean, komatsuna, cyperus, crabgrass, rice, and corn, the soil was shallowly covered with soil, and a hydrating agent of the test compound prepared according to the formulation in Example 1 was added to the soil. It was diluted with water and sprayed with a small sprayer at a predetermined amount of active ingredient, 250g or 500g per 10 ares. In the survey, plant height was measured 50 days after spraying. The results are shown in Table 2. The effect values shown in Table 2 represent the following levels of plant growth inhibitory activity. 0: Growth inhibition rate of 0-10% compared to untreated area 1: 11-20% 2: 21-30% 3: 31-40% 4: 41-50% 5: 51% or more

【table】

[Table] Experimental Example 2 Growth inhibition test by foliage treatment on various plants Bent grass, Kentucky bluegrass, cucumber, tomato, and crabgrass with a height of 5 to 6 cm, which were sown and grown in the same manner as in Experimental Example 1, were treated with the same formulation as in Example 3. The prepared emulsion of each test compound was diluted with water,
The prescribed amount of active ingredient is 250g per 10 ares. 500g
It was sprayed with a small sprayer so that The investigation is disseminated
After 30 days, plant height was measured and averaged. The result is the third
As shown in the table. Note that, as in Experimental Example 1, the numerical values of the effects shown in Table 3 represent the degree of growth inhibitory activity.

【table】

[Table] Experimental example 3 Growth inhibition test on grass by foliage treatment in the field Three-year-old bentgrass transplanted to the field was planted in 1 plot 1
Divide the area into 1m x 1m plots and grow 1 meter of grass during the period of active grass growth.
A wettable powder of each test compound prepared according to the formulation according to Example 1 was diluted with water, and the amount was 1 cm per 1 ^m2 .
It was sprayed with a small sprayer so that the amount was 2g, 2g, and 4g. The survey measured the plant height 40 days after spraying and the fresh weight when the grass was cut to 1 cm. The results are shown in Table 4.

[Table] Experimental example 4 Pre-emergence soil treatment on rice seedlings to prevent growth Rice seedling box (vertical 30cm x width 60cm x depth 3
cm) with 3.2 kg of paddy soil, sow 200 g of sprouting fir (rice variety: Koshihikari), and 0.8 kg of paddy soil.
Cover the soil with soil, and dilute the hydrating agent of each test compound prepared according to the formulation according to Example 1 with water to give a predetermined amount of active ingredient, 0.1 g, 0.5 g, 1.0 g, per seedling box.
It was sprayed with a small sprayer so that the amount was 2.0g. The test was conducted in a Phytotron controlled at 25-30°C. The survey measured plant height, root length, leaf age, leaf blade area, stem and leaf weight, and root weight on the 40th day of application. The result is the fifth
As shown in the table. The values shown in Table 5 are the average values of 50 individuals, and the weights are dry weights.

【table】

[Table] Experimental example 5 Young rice seedlings grown in seedling boxes were placed in 1 section of 2.5 m x
Five plants per plant were transplanted to a field divided into 2 m squares at a cultivation density of 30 cm x 12 cm. On the 40th day of transplantation, the hydrating powder of each test compound prepared according to the formulation in Example 1 was diluted with water, and the amount of active ingredient per 10 ares was 200 g, 400 g.
It was sprayed with a small sprayer so that the amount was 600g.
The investigation was carried out by measuring the number of stems per plant, panicle length, 1st to 5th internode length, and 4th and 5th node unit dry weight on the 20th day after heading. The results are shown in Table 6. The values shown in Table 6 are the average values of 50 individuals.

[Table] Experimental Example 6 Initial growth control test of cucumber and rice (inside germination test) Spread paper in a Petri dish with a diameter of 9 cm, and test the test compound.
Add 15ml of 10ppm solution and add cucumber (variety:
Tokiwa) seeds and 10 rice (variety: Sasanishiki) seeds were placed on each bed. The test was repeated three times for each seed, and during the test period, the seeds were grown under control in a phytotron with a temperature controlled at 25°C. For cucumbers, the length of the hypocotyl, root length, dry weight of shoots and leaves, and dry weight of roots were measured 17 days after immersion in the chemical, and for rice, plant height, length of second leaf sheath, dry weight of shoots and leaves, and dry weight of shoots and leaves were measured for rice. Root dry weight was measured. The results are shown in Table 7 for cucumber and Table 8 for rice. The values shown in Tables 7 and 8 are the average values of 30 individuals.

【table】

【table】

[Table] Experimental Example 7 Elongation prevention test by mixing rice seedling culture soil 2 g and 1 g of the hydrating powder of each test compound prepared according to the formulation according to Example 1 were uniformly mixed in 4 kg of soil, and the rice seedling growing box ( 3.2 kg of rice was placed in a 30 cm vertical x 60 cm wide x 3 cm tall area, and 200 g of sprouting fir (rice variety: Koshihikari) was sown therein, and after watering, the soil was covered with the remaining 0.8 kg of soil. The test was conducted in a Phytotron with humidity controlled at 25-30°C. The survey measured plant height, root length, leaf age, stem and leaf weight, and root weight on the 25th day of sowing. The results are shown in Table 9. Note that the values shown in the table are the average values of 50 individuals.

【table】

[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 50 parts by weight Sodium alkyl sulfate 2.5 〃 Polyoxyethylene alkyl phenyl ether 2.5 〃 Clay 45 〃 These are thoroughly mixed until homogeneous and pulverized to obtain a wettable powder. Example 2 Compound No. 1 10 parts by weight Sodium ligninsulfonate 1 Bentonite 30 Talc 59 These are thoroughly mixed until uniform and granulated to obtain granules. Example 3 Compound No. 2 10 parts by weight Polyoxyethylene alkyl phenyl ether 7 Calcium alkylaryl sulfonate
3 xylene 60 cyclohexanone 20 Mix and dissolve these thoroughly until uniform to obtain an emulsion.

Claims (1)

[Claims] 1. General formula (In the formula, R ₁ 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 methyl group, n represents an integer from 0 to 2, and Z represents a hydrogen atom or An isonicotinic acid anilide derivative represented by (indicates a halogen atom). 2 General formula (In the formula, Y represents a halogen atom.) Isonicotinic acid derivatives represented by the general formula (In the formula, R ₁ 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 methyl group, n represents an integer from 0 to 2, and Z represents a hydrogen atom or A general formula characterized by reacting an aniline derivative represented by (representing a halogen atom) (In the formula, R ₁ , R ₂ , X, n and Z have the same meanings as above.) A method for producing an isonicotinic acid anilide derivative represented by the following. 3 General formula (In the formula, R ₁ represents a hydrogen atom or a lower alkyl group, X represents a halogen atom or a methyl group,
n represents an integer from 0 to 2, and Z represents a hydrogen atom or a halogen atom. ) A general formula characterized by reducing the isonicotinic acid derivative represented by (In the formula, R ₁ , X, n and Z have the same meanings as above, and R ₂ represents a hydrogen atom or a hydroxyl group.) A method for producing an isonicotinic acid anilide derivative represented by the following. 4 General formula (In the formula, R ₁ 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 methyl group, n represents an integer from 0 to 2, and Z represents a hydrogen atom or 1 of isonicotinic acid anilide derivatives represented by (representing a halogen atom)
A plant growth regulator characterized by containing one or more species as active ingredients.