JPH0217546B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula () (In the formula, R ₁ represents a lower alkyl group, R ₂ represents a hydrogen atom or a lower alkyl group, and A represents a lower alkyl group.

【formula】 base or

[Formula] represents a group, and X represents a halogen atom. However, isonicotinic acid-2-acetyl-
Excluding 4-chloroanilide and isonicotinic acid-4-chloro-2-(α-hydroxyethyl)anilide. ), 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, and to prevent lodging in transplanted paddy fields, and can also have the effect of increasing yield. Furthermore, the same effects as on rice can be achieved on wheat, corn, sugarcane, etc. 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. In recent years, lawns have been widely used in homes, gardens, golf courses, green belts, roadsides, green belts, etc., but their management is not only troublesome;
Since it grows actively in the summer, it requires a great deal of labor and money to harvest it. 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 labor and expense. However, the maintenance work involves great danger. Therefore,
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 phyllophin,
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 It is possible to grow healthy plants without causing any chemical damage such as dead leaves or 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 () (wherein Y represents a halogen atom) isonicotinic acid halide represented by the general formula () in a suitable solvent. (In the formula, R ₁ , R ₂ A and X 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 the formula). In this case, the reaction will proceed more smoothly if a suitable deoxidizing agent is used. In addition, suitable solvents include:
Examples include benzene, toluene, xylene, dichloromethane, chloroform, tetrahydrofuran, dioxane, dimethylformamide, and the like. Examples of deoxidizers include pyridine, triethylamine, caustic soda, caustic potash, soda carbonate,
Examples include potassium carbonate. The reaction proceeds 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, the reaction 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 R ₁ , R ₂ and be able to. Examples of the reducing agent include lithium aluminum hydride and sodium borohydride. In practice, it can be easily produced by using each reducing agent in a conventional manner. Production example 1 Production method of isonicotinic acid-2-acetylanilide (compound number 3) 1.35 g of 2-aminoacetophenone was dissolved in 30 g of pyridine.
ml, cool this solution with ice, and add 2.14 g of isonicotinic acid chloride hydrochloride little by little while stirring. After stirring at room temperature for 8 hours, 100 ml of water was added to the reaction solution to precipitate crystals. This crystal was collected and recrystallized from a mixed solvent of η-hexane-acetic acid ethyl ester, resulting in isonicotinic acid-2-
2.23g (yield 93%) of acetylanilide was obtained. melting point
116-117℃ Elemental analysis value: C ₁₄ H ₁₂ N ₂ O ₂ Molecular weight 240.26 C H N Calculated value (%) 69.99 5.03 11.66 Actual value (%) 70.08 4.98 11.60 Production example 2 Isonicotinic acid-2-acetyl-4- Production of chloroanilide (Compound No. 6) A reaction was carried out in the same manner as in Production Example 1 except that 1.7 g of 2-amino-5-chloroacetophenone was used in place of 2-aminoacetophenone in Production Example 1 to produce isonicotinic acid. -2-acetyl-4-chloroanilide 2.5g
(yield 90%). Melting point 203-205℃ Elemental analysis value: C ₁₄ H ₁₁ ClN ₂ O ₂ Molecular weight 274.71 C H N Calculated value (%) 61.21 4.04 10.20 Actual value (%) 61.09 3.99 10.24 Production example 3 Isonicotinic acid-4-chloro-2 -Production of (α-hydroxyethyl)anilide (compound number 7) 2.5 g of isonicotinic acid-2-acetyl-4-chloroanilide obtained in Production Example 2 was added to 30 ml of methanol.
0.34 g of sodium borohydride is added little by little while cooling with water and stirring. After stirring at room temperature for 3 hours, methanol was distilled off under reduced pressure and 100 ml of water was added to precipitate crystals. Take this crystal and η−
When recrystallized from a hexane-acetic acid ethyl ester mixed solvent, isonicotinic acid-4-chloro-2-(α
-hydroxy-ethyl)anilide (2.3 g (yield 92
%)Obtained. Melting point: 142-143°C Elemental analysis value: C ₁₄ H ₁₃ ClN ₂ O ₂ Molecular weight: 276.62 C H N Calculated value (%) 60.77 4.74 10.12 Actual value (%) 60.70 4.77 10.08 Next, the general formula obtained in this way Representative examples of compounds represented by [ ] 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】

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【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 it 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 usage situation, purpose of use, and plant situation. 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 with reference to Examples. Experimental example 1 Early growth control test for cucumber and rice Spread paper in a Petri dish with a diameter of 9 cm, add 15 ml of an aqueous solution of the test compound at a specified concentration, and add 10 cucumber (variety: Tokiwa) seeds and rice (variety: Sasanishiki) to this. Ten seeds were placed on each bed. In the test, each seed was administered three times per dose, and during the test period, each seed was grown under control in a 5000 lux phytotron with a temperature control of 25°C. In the case of cucumbers, the length of the hypocotyl, root length, dry weight of shoots and leaves, and dry weight of roots were measured 7 days after the chemical treatment, and in the case of rice, the plant height,
The second leaf sheath length, root length, stem leaf dry weight, and root dry weight were measured. The results are shown in Table 2 for cucumber and Table 3 for rice. The numerical values shown in Tables 2 and 3 are the average values of 30 individuals.

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[Table] Experimental example 2 Growth prevention test by mixing rice seedling bed soil 2 g, 1 g, and 0.5 g of hydrating powders of each test compound prepared according to the formulation according to Example 1 were uniformly mixed into 4 kg of soil. Put 3.2 kg into a plastic perforated rice seedling box (length 30 cm x width 60 cm x height 3 cm),
150g of sprouting fir (variety: Koshihikari) was sown on this, and after watering, the soil was covered with the remaining 0.8kg of soil. In the test, the seeds were germinated for 2 days in a phytotron with a temperature control of 25 to 30°C, and then grown outdoors in a vinyl frame. The survey was conducted on the 20th day of sowing, including plant height, root length,
Leaf age, stem and leaf weight, and root weight were measured. The result is the fourth
As shown in the table. Note that the values shown in the table are the average values of 50 individuals.

【table】

【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. 20 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. 22 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. 19 10 parts by weight Polyoxyethylene alkyl phenyl ether 7 Calcium alkylaryl sulfonate 3 Xylene 60 Cyclohexanone 20 These are thoroughly mixed and dissolved until uniform to obtain an emulsion.

Claims (1)

[Claims] 1. General formula (In the formula, R ₁ represents a lower alkyl group, R ₂ represents a hydrogen atom or a lower alkyl group, A represents a [formula] group or a [formula] group, and X represents a halogen atom. However, isonicotine (excluding acid-2-acetyl-4-chloroanilide and isonicotinic acid-4-chloro-2-(α-hydroxyethyl)anilide). 2 General formula (In the formula, Y represents a halogen atom.) An isonicotinic acid halide derivative represented by the general formula (In the formula, R ₁ represents a lower alkyl group, R ₂ represents a hydrogen atom or a lower alkyl group, A represents a [formula] group or a [formula] group, and X represents a halogen atom.) General formula characterized by reacting aniline derivatives (In the formula, R ₁ , R ₂ , A and X have the same meanings as above. However, isonicotinic acid-2-acetyl-4-chloroanilide and isonicotinic acid-4
-Excluding chloro-2-(α-hydroxyethyl)anilide. ) A method for producing an isonicotinic acid anilide derivative represented by 3 General formula (In the formula, R ₁ represents a lower alkyl group, R ₂ represents a hydrogen atom or a lower alkyl group, and X represents a halogen atom.) formula (In the formula, R ₁ , R ₂ , A and X have the same meanings as above. However, isonicotinic acid-4-chloro-2-(α-hydroxyethyl)anilide is excluded.) Method for producing nicotinic acid anilide derivatives. 4 General formula (In the formula, R ₁ represents a lower alkyl group, R ₂ represents a hydrogen atom or a lower alkyl group, A represents a [formula] group or a [formula] group, and X represents a halogen atom. However, isonicotine (excluding acid-2-acetyl-4-chloroanilide and isonicotinic acid-4-chloro-2-(α-hydroxyethyl)anilide). A plant growth regulator characterized by containing it as an ingredient.