JPH0149682B2 - - Google Patents

Description

[Detailed description of the invention]

(Industrial Application Field) The present invention relates to a plant growth regulator, and more particularly to a plant growth regulator comprising an N-acyllactam compound. (Prior art) Auxins, gibberellins, cytokinins, abscisic acid, and ethylene have been known as plant hormones useful for plant growth.
Recently, development research on brassinolide-based hormone agents has been progressing. However, all of these methods have problems, such as being expensive, difficult to manufacture, and having significantly different effects depending on the time of application and the target crop. (Problems to be Solved by the Invention) Under these circumstances, in order to solve the above-mentioned problems, the present inventors have obtained a compound that is inexpensive and has an excellent regulating effect as a plant growth regulator. Hopefully,
As a result of extensive research, the present invention was completed by discovering a new plant growth regulator comprising an N-acyllactam compound as detailed below. (Means for solving the problem) That is, the present invention has the general formula The present invention relates to a plant growth regulator comprising an N-acyllactam compound represented by the formula (wherein n is 1 or 2) or a salt thereof. (Function) The method for producing the N-acyl lactam compound of the present invention is already a well-known method, and can be produced, for example, by the following method. (1) Reaction of lactam and acid anhydride, (2) Direct reaction of lactam and acid chloride, (3) Reaction of lactam and acid chloride in the presence of tertiary amines or dimethylformamide, (4) Reaction of alkali metal salts of lactams with acid chlorides, (5) Reaction of lactim ethers with acid chlorides, (6) Reaction with acid chlorides via trimethylsilylated lactams, (7) 2-chloropyridinium salts It can be produced by reacting an intermediate with an acid and lactim ether. For example, in the production method by direct reaction of lactam and acid chloride, 3-(4-nitro)
After converting phenylpropionic acid into acid chloride with thionyl chloride, phosphorus pentachloride, phosphorus trichloride, oxalyl chloride, etc., reacting with 2-piperidone and then reducing the nitro group, 1-[3- (4-aminophenyl)propanoyl]-2-piperidone can be produced. Furthermore, 1-[2-(4-aminophenyl)ethanoyl]-2-piperidone can be produced by using 2-(4-nitro)phenylacetic acid as a raw material. Moreover, these salts can be manufactured by reacting the above-mentioned compounds with various acids in an organic solvent or an aqueous solution. For example, the acids used in the present invention include hydrochloric acid,
Examples include various inorganic acids and organic acids such as sulfuric acid, nitric acid, phosphoric acid, boric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, and caproic acid, but are not limited to these. The growth regulator of the present invention may be used in liquid or powder form, but liquid form is generally preferred from the viewpoint of uniformity, and its concentration varies depending on the type of plant. When the purpose is growth, it is desirable to apply it in an aqueous solution of approximately 10 mg/1 or less, and when the purpose is dwarfing, it is desirable to apply it as an aqueous solution of 500 mg/1 or more. Further, the method may be any method such as foliar spraying, application to soil, or addition to a fertilizer solution in hydroponic methods.
Alternatively, it may be applied to the transplanted soil or hydroponic cultivation tank in advance before planting the plants. Generally, the application period is preferably the seedling stage, but is not limited to this. (Example) The present invention will be further explained below with reference to Examples.
The present invention is not limited to these. Moreover, all percentages indicate weight % unless otherwise specified. Production Example 1 A mixture of 14 ml of concentrated nitric acid (65%) and 14 ml of concentrated sulfuric acid was cooled to 10°C in an ice bath, and stirred for 1 hour to form a 3-
6.4 g of phenylpropionic acid is added until the temperature of the reaction mixture is
Drip so that the temperature does not exceed 20℃. After adding 1
Stir at room temperature for an hour. Pour this into 100ml of water,
The precipitate was filtered using a glass filter and recrystallized from ethanol to give pale yellow crystals.
6.3 g of -(4-nitro)phenylpropionic acid was obtained. Next, 1.3 times the mole of thionyl chloride is added, and the mixture is kept under reflux conditions at 80°C for 3 hours. After the reaction, thionyl chloride, hydrochloric acid gas, and sulfur dioxide gas were removed under reduced pressure, and then reacted with 2-piperidone to form 1-
[3-(4-nitrophenyl)propanoyl]-2
- Obtained 5.4 g of piperidone. Next, after dissolving this substance in ethyl acetate, it was kept at room temperature under stirring conditions in a hydrogen stream using 5% palladium carbon as a catalyst for 5 hours, and after the reaction, ethyl acetate was distilled off and 1-[3-(4
3.8 g of -aminophenyl)propanoyl]-2-piperidone were obtained. Production Example 2 Using 10.3 g of 2-phenylacetic acid, 5.4 g of 1-[2-(4-aminophenyl)ethanoyl]-2-piperidone was obtained by the same operation as in Production Example 1. Production Example 3 50ml of 1g of 1-[3-(4-aminophenyl)propanoyl]-2-piperidone obtained in Production Example 1
The mixture was dissolved in ethyl acetate, and hydrochloric acid gas was blown into the solution under ice cooling, and when the formation of a white suspension stopped, the suspension was filtered off. The white suspension was then washed several times with ether and dried to give 1-[3-(4-aminophenyl)propanoyl]-2-piperidone hydrochloride.
Obtained 1.1g. Production Example 4 2.3 g of 1-[2-(4-aminophenyl)ethanoyl]-2-piperidone obtained in Example 2 was dissolved in 100 ml of ethyl acetate, placed in an Erlenmeyer flask, and stirred in an ice bath. 1.2 g of caproic acid was slowly added dropwise. After the addition, ethyl acetate and excess caproic acid were removed by vacuum distillation to obtain 3.2 g of caproate of 1-[2-(4-aminophenyl)ethanoyl]-2-piperidone. Production Example 5 2.4 g of 1-[3-(4-aminophenyl)propanoyl]-2-piperidone obtained in Production Example 1 was
ml of ethyl acetate, put this into a separating funnel, added and mixed 80 ml of 0.1N nitric acid aqueous solution and ice chips, and then separated the aqueous layer. After confirming that the PH of the fractionated sodium bicarbonate is neutral,
This was concentrated under reduced pressure and the nitrate of 1-[3-(4-aminophenyl)propanoyl]-2-piperidone was obtained.
Obtained 2.0g. Table 1 lists the names of substances and their sample symbols that will be used thereafter. Example 1 The compounds shown in Table 1 were mixed with ethyl acetate at 10 mg/1.
1mg/1, 0.1mg/1, 0.01mg/1, put a filter paper (70mmφ) in a Petri dish, add 2ml of sample solution, distill off ethyl acetate under reduced pressure, add 2ml of distilled water, Sow 25 Komatsuna seeds in a dark place.
It was kept at 25℃. After 48 hours, the stem length and root length were measured and the rate of change was determined. The same test was conducted using distilled water as a control test. The results are shown in Table 2.

【table】

【table】

[Table] Note) ±: -5 < rate of change < +5 is displayed.
Measured value for additive category - Measured value for non-additive category Rate of change =

Claims (1)

[Claims] 1. General formula A plant growth regulator comprising an N-acyllactam compound represented by the formula (wherein n is 1 or 2) or a salt thereof.