JPH0149324B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a plant growth regulator. Currently, plant hormones include auxins,
Gibberellins, cytokinins, abscisic acid, and ethylene are known, but there are problems such as significantly different effects depending on the time of application and the target crop. For example, auxins have no practical value when used as herbicides. Currently, gibberellins are only used for seedless grapes as dwarfing agents. The present inventors have conducted various studies aimed at discovering a new, inexpensive growth regulator using a synthetic method, and as a result, have discovered a new plant growth agent described in detail below, and have completed this discovery. That is, the present invention has the following general formula: (However, R ¹ is H, CH ₃ -

[expression] or

[Formula] R represents -CH ₂ -, -CH ₂ -CH ₂ -, or -CH=CH-, and n = 3 to 5) Plant growth regulator consisting of an N-acyllactam compound Regarding. The growth agent of the present invention can be produced by a well-known method: (1) Reaction of lactam and acid anhydride (2) Direct reaction of lactam and acid chloride (3)
Reaction of lactam with acid chloride in the presence of tertiary amines or dimethylformamide (4) Reaction of alkali metal salt of lactam with acid chloride (5) Reaction of lactim ether with acid chloride (6) Trimethylsilylation Reaction with an acid chloride via a lactam (7) It can be easily produced by reacting an intermediate with an acid using a 2-chloropyridinium salt and a lactam. For example, regarding the production method using the direct reaction method of lactam and acid chloride, after benzylating the hydroxyl group of the methyl ester of 4-hydroxyphenylacetic acid, 4-hydroxyphenylpropionic acid, and 4-hydroxycinnamic acid, the ester is By hydrolyzing and acid chloridizing with thionyl chloride, phosphorus pentachloride, phosphorus trichloride, oxalyl chloride, etc., and then reacting with 2-pyrrolidone, 2-piperidone or ε-caprolactam, R ¹ is

[Formula] N-acyllactam compounds in which R is -CH ₂ -, -CH ₂ -CH ₂ -, -CH=CH-, and n = 3 to 5 can be produced. In addition, by hydrogenolyzing each of the above N-acyllactam compounds, R ¹ in the general formula
is H, R is respectively -CH ₂ -, -CH ₂ -CH ₂ -,
N-acyllactam compounds where n=3 to 5 can be produced. In addition, R ¹ in the general formula is CH ₃ -,

[Formula] The N-acyllactam compound in which R is -CH ₂ -, - CH ₂ -CH ₂ -, n = 3 to 5 is the above-mentioned

It can be produced by methylating, acetylating, or benzoylating [Formula]. Also, R ¹ is H, R is -CH=CH-, n=3~
The N-acyllactam compound No. 5 is obtained by methylating the -OH group of 4-hydroxycinnamic acid, converting it into acid chloride, and reacting it with each corresponding lactam.
It can be produced by acid hydrolysis. 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 use approximately 50 mg/or less, and when the purpose is dwarfing, it is desirable to use 500 mg/or more. Generally, the seedling stage is desirable as the application time, but it is not limited to this. The present invention will be further explained below with reference to Examples. Production example: 1g of 4-hydroxyphenylpropionic acid
Add 10 ml of 5W/V% methanol sulfate, hold at 80°C under reflux conditions for 6 hours, and add ether after the reaction.
After separating the ether layer, it was washed successively with 1N sodium hydroxide and water, and after dehydration, the ether was distilled off.
The methyl ester is obtained. After dissolving the methyl ester in 10 times the amount of dimethylformamide, add an equimolar amount of anhydrous potassium carbonate, then add an equimolar amount of benzyl chloride, hold at 80°C under reflux conditions for 6 hours, and after the reaction, add ether and dissolve in 1N hydrochloric acid. After washing the ether layer with the solution, 1N sodium hydroxide solution, and water in this order, the ether is distilled off to obtain benzyl ether. Add 10 times the volume of 1N potassium hydroxide solution to benzyl ether,
Heat to ~190°C and cool when the oil disappears to a white suspension. Separate the white suspension,
After dissolving in excess ether, the mixture is washed successively with 1N hydrochloric acid solution and water, and after dehydration, the ether is distilled off to obtain a white powder. Add 1.3 times the mole of thionyl chloride to the white powder,
Maintain at 80°C for 3 hours under reflux conditions. After the reaction, thionyl chloride and hydrochloric acid gas are removed under reduced pressure, a 2-fold molar pyridine solution of 2-piperidone is added, a calcium chloride tube is attached, and the mixture is kept at 80°C for 5 hours. After the reaction, ether was added, and the ether layer was separated, washed with 1N hydrochloric acid solution, 1N sodium hydroxide solution, and water in this order. After dehydration, the ether was distilled off and 1-[3-(4-benzyloxy phenyl)
1.42 g of propanoyl]-2-piperidone is obtained.
Next, after dissolving this substance in ethanol, 5%
Using pd/c as a catalyst, under stirring conditions in a hydrogen stream,
After the reaction, the ethanol was distilled off, extracted with water-methanol (1:1), and the 1-
[3-(4-hydroxyphenyl)propanoyl]
0.74 g of -2-piperidone was obtained. Example 1 The compounds shown in Table 1 were mixed with methanol at 1000mg/
, 500mg/, 200mg/, put a piece of paper (70mmφ) in a Petri dish, and add 2ml of the sample methanol solution.
Add 2 ml of distilled water after distilling off the methanol under reduced pressure.
25 Komatsuna seeds were sown and kept in the dark at 30°C. 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] *No germination
Measured value for added category - Measured value for non-additive category
Rate of change =

Claims (1)

[Claims] 1. General formula (However, R ¹ is H, CH ₃ -,
[Formula] or [Formula] R represents -CH ₂ -, -CH ₂ -CH ₂ -, or -CH=CH-, and n = 3 to 5). Plant growth regulator.