JPH05139901A - Freshness retaining agent for plant - Google Patents

Abstract

PURPOSE:To obtain a safe and effective freshness retaining agent for a plant, containing a carbamate derivative or a thiocarbamate derivative as an active ingredient and capable of suppressing the reduction in chlorophyll in the plant and exhibiting suppressing effects on stunting of the plant. CONSTITUTION:A plant freshness retaining agent containing a carbamate derivative or a thiocarbamate derivative expressed by the formula [R<1> is alkyl, alkenyl or (substituted)aryl; R<2> is alkyl; X is 0 or S] [e.g. ethyl N-(n-propyl) carbamothioate] as an active ingredient. The plant freshness retaining agent is preferably used as an aqueous solution containing the compound expressed by the formula at about 10-500ppm concentration. The compound expressed by the formula is obtained by reacting, e.g. an isocyanate or isothiocyanate expressed by the formula R<1>-NCO or R<1>-NCS with an alcohol expressed by the formula R<2>OH, A cut flower, a branch plant, a foliage plant, etc., of a rose, a carnation, a lily, a chrysanthemum, a leatherleaf fern, etc., are used as the plant to be an object of the plant freshness retaining agent.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a plant freshness-retaining agent containing a carbamate derivative or a thiocarbamate derivative as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, silver preparations have mainly been used to maintain the freshness of plants, but it has been pointed out that chemical damage and environmental pollution occur. Also, this silver formulation is effective only on a small number of plants. The carbamate derivative or thiocarbamate derivative according to the present invention is described in JP-B-44-26969 or J. Heterocycle
c. Chem. , 21, 241 (1984), etc., but their freshness-retaining effect on plants has not been known so far.

[0003]

The object of the present invention is to develop a safer and more effective plant freshness-retaining agent.

[0004]

As a result of intensive studies to solve the above problems, the present inventors have found that a carbamate derivative or a thiocarbamate derivative is an extremely effective ingredient for maintaining the freshness of plants, and completed.
That is, according to the present invention, formula (I): R ¹ ═NH—C (═X) —OR ² (I) (wherein R ¹ is an alkyl group, an alkenyl group, or a substituted or unsubstituted group). The present invention relates to a plant freshness-preserving agent comprising a carbamate derivative or a thiocarbamate derivative represented by an aryl group, R ² is an alkyl group, and X is a sulfur atom or an oxygen atom.

In formula (I), the alkyl group represented by R ¹ is a linear or branched alkyl group having 1 to 10 carbon atoms, such as methyl group, ethyl group, propyl group, butyl group, pentyl group. , Hexyl group, heptyl group, octyl group, nonyl group or all possible isomers of decyl group can be mentioned, preferably methyl group, ethyl group, n-propyl group, n-butyl group or n-pentyl group. is there.

The alkenyl group represented by R ¹ is an alkenyl group having 1 to 5 carbon atoms, such as vinyl group and 2-
Examples thereof include a propenyl group, a 3-butenyl group, a 4-pentenyl group and the like.

Examples of the unsubstituted aryl group represented by R ¹ include a phenyl group and a naphthyl group, and examples of the substituted phenyl group include a halogen atom, a lower alkyl group having 1 to 5 carbon atoms, and a carbon atom. A phenyl group or a naphthyl group substituted with one or more of the same or different lower alkoxy groups, nitro groups or trifluoromethyl groups of the formulas 1 to 5, such as (mono-, di-, tri-) halogenophenyl group, (mono , Di, tri-) lower alkylphenyl group, (mono, di, tri-) lower alkoxyphenyl group,
(Mono-, di-, tri-) nitrophenyl group, trifluorophenyl group and the like can be mentioned.

In formula (I), the alkyl group represented by R ² is a linear or branched alkyl group having 1 to 10 carbon atoms, such as a methyl group, an ethyl group, a propyl group,
There can be mentioned all possible isomers of butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group or decyl group, preferably methyl group, ethyl group, n-propyl group, isopropyl group, n- It is a butyl group or an n-pentyl group.

The carbamate derivative or thiocarbamate derivative represented by the above formula (I) of the present invention can be produced by the following method. For example, the formula R ¹ -N
By reacting an isocyanate or isothiocyanate represented by CO or R ¹ -NCS, where R ¹ is as defined above, with an alcohol R ² OH, where R ² is as defined above. The compound of formula (I) can be easily produced.

The plant freshness-retaining agent of the present invention may be in the form of a powder containing the compound represented by the above formula (I), which is an active ingredient, or in the form of a solution, but it is usually in the form of an aqueous solution. In the aqueous solution, a surfactant such as polyoxyethylene sorbitan monooleate or sorbitan monolaurate, various spreading agents, a solvent such as acetone, and the like can be added, and further, if desired, nutrients, A bactericide, a plant growth regulator, a plant hormone, etc. can also be added.

When the plant freshness-retaining agent of the present invention is used, it may vary depending on the type of flower, the method of use, etc., but generally the compound represented by the formula (I) is 1 to 1000 ppm.
Is used as an aqueous solution containing it at a concentration of preferably 10 to 500 ppm, and the treatment method is not particularly limited, but for example, the solution is treated at the cut end of cut flowers, branches or leaves, or It is treated by a method of spraying the solution onto cut flowers, branches, and leaves of plants. As a method for treating cut edges, cut edges of cut flowers, branches, and leaves may be immersed in the plant freshness-retaining agent for a certain period of time, or may be kept immersed. As a method of spraying on the plant body, before or / and after cutting, the whole or a part of the plant body is sprayed or applied.

The target plants of the plant freshness-preserving agent of the present invention are not particularly limited, such as cut flowers, branches and leaves.
Examples include roses, carnations, lilies, chrysanthemums, leather fans, and the like.

[0013]

EXAMPLES The present invention will be described in more detail with reference to production examples and test examples. Production Example 1 Ethyl N- (n-propyl) carbamothioate
Preparation of (Compound No. 3) 1.89 g of monochloroacetic acid was dissolved in 20 ml of 1N-sodium hydroxide aqueous solution, 3.20 g of potassium dithiocarbonate-O-ethyl potassium was added at room temperature, and the mixture was stirred for 1 hour, and then n-
0.59 g of propylamine was added, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was extracted with ethyl acetate, the extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (solvent: hexane-ethyl acetate = 10: 1) to obtain 1.33 g of the title compound as an oily substance.

Production Example 2 Isopropyl N- (n-butyl) carbamothioate
Production of (Compound No. 12) 2.3 g of n-butyl isothiocyanate was dissolved in 40 ml of isopropyl alcohol and stirred at 80 ° C. for 10 hours. The solvent was distilled off from this reaction solution under reduced pressure, and the residue was subjected to silica gel chromatography (solvent: hexane-ethyl acetate =
Purification with 10: 1) gave 2.53 g of the title compound.

Production Example 3 Ethyl N- (n-butyl) carbamate (Compound No.
No. 14) Production of n-butyl isocyanate 2.0 g ethanol 40 ml
And was heated to reflux for 10 hours. The solvent was distilled off from this reaction solution under reduced pressure, and the residue was purified by silica gel column chromatography (solvent: hexane-ethyl acetate = 10: 1) to obtain 2.20 g of the title compound. The compound according to the present invention was produced according to the method of Production Examples 1 to 3. Table 1 shows the series of compounds obtained and their physical properties.

[0016]

[Table 1]

Test Example 1 Nijo barley seeds were treated with 1% sodium hypochlorite solution for 20 times.
After sterilizing for minutes, rinse with water, soak seeds in running water for 24 hours, and sow the seeds on vermiculite.
It was grown for 10 days. When the first leaf is fully expanded,
Select and pick leaves that have a uniform width of leaf blade, and 3 from the tip
A section between ˜4 cm was cut out, and this leaf section was cultured in the dark at 25 ° C. for 24 hours. Five leaf sections were used as a set as a sample, floated in a test solution containing 500 ppm of the test compound and a control solution (distilled water), and cultured at 25 ° C. for 48 hours in the dark. The sample treated in this way was extracted with 90% methanol, and the absorbance (A ₆₅₃ , A ₆₆₆ ) of the extract at ₆₅₃ nm and 666 nm was measured by a spectrophotometer, and the amount of chlorophyll per unit weight in the sample (G; μg / μg / m
g) was calculated by the following calculation formula. G = [(A ₆₅₃ × 23.6 + A ₆₆₆ × 2.57) ×
Extract (ml)] ÷ Sample weight (mg) The chlorophyll retention activity of the test compound was determined by the following formula. Chlorophyll retention activity (%) = [G ¹ (test sample treated)
÷ G ⁰ (control solution-treated sample)] × 100 For each test compound, the chlorophyll retention activity was determined according to the following evaluation criteria, and the obtained results are shown in Table 2. Evaluation criteria A: Chlorophyll retention activity 250% or more B: Chlorophyll retention activity 150 to 250% C: Chlorophyll retention activity less than 150%

[0018]

[Table 2]

Test Example 2 A test compound was dissolved in dimethyl sulfoxide to form a 2% solution, and this solution was diluted with water to give 500 ppm of the test compound.
A test solution containing was obtained. Roses (variety: Libya) were inserted into this test solution and repeat (Taisho Pharmaceutical Co., Ltd., registered trademark) 50-fold diluted aqueous solution and distilled water as a control, and stored in a culture chamber at 25 ° C. The condition of each flower was observed 2 days after storage and 5 days after storage, and judged according to the following evaluation criteria. Evaluation Criteria 4: Flowers bloom. The leaves are fresh. I'm not hanging. 3: The leaves are not fresh. 2: Flowers and leaves are not fresh. 1: Flowers and leaves have no freshness. I am hanging. The results obtained are shown in Table 3.

[0020]

[Table 3]

[0021]

The plant freshness-maintaining agent of the present invention suppresses the decrease of chlorophyll in plants and has the effect of suppressing plant atrophy.

Continued Front Page (72) Inventor Masaki Hashimoto 1-1-1 Wakayamadai, Shimamoto-cho, Mishima-gun, Osaka Suntory Ltd. Research Laboratories

Claims (1)

[Claims] 1. Formula (I): R ¹ —NH—C (═X) —OR ² (I) (wherein R ¹ represents an alkyl group, an alkenyl group, or a substituted or unsubstituted aryl group. , R ² is an alkyl group, and X is a sulfur atom or an oxygen atom), and a plant freshness-preserving agent containing a carbamate derivative or a thiocarbamate derivative represented by