JP2011201806A - New compound having plant growth-regulating action and method for producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To develop a new compound having a plant growth-regulating action.SOLUTION: There are provided new 3-(3-tertiary amyl-4-hydroxyphenyl)propionic acid, new 3-tertiary amyl-4-hydroxycinnamic acid, new 3-(3-isopropyl-4-hydroxyphenyl)propionic acid, and new 3-isopropyl-4-hydroxycinnamic acid. At least one selected from the group consisting of the new compounds is used for regulating the growth of plants. There are provided methods for producing four kinds of the new compounds.

Description

  The present invention relates to four kinds of novel compounds exhibiting a plant growth promoting or inhibiting action and methods for producing them.

  The inventors have studied the physiological effects of extracts from waste plastics. In that case, it discovered that the 3- (4-hydroxyphenyl) propionic acid type compound different from auxin and gibberellin which are conventionally well-known plant growth promoters showed a plant growth promotion effect | action. Therefore, synthesis of 3- (4-hydroxyphenyl) propionic acid compounds having various substituents on the phenyl group was attempted. Patent Document 1 discloses a compound in which the phenolic hydroxyl group of 3- (4-hydroxyphenyl) propionic acid is protected.

  The present inventors also provide a 4-hydroxycinnamic acid compound in which the first and second carbons of propionic acid are double bonds in the propionic acid compound, and various substitutions are made on the phenyl group. An attempt was also made to synthesize one having a group. In addition, about the cinnamic acid ester by which 4th-position of the benzene ring was substituted, the manufacturing method is disclosed by patent documents 2 and 3.

JP-A-11-29533 JP-A-6-312956 JP 7-252192 A

  An object of the present invention is to find a 3- (4-hydroxyphenyl) propionic acid compound or a related compound, a 4-hydroxycinnamic acid compound, which exhibits a plant growth promoting or inhibiting action. .

  The present inventors are a 3- (4-hydroxyphenyl) propionic acid compound and a related compound, 4-hydroxycinnamic acid compound, in which a 3-tertiaryamyl group is introduced into a benzene ring And a compound into which an isopropyl group was introduced were synthesized. And it was investigated whether the compound synthesize | combined showed a plant growth promotion or suppression effect, As a result, this invention was completed. All of the four compounds according to the present invention shown below are novel compounds according to Chemical Abstract and SciFinder Scholar.

That is, the present invention relates to 3- (3-tertiaryamyl-4-hydroxyphenyl) propionic acid represented by the following formula A.

The present invention also relates to 3-tertiaryamyl-4-hydroxycinnamic acid represented by the following formula B.

Furthermore, the present invention relates to 3- (3-isopropyl-4-hydroxyphenyl) propionic acid represented by the following formula C.

In addition, the present invention relates to 3-isopropyl-4-hydroxycinnamic acid represented by the following formula D.

  The present invention relates to a plant growth regulator containing at least one of the compounds represented by the formulas A to D. Here, the “plant growth regulator” is a concept including both a plant growth promoter and a plant growth inhibitor. Even if it is the same compound, it may act as a plant growth promoter or a plant growth inhibitor depending on the kind of plant to be used and the concentration at the time of use.

The present invention is a process for producing 3- (3-tertiaryamyl-4-hydroxyphenyl) propionic acid or 3- (3-isopropyl-4-hydroxyphenyl) propionic acid, which undergoes the following steps (I) to (III). About:
(I) a step of introducing a protecting group into a phenolic hydroxyl group of a phenol having an aldehyde group at the para position and a substituent at the ortho position (provided that the substituent is a tertiary-amyl group or an isopropyl group);
(II) a step of converting an aldehyde group into an acrylic acid group; and (III) a step of removing the protecting group and hydrogenating the acrylic group.

The present invention also relates to a method for producing 3-tertiaryamyl-4-hydroxycinnamic acid or 3-isopropyl-4-hydroxycinnamic acid, which undergoes the following step (i):
(I) A step of converting an aldehyde group of a phenol having an aldehyde group at the para position and a substituent at the ortho position (wherein the substituent is a tertiaryamyl group or an isopropyl group) into an acrylic acid group.

  Each of the two types of production methods described above further provides a phenol having an aldehyde group at the para-position and a substituent at the ortho-position (provided that the substituent is a tertiary-amyl group or an isopropyl group) as a raw material. It may include a step of introducing an aldehyde group into the para position of the phenol having the substituent at the meta position.

  According to the present invention, four novel compounds are provided. Since these compounds exhibit plant growth regulating action, options for plant growth regulators are expanded.

¹ is a ¹ H-NMR chart of 3-tertiaryamyl-4-hydroxybenzaldehyde. 3 is a mass spectrum of 3-tertiaryamyl-4-hydroxybenzaldehyde. ¹ is a ¹ H-NMR chart of 3-tertiaryamyl-4-benzyloxybenzaldehyde. ¹ is a ¹ H-NMR chart of 3-tertiaryamyl-4-benzyloxycinnamic acid. ¹ is a ¹ H-NMR chart of 3- (3-tertiaryamyl-4-hydroxyphenyl) propionic acid. 3 is a mass spectrum of 3- (3-tertiaryamyl-4-hydroxyphenyl) propionic acid. ¹ is a ¹ H-NMR chart of 3-tertiaryamyl-4-hydroxycinnamic acid. It is a mass spectrum of 3-tersialia-4-hydroxycinnamic acid. ¹ is a ¹ H-NMR chart of 3-isopropyl-4-hydroxybenzaldehyde. It is a mass spectrum of 3-isopropyl-4-hydroxybenzaldehyde. ¹ is a ¹ H-NMR chart of 3-isopropyl-4-benzyloxycinnamic acid. ¹ is a ¹ H-NMR chart of 3- (3-isopropyl-4-hydroxyphenyl) propionic acid. 3 is a mass spectrum of 3- (3-isopropyl-4-hydroxyphenyl) propionic acid. ¹ is a ¹ H-NMR chart of 3-isopropyl-4-hydroxycinnamic acid. It is a mass spectrum of 3-isopropyl-4-hydroxycinnamic acid. It is a graph which shows the measurement result of the hypocotyl length of the Japanese radish cultivated using the compounds A and B. It is a graph which shows the measurement result of the hypocotyl length of the broccoli grown using the compounds A and B. It is a graph which shows the measurement result of the hypocotyl length of mustard cultivated using compounds A and B. It is a graph which shows the measurement result of the fresh weight of the Japanese radish cultivated using the compounds A and B. It is a graph which shows the measurement result of the fresh weight of the broccoli grown using the compounds A and B. It is a graph which shows the measurement result of the fresh weight of the mustard grown using the compounds A and B. It is a graph which shows the measurement result of the dry weight of the Japanese radish grown using the compounds A and B. It is a graph which shows the measurement result of the dry weight of the broccoli grown using the compounds A and B. It is a graph which shows the measurement result of the dry weight of the mustard grown using the compounds A and B. It is a graph which shows the measurement result of the length of the lettuce seed root cultivated using compounds A, B, C, and D.

  The compounds according to the present invention are the four compounds represented by the above chemical formulas A to D. These are all novel compounds. In the following, each of these may be referred to as Compound A, Compound B, Compound C, and Compound D.

The molecular formula of Compound A is C ₁₄ H ₂₀ O ₃ and the molecular weight is 238. The appearance is colorless or white needle-like crystals. Compound B has a molecular formula of C ₁₄ H ₁₈ O ₃ and a molecular weight of 234. The appearance is a slightly colored crystal. The molecular formula of Compound C is C ₁₂ H ₁₆ O ₃ and the molecular weight is 208. Moreover, the external appearance is a white needle crystal. Compound D has a molecular formula of C ₁₂ H ₁₄ O ₃ and a molecular weight of 206. The appearance is a slightly colored crystal.

  Next, the manufacturing method of these compounds is demonstrated. First, compounds A and C, that is, a method for producing a propionic acid compound in the present invention will be described with reference to the following reaction route diagram.

  In the method for producing a propionic acid-based compound of the present invention, a phenol (compound (2)) having an aldehyde group at the para position and a substituent at the ortho position (provided that the substituent is a tertiary-amyl group or an isopropyl group), 3-tertiaryamyl-4-hydroxybenzaldehyde or 3-isopropyl-4-hydroxybenzaldehyde is used as a raw material.

Here, the method for obtaining the compound (2) is not limited, but the compound (2) can be obtained by, for example, step (0) using 2-tertiaryamylphenol or 2-isopropylphenol (compound (1)) as a starting material. Can be synthesized. Specifically, dichlorocarbene (: CCl ₂ ) generated from chloroform and a base (for example, NaOH or KOH) is used as an active species, and hydrogen bonded to carbon of the benzene ring is converted to an aldehyde group (Limmer-Chiman). reaction).

  In addition, an aldehyde group is introduced into the aromatic group by a known reaction such as a Gutterman-Koch reaction, a Gutterman reaction, a Vilsmeier-Hack reaction, a Duff reaction, a Friedel-Crafts reaction, or a reaction using organolithium as an intermediate. (Formylation).

  Step (I) is a step of introducing a protecting group into the phenolic hydroxyl group of compound (2). In this step, hydrogen of the hydroxyl group is substituted with a group generally used for protecting the hydroxyl group. Specific examples of groups introduced for protection include benzyl, methyl, p-methoxybenzyl, tert-butyl, methoxymethyl, trimethylsilyl, triethylsilyl, tert-butyldimethylylsilyl Acetyl group, benzoyl group, trityl group and the like. The protecting group is selected in consideration of deprotection conditions. In this invention, it is preferable to protect by a benzyl group from a viewpoint that deprotection can be performed simultaneously with hydrogenation to a carbon-carbon double bond in step (III).

  Step (II) is a compound in which a phenolic hydroxyl group is protected, for example, an aldehyde group of 3-tertiaryamyl-4-benzyloxybenzaldehyde or 3-isopropyl-4-benzyloxybenzaldehyde (compound (3)), This is a step of converting to an acrylic acid group. Here, malonic acid, which is a dicarboxylic acid, is reacted with an aldehyde group and converted to an acrylic acid group. In this way, 3-tertiaryamyl-4-benzyloxycinnamic acid or 3-isopropyl-4-benzyloxy cinnamic acid (compound (4)) is obtained.

  Step (III) is a step of removing the protecting group of the phenolic hydroxyl group and hydrogenating the acrylic group. This may be performed by subjecting the compound (4) to a hydrogenation reaction using a catalyst. By this step, 3- (3-tertiaryamyl-4-hydroxyphenyl) propionic acid or 3- (3-isopropyl-4-hydroxyphenyl) propionic acid (compound (5)) is synthesized.

  Then, the manufacturing method of compound B and D, ie, a cinnamic-acid type compound in this invention, is demonstrated, referring the following reaction pathway diagrams.

  In the method for producing a cinnamic acid-based compound of the present invention, one step (process) from the compound (2) described above, that is, 3-tertiaryamyl-4-hydroxybenzaldehyde or 3-isopropyl-4-hydroxybenzaldehyde. In (i)), the target substance, 3-tertiaryamyl-4-hydroxycinnamic acid or 3-isopropyl-4-hydroxycinnamic acid, is obtained. The method for producing compound (2) is as described above.

  A reaction in which an aromatic aldehyde and a carboxylic acid anhydride undergo dehydration condensation under basic conditions is known as a Parkin reaction.

  In carrying out the production method according to the present invention, the reaction conditions are determined for each reaction with reference to general conditions for organic synthesis. In addition, acquisition and purification of the target substance from the reaction mixture may be performed by a known method such as solvent extraction, use of chromatography, recrystallization, and the like.

  The novel compounds of the present invention are useful as plant growth regulators. As described above, these compounds may act as a growth promoter or may act as a growth inhibitor depending on the type of target plant and the concentration at the time of use. Therefore, the concentration at the time of use is determined according to the type and purpose (promotion or suppression) of the target plant. For example, the concentration when used as a growth promoter is about 0.1 to 100 ppm, and the concentration when used as a growth inhibitor is about 10 to 200 ppm.

  Further, since the novel compound of the present invention has low solubility in water, it is preferably dissolved in an organic solvent in advance and then diluted with water or used as an emulsion.

  Hereinafter, the present invention will be described specifically by way of examples. First, the synthesis of the compound of the present invention will be described.

Example 1 Synthesis of 3- (3-tert-amyl-4-hydroxyphenyl) propionic acid [3- (3-tert.-Amyl-4-hydroxyphenyl) propionic acid; molecular weight: 236] (Compound A) According to the reaction route diagram shown in Chemical formula 5], the desired compound A (compound (5) (where R is a tertiary-amyl group) in the reaction route diagram) was synthesized from compound (1).

(1) 3-Tertariamil-4-hydroxybenzaldehyde [3-tert. Synthesis of -Amyl-4-hydroxybenzaldehyde; molecular weight: 192] (compound (2)) Hydroxylation of 2-tertiaryamylphenol (8.2 g; 0.05 mol) (compound (1)) in methanol (40 ml) A solution of sodium (30 g) in water (40 ml) was added. The temperature of the water bath was adjusted so that the internal temperature of the obtained solution was 60 ° C., and chloroform (10 g) was added dropwise to the solution over 1 hour. The reaction mixture was kept at the same temperature for a further 3 hours and then cooled on ice. 4N hydrochloric acid was added to the resulting reaction mixture to adjust the pH to 5-6. Subsequently, chloroform extraction including insolubles was performed, and the chloroform layer was separated and dried over magnesium sulfate. Chloroform was distilled off and the residue was dissolved in a small amount of methylene chloride. This solution was subjected to silica gel column chromatography and eluted with a mixed solution of hexane and ethyl acetate (4: 1; volume ratio) to obtain the desired product (4.8 g; yield 50%) (compound (2)). It was.
A ¹ H-NMR chart of the obtained compound (2) is shown in FIG. 1, and a mass spectrum is shown in FIG.

(2) 3-Tertariamil-4-benzyloxybenzaldehyde [3-tert. -Amyl-4-benzoxybenzaldehyde: Synthesis of molecular weight: 282] (Compound (3)) Compound (2) synthesized in (1) (3.84 g; 0.02 mol), benzyl chloride (2.77 g; 0.022 mol) And potassium carbonate (4.14 g; 0.03 mol) were reacted in dimethylformamide (DMF; 20 ml) at 120 ° C. for 1 hour. The reaction mixture was allowed to cool, and purified water (100 ml) was added at room temperature. Subsequently, ethyl acetate extraction including insolubles was performed, and the ethyl acetate layer was separated, washed with water and brine, and dried over magnesium sulfate. Ethyl acetate was distilled off to obtain the desired product (5.1 g; yield 90%) (compound (3)) as a residue.
FIG. 3 shows a ¹ H-NMR chart of the obtained compound (3).

(3) 3-Tertariamil-4-benzyloxycinnamic acid [3-tert. -Amyl-4-benzoxycinnamic acid; Molecular weight: 324] (Chemical compound (4)) Synthesis (3) Compound (3) (2.82 g; 0.01 mol), malonic acid (1.25 g; 0) 0.012 mol) and piperidine (100 mg) were reacted in pyridine (10 ml) at about 100 ° C. for 5 hours, and the mixture was ice-cooled. 2N hydrochloric acid was added to the resulting reaction mixture to adjust the pH to 1-2. Subsequently, ethyl acetate extraction including insolubles was performed, and the ethyl acetate layer was separated, washed with brine, and dried over magnesium sulfate. Ethyl acetate was distilled off to obtain the desired product (compound (4)) (2.4 g; yield 74%) as a residue.
FIG. 4 shows a ¹ H-NMR chart of the obtained compound (4).

(4) Synthesis of 3- (3-tertiaryamyl-4-hydroxyphenyl) propionic acid [3- (3-tert.-Amyl-4-hydroxyphenyl) propionic acid; molecular weight: 236] (compound (5)) 1) to (3) were repeated, and the resulting compound (4) was combined. Such compound (4) (3.2 g; 0.01 mol) was dissolved in 50 ml of a tetrahydrofuran (THF) / methanol mixture (5: 1; volume ratio). 10% palladium carbon catalyst (500 mg) was added to the resulting solution, and a hydrogenation reaction was performed under pressure (4 kg / cm ₂ ). After completion of the reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in a small amount of methylene chloride. This solution was subjected to silica gel column chromatography and eluted with a chloroform / methanol mixture (50: 1; volume ratio) to obtain the desired product (compound (5) (2.0 g; yield 84.7%)). It was.

The obtained compound (5) was a white needle crystal and was a single spot (Rf = 0.7) by thin layer chromatography on silica gel G (developing solvent: chloroform / methanol = 10/1). In addition, a ¹ H-NMR chart of this compound is shown in FIG. 5, and a mass spectrum is shown in FIG.

(Example 2) 3-Tertariamil-4-hydroxycinnamic acid [3-tert. Synthesis of -Amyl-4-hydroxycinnamic acid; molecular weight: 234] (Compound B) According to the reaction route diagram shown in [Chemical Formula 6], from the compound (2), the target compound B (compound (6) in the reaction route diagram) (Where R is a tertiary-amyl group)).

  3-tertiaryamyl-4-hydroxybenzaldehyde (3.8 g; 0.02 mol), acetic anhydride (10 ml) and potassium carbonate (3.5 g; 0.025 mol) synthesized by the method described in Example 1 (1) ) In an oil bath at 120-130 ° C. for 3 hours. After allowing to cool, distilled water (20 ml) was added to the reaction mixture. Thereafter, the solvent was distilled off under reduced pressure, and the residue was dissolved in a 10% aqueous sodium hydroxide solution (10 ml). In this state, the reaction was allowed to proceed for 2 hours at room temperature. To the resulting reaction mixture, 10% hydrochloric acid was added to adjust the pH to 2-3. Subsequently, chloroform extraction including insolubles was performed, and the chloroform layer was separated and dried over magnesium sulfate. Chloroform was distilled off under reduced pressure, and the residue was dissolved in a small amount of methylene chloride. This solution was subjected to silica gel column chromatography and eluted with a chloroform / methanol mixture (20: 1; volume ratio) to obtain the desired product (compound (6)) (4.0 g; yield 85%). .

The obtained compound (6) was a slightly colored crystal, and was a single spot (Rf = 0.4) by thin layer chromatography on silica gel G (developing solvent: chloroform / methanol = 10/1). Further, a ¹ H-NMR chart of this compound is shown in FIG. 7, and a mass spectrum is shown in FIG.

Example 3 Synthesis of 3- (3-isopropyl-4-hydroxyphenyl) propionic acid [3- (3-isopropyl-4-hydroxyphenyl) propionic acid; molecular weight: 208] (compound C) The target compound C (compound (5) (where R is an isopropyl group) in the reaction route diagram) was synthesized from the compound (1) according to the reaction route diagram.

(1) Synthesis of 3-isopropyl-4-hydroxybenzaldehyde [3-isopropyl-4-hydroxybenzaldehyde; molecular weight: 164] (compound (2)) 2-isopropylphenol (6.81 g; 0.05 mol) in methanol (40 ml) ) To the solution was added a solution of sodium hydroxide (30 g) in water (40 ml). The temperature of the water bath was adjusted so that the internal temperature of the obtained solution was 60 ° C., and chloroform (10 g) was added dropwise to the solution over 1 hour. The reaction mixture was kept at the same temperature for a further 3 hours and then cooled on ice. 4N hydrochloric acid was added to the resulting reaction mixture to adjust the pH to 5-6. Subsequently, chloroform extraction including insolubles was performed, and the chloroform layer was separated and dried over magnesium sulfate. Chloroform was distilled off and the residue was dissolved in a small amount of methylene chloride. This solution was subjected to silica gel column chromatography, and eluted with a mixed solution of hexane / ethyl acetate (4: 1; volume ratio) to obtain the desired product (compound (2)) (4.1 g; yield 50%). It was.
The ¹ H-NMR chart of the obtained compound (2) is shown in FIG. 9, and the mass spectrum is shown in FIG.

(2) Synthesis of 3-isopropyl-4-benzyloxybenzaldehyde [3-isopropyl-4-benzyloxybenzaldehyde; molecular weight: 254] (Compound (3)) Compound (2) synthesized in (1) (3.28 g; 0 0.02 mol), benzyl chloride (2.77 g; 0.022 mol) and potassium carbonate (4.14 g; 0.03 mol) were reacted in dimethylformamide (DMF; 20 ml) at 120 ° C. for 1 hour. The reaction mixture was allowed to cool, and purified water (100 ml) was added at room temperature. Subsequently, ethyl acetate extraction including insolubles was performed, and the ethyl acetate layer was separated, washed with water and brine, and dried over magnesium sulfate. Ethyl acetate was distilled off to obtain the desired product (compound (3)) (5.1 g; yield 90%) as a residue.

(3) Synthesis of 3-isopropyl-4-benzyloxycinnamic acid [3-isopropyl-4-benzyloxycinnamic acid; molecular weight: 296] (compound (4)) Compound (3) synthesized in (2) (2.54 g; 0.01 mol), malonic acid (1.25 g; 0.012 mol) and piperidine (100 mg) were reacted in pyridine (10 ml) at about 100 ° C. for 5 hours, and the mixture was ice-cooled. 2N hydrochloric acid was added to the resulting reaction mixture to adjust the pH to 1-2. Subsequently, ethyl acetate extraction including insolubles was performed, and the ethyl acetate layer was separated, washed with water and brine, and dried over magnesium sulfate. Ethyl acetate was distilled off to obtain the desired product (compound (4)) (2.07 g; yield 70%) as a residue.
FIG. 11 shows a ¹ H-NMR chart of the obtained compound (4).

(4) Synthesis of 3- (3-isopropyl-4-hydroxyphenyl) propionic acid [3- (3-isopropyl-4-hydroxyphenyl) propionic acid; molecular weight: 208] (compound (5)) (1) to (3 ) Was repeated, and the resulting compound (4) was united. Such compound (4) (2.96 g; 0.01 mol) was dissolved in 50 ml of a tetrahydrofuran (THF) / methanol mixture (5: 1; volume ratio). 10% palladium carbon catalyst (500 mg) was added to the resulting solution, and a hydrogenation reaction was performed under pressure (4 kg / cm ₂ ). After completion of the reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in a small amount of methylene chloride. This solution was subjected to silica gel column chromatography and eluted with a chloroform / methanol mixture (50: 1; volume ratio) to obtain the desired product (compound (5)) (1.87 g; yield 90%). .

The obtained compound (5) was a white needle crystal and was a single spot (Rf = 0.7) by thin layer chromatography on silica gel G (developing solvent: chloroform / methanol = 10/1). Further, a ¹ H-NMR chart of this compound is shown in FIG. 12, and a mass spectrum is shown in FIG.

(Example 4) Synthesis of 3-isopropyl-4-hydroxycinnamic acid [3-Isopropyl-4-hydroxycinnamic acid; molecular weight: 206] (Compound D) According to the reaction pathway shown in [Chemical Formula 6], Compound (2) From this, the target compound D (compound (6) (where R is an isopropyl group) in the reaction route diagram) was synthesized.

  3-Isopropyl-4-hydroxybenzaldehyde (1.64 g; 0.01 mol), acetic anhydride (4.0 g; 0.039 mol) and potassium carbonate (1.0 g) synthesized by the method described in Example 3 (1). 0.0075 mol) was reacted in an oil bath at 120-130 ° C. for 3 hours. After allowing to cool, distilled water (50 ml) was added to the reaction mixture. Thereafter, the solvent was distilled off under reduced pressure, and the residue was dissolved in a 10% aqueous sodium hydroxide solution (30 ml). In this state, the reaction was allowed to proceed for 2 hours at room temperature. To the resulting reaction mixture, 10% hydrochloric acid was added to adjust the pH to 2-3. Subsequently, chloroform extraction including insolubles was performed, and the chloroform layer was separated and dried over magnesium sulfate. Chloroform was distilled off under reduced pressure, and the residue was dissolved in a small amount of methylene chloride. This solution was subjected to silica gel column chromatography and eluted with a chloroform / methanol mixture (20: 1; volume ratio) to obtain the desired product (compound (6)) (0.8 g; yield 39%). .

The obtained compound (6) was a slightly colored crystal, and was a single spot (Rf = 0.4) by thin layer chromatography on silica gel G (developing solvent: chloroform / methanol = 10/1). Further, FIG. 14 shows a ¹ H-NMR chart of this compound, and FIG. 15 shows a mass spectrum thereof.

(Experimental Example 1) Effects of Compounds A and B of the Present Invention on Plant Growth The effect of compounds A and B on the growth of sprout (sprouts) was examined using radish, broccoli and mustard seeds.

(1) Experimental conditions Seeds: Seeds of radish radish 5.0 g / pod, broccoli 2.5 g / pod, and mustard 1.7 g / pod.
Test liquid: 0.1 mg, 1.0 mg or 10 mg of compound (A or B) was dissolved in 0.5 ml of dimethyl sulfoxide (DMSO). To this was added 99.5 ml of distilled water to prepare 100 ml of a test liquid. Therefore, the compound concentrations were 1 ppm, 10 ppm and 100 ppm. As a control, distilled water containing 0.5% by volume of DMSO was used.

(2) Cultivation method i) Seeds were immersed in distilled water overnight.
ii) A urethane holding plate was placed in a pod containing 100 ml of the test liquid, and the immersed seeds were sown on the holding plate. Three pods were prepared for each test liquid sample.
iii) The pod was allowed to germinate in a germination room (dark room; 23 ° C.) for 1 day (in the case of radish radish) or 2 days (in the case of broccoli and mustard), and then cultivated in a greenhouse in the sunlight.
iv) Five days after sowing, the degree of plant growth was measured.

(3) Measurement method and results (3-1) Hypocotyl length Three samples were collected from each pod. Therefore, 9 samples are collected for each test liquid specimen. For these samples, the length of the hypocotyl (sprout stem part) was measured.
The maximum value and the minimum value were excluded, and the average of the measured values of 7 samples was obtained.
The ratio of the measured value when each test liquid was used to the measured value of the control (this is assumed to be 100%) is shown in FIG. 16 (Kaiware Daikon), FIG. 17 (broccoli) and FIG. 18 (Mustard). .

(3-2) Fresh weight For each test liquid, collect all seeds in 3 pods (including those that have germinated and those that have not germinated; however, excluding samples for measuring hypocotyl length). The total weight was measured.
The ratio of the measured value when each test liquid was used to the measured value of the control (this is assumed to be 100%) is shown in FIG. 19 (Kaiware Daikon), FIG. 20 (broccoli) and FIG. 21 (Mustard). .

(3-3) Dry weight All samples whose fresh weight was measured were placed in a dryer at 90 ° C. After drying for 1 day, the weight was measured.
The ratio of the measured value when each test liquid was used to the measured value of the control (this is assumed to be 100%) is shown in FIG. 22 (Kaiware radish), FIG. 23 (broccoli) and FIG. 25 (Mustard). .

(Experimental Example 2) Effects of the compounds A, B, C and D of the present invention on the growth of plants Using lettuce seeds, the effects of the compounds A, B, C and D on the elongation of roots and the like were examined.

(1) Experimental conditions Seeds: Six lettuce seeds were used per specimen.
Test liquid: 0.01 mg, 0.1 mg, 1.0 mg or 10 mg of the compound (A, B, C or D) was dissolved in 0.5 ml of dimethyl sulfoxide (DMSO). To this was added 99.5 ml of distilled water to prepare 100 ml of a test liquid. Accordingly, the compound concentrations were 0.1 ppm, 1 ppm, 10 ppm and 100 ppm. As a control, distilled water containing 0.5% by volume of DMSO was used. In addition, as a reference example, an experiment was also performed when only distilled water was used.

(2) Cultivation method i) 2.5 ml of the test solution was added to a petri dish laid with filter paper (No. 1).
ii) Six lettuce germinating seeds (root end: about 3 mm) were arranged on the filter paper so that the intervals were uniform.
iii) The petri dish was covered and left in the germination room (dark room; 23 ° C.) for 1 day.

(3) Measurement method and results For each seed, the root elongation length was measured and the average value was determined. FIG. 25 shows the ratio of the measured value when each test liquid was used to the measured value of the control (this is assumed to be 100%). All compounds acted as growth inhibitors when the concentration was 100 ppm.

  The novel compound according to the present invention can be used as a plant growth regulator.

Claims (9)

3- (3-tertiaryamyl-4-hydroxyphenyl) propionic acid represented by the following formula A.

3-tertiaryamyl-4-hydroxycinnamic acid represented by the following formula B.

3- (3-Isopropyl-4-hydroxyphenyl) propionic acid represented by the following formula C.

3-Isopropyl-4-hydroxycinnamic acid represented by the following formula D.

A plant growth regulator comprising at least one of the compounds according to claims 1 to 4. A process for producing 3- (3-tertiaryamyl-4-hydroxyphenyl) propionic acid or 3- (3-isopropyl-4-hydroxyphenyl) propionic acid through the following steps (I) to (III):
(I) a step of introducing a protecting group into a phenolic hydroxyl group of a phenol having an aldehyde group at the para position and a substituent at the ortho position (provided that the substituent is a tertiary-amyl group or an isopropyl group);
(II) a step of converting an aldehyde group into an acrylic acid group; and (III) a step of removing the protecting group and hydrogenating the acrylic group. Further, in order to obtain a phenol having an aldehyde group at the para position and a substituent at the ortho position (provided that the substituent is a tertiary amyl group or an isopropyl group), the substituent is used at the meta position. The 3- (3-tertiaryamyl-4-hydroxyphenyl) propionic acid or 3- (3-isopropyl-4-hydroxy) according to claim 6, wherein the step of introducing an aldehyde group into the para-position of the phenol having A method for producing phenyl) propionic acid. A process for producing 3-tertiaryamyl-4-hydroxycinnamic acid or 3-isopropyl-4-hydroxycinnamic acid, which undergoes the following step (i):
(I) A step of converting an aldehyde group of a phenol having an aldehyde group at the para position and a substituent at the ortho position (wherein the substituent is a tertiaryamyl group or an isopropyl group) into an acrylic acid group. Further, in order to obtain a phenol having an aldehyde group at the para position and a substituent at the ortho position (provided that the substituent is a tertiary-amyl group or an isopropyl group) used in the step (i), the substituent at the meta position is used. The method for producing 3-tertiaryamyl-4-hydroxycinnamic acid or 3-isopropyl-4-hydroxycinnamic acid according to claim 8, wherein the step of introducing an aldehyde group into the para-position of the phenol having N is carried out.

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