WO2002007517A1

WO2002007517A1 - Plant ethylene biosynthesis inhibitors

Info

Publication number: WO2002007517A1
Application number: PCT/JP2001/006256
Authority: WO
Inventors: Nobuaki Mito; Noritada Matsuo; Michihiko Fujinami
Original assignee: Sumitomo Chemical Company, Limited
Priority date: 2000-07-21
Filing date: 2001-07-18
Publication date: 2002-01-31

Abstract

It is found out that compounds (I) represented by the following general formula (I) or agriculturally acceptable salts thereof are usable as the active ingredient of plant growth regulators because of having an effect of inhibiting the biosynthesis of ethylene in plants: (I) wherein R represents C4-10 hydrocarbyl. The compounds (I) or agriculturally acceptable salts thereof are particularly usable in preventing fruits from dropping, preventing cotton balls, flowers and young flower buds from dropping, maintaining the freshness of fruits, cut flowers and vegetables, etc.

Description

Plant ethylene biosynthesis inhibitors

The present invention relates to an inhibitor of ethylene biosynthesis in a plant. Background art

Ethylene is a plant hormone involved in biomechanism such as promoting plant maturation. Specifically, the physiological effects of ethylene have been known to promote senescence of plantlets, promotion of fruit ripening, promotion of chlorophyll decomposition, promotion of delamination, etc. [“Plant hormones” (Yasuyuki Katsumi, 199 1 year), "Life of Plants and Ethylene" (Yasuo Ota, 1980, Tokai University Press). ]. Under these circumstances, by controlling ethylene biosynthesized in the plant, it is possible to control plant aging and ripening and to maintain the freshness of fruits, vegetables, cut flowers, etc. There has been extensive research on controlling ethylene as a powerful technique. As a method for controlling the biosynthesis of ethylene in a plant, there is a method of inhibiting the biosynthesis of ethylene by applying a chemical substance to a plant. Examples of such a biosynthesis inhibitor include rhizobitoxin and the like. Chemical substances such as plant toxins, heavy metals such as mercury and silver are known. However, these known ethylene biosynthesis inhibitors are not always sufficient in various target plants and various use situations, and new ethylene biosynthesis inhibitors are required. Invention of invention

The present inventors have intensively searched for a novel ethylene biosynthesis inhibitor, and found that the following formula (I)

[Wherein, R represents a hydrocarbon group having 4 to 10 carbon atoms. ]

The compound (I) or an agriculturally acceptable salt thereof represented by the formula (I) has an excellent ethylene biosynthesis inhibitory activity and is therefore useful as an active ingredient of a plant growth regulator. Was completed.

That is, the present invention relates to various uses of compound (I) or an agriculturally acceptable salt thereof (hereinafter, referred to as the compound of the present invention) capable of inhibiting ethylene biosynthesis in a plant. is there. -Owl-shaped bear for invention

The compound of the present invention is specifically used by the method shown below.

During the fruit ripening process, ethylene that is biosynthesized in the plant accelerates the formation of delamination. If delamination is completed before the optimal harvest time of the fruit, the fruit will fall to the ground before the optimal harvest time and will significantly impair the quality of the fruit. By applying the compound of the present invention to the fruits and branches and leaves in the maturation process, the biosynthesis of ethylene in the plant is inhibited, so that delamination formation by ethylene is suppressed, and as a result, the falling of the fruits is prevented. Can be suppressed.

In addition, the compound of the present invention is used to inhibit the fall of plants, the fall of young buds and the fall of poles such as cotton by the ethylene biosynthesis inhibitory effect of the compound of the present invention. It can be processed into poles such as flowers, buds or cotton. Cut flowers of flowers and the like are exposed to various stresses in the transportation process. When ethylene is biosynthesized in the plant in response to this stress, aging is promoted and the commercial value is reduced. By treating the cut flowers of flowers with the compound of the present invention, the biosynthesis of ethylene in the cut flowers is inhibited, and the freshness of the cut flowers can be maintained. The fruit is resistant to external physical damage before and immediately after harvest (the resistance to physical damage can be expressed by the firmness of the fruit as measured by a hardness tester, Hardness is generally considered as a measure of fruit freshness.) However, fruit hardness generally decreases during preservation of fruits after harvest. The decrease in hardness is thought to be indirectly due to ethylene biosynthesized in the fruit. It is thought that by applying the compound of the present invention to fruits before and / or immediately after harvesting, ethylene biosynthesis inside the fruits is inhibited, and it is possible to maintain the freshness of fruits after harvesting. Can be

Similarly, the compounds of the present invention are also effective for maintaining the freshness of vegetables after harvesting.

Plants to be treated with the compound of the present invention include, for example,

Ornamental plants such as flowers and houseplants [Specifically, carnations and the like can be mentioned. ]

Crops such as cereals, vegetables, fruit trees, etc. [Specifically, stones such as pears such as kiyabetto, broccoli, apples and pears, 祧, cherry, apricot, olive, plum, nectarine, pulp, almonds Fruits, varieties, citrus fruits such as lemon, Unshu mandarin orange, grapefruit, lime, berries, grapes, tomatoes and the like. ]

Textile plants [Specifically, cotton and the like can be mentioned. ]

Trees,

Turf and the like.

The compound of the present invention is usually mixed with an inert carrier such as a solid carrier or a liquid carrier, and if necessary, added with a surfactant and other pharmaceutical auxiliaries to prepare an emulsion, a wettable powder, a suspending agent, It is formulated into a water solvent and used. In these preparations (hereinafter referred to as the agent of the present invention), the compound of the present invention is generally contained in an amount of 0.5 to 90% by weight, preferably 1 to 80% by weight.

Examples of the solid carrier used in the formulation include clays (such as clay olinate, diatomaceous earth, synthetic hydrous silicon oxide, fubasami clay, bentonite, and acid clay), talc, and other inorganic minerals (sericite, quartz powder, sulfur powder). , Activated carbon, Examples include fine powders and granular materials such as chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea, etc.). Liquid carriers include, for example, water, alcohols (methanol, ethanol, etc.), ketones. (Acetone, methylethylketone, cyclohexanone, etc.), aromatic hydrocarbons (toluene, xylene, ethylbenzene, methylnaphthalene, etc.), non-aromatic hydrocarbons (hexane, cyclohexane, kerosene, etc.) , Esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (dioxane, diisopropyl ether, etc.), acid amides (dimethylformamide, dimethylacetamide, etc.), Examples include halogenated hydrocarbons (dichloroethane, trichloroethylene, etc.). Is Ru.

Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyethylene glycol ethers, polyhydric alcohol esters, And sugar alcohol derivatives.

Other pharmaceutical auxiliaries include, for example, casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid) Fixing agents and dispersants such as PAP (isopropyl oxyphosphate), BHT (2,6-tert-butyl-4-methylphenol), BHA (2- / 3-tert-butyl-4-methoxyphenol) And stabilizers such as vegetable oils, mineral oils, fatty acids and fatty acid esters.

The compound of the present invention is thus formulated and treated as it is or diluted with water or the like to the target plant. The compound of the present invention may be applied to growing plants or may be applied to harvested plants. Examples of the treatment method include spraying treatment, dipping treatment, water absorption treatment, and coating treatment. The compound of the present invention is applied to a portion suitable for treatment, such as a foliage, a branch, a flower, a fruit, or the like of a plant. In addition, the compound of the present invention is treated once or plural times with respect to a target plant.

When the compound of the present invention is used for the purpose of suppressing the falling of fruit, the compound of the present invention is usually used. The agent is diluted in water and applied to the fruit and branches of the fruit tree before harvesting.

When the compound of the present invention is used for the purpose of suppressing the fall of cotton poles, the agent of the present invention is usually diluted in water and sprayed on cotton poles and foliage before harvesting.

When the compound of the present invention is used for the purpose of maintaining the freshness of cut flowers, the agent of the present invention is usually diluted with water and the cut flowers absorb water. Further, the agent of the present invention may be added to water in a vase containing cut flowers, or the agent of the present invention may be diluted with water and sprayed on cut flowers.

When the compound of the present invention is treated for the purpose of maintaining the freshness of fruits and vegetables, the agent of the present invention is diluted with water and sprayed on the edible portion of the harvested fruits or vegetables, Immerse the edible part.

When the compound of the present invention is treated for the purpose of suppressing the fall of flowers and the fall of young buds, the agent of the present invention is diluted with water and sprayed on the foliage and flowers or young buds of a flowering plant. You.

The application rate of the compound of the present invention in the present invention may vary depending on the formulation form, application time, application method, application place and target plant, but is usually 1 to 8000 g, preferably 10 to 1000 g per hectare. is there. The concentration of the compound of the present invention when the agent of the present invention is used after being diluted with water may vary depending on the form of the preparation, the time of application, the method of application, the place of application, and the target plant. 100100 OmM, preferably 0.001 to 10 mM, more preferably 0.01 to 10 mM.

In the present invention, the hydrocarbon group having 4 to 10 carbon atoms represented by R in the formula (I) includes a C4 to C10 alkyl group (specifically, a butyl group, a 1-methylpropyl group (s_butyl group) ), Pentyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group (isopentyl group), 2,2-dimethylpropyl group (neopentyl group), hexyl group, 1-methylpentyl group, 2-methylpentyl group , 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, and heptyl. ], A C4-C10 alkenyl group (specifically, Examples thereof include a 3-butenyl group, a 4-pentenyl group, a 3-methyl-3-butenyl group, and a 3-methyl-2-butenyl group. A C4-C10 alkynyl group [Specific examples include a 3-butynyl group and a 2-methyl-3-butynyl group. ], A C4-C10 cycloalkyl group [Specific examples include a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. A C4-C10 (cycloalkylalkyl) group [Specific examples include a cyclopropylmethyl group, a 2-cyclopropylethyl group, a cyclopentylmethyl group, and a cyclohexylmethyl group. A C7-C10 (phenylalkyl) group [specifically, a benzyl group, a 2-phenylethyl group (a phenethyl group) and the like. And the like.

Compound (I) can be produced, for example, according to the method described in JP-A-51-19126, International Patent Application Publication No. WO 97/35565, or Phytochemistry 1975, Vol.

Specifically, the following scheme

4-hid

Roxy-1 6-methyl-2-pyrone

[Wherein, R represents the same meaning as above, X represents a group represented by a chlorine atom, a hydroxyl group or the formula RC0 _2. ]

Can be produced by the method shown in

In the formula (II), when X is a chlorine atom, the reaction is carried out by reacting 4-hydroxy-6-methyl-2-pyrone with a compound represented by the formula (II) in the presence of an acid. . The compound represented by the formula (II) is usually used in an amount of 1 to 2 mol per 1 mol of 4-hydroxy-6-methyl_2-pyrone. Examples of the acid include an organic acid such as trifluoroacetic acid.

In the formula (II), when X is a hydroxyl group, the reaction is to react 4-hydroxy-6-methyl-2-pyrone with the compound represented by the formula (II) in a solvent in the presence of a condensing agent. It is performed by The compound represented by the formula (II) Usually 1 to 2 mol is used per 1 mol of hydroxy-6-methyl-2-pyrone. Examples of the condensing agent include dialkyl carbodiimides such as dicyclohexyl carbodiimide.

In addition, a commercially available product can be used for 4-hydroxy-16-methyl-2-pyrone.

The agriculturally acceptable salt of compound (I) can be produced by a usual method. Specifically, compound (I) is reacted with a base (eg, sodium hydroxide, sodium ethoxide, isopropylamine, etc.) in a solvent (eg, water, methanol, ethanol, acetone, ethyl acetate, etc.). Then, by distilling off the solvent, a salt of compound (I) can be produced.

Examples of the salt include a sodium (Na) salt obtained by reaction with sodium heptaoxide, sodium ethoxide, and the like, and an isopropylamine salt obtained by reaction with isopropylamine.

Hereinafter, the present invention will be described in more detail with reference to Synthesis Examples of the compound of the present invention, Formulation Examples of the agent of the present invention, and Test Examples, but the present invention is not limited to only these examples.

First, a synthesis example is shown.

Synthesis example 1

4-Hydroxy-6-methyl-2-pyrone 10. O g (79.3 mmo 1) is suspended in 100 ml of toluene at room temperature, and 1.22 g (10. Ommo 1) of N, N-dimethylaminopyridine, isocaprone 10.0 g (86. lmmo 1) of the acid and 18.5 g (89.7 mmo 1) of dicyclohexylcarposimide were sequentially added. The mixture was stirred at room temperature for 1 hour, then heated to 70 and heated and stirred for 20 hours did. After returning to room temperature, the resulting insoluble dicyclohexylurea was separated by filtration, and washed once with 1N aqueous hydrochloric acid and twice with 10% saline. The organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude oil.

The crude oil was subjected to silica gel column chromatography (eluent: hexane Z-ethyl acetate = 6/1) to give Compound [4] 7.1 1 (40% yield). Compound [4] (R = 3-methylbutyl group)

mp.: 42 ° C

'H-NMRCCDClg / TMS): 0.94 (6H, d), 1.54 (2H, q), 1.63 (1H, m), 2.27 (3H, s), 3.08 (2H, t), 5.93 (1H, s), 17.88 (1H, s)

Synthesis example 2

Dissolve 2.0 g (15.9 mmo 1) of 4-hydroxy-6-methyl-2-pyrone in 3 Om 1 of trifluoroacetic acid and add 2.69 g of 2-methylvaleric acid chloride

(20. Ommol) was added, and the mixture was heated under reflux for 1 hour. The solvent was distilled off under reduced pressure, ethyl acetate was added to the residue, and the mixture was washed three times with 10% saline. The organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain an oil. The oil was subjected to silica gel column chromatography (developing solvent: hexane Z ethyl acetate = 6Z1) to obtain 1.06 g of the compound [2] (30% yield). Compound [2] (R = l-methylbutyl group)

mp.: 66 ° C

1 H-NMR (CDCI3 / TMS): 0.90 (3H, t), 1.15 (3H, d), 1.33 (3H, m), 1.75 (1H, m), 2.27 (3H, s), 3.92 (1H, m ), 5.94 (1H, s), 17.75 (1H, s) Synthesis example 3

1.0 g (4.5 mmo 1) of the compound [4] was dissolved in 10 ml of ethanol at room temperature, and 1.1 g (4.5 imol) of a 28% sodium ethoxide / ethanol solution was added. After stirring this mixture at room temperature for 1 hour, the solvent was distilled off under reduced pressure to obtain 1.05 g of the compound [11] (yield 9.5%).

Compound [11] (R == 3-methylbutyl group, sodium salt)

¹ H-NMR (CDClj / TMS): 0.90 (6H, d), 1.45 (2H, m), 1.60 (1H, m), 2.04 (3H, s), 2.95 (2H, dd), 5.60 (1H, s)

Synthesis example 4

1.0 g (4.5 mmo 1) of compound [4] was dissolved in 10 ml of ethyl acetate at room temperature, and 0.26 g (4.5 mmo 1) of isopropylamine was added. After stirring this mixture at room temperature for 1 hour, the solvent was distilled off under reduced pressure to obtain 1.12 g of the compound [12] (yield 87%).

Compound [1 2] (R = 3-methylbutyl group, isopropylamine salt)

_{1 H-NMR (CDC1 3 /} TMS): 0.91 (6H, d), 1.20 (6H, d), 1.47 (2H, m), 1.59

(1H, m), 2.12 (3H, s), 2.95 (2H, dd), 3.28 (1H, m), 5.68 (1H, s)

The compound (I) produced according to the method described in any of Synthesis Examples 1 to 4 and the physical properties together with the compound number are shown below.

Compound (3) (R = 2-methylbutyl group)

Property: oil

n _D: 1.522 / 23 ° C

1 H-NMR (CDCI3 / TMS): 0.94 (6H, m), 1.35 (2H, m), 2.01 (1H, m), 2.27 (3H, s), 2.94 (2H, m), 5.93 (1H, s ), 17.24 (1H, s)

Compound [5] (R = 2,3-dimethylbutyl group)

mp .: 49 ° C

¹ H-NMR (CDCI3 / TMS): 0.88 (9H, m), 1.65 (1H, m), 2.03 (1H, m), 2.26 (3H, s), 3.00 (2H, m), 5.92 (1H, s ), 17.11 (1H, s)

Compound [6] (R: 3,3-dimethylbutyl group)

Immediately.: 61 ° C

¹ H-NMR (CDCI3 / TMS): 0.95 (9H, s), 1.55 (2H, t), 2.27 (3H, s), 3.05 (2H, t), 5.93 (1H, s), 17.44 (1H, s) )

Compound [7] (R: heptyl group)

mp .: 66. C

¹ H-NMR (CDCI3 / TMS): 0.90 (3H, t), 1.29 (8H, m), 1.68 (2H, m), 2.28 (3H, s), 3.08 (2H, i), 5.91 (1H, s ), 17.75 (1H, s) Compound [8] (R: 3-butenyl group)

Immediately: 193 ⁰ C

^{1 H-NMR (CDClg / TMS} ): 1.99 (1H, s), 2.30 (3H, s), 2.58 (2H, t), 3.37 (2H, t), 5.97 (1H, s), 17.67 (1H, s )

Compound [9] (R: 2-cyclopropylethyl group)

Immediately: 71 ° C

¹ H-NMR (CDCI3 / TMS): 0.08 (2H, m), 0.44 (2H, 1), 0.80 (1H, m), 1.57 (2H, q), 2.27 (3H, s), 3.19 (2H, t ), 5.94 (1H, s), 16.85 (1H, s) compound [10] (R: cyclohexylmethyl group)

Immediately: 52 ° C

^{_{1 H-NMR (CDC1 3 /}} TMS): 1.09 (2H, m), 1.25 (3H, m), 1.74 (5H, m), 1.90 (1H, m), 2.28 (3H, s), 2.98 (2H, d), 5.95 (1H, s), 17.02 (1H, s)

Next, formulation examples are shown. In the following examples, parts represent parts by weight.

Formulation Example 1

50 parts of the compound [4], 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. Formulation Example 2

70 parts of the compound [10], 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 25 parts of synthetic hydrous silicon oxide are well ground and mixed to obtain a wettable powder.

Formulation Example 3

40 parts of compound [6], 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 52 parts of water are mixed and wet-milled until the particle size becomes 5 microns or less. Get.

Formulation Example 4

40 parts of compound [9], 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 52 parts of water are mixed and wet-milled until the particle size becomes 5 microns or less, and suspended. Get the agent. Next, the present invention will be described in detail with reference to test examples, but the present invention is not limited to these examples.

Test example 1

Yaenari (black pine bean) seeds were evenly sown on vermiculite containing a suitable amount of water, and grown at 25 degrees Celsius in the dark for 4 days to obtain yellowed seedlings. A hypocotyl section of 10 mm was prepared from immediately below the hook of the yellowed plant. The 10 hypocotyl sections were subjected to 5 OmM phosphate buffer containing the test compound at a predetermined concentration and 0. ImM 2,4-dichlorophenoxyacetic acid (hereinafter referred to as 2,4-D). The solution (pH 6.8) was placed in a 1 Oml vial together with 0.5 ml and sealed with a silicon stopper. After incubating this at 25 ° C for 6 hours at a location, the ethylene concentration in the gas phase was measured by gas chromatography to calculate the amount of ethylene generated. Table 1 shows the results. Note that “Control-1” in Table 1 used the test compound and 5 OmM phosphate buffer containing neither 2,4-D, and “Control_2” did not contain the test compound. 0. A 5 OmM phosphate buffer containing 2,4-D of ImM was used. The amount of ethylene generation in Table 1 is a relative value with the amount of ethylene generation (nlZlO intercept) in “Control_2” being 100.

【table 1】

Test example 2

Yaenari (black pine bean) seeds were evenly sown in bamboo mullite containing a suitable amount of water, and cultivated at 25 ° C for 4 days in different places to obtain yellowed seedlings. A hypocotyl section of 1 Omm was prepared directly below the hook of the yellowed plant. 10 hypocotyl sections, A 5 OmM phosphate buffer (pH 6) containing a test compound at a predetermined concentration (described in Table 2) and 0.5 mM of 1-aminocyclopropane-1-1 rubonic acid (hereinafter referred to as ACC). 8) The mixture was placed in a 10 ml vial with 0.5 ml, and sealed with a silicon stopper. After incubating this in the dark at 25 degrees Celsius for 6 hours, the ethylene concentration in the gas phase was measured by gas chromatography to calculate the amount of ethylene generated. Table 2 shows the results.

In Table 2, “Control-1” used a 5 OmM phosphate buffer containing neither the test compound nor AC C, and “Control-1” did not contain the test compound but AC C. A 5 OmM phosphate buffer containing the following was used. In addition, the amount of ethylene generated in Table 2 is a relative value when the amount of ethylene generated (n 1/10 intercept) in “Control-2” is 100.

[Table 2]

Test compound Test compound concentration ACC concentration Ethylene generation

(mM) (mM) (relative value)

Control—1 0

Control 1 2 0.5 0.5 100

Dehydroacetic acid 0.5 0.5 0.5 49

Compound [2] 0.5 0.5 13

Compound [3] 0.1 0.5 6

Compound (4) 0.5 0.5 0.5 11

Compound [5] 0.5 0.5 3

Compound [6] 0.5 0.5 6

Compound [7] 0.5 0.13

Compound [8] 0.5 0.5 2

Compound [9] 0.5 0.5 0.5 9

Compound (10) 0.5 0.5 0.5 4 Test example 3

Using the test compounds described in Table 3, the ethylene concentration in the gas phase was measured in the same manner as in Test Example 2, and the amount of generated ethylene was calculated.

Note that “Control-1” in Table 3 uses a 5 OmM phosphate buffer solution containing neither the test compound nor AC C, and “Control-1” does not contain the test compound but ACC. 5 OmM phosphate buffer. In addition, the amount of ethylene generated in Table 2 is a relative value when the amount of ethylene generated (nlZlO intercept) in “Control-2” is 100.

[Table 3]

Test example 4

Tomatoes were cultivated in a greenhouse, and unripe tomato fruits with a diameter of about 2 cm were harvested. The specified amount of the emulsion obtained by thoroughly mixing 4 parts of the test compound, 16 parts of Solpol 2680X (trade name of Toho Chemical Industry Co., Ltd.) and 80 parts of cyclohexanone was used as the sieve L-77 (Lovel and Indus tries). It was diluted with 16 ml of water containing 0.25% and sprayed on 10 tomatoes with a small sprayer. Thereafter, the tomatoes were placed in a plastic container having a diameter of 12 cm and a height of 8.5 cm, and the tomatoes were ripened at 25 ° C in places. The degree of ripening of the tomato was determined by the color of the tomato. The following index was used as a standard for the color of tomato. 1: The whole tomato fruit is green

2: A part of tomato fruit turns light red

3: About 50% of tomato fruit turns red

4: 80% of tomato fruit turns red

5: The whole tomato fruit turns red

This test was performed three times. Table 4 shows the results. The results are shown as the average of the judgment results of 10 tomato fruits.

[Table 4]

Industrial availability

Since the compound of the present invention can inhibit ethylene biosynthesis in a plant, it suppresses fruit dropping of fruit trees, suppresses the fall of cotton poles, flowers, and young buds, and maintains the freshness of fruits, cut flowers, and vegetables. Can be used for adjustment purposes.

Claims

The scope of the claims

[Wherein, R represents a hydrocarbon group having 4 to 10 carbon atoms. ]

A plant ethylene biosynthesis inhibitor comprising, as an active ingredient, a compound (I) represented by the formula (I) or an agriculturally acceptable salt thereof.

2. A plant growth regulator comprising the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as an active ingredient.

3. An agent for inhibiting fruit dropping of a fruit tree, comprising the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as an active ingredient.

A cotton pole fall inhibitor containing the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as an active ingredient.

5. A preservative for freshness of cut flowers, comprising the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as an active ingredient.

6. A freshness preserving agent for fruits or vegetables containing the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as an active ingredient.

7. A plant flower fall inhibitor comprising the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as an active ingredient.

8. An agent for inhibiting fall of a young bud of a plant, comprising the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as an active ingredient.

9. A method for inhibiting etylene biosynthesis in a plant, comprising treating a plant with an effective amount of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof.

10. Effect of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof A plant growth regulation method in which the amount is applied to plants.

1 1. A method for suppressing fruit dropping of fruit trees, which comprises spraying an effective amount of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof on fruit and branches of the fruit tree.

12. A method for suppressing the fall of a cotton pole, which comprises spraying an effective amount of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof on the cotton pole and foliage.

13. A method for maintaining the freshness of cut flowers, comprising treating cut flowers with an effective amount of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof.

14. A method for preserving the freshness of fruits or vegetables, wherein an effective amount of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof is applied to edible parts of fruits or vegetables after harvesting.

15. A method for suppressing falling of a flower of a plant, comprising spraying an effective amount of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof on the foliage and flowers of the flowering plant.

16. A method for suppressing fall of a young bud of a plant, which comprises spraying an effective amount of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof on the foliage and the young bud of the flower plant.

17. Use of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as an inhibitor of ethylene biosynthesis in a plant.

18. Use of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as a plant growth regulator.

19. Use of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as a fruit dropping inhibitor for fruit trees.

20. Use of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as a cotton pole fall inhibitor.

2 1. Use of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as an agent for maintaining freshness of cut flowers.

22. Use of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as an agent for preserving the freshness of fruits or vegetables.

23. The plant of compound (I) of claim 1 or an agriculturally acceptable salt thereof. Use as a flower fall inhibitor for objects.

24. Use of the compound (I) according to claim 1 or an agriculturally acceptable salt thereof as an agent for suppressing falling of buds of a plant.