WO2007102615A1

WO2007102615A1 - Plant growth promoter

Info

Publication number: WO2007102615A1
Application number: PCT/JP2007/054753
Authority: WO
Inventors: Noritada Matsuo; Asako Nagasawa; Masayuki Mae
Original assignee: Sumitomo Chemical Company, Limited
Priority date: 2006-03-07
Filing date: 2007-03-06
Publication date: 2007-09-13
Also published as: JP2007238476A

Abstract

Because of having an excellent effect of promoting plant growth, a butenolide compound represented by the formula (I) is useful as the active ingredient of a plant growth promoter. By applying the compound represented by the formula (I) to a plant or a place where a plant grows, the growth of the plant can be promoted.

Description

Descriptions Plant Growth Accelerator Technical Field

The present invention relates to a butenolide compound represented by the following formula (I), a plant growth promoting use thereof, and a production intermediate thereof. Background art

Known methods for initiating bud development of dormant seed plants, that is, germination promotion methods include ethylene chlorohydrin hydrogen cyanide gas treatment and alcohol Z organic acid treatment chemical treatment method, warm bath method, and cooling method. ing. In particular, for seeds with hard seed coats and poor water permeability, a method of promoting germination by damaging the seed coats with sulfuric acid or mechanically or by baking is known.

— On the other hand, certain compounds with 2 H-Furo [2,3-c] pyran-2-one structure have a germination-promoting effect. Science, Vol. 3 05, No. 13, No. 9, 7 7 (2 0 4 4 years) and WO 2 0 0 5/0 6 1 5 1 5. Disclosure of the invention

The present invention provides a compound having a plant growth promoting effect.

The present invention is based on the finding that the butenolide compound represented by the following formula (I) has a plant growth promoting effect.

That is, the present invention provides the formula (I)

And a plant growth promoter comprising the same as an active ingredient, and a plant growth promoting method for applying the same to a plant or a plant growth site. The present invention also relates to a compound of formula (II), which is an intermediate for producing a sulfonyl compound represented by formula (I).

And a compound represented by

Formula (III)

It also provides the compound shown by these.

The butenolide compound represented by the formula (I) and the compound represented by the formula (III) both have stereoisomers related to the asymmetric carbon of the condensed ring portion. And mixtures of isomers in any proportion. Further, the compound represented by the formula (II) has stereoisomers related to two asymmetric carbon atoms, ie, a carbon atom to which a condensed ring moiety and a bromine atom are bonded. And any proportion of isomer mixtures. First, a method for producing a butenolide compound represented by the formula (I) will be described.

(Production method Α)

The butenolide compound represented by the formula (I) can be produced, for example, by reacting the compound represented by the formula (II) with a tertiary amine.

(Π) (I)

The reaction is usually performed in the presence of an organic solvent.

Examples of the organic solvent used in the reaction include ethers such as tetrahydrofuran and 1,4-dioxane. Examples of tertiary amines used in the reaction include 1,8-diazabicyclo [5. 4. 0] undecar 7-en and 1,5-diazabicyclo [4. 3. 0] noner 5 one. The amount used is usually 1 to 5 moles per mole of the compound represented by formula (II).

The reaction temperature is usually in the range of 0 to 100 ° C, and the reaction time is usually in the range of 1 to 48 hours.

After completion of the reaction, for example, the butenolide compound represented by the formula (I) can be isolated by mixing the reaction mixture with water, extracting with an organic solvent, and concentrating. The isolated butenolide compound represented by the formula (I) can be further purified by recrystallization, chromatography or the like.

Next, a method for producing the compound represented by the formula (II) and the compound represented by the formula (III) will be described.

(Production method B)

The compound represented by the formula (II) can be produced, for example, by reacting the compound represented by the formula (III) with a brominating agent in the presence of a radical generator.

(III) (Π)

The reaction is usually performed in an organic solvent.

Examples of the organic solvent include nitriles such as acetonitrile and propionitrile.

Examples of the brominating agent include 1,3-dib-mouthed 5,5-dimethylhydansine, and examples of the radical generator include benzoyl peroxide. These are used in an amount of usually 1 to 5 mol of brominating agent and 0.05 to 0.3 mol of radical generator, based on 1 mol of the compound represented by formula (III). The reaction temperature is usually in the range of 0 to 150 ° C, and the reaction time is usually in the range of 1 to 24 hours. After completion of the reaction, for example, the compound represented by the formula (II) can be isolated by concentrating the reaction mixture as it is, or by mixing the reaction mixture with water or the like, extracting with an organic solvent, and concentrating. . The isolated compound represented by the formula (II) can be further purified by recrystallization, chromatography, etc.

(Production method C)

The compound represented by the formula (III) can be produced, for example, by reacting a compound represented by the following formula (IV) with a tertiary amine.

(IV) (HI)

[Wherein X represents a bromine atom or an iodine atom. ]

The reaction is usually performed in the presence of an organic solvent.

Examples of the organic solvent include ethers such as tetrahydrofuran and 1,4-dioxane.

Examples of tertiary amines include 1,8-diazabicyclo [5. 4. 0] Wunde force _7—en and 1,5-diazabicyclo [4. 3. 0] nona 5-en. The amount used is usually 1 to 5 moles per mole of the compound represented by the formula (IV).

The reaction temperature is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 1 to 48 hours.

After completion of the reaction, for example, the compound represented by the formula (III) can be isolated by mixing the reaction mixture with water, extracting with an organic solvent, and concentrating. The isolated compound represented by the formula (III) can be further purified by recrystallization, chromatography or the like.

The compound represented by the formula (IV) used for producing the compound represented by the formula (III) can be produced, for example, by the following scheme.

(V-l) (V-2) (IV)

[Wherein, R ¹ and R ² each represent a methyl group or an ethyl group, and X represents the same meaning as described above. ]

(Process D-1)

The compound represented by the formula (VI-1) and the compound represented by the formula (VI-2) are prepared by combining the compound represented by the formula (VII) and the compound represented by the formula (VIII) in the presence of a base. It can be produced by reacting.

The reaction is usually performed in a solvent in the presence of a base.

Examples of the solvent include acid amides such as dimethylformamide and dimethylacetamide.

Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride, and the amount used is usually 1 to 3 moles per mole of the compound represented by the formula (VII). . The amount of the compound represented by the formula (VI II) is usually 1 to 3 moles per 1 mole of the compound represented by the formula (VII).

After completion of the reaction, for example, the reaction mixture is mixed with water, extracted with an organic solvent, and concentrated to concentrate the compound represented by the formula (VI-1) and / or the compound represented by the formula (VI-2). Product can be isolated. The isolated compound represented by the formula (VI-1) and The compound represented by the formula (VI-2) can be further purified by chromatography or the like.

(Process D-2)

The compound represented by the formula (V-1) and / or the compound represented by the formula (V-2) hydrolyzes the compound represented by the formula (VI 1 1) and / or the compound represented by the formula (VI-2). In general, it can be produced by reacting a compound represented by the formula (V-1) and / or a compound represented by the formula (V-2) with a base in a solvent. Examples of the solvent include methanol, ethanol, propanol, butanol, alcohols such as ethylene glycol and propylene glycol, water, and mixtures thereof.

As the base, for example, alkaline metal hydroxides such as hydroxylated lithium and sodium hydroxide can be used. The amount of the base used is a compound represented by the formula (VI-1) and the formula (IV-2) The amount is usually 1 to 3 moles per mole of the compound represented by

The reaction temperature is usually in the range of 0 to 250 ° C, and the reaction time is usually in the range of 1 to 24 hours.

After completion of the reaction, for example, the reaction mixture is mixed with an aqueous acid solution such as hydrochloric acid, extracted with an organic solvent, and concentrated to give a compound represented by the formula (V-1) and / or the formula (V-2). The compound to be isolated can be isolated. The isolated compound represented by the formula (V-1) and compound represented by the formula (V-2) can be further purified by chromatography or the like.

(Process D-3)

The compound represented by the formula (IV) can be produced by reacting the compound represented by the formula (V-1) and Z or the compound represented by the formula (V-2) with a brominating agent or an iodinating agent. it can.

The reaction is usually performed in an organic solvent.

Examples of the organic solvent include halogenated hydrocarbons such as black mouth form, dichloromethane, and 1,2-dichloro mouth ethane.

Examples of the brominating agent or iodinating agent include simple halogens such as bromine and iodine. The reaction temperature is usually in the range of 0 to 100 ° C, and the reaction time is usually in the range of 1 to 120 hours.

After completion of the reaction, for example, the compound represented by the formula (IV) can be isolated by mixing the reaction mixture with water or the like as necessary, followed by extraction with an organic solvent and concentration. The compound represented by the formula (IV) can be further purified by chromatography or the like.

The butenolide compound represented by the formula (I) can be used to promote growth at each stage of plant growth. Specific examples thereof include the promotion of germination and improvement of germination rate in the seed germination stage when the plant is a seed plant, the promotion of flowering and fruiting in the flowering stage and the fruiting stage in various plants, and Examples include breaking dormancy in the reproductive growth stage or vegetative growth stage. Another example is the promotion of proliferation in somatic embryo culture.

Examples of plants in which the butenolide compound represented by the formula (I) is effective include smoke-responsive plants; ornamental plants such as flower buds and foliage plants; crops such as cereals, vegetables, fruit trees, and fiber plants; trees; turf 'Specific examples include the following.

Flower buds: 卜 Eustoma russel I ianum, stock (Mathiola incana) force (D i anthus caryophy 11 us), chrysanthemum (Chrysanthemum mor ifo I i um), etc .; grain: rice (Oryza sativa), Maize (Zea mays) etc .;

Trees: woody species such as Satsuki (Rhododendron indicum), sushi (Rhododendron Kurume), suki (Cryptomer ia japonica);

Turf: Bengross grass (Agrostis stolon if era), Koraishinoku (Zoisia tenuifol ia), etc .;

Village: Ycopersicon esculentum, green pepper (Capsicum annuum), capsicum annuum, Sitru! Lus lanatus, Cucuris sativus, Cucurbita moschata, melon me lo), cabbage (Brass i ca oleracea var. capitata), broccoli (Brass ica oleracea var. italics), Chinese cabbage (Brass ica campestr is), etc.

Raw and spicy vegetables such as celery (Apium graveolens L.), parsley (Petrosel ium or i spurn), lettuce (Lactuca sativa), Leek (A 11 i um fi stu i osum), onion (A 11 i um cepa L.), garlic (A 11 ium sativum),

Legumes such as soybean (Glycine max), green beans (Phased us vulgaris), endou (Pi sum sativum L.), azuki (Vigna angular is),

Root vegetables such as radish (Raphanus sativus), turnip (Brass ica rapa), carrot (Daucus carota L), burdock (Arctium lappa L.),

Potatoes (Co I ocas ia esculenta), potatoes (So I anum tuberosum), sweet potatoes (I pomoea batatas), potatoes (Dioscorea batatas) and other potatoes, asparagus (Asparagus off icinal is), spinach Spinacia oleracea)> soft vegetables such as honey bees (Gryptotaenia japonica)

Oil crops such as rapeseed (Brassica rapa var. Nippo-oleifera) and arachas hypogaea,

Sugar crops such as sugar cane (Saccharum officinamm) and sugar beet (Beta vulgaris),

Textile products such as ivy (Gossypium spp.) And igusa (Juncus effusus var. Decipiens),

Forage crops such as clover (Trifolium repens) and sorghum (Sorghum vul are); fruit crops such as ichiko (Fragar ia x ananassa);

Fruit trees: Deciduous fruit trees such as apple (Mai us pumi la var. Domestica), pear (Pyrus pyr ifol ia), bud (Vitis spp.), Peach (Prunus persica), chestnut (Castanea crenata),

Citrus such as citrus (Citrus unshiu), lemon (Citrus I imon), grapefruit (G is rus paradisi);

Smoke-reactive plants: Gonostyl is candicans, Styl idium aff ine, Brunonia austraris, etc .;

One thousand (Avena sativa) and turnip (Brassica rapa).

The butenolide compound represented by the formula (I) can also be used for promoting the germination and growth of weeds. For example, it can be used for controlling the germinated weeds with a herbicide or mechanically. is there. The plant growth promoter of the present invention is a mixture of a bunolide compound represented by the formula (I) with a solid carrier, a liquid carrier, and the like, and if necessary, a surfactant and other adjuvants for preparations are added. The butenolide compound represented by the formula (I) is usually prepared in the formulation in an emulsion, a wettable powder, a suspension, a water solvent, etc. 0 1-9 8 weight ^_0/0, preferably rather is contained 0.0 0 0 0 0 0 0 0 0 5-5 0 weight ⁰ / o.

Examples of solid carriers used in the formulation include clays (such as force orinite, diatomaceous earth, synthetic hydrous silicon oxide, fubasami clay, ben lantern clay, acidic clay), talc, and other inorganic minerals (sericite, quartz) Powder, sulfur powder, activated carbon, calcium carbonate, etc.) and fine powders and granules of chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, ammonium sulfate, urea, etc.). Examples of liquid carriers include water, alcohol (Methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (toluene, xylene, ethylbenzene, methyl naphthalene, etc.), non-aromatic hydrocarbons (he) Hexane, cyclohexane, kerosene, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonite) ), Ethers (dioxane, diisopropyl ether, etc.), acid amides (dimethylformamide, dimethylacetamide, etc.), halogenated hydrocarbons (dichloroethane, trichloroethylene, etc.), and organic Sulfur (dimethyl sulfoxide etc.) is mentioned. Surfactants include, for example, alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylenates, polyethylene glycol ethers, many And monohydric alcohol esters, and sugar alcohol derivatives. Other formulation adjuvants include, for example, casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, and synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone). , Polyacrylic acid, etc.), PAP (acidic isopropyl phosphate), BHT (2,6-tert-butyl_4_methylphenol), BHA (2- / 3-tert) ₄ -methoxyphenol), vegetable oils, mineral oils, fatty acids, and stabilizers such as fatty acid esters. The plant growth promoter of the present invention can promote the growth of the plant by, for example, treating the soil as it is or after diluting with water or the like. The plant growth promoter of the present invention can also be used after being applied to the foliage and / or branches of the plant. In such a case, the plant growth promoter of the present invention is treated once or more than once for the plant.

When the plant growth promoter of the present invention is used by foliar treatment on the plant body or when it is used by soil treatment, the treatment amount depends on the preparation form, application time, application method, application location, target plant, etc. Although appropriately selected, the amount of the butenolide compound represented by the formula (I) is usually 1 000 g per hectare. In addition, the concentration used when the plant growth promoter of the present invention is diluted in water is appropriately selected according to the formulation form, application time, application method, application location, target plant, etc.

The concentration of the butenolide compound represented by (I) is usually 1 p pi: ˜100 p pm, preferably 10 p pt—20 p pm.

When the plant growth promoter of the present invention is an emulsion, a wettable powder, a flowable agent or the like, the plant growth promoter of the present invention is usually applied after diluted in water. Dilution of such a case is usually 0.1 as the concentration of Butenori de the compounds of formula (I) (p000000001~ 98 wt%, preferably from 0.0000000005 to 50 weight ⁰ / o. Facilitate plant growth of the present invention When the agent is a powder, granule or the like, the plant growth promoter of the present invention is usually applied as it is.

The plant growth promoter of the present invention can be used for direct treatment on the seed of the target plant. As such a treatment method, for example, the plant growth promoting agent of the present invention or a diluted solution thereof prepared so that the concentration of the butenolide compound represented by the formula (I) is 1 ppt to 10 000 p pm may be used. And a method of spraying or smearing seeds, and a method of dressing the plant growth promoter of the present invention. Further, the plant growth promoter of the present invention can be used for treating a plant before transplantation. Such treatment methods include, for example, the plant growth promoter of the present invention prepared such that the concentration of the butenolide compound represented by the formula (I) is 1 ppt to 10,000 ppm, or a diluted solution or suspension thereof. A method of immersing the root of the plant or the whole plant in the liquid is mentioned. The plant growth promoter of the present invention can be further mixed with a hydroponic solution in hydroponic cultivation of plants, or can be used as a medium component in tissue culture of plants. Such a treatment method is, for example, diluted in a hydroponic solution used for hydroponics of plants so that the concentration of the butenolide compound represented by the formula (I) is 1 ppl: ~ lOOOOOOpm. Or a method of suspending, and a method in which the concentration of the butenolide compound represented by the formula (I) is 1 ppt to 10000 p pm in a plant tissue cell or a medium usually used for cell culture. Can be mentioned. In such a case, a saccharide as a carbon source and various plant hormones can be appropriately contained in the same manner as a commonly used method. The plant growth promoter of the present invention can also be used with fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators and / or fertilizers.

When the plant whose growth is promoted by the plant growth promoter of the present invention is weed, it is effective to control the weed by controlling it with a herbicide after forcibly germinating by the application method described above. The ability to control naturally Before the striker, a root parasitic plant, infests the host plant, the plant growth promoter of the present invention is used to promote the germination of rice moth. Then, the host plant can be protected from infestation by striga by controlling with a herbicide.

The compound represented by the formula (II) and the compound represented by the formula (III) are useful as intermediates for producing the butenolide compound represented by the formula (I). However, these compounds themselves also contribute to plant growth. Since it is effective to promote, it is useful as an active ingredient of a plant growth promoter in the same manner as the butenolide compound represented by the formula (I). The compound represented by the formula (II) or the formula (III) It is also possible to promote plant growth by applying an effective amount of the compound represented by the above to a plant or a plant growth site. Example

Hereinafter, the present invention will be described with reference to production examples, formulation examples, test examples, and the like.

Unless otherwise stated, ¹ H-NMR indicates the chemical shift (<5) value measured at room temperature (about 25 ° C) using 亍 -methylsilane as an internal standard.

First, production examples of the butenolide compound represented by the formula (I) are shown.

Production example 1 After mixing 55 mg of the compound represented by the formula (II) and 2 mI of tetrahydrofuran, and adding 72 mg of 1,8-diazabicyclo [5.4.0] unde force 7-en under ice-cooling, Stir at room temperature for 24 hours. To the reaction mixture were added ice-cooled 5% hydrochloric acid (1 ml), water (10 ml) and ethyl acetate (2OmI) for liquid separation. The aqueous layer was extracted twice with 2 Om I ethyl acetate, and the organic layers were combined, washed with saturated brine 2 Om I, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 3. mg of butenolide compound represented by the formula (I).

White crystals, melting point: 1 1 1. 0 to 1 1 3. 0 ° C

¹ H-NMR (CDC I ₃ ) δ (p pm): 1, 86 (3 Η, d, J = 2. OH z), 3.81 (1 H, dd, J = 1 0. 4, 1 2 8 H z), 4. 63 (1 H, dd, J = 6.4, 1 0. 4 H z), 4. 95 (1 H, ddd, J = 2. 0, 6. 4, 1

2. 8 H z), 5. 73 (1 H, d, J = 6. OH z), 6. 75 (1 H, d, J = 6.0 H z)

Next, production examples of the compound represented by the formula (II) and the compound represented by the formula (III), which are intermediates for producing the butenolide compound represented by the formula (I), are shown.

Production example 2

67 mg of the compound represented by the formula (III) and 1 mg of acetonitrile 1 Om I are mixed, and 465 mg of 1,3-dibromo-5,5-dimethylhydantoin and 6 mg of benzoylbaxoxide are added thereto. Reflux for hours. The reaction mixture cooled to near room temperature was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to obtain Compound 3 Omg represented by the formula (II).

¹ H-NMR (CDC I ₃ ) δ (ppm): 1.92 (3 H, d, J = 1.6 H z),

3.08 (1 H, t, J = 1 0. 6 Hz), 3.65 (1 H, dd, J = 2.4, 1 2. 8 Hz), 4.29 (1 H, d, J = 1 2. 8 H z), 4. 59 (1 H, dd, J = 6. 4, 1 0. 6H z), 5. 01 (1 H, d, J = 2.4 H z), 5. 1 9 ~ 5.24 (1 H, m)

Melting point: 7 1.5-73.5 ° C

Production Example 3

Formula (IV—a)

3 a- iodide 1 3 -methyl 1 2, 3, 4, 5, 7, 7 a-hexahydrofuro [2,3-c] pyran-2-one 32 Omg and tetrahydrofuran 6m I The mixture was mixed, and 358 mg of 1,8-diazabicyclo [5.4.0] undecaker 7-en was added thereto under ice-cooling, followed by stirring at room temperature for 1 hour. To the reaction mixture, ice-cooled 5% hydrochloric acid 1 Om I and ethyl acetate 20m I were added for liquid separation, and the aqueous layer was extracted twice with 20m I of ethyl acetate. The organic layers were combined, washed with saturated brine 3 Om I, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 61 mg of the compound represented by the formula (III).

White crystals, melting point: 74.5 ~ 75.0 ° C

¹ H-NMR (CDC I ₃ ) ^ (p pm): 1.87 (3 H, t, J = 1. 7 Hz), 2.55 to 2.65 (1 H, m), 2.78 (1 H, dd, J = 2. 0, 1 2.0 H z), 2.98 (1 H, t, J = 1 0. 4 H z), 3. 21 (1 H, dt, J = 2 0, 1 2. 0H z), 4.21 (1 H, dd, J = 6. 8, 1 2. OH z), 4.52 (1 H, dd, J = 6. 8, 1 0. 4H z), 4.66 to 4.72 (1 H, m)

Furthermore, production examples of production intermediates are shown as reference production examples.

Reference production example 1

Sodium hydride (55 wt%) 1. 20 g and anhydrous dimethylformamide 3 Om I were mixed, and this was mixed with triethyl 2-phosphonopropionate 6.6 0 g and anhydrous dimethylformamide 1 Mixture with Om I, then formula (VII)

After adding a mixed solution of 2.50 g of 4trahydro-4H-pyran-4-one and anhydrous dimethylformamide 1 OmI represented by the formula, the mixture was stirred at room temperature for a while. The reaction mixture was poured into 100 ml of ice-cooled 5% hydrochloric acid, and the aqueous layer was extracted three times with 150 ml of ethyl acetate. The organic layers were combined, washed with 150 ml of saturated brine, and dried over anhydrous magnesium sulfate. And concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain the formula (VI-1a)

Ethyl 2- (tetrahydro-1 4 H_bilanilidene) propionate and the formula (V I— 2 a)

Ethyl 2- (2,3-dihydro-6 Η-pyran-1-4-> プロ) represented by the following formula: 1.96 g of an about 1: 1 mixture of probione ginseng was obtained.

¹ H-NMR (CDC I ₃ ) δ (p pm): 1. 2 1. 3 (m), 1. 88 (s), 2. 05 2. 20 (bq), 2. 38 (bt), 2 67 (bt), 3.1 (bq) 3.65 3. 80 (m) 4.1 4.2 (m) 5. 59 (s) Reference production example 2

About 1: 1 of ethyl 2- (tetrahydro-4H-biranylidene) propionate and ethyl 2_ (2,3-dihydro-6H-pyran-4-yl) obtained in Reference Production Example 1 3.96 g of the mixture, ethylene glycol 3 Om I, and 1.80 g of hydroxide power were mixed and stirred at 200 ° C. for 6 hours. To the reaction mixture cooled to near room temperature, 60 ml of ice water was added, adjusted to pH 3 with 5% hydrochloric acid, and then ethyl acetate.

Extracted 3 times at 50 ml. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the formula (V— 1)

2— (2,3-Dihydro-6 Η-pyran-4-yl) Propionic acid and formula (V—2)

3.09 g of a mixture of about 9 1 of 2- (tetrahydro-l 4 H-bilanilidene) propionic acid represented by

¹ H-NMR (CDC I ₃ ) <5 (p pm) 1. 30 (3 H, d) 2. 06 2. 30 (2 H, bd) 3. 1 4 (2 H, dq) 3. 7 3 85 (2 H, m) 4. 1 7 (2H d), 5. 65 (1 H t)

Reference production example 3

Formula obtained in Reference Production Example 2 (V-1)

2- (2,3-dihydro-6-pyran-1-yl) propionic acid and the formula (V-2)

2— (Tetrahydro-4H-vinylylidene) represented by the following: A mixture of about 9: 1 of propionic acid 1.0 g, sodium hydrogen carbonate 1 · 1 g, water 1 Om I and black mouth form 25 m I To this was added 1.95 g of iodine, and the mixture was stirred at room temperature for 2 hours. About 0.5 _g of sodium metabisulfite powder was added to the reaction mixture, liquid separation was performed, and the aqueous layer was extracted twice with 2 Om I black mouth form. The organic layers were combined, washed with saturated brine 3 Om I, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain the formula (IV—a)

As a result, 406 mg of xahydro-furo [2,3-c] pyran-2-one was obtained. ¹ H-NMR (CDC I ₃ ) ά (p pm): 1. 32 (3 H, d), 1. 74 (1 H, m), 1. 89 (1 H, m), 3.1 2 ( 1 H, q), 3.56 (1 H, dt), 3.90 (1 H, m), 4.07 (1 H, dd), 4.21 (1 H, d), 4.5 1 (1 H, s)

Next, formulation examples are shown. Parts indicate parts by weight.

Formulation example

By fully stirring and mixing 1 part of a butenolide compound represented by the formula (I) and 99 parts of dimethyl sulfoxide, a preparation which is a plant growth promoter of the present invention was obtained.

Test examples show that the present invention is effective.

Test example

The formulation obtained in the formulation example was further diluted with dimethyl sulfoxide (DMSO) to prepare a DMSO dilution in which the butenolide compound represented by the formula (I) was 1 OO p pm (weight basis), and then the DMSO dilution The liquid and ultrapure water were mixed to obtain an aqueous diluted solution having a concentration of the butenolide compound represented by the formula (I) of 100 ppb (weight basis). Place a filter paper with a diameter of 5 Omm on the bottom surface of a plastic petri dish with a diameter of 6 Omm, drop 1.5 ml of the above aqueous diluent evenly onto the filter paper, and then lettuce (Lactuca sativa L in a dark room under safety light). _cv. Grand Rapids) ό seeds 30 seeds were plated on filter paper and then, after sealing the Plasti Kkushare with parafilm, placed in a dark box, and Bok Incubation in the dark 25 ° C. The number of lettuce seeds germinated 48 hours later was counted to determine the germination rate. The test was repeated three times.

As a control, the following formula (A)

The same test was carried out using a compound represented by the formula (W ○ 2005/061 51 5 Compound described in Formula 1a in 5 pan freets).

As a result, the germination rate in the test using the butenolide compound represented by formula (I) was 59%, whereas the germination rate in the test using the compound represented by formula (A) was 28%. Met. Industrial applicability

Since the butenolide compound represented by the formula (I) has a plant growth promoting effect, it can be used in various applications.

Claims

Formula (I)

Butenolide compound represented by

2. A plant growth promoter comprising the butenolide unification α − = blue compound according to claim 1 as an active ingredient.

3. A method for promoting plant growth, which comprises applying an effective amount of the butenolide compound according to claim 1 to a plant or a plant growth site.

4. A method for promoting germination of a plant, which comprises applying an effective amount of the butenolide compound according to claim 1 to a plant or a place where the plant grows.

5. Formula (II)

A compound represented by

6. Formula (III)

A compound represented by