WO2002007517A1 - Inhibiteurs de la biosynthèse de l'éthylène dans des plantes - Google Patents

Inhibiteurs de la biosynthèse de l'éthylène dans des plantes Download PDF

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Publication number
WO2002007517A1
WO2002007517A1 PCT/JP2001/006256 JP0106256W WO0207517A1 WO 2002007517 A1 WO2002007517 A1 WO 2002007517A1 JP 0106256 W JP0106256 W JP 0106256W WO 0207517 A1 WO0207517 A1 WO 0207517A1
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WO
WIPO (PCT)
Prior art keywords
compound
acceptable salt
agriculturally acceptable
plant
active ingredient
Prior art date
Application number
PCT/JP2001/006256
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English (en)
Japanese (ja)
Inventor
Nobuaki Mito
Noritada Matsuo
Michihiko Fujinami
Original Assignee
Sumitomo Chemical Company, Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Publication of WO2002007517A1 publication Critical patent/WO2002007517A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B7/00—Preservation or chemical ripening of fruit or vegetables
    • A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
    • A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
    • A23B7/154—Organic compounds; Microorganisms; Enzymes
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N3/00—Preservation of plants or parts thereof, e.g. inhibiting evaporation, improvement of the appearance of leaves or protection against physical influences such as UV radiation using chemical compositions; Grafting wax
    • A01N3/02—Keeping cut flowers fresh chemically
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom

Definitions

  • the present invention relates to an inhibitor of ethylene biosynthesis in a plant.
  • Ethylene is a plant hormone involved in biomechanism such as promoting plant maturation.
  • 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). ].
  • Plant hormones Yasuyuki Katsumi, 199 1 year
  • Life of Plants and Ethylene Yasuo Ota, 1980, Tokai University Press
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.)
  • 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
  • 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, ⁇ , 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. ]
  • 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.
  • an inert carrier such as a solid carrier or a liquid carrier
  • 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.
  • 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.
  • surfactant examples include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyethylene glycol ethers, polyhydric alcohol esters, And sugar alcohol derivatives.
  • 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.
  • PAP isopropyl oxyphosphate
  • BHT 2,6-tert-butyl-4-methylphenol
  • BHA 2,3- / 3-tert-butyl-4-methoxyphenol
  • 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.
  • the compound of the present invention is treated once or plural times with respect to a target plant.
  • the compound of the present invention 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.
  • the agent of the present invention is usually diluted in water and sprayed on cotton poles and foliage before harvesting.
  • 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.
  • 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.
  • 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.
  • 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 to C10 alkyl group specifically, a butyl group, a 1-methylpropyl group (s_butyl group)
  • Pentyl group 1-methylbutyl group, 2-methylbuty
  • 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.
  • R represents the same meaning as above, X represents a group represented by a chlorine atom, a hydroxyl group or the formula RC0 2. ]
  • 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.
  • the acid include an organic acid such as trifluoroacetic acid.
  • 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.
  • the condensing agent include dialkyl carbodiimides such as dicyclohexyl carbodiimide.
  • 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.
  • a base eg, sodium hydroxide, sodium ethoxide, isopropylamine, etc.
  • a solvent eg, water, methanol, ethanol, acetone, ethyl acetate, etc.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Test compound Test compound concentration ACC concentration Ethylene generation
  • 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.
  • 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.
  • Tomatoes were cultivated in a greenhouse, and unripe tomato fruits with a diameter of about 2 cm were harvested.
  • 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.

Abstract

Il est apparu que les composés (I) correspondant à la formule générale suivante (I), formule dans laquelle R représente un hydrocarbyle porteur de 4 à 10 atomes de carbone, ou leurs sels acceptables du point de vue agricole, pouvaient être utilisés comme ingrédients actifs de régulateurs de la croissance de plantes et ce, dans la mesure où ils ont une action inhibitrice de la biosynthèse de l'éthylène dans des plantes. On peut utiliser ces composés ou leurs sels acceptables du point de vue agricole, notamment pour prévenir la chute de fruits, de graines de coton, de fleurs, de jeunes bourgeons ainsi que pour conserver leur fraîcheur à des fruits, à des fleurs coupées ainsi qu'à des légumes, etc.
PCT/JP2001/006256 2000-07-21 2001-07-18 Inhibiteurs de la biosynthèse de l'éthylène dans des plantes WO2002007517A1 (fr)

Applications Claiming Priority (2)

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JP2000220511 2000-07-21
JP2000-220511 2000-07-21

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WO2002007517A1 true WO2002007517A1 (fr) 2002-01-31

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3927034A (en) * 1972-10-20 1975-12-16 Nippon Soda Co 3,4-Dihydro-2H-pyrane-2,4-diones
WO1988004652A1 (fr) * 1986-12-17 1988-06-30 Nippon Soda Co., Ltd. Composes heterocycliques possedant un squelette triketo
JPH05117113A (ja) * 1991-05-08 1993-05-14 Mitsubishi Gas Chem Co Inc 植物のエチレン生成阻害剤
JPH07233010A (ja) * 1994-02-21 1995-09-05 Mitsubishi Gas Chem Co Inc 抽台抑制剤
EP0841063A1 (fr) * 1996-03-27 1998-05-13 Toray Industries, Inc. Derives de cetone et usage medicinal

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3927034A (en) * 1972-10-20 1975-12-16 Nippon Soda Co 3,4-Dihydro-2H-pyrane-2,4-diones
WO1988004652A1 (fr) * 1986-12-17 1988-06-30 Nippon Soda Co., Ltd. Composes heterocycliques possedant un squelette triketo
JPH05117113A (ja) * 1991-05-08 1993-05-14 Mitsubishi Gas Chem Co Inc 植物のエチレン生成阻害剤
JPH07233010A (ja) * 1994-02-21 1995-09-05 Mitsubishi Gas Chem Co Inc 抽台抑制剤
EP0841063A1 (fr) * 1996-03-27 1998-05-13 Toray Industries, Inc. Derives de cetone et usage medicinal

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LOKOT I.P. ET AL.: "A new approach to the synthesis of 3,6-and 5,6-dialkyl derivatives of 4-hydroxy-2-pyrone. Synthesis of rac-germicidin", TETRAHEDRON, vol. 55, no. 15, 1999, pages 4783 - 4792, XP002948549 *

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