WO2005041671A1 - 植物に対する病害抵抗性誘導活性を有する組成物およびその製造方法 - Google Patents

植物に対する病害抵抗性誘導活性を有する組成物およびその製造方法 Download PDF

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WO2005041671A1
WO2005041671A1 PCT/JP2004/016237 JP2004016237W WO2005041671A1 WO 2005041671 A1 WO2005041671 A1 WO 2005041671A1 JP 2004016237 W JP2004016237 W JP 2004016237W WO 2005041671 A1 WO2005041671 A1 WO 2005041671A1
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Prior art keywords
hydroxy
sinole
dihydroxy
sphingenin
gnorecocinole
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PCT/JP2004/016237
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English (en)
French (fr)
Japanese (ja)
Inventor
Kenji Umemura
Jinichiro Koga
Toshiaki Kono
Hideki Usami
Yuichi Sato
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Meiji Seika Kaisha, Ltd.
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Priority to JP2005515197A priority Critical patent/JPWO2005041671A1/ja
Publication of WO2005041671A1 publication Critical patent/WO2005041671A1/ja

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/40Liliopsida [monocotyledons]
    • A01N65/44Poaceae or Gramineae [Grass family], e.g. bamboo, lemon grass or citronella grass
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08Magnoliopsida [dicotyledons]
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08Magnoliopsida [dicotyledons]
    • A01N65/20Fabaceae or Leguminosae [Pea or Legume family], e.g. pea, lentil, soybean, clover, acacia, honey locust, derris or millettia
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/40Liliopsida [monocotyledons]

Definitions

  • the present invention relates to a plant disease resistance-inducing composition having a low environmental load and having an excellent controlling effect, and a method for producing the same.
  • Chemical pesticides such as fungicides and invasion inhibitors are mainly used in the method of controlling disease on agricultural crops, and these chemical pesticides inhibit the infectious function of chemical substances having fungicidal action against plant pathogens and pathogens.
  • the active ingredient is an active ingredient.
  • these types of pesticides are expected to have little or no effect beyond the target organisms, including safety to the user, impact on crop safety due to residue on the crop, and environmental impact. There are concerns about the load on the system. Furthermore, it has been clarified that continuous use of such chemical pesticides promotes the development of resistant bacteria to the chemicals.
  • the disease control effect of cerebrosides includes the rice disease control effect of cereb mouth side derived from plant pathogenic fungi (Japanese Patent No. 2846610, W098Z47364) and the use of cerebside side plant derived fungi against various crops. Disease control (WO 03Z020032) is known. All of these are unique to filamentous fungi, including phytopathogenic bacteria.
  • the active ingredient is celeb mouth side having methyl branch.
  • a plant-derived celebrity mouth side includes a celebrity mouth side portion in which a sphingosine base portion is composed of various molecular species (Kaul, K. et al., Plant Physiol, 1975, 55, 120-129, Ohnishi M. et al, Biochim. Biophys. Acta, 1983, 752, 416-422, Imai H. et al "Biosci. Biotechnol. Biochem., 1997, 61, 35 353, Imai H. et al., Plant Physiol., 2000, 157, 453-456).
  • an object of the present invention is to provide a composition for inducing plant disease resistance and a method for producing the same.
  • the plant disease resistance-inducing composition according to the present invention comprises a plant-derived amphipathic substance as an active ingredient.
  • the method for producing a plant disease resistance-inducing composition according to the present invention is characterized in that an amphipathic substance is selected from a plant material by converting two or more substances selected from the group consisting of water, a surfactant and an organic solvent. Extracting with a mixed solvent or organic solvent of the substances, concentrating the extract obtained by the extraction, and precipitating and removing plant physiologically inhibitory substances contained in the extract.
  • the composition for inducing plant disease resistance according to the present invention uses a plant or a plant processed product as a raw material, and thus has a pesticide that is safe for producers and consumers of agricultural products. Can be used. Furthermore, the composition for inducing plant disease resistance according to the present invention is an environmentally conscious agricultural material that can be used for sustainable agricultural production techniques and organic cultivation. Can be reduced.
  • the term "amphiphilic substance” refers to a molecule having both a polar group and a hydrophobic group! At a critical micelle concentration, the hydrophobic groups are aggregated by hydrophobic bonds, and the polar group is present on the surface. By forming such micelles, solubility in water is improved.
  • “simple lipid” refers to an ester of a fatty acid and various alcohols.
  • the “complex lipid” refers to a lipid containing P (phosphorus), S (sulfur), a nitrogen-containing base or a saccharide in a molecule.
  • the “phospholipid” refers to a lipid having a phosphate ester or a phosphonate ester in a molecule.
  • “glycolipid” refers to a lipid having a sugar in a molecule.
  • ⁇ sphingolipids '' refers to lipids containing long-chain bases such as sphingosine, wherein the chain length is preferably 14 to 24 carbon atoms, more preferably 18.
  • the term “glycemic lipid” refers to a lipid containing glycerol.
  • the disease resistance-inducing composition according to the present invention is characterized by comprising a plant-derived amphipathic substance as an active ingredient.
  • the amphiphilic substance in the present invention can contain simple lipids or complex lipids alone or in combination. Therefore, the present invention According to a preferred embodiment, the amphiphile is a simple lipid, a complex lipid, or a mixture thereof.
  • the simple lipid in the present invention is preferably triglyceride, diglyceride, monoglyceride or the like, and more preferably diacylglycerol.
  • the complex lipid in the present invention is preferably a phospholipid and Z or glycolipid.
  • the phospholipid is preferably a glycemic phospholipid or a sphingophospholipid, and more preferably a phosphatidylcholine.
  • the glycolipid is preferably a glycemic glycolipid or a glycosphingolipid, and more preferably cerebroside.
  • the complex lipid is a sphingolipid.
  • Preferred such sphingolipids include the following compounds:
  • l-Q- ⁇ - -Knole ⁇ -Sinore- - ⁇ -2, -Hydroxylignocelluloyl 3, 4-dihydroxysphinganine,
  • ⁇ - ⁇ - ⁇ - -Knole 1 shinore- - ⁇ -2, -Hydroxypalmitoyl-3-Hydroxy-4 sphingen
  • ⁇ - ⁇ - ⁇ - -Knore ⁇ -Sinore- - ⁇ -2, -Hydroxypalmitrail 3-Hydroxy-4 sphingenin,
  • ⁇ - ⁇ - ⁇ - -Knole ⁇ -Sinole- - ⁇ -2, -Hydroxystearoyl-3-hydroxy-4 sphingen
  • ⁇ - ⁇ - ⁇ - -Kunore 1 shinore- - ⁇ -2, Hydroxyoleoyl 3-Hydroxy-4 sphingen,
  • ⁇ - ⁇ - ⁇ - -Knore ⁇ -Sinore- - ⁇ -2, -Hydroxybase oil 3-Hydroxy-4 sphingen
  • ⁇ - ⁇ - ⁇ - -Kunore 1 shinore- - ⁇ -2, -Hydroxylignocelluloyl 3-Hydroxy-8 sphingenin,
  • ⁇ - ⁇ - ⁇ - -Knore ⁇ -Sinore- - ⁇ -2, Hydroxymyristoyl 4-Hydroxy-8 sphingen,
  • ⁇ - ⁇ - ⁇ - -Knole ⁇ -Sinole- - ⁇ -2, -Hydroxypalmitoyl 4-Hydroxy-8 sphingen
  • ⁇ - ⁇ - ⁇ - -Kunore 1 Chinore- - ⁇ -2, -Hydroxypalmitrail 4-Hydroxy-8 sphingenin,
  • ⁇ - ⁇ - ⁇ - -Knore ⁇ -Sinore- - ⁇ -2, -Hydroxystearoyl-4-Hydroxy-8 sphingen
  • lO- ⁇ -Gnorecocinole 2-hydroxylignocelluloyl 3, 4-dihydroxy-8-sphingenin, lO- ⁇ -Gnorecocinole — 2-hydroxymyristoyl 3-hydroxy-4,8-sphinga jenin,
  • the above compounds can be used alone or as a combination of two or more compounds in the composition for inducing plant disease resistance according to the present invention.
  • the sphingolipid is a 4,8-sphingadienin
  • preferable examples of such a 4,8-sphingadienin include the following compounds. :
  • the above compounds can be used alone or as a combination of two or more compounds in the composition for inducing plant disease resistance according to the present invention.
  • the amphiphile is celeb mouth side, phosphatidyl. Choline, sulfatide, sphingomyelin, phosphatidylserine, and diacylglycerol powers are at least one selected.
  • the amphiphile is a mixture containing at least sphingolipid, glycerol lipid, and diacylglycerol.
  • the amphiphilic substance is a mixture comprising at least celeb mouth side, phosphatidylcholine, and diacylglycerol.
  • the amphiphilic substance in the present invention is preferably obtained from at least one plant selected from oil crops, cereals, and legumes. And as a plant raw material of the amphiphilic substance in the present invention, a processed plant product such as a by-product in a process of manufacturing a food, which can use a plant as it is, may be used.
  • the plant material of the amphipathic substance is at least one which is also selected from corn, rapeseed, sesame, soybean, rice, wheat and oemica.
  • the plant material of the amphipathic substance is at least one selected from the group consisting of corn bran, dalten meal, rapeseed meal, sesame seeds, soybean meal, rice bran, and wheat bran.
  • the amphiphilic substance is extracted from a plant raw material with a mixed solvent or an organic solvent of two or more substances selected from the group consisting of water, a surfactant, and an organic solvent. Things. In this extraction, it is preferable that the plant material is immersed in the mixed solvent or the organic solvent and stirred.
  • Examples of the mixed solvent used for the extraction include a solvent obtained by adding an appropriate amount of water to an organic solvent, a solvent containing an organic solvent and a surfactant in an appropriate ratio, or water and a surfactant. Solvents and the like. If a surfactant is used in the extraction, a mixed solvent containing the surfactant is first prepared, and the plant material may be immersed in this mixed solvent and stirred, and the surfactant is not included! ⁇ ⁇ Soak the plant material in the solvent After stirring, a surfactant may be added to the solvent. And according to a preferred embodiment of the present invention, the mixed solvent also has water and surfactant power.
  • the surfactant is added so as to be preferably less than 1% (WZW), more preferably 0.1-0.5% (w Zw), based on water.
  • Examples of the surfactant in the mixed solvent include nonionic (also referred to as "nonione”) surfactants, a-one surfactants, and cationic surfactants. These can be used alone or in combination of two or more.
  • nonionic surfactant polyoxyethylene nonylphenyl ether, polyoxyethylene alkynyl ether, polyoxyethylene sorbitan ester, polyoxyethylene phenyl ether, sorbitan fatty acid ester, or polyoxyethylene fatty acid ester Esters, and the like.
  • aeon-based surfactant examples include an alkylbenzene sulfonate, an alkyl ether sulfate, a sulfonate, and an alkylnaphthalene sulfonate. Examples thereof include alkylamine salts and quaternary ammonium salts. Further, in the present invention, it is preferable to use a surfactant used as a food additive in terms of safety aspects.
  • propylene glycol fatty acid ester chondroitin sulfate, sucrose fatty acid ester, sorbitan fatty acid Esters, glycerin fatty acid esters, medium-chain fatty acid tridalicelide, sorbitol, mannitol, and organic acid monodalicelide (for example, succinic acid monodalicelide, citrate monoglyceride and the like).
  • the organic solvent used for the extraction examples include ethanol, methanol, hexane, petroleum ether, ethyl ether, ethyl acetate, chloroform, and acetone.
  • the organic solvent in the present invention is preferably ethanol or methanol when it is used as an agricultural material that can be used for cultivation of organic agricultural products, which is preferably a solvent having high extraction efficiency, which is preferably ethyl acetate or black-mouthed form.
  • the extraction is preferably performed under appropriate conditions according to the properties of the plant material, the type of organic solvent and surfactant used, and the like.
  • the liquid temperature during the extraction is preferably 15-80. . C, more preferably 25-60. C.
  • the composition for inducing plant disease resistance is preferably obtained by concentrating the extract obtained by the above-mentioned extraction and removing the physiologically inhibitory substances of the plant by precipitation. .
  • This concentration makes it possible to increase the content of the active ingredient in the composition and to precipitate and remove the plant physiologically inhibitory substances.
  • the physiologically inhibitory substances of plants refer to substances that, when processed into crops, cause black-mouth bleeding (yellowing) to the foliage tissues and suppress the growth of the crops.
  • the composition for inducing plant disease resistance according to the present invention can exhibit an affinity action more strongly. Strong spreading action can be exhibited.
  • the concentration of the active ingredient at which the spreading action is sufficiently exerted is preferably 0.001 to 0.4% (wZw), more preferably 0.01 to 0.1% (WZW). At such a concentration of the active ingredient, the spreadability to the leaves during spraying and the absorption during rooting treatment are improved, so that the spreadability of the amphiphilic substance as the active ingredient to the plant is improved. It is possible to enhance permeation transferability.
  • the plant disease resistance-inducing composition according to the present invention exhibits a spreading effect, it is not necessary to add a spreading agent at the time of application or only a small amount of the spreading agent is added. Can be reduced. Therefore, according to a preferred embodiment of the present invention, the composition for inducing plant disease resistance has an amphipathic substance content of 0.001 to 0.4% (wZw).
  • Concentration can be performed by a commonly used concentration method such as freeze-drying, vacuum concentration, and heat distillation. However, since concentration at a high temperature is not preferable, it is preferable to carry out thermal distillation by vacuum concentration. In this case, concentrate at a maximum temperature of 80 ° C or less. In addition, the concentration is preferably reduced to a volume ratio of preferably 1Z2-1Z40, more preferably 1Z4-1Z12 as a guide, and the content of amphipathic substance is 0.001% relative to the plant disease resistance-inducing composition. It is preferred to concentrate to 0.4% (w / w).
  • the production method according to the present invention preferably comprises a concentrated liquid plant disease obtained by concentration. Further comprising isolating the harm resistance inducing composition.
  • the isolation method is not particularly limited, and a known method can be appropriately used, and examples thereof include a method of filtering a concentrated solution.
  • the dosage form of the composition for inducing plant disease resistance according to the present invention can be used in any form of agricultural chemicals such as liquids, powders, granules, emulsions, wettable powders, oils, aerosols and flowables.
  • agricultural chemicals such as liquids, powders, granules, emulsions, wettable powders, oils, aerosols and flowables.
  • the composition for inducing plant disease resistance is used as a plant control agent.
  • a method for controlling a plant disease comprising a step of treating a target plant with the composition for inducing plant disease resistance according to the present invention.
  • means for treating the target plant include, but are not limited to, spraying treatment, rooting treatment, irrigation treatment, watering treatment and the like. Further, by combining the above-mentioned treatment means in accordance with the stage of the crop or the cultivation method of the crop, the efficacy and duration of the medicinal effect can be made more effective.
  • the treatment concentration and the number of treatments of the disease resistance-inducing composition according to the present invention may vary depending on the type of crop, the degree of growth of the crop, the mode of development of plant diseases such as above-ground diseases and soil diseases, and the development pressure such as the density of pathogenic bacteria. It can be appropriately selected according to the conditions.
  • the target crops that can be treated with the plant disease resistance-inducing composition of the present invention include all cultivated plants, for example, cereals (rice, barley, wheat, corn, etc.), solanaceous plants (tomato, eggplant). ), Legumes (e.g., cucumber, melon, pumpkin), legumes (e.g., Japanese radish, soybean), cruciferous plants (e.g., radish, Chinese cabbage, cabbage), roses (e.g., strawberry, apple, pear) And the like. Further, it is preferable that the target crop is a plant different from the plant material of the plant disease resistance-inducing composition according to the present invention. For example, when the target crop to be treated is rice, the raw material of the plant resistance inducing composition according to the present invention is a plant raw material other than rice.
  • the target diseases of the above crops are all plant diseases caused by filamentous fungi.
  • filamentous fungi For example, lettuce root rot, tomato wilt, wheat rust, melon vine Disease, strawberry powdery mildew, cucumber anthracnose, cabbage wilt, spinach brown spot, soybean purpura, eggplant powdery mildew, green onion rust, and rice blast.
  • the composition for inducing plant resistance according to the present invention is also effective against any of airborne surface diseases and soil-borne soil diseases.
  • the powder frame was prepared according to ⁇ -02), and the screen opening 1. After making a powder frame product using Omm, it was subjected to the following process.
  • the ethanol extract obtained in the above extraction step was concentrated to an original volume of about 1Z12 under reduced pressure using a rotary evaporator I (Asahi Seisakusho, ARE-20V). After concentration, the obtained ethanol extract was cooled to room temperature, and the precipitate formed in the solution was removed using No. 2 filter paper (trademark: ADVANTEC, manufactured by Toyo Roshi Kaisha, Ltd.), and concentrated to about 400 mL. A liquid was obtained.
  • the surfactant extract obtained in the above extraction step was concentrated and dried under reduced pressure using a monotary evaporator in the same manner as described above. 4 in the obtained dried fraction OOmL of ethanol was dissolved in ethanol and insoluble substances were removed using No. 2 filter paper to obtain a surfactant extract concentrated solution.
  • a control test on rice and rice blast was carried out.
  • eight seedlings of rice (cultivar: Akitakomachi) are sowed per pot and cultivated in an artificial climate chamber.
  • various sample samples (2 mL per pot) are obtained.
  • Foliage application was performed (here, 4 pots per section).
  • a cerebroside B solution (cerebroside B concentration: 10 ppm) was sprayed in the same manner, and for the negative control, water was sprayed. Then, it was left for about 1 hour until the spray liquid was dried on the leaf surface, and then cultivated again in the cultivation room.
  • cerebroside B a sample (sebroside B concentration 2 mg ZmL solution) separated and purified by the method of Umemura et al. (Plant Cell Physiology, 2000, 41, 676-683) was used.
  • Control value (1 average number of lesions per leaf in each section / average number of lesions per leaf in control section) X 100
  • Table 1 shows the control effects of the 100-fold diluted ethanol extract concentrate prepared by the method of Example 1 using various plant materials. Ethanol extract concentrates of plant materials other than rice bran showed a control effect, although there were differences in their control effects.
  • DK Ester SS and S-215 (a non-ionic surfactant for food additives, manufactured by Mitsubishi Chemical Foods Co., Ltd.) were used as surfactants and extracted under various concentration conditions.
  • the phytoalexin-inducing ability was measured for a 50-fold dilution of the surfactant extract concentrate.
  • the results were as shown in Table 3.
  • the results are shown as relative values when the activity when treated with cerebroside B (10 ppm) is defined as 100.
  • the disease resistance inducing activity value in Table 4 is a value indicating the phytoalexin inducing ability of a 50-fold diluted solution of each surfactant extract concentrate, and the activity when cerebroside B was treated with lOppm as 100. It is a relative value.
  • TritonX-100 Nonionic (Mitsubishi Chemical Foods Corporation) 87
  • a seedling of lettuce (variety: Patriot) in which three true leaves were developed was subjected to immersion treatment, irrigation treatment, or foliage treatment using a 100-fold diluted solution of the ethanol extract concentrate prepared in Example 1.
  • contaminated soil diution plate method, lg soil per lettuce root rot fungus ( Inoculation treatment was carried out by transplanting lettuce seedlings into Fusarium oxvsporum f. Sp. Lactucae) race (SB1-1 strain was adjusted to a cell density of 3 ⁇ 10 4 CFU).
  • SB1-1 strain was adjusted to a cell density of 3 ⁇ 10 4 CFU.
  • a cerebroside B solution Cerebroside B concentration: 10 ppm
  • the disease index is 0 when there is no disease, 1 when less than 1Z3 of the vascular bundle changes color, 2 when 1Z3-2Z3 of the vascular bundle changes color, and 2/3 or more of the vascular bundle.
  • the case of discoloration was designated as 3.
  • the control value was calculated according to the formula shown below.
  • control effect was observed even when the concentrated ethanol extract from any plant material was used. Furthermore, the control effect was observed by any of the immersion treatment, irrigation treatment, and spray treatment, and the immersion treatment tended to show the highest control value.
  • the seedlings of tomato developed on a true leaf strength were immersed for 36 hours using a 50-fold or 100-fold dilution of the concentrated ethanol extract.
  • the above-mentioned concentrated ethanol extract was prepared by the method of Example 1.
  • the above-mentioned tomato seedlings were transplanted to contaminated soil (Fusarium oxvsporum f. Sp. Lvcopersici) race J—adjusted to a bacterial density of 3 ⁇ 10 CFU / g of one strain J. Inoculation treatment.
  • Serebroside B solution (cerebroside B concentration: 5 ppm or 10 ppm) was used as a positive control.
  • Example 6 A disease investigation similar to that in Example 3 was conducted 24 days after transplantation, and the control effect of each test solution was examined. The results were as shown in Table 6. The control effect was observed in the concentrated ethanol extracts from all plant materials.
  • a control test was carried out using wheat (cultivar: Norin 61) cultivated at Meiji Seika Co., Ltd. farm (address: 800 Odawara Kapayayama).
  • One test plot was 10 m 2, and the test solution was used at a rate of 150 LZ10a per test plot in the spray treatment.
  • This spraying treatment was carried out three times in each test plot, namely, the heading stage, the heading stage, and the beginning of heading.
  • As infection treatment straw was laid between furrows to promote natural disease, and sprinklers were used to sprinkle water to achieve humid conditions.
  • test solution a 50-fold diluted solution of a concentrated ethanol extract derived from a plant material was used, and as a positive control, a 1000-fold diluted solution of trifmin wettable powder (manufactured by Nippon Soda Co., Ltd.) was used.

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PCT/JP2004/016237 2003-10-30 2004-11-01 植物に対する病害抵抗性誘導活性を有する組成物およびその製造方法 WO2005041671A1 (ja)

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WO2007074788A1 (ja) * 2005-12-27 2007-07-05 University Of The Ryukyus 抗腫瘍剤及び免疫賦活剤
WO2007083030A1 (fr) * 2006-01-20 2007-07-26 Evelyne Monel Composition pour le traitement curatif ou préventif des plantes contre les pathogènes, son procédé de préparation et son utilisation
WO2008032284A3 (en) * 2006-09-13 2008-05-29 Ecolab Inc Conveyor lubricants including emulsion of a lipophilic compound and an emulsifier and/or an anionic surfactant and methods employing them
JP2010120892A (ja) * 2008-11-21 2010-06-03 Fukushima Univ グルコシルセラミド画分およびこれを含む加工品
JP2013067590A (ja) * 2011-09-22 2013-04-18 Maruzen Pharmaceut Co Ltd ヒドロキシ脂肪酸誘導体を含有する抽出物及び乳化物、並びにこれらの製造方法
WO2017125993A1 (ja) * 2016-01-18 2017-07-27 国立大学法人 岡山大学 リグニン抽出物を有効成分とする植物病害防除剤

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