WO2014013743A1 - 植物へのストレスを軽減する薬剤組成物 - Google Patents
植物へのストレスを軽減する薬剤組成物 Download PDFInfo
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- WO2014013743A1 WO2014013743A1 PCT/JP2013/004429 JP2013004429W WO2014013743A1 WO 2014013743 A1 WO2014013743 A1 WO 2014013743A1 JP 2013004429 W JP2013004429 W JP 2013004429W WO 2014013743 A1 WO2014013743 A1 WO 2014013743A1
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- 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
- A01N43/06—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 five-membered rings
- A01N43/08—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 five-membered rings with oxygen as the ring hetero atom
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- the present invention relates to a pharmaceutical composition that reduces stress on plants. More particularly, the present invention relates to pharmaceutical compositions that reduce biological, physical or chemical stress that affect plant growth.
- Plants grown in farmland or ordinary households are always exposed to various biological and abiotic stresses. Cultivated crops generally tend to be less resistant to these stresses. Agricultural chemicals such as bactericides, insecticides and herbicides are used to reduce biological stress such as pests and weeds and maintain yield. However, the effects of pesticides are insufficient, if they are used incorrectly, they cause phytotoxicity, pests and weeds develop resistance to pesticides, and there are concerns about the safety of environmental organisms. In addition, environmental stresses such as temperature, moisture, illuminance, soil pH, and salt concentration are dealt with by appropriate cultivation, breeding improvement, irrigation, greenhouse and soil improvement. Attempts to impart stress resistance with plant growth regulators have been made, but the effect is not sufficient. In addition, plant viral diseases cause serious damage to important crops such as cereals, vegetables and fruit trees. However, until now no drug has been found that sufficiently exerts a practical effect on plant viral diseases.
- Non-Patent Document 1 reports that ascorbic acid is involved in disease resistance, hormonal action, etc.
- Non-Patent Document 2 reports that ascorbic acid affects plant aging.
- ascorbic acid is present in a high concentration in the plant body, even if ascorbic acid is given to the plant from the outside, its physiological influence is slight and there is almost no practical effect.
- Patent Document 1 proposes that certain derivatives of ascorbic acid are applied to plants as having a preventive and therapeutic effect on viral diseases of plants.
- Patent Document 2 discloses a composition containing an antibacterial antibiotic such as neomycin sulfate and ascorbic acid, and states that plant diseases can be suppressed by this composition.
- an antibacterial antibiotic such as neomycin sulfate and ascorbic acid
- Patent Document 3 discloses a composition containing an antibacterial antibiotic such as neomycin sulfate and ascorbic acid, and states that plant diseases can be suppressed by this composition.
- the example which used ascorbic acid together with an agrochemical is proposed for the purpose of stabilization of an agrochemical active ingredient (patent document 3), release control (patent document 4), etc.
- Vitamin 79 (2): 116-117 (2005) Horticultural studies 6 (2): 169-175
- An object of the present invention is to provide a pharmaceutical composition that reduces biological stress, physical stress, or chemical stress that affects plant growth.
- the pharmaceutical composition which reduces the stress to the plant containing the substance (B) which affects the physiological effect of a plant.
- R 1 to R 4 each independently represents a hydrogen atom, —SO 3 H, —PO 3 H 2 , a glycosyl group or —COR 11 .
- R 11 represents an unsubstituted or substituted C1-30 alkyl group or an unsubstituted or substituted C2-30 alkenyl group.
- R 5 and R 6 each independently represents a hydrogen atom, —SO 3 H, —PO 3 H 2 , a glycosyl group or —COR 11 .
- R 11 represents an unsubstituted or substituted C1-30 alkyl group or an unsubstituted or substituted C2-30 alkenyl group.
- composition according to [1], wherein the substance (B) is at least one selected from the group consisting of fungicides, insecticides, plant growth regulators, and herbicides.
- the substance (B) is a respiratory inhibitor.
- the substance (B) is a strobilurin compound.
- the substance (A) is represented by the formula (I) [However, not all R 1 to R 4 are hydrogen atoms at the same time. ]
- substance (A) has the formula (I) [provided that at least one of R 1 ⁇ R 4 represents a -COR 11, R 11 are, C12 ⁇ 30 alkyl group having an unsubstituted or substituted Or an unsubstituted or substituted C12-30 alkenyl group. ]
- the substance (A) is represented by the formula (I) [wherein R 1 to R 4 each independently represents a hydrogen atom or —COR 11 , and at least one of R 1 to R 4 is — COR 11 is shown.
- R 11 represents an unsubstituted or substituted C1-30 alkyl group or an unsubstituted or substituted C2-30 alkenyl group.
- At least one of -COR 11 represents R 11 therein, a C12 ⁇ 30 alkenyl group having C12 ⁇ 30 alkyl group or an unsubstituted or substituted group having an unsubstituted or substituted group.
- the composition as described in [1] which is a compound represented by these, or its salt.
- [8] A method for reducing stress on a plant, comprising applying the composition according to any one of [1] to [7] to the plant.
- the stress is a biological stress caused by plant viruses, phytopathogenic bacteria, phytopathogenic fungi, pests or weeds; or high temperature, low temperature, high illuminance, low illuminance, excessive humidity, drying, salinity, acidity, pesticides, [8]
- the method according to [8] which is at least one of physical or chemical stress caused by a chemical substance or heavy metal.
- the composition of the present invention has an effect of imparting resistance to biological stress, physical stress, or chemical stress to plants, which affects plant growth.
- resistance to plant stress increases, so that, for example, phytotoxicity caused by agricultural chemicals including substances that affect the physiological function of the plant can be reduced, and plant diseases including viral diseases Can reduce the damage.
- plant diseases including viral diseases Can reduce the damage.
- the pharmaceutical composition for reducing stress on plants according to the present invention comprises a substance (A) and a substance (B) that affects the physiological function of the plant.
- the substance (A) is at least one selected from the group consisting of a compound represented by the formula (I), a compound represented by the formula (II), and a salt thereof.
- R 1 to R 4 each independently represents a hydrogen atom, —SO 3 H, —PO 3 H 2 , a glycosyl group or —COR 11 .
- R 5 and R 6 each independently represents a hydrogen atom, —SO 3 H, —PO 3 H 2 , a glycosyl group or —COR 11 .
- the glycosyl group is a sugar residue such as a monosaccharide or a low molecular weight oligosaccharide (specifically, a partial structure of a molecule in which the hemiacetal hydroxy group of the sugar moiety is removed to form a binding position).
- monosaccharides include glucose, galactose, fructose, and rhamnose.
- oligosaccharides include rutinose, vicyanose, lactose, maltose, and sucrose.
- the glycosyl group includes, for example, a glucosyl group, a galactosyl group, a fructosyl group, a rhamnosyl group, and the like.
- the glycosyl group also includes a group in which any combination of these groups is bonded by a 1 ⁇ 2 bond, a 1 ⁇ 3 bond, a 1 ⁇ 4 bond, or a 1 ⁇ 6 bond to form a disaccharide.
- R 11 represents an unsubstituted or substituted C1-30 alkyl group or an unsubstituted or substituted C2-30 alkenyl group.
- the term “unsubstituted” means that the group is only a group serving as a mother nucleus.
- the term “having a substituent” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having a structure different from or the same as that of the mother nucleus.
- the “substituent” is another group substituted with a group serving as a mother nucleus.
- the number of substituents may be one, or two or more. Two or more substituents may be the same or different.
- a C1-30 alkyl group having a substituent is a group in which the parent nucleus is a C1-30 alkyl group, and any one of these hydrogen atoms is substituted with a group having a different structure (“substituent") It is.
- the “C1-30 alkyl group” in R 11 is a saturated hydrocarbon group composed of 1 to 30 carbon atoms.
- the C1-30 alkyl group may be linear or branched.
- Examples of the C1-30 alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, i-propyl group, i -Butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group, heptyl group, octyl, nonyl group, decyl group , Undecyl group, dodecyl group, tridecyl group, tetradec
- the “C2-30 alkenyl group” in R 11 is an unsaturated hydrocarbon group composed of 2 to 30 carbon atoms having at least one carbon-carbon double bond.
- the C2-30 alkenyl group may be linear or branched.
- C2-30 alkenyl groups include vinyl, 1-propenyl, isopropenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3- Pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1-heptenyl group, 6-heptenyl group, 1-octenyl group, 7- Octenyl group, 1-methyl-allyl group, 2-methyl-allyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, octenyl group, nonenyl group,
- Examples of a group that can be a “substituent” of a C1-30 alkyl group or a C2-30 alkenyl group include a hydroxyl group; a mercapto group; an amino group; a nitro group; a halogen atom such as a chlorine atom, a fluorine atom, and a bromine atom; Alkoxy groups such as ethoxy group, isopropoxy group, n-propoxy group, n-butoxy group, isobutoxy group, s-butoxy group and t-butoxy group; aryloxy groups such as phenoxy group and 1-naphthyloxy group; fluoromethoxy Groups, difluoromethoxy groups, trifluoromethoxy groups, 2-chloroethoxy groups, 2,2,2-trichloroethoxy groups, 1,1,1,3,3,3-hexafluoro-2-propoxy groups, etc.
- alkylthio group such as methylthio group and ethylthio group
- aryl such as phenylthio group and 1-naphthylthio group Thio
- anilino group an arylamino group such as a 1-naphthylamino group
- methylamino group, an alkylamino group such as a diethylamino group can be exemplified such as cyano group.
- R 11 is preferably an unsubstituted or substituted C8-20 alkyl group or an unsubstituted or substituted C8-20 alkenyl group.
- the substance (A) is preferably a compound represented by the formula (I) or a salt thereof. Further, it is preferable that R 1 to R 4 in formula (I) are not hydrogen atoms at the same time.
- the substance (A) is represented by the formula (I) [at least one of R 1 to R 4 represents —COR 11 . However, R 11 represents a C12 ⁇ 30 alkenyl group having C12 ⁇ 30 alkyl group or an unsubstituted or substituted group having an unsubstituted or substituted group. ] Or a salt thereof is preferable.
- C12-30 alkyl group examples include dodecyl group, tridecyl group, tetradecyl group (myristyl group), pentadecyl group, hexadecyl group (cetyl group, palmityl group), heptadecyl group, octadecyl group (stearyl group), Nonadecyl group, icosyl group, henicosyl group, triacontyl group and the like can be mentioned.
- substituted C12-30 alkyl group examples include 2-hydroxytridecyl group, 1-hydroxypentadecyl group, 11-hydroxyheptadecyl group, 1-aminoheptadecyl group and the like.
- Examples of the “C12-30 alkenyl group” include a dodecenyl group, a tridecenyl group, a tetradecenyl group, a pentadecenyl group, a hexadecenyl group, a heptadecenyl group, an octadecenyl group, a nonadecenyl group, an icosenyl group, a henicocenyl group, a triaconenyl group, and the like. .
- Examples of the “substituted C12-30 alkenyl group” include 7-hydroxy-8-pentadecenyl group, 1-hydroxy-8-peptadecenyl group, 1-amino-8-heptadecenyl group and the like.
- the substance (A) has the formula (I) [wherein R 1 to R 4 each independently represents a hydrogen atom or —COR 11 , and at least one of R 1 to R 4 represents —COR 11 , R 11 represents an unsubstituted or substituted C1-30 alkyl group or an unsubstituted or substituted C2-30 alkenyl group, and at least one of —COR 11 is represented by R 11 being Represents an unsubstituted or substituted C12-30 alkyl group or an unsubstituted or substituted C12-30 alkenyl group. ] Or a salt thereof is preferable.
- substance (A) examples include ascorbic acid 6-myristate, ascorbic acid 6-palmitate, ascorbic acid 6-stearate, ascorbic acid 2-myristate, ascorbic acid 2-palmitate, ascorbic acid 2 -Stearate, ascorbic acid 2,6-dimyristate, ascorbic acid 2,6-dipalmitate, ascorbic acid 2,6-distearate and the like.
- the salt of the compound represented by the formula (I) and the salt of the compound represented by the formula (II) used in the present invention are not particularly limited as long as they are agro-horticulturally acceptable salts. Examples thereof include alkali metal salts such as sodium salt and potassium salt; alkaline earth metal salts such as calcium salt and magnesium salt.
- the substance (A) used in the present invention can be obtained by a known synthesis method.
- R 1 ⁇ esterification reaction of fatty acid compounds and ascorbic acid for introducing -COR 11 to one of R 4, phosphorus either to introduce -PO 3 H 2 of R 1 ⁇ R 4 Synthesis using an esterification reaction between an acid compound and ascorbic acid, an esterification reaction between a sulfuric acid compound and ascorbic acid for introducing —SO 3 H into any of R 1 to R 4 , and other known reactions can do.
- the substance (A) obtained by the said synthesis method can be refine
- the substances (A) used in the present invention are commercially available, they can also be used.
- the structure of the substance (A) can be identified and confirmed by known analysis means such as IR spectrum, NMR spectrum, mass spectrum, and elemental analysis.
- the substance (A) may be used alone, but is preferably used in combination of at least two.
- the substance (A) is a water-soluble substance selected from the group consisting of a compound represented by the formula (I), a compound represented by the formula (II), and a salt thereof.
- the substance (A) is at least one selected from the group consisting of a compound represented by the formula (Ia), a compound represented by the formula (IIa), and a salt thereof.
- a compound represented by the formula (Ia) a compound represented by the formula (IIa)
- a salt thereof a compound represented by the formula (IIa)
- R 1a to R 4a each independently represents a hydrogen atom, —SO 3 H, —PO 3 H 2 , or a glycosyl group.
- R 5a and R 6a each independently represent a hydrogen atom, —SO 3 H, —PO 3 H 2 , or a glycosyl group.
- R 1b to R 4b each independently represents a hydrogen atom or —COR 11 . At least one of R 1b ⁇ R 4b represents a -COR 11, R 11 is a C2 ⁇ 30 alkenyl group having C1 ⁇ 30 alkyl group or an unsubstituted or substituted group having an unsubstituted or substituted, Preferably, it is an unsubstituted or substituted C12-30 alkyl group or an unsubstituted or substituted C12-30 alkenyl group. ]
- R 5b and R 6b each independently represent a hydrogen atom or —COR 11 . At least one of R 5b and R 6b represents a -COR 11, R 11 is a C2 ⁇ 30 alkenyl group having C1 ⁇ 30 alkyl group or an unsubstituted or substituted group having an unsubstituted or substituted, Preferably, it is an unsubstituted or substituted C12-30 alkyl group or an unsubstituted or substituted C12-30 alkenyl group. ]
- the mass ratio of the fat-soluble substance (A2) to the water-soluble substance (A1) is usually 0.001 to 1000, preferably 0.1 to 10.
- Substance (B) examples of substances (B) that affect the physiological function of plants used in the present invention include herbicides, growth regulators, plant hormones, pathogen-resistant agents, fungicides and insecticides that exhibit phytotoxicity when used at high concentrations. Miticides, repellents, microbial pesticides, fertilizers, surfactants and the like. Of these, at least one selected from the group consisting of fungicides, insecticides, plant growth regulators, and herbicides is preferred.
- the substance (B) is preferably a respiratory inhibitor.
- the substance (B) is preferably a strobilurin-based compound.
- Bactericides include captan, folpette, thiuram, diram, dineb, mannebu, mancozeb, propineb, polycarbamate, chlorothalonil, quintozen, captaphor, iprodione, procymidone, fluoroimide, mepronil, flutolanil, pencyclon, oxycarboxyl, fosetyl aluminum , Propamocarb, hexaconazole, imibenconazole, tebuconazole, difenoconazole, prothioconazole, fenbuconazole, diclobutrazole, vitertanol, microbutanyl, flusilazole, hexaconazole, ethaconazole, fluotrimazole, triadimethone, triadimenol, Flutriaphen, penconazole, diniconazole, cyproconazole, phenalimol, tri
- Pesticides include fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, bamidthione, phentoate, dimethoate, formothion, marathon, trichlorphone, thiomethone, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxydimethone methyl, ethion, salithione, , Pyridafenthion, hosalon, methidathion, sulprophos, chlorfenvinphos, tetrachlorbinphos, dimethylvinphos, propaphos, isofenphos, ethylthiomethone, propenofos, pyracrophos, monocrotophos, azinephosmethyl, aldicarb, mesomil, thiodicarb, carbofuran, carbofuran , Benfuracarb, Frathiocarb, propoxy Organic phosphorus
- Plant hormones include gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7, etc.), auxins (eg, 2,4-D, IAA, NAA, etc.), cytokinins (eg, kinetin, benzyladenine, etc.), abscisic acid, Examples include jasmonic acids, brassinosteroids, strigolactones, salicylic acid and the like.
- Plant growth regulators include, in addition to the above plant hormones, hymexazole, uniconazole, trinexapack, daminozide, cyanamide and the like.
- Fertilizers include nitrogenous fertilizer, phosphate fertilizer, potash fertilizer, calcareous fertilizer, mafic fertilizer, siliceous fertilizer, trace element fertilizer, moving substance fertilizer, plant fertilizer and the like. If the concentration of water-soluble components in the fertilizer is too high, the plant may be damaged by fertilizers such as roots and leaves withering and withering. In addition, when a large amount of a specific type of fertilizer such as ammonium sulfate is used, plant growth may be damaged through acidification of the soil.
- Surfactant is used as an auxiliary component for agricultural chemical preparations, as an active ingredient for some insecticides and acaricides, or as a spreading agent.
- Surfactants include alkylphenyl ethers added with polyoxyethylene, alkyl ethers added with polyoxyethylene, higher fatty acid esters added with polyoxyethylene, sorbitan higher fatty acid esters added with polyoxyethylene, and polyoxyethylene.
- Nonionic surfactants such as added tristyrylphenyl ether; sulfates of alkylphenyl ethers added with polyoxyethylene, alkylbenzene sulfonates, sulfates of higher alcohols, alkylnaphthalene sulfonates, polycarboxylic acids
- Anionic surfactants such as salts, lignin sulfonates, alkylnaphthalene sulfonate formaldehyde condensates, isobutylene-maleic anhydride copolymers; Id, methyl, polyoxyethylene, alkylammonium chloride, alkyl, N-methylpyridium bromide, mono- or dialkylmethylated ammonium chloride, alkylpentamethylpropylenediamine dichloride, alkyldimethylbenzalkonium chloride, benzethonium chloride, etc.
- amphoteric surfactants such as dialkyldiaminoethylbetaine, alkyldimethylbenzylbetaine, dialkyldiaminoethylglycine, and alkyldimethylbenzylglycine;
- the pharmaceutical composition according to the present invention can be obtained by mixing the substance (A) and the substance (B) by a known method.
- the mass ratio of the substance (B) to the substance (A) is usually 0.0001 to 100, preferably 0.001 to 100, more preferably 0.01 to 10.
- the pharmaceutical composition according to the present invention can be prepared into preparations such as wettable powders, emulsions, aqueous solvents, granular wettable powders, powders and tablets.
- the preparation method to a formulation is not specifically limited, A well-known preparation method can be employ
- the method of applying the pharmaceutical composition of the present invention to a plant is not particularly limited, and known application methods can be employed in the field of agriculture and horticulture. Moreover, the method of application to a plant can be appropriately determined according to the type of plant to be targeted. For example, application by foliage spraying, dipping treatment, soil irrigation, seed treatment, hydroponic solution treatment, smoking treatment, room temperature fuming treatment, etc. can be mentioned as preferred.
- the pharmaceutical composition of the present invention can be used without being limited by cultivation forms such as soil cultivation and hydroponics. In addition, excellent effects can be obtained even when used in special environments such as growth point culture.
- the application amount of the pharmaceutical composition of the present invention can be appropriately determined according to weather conditions, formulation form, application time, application method, application place, disease to be controlled, target crop, and the like.
- the plant to which the pharmaceutical composition of the present invention can be applied is not particularly limited, and may be either an edible plant or a non-edible plant.
- grains such as rice, wheat, corn, beans such as soybean, adzuki, peanut, fruits such as citrus, apple, pear, grape, peach, vegetables such as tomato, lettuce, cabbage, onion, leek, peppers, Cucumbers, watermelons, melons, pumpkins and other potatoes, potatoes, sweet potatoes, potatoes, carrots, radish and other root vegetables, cotton, sugar beet, hops, sugar cane, rubber, coffee, tobacco, tea, etc.
- grasses such as timosi and orchardgrass, and grasses such as bentgrass and mulberry.
- the stress targeted by the pharmaceutical composition of the present invention includes biological stress caused by plant viruses, phytopathogenic bacteria, phytopathogenic fungi, pests or weeds; high temperature, low temperature, high illuminance, low illuminance, overhumidity, dryness, salinity Physical or chemical stress due to acid, pesticides, chemicals or heavy metals.
- the plant virus that causes stress is not particularly limited.
- geminiviruses with single-stranded DNA as genome cauliflower mosaic virus with double-stranded DNA as genome, tobacco mosaic virus with single-stranded RNA as genome, tomato bushy stunt virus, double-stranded RNA as genome
- the rice rug stunt virus etc. which it has can be mentioned as a preferable thing.
- Phytopathogenic bacteria that cause stress are not particularly limited.
- rice seedling blight (Burkholderia plantarii), brown streak (Acidovorax avenae), blight blight (Burkholderia glumae), leaf blight (Xanthomonas campestris pv. Oryzae), cucumber spotted bacterial disease (Pseudomonas lachrymans) And Chinese cabbage soft rot (Erwinia carotovora).
- Phytopathogenic fungi causing stress are not particularly limited.
- rice blast (Pyricularia oryzae), idiot seedling (Gibberella fujikuroi), sesame leaf blight (Cochliobolus miyabeanus), wheat powdery mildew (Erysiphe graminisspf.sp.tritici), red mold (Gibberella zeae) , Red rust (Puccinia recondita), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), barley bare smut (Ustilago tritici), cucumber powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonosp) ), Vine blight (Mycosphaerella melonis), vine split disease (Fusarium oxysporum), gray mold (Botrytis cinerea), anthracnose (Colle
- the pests that cause stress are not particularly limited. , Corn borer, European corn borer, white-faced butterfly, genus Heliotis, genus Helicoberpa, agrotis, iga, scallop, white butterfly, tobacco bad worm, stag beetle, scallop Hemiptera pests, for example, aphids such as phantom aphid, wheat aphid, peach aphid, cotton aphid, bean aphid; whitefly, tobacco whitefly, white leaf whitefly, whitefly Hawksbill beetle, sorghum scale, stag beetle, pterfly lice, pear beetle, flying planthopper, brown planthopper, white planthopper, leafhopper, etc .; Coleopterous pests, e.g., Kizunami beetle, cucumber potato beetle, Colorado potato beetle, mustard beetle, rice weevil, weevil, azuki
- Weeds that cause stress are not particularly limited, but grasses such as Inobie, Yasei Sorghum, Akino no Ezologosa, Enocologosa, Aedes albopictus, Prunus terrestris, Barnyard grass, Oshiba, Suzunokatabira, Inobie, etc., Onamomi, Ragosa Pteris arena, weeping weeds such as oleander, crocodile, chitinose, sendangusa, mugwort, butterflies, psyllium, tadpole, tuna, red-footed beetle, yamgra, ichibi, chimemegusa, red-footed moth, red-footed moth, red-footed moth, red-footed moth American King Deer, White clover, Ebisu rush, Firefly, Matsubai, Sphagnum, Kogi, Azena, Mizohakobe,
- glyphosate-tolerant weeds include Amaranthaceae (Amaranthaceae), Ragweed (Asteraceae) and Kenashihimemukashimugigi.
- ⁇ High and low temperatures that cause stress are not particularly limited.
- high-temperature damage and low-temperature damage that reduce the growth and quality of rice high-temperature damage that reduces the fruiting rate of solanaceous crops such as tomatoes
- high-temperature damage that tends to occur especially in tunnel and greenhouse cultivation such as lettuce
- Western turf High-temperature damage that inhibits the growth of fruit
- frost and frost damage of fruit trees such as tea and citrus fruits.
- ⁇ Overhumidity and drying that cause stress are not particularly limited.
- crop growth failure due to excessive rainfall, irrigation, or excessive moisture due to poorly drained soil, reduced resistance to disease, or lack of rainfall, irrigation, or drying due to sandy soil Such as wilting.
- ⁇ Soil properties that cause stress are not particularly limited.
- crop growth failure in soil containing salt, acidic soil or alkaline soil are not particularly limited.
- the effects on growth failure in salt-containing soil and acidic soil, especially on the growth failure of crops that are vulnerable to acidic soil such as spinach, pea, broad bean, onion, asparagus, lettuce, burdock, etc. has the effect of improving the yield and quality.
- Chemical substances that cause stress are not particularly limited, but herbicides, growth regulators, plant hormones, disease resistance inducers, fungicides such as fungicides, insecticides, acaricides, fertilizers, surfactants, other Examples include at least one compound selected from allelopathic substances produced by plants and affecting crops.
- the pesticide that causes stress is not particularly limited, and examples thereof include those exemplified as substances that affect the physiological functions of plants.
- the phytotoxicity causing stress is, for example, phytotoxicity that occurs when the concentration exceeds the standard of use or when it is applied to non-applicable crops, and phytotoxicity that occurs under high temperature conditions or strong light conditions. By suppressing these phytotoxicity by this invention, it is also possible to make the application range of an agrochemical wider than what was applied conventionally.
- the heavy metal that causes stress is not particularly limited, and examples thereof include iron, zinc, copper, manganese, nickel, cobalt, tin, chromium, lead, cadmium, mercury, and arsenic.
- the pharmaceutical composition according to the present invention When the pharmaceutical composition according to the present invention is applied to a plant, resistance to stress can be imparted to the plant, and further, phytotoxicity due to the agricultural chemicals of the plant can be reduced.
- an agrochemical which is a target for reducing phytotoxicity those containing at least one selected from the group consisting of fungicides, insecticides, plant growth regulators and herbicides are preferred.
- an agrochemical which is a target for reducing phytotoxicity those containing the substance (B) which affects the physiological function of the plant described above are preferable.
- the formulation of the preparation is not limited to the examples of the preparation, and can be changed in a wide range.
- the part in a formulation example shows a weight part.
- Formulation Example 4 Flowable Agent Substance (A) 5 parts Substance (B) 5 parts Polyoxyethylene aryl phenyl ether ether 2 parts Dialkylsulfosuccinate sodium salt 0.5 parts Glycerin 5 parts Xanthan gum 0.3 part Water 82. Two or more parts are mixed and wet pulverized to obtain a flowable agent.
- Test Example 1 Test for Reducing Effect of High Temperature Damage on Arabidopsis thaliana N, N-dimethylformamide solutions were prepared according to the formulations shown in Tables 3 to 6 and used as pharmaceutical compositions 1 to 12 for testing. Ten seeds of Arabidopsis seed sterilized on the hydroponics sponge pieces were sown and grown for 14 days at 22 ° C., 16 hours in the light, and 8 hours in the dark to prepare test seedlings. 100 ⁇ l of the above pharmaceutical composition was dropped onto the seedling of the seedling and grown for 2 days at 22 ° C., 16 hours in the light, and 8 hours in the dark. Thereafter, the seedlings were allowed to stand at 35 ° C. in a dark place for 1 hour and then left at 45 ° C.
- Test Example 2 Evaluation Test for Reducing Effect of Low Temperature Damage on Eggplant Eggplants (variety: Senryo 2, No. 3 and 3) grown in the greenhouse until the 4-6 leaf stage were prepared.
- Ascorbic acid palmitate 30% granule wettable powder and pyraclostrobin dissolved in 40% with N, N-dimethylformamide are diluted with tap water to the concentrations shown in Table 7 and sufficient for the whole seedling. Sprayed. After air drying, the cells were grown for 1 day at 18 ° C. in a light place for 16 hours and at 13 ° C. in a dark place for 8 hours. Subsequently, it was grown for 15 days under conditions of 16 hours in the light at 13 ° C. and 8 hours in the dark at 8 ° C.
- Test Example 3 Evaluation Test for Reducing Effect of High Temperature Damage on Tomatoes Tomatoes (variety: Momotaro, 2 series) grown up to the 4th leaf stage in a greenhouse were prepared.
- the degree of necrosis caused by the influence of high temperature was evaluated by an eleven-grade disorder index from 0 (no necrosis) to 10 (death).
- Test Example 7 Evaluation Test for Reduction Effect of Acidic Damage on Soybean Soybean (cultivar: Enrei, 2 series) that was hydroponically grown up to the second leaf stage with 100 ml of Kolben was prepared. Ascorbyl palmitate 30% granule wettable powder and pyraclostrobin dissolved in 40% with N, N-dimethylformamide are diluted with tap water to the concentrations shown in Table 13 and sprayed to the whole seedling. did. The hydroponic solution was adjusted to pH 4 with 1N hydrochloric acid when 2 days had elapsed after spraying, and the soybean was continuously hydroponically grown. At 11 days after spraying, soybean damage was investigated.
- Test Example 8 Evaluation Test for Reduction Effect of Salt Damage on Cucumber Cucumber (variety: Sagamihanjiro, 2) which was hydroponically grown to 1.5 leaf stage in a greenhouse was prepared.
- a 30% granule wettable powder of ascorbyl palmitate and a commercial product containing the substance (B) described in Table 14 were diluted with tap water to the concentrations described in Table 14, and a sufficient amount was sprayed over the entire seedling. . After air drying, it was cultivated in a greenhouse with normal irrigation. Cultivated by switching to irrigation with a 0.1% sodium chloride aqueous solution from the elapse of 3 days after spraying. The raw weight of the above-ground part was measured when 20 days passed after spraying. The failure reduction rate was calculated from the following equation.
- Obstacle reduction rate ((raw weight of each treated area)-(raw weight of non-treated area)) / ((Raw weight of normal irrigation zone)-(Raw weight of untreated zone)) x 100 The results are shown in Table 14.
- Test Example 9 Evaluation Test for Reduction Effect of Salt Damage on Cucumber A cucumber (cultivar: Sagami Hansakusei, 2 series) that was hydroponically grown to the second leaf stage in a greenhouse was prepared. 30% granular wettable powder of ascorbyl palmitate and pyraclostrobin adjusted to 40% with N, N-dimethylformamide are diluted with tap water to the concentrations shown in Table 15 and sprayed to the whole seedling. did. After air drying, it was cultivated in a greenhouse with normal irrigation. Cultivated by switching to a submerged state of a 0.1% sodium chloride aqueous solution with a depth of 2 cm from 2 days after spraying.
- Test Example 10 Evaluation Test for Reduction of Salt Damage to Soybean Soybean (cultivar: Enrei, 2 series) that was hydroponically grown to the second leaf stage in a greenhouse was prepared. Ascorbyl palmitate 30% granule wettable powder and pyraclostrobin adjusted to 40% with N, N-dimethylformamide were diluted with tap water to the concentrations shown in Table 16, and a sufficient amount was sprayed over the entire seedling. After air drying, it was cultivated in a greenhouse with normal irrigation. Cultivated by switching to a submerged state of a 0.1% sodium chloride aqueous solution with a depth of 2 cm from 2 days after spraying.
- Test Example 11 Test for reducing effects of phytotoxicity on tomato An N, N-dimethylformamide solution was prepared according to the formulation shown in Table 17 and used as a test pharmaceutical composition. Tomato seedlings (variety: Momotaro) grown to the 4th leaf stage in the greenhouse were prepared. The above-mentioned pharmaceutical composition was sprayed onto the stem and leaves of the tomato seedling so that the liquid dripped. After air drying, it was cultivated under normal temperature and humidity conditions in March of Japan. At 7 days after spraying, phytotoxicity such as leaf browning and elongation suppression was investigated. The phytotoxicity was evaluated with 11 phytotoxicity indices ranging from 0 (no injury) to 10 (dead).
- the phytotoxicity reduction rate compared with the treatment section of only solvent DMF was calculated by the following formula.
- Chemical hazard reduction rate ((chemical hazard index of solvent only treatment area)-(phytotoxicity index of each treatment area)) / (Phytotoxicity index of solvent-only treatment zone) x 100 The results are shown in Table 17.
- Test Example 13 Effect of reducing disease stress on rice Rice seedlings (variety: Koshihikari, 4 leaf stage, 5 lines, 1 line) were prepared. A commercial agent containing 96 mg of probenazole was applied to the water surface. 30% granular wettable powder of ascorbyl palmitate was diluted with tap water to the concentrations shown in Table 19, and a sufficient amount was sprayed over the entire seedlings after 2 days from application to the water surface. The rice blast fungus was inoculated 1 day after air drying. At 11 days after inoculation, the blast area was investigated.
- the incidence index per strain is 0 for no disease, 1 for an area less than 25%, 2 for an area of 25% to less than 50%, 3 for an area of 50% to less than 75%, and 4 for an area of 75% or more. It was evaluated in five stages.
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Abstract
Description
〔1〕 式(I)で表される化合物、式(II)で表される化合物、およびそれらの塩からなる群から選ばれる少なくとも一つの物質(A)と、
植物の生理作用に影響を及ぼす物質(B)と
を含有する植物へのストレスを軽減する薬剤組成物。
[式(I)中、R1~R4はそれぞれ独立して、水素原子、-SO3H、-PO3H2、グリコシル基または-COR11を示す。R11は、無置換の若しくは置換基を有するC1~30アルキル基または無置換の若しくは置換基を有するC2~30アルケニル基を示す。]
[式(II)中、R5およびR6はそれぞれ独立して、水素原子、-SO3H、-PO3H2、グリコシル基または-COR11を示す。R11は、無置換の若しくは置換基を有するC1~30アルキル基または無置換の若しくは置換基を有するC2~30アルケニル基を示す。]
〔3〕 物質(B)が、呼吸阻害剤である、〔1〕に記載の組成物。
〔4〕 物質(B)が、ストロビルリン系化合物である、〔1〕に記載の組成物。
〔6〕 物質(A)が、式(I)[ただし、R1~R4のうち少なくとも一つは-COR11を示し、R11は、無置換の若しくは置換基を有するC12~30アルキル基または無置換の若しくは置換基を有するC12~30アルケニル基を示す。]で表される化合物またはその塩である、〔1〕に記載の組成物。
〔7〕 物質(A)が、式(I)[ただし、R1~R4はそれぞれ独立して、水素原子、または-COR11を示し、且つR1~R4のうち少なくとも一つは-COR11を示す。R11は、無置換の若しくは置換基を有するC1~30アルキル基または無置換の若しくは置換基を有するC2~30アルケニル基を示す。-COR11のうち少なくとも一つはその中のR11が、無置換の若しくは置換基を有するC12~30アルキル基または無置換の若しくは置換基を有するC12~30アルケニル基を示す。]で表される化合物またはその塩である、〔1〕に記載の組成物。
〔9〕 前記ストレスが、植物ウイルス、植物病原細菌、植物病原糸状菌、害虫若しくは雑草による生物的ストレス;または、高温、低温、高照度、低照度、過湿、乾燥、塩分、酸性、農薬、化学物質若しくは重金属による物理的若しくは化学的ストレスのいずれか少なくとも一つである、〔8〕に記載の方法。
物質(A)は、式(I)で表される化合物、式(II)で表される化合物、およびそれらの塩からなる群から選ばれる少なくとも一つである。
式(I)中、R1~R4はそれぞれ独立して、水素原子、-SO3H、-PO3H2、グリコシル基または-COR11を示す。
式(II)中、R5およびR6はそれぞれ独立して、水素原子、-SO3H、-PO3H2、グリコシル基または-COR11を示す。
ここで、「無置換の」の用語は、該基が母核となる基のみであることを意味する。なお、「置換基を有する」との記載がなく母核となる基の名称のみで記載しているときは、別段の断りがない限り「無置換の」の意味である。
一方、「置換基を有する」の用語は、母核となる基のいずれかの水素原子が、母核と異なる若しくは同じ構造の基で置換されていることを意味する。従って、「置換基」は、母核となる基に置換された他の基である。置換基は一つであってもよいし、二つ以上であってもよい。二つ以上の置換基は同じのものであってもよいし、異なるものであってもよい。例えば、置換基を有するC1~30アルキル基は、母核となる基がC1~30アルキル基で、これのいずれかの水素原子が異なる構造の基(「置換基」)で置換されているものである。
上記R11は、無置換の若しくは置換基を有するC8~20アルキル基または無置換の若しくは置換基を有するC8~20アルケニル基が好ましい。
また、物質(A)は、式(I)[R1~R4のうち少なくとも一つは-COR11を示す。ただし、R11は、無置換の若しくは置換基を有するC12~30アルキル基または無置換の若しくは置換基を有するC12~30アルケニル基を示す。]で表される化合物またはその塩であることが好ましい。
なお、「C12~30アルキル基」としては、例えば、ドデシル基、トリデシル基、テトラデシル基(ミリスチル基)、ペンタデシル基、ヘキサデシル基(セチル基、パルミチル基)、ヘプタデシル基、オクタデシル基(ステアリル基)、ノナデシル基、イコシル基、ヘンイコシル基、トリアコンチル基などが挙げられる。
「置換基を有するC12~30アルキル基」としては、例えば、2-ヒドロキシトリデシル基、1-ヒドロキシペンタデシル基、11-ヒドロキシヘプタデシル基、1-アミノヘプタデシル基などが挙げられる。
「置換基を有するC12~30アルケニル基」としては、例えば、7-ヒドロキシ-8-ペンタデセニル基、1-ヒドロキシ-8-ペプタデセニル基、1-アミノ-8-ヘプタデセニル基などが挙げられる。
なお、物質(A)の構造は、IRスペクトル、NMRスペクトル、マススペクトル、元素分析等の公知の分析手段により、同定、確認することができる。
[式(Ib)中、R1b~R4bはそれぞれ独立して、水素原子、または-COR11を示す。R1b~R4bのうち少なくとも一つは-COR11を示し、R11は、無置換の若しくは置換基を有するC1~30アルキル基または無置換の若しくは置換基を有するC2~30アルケニル基を、好ましくは無置換の若しくは置換基を有するC12~30アルキル基または無置換の若しくは置換基を有するC12~30アルケニル基を示す。]
[式(IIb)中、R5bおよびR6bはそれぞれ独立して、水素原子、または-COR11を示す。R5bおよびR6bのうち少なくとも一つは-COR11を示し、R11は、無置換の若しくは置換基を有するC1~30アルキル基または無置換の若しくは置換基を有するC2~30アルケニル基を、好ましくは無置換の若しくは置換基を有するC12~30アルキル基または無置換の若しくは置換基を有するC12~30アルケニル基を示す。]
本発明に用いられる植物の生理作用に影響を及ぼす物質(B)としては、除草剤、成長調節剤、植物ホルモン、病原菌に対する抵抗性誘導剤、使用濃度を高くすると薬害を示す殺菌剤、殺虫剤、殺ダニ剤、忌避剤、微生物農薬、肥料、界面活性剤などが挙げられる。これらのうち、殺菌剤、殺虫剤、植物成長調整剤、および除草剤からなる群から選ばれる少なくとも一つが好ましい。また物質(B)は呼吸阻害剤であることが好ましい。さらに物質(B)はストロビルリン系化合物であることが好ましい。
このうちで、クレソキシムメチル、トリフロキシストロビン、アゾキシストロビン、ピラクロストロビン、オリサストロビン等のストロビルリン系殺菌剤が特に好ましい。
このうちで、イミダクロプリド、アセタミプリド、ニテンピラム、チアクロプリド、クロチアニジン、チアメトキサム、ジノテフラン、ニチアジン等のネオニコチノイド系殺虫剤、およびクロルフェナピル、ピメトロジン、ピリダベン、フェンピロキシメート、トルフェンピラド、テブフェンピラド、シエノピラフェン、シフルメトフェン、フルアクリピリム、アセキノシル、フェナザキン等の呼吸阻害効果を有する殺虫剤若しくは殺ダニ剤が特に好ましい。
また、本発明に係る薬剤組成物は、水和剤、乳剤、水溶剤、顆粒水和剤、粉剤、錠剤などの製剤に調製することができる。製剤への調製方法は、特に制限されず、剤形に応じて公知の調製方法を採用することができる。
鱗翅目害虫、例えば、ヨトウガ、アワヨトウ、ハスモンヨトウ、タマナヤガ、チャノコカクモンハマキ、チャハマキ、モモシンクイガ、ナシヒメシンクイ、ミカンハモグリガ、チャノホソガ、キンモンホソガ、マイマイガ、チャドクガ、ニカメイガ、コブノメイガ、ヨーロピアンコーンボーラー、アメリカシロヒトリ、スジマダラメイガ、ヘリオティス属、ヘリコベルパ属、アグロティス属、イガ、アワノメイガ、オオモンシロチョウ、タバコバッドワーム、コナガ、ネキリムシ(ヤガ科の一種)など;
半翅目害虫、例えば、ニセダイコンアブラムシ、ムギクビレアブラムシ、モモアカアブラムシ、ワタアブラムシ、マメクロアブラムシ等のアブラムシ類;オンシツコナジラミ、タバココナジラミ、シルバーリーフコナジラミ等のコナジラミ類;ホシカメムシ、ホソヘリカメムシ、アオクサカメムシ、ヤノネカイガラムシ、クワコナカイガラムシ、ナシキジラミ、ナシグンバイムシ、トビイロウンカ、ヒメトビウンカ、セジロウンカ、ツマグロヨコバイなど;
甲虫目害虫、例えば、キスジノミハムシ、ウリハムシ、コロラドハムシ、マスタードビートル、イネミズゾウムシ、コクゾウムシ、アズキゾウムシ、マメコガネ、ヒメコガネ、コーンルートワーム、ジアブロティカ属、タバコシバンムシ、ヒラタキクイムシ、マツノマダラカミキリ、ゴマダラカミキリ、アグリオティス属、ニジュウヤホシテントウ、コクヌスト、ワタミゾウムシなど;
直翅目害虫、例えば、イナゴ、トノサマバッタなど;
アザミウマ目害虫、例えば、ミナミキイロアザミウマ、チャノキイロアザミウマ、ネギアザミウマ、ヒラズハナアザミウマなど;
双翅目害虫、例えば、ウリミバエ、ミカンコミバエ、イネハモグリバエなど;
ダニ類、例えば、ナミハダニ、ニセナミハダニ、カンザワハダニ、ミカンハダニ、リンゴハダニ、ヒメハダニ等のハダニ類;ミカンサビダニ、リンゴサビダニ、チャノホコリダニ、ロビンネダニなど;
等が挙げられる。この中で適用が特に好ましい害虫としては、植物ウイルスを媒介するアブラムシ類、コナジラミ類、アザミウマ類、ハダニ類などが挙げられる。
ストレスの原因になる農薬は特に限定されず、例えば、植物の生理作用に影響を及ぼす物質として例示したものが挙げられる。
ストレスの原因になる薬害は、例えば、使用規準を超えた濃度や適用外の作物に処理した場合の薬害、さらに高温条件や強光条件下で生じる薬害などである。本発明によりこれらの薬害が抑制されることで、農薬の適用範囲を従来適用されていたものより広くすることも可能である。
アスコルビン酸、イソアスコルビン酸またはデヒドロアスコルビン酸を公知の反応によってエステル化、グリコシル化、または酸化させることによって、各種の物質(A)を合成した。合成した物質(A)の一部を表1および表2に示す。表1中のR1~R4は、式(I)中のR1~R4に対応するものである。表2中のR5およびR6は、式(II)中のR5およびR6に対応するものである。
(製剤実施例1)水和剤
物質(A) 10部
物質(B) 10部
ホワイトカーボン 20部
ケイソウ土 52部
アルキル硫酸ソーダ 8部
以上を均一に混合、微細に粉砕して、水和剤を得る。
物質(A) 10部
物質(B) 10部
キシレン 55部
ジメチルホルムアミド 15部
ポリオキシエチレンフェニルエーテル 10部
以上を混合、溶解して乳剤を得る。
物質(A) 5部
物質(B) 5部
タルク 37部
クレー 36部
ベントナイト 10部
アルキル硫酸ソーダ 7部
以上を均一に混合して微細に粉砕後、造粒して粒剤を得る。
物質(A) 5部
物質(B) 5部
ポリオキシエチレンアリールフェニルエーテルエーテル 2部
ジアルキルスルホサクシネートナトリウム塩 0.5部
グリセリン 5部
キサンタンガム 0.3部
水 82.2部
以上を混合し、湿式粉砕して、フロアブル剤を得る。
物質(A) 15部
物質(B) 15部
無機担体 70部
以上を均一に混合して微粉に粉砕後、造粒して顆粒水和剤を得る。
表3~6に示す処方にてN,N-ジメチルホルムアミド溶液を調製し、試験用の薬剤組成物1~12とした。
水耕栽培用スポンジ片の上に表面消毒したシロイヌナズナの種子を10粒ずつ播いて、22℃、明所16時間、暗所8時間で14日間育成させて、試験用幼苗を用意した。
該幼苗の株元に上記薬剤組成物100μlを滴下し、22℃、明所16時間、暗所8時間で2日間育成させた。
その後、該幼苗を、35℃、暗所に1時間放置し、次いで45℃、暗所に2時間放置し、幼苗に高温障害が生じるようにした。
前記幼苗を、22℃、明所16時間、暗所8時間の育成条件に戻し、4日経過時に高温障害の状態を調査した。
0(障害なし)~5(本葉の萎れ2枚以上)の6段階の高温障害指数で評価した。溶媒DMFのみの処理区(薬剤組成物6)と比較した高温障害軽減率(%)を次式により算出した。
高温障害軽減率=((溶媒のみ処理区の障害指数)-(各処理区の障害指数))
/(溶媒のみ処理区の障害指数) ×100
その結果を表3~6に示す。
温室内で4-6葉期まで育成したナス(品種:千両2号、3連)を用意した。
アスコルビン酸パルミテート30%顆粒水和剤と、N,N-ジメチルホルムアミドで40%に溶解したピラクロストロビンとを、水道水で表7に記載した濃度となるように希釈して苗全体に十分量を散布した。風乾後、18℃で明所16時間および13℃で暗所8時間の条件下で1日間生育させた。次いで、13℃で明所16時間および8℃で暗所8時間の条件下で15日間生育させた。15日間経過時に障害程度を調査した。
処理後の展開葉で変色した部分の面積を計測し、0(変色なし)、1(全体の1/4まで変色)、2(全体の1/2まで変色)、3(全体の1/2以上変色)の4段階の障害指数で評価し、障害軽減率を下式で算出した。
低温障害軽減率=((無処理区の障害指数)-(各処理区の障害指数))
/(無処理区の障害指数) ×100
その結果を表7に示す。
温室内で4葉期まで育成したトマト(品種:桃太郎、2連)を用意した。
アスコルビン酸パルミテート30%顆粒水和剤と表8に記載の物質(B)を含有する市販剤を、水道水で表8に記載した濃度に希釈して苗全体に十分量を散布した。風乾後、明条件40℃16時間、暗条件30℃8時間のサイクルで栽培した。散布後4日経過時に障害程度を調査した。
障害は高温による影響で生じた壊死の程度を、0(壊死なし)~10(枯死)の11段階の障害指数で評価した。これから次式により障害軽減率を算出した。
障害軽減率=((溶媒のみ処理区の障害指数)-(各処理区の障害指数))
/(溶媒のみ処理区の障害指数) ×100
その結果を表8に示す。
温室内で2葉期まで育成したトマト(品種:麗容、2連)を用意した。
アスコルビン酸パルミテート30%顆粒水和剤とN,N-ジメチルホルムアミドで40%に溶解したピラクロストロビンとを、水道水で表9に記載した濃度に希釈して苗全体に十分量を散布した。風乾後、夏季炎天下の強光に当てた。散布後4日経過時に障害程度を調査した。
光による影響で生じた壊死の程度を、0(壊死なし)~10(枯死)の11段階の障害指数で評価した。これから次式により障害軽減率を算出した。
強光障害軽減率=((無処理区の障害指数)-(各処理区の障害指数))
/(無処理区の障害指数) ×100
その結果を表9に示す。
温室内で2葉期まで育成したキュウリ(品種:相模半白節成、2連)を用意した。
アスコルビン酸パルミテートの30%顆粒水和剤と、N,N-ジメチルホルムアミドで40%に溶解したピラクロストロビンとを、水道水で表10に記載した濃度に希釈して十分量を散布した。散布後2日経過時から子葉の直下まで湛水状態にし、散布後11日経過時にキュウリの地上部と根部それぞれの生重量を測定した。これから次式により障害軽減率を算出した。
冠水障害軽減率=((各処理区の生重量)-(無処理区の生重量))
/(無処理区の生重量) ×100
結果を表10に示す。
温室内で2葉期まで育成したダイズ(品種:エンレイ、2連)を用意した。
アスコルビン酸パルミテートの30%顆粒水和剤と、N,N-ジメチルホルムアミドで40%に溶解したピラクロストロビンとを、水道水で表11に記載した濃度に希釈して十分量を散布した。散布後2日経過時から子葉の直下まで湛水状態にし、散布後11日経過時にダイズの地上部と根部それぞれの生重量を測定した。これから次式により障害軽減率を算出した。
冠水障害軽減率=((各処理区の生重量)-(無処理区の生重量))
/(無処理区の生重量) ×100
結果を表11に示す。
100mlのコルベンにて2葉期まで水耕育成したキュウリ(品種:相模半白節成、2連)を用意した。
アスコルビン酸パルミテートの30%顆粒水和剤と、N,N-ジメチルホルムアミドで40%に溶解したピラクロストロビンとを、水道水で表12に記載した濃度に希釈して苗全体に十分量を散布した。散布後2日経過時に水耕液を1N塩酸でpH4に調整し、該キュウリを継続して水耕育成した。散布後17日経過時にキュウリの葉齢を調査した。これから次式により障害軽減率を算出した。
酸性障害軽減率=((各処理区の葉齢)-(無処理区の葉齢))
/(無処理区の葉齢) ×100
結果を表12に示す。
100mlのコルベンにて2葉期まで水耕育成したダイズ(品種:エンレイ、2連)を用意した。
アスコルビン酸パルミテートの30%顆粒水和剤と、N,N-ジメチルホルムアミドで40%に溶解したピラクロストロビンとを、水道水で表13に記載した濃度に希釈して苗全体に十分量を散布した。散布後2日経過時に水耕液を1N塩酸でpH4に調整し、該ダイズを継続して水耕育成した。散布後11日経過時にダイズの障害を調査した。
壊死の程度を、0(壊死なし)~10(枯死)の11段階の障害指数で評価した。これから次式により障害軽減率を算出した。
酸性障害軽減率=((無処理区の障害指数)-(各処理区の障害指数))
/(無処理区の障害指数) ×100
結果を表13に示す。
温室内で1.5葉期まで水耕育成したキュウリ(品種:相模半白、2連)を用意した。
アスコルビン酸パルミテートの30%顆粒水和剤と、表14に記載の物質(B)を含有する市販品とを、水道水で表14に記載した濃度に希釈して苗全体に十分量を散布した。風乾後、温室で通常の潅水で栽培した。散布後3日経過時から0.1%塩化ナトリウム水溶液による潅水に切り替えて栽培した。散布後20日経過時に地上部の生重量を測定した。これから次式により障害軽減率を算出した。なお、薬剤散布せずに通常の潅水で栽培を20日間行ったものを通常潅水区と表記する。
障害軽減率=((各処理区の生重量)-(無処理区の生重量))
/((通常潅水区の生重量)-(無処理区の生重量)) ×100
結果を表14に示す。
温室内で2葉期まで水耕育成したキュウリ(品種:相模半白節成、2連)を用意した。
アスコルビン酸パルミテートの30%顆粒水和剤と、N,N-ジメチルホルムアミドで40%に調整したピラクロストロビンとを、水道水で表15に記載した濃度に希釈して苗全体に十分量を散布した。風乾後、温室で通常の潅水で栽培した。散布後2日経過時から2cm深の0.1%塩化ナトリウム水溶液の湛水状態に切り替えて栽培した。散布後11日経過時に地上部および根部それぞれの生重量を測定した。これから次式により障害軽減率を算出した。
塩障害軽減率=((各処理区の生重量)-(無処理区の生重量))
/(無処理区の生重量) ×100
結果を表15に示す。
温室内で2葉期まで水耕育成したダイズ(品種:エンレイ、2連)を用意した。
アスコルビン酸パルミテートの30%顆粒水和剤と、N,N-ジメチルホルムアミドで40%に調整したピラクロストロビンを水道水で表16に記載した濃度に希釈して苗全体に十分量を散布した。風乾後、温室で通常の潅水で栽培した。散布後2日経過時から2cm深の0.1%塩化ナトリウム水溶液の湛水状態に切り替えて栽培した。散布後11経過時に地上部および根部それぞれの生重量を測定した。これから次式により障害軽減率を算出した。
障害軽減率=((各処理区の生重量)-(無処理区の生重量))
/(無処理区の生重量) ×100
結果を表16に示す。
表17に示す処方にてN,N-ジメチルホルムアミド溶液を調製し、試験用の薬剤組成物とした。
温室内で4葉期まで育成したトマト苗(品種:桃太郎)を用意した。
該トマト苗の茎葉部に、液が垂れ落ちる程の量の上記薬剤組成物を散布した。風乾後、日本の3月の平年の温湿度条件下において栽培した。散布後7日経過時に葉の褐変程度や伸長抑制などの薬害を調査した。
薬害は0(障害なし)~10(枯死)の11段階の薬害指数で評価した。
溶媒DMFのみの処理区と比較した薬害軽減率を次式により算出した。
薬害軽減率=((溶媒のみ処理区の薬害指数)-(各処理区の薬害指数))
/(溶媒のみ処理区の薬害指数) ×100
その結果を表17に示す。
イネ(品種:コシヒカリ、10連)の苗を用意した。アスコルビン酸パルミテートの30%顆粒水和剤と、N,N-ジメチルホルムアミドで5%に調整したピラクロストロビンとを、水道水で表18に記載した濃度に希釈し、これらの十分量を苗全体に散布した。風乾後1日経過時にいもち病菌を接種した。接種後11日経過時にいもち病斑数を調査した。これから防除価を次式により算出した。
防除価=((無処理区の病斑数)-(各処理区の病斑数))
/(無処理区の病斑数) ×100
その結果を表18に示す。
イネ(品種:コシヒカリ、4葉期、5株1連)の苗を用意した。プロベナゾール96mgを含有する市販剤を水面施用した。アスコルビン酸パルミテートの30%顆粒水和剤を水道水で表19に記載した濃度に希釈し、十分量を、水面施用後2日経過時に苗全体に散布した。風乾後1日経過時にいもち病菌を接種した。接種後11日経過時にいもち発病面積を調査した。1株当たりの発病指数として、発病なしを0、発病面積25%未満を1、発病面積25%以上50%未満を2、発病面積50%以上75%未満を3、発病面積75%以上を4とする5段階で評価した。これから防除価を次式により算出した。
防除価=((無処理区の発病指数)-(各処理区の発病指数))
/(無処理区の発病指数) ×100
その結果を表19に示す。
Claims (9)
- 式(I):
[式(I)中、R1~R4はそれぞれ独立して、水素原子、-SO3H、-PO3H2、グリコシル基または-COR11を示す。R11は、無置換の若しくは置換基を有するC1~30アルキル基または無置換の若しくは置換基を有するC2~30アルケニル基を示す。]で表される化合物、
式(II):
[式(II)中、R5およびR6はそれぞれ独立して、水素原子、-SO3H、-PO3H2、グリコシル基または-COR11を示す。R11は、無置換の若しくは置換基を有するC1~30アルキル基または無置換の若しくは置換基を有するC2~30アルケニル基を示す。]で表される化合物およびそれらの塩からなる群から選ばれる少なくとも一つの物質(A)と、
植物の生理作用に影響を及ぼす物質(B)と
を含有する植物へのストレスを軽減する薬剤組成物。 - 物質(B)が、殺菌剤、殺虫剤、植物成長調整剤、および除草剤からなる群から選ばれる少なくとも一つである、請求項1に記載の組成物。
- 物質(B)が、呼吸阻害剤である、請求項1に記載の組成物。
- 物質(B)が、ストロビルリン系化合物である、請求項1に記載の組成物。
- 物質(A)が、式(I)[ただし、すべてのR1~R4が同時に水素原子であることはない。]で表される化合物またはその塩である、請求項1に記載の組成物。
- 物質(A)が、式(I)[ただし、R1~R4のうち少なくとも一つは-COR11を示し、R11は、無置換の若しくは置換基を有するC12~30アルキル基または無置換の若しくは置換基を有するC12~30アルケニル基を示す。]で表される化合物またはその塩である、請求項1に記載の組成物。
- 物質(A)が、式(I)[ただし、R1~R4はそれぞれ独立して、水素原子、または-COR11を示し、且つR1~R4のうち少なくとも一つは-COR11を示す。R11は、無置換の若しくは置換基を有するC1~30アルキル基または無置換の若しくは置換基を有するC2~30アルケニル基を示す。-COR11のうち少なくとも一つはその中のR11が、無置換の若しくは置換基を有するC12~30アルキル基または無置換の若しくは置換基を有するC12~30アルケニル基を示す。]で表される化合物またはその塩である、請求項1に記載の組成物。
- 請求項1~7のいずれか一つに記載の組成物を植物に施用することを含む、植物へのストレスを軽減する方法。
- 前記ストレスが、植物ウイルス、植物病原細菌、植物病原糸状菌、害虫若しくは雑草による生物的ストレス;または、高温、低温、高照度、低照度、過湿、乾燥、塩分、酸性、農薬、化学物質若しくは重金属による物理的若しくは化学的ストレスのいずれか少なくとも一つである、請求項8に記載の方法。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2524857A (en) * | 2013-11-01 | 2015-10-07 | Innospec Ltd | Detergent compositions |
WO2016063896A1 (ja) * | 2014-10-21 | 2016-04-28 | サントリーホールディングス株式会社 | アスコルビン酸誘導体及びこの誘導体を用いた配糖体の製造方法 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6729706B2 (ja) * | 2016-09-30 | 2020-07-22 | ダイキン工業株式会社 | 硫酸エステル又はその塩、及び、界面活性剤 |
CN106614676A (zh) * | 2016-12-30 | 2017-05-10 | 吴炜 | 一种含抗坏血酸和吡唑醚菌酯的农作物杀菌剂 |
CN106614644A (zh) * | 2017-01-09 | 2017-05-10 | 付明 | 一种含抗坏血酸和烯酰吗啉的霜霉病害防治用新药 |
JP6982485B2 (ja) * | 2017-12-13 | 2021-12-17 | 日本曹達株式会社 | 芝生用殺菌剤組成物 |
CN108969956B (zh) * | 2018-07-27 | 2020-12-29 | 华南农业大学 | 一种杀菌剂醚菌酯的降解菌株及其应用 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04342507A (ja) * | 1991-05-17 | 1992-11-30 | Meiji Seika Kaisha Ltd | 植物生長調節剤ならびに植物のストレス抵抗性を増強する方法 |
JP2001508808A (ja) | 1996-02-20 | 2001-07-03 | エイ. バダワイ、モハメッド | 抗菌性抗生物質の抗菌特性を高める方法 |
JP2001342102A (ja) | 2000-06-01 | 2001-12-11 | Nissan Chem Ind Ltd | 安定化される農薬組成物 |
JP2008538566A (ja) * | 2005-04-21 | 2008-10-30 | グレン エー. ゴールドスタイン, | 環境ストレスに対する植物の抵抗性および耐性を促進するためのn−アセチルシステインアミド(nacアミド) |
JP2010168298A (ja) | 2009-01-21 | 2010-08-05 | Nissan Chem Ind Ltd | 農薬活性成分の放出が制御される固型農薬製剤 |
WO2011030816A1 (ja) | 2009-09-14 | 2011-03-17 | 国立大学法人北海道大学 | 抗植物ウイルス剤 |
WO2011064312A1 (de) * | 2009-11-30 | 2011-06-03 | Basf Se | Pestizid-haltige mikrokapseln mit polyvinylmonomeren als vernetzer |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3225706C2 (de) * | 1982-07-09 | 1984-04-26 | A. Nattermann & Cie GmbH, 5000 Köln | Flüssige Wirkstofformulierungen in Form von Konzentraten für Mikroemulsionen |
JPH05170605A (ja) * | 1991-12-20 | 1993-07-09 | Iseki & Co Ltd | トマトの葉面散布剤 |
UA52701C2 (uk) * | 1996-10-11 | 2003-01-15 | Басф Акцієнгезельшафт | Твердий засіб захисту рослин та спосіб його одержання, спосіб боротьби з небажаним ростом рослин, спосіб боротьби з шкідливими грибами і тваринами-шкідниками та спосіб регулювання росту рослин |
JPH10298174A (ja) * | 1997-04-30 | 1998-11-10 | Showa Denko Kk | アスコルビン酸誘導体及びそれを含有するビタミンc剤 |
US6420419B1 (en) * | 1997-11-06 | 2002-07-16 | Showa Denko Kabushiki Kaisha | L-ascorbic acid 2-phosphate zinc salt and process for manufacturing the same |
DE60222935T2 (de) * | 2002-01-04 | 2008-07-24 | University Of Guelph, Guelph | Zubereitungen für die konservierung von früchten und gemüsen |
WO2004095926A2 (en) * | 2003-04-28 | 2004-11-11 | Monsanto Technology, Llc | Treatment of plants and plant propagation materials with an antioxidant to improve plant health and/or yield |
US7651977B2 (en) * | 2004-10-28 | 2010-01-26 | Valent U.S.A. Corporation | Herbicidal compositions |
JP2007023008A (ja) * | 2005-07-14 | 2007-02-01 | Shigeo Iida | 抗酸化剤含有組成物 |
TW200740369A (en) * | 2005-11-01 | 2007-11-01 | Dow Agrosciences Llc | Pesticidally active compositions having enhanced activity |
EA014777B1 (ru) * | 2006-03-10 | 2011-02-28 | Басф Се | Способ повышения устойчивости растений к пониженным температурам и/или заморозкам |
ES2315184B2 (es) * | 2007-07-20 | 2010-03-22 | Universidad Politecnica De Valencia | Una formulacion para la emision de sustancias bioactivas y su uso como agente de control de plagas de insectos. |
CN101766217A (zh) * | 2009-01-07 | 2010-07-07 | 蒋娟 | 柑橘保鲜剂 |
EP2225940B1 (en) | 2009-03-05 | 2014-03-12 | GAT Microencapsulation GmbH | Oil dispersions of nAChR binding neonicotinoids |
EP2747540B1 (en) * | 2011-08-25 | 2018-04-04 | Loveland Products, Inc. | Aqueous composition for accelerating secretion of alpha-amylase in plant seed germination |
CN102349513A (zh) * | 2011-10-31 | 2012-02-15 | 湖南中烟工业有限责任公司 | 一种含有烯虫酯的生物杀虫剂及其制备和应用方法 |
EP2793574A4 (en) | 2011-12-22 | 2015-09-02 | Vive Crop Prot Inc | STROBILURINFORMULIERUNGEN |
CN102584482A (zh) * | 2012-01-10 | 2012-07-18 | 天津滨农科技有限公司 | 一种无公害的白菜种子包衣剂 |
JP2014037407A (ja) * | 2012-07-20 | 2014-02-27 | Shizuoka Prefecture | ストレスに対する抵抗性を植物に付与する方法 |
-
2013
- 2013-07-19 US US14/415,292 patent/US9345243B2/en not_active Expired - Fee Related
- 2013-07-19 WO PCT/JP2013/004429 patent/WO2014013743A1/ja active Application Filing
- 2013-07-19 BR BR112015001013A patent/BR112015001013A2/pt not_active IP Right Cessation
- 2013-07-19 CA CA2879539A patent/CA2879539A1/en not_active Abandoned
- 2013-07-19 JP JP2013151150A patent/JP6212707B2/ja not_active Expired - Fee Related
- 2013-07-19 AU AU2013291439A patent/AU2013291439B2/en not_active Ceased
- 2013-07-19 EP EP13819577.1A patent/EP2875729A4/en not_active Withdrawn
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04342507A (ja) * | 1991-05-17 | 1992-11-30 | Meiji Seika Kaisha Ltd | 植物生長調節剤ならびに植物のストレス抵抗性を増強する方法 |
JP2001508808A (ja) | 1996-02-20 | 2001-07-03 | エイ. バダワイ、モハメッド | 抗菌性抗生物質の抗菌特性を高める方法 |
JP2001342102A (ja) | 2000-06-01 | 2001-12-11 | Nissan Chem Ind Ltd | 安定化される農薬組成物 |
JP2008538566A (ja) * | 2005-04-21 | 2008-10-30 | グレン エー. ゴールドスタイン, | 環境ストレスに対する植物の抵抗性および耐性を促進するためのn−アセチルシステインアミド(nacアミド) |
JP2010168298A (ja) | 2009-01-21 | 2010-08-05 | Nissan Chem Ind Ltd | 農薬活性成分の放出が制御される固型農薬製剤 |
WO2011030816A1 (ja) | 2009-09-14 | 2011-03-17 | 国立大学法人北海道大学 | 抗植物ウイルス剤 |
WO2011064312A1 (de) * | 2009-11-30 | 2011-06-03 | Basf Se | Pestizid-haltige mikrokapseln mit polyvinylmonomeren als vernetzer |
Non-Patent Citations (3)
Title |
---|
See also references of EP2875729A4 |
THE HORTICULTURE JOURNAL, vol. 6, no. 2, pages 169 - 175 |
VITAMINS, vol. 79, no. 2, 2005, pages 116 - 117 |
Cited By (6)
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GB2524857A (en) * | 2013-11-01 | 2015-10-07 | Innospec Ltd | Detergent compositions |
US20160264542A1 (en) * | 2013-11-01 | 2016-09-15 | Innospec Limited | Detergent compositions |
US9902707B2 (en) | 2013-11-01 | 2018-02-27 | Innospec Limited | Detergent compositions |
US9981933B2 (en) | 2013-11-01 | 2018-05-29 | Innospec Limited | Detergent compositions |
WO2016063896A1 (ja) * | 2014-10-21 | 2016-04-28 | サントリーホールディングス株式会社 | アスコルビン酸誘導体及びこの誘導体を用いた配糖体の製造方法 |
JPWO2016063896A1 (ja) * | 2014-10-21 | 2017-08-03 | サントリーホールディングス株式会社 | アスコルビン酸誘導体及びこの誘導体を用いた配糖体の製造方法 |
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AU2013291439A1 (en) | 2015-02-12 |
US9345243B2 (en) | 2016-05-24 |
US20150164072A1 (en) | 2015-06-18 |
JP6212707B2 (ja) | 2017-10-18 |
BR112015001013A2 (pt) | 2017-08-22 |
JP2014037406A (ja) | 2014-02-27 |
AU2013291439B2 (en) | 2015-08-06 |
CA2879539A1 (en) | 2014-01-23 |
EP2875729A4 (en) | 2016-03-09 |
EP2875729A1 (en) | 2015-05-27 |
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