WO2011071187A1 - Method for reducing temperature stress of plants - Google Patents

Method for reducing temperature stress of plants Download PDF

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Publication number
WO2011071187A1
WO2011071187A1 PCT/JP2010/072599 JP2010072599W WO2011071187A1 WO 2011071187 A1 WO2011071187 A1 WO 2011071187A1 JP 2010072599 W JP2010072599 W JP 2010072599W WO 2011071187 A1 WO2011071187 A1 WO 2011071187A1
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WO
WIPO (PCT)
Prior art keywords
group
plants
temperature stress
plant
compound
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PCT/JP2010/072599
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English (en)
French (fr)
Inventor
Asako Nagasawa
Fujio Mukumoto
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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
Priority to BR112012013973A priority Critical patent/BR112012013973A2/pt
Priority to CN2010800560978A priority patent/CN102651969A/zh
Priority to EP10836104.9A priority patent/EP2509420A4/en
Priority to NZ60019110A priority patent/NZ600191A/xx
Priority to MX2012006444A priority patent/MX2012006444A/es
Priority to CA 2781334 priority patent/CA2781334A1/en
Priority to US13/514,791 priority patent/US9084419B2/en
Priority to AU2010328956A priority patent/AU2010328956B2/en
Publication of WO2011071187A1 publication Critical patent/WO2011071187A1/en
Priority to ZA2012/03686A priority patent/ZA201203686B/en
Priority to IL219994A priority patent/IL219994A/en

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Classifications

    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01C—PLANTING; SOWING; FERTILISING
    • A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • 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
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Definitions

  • the present invention relates to a method for reducing temperature stress of plants.
  • temperature stress factor physiological functions of cells decline slowly or rapidly and thus various disorders may arise. While it has been known that phytohormones and some chemical substances such as plant growth regulators have an effect of reducing temperature stress of plants, these
  • An object of the present invention is to provide a method for reducing temperature stress of plants, and so on.
  • the present invention is based on the finding that plants that has been applied with a specified compound has a reduction in temperature stress even when the plants are exposed to a temperature stress factor.
  • the present invention includes the following constitutions .
  • a method for reducing temperature stress of plants which comprises applying an effective amount of one or more compounds selected from the group consisting of a compound represented by the formula (I) and an agriculturally
  • R 1 represents a phenyl group, a naphthyl group or an aromatic heterocyclic group, and these groups are optionally substituted with 1 to 5 members selected from among a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one o more halogen atoms, a C1-C6 alkylthio group optionally substituted with one or more halogen atoms, a C2-C6 alkenyl group optionally substituted with one or more halogen atoms, C2-C6 alkynyl group optionally substituted with one or more halogen atoms, an amino group, a C1-C6 alkylamino group and a di(Cl-C6 alkyl) amino group;
  • R 2 represents a hydroxyl group, an amino group, or a Cl- C6 alkoxy group
  • X represents a linear or branched C1-C6 alkylene group
  • Y represents a linear or branched C1-C6 alkylene group, or a linear or branched C1-C6 alkenylene group.
  • R 1 is a phenyl group, a 1-naphthyl group or a 3-indolyl group, wherein one or more hydrogen atoms in these groups are optionally replaced by 1 to 5 members selected from among a halogen atom, a hydroxyl group, a nitro group, a C1-C6 alkyl group and a C1-C6 alkoxy group;
  • R 2 is a hydroxyl group, an amino group or a C1-C6 alkoxy group
  • X is a linear or branched C1-C6 alkylene group
  • Y is a linear or branched C1-C6 alkylene group, or a linear or branched C1-C6 alkenylene group.
  • R 1 is a phenyl group, a 4-iodophenyl group, a 1-naphthyl group or a 3-indolyl group;
  • R 2 is a hydroxyl group or a methoxy group
  • X is an ethylene group or a tetramethylene group
  • Y is an ethylene group or a trimethylene group.
  • treatment is from 30g to 500 g per 100 kg of seeds.
  • temperature stress factor is an environmental factor which causes decline in a physiological function of plant cells as a result of exposure of a plant to a temperature environment that deviates from an optimal temperature
  • the temperature stress factor is referred to as a high
  • optimal temperature for growth or optimal temperature for germination of plants vary depending on plants and, generally, the optimal temperature for germination is often higher than the optimal temperature for growth.
  • the temperature stress of plants can be monitored by a comparison in a change in the following plant phenotypes between plants which are not exposed to a temperature stress factor and plants exposed to the temperature stress factor. That is, the plant phenotypes serve as indicators of the temperature stress of plants.
  • the temperature stress may be quantified by determining the "intensity of stress"
  • the method of the present invention is applied to plants that have been exposed to or to be exposed to a temperature stress factor whose "intensity of stress" represented by the above equation is from 105 to 200, preferably from 110 to 180, and more preferably from 120 to 160.
  • a temperature stress factor whose "intensity of stress" represented by the above equation is from 105 to 200, preferably from 110 to 180, and more preferably from 120 to 160.
  • the present invention is directed to a method for reducing an influence of a temperature stress factor on plants that have been exposed to or to be exposed to the temperature stress factor by applying the compound represented by the formula (I) to the plants.
  • the effect of reducing the temperature stress can be evaluated by a comparison of the indicator after the plants are exposed to the temperature stress factor between plants treated with the compound represented by the formula (I) and plants which are not treated.
  • Stages in which target plants in the present invention can be exposed to the temperature stress factor include all growth stages of plants, including a germination period, a vegetative growing period, a reproductive growing period and a harvesting period.
  • the application period of the present compound used in the present invention may be any growth stage of plants, and examples thereof include the germination period such as before seeding, at the time of seeding, and after seeding and before or after emergence; the vegetative growing period such as at the time of seedling raising, at the time of seedling transplantation, at the time of cuttage or sticking, or at the time of growing after settled planting; the
  • reproductive growing period such as before blooming, during blooming, after blooming, immediately before earing or during the earing period; and the harvesting period such as before harvesting plan, before ripening plan, or a coloration
  • Plants to which the present compound is to be applied may be plants that have been exposed to or to be exposed to the temperature stress factor. That is, the present compound can also be preventively applied to plants before being exposed to the temperature stress factor in addition to plants exposed to the temperature stress factor .
  • the present compound used in the method of the present invention is one or more compounds selected from the group consisting of a compound represented by the following formula (I) :
  • R 1 represents a phenyl group, a naphthyl group or an aromatic heterocyclic group, and these groups are optionally substituted with 1 to 5 members selected from among a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylthio group optionally
  • halogen atoms substituted with one or more halogen atoms, a C2-C6 alkenyl group optionally substituted with one or more halogen atoms, a C2-C6 alkynyl group optionally substituted with one or more halogen atoms, an amino group, a C1-C6 alkylamino group and a di(Cl-C6 alkyl) amino group;
  • R 2 represents a hydroxyl group, an amino group, or a Cl- C6 alkoxy group
  • X represents a linear or branched C1-C6 alkylene group
  • Y represents a linear or branched C1-C6 alkylene group, or a linear or branched C1-C6 alkenylene group
  • the compound represented by the formula (I) is a
  • the present compound is preferably one or more compounds selected from the group consisting of the compound of the formula (I), wherein in the formula (I),
  • R 1 is a phenyl group, a 1-naphthyl group or a 3-indolyl group, wherein one or more hydrogen atoms in these groups are optionally replaced by 1 to 5 members selected from among a halogen atom, a hydroxyl group, a nitro group, a C1-C6 alkyl group and a C1-C6 alkoxy group;
  • R 2 is a hydroxyl group, an amino group or a C1-C6 alkoxy group
  • X is a linear or branched C1-C6 alkylene group
  • Y is a linear or branched C1-C6 alkylene group, or a linear or branched C1-C6 alkenylene group
  • the present compound is more preferably one or more compounds selected from the group consisting of the compound of the formula (I), wherein in the formula (I),
  • R 1 is a phenyl group, a 4-iodophenyl group, a 1-naphthyl group or a 3-indolyl group;
  • R 2 is a hydroxyl group or a methoxy group
  • X is an ethylene group or a tetramethylene group
  • Y is an ethylene group or a trimethylene group
  • the compound represented by the formula (I) may be a salt with a base.
  • Examples of a basic salt of the compound represented by the formula (I) include the followings:
  • metal salts such as alkali metal salts and alkaline earth metal salts, including salts of sodium, potassium or magnesium;
  • alkylamine dihydroxy lower alkylamine and trihydroxy lower alkylamine .
  • the present compound used in the method of the present invention can be used alone, or used after being formulated using various inert ingredients as described hereinafter.
  • solid carrier used in formulation examples include fine powders or granules such as minerals such as kaolin clay, attapulgite clay, bentonite, montmorillonite, acid white clay, pyrophyllite, talc, diatomaceous earth and calcite; natural organic materials such as corn rachis powder and walnut husk powder; synthetic organic materials such as urea; salts such as calcium carbonate and ammonium sulfate; synthetic inorganic materials such as synthetic hydrated silicon oxide; and as a liquid carrier, aromatic hydrocarbons such as xylene, alkylbenzene and methylnaphthalene; alcohols such as 2-propanol, ethyleneglycol, propylene glycol, and ethylene glycol monoethyl ether; ketones such as acetone, cyclohexanone and isophorone; vegetable oil such as soybean oil and cotton seed oil; petroleum aliphatic hydrocarbons, esters, dimethylsulfoxide, acetonitrile and water.
  • surfactant examples include anionic surfactants such as alkyl sulfate ester salts, alkylaryl sulfonate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphate ester salts, lignosulfonate salts and naphthalene sulfonate formaldehyde polycondensates ; and nonionic surfactants such as alkyl sulfate ester salts, alkylaryl sulfonate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphate ester salts, lignosulfonate salts and naphthalene sulfonate formaldehyde polycondensates ; and nonionic surfactants such as alkyl sulfate ester salts, alkylaryl sulfonate salts, dialkyl sulfosuccinate salts, polyoxy
  • surfactants such as polyoxyethylene alkyl aryl ethers, polyoxyethylene alkylpolyoxypropylene block copolymers and sorbitan fatty acid esters and cationic surfactants such as alkyltrimethylammonium salts.
  • the other formulation auxiliary agents include water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone, polysaccharides such as Arabic gum, alginic acid and the salt thereof, CMC (carboxymethyl- cellulose) , Xanthan gum, inorganic materials such as aluminum magnesium silicate and alumina sol, preservatives, coloring agents and stabilization agents such as PAP (acid phosphate isopropyl) and BHT.
  • water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone
  • polysaccharides such as Arabic gum, alginic acid and the salt thereof
  • CMC carboxymethyl- cellulose
  • Xanthan gum inorganic materials
  • preservatives such as aluminum magnesium silicate and alumina sol
  • coloring agents and stabilization agents such as PAP (acid phosphate isopropyl) and BHT.
  • the method of the present invention is usually carried out by applying an effective amount of the present compound to plants or growing sites of plants.
  • the plant to which the present compound is to be applied include foliages, buds, flowers, fruits, ears or spikes, seeds, bulbs, stem tubers, roots and seedlings.
  • bulbs mean discoid stem, corm, rhizoma, root tuber and rhizophore.
  • the seedlings include cutting and sugar cane stem cutting.
  • growing sites of plants include soil before or after sowing plants.
  • Specific examples of the application method in the method of the present invention include treatment of foliages, floral organs or ears or spikes of plants, such as foliage spraying; treatment of cultivation lands of plants such as soil treatment; treatment of seeds such as seed sterilization, seed immersion or seed coating; treatment of seedlings; and treatment of bulbs such as seed tuber.
  • Specific examples of the treatment of foliages, floral organs or ears or spikes of plants in the method of the present invention include the treatment method of applying the compound to the surface of plants, such as foliage spraying or trunk spraying. Examples of the treatment also include a method of spraying the compound to the floral organ or entire plants in the blooming season including before blooming, during blooming and after blooming. Examples of the treatment in cereals and the like include a method of spraying the compound to the ear or spikes or entire plants in the earing season.
  • Examples of the soil treatment method in the method of the present invention include spraying onto the soil, soil incorporation, and perfusion of a chemical liquid into the soil (irrigation of chemical liquid, soil injection, and dripping of chemical liquid) .
  • Examples of the place to be treated include planting hole, furrow, around a planting hole, around a furrow, entire surface of cultivation lands, the parts between the soil and the plant, area between roots, area beneath the trunk, main furrow, growing soil, seedling raising box, seedling raising tray and seedbed.
  • Examples of the treating period include before seeding, at the time of
  • the present compound may be mixed in an irrigation liquid, and, examples thereof include injecting to irrigation facilities such as irrigation tube, irrigation pipe and sprinkler, mixing into the flooding liquid between furrows and mixing into a hydroponic medium.
  • an irrigation liquid may be mixed with the present compound in advance and, for example, used for
  • the present compound can be applied by winding a crop with a sheet or a string of a resin formulation, putting a string of the resin formulation around a crop so that the crop is surrounded by the string, and/or laying a sheet of the resin formulation on the soil surface near the root of a crop.
  • Examples of the method of treating seeds in the method of the present invention include a method for treating seeds or bulbs of a plant to be protected from temperature stress with the present compound and specific examples thereof include a spraying treatment in which a suspension of the present compound is atomized and sprayed on the seed surface or the bulb surface, a smearing treatment in which a wettable powder, an emulsion or a flowable agent of the present
  • seedlings in the method of the present invention include spraying treatment of spraying to the entire seedlings a dilution having a proper
  • concentration of active ingredients prepared by diluting the present compound with water immersing treatment of immersing seedlings in the dilution, and coating treatment of adhering the present compound formulated into a dust formulation to the entire seedlings.
  • the method of treating the soil before or after sowing seedlings include a method of spraying a dilution having a proper concentration of active ingredients prepared by diluting the present compound with water to seedlings or the soil around seedlings after sowing seedlings, and a method of spraying the present compound formulated into a solid formulation such as a granule to soil around seedlings after sowing seedlings.
  • the present compound may be mixed with a hydroponic medium in hydroponics, and may also be used as one of culture medium components in tissue culture.
  • hydroponics such as ENSHI
  • ENSHI a concentration within a range from 0.001 to 10,000 ppm.
  • the present compound can be dissolved or suspended in a conventionally used culture medium for plant tissue culture, such as an MS culture medium, at a concentration within a range from 0.001 to 10,000 ppm.
  • a conventionally used culture medium for plant tissue culture such as an MS culture medium
  • saccharides as a carbon source, various phytohormones and the like can be appropriately added.
  • the treatment amount can vary depending on the kind of plants to be treated,
  • the treatment amount is usually within a range from 0.1 to 1,000 g, and preferably from 1 to 500 g, in terms of an active ingredient amount, per 1, 000 m 2 .
  • An emulsion, a wettable powder, a flowable agent and a microcapsule are usually used for the treatment by spraying after dilution with water.
  • the concentration of the active ingredient is usually within a range from 0.01 to 10,000 ppm, and preferably from 1 to 5,000 ppm.
  • a dust formulation and a granule are usually used for the treatment as they are without dilution.
  • the weight of the present compound per seed is usually within a range from 0.0001 to 5 mg, and preferably from 0.005 to 1 mg, and the weight of the present compound per 100 kg of seeds is usually within a range from 5 to 1,000 g, and preferably from 30 to 500 g, and more preferably from 50 to 200 g.
  • the present compound can be used after being dissolved or suspended at a concentration of the active ingredient within a range from 0.01 to 10,000 ppm.
  • the weight of the present compound per seedling is usually within a range from 0.01 to 20 mg, and preferably from 0.1 to 10 mg.
  • the weight of the present compound per 1,000 m 2 is usually within a range from 0.1 to 100 g, and preferably from 1 to 50 g.
  • Examples of plants whose temperature stress can be reduced by the present invention include the followings.
  • crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, beet, canola, rapeseed, sunflower, sugar cane, tobacco, and pea, etc.;
  • solanaceous vegetables eggplant, tomato, pimento, pepper, potato, etc.
  • cucurbitaceous vegetables cucumber, pumpkin, zucchini, water melon, melon, squash, etc.
  • cruciferous vegetables Japanese radish, white turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli, cauliflower, etc.
  • asteraceous vegetables burdock, crown daisy, artichoke, lettuce, etc.
  • liliaceous vegetables green onion, onion, garlic, and asparagus
  • ammiaceous vegetables carrot, parsley, celery, parsnip, etc.
  • chenopodiaceous vegetables spikenach, Swiss chard, etc.
  • lamiaceous vegetables Pulnach, Swiss chard, etc.
  • strawberry Sweet potato, Dioscorea japonica, colocasia, etc.
  • flowers ;
  • fruits pomaceous fruits (apple, pear, Japanese pear, Chinese quince, quince, etc. ) , stone fleshy fruits (peach, plum, nectarine, Prunus mume, cherry fruit, apricot, prune, etc.), citrus fruits (Citrus unshiu, orange, lemon, rime, grapefruit, etc.), nuts (chestnuts, walnuts, hazelnuts, almond, pistachio, cashew nuts, macadamia nuts, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, kaki fruit, olive, Japanese plum, banana, coffee, date palm, coconuts, etc. ; and
  • Examples of plants whose temperature stress can be reduced by the present invention preferably include rice, corn, soybean, wheat and tomato.
  • plants include plants, to which resistance to HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr or thifensulfuron-methyl, EPSP synthetase inhibitors such as glyphosate, glutamine synthetase inhibitors such as the glufosinate, acetyl-CoA carboxylase inhibitors such as sethoxydim, and herbicides such as
  • bromoxynil, dicamba, 2,4-D, etc. has been conferred by a classical breeding method or genetic engineering technique.
  • Examples of a "plant” on which resistance has been conferred by a classical breeding method include rape, wheat, sunflower and rice resistant to imidazolinone ALS inhibitory herbicides such as imazethapyr, which are already commercially available under a product name of Clearfield (registered trademark) .
  • rape, wheat, sunflower and rice resistant to imidazolinone ALS inhibitory herbicides such as imazethapyr, which are already commercially available under a product name of Clearfield (registered trademark) .
  • Clearfield registered trademark
  • soybean on which resistance to sulfonylurea ALS inhibitory herbicides such as
  • thifensulfuron-methyl has been conferred by a classical breeding method, which is already commercially available under a product name of STS soybean.
  • examples on which resistance to acetyl-CoA carboxylase inhibitors such as trione oxime or aryloxy phenoxypropionic acid herbicides has been conferred by a classical breeding method include SR corn. The plant on which resistance to acetyl-CoA carboxylase inhibitors has been conferred is described in Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA) , vol. 87, pp. 7175-7179 (1990).
  • carboxylase inhibitors can be generated by introducing a gene of such an acetyl-CoA carboxylase variation into a plant by genetically engineering technology, or by introducing a variation conferring resistance into a plant acetyl-CoA carboxylase.
  • plants resistant to acetyl-CoA carboxylase inhibitors or ALS inhibitors or the like can be generated by introducing a site-directed amino acid substitution variation into an acetyl-CoA carboxylase gene or the ALS gene of the plant by introduction a nucleic acid into which has been introduced a base substitution variation represented Chimeraplasty Technique (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318) into a plant cell.
  • Examples of a plant on which resistance has been conferred by genetic engineering technology include corn, soybean, cotton, rape, sugar beet resistant to glyphosate, which is already commercially available under a product name of RoundupReady (registered trademark), AgrisureGT, etc.
  • plants include genetically
  • toxins expressed in such genetically engineered crops include: insecticidal proteins derived from Bacillus cereus or Bacillus popilliae; ⁇ -endotoxins such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C, derived from Bacillus thuringiensis; insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins derived from nematodes; toxins generated by animals, such as scorpion toxin, spider toxin, bee toxin, or insect- specific neurotoxins; mold fungi toxins; plant lectin;
  • protease inhibitors such as a trypsin inhibitor, a serine protease inhibitor, patatin, cystatin, or a papain inhibitor
  • ribosome-inactivating proteins RIP
  • RIP ribosome-inactivating proteins
  • steroid- metabolizing enzymes such as 3-hydroxysteroid oxidase
  • ecdysteroid-UDP-glucosyl transferase or cholesterol oxidase
  • an ecdysone inhibitor or HMG-COA reductase
  • ion channel ecdysteroid-UDP-glucosyl transferase, or cholesterol oxidase
  • an ecdysone inhibitor or HMG-COA reductase
  • inhibitors such as a sodium channel inhibitor or calcium channel inhibitor; juvenile hormone esterase; a diuretic hormone receptor; stilbene synthase; bibenzyl synthase;
  • chitinase chitinase
  • glucanase chitinase
  • Toxins expressed in such genetically engineered crops also include: hybrid toxins of ⁇ -endotoxin proteins such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl, Cry9C, Cry34Ab or Cry35Ab and insecticidal proteins such as VIPl, VIP2, VIP3 or VIP3A; partially deleted toxins; and modified toxins.
  • hybrid toxins are produced from a new
  • CrylAb comprising a deletion of a portion of an amino acid sequence
  • a modified toxin is produced by substitution of one or multiple amino acids of natural toxins.
  • Toxins contained in such genetically engineered plants are able to confer resistance particularly to insect pests belonging to Coleoptera, Hemiptera, Diptera, Lepidoptera and Nematodes, to the plants.
  • Genetically engineered plants which comprise one or multiple insecticidal pest-resistant genes and which express one or multiple toxins, have already been known, and some of such genetically engineered plants have already been on the market.
  • Examples of such genetically engineered plants include YieldGard (registered trademark) (a corn variety for expressing CrylAb toxin) , YieldGard Rootworm (registered trademark) (a corn variety for expressing Cry3Bbl toxin) , YieldGard Plus (registered trademark) (a corn variety for expressing CrylAb and Cry3Bbl toxins) , Herculex I (registered trademark) (a corn variety for expressing phosphinotricine N- acetyl transferase (PAT) so as to confer resistance to CrylFa2 toxin and glufosinate) , NuCOTN33B (registered trademark) (a cotton variety for expressing CrylAc toxin) , Bollgard I
  • NewLeaf (registered trademark) (a potato variety for
  • Agrisure (registered trademark) GT Advantage (GA21 glyphosate- resistant trait)
  • Agrisure (registered trademark) CB Advantage (Btll corn borer (CB) trait)
  • Protecta (registered trademark) .
  • plants also include crops produced using a genetic engineering technique, which have ability to generate antipathogenic substances having selective action.
  • PRPs antipathogenic substances
  • EP-A-0 392 225 antipathogenic substances
  • Such antipathogenic substances and genetically engineered crops that generate them are described in EP-A-0 392 225, WO
  • antipathogenic substances expressed in genetically engineered crops include: ion channel inhibitors such as a sodium channel inhibitor or a calcium channel inhibitor (KP1, KP4 and KP6 toxins, etc., which are produced by viruses, have been known) ; stilbene synthase; bibenzyl synthase; chitinase; glucanase; a PR protein; and
  • antipathogenic substances generated by microorganisms such as a peptide antibiotic, an antibiotic having a hetero ring, a protein factor associated with resistance to plant diseases (which is called a plant disease-resistant gene and is
  • the "plant” mentioned above includes plants on which advantageous characters such as characters improved in oil stuff ingredients or characters having reinforced amino acid content have been conferred by genetically engineering
  • VISTIVE registered trademark
  • low linolenic soybean having reduced linolenic content or high-lysine (high-oil) corn (corn with increased lysine or oil content) .
  • Stack varieties are also included in which a plurality of advantageous characters such as the classic herbicide characters mentioned above or herbicide tolerance genes, harmful insect resistance genes, antipathogenic substance producing genes, characters improved in oil stuff ingredients or characters having reinforced amino acid content are provided.
  • the conditions which lead to the high temperature stress may be conditions in which an average cultivation temperature in an environment where plants are cultivated is 25°C or higher, more severely 30°C or higher, and still more severely 35°C or higher.
  • the present invention is capable of providing a method for reducing temperature stress of plants under these high temperature stress conditions.
  • Reduction of the temperature stress of plants can be evaluated by measuring an improvement in the indicators which show the temperature stress.
  • physiological metabolism function in vivo declines and growth or germination is inhibited to cause a decrease in vitality of the plants, resulting in a state of being exposed to a low temperature stress factor.
  • the conditions which lead to the low temperature stress factor may be conditions in which an average
  • cultivation temperature in an environment where plants are cultivated is 15°C or lower, more severely 10°C or lower, and still more severely 5°C or lower.
  • the present invention is capable of providing a method for reducing temperature stress of plants under these low temperature stress conditions.
  • Reduction of the temperature stress of plants can be evaluated by measuring an improvement in the indicators which show the temperature stress.
  • plant phenotypes such as (1) germination percentage, (2) seedling establishment rate, (3) number of healthy leaves, (4) plant length, (5) plant weight, (6) leaf area, (7) leaf color, (8) number or weight of seeds or fruits, (9) quality of harvests, (10) flower setting rate or fruit setting rate and (11) chlorophyll fluorescence yield.
  • the indicators can be measured in the following manner. (1) Germination percentage
  • Seeds of plants are sown, for example, in the soil, on a filter paper, on an agar culture medium or on sand, and allowed to undergo germination, and then the ratio of the number of germinations to the number of seeds is examined.
  • Seeds of plants are sown, for example, in the soil, on a filter paper, on an agar culture medium or on sand, and then allowed to undergo cultivation for a given period of time. During the entire or partial cultivation period, temperature stress is applied, and the percentage of surviving seedlings is examined.
  • the number of healthy leaves is counted and the total number of healthy leaves is examined.
  • the ratio of the number of healthy leaves to the number of all leaves of plants is examined.
  • the length from the base of the stem of the above-ground part to the branches and leaves at the tip is measured.
  • the above-ground part of each of plants is cut and the weight is measured to determine a fresh weight of plants.
  • the cut sample is dried and the weight is measured to determine a dry weight of plants.
  • a photograph of plants is taken by a digital camera and the area of a green portion in the photograph is determined by image analysis software, for example, Win ROOF (manufactured by MITANI CORPORATION) to obtain a leaf area of plants.
  • image analysis software for example, Win ROOF (manufactured by MITANI CORPORATION) to obtain a leaf area of plants.
  • chlorophyll content is measured using a chlorophyll gauge (for example, SPAD-502, manufactured by KONICA MINOLTA Holdings, Inc.) to determine the leaf color.
  • a chlorophyll gauge for example, SPAD-502, manufactured by KONICA MINOLTA Holdings, Inc.
  • the quality of harvests is evaluated, for example, by measuring the sugar content of fully matured fruits using a saccharimeter .
  • the number of flower setting and the number of fruit setting are counted to determine the fruit setting rate % (number of fruit setting/number of flower setting ⁇ 100) .
  • the chlorophyll fluorescence (Fv/Fm) of plants is determined to obtain the chlorophyll fluorescence yield.
  • Ten (10) parts of the present compound, 35 parts of a mixture of white carbon and a polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1:1) and 55 parts of water are mixed, and the mixture is subjected to fine grinding according to a wet grinding method, so as to obtain a flowable formulation .
  • AI premix 50.5 parts of the present compound, 38.5 parts of NN kaolin clay (manufactured by Takehara Chemical Industrial), 10 parts of MorwetD425 and 1.5 parts of MorwerEF (manufactured by Akzo Nobel Corp.). This premix is ground with a jet mill so as to obtain a powder formulation .
  • An emulsion prepared as in Formulation example 1 is used for smear treatment in an amount of 500 ml per 100 kg of dried sorghum seeds using a rotary seed treatment machine (seed dresser, produced by Hans-Ulrich Hege GmbH) so as to obtain treated seeds.
  • Seed treatment example 2
  • a flowable formulation prepared as in Formulation example 2 is used for smear treatment in an amount of 50 ml per 10 kg of dried rape seeds using a rotary seed treatment machine (seed dresser, produced by Hans-Ulrich Hege GmbH) so as to obtain treated seeds.
  • a rotary seed treatment machine seed dresser, produced by Hans-Ulrich Hege GmbH
  • a flowable formulation prepared as in Formulation example 3 is used for smear treatment in an amount of 40 ml per 10 kg of dried corn seeds using a rotary seed treatment machine (seed dresser, produced by Hans-Ulrich Hege GmbH) so as to obtain treated seeds.
  • Seed treatment example 4
  • the mixture is used for smear treatment in an amount of 60 ml per 10 kg of dried cotton seeds using a rotary seed treatment machine (seed dresser, produced by Hans- Ulrich Hege GmbH) so as to obtain treated seeds.
  • a powder agent prepared as in Formulation example 5 is used for powder coating treatment in an amount of 50 g per 10 kg of dried corn seeds so as to obtain treated seeds.
  • Seed treatment example 6 is used for powder coating treatment in an amount of 50 g per 10 kg of dried corn seeds so as to obtain treated seeds.
  • a powder agent prepared as in Formulation example 7 is used for powder coating treatment in an amount of 40 g per 100 kg of dried rice seeds so as to obtain treated seeds.
  • a flowable formulation prepared as in Formulation example 2 is used for smear treatment in an amount of 50 ml per 10 kg of dried soybean seeds using a rotary seed treatment machine (seed dresser, produced by Hans-Ulrich Hege GmbH) so as to obtain treated seeds.
  • a rotary seed treatment machine seed dresser, produced by Hans-Ulrich Hege GmbH
  • a flowable formulation prepared as in Formulation example 3 is used for smear treatment in an amount of 50 ml per 10 kg of dried wheat seeds using a rotary seed treatment machine (seed dresser, produced by Hans-Ulrich Hege GmbH) so as to obtain treated seeds.
  • Seed treatment example 9 Seed treatment example 9
  • Seed treatment example 10 (manufactured by Sun Chemical) and 35 parts of water are mixed and the resultant mixture is used for smear treatment in an amount of 70 ml per 10 kg of potato tuber pieces using a rotary seed treatment machine (seed dresser, produced by Hans- Ulrich Hege GmbH) so as to obtain treated seeds. Seed treatment example 10
  • a powder agent prepared as in Formulation example 5 is used for powder coating treatment in an amount of 40 g per 10 kg of dried sugar beet seeds so as to obtain treated seeds .
  • Tomato seeds (cultivar: PATIO) were sown on a hydroponic sponge and then cultivated for 3 to 4 weeks under the
  • a DMSO solution having a concentration 10,000 times of each test concentration was prepared, and 10 pL of the obtained DMSO solution was added to 100 ml of distilled water to obtain a test liquid.
  • An aqueous solution having a concentration of 250,000 ppm of a sodium salt of the compound A was prepared and the obtained aqueous solution was added to 100 ml of distilled water so as to give each test
  • an aqueous solution as a test liquid was prepared by adding 10 L of DMSO to 100 ml of distilled water.
  • test group of the present invention the number of healthy leaves (2 cotyledons and 3 true leaves) of each test plant was counted and each test plants was assigned a score from 0 to 5 with a score of 0 representing complete death and with a score of 5 representing having healthy leaves equally to the case before the stress treatment.
  • test results of the group to which aqueous solutions of the respective compounds have been applied were compared with the test results of the group to which an aqueous solution containing only DMSO added therein (control) has been applied.
  • control aqueous solution containing only DMSO added therein
  • seed coating was carried out using the Blank slurry solution in place of the slurry solution to obtain seeds for non- treated group.
  • the coated seeds (5 seeds each) were sown in the growing soil (AISAI) in a plastic pot and then cultivated for 18 days under the conditions of a temperature of 20 to
  • Test compound chemical (mg/g relative to non- part (mg/3
  • a flowable formulation of the compound A was obtained by adding about 120 mg of a mixture of white carbon and a polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio of 1 : 1) and 300 ⁇ of water to 0.5 mg of the compound A, followed by fine grinding using a wet grinding method.
  • the obtained flowable formulation was diluted with 50 ml of water to obtain a spray liquid.
  • 0.2% RINO as a sticker to the spray liquid, a sufficient amount (45 ml per 6 pots) was sprayed using an automatic spraying machine.
  • a flowable formulation not containing the compound A was prepared and then sprayed to the non-treated group. Under the conditions of a temperature of 20 to 25°C, a humidity of 50 to 75%, an illuminance of 5,300 lx, and a day length of 16 hours, cultivation was carried out for 2 days.
  • test plants were cultivated for 4 days under the conditions of a temperature of 20 to 25°C, a humidity of 50 to 75%, an illuminance of 5,300 lx, and a day length of 16 hours, visual evaluation was carried out and a fresh weight of the above-ground part was examined.
  • a temperature of 20 to 25°C a humidity of 50 to 75%
  • an illuminance of 5,300 lx a day length of 16 hours
  • visual evaluation was carried out and a fresh weight of the above-ground part was examined.
  • test Example 4 Evaluation Test for Reduction of High
  • Tomato seeds (cultivar: Micro-Tom) were sown in the growing soil (AISAI) in a plastic pot and then cultivated in a greenhouse (set at a temperature of 25°C) for about 4 weeks.
  • a soil irrigation treatment was carried out twice, using an aqueous solution of a sodium salt of the compound A in an amount of 50 ml per seedling, on the 15th day and the 22nd day after seeding.
  • a soil irrigation treatment was carried out using distilled water in an amount of 50 ml per seedling to form a non-treated group.
  • plants cultivated up to the period when a 1st flower cluster blooms (1 to 2 flowers bloom(s), on the 32nd day after seeding) were cultivated for 7 days under the conditions of a temperature of 40°C (day) /30°C (night), a humidity of 63% (day) /70% (night), an illuminance of 7,100 lx, and a day length of 16 hours in the stress exposed group, while plants were cultivated for 7 days in a greenhouse (set at a temperature of 25°C) in the stress non- exposed group.
  • test plants were cultivated for 13 days in a greenhouse (set at a temperature of 25°C) , the number of flower setting and the number of fruit setting were counted to determine a fruit setting rate (%) (number of fruit setting/number of flower setting * 100) . While the fruit setting rate decreased due to high temperature stress exposure in the non-treated group, a decrease in fruit setting rate was remarkably alleviated in the group treated with the compound A as compared with the non-treated group.
  • Test Example 5 Evaluation Test for Reduction of High Temperature Stress by Tomato Spraying Treatment (Number or Weight of Seeds or Fruits, Fruit Setting Rate)
  • Tomato seeds (cultivar: Micro-Tom) are sown in the growing soil (AISAI) in a plastic pot and then cultivated for about 4 weeks in a greenhouse (set at a temperature of 25°C) up to the period when a 1st flower cluster blooms (one to two flowers bloom(s)).
  • the solution After adding 0.2% RINO as a sticker to an aqueous solution of any one of the compounds A to G, the solution is sprayed to the entire test plants in an amount of 10 ml per seedling .
  • the above compound solution is sprayed to foliages of the test plants in an amount of 10 ml per seedling. After the spraying treatment, the test plants are air-dried for about 2 hours .
  • a spraying treatment is carried out in the same manner, using distilled water containing only 0.2% RINO as a sticker added therein to form a non-treated group.
  • test plants having been subjected to the spraying treatment are cultivated for 7 days under the conditions of a temperature of 40°C (day) /30°C (night), a humidity of 63% (day) /70% (night), an illuminance of 7,100 lx, and a day length of 16 hours.
  • test plants are cultivated for about 2 weeks in a greenhouse (set at a temperature of 25°C) .
  • the number of flower setting and the number of fruit setting are counted to determine a fruit setting rate (%) (number of fruit setting/number of flower setting ⁇ 100) .
  • the diameters of fruits are measured and the average is
  • test plants having subjected to the spraying
  • test plants are cultivated in a greenhouse (set at a temperature of 25°C) until grain filling and the grain weight is examined.
  • a greenhouse set at a temperature of 25°C
  • an increase in the grain weight is observed.
  • a hydroponic sponge piece (1 cm ⁇ 1 cm ⁇ 0.2 cm) is immersed with an MS culture medium (containing 2.5 mM MES, 2% sucrose, and a 1,000 times diluted Gamborg vitamin solution G1019 (manufactured by Sigma-Aldrich Corporation) ) and 5 to 8 Arabidopsis (ecotype Columbia) seeds having been subjected to surface sterilization are sown on the sponge.
  • an MS culture medium containing 2.5 mM MES, 2% sucrose, and a 1,000 times diluted Gamborg vitamin solution G1019 (manufactured by Sigma-Aldrich Corporation)
  • 5 to 8 Arabidopsis (ecotype Columbia) seeds having been subjected to surface sterilization are sown on the sponge.
  • After the low temperature treatment at 4°C for 2 to 4 days), cultivation is carried out for 6 days under the conditions of a temperature of 23°C, a humidity of 45%, an illuminance of 3,500 lx, and a light period of 16 hours/a dark period
  • an MS culture medium which is a culture medium containing 2.5 mM MES, 2% sucrose and a 1,000 times diluted Gamborg vitamin solution G1019 (manufactured by Sigma-Aldrich Corporation) , containing any one of the compounds A to G having a
  • a DMSO solution having a concentration 1,000 times of each test concentration is prepared, and 0.5 ⁇ , of the obtained DMSO solution is added to 0.5 ml of the MS culture medium.
  • compound A is prepared and the obtained aqueous solution is added to 0.5 ml of the MS culture medium so as to give each test concentration, and then 0.5 i ⁇ L of DMSO is added to 0.5 ml of the culture medium.
  • an MS culture medium containing 0.1% DMSO added therein is prepared to form a non- treated group.
  • a lidded 24-well plate is sealed with a film, followed by immersion in a water incubator and further incubation at 45°C for 60 minutes.
  • a lidded 24-well plate is sealed with surgical tape, followed by cultivation for 6 days under the conditions of a temperature of 0 to 1°C, a humidity of 40 to 70%, an
  • test plants are cultivated for 3 to 5 days under the conditions of a temperature of 23°C, a humidity of 45%, an illuminance of 3,500 lx, and a light period of 16 hours/a dark period of 8 hours.
  • a photograph of each well is taken by a digital camera and the area of the green portion of the photograph is determined by imageing analysis software Win ROOF (manufactured by MITANI).
  • Corn seeds (cultivar: PIONEER 120 31P41) are sown in the growing soil (AISAI) in a plastic pot and then cultivated for 7 days under the conditions of a temperature of 20 to 25°C, a humidity of 50 to 75%, an illuminance of 4,500 lx, and a day length of 16 hours.
  • AISAI growing soil
  • a DMSO solution having a concentration 1,000 times of each test concentration of any one of the compounds A to G is prepared and then diluted with distilled water.
  • An aqueous solution (250,000 ppm) of a sodium salt of the compound A is diluted to prepare a test liquid.
  • the test plants are cultivated for 2 days under the conditions of a temperature of 20 to 25°C, a humidity of 50 to 75%, an illuminance of 4,500 lx, and a day length of 16 hours.
  • the soil perfusion treatment is carried out in the same manner to form a non-treated group.
  • the above test plants subjected to the soil perfusion are cultivated for 5 days under the conditions of a
  • the test plants are cultivated for 4 days under the conditions of a temperature of 20 to 25°C, a humidity of 50 to 75%, an illuminance of 4,500 lx, and a day length of 16 hours, and the plant weight and the length of true leaves are measured.
  • the chlorophyll fluorescence Fv/Fm
  • MAXI-IMAGING-PAM MAXI-IMAGING-PAM, ALZ
  • MAXI-IMAGING-PAM a pulse modulation chlorophyll fluorometer
  • Using a chlorophyll gauge (SPAD-502, manufactured by KONICA MINOLTA Holdings, Inc.), the chlorophyll content is measured.
  • each group treated with the present compound as compared with the non-treated group, the length of true leaves and the plant weight increase and growth acceleration of the above-ground part is observed.
  • an increase in the chlorophyll fluorescence and an increase in the chlorophyll content are observed as compared with the non- treated group.
  • distilled water containing 1,000 ppm of Benlate is washed with distilled water, incubated in distilled water for one day and then subjected to a forced germination treatment.
  • cotton wool is spread and then the seeds subjected to the forced germination treatment are sown.
  • a hydroponic culture medium (8-fold diluted Kimura B hydroponic culture solution) is added thereto, followed by cultivation for 3 to 10 days under the conditions of a
  • a DMSO solution having a concentration 1,000 times of each test concentration of any one of the compounds A to G is prepared and then diluted with a hydroponic culture medium.
  • An aqueous solution (250,000 ppm) of a sodium salt of the compound A is diluted with the hydroponic culture medium to prepare a liquid having a test concentration.
  • the above rice seedling is transferred to these hydroponic culture media containing the compound, and then cultivated for 7 to 10 days under the conditions of a temperature of 28°C (day)/23°C (night), a humidity of 60%, an illuminance of 7,100 lx, and a day length of 12 hours.
  • the above rice seedlings are cultivated to form a non-treated group.
  • the seedlings during the treatment with the present compound are cultivated for 3 to 7 days under the conditions of a temperature of 2 to 4°C, a humidity of 40 to 70%, an illuminance of 3,500 lx, and a day length of 12 hours in the stress exposed group, and under the conditions of a
  • seed coating was carried out using the Blank slurry solution in place of the slurry solution to obtain seeds for non-treated group.
  • the coated seeds (5 seeds each) were sown in the growing soil (AISAI) in a plastic pot and then cultivated in a greenhouse (set at a temperature of 18°C (day)/15°C (night)) for 17 days.
  • thinning was carried out to control the number of seedlings to 3 per pot.
  • the above test plants on the 17th day after seeding were cultivated for 19 days in an artificial climate chamber under the conditions of a temperature of 36°C (day) /32°C (night), a humidity of 50% (day) /60% (night), an illuminance of 7,000 lx, and a day length of 12 hours.

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BR112012013973A BR112012013973A2 (pt) 2009-12-11 2010-12-09 método para redução de estresse pela temperatura em plantas
CN2010800560978A CN102651969A (zh) 2009-12-11 2010-12-09 用于降低植物的温度胁迫的方法
EP10836104.9A EP2509420A4 (en) 2009-12-11 2010-12-09 METHOD FOR REDUCING THERMAL STRESS ON PLANTS
NZ60019110A NZ600191A (en) 2009-12-11 2010-12-09 Method for reducing temperature stress of plants
MX2012006444A MX2012006444A (es) 2009-12-11 2010-12-09 Metodo para reducir el estres por temperatura de plantas.
CA 2781334 CA2781334A1 (en) 2009-12-11 2010-12-09 Method for reducing temperature stress of plants
US13/514,791 US9084419B2 (en) 2009-12-11 2010-12-09 Method for reducing temperature stress of plants
AU2010328956A AU2010328956B2 (en) 2009-12-11 2010-12-09 Method for reducing temperature stress of plants
ZA2012/03686A ZA201203686B (en) 2009-12-11 2012-05-21 Method for reducing temperature stress of plants
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US9179672B2 (en) 2011-08-24 2015-11-10 Sumitomo Chemical Company, Limited Composition and method for controlling plant diseases
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WO2013027859A1 (en) * 2011-08-24 2013-02-28 Sumitomo Chemical Company, Limited Composition and method for controlling plant diseases
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KR20120115255A (ko) 2012-10-17
EP2509420A4 (en) 2013-08-28
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AU2010328956B2 (en) 2015-02-12
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CA2781334A1 (en) 2011-06-16

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