WO2015141867A1 - Plant disease control composition and method for controlling plant disease by application of same - Google Patents

Plant disease control composition and method for controlling plant disease by application of same Download PDF

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Publication number
WO2015141867A1
WO2015141867A1 PCT/JP2015/059278 JP2015059278W WO2015141867A1 WO 2015141867 A1 WO2015141867 A1 WO 2015141867A1 JP 2015059278 W JP2015059278 W JP 2015059278W WO 2015141867 A1 WO2015141867 A1 WO 2015141867A1
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WO
WIPO (PCT)
Prior art keywords
group
compound
compounds
atom
formula
Prior art date
Application number
PCT/JP2015/059278
Other languages
French (fr)
Inventor
Seiya Sakurai
Toshiaki Ohara
Munetsugu Morimoto
Nobuhiro Kondo
Hideaki Ikishima
Original Assignee
Mitsui Chemicals Agro, Inc.
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.)
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Publication date
Priority to KR1020167028181A priority Critical patent/KR102324523B1/en
Priority to US15/126,407 priority patent/US10201158B2/en
Priority to JP2016558150A priority patent/JP6514229B2/en
Priority to BR112016021563-0A priority patent/BR112016021563B1/en
Application filed by Mitsui Chemicals Agro, Inc. filed Critical Mitsui Chemicals Agro, Inc.
Priority to CN201580014920.1A priority patent/CN106132202B/en
Priority to UAA201610555A priority patent/UA121030C2/en
Priority to CR20160478A priority patent/CR20160478A/en
Priority to RU2016141053A priority patent/RU2673722C2/en
Priority to AU2015232357A priority patent/AU2015232357C1/en
Priority to MYPI2016703396A priority patent/MY189356A/en
Priority to MX2016012145A priority patent/MX2016012145A/en
Priority to CA2943184A priority patent/CA2943184C/en
Priority to EP15764226.5A priority patent/EP3119200A4/en
Publication of WO2015141867A1 publication Critical patent/WO2015141867A1/en
Priority to PH12016501829A priority patent/PH12016501829A1/en

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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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • 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
    • A01N37/20—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 group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
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    • A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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    • A01N37/50—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 the nitrogen atom being doubly bound to the carbon skeleton
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    • A01N43/28—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • 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
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    • A01N43/30—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • 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
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Definitions

  • the present invention relates to a plant disease control composition, which is characterized by comprising as active ingredients thereof at least one quinoline compound represented by general formula (I) indicated below in the present description or a salt thereof (group a), and one or more fungicidal compound selected from the group consisting of compounds (b-1) to (b-106) (group b), and to a method for controlling plant disease by applying that composition.
  • a plant disease control composition which is characterized by comprising as active ingredients thereof at least one quinoline compound represented by general formula (I) indicated below in the present description or a salt thereof (group a), and one or more fungicidal compound selected from the group consisting of compounds (b-1) to (b-106) (group b), and to a method for controlling plant disease by applying that composition.
  • a quinoline compound represented by general formula (I) is known to - -
  • Patent Documents 1 to 4 demonstrate control effects as a fungicide against rice blast ⁇ Pyricularia oryzae) and against gray mold (Botrytis cinerea) in tomatoes, cucumbers and green beans by treating plants by seed disinfection or foliage spraying and the like (Patent Documents 1 to 4), while the mixing of a quinoline compound represented by general formula (I) with a certain type of fungicide is disclosed in Patent Document 5.
  • Patent Document 1 International Publication No. WO 2005/070917
  • Patent Document 2 Japanese Unexamined Patent Publication No. 2007-1944
  • Patent Document 3 International Publication No. WO 2007/011022
  • Patent Document 4 Japanese Unexamined Patent Publication No.
  • Patent Document 5 Japanese Unexamined Patent Publication No. 2010-6746
  • An object of the present invention is to provide a novel plant disease control composition, and method for controlling plant disease by applying that composition, that exhibits a plurality of disease spectra against various types of plant pathogens, demonstrates high plant disease control effects against organisms resistant to existing chemical agents, demonstrates a high level of activity even if the amount of active ingredient administered in a pathogen-rich environment is reduced, and is observed to be free of the occurrence of phytotoxicity.
  • the present invention is a plant disease control composition
  • a plant disease control composition comprising as active ingredients thereof: (a) at least one quinoline compound represented by general formula (I) or a salt thereof (group a):
  • R 1 and R 2 may be the same or different and represent a methyl group, ethyl group, propyl group, trifluoromethyl group, trifluoroethyl group, phenyl group, fluorophenyl group or chlorophenyl group,
  • R 3 and R 4 may be the same or different and represent a hydrogen atom, fluorine atom or methyl group
  • X represents a fluorine atom, chlorine atom, bromine atom, methyl group, ethynyl group, furyl group, thienyl group, cyano group, methoxyethanimidoyl group, ethoxyethanimidoyl group or phenoxyethanimidoyl group and n is 0, 1 or 2, and
  • Y represents a fluorine atom or methyl group and m is 0 or 1 ;
  • one or more fungicidal compounds selected from:
  • Rb 7 represents a hydrogen atom, alkyl group, allyl group, benzyl group, cyano group or a valency that forms a double bond between a sulfur atom and a triazole ring to generate a ring represented by:
  • Rb 8 represents a hydrogen atom or fluorine atom
  • Rb 9 represents a hydrogen atom, alkyl group, allyl group, benzyl group or cyano group, and (b-38) compounds of general formula (VII)
  • Rb 10 represents a halogen atom and Rbn represents a nitrogen atom or methine group; amide compounds consisting of
  • organosulfur compounds consisting of
  • aminopyridine compounds consisting of
  • dithiine compounds consisting of
  • Rbi represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group
  • Rb 2 represents a fluorine atom or hydrogen atom
  • Rb 3 represents a halogen atom
  • Rb 4 represents a halogen atom, methoxy group or hydrogen atom
  • Z represents N or C-F
  • Rb 5 represents a methyl group or fluorine atom
  • Rb 6 represents -CH 2 OC(0)CH(CH 3 ) 2 , -C(0)CH 3 , -CH 2 OC(0)CH 3 , -C(0)
  • Rb 13 represents a chlorine atom or fluorine atom
  • Rb 14 represents a chlorine atom or hydrogen atom
  • Rb 15 represents a chlorine atom or bromine atom
  • Rb[ represents a fluorine atom or methyl group
  • Rbj 7 represents a hydrogen atom or fluorine atom
  • Ym represents a hydrogen atom when m is 0 and Xn represents a hydrogen atom when n is 0.
  • the plant disease control composition of the present invention has a plurality of disease spectra against various plant pathogens, including fungicide-resistant organisms (such as Pyricularia oryzae that causes rice blast or Botrytis cinerea that causes gray mold in tomatoes, cucumbers and green beans), and demonstrates superior - -
  • the plant disease control composition of the present invention exhibits a high level of plant disease control effects even against organisms resistant to existing chemical agents and is also observed to be free of the occurrence of phytotoxicity.
  • the quinoline compound represented by general formula (I) in the present invention can be in the form of a salt in the manner of a salt of an inorganic acid such as a hydrochloride, sulfate or nitrate, in the form of a phosphate, in the form of a sulfonate such as a methanesulfonate, ethanesulfonate, benzenesulfonate or p-toluenesulfonate, or in the form of a salt of an organic carboxylic acid such as an acetate, benzoate, oxalate, fumarate or salicylate (and preferably in the form of a hydrochloride, sulfate, nitrate, methanesulfonate, oxalate, fumarate or salicylate).
  • an inorganic acid such as a hydrochloride, sulfate or nitrate
  • a phosphate in the form of a
  • the quinoline compound represented by general formula (I) of the present invention and salts thereof can also be in the form of a solvate, and these solvates are also included in the present invention.
  • the solvate is preferably a hydrate.
  • Some quinoline compounds represented by general formula (I) in the present invention are compounds that have an asymmetric carbon, and in such cases, the invention of the present application also includes compounds having one type of optically active form as well as mixtures containing a plurality of optically active forms at an arbitrary ratio.
  • the quinoline compound represented by general formula (I) in the present invention is preferably:
  • the quinolone compound represented by general formula (I) is selected from the group consisting of:
  • Quinoline compounds represented by general formula (I) in the present invention are known compounds, and are produced according to, for example, the method described in International Publication No. WO 2005/070917, or methods complying therewith.
  • the fungicidal compound contained with at least one quinoline compound represented by general formula (I) or a salt thereof in the present invention (group a) is preferably selected from:
  • Rb 7 represents a hydrogen atom, alkyl group, allyl group, benzyl group, cyano group or a valency that forms a double bond between a sulfur atom and a triazole ring to generate a ring represented by:
  • Rb 8 represents a hydrogen atom or fluorine atom
  • Rb 10 represents a halogen atom and Rbn represents a nitrogen atom or methine group
  • organosulfur compounds consisting of
  • aminopyridine compound consisting of
  • Rb ⁇ represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group
  • Rb 2 represents a fluorine atom or hydrogen atom
  • Rb 3 represents a halogen atom
  • Rb 4 represents a halogen atom, methoxy group or hydrogen atom
  • Z represents N or C-F
  • Rb 13 represents a chlorine atom or fluorine atom
  • Rbn represents a chlorine atom or hydrogen atom
  • Rbis represents a chlorine atom or bromine atom
  • Rbn represents a hydrogen atom or fluorine atom
  • other fungicidal compounds (iii) consisting of:
  • Rb 7 represents a hydrogen atom, alkyl group, allyl group, benzyl group, cyano group or a valency that forms a double bond between a sulfur atom and a triazole ring to generate a ring represented by:
  • Rb 8 represents a hydrogen atom or fluorine atom
  • Rb 10 represents a halogen atom and Rbu represents a nitrogen atom or methine group
  • aminopyridine compound consisting of
  • Rbi represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group
  • Rb 2 represents a fluorine atom or hydrogen atom
  • Rb 3 represents a halogen atom
  • Rb 4 represents a halogen atom, methoxy group or hydrogen atom
  • Z represents N or C-F
  • Rbn represents a chlorine atom or fluorine atom
  • Rbi 4 represents a chlorine atom or hydrogen atom
  • Rb 15 represents a chlorine atom or bromine atom
  • Rbn represents a hydrogen atom or fluorine atom, and still more preferably selected from:
  • Rbj represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group
  • Rb 2 represents a fluorine atom or hydrogen atom
  • Rb 3 represents a halogen atom
  • Rb 4 represents a halogen atom, methoxy group or hydrogen atom
  • Rb 5 represents a methyl group or fluorine atom
  • Rb 6 represents -CH 2 OC(0)CH(CH 3 ) 2 , -C(0)CH 3 , -CH 2 OC(0)CH 3 , -C(0) or
  • Rb 7 represents a hydrogen atom, alkyl group, amino group or cyano group
  • Rb 8 represents a hydrogen atom or fluorine atom
  • the broken line indicates the presence or absence of a bond, represents a hydrogen atom, alkyl group, amino group or cyano group
  • Rb 10 represents a halogen atom and Rbn represents a nitrogen atom or methine group
  • Rbi represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group
  • Rb 2 represents a fluorine atom or hydrogen atom
  • Rb 3 represents a halogen atom
  • Rb 4 represents a halogen atom, methoxy group or hydrogen atom
  • Rb 7 represents a hydrogen atom, alkyl group, amino group or cyano group
  • Rb 8 represents a hydrogen atom or fluorine atom
  • Rb 9 represents a hydrogen atom, alkyl group, amino group or cyano group
  • Rb] 0 represents a halogen atom and Rbn represents a nitrogen atom or methine group
  • Rb 12 represents
  • Rb 10 represents a halogen atom and Rbn represents a nitrogen atom or methine group.
  • Rb 7 represents a valency that forms a double bond between a sulfur atom and a triazole ring to generate a moiety represented by:
  • Rb represents a fluorine atom, that is, a compound represented by formula:
  • Rbio is a chlorine atom
  • Rbn is a nitrogen atom
  • Rb 5 is a methyl group.
  • Rb 6 is -CH 2 OC(0)CH(CH 3 ) 2 .
  • Rb 16 is a fluorine atom.
  • Rb 17 represents a fluorine atom.
  • the fungicidal compounds used in combination with at least one quinoline compound represented by general formula (I) or a salt thereof is preferably selected from the group consisting of:
  • the compounds of group b are known compounds that are produced according to, for example, the methods described in International Publication No. WO
  • the plant disease control composition of the present invention allows the obtaining of synergistic controlling effects in comparison with the case of using each of the active ingredients alone.
  • the synergistic controlling effects and a degree thereof can be confirmed by using various test methods such as the method of Colby (see Colby SR, "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations ", Weed, 15, 1967, 20-22).
  • a plant disease control composition comprising a combination of effective ingredients that exhibit a difference between an actual value and a theoretical value, of 5% or more, more preferably 10% or more, and still more preferably 20% or more.
  • the plant disease control composition in the present invention may be used as is, it is normally used by mixing with a carrier, and is used by formulating into a wettable powder (WP), suspension concentrate (SC), granule (GR), dustable powder (DP), soluble concentrate (SC), water dispersible granule (WG), or emulsion concentrate (EC) and the like at a suitable time according to commonly known methods by adding a formulation additive such as a dispersing agent, wetting agent, binder, thickener, preservative, colorant or stabilizer and the like as necessary.
  • WP wettable powder
  • SC suspension concentrate
  • GR granule
  • DP dustable powder
  • SC soluble concentrate
  • WG water dispersible granule
  • EC emulsion concentrate
  • the content of the active ingredient in the form of the quinoline compound (I: group a compound) in these preparations is normally a weight ratio within the range of 0.005% to 99%, preferably within the range of 0.1%) to 90% and even more preferably within the range of 0.3% to 80%.
  • the content of the active ingredient in the form of the fungicidal compound of group b in these preparations is normally a weight ratio within the range of 0.005%) to 99%, preferably within the range of 0.1 % to 90% and even more preferably within the range of 0.3% to 80%.
  • the total of the quinoline compound (I: group a compound) and the fungicidal compound of group b is normally a weight ratio within the range of 0.01% to 99%, preferably within the range of 0.1% to 90% and even more preferably within the range of 0.3% to 80%.
  • the mixing ratio between the quinoline compound (I: group a compound) and the fungicidal compound of group b is normally a weight ratio of the fungicidal compound of group b to the quinoline compound 1 of 0.01 to 1000 and preferably a weight ratio of the fungicidal compound of group b to the quinoline compound 1 of 0.01 to 500, more preferably 1 of 0.01 to 100, still more preferably 1 of 0.01 to 50 and most preferably 1 of 0.01 to 25.
  • the combined content of active ingredients in the form of the quinoline compound (I: group a compound) and the fungicidal compound of group b is normally 0.01%) to 30% by weight in the case of a dustable powder, 0.1%) to 80%) by weight in the case of a wettable powder, 0.5% to 20%) by weight in the case of a granule, 2% to 50% by weight in the case of an emulsion concentrate, 1%) to 50% by weight in the case of a suspension concentrate, and 1% to 80% by weight in the case of a water dispersible granule.
  • the content of additives is 0% to 80%) by weight, and the content of the carrier is the amount obtained by subtracting the total content of active ingredient compounds and additives from 100% by weight.
  • the carrier used in the aforementioned composition refers to a synthetic or - -
  • natural, inorganic or organic substance that is incorporated to aid in the delivery of active ingredients to a site to be treated or to facilitate storage, transport or handling of active ingredient compounds can be used in the form of a solid or liquid provided it is used in ordinary agri-horticultural preparations, and there are no specific limitations thereon.
  • solid carriers include inorganic substances such as bentonite, montmorillonite, kaolinite, diatomaceous earth, kaolin, talc, clay, vermiculite, gypsum, calcium carbonate, amorphous silica or ammonium sulfate, plant-based organic substances such as soybean powder, wood meal, sawdust, wheat flour, lactose, sucrose or glucose, and urea.
  • liquid carriers examples include aromatic hydrocarbons and naphthenes such as toluene, xylene or cumene, paraffin-based hydrocarbons such as n-paraffin, iso-paraffin, liquid paraffin, kerosene, mineral oil or polybutene, ketones such as acetone or methyl ethyl ketone, ethers such as dioxane or diethylene glycol dimethyl ether, alcohols such as ethanol, propanol or ethylene glycol, carbonates such as ethylene carbonate, propylene carbonate or butylene carbonate, aprotic solvents such as dimethylformamide or dimethylsulfoxide, and water.
  • aromatic hydrocarbons and naphthenes such as toluene, xylene or cumene
  • paraffin-based hydrocarbons such as n-paraffin, iso-paraffin, liquid paraffin, kerosene, mineral oil or polybutene
  • ketones such as acetone or methyl ethyl
  • additives can be respectively used either alone or in combination corresponding to the purpose and in consideration of such factors as preparation form and treatment method in order to enhance the efficacy of compounds contained in the composition of the present invention.
  • additives in the form of surfactants normally used for the purpose of emulsifying, dispersing, spreading or wetting agricultural chemical preparations include nonionic surfactants such as sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene castor oil, polyoxyethylene alkyl ethers,
  • polyoxyethylene alkyl phenyl ethers polyoxyethylene dialkyl phenyl ethers, formalin condensates of polyoxyethylene alkyl phenyl ethers,
  • polyoxyethylene-polyoxypropylene block polymer ethers alkyl phenyl
  • polyoxyethylene-polyoxypropylene block polymer ethers polyoxyethylene alkyl amines, polyoxyethylene fatty acid amides, polyoxyethylene bisphenyl ethers, polyoxyalkylene benzyl phenyl ethers, polyoxyalkylene styryl phenyl ethers, polyoxyalkylene adducts of higher alcohols, polyoxyethylene ethers, ester-based silicone and fluorine-based surfactants; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene benzyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, polyoxyethylene-polyoxypropylene block polymer sulfates, paraffin sulfonates, alkane sulfonates, AOS, dialkyl sulf
  • polyoxyethylene benzylated phenyl phenyl ether phosphates polyoxyethylene styrylated phenyl ether phosphates, polyoxyethylene styrylated phenyl phenyl ether phosphates, polyoxyethylene-polyoxypropylene block polymer phosphates,
  • phosphatidylcholine phosphatidylcholine
  • phosphatidylethanolimine alkyl phosphates or sodium
  • tripolyphosphate polyanionic polymer surfactants derived from acrylic acid and acrylonitrile or acrylamidomethylpropane sulfonic acid; cationic surfactants such as alkyl trimethyl ammonium chlorides, methyl polyoxyethylene alkyl ammonium chlorides, alkyl-N-methyl pyridinium bromides, monomethylated ammonium chlorides, dialkyl methylated ammonium chlorides, alkyl pentamethyl propylene amine dichlorides, alkyl dimethyl benzalkonium chlorides or benzetonium chloride; and, amphoteric surfactants such as dialkyl diaminoethyl betaines or alkyl dimethyl benzyl betaines.
  • binders used as additives include sodium alginate, polyvinyl alcohol, gum arabic, CMC sodium and bentonite, examples of disintegrating agents include CMC sodium and croscarmellose sodium, and examples of stabilizers include hindered phenol-based antioxidants and benzotriazole-based or hindered amine-based ultraviolet absorbers.
  • pH adjusters include phosphoric acid, acetic acid and sodium hydroxide, and examples of antibacterial and antifungal agents include industrial disinfectants and antibacterial and antifungal agents such as
  • thickeners include xanthan gum, guar gum, CMC sodium, gum arabic, polyvinyl alcohol and montmorillonite.
  • antifoaming agents include silicone-based compounds, and examples of antifreezing agents include propylene glycol and ethylene glycol. However, the additives are not limited to those listed above.
  • composition of the present invention examples include treatment by spraying the foliage of plant individuals, seedling box treatment, soil surface spraying, soil surface spraying followed by soil incorporation, soil injection, soil injection followed by soil incorporation, soil irrigation, soil irrigation followed by soil incorporation, plant seed spraying, plant seed smearing, plant seed immersion and plant seed powder coating, any type of application method routinely used by persons with ordinary skill in the art demonstrates adequate efficacy.
  • the method for controlling plant disease in the present invention includes applying a plant disease control composition containing a compound of group a and a fungicidal compound of group b as active ingredients, simultaneously applying a plant disease control composition containing a compound of group a as an active ingredient and a plant disease control composition containing a fungicidal compound of group b as an active ingredient, or applying one of either a plant disease control composition containing a compound of group a as an active ingredient or a plant disease control composition containing a fungicidal compound of group b as an active ingredient followed by spraying the other composition, and the amount of time (time period) from applying one of either the plant disease control composition containing a compound of group a as an active ingredient or a plant disease control composition containing a fungicidal compound of group b as an active ingredient until spraying of the other composition is, for example, 1 minute to 2 weeks after applying either one of the compositions, preferably 5 minutes to 1 week after applying either one of the compositions, and
  • the plant disease control composition of the present invention can be prepared as a composition comprising high concentrations of the quinoline compound represented by general formula (I) and a fungicidal compound of group b.
  • This highly concentrated composition can be used as a spray by diluting with water.
  • the plant disease control composition of the present invention can also be prepared as a mixture by mixing a composition containing a high concentration of the quinoline compound represented by general formula (I) and a composition containing a high concentration of a fungicidal compound of group b at the time of use.
  • This highly concentrated composition can be used as a spray by diluting with water (tank-mixing).
  • the applied amount and applied concentration of the plant disease control composition containing a quinoline compound of group a and a fungicidal compound of group b as active ingredients thereof vary according to such factors as the target crop, target disease, degree of disease proliferation, compound drug form, application method and various environmental conditions
  • the applied amount is normally 10 g to 10,000 g per hectare and preferably 25 g to 5,000 g per hectare in terms of the amount of active ingredients.
  • the dilution factor thereof is normally 5 to 50,000, preferably 10 to 20,000 and more preferably 15 to 10,000.
  • the amount of the fungicide mixture used is normally 0.001 g to 50 g and preferably 0.01 g to 10 g per 1 kg of seeds.
  • spraying the composition of the present invention onto the foliage of plant individuals spraying onto the surface of soil, injecting into soil or irrigating soil drench, treatment may be carried out after diluting the chemical ingredient used to a suitable concentration in a suitable carrier.
  • the plant seeds may be immersed in the chemical ingredient as is.
  • plant seeds may be immersed, powder-coated, sprayed or smeared after diluting the chemical ingredient used to a suitable concentration in a suitable carrier.
  • the amount of preparation used in the case of powder-coating, spraying or smearing is normally about 0.05% to 50% and preferably 0.1% to 30% of the dry weight of the plant seeds, the amount used is not limited thereto and can be varied according to the form of the preparation and the type of plant seeds targeted for treatment.
  • suitable carriers include, but are not limited to, liquid carriers including water or organic solvents such as ethanol;, and solid carriers in the manner of inorganic substances such as bentonite, montmorillonite, kaolinite, diatomaceous earth, kaolin, talc, clay, vermiculite, gypsum, calcium carbonate, amorphous silica or ammonium sulfate, plant-based organic substances such as soybean powder, wood meal, sawdust, wheat flour, lactose, sucrose or glucose, and urea.
  • inorganic substances such as bentonite, montmorillonite, kaolinite, diatomaceous earth, kaolin, talc, clay, vermiculite, gypsum, calcium carbonate, amorphous silica or ammonium sulfate, plant-based organic substances such as soybean powder, wood meal, sawdust, wheat flour, lactose, sucrose or glucose, and urea.
  • Plant individuals as referred to in the present description refer to those that thrive without moving by carrying out photosynthesis, and specific examples thereof include, but are not limited to, rice, wheat, barley, corn, grapes, apples, pears, peaches, cherries, persimmons, citrus fruits, soybeans, green beans, strawberries, potatoes, cabbages, lettuces, tomatoes, cucumbers, eggplants, watermelons, beets, spinaches, peas, squashes, sugar canes, tobacco, green peppers, sweet potatoes, yams, konjac, rape, cotton, sunflowers, tulips, chrysanthemums and grasses.
  • Plant seeds as referred to in the present description refer to those used for agricultural propagation by storing nutrients for allowing the germination of seedlings, and specific examples thereof include, but are not limited to, corn, soybean, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, pea, squash, sugar cane, tobacco, green pepper and rape seeds, yam, potato, sweet potato and konjac seed tubers, edible lily and tulip bulbs, shallot seed bulbs, and seeds of plants created by genetic or other artificial manipulation, including soybeans, corn, rape seeds or cotton that do not inherently exist in nature and have been imparted with herbicide resistance, rice or tobacco suitable for cold climates, and seeds of transformants of corn, cotton or potatoes that have been imparted with the ability to produce insecticides.
  • composition of the present invention can naturally be used by mixing with other agricultural chemicals, soil conditioners or fertilizers such as insecticides, miticides, nematicides, fungicides, herbicides or plant growth regulators, and can be prepared by mixing therewith.
  • insecticides include, but are not limited to, pyrethroid-based compounds such as acrinathrin, allethrin [(lR)-isomer], bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,
  • pyrethroid-based compounds such as acrinathrin, allethrin [(lR)-isomer], bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,
  • beta-cypermethrin theta-cypermethrin, zeta-cypermethrin, cyphenothrin
  • vamidothion Bayer 22/190 (chlorothion), bromfenvinfos, bromophos,
  • fenothiocarb neonicotinoid-based compounds such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid or thiamethoxam,
  • diacylhydrazine-based compounds such as chromafenozide, halofenozide,
  • methoxyfenozide or tebufenozide benzoylurea-based compounds such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron, juvenile hormone-based compounds such as fenoxycarb, hydroprene, kinoprene, methoprene or pyriproxyfen, cyclodiene organochlorine-based compounds such as chlordane, endosulfan, lindane (gamma-HCH) or dienochlor, 2-dimethylaminopropane-l,3-dithiol-based compounds such as cartap hydrochloride or thiocyclam, amidine-based compounds such as amitraz, phenylpyrazole-based compounds such as ethiprole or fipronil
  • oxadiazine-based compounds such as indoxacarb, semicarbazone-based compounds such as metaflumizone, tetronic acid-based compounds such as spirodiclofen or spiromesifen, carbamoyl triazole-based compounds such as triazamate, tetrazine-based compounds such as diflovidazin, as well as abamectin, acequinocyl, azadirachtin, bensultap, benzoximate, bifenazate, buprofezin, CGA 50 439, chinomethionate, clofentezine, cryolite, cyromazine, dazomet, DCIP, DDT, diafenthiuron, D-D
  • flupyradifurone afidopyropen, fluhexafon and tralopyril.
  • composition and control method of the present invention are effective against, for example, the types of plant diseases indicated below.
  • the following indicates those specific diseases and pathogens thereof targeted for control by the present invention.
  • Examples thereof include, but are not limited to, blast ⁇ Pyricularia oryzae, ), sheath blight ⁇ Thanatephorus cucumeris, Rhizoctonia solani ), brown spot
  • Physalospora canker Physalospora piricola
  • canker Diaporthe medusaea
  • gray mold (Botrytis cinerea) of tomato, cucumber, pulse, strawberry, potato, cabbage, eggplant, lettuce, etc.
  • stem rot Sterotinia sclerotiorum of tomato, cucumber, bean, strawberry, potato, rape, cabbage, eggplant, lettuce, etc.
  • leaf spot (Alternaria brassicae) of rapeseed, alternaria leaf spot ⁇ Alternaria brassicae etc.), white spot (Cercosporella brassicae), blackleg (Leptosphaeria maculans), club root (Plasmodiophora brassicae) and downy mildew (Peronospora brassicae) of Brassica vegetables; foot rot (Rhizoctonia solani), yellows (Fusarium oxysporum) of cabbage; bottom rot (Rhizoctonia solani) and yellows (Verticillium dahliae) of Chinese cabbage; rust (Puccinia allii), alternaria leaf spot (Alternaria porri), southern blight (Sclerotium rolfsii.
  • More preferable targets for controlling plant diseases by the present invention are blast ⁇ Pyricularia oryzae, ), brown spot ⁇ Cochliobolus miyabeanus), "Bakanae” disease ⁇ Gibberella fujikuroi), seedling blight ⁇ Pythium spp., Fusarium spp.,
  • anthracnose (Glomerella cingulatd), young-fruit rot (Monilinia kusanoi) and brown rot ⁇ Monilinia fructicola) of cherry; anthracnose (Gloeosporium kaki), angular leaf spot ⁇ Cercospora kaki; Mycosphaerella nawae) and powdery mildew (Phyllactinia kakikora) of persimmon; melanose (Diaporthe citri), common green mold (Penicillium digitatum), blue mold (Penicillium italicum) and scab (Elsinoe fawcettii) of citrus;
  • gray mold (Botrytis cinerea) of tomato, cucumber, pulse, strawberry, potato, cabbage, eggplant, lettuce, etc.
  • stem rot Sterotinia sclerotiorum of tomato, cucumber, bean, strawberry, potato, rape, cabbage, eggplant, lettuce, etc.
  • powdery mildew (Sphaerotheca humuli) and anthracnose (Gromerella cingulatd) of strawberry; white scab (Elsinoe leucospila), anthracnose (Colletotrichum theaesinensis) and gray blight (Pestalotiopsis longiseta) of green tea; brown spot (Alternaria alternata (Tobacco pathotype)), powdery mildew (Erysiphe cichoracearum) and anthracnose (Colletotrichum tabacum) of tobacco; damping off (Fusarium oxysporum) of cotton; sclerotinia rot (Sclerotinia sclerotiorum) of sunflower; black spot (Diplocarpon rosae) and powdery mildew (Sphaerotheca pannosa) of rose; leaf blight (Septoria
  • fungicidal compound of formula (VII)- 1 of compound (b-38) used in the following preparation examples and test examples is a compound represented by the following formula.
  • Component 1 in the form of any of Compounds A, B and C (10, 1 or 0.01 parts), Component II (group b) in the form of any of the compounds described below (added amount indicated), Neogen powder (0.5 parts), Carplex (0.5 parts), Gohsenol (0.2 parts), Radiolite (0.8 parts) and H fine powder (used as the balance to bring to a total of 100 parts) were crushed and mixed to obtain wettable powder (al).
  • Component 1 in the form of any of Compounds A, B and C (10, 1 or 0.01 parts
  • Component II group b in the form of any of the compounds described below (added amount indicated)
  • Neogen powder 0.5 parts
  • Carplex 0.5 parts
  • Gohsenol 0.2 parts
  • Radiolite 0.8 parts
  • H fine powder used as the balance to bring to a total of 100 parts
  • the compounds (added amounts) used for Component II (group b) consisted of (b-1) (2 parts), (b-2) (2 parts), (b-3) (2 parts), (b-4)(2 to 10 parts), (b-5) (2 to 50 parts), (b-6) (0.4 to 50 parts), (b-7) (0.4 to 50 parts), (b-8)(0.4 to 2 parts), (b-9)(0.4 to 2 parts), (b-16)(2 parts), (b-19)(2 parts), (b-20) (0.4 to 10 parts), (b-21) (0.4 to 10 parts), (b-22) (0.4 to 10 parts), (b-23)(2 to 10 parts), (b-24) (0.4 to 10 parts), (b-25) (0.4 to 10 parts), (b-26) (0.4 to 10 parts), (b-27) (0.4 to 10 parts), (b-28) (0.4 to 10 parts), (b-29) (0.4 to 10 parts), (b-30) (0.4 to 10 parts), (b-31) (0.4 to 10 parts), (b-32) (0.4 to 10 parts), (
  • Component 1 in the form of any of Compounds A, B and C (10 or 1 parts), Component II (group b) in the form of any of the compounds described below (added amount indicated), propylene glycol (7 parts), sodium lignin sulfonate (4 parts), sodium dioctylsulfosuccinate (2 parts) and water (used as the balance to bring to a total of 100 parts) were wet-crushed with a sand grinder to obtain suspension concentrate (bl).
  • the compounds (added amounts) used for Component II (group b) consisted of (b-1) (2 parts), (b-2) (2 parts), (b-3) (2 parts), (b-4)(2 to 10 parts), (b-5) (2 to 50 parts), (b-6) (0.4 to 50 parts), (b-7) (0.4 to 50 parts), (b-8)(0.4 to 2 parts), (b-9)(0.4 to 2 parts), (b-16)(2 parts), (b-19)(2 parts), (b-20) (0.4 to 10 parts), (b-21) (0.4 to 10 parts), (b-22) (0.4 to 10 parts), (b-23)(2 to 10 parts), (b-24) (0.4 tolO parts), (b-25) (0.4 to 10 parts), (b-26) (0.4 to 10 parts), (b-27) (0.4 to 10 parts), (b-28) (0.4 to 10 parts), (b-29) (0.4 to - 7 -
  • Component 1 in the form of any of Compounds A, B and C (10 or 1 parts), Component II (group b) in the form of any of the compounds described below (added amount indicated), cyclohexane (10 parts), Tween20 (surfactant, 20 parts) and xylene (used as the balance to bring to a total of 100 parts) were uniformly dissolved and mixed to obtain emulsion concentrate (cl ).
  • the compounds (added amounts) used for Component II (group b) consisted of (b-1) (2 parts), (b-2) (2 parts), (b-3) (2 parts), (b-4)(2 to 10 parts), (b-5) (2 to 50 parts), (b-6) (0.4 to 50 parts), (b-7) (0.4 to 50 parts), (b-8)(0.4 to 2 parts), (b-9)(0.4 to 2 parts), (b-16)(2 parts), (b-19)(2 parts), (b-20) (0.4 to 10 parts), (b-21) (0.4 to 10 parts), (b-22) (0.4 to 10 parts), (b-23)(2 to 10 parts), (b-24) (0.4 to 10 parts), (b-25) (0.4 to 10 parts), (b-26) (0.4 to 10 parts), (b-27) (0.4 to 10 parts), (b-28) (0.4 to 10 parts), (b-29) (0.4 to 10 parts), (b-30) (0.4 to 10 parts), (b-31) (0.4 to 10 parts); (b-32) (0.4 to 10 parts),
  • Water-dispersible powder (a2) was obtained using the same method as
  • Suspension concentrate preparation (b2) was obtained using the same method as Preparation Example 2 with the exception of containing only one of either
  • Component I (group a) or Component II (group b).
  • Emulsion (c2) was obtained using the same method as Preparation Example 3 with the exception of containing only one of either Component I (group a) or
  • Water-dispersible powder (a3) was obtained using the same method as
  • Diclocymet (0.4 to 50 parts), Carpropamid (0.4 1 50 parts), Tolclofos-methyl (10 to 50 parts), and Oxolinic acid (50 parts).
  • Test Example 1 Tomato Gray Mold Preventive Test
  • Tomato plants (variety: Ohgata Fukuju) planted in plastic pots having a diameter of 5 cm were grown indoors to the second to third leaf stage.
  • Control value (1 - leaflet incidence rate of treated
  • X represents the theoretical value of the control value
  • P represents the control value in the case of spraying a certain chemical agent alone
  • Q represents the control value in the case of spraying the chemical agent used in combination alone.
  • the action resulting from combining two types of active ingredients is indicated to be more than additive, that is, to be synergistic.

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Abstract

Provided is a plant disease control composition that has a plurality of disease spectra against various plant pathogens and demonstrates superior control effects (synergistic control effects) that cannot be predicted from each component alone. The plant disease control composition comprises as active ingredients thereof at least one quinoline compounds represented by the following general formula: wherein, R1 and R2 represent, for example, optionally substituted alkyl groups or optionally substituted aryl groups, R3 and R4 represent, for example, hydrogen atoms, fluorine atom or methyl group, X represents, for example, a halogen atom or optionally substituted alkyl group, and Y represents a fluorine atom or methyl group, n is 0 to 2 and m is 0 or 1, or a salt thereof (group a), and one or more fungicidal compounds selected from group b.

Description

DESCRIPTION
PLANT DISEASE CONTROL COMPOSITION AND METHOD FOR CONTROLLING PLANT DISEASE BY APPLICATION OF SAME
TECHNICAL FIELD
[0001] The present invention relates to a plant disease control composition, which is characterized by comprising as active ingredients thereof at least one quinoline compound represented by general formula (I) indicated below in the present description or a salt thereof (group a), and one or more fungicidal compound selected from the group consisting of compounds (b-1) to (b-106) (group b), and to a method for controlling plant disease by applying that composition.
BACKGROUND ART
[0002] Numerous chemical agents have conventionally been used to control plant diseases. However, the frequent use and over-administration of chemical agents having a similar structure and similar mode of action to control the same types of plant diseases has resulted in the significant problem of plant pathogens becoming resistant to these chemical agents.
[0003] On the other hand, there is currently a growing demand among consumers for agricultural products that are grown using reduced levels of agricultural chemicals as well as a social demand for a reduction in the burden that agricultural chemicals place on the environment.
[0004] In addition, in the case of treating agricultural crops by mixing two or more types of chemical agents by tank mixing at farm fields where chemical agents are actually used, the combining of incompatible chemical agents may cause a mutual reduction in the effects of the chemical agents or result in a considerable risk of causing phytotoxicity.
[0005] In consideration of such circumstances, there is a desire for a plant disease control composition that is highly effective against organisms that are resistant to existing chemical agents and exhibits higher efficacy using a smaller amount of active ingredient. Moreover, there is also a desire for a highly compatible plant disease control composition and method for controlling plant disease composed of components (compounds) having different basic structures and different modes of action in order to prevent plant pathogens from acquiring resistance.
[0006] A quinoline compound represented by general formula (I) is known to - -
demonstrate control effects as a fungicide against rice blast {Pyricularia oryzae) and against gray mold (Botrytis cinerea) in tomatoes, cucumbers and green beans by treating plants by seed disinfection or foliage spraying and the like (Patent Documents 1 to 4), while the mixing of a quinoline compound represented by general formula (I) with a certain type of fungicide is disclosed in Patent Document 5.
PRIOR ART DOCUMENTS
Patent Documents
[0007] Patent Document 1 : International Publication No. WO 2005/070917
Patent Document 2: Japanese Unexamined Patent Publication No. 2007-1944
Patent Document 3: International Publication No. WO 2007/011022
Patent Document 4: Japanese Unexamined Patent Publication No.
2007-217353
Patent Document 5: Japanese Unexamined Patent Publication No. 2010-6746
DISCLOSURE OF THE INVENTION
Problems to be Solved by the Invention
[0008] As a result of examining combinations of quinoline compounds represented by general formula (I) and other fungicidal components, the inventors of the present invention found that, by combining a quinoline compound represented by general formula (I) with a specific fungicidal compound, superior control effects (synergistic effects) are obtained against various plant pathogens that could not have been predicted from the individual components alone, stable preventive effects are demonstrated against organisms resistant to existing chemical agents, and the occurrence of chemical damage is not observed, thereby leading to completion of the present invention.
[0009] An object of the present invention is to provide a novel plant disease control composition, and method for controlling plant disease by applying that composition, that exhibits a plurality of disease spectra against various types of plant pathogens, demonstrates high plant disease control effects against organisms resistant to existing chemical agents, demonstrates a high level of activity even if the amount of active ingredient administered in a pathogen-rich environment is reduced, and is observed to be free of the occurrence of phytotoxicity.
Means for Solving the Problems
[0010] The present invention is a plant disease control composition comprising as active ingredients thereof: (a) at least one quinoline compound represented by general formula (I) or a salt thereof (group a):
Figure imgf000005_0001
wherein,
R1 and R2 may be the same or different and represent a methyl group, ethyl group, propyl group, trifluoromethyl group, trifluoroethyl group, phenyl group, fluorophenyl group or chlorophenyl group,
R3 and R4 may be the same or different and represent a hydrogen atom, fluorine atom or methyl group,
X represents a fluorine atom, chlorine atom, bromine atom, methyl group, ethynyl group, furyl group, thienyl group, cyano group, methoxyethanimidoyl group, ethoxyethanimidoyl group or phenoxyethanimidoyl group and n is 0, 1 or 2, and
Y represents a fluorine atom or methyl group and m is 0 or 1 ; and
one or more fungicidal compounds selected from:
pyrazole carboxamides consisting of
(b-1) Fluxapyroxad,
(b-2) Benzovindiflupyr,
-3) a compound of formula (II)
Figure imgf000005_0002
(b-4) Bixafen,
(b-5) Penflufen,
(b-6) Sedaxane,
(b-7) Isopyrazam,
(b-8) a compound of formula (III)
Figure imgf000006_0001
-9) a compound of formula (IV)
Figure imgf000006_0002
methoxyacrylates consisting of
(b-10) Enoxastrobin,
(b-11) Pyraoxystrobin,
(b-12) Coumoxystrobin,
(b-13) Coumethoxystrobin,
(b-14) Flufenoxystrobin,
(b-15) Pyriminostrobin, and
(b-16) Picoxystrobin;
methoxycarbamates consisting of
(b-17) Pyrametostrobin,
(b-18) Triclopyricarb, and
(b-19) Pyraclostrobin;
azole compounds consisting of
(b-20) Imazalil,
(b-21) Prochloraz,
(b-22) Tetraconazole,
(b-23) Prothioconazole,
(b-24) Epoxiconazole,
(b-25) Ipconazole,
(b-26) Metconazole,
(b-27) Propiconazole,
(b-28) Cyproconazole,
(b-29) Difenoconazole,
(b-30) Fluquinconazole,
(b-31) Flusilazole, (b-32) Penconazole,
(b-33) Triadimenol,
(b-34) Flutriafol,
(b-35) Myclobutanil,
(b-36) compounds of general formula (V)
Figure imgf000007_0001
wherein Rb7 represents a hydrogen atom, alkyl group, allyl group, benzyl group, cyano group or a valency that forms a double bond between a sulfur atom and a triazole ring to generate a ring represented by:
Figure imgf000007_0002
and
Rb8 represents a hydrogen atom or fluorine atom,
(b-37) compounds of general formula (VI)
Figure imgf000007_0003
wherein the broken line indicates the presence or absence of a bond, and Rb9 represents a hydrogen atom, alkyl group, allyl group, benzyl group or cyano group, and (b-38) compounds of general formula (VII)
Figure imgf000007_0004
wherein Rb10 represents a halogen atom and Rbn represents a nitrogen atom or methine group; amide compounds consisting of
(b-39) Zoxamide,
(b-40) Fluopicolide,
(b-41) Carboxin,
(b-42) Thifluzamide,
(b-43) Fluopyram,
(b-44) Mandipropamid,
(b-45) Tiadinil,
(b-46) Isotianil,
(b-47) Isofetamid,
(b-48) Valifenalate,
-49) Pyraziflumid,
Figure imgf000008_0001
(b-50) Iprovalicarb;
strobilurin compounds consisting of
(b-51) Fluoxastrobin,
(b-52) Dimoxystrobin,
(b-53) Orysastrobin,
(b-54) Metominostrobin,
(b-55) Trifloxystrobin,
(b-56) Mandestrobin, and
(b-57) Fenaminostrobin;
benzimidazole compounds consisting of
(b-58) Benomyl,
(b-59) Carbendazim, and
(b-60) Thiabendazole;
pyrimidine compounds consisting of
(b-61) Cyprodinil, and
(b-62) Pyrimethanil;
quinolone compounds consisting of
(b-63) Quinoxyfen, and (b-64) Tebufloquin;
morpholine compounds consisting of
(b-65) FenpΓopimo h, and
(b-66) Tridemorph;
organosulfur compounds consisting of
(b-67) Metiram,
(b-68)Thiuram,
(b-69) Propineb,
(b-70) Folpet,
(b-71) Isoprothiolane,
(b-72) Acibenzolar-S-methyl,
(b-73) Probenazole, and
(b-74) Chinomethionat;
anilide compounds consisting of
(b-75) Benalaxyl-M,
(b-76) Pencycuron, and
(b-77) Flutianil;
aminopyridine compounds consisting of
(b-78) Picarbutrazox, and
(b-79) compounds of general formula (VIII)
Figure imgf000009_0001
(VIII) wherein Rbi2 represents
Figure imgf000009_0002
dithiine compounds consisting of
(b-80)
Figure imgf000009_0003
(IX) (X) and (b-81) Dithianon;
phenylketone compounds consisting of
(b-82) Metrafenone, and
(b-83) Pyriofenone;
other fungicidal compounds (i) consisting of
(b-84) Oxathiapiprolin,
(b-85) compounds of general formula (XI)
Figure imgf000010_0001
wherein Rbi represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group, Rb2 represents a fluorine atom or hydrogen atom, Rb3 represents a halogen atom, Rb4 represents a halogen atom, methoxy group or hydrogen atom and Z represents N or C-F,
(b-86) compounds of general formula (XII)
Figure imgf000010_0002
wherein Rb5 represents a methyl group or fluorine atom,
(b-87) compounds of general formula (XIII)
Figure imgf000010_0003
(XIII)
wherein Rb6 represents -CH2OC(0)CH(CH3)2, -C(0)CH3, -CH2OC(0)CH3, -C(0)
Figure imgf000010_0004
(b-88) a compound of formula (XIV)
Figure imgf000011_0001
b-89) compounds of general formula (XV)
Figure imgf000011_0002
wherein Rb13 represents a chlorine atom or fluorine atom, Rb14 represents a chlorine atom or hydrogen atom and Rb15 represents a chlorine atom or bromine atom, (b-90) compounds of general formula (XVI)
Figure imgf000011_0003
wherein Rb[ represents a fluorine atom or methyl group; other fungicidal compounds (ii) consisting of
(b-91) a compound of formula (XVII)
Figure imgf000011_0004
(b-92) a compound of formula (XVIII)
Figure imgf000012_0001
(XVIII),
(b-93) D-tagatose,
(b-94) compounds of general formula (XIX)
Figure imgf000012_0002
(XIX)
wherein Rbj7 represents a hydrogen atom or fluorine atom;
other fungicidal compounds (iii) consisting of
(b-95) Ametoctradin,
(b-96) Sulfur;
(b-97) Amisulbrom,
(b-98) Pyribencarb,
(b-99) Fenpyrazamine,
(b-100) Proquinazid,
(b-101) Spiroxamine,
(b-102) Fenpropidin,
(b-103) Pyrisoxazole,
(b-104) Pyroquilon,
(b-105) Phosphorous acid, and
(b-106) Hydroxyisoxazole (Hymexazol).
Furthermore, in the quinoline compounds represented by general formula (I), Ym represents a hydrogen atom when m is 0 and Xn represents a hydrogen atom when n is 0.
EFFECTS OF THE INVENTION
[0011] The plant disease control composition of the present invention has a plurality of disease spectra against various plant pathogens, including fungicide-resistant organisms (such as Pyricularia oryzae that causes rice blast or Botrytis cinerea that causes gray mold in tomatoes, cucumbers and green beans), and demonstrates superior - -
control effects (synergistic control effects) that could not have been predicted from the individual components alone. In addition, the plant disease control composition of the present invention exhibits a high level of plant disease control effects even against organisms resistant to existing chemical agents and is also observed to be free of the occurrence of phytotoxicity.
BEST MODE FOR CARRYING OUT THE INVENTION
[0012] Each of the terms used for the quinoline compounds represented by general formula (I) in the scope of claim for patent and description of the present application are in accordance with definitions commonly used in the field of chemistry as well as the definitions described in International Publication No. WO 2005/070917, Japanese Unexamined Patent Publication No. 2007-1944, International Publication No. WO 2007/011022 and Japanese Unexamined Patent Publication No. 2007-217353.
[0013] The quinoline compound represented by general formula (I) in the present invention can be in the form of a salt in the manner of a salt of an inorganic acid such as a hydrochloride, sulfate or nitrate, in the form of a phosphate, in the form of a sulfonate such as a methanesulfonate, ethanesulfonate, benzenesulfonate or p-toluenesulfonate, or in the form of a salt of an organic carboxylic acid such as an acetate, benzoate, oxalate, fumarate or salicylate (and preferably in the form of a hydrochloride, sulfate, nitrate, methanesulfonate, oxalate, fumarate or salicylate).
[0014] The quinoline compound represented by general formula (I) of the present invention and salts thereof can also be in the form of a solvate, and these solvates are also included in the present invention. The solvate is preferably a hydrate.
[0015] Some quinoline compounds represented by general formula (I) in the present invention are compounds that have an asymmetric carbon, and in such cases, the invention of the present application also includes compounds having one type of optically active form as well as mixtures containing a plurality of optically active forms at an arbitrary ratio.
[0016] The quinoline compound represented by general formula (I) in the present invention is preferably:
(a- 1 ) 3 -(5-fluoro-3 ,3 -dimethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline,
(a-2) 3 -(5-chloro-3 ,3 -dimethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline, (a-3) 3 -(5 -bromo-3 ,3 -dimethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline, (a-4) 3-(5-ethynyl-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, (a-5) 3 -(5 ,6-difluoro-3 ,3 -dimethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline
(a-6) 3-(3-ethyl-5-fluoro-3-propyl-3,4-dihydroisoquinolin-l-yl)quirioline - -
(a- 7) 3 -(5 -fluoro-3 -methyl-3 -propyl- 3 ,4-dihydroisoquinolin- 1 -yl)quinoline (a-8) 3 -(3 -methyl-3 -trifluoromethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline (a- 9) 3 - [3 -methyl-3 -(2,2,2-trifluoroethyl)-3 ,4-dihydroisoquinolin- 1 -yl] quinoline
(a- 10) 3 - [3 -methyl-3 -phenyl-3 ,4-dihydroisoquinolin- 1 -yl] quinoline
(a-1 1) 3-[3-methyl-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-l-yl]quinoline (a- 12) 3 -[3 -methyl-3 -(4-chlorophenyl)-3,4-dihydroisoquinolin-l-yl] quinoline (a-13) 3-(3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-l-yl)quinoline
(a- 14) 3 -(5-fluoro-3 ,3 ,4,4-tetramethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline (a- 15) 3 -(5-fluoro-3 ,3 ,4,4-tetramethyl-3 ,4-dihydroisoquinolin- 1 -yl)-6- fluoroquinoline
(a-16) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-l-yl)-8- fluoroquinoline
(a- 17) 3 -(5 -fluoro-3 ,3 ,4,4-tetramethyl-3 ,4-dihydroisoquinolin- 1 -yl)-8- methylquinoline
(a- 18) 3 -(4,4-difluoro-3 ,3 -dimethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline (a-19) 3-(4,5-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, (a-20) 3 -(4,4,5-trifluoro-3 ,3-dimethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline, or
a salt thereof.
[0017] In more preferable embodiment of the present invention, the quinolone compound represented by general formula (I) is selected from the group consisting of:
(a- 14) 3 -(5-fluoro-3 ,3 ,4,4-tetramethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline (a- 18) 3 -(4,4-difluoro-3 ,3-dimethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinolone, (a-20) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, and a salt thereof.
[0018] Quinoline compounds represented by general formula (I) in the present invention (group a compounds) are known compounds, and are produced according to, for example, the method described in International Publication No. WO 2005/070917, or methods complying therewith.
[0019] The fungicidal compound contained with at least one quinoline compound represented by general formula (I) or a salt thereof in the present invention (group a) is preferably selected from:
pyrazole carboxamides consisting of
(b-1) Fluxapyroxad,
(b-2) Benzovindiflupyr, ,„ b-3) a compound of formula (II)
Figure imgf000015_0001
(b-4) Bixafen,
(b-5) Penflufen,
(b-6) Sedaxane,
(b-7) Isopyrazam,
-8) a compound of formula (III)
Figure imgf000015_0002
-9) a compound of formula (IV)
Figure imgf000015_0003
methoxyacrylates consisting of
(b-16) Picoxystrobin;
methoxycarbamates consisting of
(b-19) Pyraclostrobin;
azole compounds consisting of
(b-20) Imazalil,
(b-21) Prochloraz,
(b-22) Tetraconazole,
(b-23) Prothioconazole,
(b-24) Epoxiconazole,
(b-25) Ipconazole,
(b-26) Metconazole,
(b-27) Propiconazole,
(b-28) Cyproconazole, (b-29) Difenoconazole,
(b-30) Fluquinconazole,
(b-31) Flusilazole,
(b-32) Penconazole,
(b-33) Triadimenol,
(b-34) Flutriafol,
(b-35) Myclobutanil,
b-36) compounds of general formula (V)
Figure imgf000016_0001
wherein Rb7 represents a hydrogen atom, alkyl group, allyl group, benzyl group, cyano group or a valency that forms a double bond between a sulfur atom and a triazole ring to generate a ring represented by:
Figure imgf000016_0002
Rb8 represents a hydrogen atom or fluorine atom, and
b-38) compounds of general formula (VII)
Figure imgf000016_0003
wherein Rb10 represents a halogen atom and Rbn represents a nitrogen atom or methine group;
amide compounds consisting of
(b-39) Zoxamide,
(b-40) Fluopicolide,
(b-41) Carboxin,
(b-42) Thifluzamide,
(b-43) Fluopyram,
(b-44) Mandipropamid, (b-45) Tiadinil,
(b-46) Isotianil,
(b-47) Isofetamid,
(b-49) Pyraziflumid,
Figure imgf000017_0001
; and
(b-50) Iprovalicarb;
strobilurin compounds consisting of
(b-51) Fluoxastrobin,
(b-52) Dimoxystrobin,
(b-53) Orysastrobin,
(b-54) Metominostrobin, and
(b-55) Trifloxystrobin ;
benzimidazole compounds consisting of
(b-58) Benomyl,
(b-59) Carbendazim, and
(b-60) Thiabendazole;
pyrimidine compounds consisting of
(b-61) Cyprodinil, and
(b-62) Pyrimethanil;
quinolone compounds consisting of
(b-63) Quinoxyfen, and
(b-64) Tebufloquin;
morpholine compounds consisting of
(b-65) Fenpropimorph, and
(b-66) Tridemo h;
organosulfur compounds consisting of
(b-67) Metiram,
(b-68) Thiuram,
(b-69) Propineb,
(b-70) Folpet,
(b-71) Isoprothiolane, - -
(b-72) Acibenzolar-S-methyl,
(b-73) Probenazole, and
(b-74) Chinomethionat;
anilide compounds consisting of
(b-75) Benalaxyl-M,
(b-76) Pencycuron, and
(b-77) Flutianil;
an aminopyridine compound consisting of
(b-78) Picarbutrazox;
a dithiine compound consisting of
(b-81) Dithianon;
phenylketone compounds consisting of
(b-82) Metrafenone, and
(b-83) Pyriofenone;
other fungicidal compounds (i) consisting of
(b-84) Oxathiapiprolin
(b-85) compounds of general formula (XI)
Figure imgf000018_0001
wherein Rb\ represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group, Rb2 represents a fluorine atom or hydrogen atom, Rb3 represents a halogen atom, Rb4 represents a halogen atom, methoxy group or hydrogen atom and Z represents N or C-F,
b-88) a compound of formula (XIV)
Figure imgf000018_0002
(b-89) compounds of general formula (XV)
Figure imgf000019_0001
wherein Rb13 represents a chlorine atom or fluorine atom, Rbn represents a chlorine atom or hydrogen atom and Rbis represents a chlorine atom or bromine atom, other fungicidal compounds (ii) consisting of:
b-91) a compound of formula (XVII)
Figure imgf000019_0002
(b-93) D-tagatose, and
(b-94) compounds of general formula (XIX)
Figure imgf000019_0003
(XIX)
wherein Rbn represents a hydrogen atom or fluorine atom; other fungicidal compounds (iii) consisting of:
(b-95) Ametoctradin,
(b-96) Sulfur;
(b-97) Amisulbrom, (b-98) Pyribencarb,
(b-99) Fenpyrazamine,
(b-100) Proquinazid,
(b-101) Spiroxamine,
(b-102) Fenpropidin,
(b-103) Pyrisoxazole,
(b-104) Pyroquilon,
(b-105) Phosphorous acid, and
(b-106) Hydroxyisoxazole (Hymexazol), and more preferably selected from:
pyrazole carboxamides consisting of
(b-1) Fluxapyroxad,
(b-2) Benzovindiflupyr,
-3) a compound of formula (II)
Figure imgf000020_0001
b-8) a compound of formula (III)
Figure imgf000020_0002
azole compounds consisting of
(b-36) compounds of general formula (V)
Figure imgf000021_0001
wherein Rb7 represents a hydrogen atom, alkyl group, allyl group, benzyl group, cyano group or a valency that forms a double bond between a sulfur atom and a triazole ring to generate a ring represented by:
Figure imgf000021_0002
Rb8 represents a hydrogen atom or fluorine atom, and
b-38) compounds of general formula (VII)
Figure imgf000021_0003
wherein Rb10 represents a halogen atom and Rbu represents a nitrogen atom or methine group;
amide compounds consisting of
(b-47) Isofetamid, and
(b-49) Pyraziflumid,
Figure imgf000021_0004
an aminopyridine compound consisting of
(b-78) Picarbutrazox;
other fungicidal compounds (i) consisting of
(b-84) Oxathiapiprolin
(b-85) compounds of general formula (XI)
Figure imgf000022_0001
wherein Rbi represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group, Rb2 represents a fluorine atom or hydrogen atom, Rb3 represents a halogen atom, Rb4 represents a halogen atom, methoxy group or hydrogen atom and Z represents N or C-F,
(b-88) a compound of formula (XIV)
Figure imgf000022_0002
b-89) compounds of general formula (XV)
Figure imgf000022_0003
wherein Rbn represents a chlorine atom or fluorine atom,
Rbi4 represents a chlorine atom or hydrogen atom and
Rb15 represents a chlorine atom or bromine atom;
other fungicidal compounds (ii) consisting of
(b-91) a compound of formula (XVII)
Figure imgf000022_0004
(b-92) a compound of formula (XVIII) (XVIII),
(b-93) D-tagatose,
(b-94) compounds of general formula (XIX)
Figure imgf000023_0001
(XIX)
wherein Rbn represents a hydrogen atom or fluorine atom, and still more preferably selected from:
pyrazole carboxamides consisting of
(b-1) Fluxapyroxad,
(b-2) Benzovindiflupyr, and
-3) a compound of formula (II)
Figure imgf000023_0002
methoxyacrylates consisting of
(b-10) Enoxastrobin,
(b-11) Pyraoxystrobin,
(b-12) Coumoxystrobin,
(b-13) Coumethoxystrobin,
(b-14) Flufenoxystrobin, and
(b-15) Pyriminostrobin;
methoxycarbamates consisting of
(b-17) Pyrametostrobin, and
(b-18) Triclopyricarb;
(b-84) Oxathiapiprolin;
(b-56) Mandestrobin; - -
(b-47) Isofetamid;
(b-78) Picarbutrazox;
(b-57) Fenaminostrobin;
(b-48) Valifenalate;
(b-49) Pyraziflumid,
Figure imgf000024_0001
compounds of general formula (XI)- 1
Figure imgf000024_0002
wherein Rbj represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group, Rb2 represents a fluorine atom or hydrogen atom, Rb3 represents a halogen atom, Rb4 represents a halogen atom, methoxy group or hydrogen atom;
(b-86) compounds of general formula (XII)
Figure imgf000024_0003
(xii)
wherein Rb5 represents a methyl group or fluorine atom;
(b-87) compounds of general formula (XIII)
Figure imgf000024_0004
wherein Rb6 represents -CH2OC(0)CH(CH3)2, -C(0)CH3, -CH2OC(0)CH3, -C(0) or
Figure imgf000025_0001
b-88) a compound of formula (XIV)
Figure imgf000025_0002
b-89) a compound of formula (XV)- 1
Figure imgf000025_0003
(b-36) compounds of general formula (V)
Figure imgf000026_0001
wherein Rb7 represents a hydrogen atom, alkyl group, amino group or cyano group, and Rb8 represents a hydrogen atom or fluorine atom;
(b-37') compounds of general formula (VP)
Figure imgf000026_0002
wherein the broken line indicates the presence or absence of a bond, represents a hydrogen atom, alkyl group, amino group or cyano group;
b-38) compounds of general formula (VII)
Figure imgf000026_0003
wherein Rb10 represents a halogen atom and Rbn represents a nitrogen atom or methine group; and
(b-79) compounds of general formula (VIII)
Figure imgf000026_0004
wherein Rbi2 represents
Figure imgf000026_0005
[0022] and further more preferably selected from: pyrazole carboxamides consisting of
(b-1) Fluxapyroxad,
(b-2) Benzovindiflupyr, and
-3) a compound of formula (II)
Figure imgf000027_0001
(b-47) Isofetamid;
(b-78) Picarbutrazox;
(b-49) Pyraziflumid,
Figure imgf000027_0002
compounds of general formula (XI)- 1
Figure imgf000027_0003
wherein Rbi represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group, Rb2 represents a fluorine atom or hydrogen atom, Rb3 represents a halogen atom, and Rb4 represents a halogen atom, methoxy group or hydrogen atom;
(b-88) a compound of formula (XIV)
Figure imgf000027_0004
b-89) a compound of formula (XV)- 1
Figure imgf000028_0001
b-36) compounds of general formula (V)
Figure imgf000028_0002
wherein Rb7 represents a hydrogen atom, alkyl group, amino group or cyano group, and Rb8 represents a hydrogen atom or fluorine atom;
(b-37') compounds of general formula (VF)
Figure imgf000028_0003
wherein the broken line indicates the presence or absence of a bond, and Rb9 represents a hydrogen atom, alkyl group, amino group or cyano group;
b-38) compounds of general formula (VII)
Figure imgf000028_0004
wherein Rb]0 represents a halogen atom and Rbn represents a nitrogen atom or methine group; and
(b-79) compounds of general formula (VIII)
Figure imgf000029_0001
wherein Rb12 represents
Figure imgf000029_0002
and most preferably selected from:
pyrazole carboxamides consisting of (b-1) Fluxapyroxad,
(b-2) Benzovindiflupyr, and
-3) a compound of formula (II)
Figure imgf000029_0003
(b-47) Isofetamid;
(b-78) Picarbutrazox;
(b-49) Pyraziflumid,
Figure imgf000029_0004
b-88) a compound of formula (XIV)
Figure imgf000029_0005
(b-38) compounds of general formula (VII)
Figure imgf000030_0001
wherein Rb10 represents a halogen atom and Rbn represents a nitrogen atom or methine group.
[0024] In any one of the preferable embodiments described above, the compound (b-36) represented by general formula (V):
Figure imgf000030_0002
is preferably a compound wherein Rb7 represents a valency that forms a double bond between a sulfur atom and a triazole ring to generate a moiety represented by:
Figure imgf000030_0003
Rb represents a fluorine atom, that is, a compound represented by formula:
Figure imgf000030_0004
[0025] Further, in any one of the preferable embodiments described above, the compound (b-38) represented by general formula (VII):
Figure imgf000030_0005
is preferably a compound wherein Rbio is a chlorine atom, and Rbn is a nitrogen atom.
[0026] Further, in any one of the preferable embodiments described above, the compound (b-86) represented by general formula (XII):
Figure imgf000031_0001
is preferably a compound wherein Rb5 is a methyl group.
[0027] Further, in any one of the preferable embodiments described above, the compound (b-85) represented by general formula (XI):
Figure imgf000031_0002
is preferably a compound represented by:
Figure imgf000031_0003
[0028] Further, in any one of the preferable embodiments described above, the compound (b-87) represented by general formula (XIII)
Figure imgf000031_0004
(XIII)
is preferably a compound wherein Rb6 is -CH2OC(0)CH(CH3)2.
[0029] Further, in any one of the preferable embodiments described above, the compound (b-89) represented by general formula (XV)
Figure imgf000032_0001
and more preferably a compound represented by:
Figure imgf000032_0002
[0030] Further, in any one of the preferable embodiments described above, the compound (b-90) represented by general formula (XVI):
Figure imgf000032_0003
is preferably a compound wherein Rb16 is a fluorine atom.
[0031] Further, in any one of the preferable embodiments described above, the compound (b-94) represented by general formula(XIX)
Figure imgf000033_0001
is preferably a compound wherein Rb17 represents a fluorine atom.
[0032] In one embodiment of the present invention, the fungicidal compounds used in combination with at least one quinoline compound represented by general formula (I) or a salt thereof is preferably selected from the group consisting of:
(b-4) Bixafen,
(b-19) Pyraclostrobin,
(b-23) Prothioconazole
(b-26) Metconazole,
(b-29) Difenoconazole,
(b-33) Triadimenol,
(b-43) Fluopyram,
(b-46) Isotianil,
(b-52) Dimoxystrobin,
(b-54) Metominostrobin,
(b-55) Trifloxystrobin,
(b-62) Pyrimethanil,
(b-69) Propineb,
(b-81) Dithianon,
(b- 101 ) Spiroxamine and
(b- 105) Phosphorous acid.
[0033] The compounds of group b are known compounds that are produced according to, for example, the methods described in International Publication No. WO
2008/145740, International Publication No. WO 2011/015416, International Publication No. WO 2011/085170, International Publication No. WO 1995/027693, International Publication No. WO 2006/016708, International Publication No. WO 2003/016303, International Publication No. WO 2006/125370, International Publication No. WO 2005/044813, International Publication No. WO 2007/000098, International Publication No. WO 2008/145052, International Publication No. WO 2006/125370, International Publication No. WO 2002/006304, International Publication No. WO 2007/072999, International Publication No. WO 1986/002641, International Publication No. WO 2007/066601, International Publication No. WO 2009/094442, International Publication No. WO 2001/014339, International Publication No. WO 2011/056463, International Publication No. WO 2012/031061, International Publication No. WO 2010/043319, International Publication No. WO 2010/136475, International Publication No. WO 2010/146006, International Publication No. WO 2012/019981, International Publication No. WO 2010/149414, International Publication No. WO 2011/070771, International Publication No. WO 2012/172061, International Publication No. WO 2010/094728, International Publication No. WO 2013/037717, International Publication No. WO 2002/012172, European Patent Publication No. 936213, U.S. Patent No. 7666884, or methods complying therewith.
[0034] The plant disease control composition of the present invention allows the obtaining of synergistic controlling effects in comparison with the case of using each of the active ingredients alone. The synergistic controlling effects and a degree thereof can be confirmed by using various test methods such as the method of Colby (see Colby SR, "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations ", Weed, 15, 1967, 20-22). This is currently a most efficacious method to determine a combination effect of two agents, and as described below in detail, during a comparison of a theoretical value calculated by Colby's formula with an actual measured effect (actual value), it is judged to be synergistic when the actual value is greater than the theoretical value, whereas to be antagonistic when the actual value is greater than the theoretical value. In the case the difference between an actual value and a theoretical value is larger, the synergistic effect is presumed to be higher. Thus, as a preferable embodiment of the present invention, there is provided a plant disease control composition comprising a combination of effective ingredients that exhibit a difference between an actual value and a theoretical value, of 5% or more, more preferably 10% or more, and still more preferably 20% or more.
[0035] Although the plant disease control composition in the present invention may be used as is, it is normally used by mixing with a carrier, and is used by formulating into a wettable powder (WP), suspension concentrate (SC), granule (GR), dustable powder (DP), soluble concentrate (SC), water dispersible granule (WG), or emulsion concentrate (EC) and the like at a suitable time according to commonly known methods by adding a formulation additive such as a dispersing agent, wetting agent, binder, thickener, preservative, colorant or stabilizer and the like as necessary. Other types of formulations known in the art are also applicable in the present invention. As used herein, the name of preparation (formulation) types and codes are essentially based on OECD Guidance Documents for Pesticide Registration (http://www.oecd.org/env/ehs/pesticides-biocides/oecdguM
egistration.htm). The content of the active ingredient in the form of the quinoline compound (I: group a compound) in these preparations is normally a weight ratio within the range of 0.005% to 99%, preferably within the range of 0.1%) to 90% and even more preferably within the range of 0.3% to 80%. In addition, the content of the active ingredient in the form of the fungicidal compound of group b in these preparations is normally a weight ratio within the range of 0.005%) to 99%, preferably within the range of 0.1 % to 90% and even more preferably within the range of 0.3% to 80%. The total of the quinoline compound (I: group a compound) and the fungicidal compound of group b is normally a weight ratio within the range of 0.01% to 99%, preferably within the range of 0.1% to 90% and even more preferably within the range of 0.3% to 80%. The mixing ratio between the quinoline compound (I: group a compound) and the fungicidal compound of group b is normally a weight ratio of the fungicidal compound of group b to the quinoline compound 1 of 0.01 to 1000 and preferably a weight ratio of the fungicidal compound of group b to the quinoline compound 1 of 0.01 to 500, more preferably 1 of 0.01 to 100, still more preferably 1 of 0.01 to 50 and most preferably 1 of 0.01 to 25. Within this range, it would be easy to find a most preferable mixing ratio of actually combined individual compounds. It would also be possible to speculate a preferable mixing ratio of similar combinations in terms of a mode of action or chemical structure of the fungicidal compound of group b, based on the measured combinations having synergistic effects.
[0036] In the plant disease control composition of the present invention, although varying according to the preparation form, the combined content of active ingredients in the form of the quinoline compound (I: group a compound) and the fungicidal compound of group b is normally 0.01%) to 30% by weight in the case of a dustable powder, 0.1%) to 80%) by weight in the case of a wettable powder, 0.5% to 20%) by weight in the case of a granule, 2% to 50% by weight in the case of an emulsion concentrate, 1%) to 50% by weight in the case of a suspension concentrate, and 1% to 80% by weight in the case of a water dispersible granule. It is preferably 0.05 to 10% by weight in the dustable powder, 5 to 60% by weight in the wettable powder, 5 to 20%) by weight in the emulsion concentrate, 5 to 50% by weight in the suspension concentrate, and 5 to 50% by weight in the water dispersible granule. The content of additives is 0% to 80%) by weight, and the content of the carrier is the amount obtained by subtracting the total content of active ingredient compounds and additives from 100% by weight.
[0037] The carrier used in the aforementioned composition refers to a synthetic or - -
natural, inorganic or organic substance that is incorporated to aid in the delivery of active ingredients to a site to be treated or to facilitate storage, transport or handling of active ingredient compounds, can be used in the form of a solid or liquid provided it is used in ordinary agri-horticultural preparations, and there are no specific limitations thereon. Examples of solid carriers include inorganic substances such as bentonite, montmorillonite, kaolinite, diatomaceous earth, kaolin, talc, clay, vermiculite, gypsum, calcium carbonate, amorphous silica or ammonium sulfate, plant-based organic substances such as soybean powder, wood meal, sawdust, wheat flour, lactose, sucrose or glucose, and urea. Examples of liquid carriers include aromatic hydrocarbons and naphthenes such as toluene, xylene or cumene, paraffin-based hydrocarbons such as n-paraffin, iso-paraffin, liquid paraffin, kerosene, mineral oil or polybutene, ketones such as acetone or methyl ethyl ketone, ethers such as dioxane or diethylene glycol dimethyl ether, alcohols such as ethanol, propanol or ethylene glycol, carbonates such as ethylene carbonate, propylene carbonate or butylene carbonate, aprotic solvents such as dimethylformamide or dimethylsulfoxide, and water.
[0038] Moreover, additives can be respectively used either alone or in combination corresponding to the purpose and in consideration of such factors as preparation form and treatment method in order to enhance the efficacy of compounds contained in the composition of the present invention. Examples of additives in the form of surfactants normally used for the purpose of emulsifying, dispersing, spreading or wetting agricultural chemical preparations include nonionic surfactants such as sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene castor oil, polyoxyethylene alkyl ethers,
polyoxyethylene alkyl phenyl ethers, polyoxyethylene dialkyl phenyl ethers, formalin condensates of polyoxyethylene alkyl phenyl ethers,
polyoxyethylene-polyoxypropylene block copolymers, alkyl
polyoxyethylene-polyoxypropylene block polymer ethers, alkyl phenyl
polyoxyethylene-polyoxypropylene block polymer ethers, polyoxyethylene alkyl amines, polyoxyethylene fatty acid amides, polyoxyethylene bisphenyl ethers, polyoxyalkylene benzyl phenyl ethers, polyoxyalkylene styryl phenyl ethers, polyoxyalkylene adducts of higher alcohols, polyoxyethylene ethers, ester-based silicone and fluorine-based surfactants; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene benzyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, polyoxyethylene-polyoxypropylene block polymer sulfates, paraffin sulfonates, alkane sulfonates, AOS, dialkyl sulfosuccinates, alkyl benzene sulfonates, naphthalene sulfonates, dialkyl naphthalene sulfonates, formalin condensates of naphthalene sulfonates, alkyl diphenyl ether disulfonates, lignin sulfonates, polyoxyethylene alkyl phenyl ether sulfonates, polyoxyethylene alkyl ether sulfosuccinate half esters, fatty acid salts, N-methyl-fatty acid sarcosinates, resin acid salts, polyoxyethylene alkyl ether phosphates, polyoxyethylene phenyl ether phosphates, polyoxyethylene dialkyl phenyl ether phosphates, polyoxyethylene benzylated phenyl ether phosphates,
polyoxyethylene benzylated phenyl phenyl ether phosphates, polyoxyethylene styrylated phenyl ether phosphates, polyoxyethylene styrylated phenyl phenyl ether phosphates, polyoxyethylene-polyoxypropylene block polymer phosphates,
phosphatidylcholine, phosphatidylethanolimine, alkyl phosphates or sodium
tripolyphosphate ; polyanionic polymer surfactants derived from acrylic acid and acrylonitrile or acrylamidomethylpropane sulfonic acid; cationic surfactants such as alkyl trimethyl ammonium chlorides, methyl polyoxyethylene alkyl ammonium chlorides, alkyl-N-methyl pyridinium bromides, monomethylated ammonium chlorides, dialkyl methylated ammonium chlorides, alkyl pentamethyl propylene amine dichlorides, alkyl dimethyl benzalkonium chlorides or benzetonium chloride; and, amphoteric surfactants such as dialkyl diaminoethyl betaines or alkyl dimethyl benzyl betaines. Examples of binders used as additives include sodium alginate, polyvinyl alcohol, gum arabic, CMC sodium and bentonite, examples of disintegrating agents include CMC sodium and croscarmellose sodium, and examples of stabilizers include hindered phenol-based antioxidants and benzotriazole-based or hindered amine-based ultraviolet absorbers. Examples of pH adjusters include phosphoric acid, acetic acid and sodium hydroxide, and examples of antibacterial and antifungal agents include industrial disinfectants and antibacterial and antifungal agents such as
l,2-benzisothiazolin-3-one. Examples of thickeners include xanthan gum, guar gum, CMC sodium, gum arabic, polyvinyl alcohol and montmorillonite. Examples of antifoaming agents include silicone-based compounds, and examples of antifreezing agents include propylene glycol and ethylene glycol. However, the additives are not limited to those listed above.
[0039] Although examples of methods used to apply the composition of the present invention include treatment by spraying the foliage of plant individuals, seedling box treatment, soil surface spraying, soil surface spraying followed by soil incorporation, soil injection, soil injection followed by soil incorporation, soil irrigation, soil irrigation followed by soil incorporation, plant seed spraying, plant seed smearing, plant seed immersion and plant seed powder coating, any type of application method routinely used by persons with ordinary skill in the art demonstrates adequate efficacy.
[0040] In addition, the method for controlling plant disease in the present invention includes applying a plant disease control composition containing a compound of group a and a fungicidal compound of group b as active ingredients, simultaneously applying a plant disease control composition containing a compound of group a as an active ingredient and a plant disease control composition containing a fungicidal compound of group b as an active ingredient, or applying one of either a plant disease control composition containing a compound of group a as an active ingredient or a plant disease control composition containing a fungicidal compound of group b as an active ingredient followed by spraying the other composition, and the amount of time (time period) from applying one of either the plant disease control composition containing a compound of group a as an active ingredient or a plant disease control composition containing a fungicidal compound of group b as an active ingredient until spraying of the other composition is, for example, 1 minute to 2 weeks after applying either one of the compositions, preferably 5 minutes to 1 week after applying either one of the compositions, and more preferably 10 minutes to 3 days after applying either one of the compositions.
[0041] Moreover, the plant disease control composition of the present invention can be prepared as a composition comprising high concentrations of the quinoline compound represented by general formula (I) and a fungicidal compound of group b. This highly concentrated composition can be used as a spray by diluting with water. In addition, the plant disease control composition of the present invention can also be prepared as a mixture by mixing a composition containing a high concentration of the quinoline compound represented by general formula (I) and a composition containing a high concentration of a fungicidal compound of group b at the time of use. This highly concentrated composition can be used as a spray by diluting with water (tank-mixing).
[0042] Although the applied amount and applied concentration of the plant disease control composition containing a quinoline compound of group a and a fungicidal compound of group b as active ingredients thereof vary according to such factors as the target crop, target disease, degree of disease proliferation, compound drug form, application method and various environmental conditions, in the case of spraying, the applied amount is normally 10 g to 10,000 g per hectare and preferably 25 g to 5,000 g per hectare in terms of the amount of active ingredients. In addition, in the case of spraying after diluting a wettable powder, suspension concentrate or emulsion concentrate with water, the dilution factor thereof is normally 5 to 50,000, preferably 10 to 20,000 and more preferably 15 to 10,000. In addition, in the case of seed disinfection, the amount of the fungicide mixture used is normally 0.001 g to 50 g and preferably 0.01 g to 10 g per 1 kg of seeds. In the case of spraying the composition of the present invention onto the foliage of plant individuals, spraying onto the surface of soil, injecting into soil or irrigating soil drench, treatment may be carried out after diluting the chemical ingredient used to a suitable concentration in a suitable carrier. In the case of contacting the composition of the present invention with plant seeds, the plant seeds may be immersed in the chemical ingredient as is. In addition, plant seeds may be immersed, powder-coated, sprayed or smeared after diluting the chemical ingredient used to a suitable concentration in a suitable carrier. Although the amount of preparation used in the case of powder-coating, spraying or smearing is normally about 0.05% to 50% and preferably 0.1% to 30% of the dry weight of the plant seeds, the amount used is not limited thereto and can be varied according to the form of the preparation and the type of plant seeds targeted for treatment. Examples of suitable carriers include, but are not limited to, liquid carriers including water or organic solvents such as ethanol;, and solid carriers in the manner of inorganic substances such as bentonite, montmorillonite, kaolinite, diatomaceous earth, kaolin, talc, clay, vermiculite, gypsum, calcium carbonate, amorphous silica or ammonium sulfate, plant-based organic substances such as soybean powder, wood meal, sawdust, wheat flour, lactose, sucrose or glucose, and urea.
[0043] Plant individuals as referred to in the present description refer to those that thrive without moving by carrying out photosynthesis, and specific examples thereof include, but are not limited to, rice, wheat, barley, corn, grapes, apples, pears, peaches, cherries, persimmons, citrus fruits, soybeans, green beans, strawberries, potatoes, cabbages, lettuces, tomatoes, cucumbers, eggplants, watermelons, beets, spinaches, peas, squashes, sugar canes, tobacco, green peppers, sweet potatoes, yams, konjac, rape, cotton, sunflowers, tulips, chrysanthemums and grasses.
[0044] Plant seeds as referred to in the present description refer to those used for agricultural propagation by storing nutrients for allowing the germination of seedlings, and specific examples thereof include, but are not limited to, corn, soybean, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, pea, squash, sugar cane, tobacco, green pepper and rape seeds, yam, potato, sweet potato and konjac seed tubers, edible lily and tulip bulbs, shallot seed bulbs, and seeds of plants created by genetic or other artificial manipulation, including soybeans, corn, rape seeds or cotton that do not inherently exist in nature and have been imparted with herbicide resistance, rice or tobacco suitable for cold climates, and seeds of transformants of corn, cotton or potatoes that have been imparted with the ability to produce insecticides. - -
[0045] The composition of the present invention can naturally be used by mixing with other agricultural chemicals, soil conditioners or fertilizers such as insecticides, miticides, nematicides, fungicides, herbicides or plant growth regulators, and can be prepared by mixing therewith. Examples of insecticides, miticides and nematicides include, but are not limited to, pyrethroid-based compounds such as acrinathrin, allethrin [(lR)-isomer], bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,
gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin,
beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin
[(lR)-trans-isomer], deltamethrin, empenthrin [(EZ)-(lR)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, methothrin, metofluthrin, permethrin, phenothrin
[(lR)-trans-isomer], prallethrin, resmethrin, RU 15525 (kadethrin), silafluofen, tefluthrin, tetramethrin, tetramethrin [(lR)-isomer], tralomethrin, transfluthrin, ZXI8901, biopermethrin, furamethrin, profluthrin, flubrocythrinate or dimefluthrin, organic phosphorous-based compounds such as acephate, azamethiphos, azinphos-methyl, azinphos-ethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, CYAP (cyanophos), demeton-S-methyl, diazinon, ECP (dichlofenthion), DDVP (dichlorvos), dicrotophos, dimethoate, dimethylvinphos, disulfoton (ethylthiometon), EPN (O-ethyl-O-4-nitrophenyl phenylphosphonothioate), ethion, ethoprophos, famphur, fenamiphos, MEP (fenitrothion), MPP (fenthion), fosthiazate, heptenophos, isofenphos-methyl, isocarbophos (isopropyl
O-(methoxyaminothio-phosphoryl)salicylate), isoxathion, malathion, mecarbam, methamidophos, DMTP (methidathion), mevinphos, monocrotophos, BRP (naled), omethoate, oxydemeton-methyl, parathion, parathion-methyl, PAP (phenthoate), phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, thiometon, triazophos, DEP (trichlorfon),
vamidothion, Bayer 22/190 (chlorothion), bromfenvinfos, bromophos,
bromophos-methyl, butathiofos, carbophenothion, chlorphoxim, sulprofos, diamidafos, CVMP (tetrachlorvinphos), propaphos, mesulfenfos, dioxabenzofos (salithion), etrimfos, oxydeprofos, formothion, fensulfothion, isazofos or imicyafos (AKD3088), oxime carbamate-based compounds such as alanycarb, butocarboxim, butoxycarboxim, thiodicarb or thiofanox, carbamate-based compounds such as aldicarb, bendiocarb, benfuracarb, NAC (carbaryl), carbofuran, carbosulfan, ethiofencarb, BPMC
(fenobucarb), formetanate, furathiocarb, MIPC (isoprocarb), methiocarb, methomyl, oxamyl, pirimicarb, PHC (propoxur), trimethacarb, XMC, allyxycarb, aldoxycarb, bufencarb, butacarb, carbanolate, MTMC (metolcarb), MPMC (xylylcarb) or
fenothiocarb, neonicotinoid-based compounds such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid or thiamethoxam,
diacylhydrazine-based compounds such as chromafenozide, halofenozide,
methoxyfenozide or tebufenozide, benzoylurea-based compounds such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron, juvenile hormone-based compounds such as fenoxycarb, hydroprene, kinoprene, methoprene or pyriproxyfen, cyclodiene organochlorine-based compounds such as chlordane, endosulfan, lindane (gamma-HCH) or dienochlor, 2-dimethylaminopropane-l,3-dithiol-based compounds such as cartap hydrochloride or thiocyclam, amidine-based compounds such as amitraz, phenylpyrazole-based compounds such as ethiprole or fipronil, organic tin-based compounds such as azocyclotin, cyhexatin or fenbutatin oxide, METI-based compounds such as fenazaquin, fenproximate, pyridaben, pyrimidifen, tebufenpyrad or tolfenpyrad, benzylate-based compounds such as bromopropylate, allyl pyrrole-based compounds such as chlorfenapyr, nitrophenol-based compounds such as DNOC, anthranilic diamide-based compounds such as chlorantraniliprole or cyantraniliprole,
oxadiazine-based compounds such as indoxacarb, semicarbazone-based compounds such as metaflumizone, tetronic acid-based compounds such as spirodiclofen or spiromesifen, carbamoyl triazole-based compounds such as triazamate, tetrazine-based compounds such as diflovidazin, as well as abamectin, acequinocyl, azadirachtin, bensultap, benzoximate, bifenazate, buprofezin, CGA 50 439, chinomethionate, clofentezine, cryolite, cyromazine, dazomet, DCIP, DDT, diafenthiuron, D-D
(1,3-dichloropropane), dicofol, dicyclanil, dinobuton, dinocap, ENT 8184, etoxazole, flonicamid, fluacrypyrim, flubendiamide, GY-81 (peroxocarbonate), hexythiazox, hydramethylnon, hydrogen cyanide, methyl iodide, karanjin, MB-599 (verbutin), silver chloride, metam, methoxychlor, methyl isothiocyanate, milbemectin, pentachlorophenol, phosphine, piperonyl butoxide, polynactins, BPPS (propargite), pymetrozine, pyrethrin, pyridalyl, rotenone, S421 (bis(2,3,3,3-tetrachloropropyl)ether), sabadilla, spinosad, sulcofuronic acid (sulcofuron-sodium), sulfluramid, tetradifon, thiosultap, tribufos, aldrin, amidithion, amidothioate, aminocarb, amiton, aramite, athidathion, azothoate, barium polysulfide, Bayer 22408, Bayer 32394, triflumezopyrim, benclothiaz,
5-(l,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone,
l,l-bis(4-chlorophenyl)-2-ethoxyethanol, butonate, butopyronoxyl,
2-(2-butoxyethoxy)ethyl thiocyanato, camphechlor, chlorbenside, chlordecone, - -
chlordimeform, chlorfenethol, chlorfenson, isoprothiolane, fluazuron, lepimectin, spinetoram, emamectin benzoate, metaldehyde, phenisobromolate, bialaphos, levamisole hydrochloride, pyrifluquinazon (N II0101), cyflumetofen, amidoflumet, IKA-2005, cyenopyrafen (NC512), spirotetramat (BYI08330), sulfoxafior, pyrafluprole (V3039), pyriprole (V3086), tetraniliprole, cyclaniliprole, momfluorothrin, heptafluthrin, pyflubumide, flometoquin, fluensulfone, meperfluthrin, tetramethylfluthrin,
kappa-bifenthrin, kappa-tefluthrin, dicloromezotiaz, flufiprole, tioxazafen,
flupyradifurone, afidopyropen, fluhexafon and tralopyril.
[0046] The composition and control method of the present invention are effective against, for example, the types of plant diseases indicated below. The following indicates those specific diseases and pathogens thereof targeted for control by the present invention.
[0047] Examples thereof include, but are not limited to, blast {Pyricularia oryzae, ), sheath blight {Thanatephorus cucumeris, Rhizoctonia solani ), brown spot
{Cochliobolus miyabeanus), "Bakanae" disease {Gibberella fujikuroi), seedling blight (Pythiwn spp., Fusarium spp., Trichoderma spp., Rhizopus spp., Rhizoctonia solani etc.), false smut {Claviceps virens) and kernel smut {Tilletia barclayana) of rice;
powdery mildew {Erysiphe graminis f.sp.hordei; f.sp. tritici), rust {Puccinia striiformis; Puccinia graminis, Puccinia recondita, Puccinia hordei), mottle leaf {Pyrenophora graminea), net blotch {Pyrenophora teres), fusarium blight {Fusarium graminearum, Fusarium culmorum, Fusarium avenaceum, Microdochium nivale), snow mould
{Typhula incarnata, Typhula ishikariensis, Micronectriella nivalis), loose kernel smut {Ustilago nuda, Ustilago tritici, Ustilago nigra, Ustilago avenae), stinking smut
{Tilletia caries, Tilletia pancicii), eye spot {Pseudocercosporella herpotrichoides), foot rot {Rhizoctonia cerealis), scald {Rhynchosporium secalis), leaf blight {Septoria tritici), glume blotch {Leptosphaeria nodorum), seedling blight {Fusarium spp., Pythium spp., Rhizoctonia spp., Septoria nodorum, Pyrenophora spp.), damping off {Gaeumanno- myces graminis), anthracnose {Colletotrichum graminicola), ergot {Claviceps purpurea) and spot blotch {Cochliobolus sativus) of family of wheat and barley; fusarium blight {Fusarium graminearum etc.), seedling blight {Fusarium avenaceum, Penicillium spp.,, Pythium spp., Rhizoctonia spp.), rust {Puccinia sorghi), brown spot {Cochliobolus heterostrophus), smut {Ustilago maydis), anthracnose {Colletotrichum graminicola) and Northern leaf spot {Cochliobolus carbonum) of corn; downy mildew {Plasmopara viticola), rust {Phakopsora ampelopsidis), powdery mildew {Uncinula necator), anthracnose {Elsinoe ampelina), ripe rot {Glomerella cingulata), black rot {Guignardia bidwellii), dead arm {Phomopsis viticola), fry speck {Zygophiala jamaicensis), gray mold (Botrytis cinerea), bud blight {Diaporthe medusaea), violet root rot (Helicobasidi m mompa) and white root rot (Rosellinia necatrix) of grape vine;
powdery mildew (Podosphaera leucotricha), scab (Venturia inaequalis), alternaria blotch (Alternaria alternata Apple pathotype), rust (Gymnosporangium yamadae), blossom blight (Monillia mali), valsa canker (Valsa ceratosperma), ring rot
(Botryosphaeria berengeriana), anthracnose (Colletotrichum acutatum), fry speck (Zygophiala jamaicensis), sooty blotch (Gloeodes pomigena), fruit spot
(Mycosphaerella pomi), violet root rot (Helicobasidium mompa), white root rot
(Rosellinia necatrix), diaporthe canker (Phomopsis mali, Diaporthe tanakae) and blotch (Diplocarpon mali) of apple; pear black spot (Alternaria alternata Japanese pear pathotype), scab (Venturia nashicola), rust (Gymnosporangium haraeanum),
Physalospora canker (Physalospora piricola) and canker (Diaporthe medusaea,
Diaporthe eres) of Japanese pear, phytophthora rot (Phytophthora cactorum) of
European pear; scab (Cladosporium carpophilum), phomopsis rot (Phomopsis sp. ), phytophthora fruit rot (Phytophthora sp.) and anthracnose (Gloeosporium laeticolor) of peach; anthracnose (Glomerella cingulata), young-fruit rot (Monilinia kusanoi) and brown rot (Monilinia fructicola) of cherry; anthracnose (Gloeosporium kaki), angular leaf spot (Cercospora kaki; Mycosphaerella nawae), powdery mildew (Phyllactinia kakikora) of persimmon; melanose (Diaporthe citri), common green mold (Penicillium digitatum), blue mold (Penicillium italicum) and scab (Elsinoe fawcettii) of citrus;
[0048] gray mold (Botrytis cinerea) of tomato, cucumber, pulse, strawberry, potato, cabbage, eggplant, lettuce, etc.; stem rot (Sclerotinia sclerotiorum) of tomato, cucumber, bean, strawberry, potato, rape, cabbage, eggplant, lettuce, etc.; seedling blight
(Rhizoctonia spp., Pythium spp., Fusarium spp., Phytophthora spp., Sclerotinia sclerotiorum etc.) of various kinds of vegetables such as tomato, cucumber, bean, Japanese radish, water melon, eggplant, rape, green pepper, spinach, sugar beet, etc.; downy mildew (Pseudoperonospora cubensis), powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum lagenarium), gummy stem blight
(Mycosphaerella melonis), fusarium wilt (Fusarium oxysporum) and phytophthora rot (Phytophthora parasitica, Phytophthora melonis, Phytophthora nicotianae, Phytophthora drechsleri, Phytophthora capsici etc.) of oriental melon; early blight
(Alternaria solani), leaf mold (Cladosporium fulvam), late blight (Phytophthora infestans), fusarium wilt (Fusarium oxysporum), root rot (Pythium myriotylum, Pythium dissotocum) and anthracnose (Colletotrichum phomoides) of tomato; powdery mildew (Sphaerotheca fuliginea etc.), leaf mold (Mycovellosiella nattrassii), late blight
(Phytophthora infestans) and brown rot (Phytophthora capsici) of eggplant; alternaria . .
leaf spot (Alternaria brassicae) of rapeseed, alternaria leaf spot {Alternaria brassicae etc.), white spot (Cercosporella brassicae), blackleg (Leptosphaeria maculans), club root (Plasmodiophora brassicae) and downy mildew (Peronospora brassicae) of Brassica vegetables; foot rot (Rhizoctonia solani), yellows (Fusarium oxysporum) of cabbage; bottom rot (Rhizoctonia solani) and yellows (Verticillium dahliae) of Chinese cabbage; rust (Puccinia allii), alternaria leaf spot (Alternaria porri), southern blight (Sclerotium rolfsii. Sclerotium rolfsii) and white tip disease (Phytophthora porri) of welsh onion; purple stain (Cercospora kikuchii), sphaceloma scab (Elsinoe glycines), black spot (Diaporthe phaseololum), rhizoctonia root rot (Rhizoctonia solani), stem rot (Phytophthora megasperma), downy mildew (Peronospora manshurica), rust
(Phakopsora pachyrhizi) and anthracnose (Colletotrichum truncatum) of soybean; anthracnose (Colletotrichum lindemuthianum) of kidney bean; leaf spot
(Mycosphaerella personatum) and brown leaf spot (Cercospora arachidicola) of peanuts; powdery mildew (Erysiphe pisi) and downy mildew (Peronospora pisi) of pea; downy mildew (Peronospora viciae) and phytophthora rot (Phytophthora nicotianae) of broad bean; early blight (Alternaria solani), black scurf (Rhizoctonia solani), late blight (Phytophthora infestans), silver scurf (Spondylocladium atrovirens), dry spot (Fusarium oxysporum, Fusarium solani) and powdery scab (Spongospora subterranea) of potato; cercospora leaf spot (Cercospora beticola), downy mildew (Peronospora schachtii), aphanomyces root rot (Aphanomyces cochlioides) and leaf spot (Phoma betae) of sugar beet; leaf blight (Alternaria dauci) of carrots; powdery mildew (Sphaerotheca humuli), phytophthora rot (Phytophthora nicotianae), anthracnose (Gromerella cingulata) and soft-rotted fruits (Pythium ultimum Trow var. ultimum) of strawberry;
net blister blight (Exobasidium reticulatum), white scab (Elsinoe leucospila), anthracnose (Colletotrichum theaesinensis) and gray blight (Pestalotiopsis longiseta) of green tea; brown spot (Alternaria alternata (Tobacco pathotype)), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum) and black shank (Phytophthora parasitica) of tobacco; damping off (Fusarium oxysporum) of cotton; sclerotinia rot (Sclerotinia sclerotiorum) of sunflower; black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), phytophthora rot (Phytophthora
megasperma) and downy mildew (Peronospora sparsa) of rose; leaf blight (Septoria chrysanthemi-indici), rust (Puccinia horiana) and phytophthora rot (Phytophthora cactorum) of chrysanthemum; or
brown patch (Rhizoctonia solani), dollar spot (Sclerotinia homoeocarpa), Curvularia leaf blight (Curvularia geniculata), rust (Puccinia zoysiae), Helminthosporium leaf blight (Cochliobolus sp.), scald (Rhynchosporium secalis), damping off _ _
{Gaeumannomyces graminis), anthracnose {Colletotrichum graminicola), typhula brown snow blight {Typhula incarnata), typhula black snow blight {Typhula
ishikariensis), sclerotinia snow blight {Sclerotinia borealis), fairy rings {Marasmius oreades etc.), pythium blight {Pythium aphanidermatum etc.) and blast {Pyricularia oryzae) of turf grass.
[0049] More preferable targets for controlling plant diseases by the present invention are blast {Pyricularia oryzae, ), brown spot {Cochliobolus miyabeanus), "Bakanae" disease {Gibberella fujikuroi), seedling blight {Pythium spp., Fusarium spp.,
Trichoderma spp., Rhizopus spp., Rhizoctonia solani etc.) and false smut {Claviceps virens) of rice; powdery mildew {Erysiphe graminis f.sp.hordei; f.sp.tritici), mottle leaf {Pyrenophora graminea), net blotch {Pyrenophora teres), fusarium blight {Fusarium graminearum, Fusarium culmorum, Fusarium avenaceum, Microdochium nivale), snow mould {Typhula incarnata, Typhula ishikariensis, Micronectriella nivalis), eye spot {Pseudocercosporella herpotrichoides), foot rot {Rhizoctonia cerealis), scald
{Rhynchosporium secalis), leaf blight {Septoria tritici), seedling blight {Fusarium spp., Pythium spp., Rhizoctonia spp., Septoria nodorum, Pyrenophora spp.), damping off {Gaeumannomyces graminis), anthracnose {Colletotrichum graminicola), ergot
{Claviceps purpurea) and spot blotch {Cochliobolus sativus) of family of wheat and barley; fusarium blight {Fusarium graminearum etc.), seedling blight {Fusarium avenaceum, Penicillium spp.,, Pythium spp., Rhizoctonia spp.), brown spot
{Cochliobolus heterostrophus) and Northern leaf spot {Cochliobolus carbonum) of corn; powdery mildew {Uncinula necator), anthracnose {Elsinoe ampelina), ripe rot
{Glomerella cingulata), black rot {Guignardia bidwellii), dead arm {Phomopsis viticola), fry speck {Zygophiala jamaicensis), gray mold {Botrytis cinerea), bud blight {Diaporthe medusaea), violet root rot {Helicobasidium mompa) and white root rot {Rosellinia necatrix) of grape vine; powdery mildew {Podosphaera leucotricha), scab {Venturia inaequalis), alternaria blotch {Alternaria alternata Apple pathotype), blossom blight {Monillia mali), valsa canker {Valsa ceratosperma), ring rot {Botryosphaeria
berengeriana), anthracnose {Colletotrichum acutatum), fry speck {Zygophiala jamaicensis), sooty blotch {Gloeodes pomigena), fruit spot {Mycosphaerella pomi), violet root rot {Helicobasidium mompa), white root rot {Rosellinia necatrix), diaporthe canker {Phomopsis mali, Diaporthe tanakae) and blotch {Diplocarpon mali) of apple; pear black spot {Alternaria alternata Japanese pear pathotype), scab {Venturia nashicola), Physalospora canker {Physalospora piricola) and canker (Diaporthe medusaea, Diaporthe eres) of Japanese pear, scab {Cladosporium carpophilum), phomopsis rot {Phomopsis sp.) and anthracnose {Gloeosporium laeticolor) of peach; - -
anthracnose (Glomerella cingulatd), young-fruit rot (Monilinia kusanoi) and brown rot {Monilinia fructicola) of cherry; anthracnose (Gloeosporium kaki), angular leaf spot {Cercospora kaki; Mycosphaerella nawae) and powdery mildew (Phyllactinia kakikora) of persimmon; melanose (Diaporthe citri), common green mold (Penicillium digitatum), blue mold (Penicillium italicum) and scab (Elsinoe fawcettii) of citrus;
[0050] gray mold (Botrytis cinerea) of tomato, cucumber, pulse, strawberry, potato, cabbage, eggplant, lettuce, etc.; stem rot (Sclerotinia sclerotiorum) of tomato, cucumber, bean, strawberry, potato, rape, cabbage, eggplant, lettuce, etc.; seedling blight
(Rhizoctonia spp., Pythium spp., Fusarium spp., Phytophthora spp., Sclerotinia sclerotiorum etc.) of various kinds of vegetables such as tomato, cucumber, bean, Japanese radish, water melon, eggplant, rape, green pepper, spinach, sugar beet, etc.; powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum lagenarium), gummy stem blight (Mycosphaerella melonis) and fusarium wilt (Fusarium oxysporum) of oriental melon; early blight (Alternaria solani), leaf mold (Cladosporium fulvam), fusarium wilt (Fusarium oxysporum) and anthracnose (Colletotrichum phomoides) of tomato; powdery mildew (Sphaerotheca fuliginea etc.), of eggplant; alternaria leaf spot (Alternaria brassicae) of rapeseed, alternaria leaf spot (Alternaria brassicae etc.), white spot (Cercosporella brassicae), blackleg (Leptosphaeria maculans) of Brassica vegetables; yellows (Fusarium oxysporum) of cabbage; yellows (Verticillium dahliae) of Chinese cabbage; alternaria leaf spot (Alternaria porri) of welsh onion; purple stain (Cercospora kikuchii), sphaceloma scab (Elsinoe glycines), black spot (Diaporthe phaseololum) and anthracnose (Colletotrichum truncatum) of soybean; anthracnose (Colletotrichum lindemuthianum) of kidney bean; leaf spot (Mycosphaerella
personatum) and brown leaf spot (Cercospora arachidicola) of peanuts; powdery mildew (Erysiphe pisi) of pea; early blight (Alternaria solani) and silver scurf
(Spondylocladium atrovirens), of potato; cercospora leaf spot (Cercospora beticola) and leaf spot (Phoma betae) of sugar beet; leaf blight (Alternaria dauci) of carrots;
powdery mildew (Sphaerotheca humuli) and anthracnose (Gromerella cingulatd) of strawberry; white scab (Elsinoe leucospila), anthracnose (Colletotrichum theaesinensis) and gray blight (Pestalotiopsis longiseta) of green tea; brown spot (Alternaria alternata (Tobacco pathotype)), powdery mildew (Erysiphe cichoracearum) and anthracnose (Colletotrichum tabacum) of tobacco; damping off (Fusarium oxysporum) of cotton; sclerotinia rot (Sclerotinia sclerotiorum) of sunflower; black spot (Diplocarpon rosae) and powdery mildew (Sphaerotheca pannosa) of rose; leaf blight (Septoria
chrysanthemi-indici) of chrysanthemum; or
dollar spot (Sclerotinia homoeocarpa), Curvularia leaf blight (Curvularia geniculata), - -
Helminthosporium leaf blight {Cochliobolus sp.), scald {Rhynchosporium secalis), damping off {Gaeumannomyces graminis), anthracnose {Colletotrichum graminicola), typhula brown snow blight {Typhula incarnata), typhula black snow blight {Typhula ishikariensis), sclerotinia snow blight {Sclerotinia borealis), fairy rings {Marasmius oreades etc.) and blast {Pyricularia oryzae) of turf grass.
EXAMPLES
[0051] The following provides a more detailed explanation of the present invention by listing preparation examples and test examples thereof. However, the present invention is not limited to only these preparation examples and test examples.
Furthermore, the number of parts of all incorporated amounts of each component described in the following preparation examples refers to parts by weight.
[0052] Compound A (a-14), B (a-18) and C (a-20) among the compounds (I: group a) used in the following preparation examples and test examples respectively refer to Compound Nos. 1-866, 1-929 and 1-930 of International Publication No. WO
2005/070917, and are respectively described therein in Examples 114, 177 and 178. The chemical structures thereof are shown in Table 1.
[0053] [Table 1]
Figure imgf000047_0002
[0054] In addition, the fungicidal compound of formula (VII)- 1 of compound (b-38) used in the following preparation examples and test examples is a compound represented by the following formula.
Figure imgf000047_0001
[0055] Preparation Example 1 Wettable powder (WP) (al)
Component 1 (group a) in the form of any of Compounds A, B and C (10, 1 or 0.01 parts), Component II (group b) in the form of any of the compounds described below (added amount indicated), Neogen powder (0.5 parts), Carplex (0.5 parts), Gohsenol (0.2 parts), Radiolite (0.8 parts) and H fine powder (used as the balance to bring to a total of 100 parts) were crushed and mixed to obtain wettable powder (al). - -
[0056] The compounds (added amounts) used for Component II (group b) consisted of (b-1) (2 parts), (b-2) (2 parts), (b-3) (2 parts), (b-4)(2 to 10 parts), (b-5) (2 to 50 parts), (b-6) (0.4 to 50 parts), (b-7) (0.4 to 50 parts), (b-8)(0.4 to 2 parts), (b-9)(0.4 to 2 parts), (b-16)(2 parts), (b-19)(2 parts), (b-20) (0.4 to 10 parts), (b-21) (0.4 to 10 parts), (b-22) (0.4 to 10 parts), (b-23)(2 to 10 parts), (b-24) (0.4 to 10 parts), (b-25) (0.4 to 10 parts), (b-26) (0.4 to 10 parts), (b-27) (0.4 to 10 parts), (b-28) (0.4 to 10 parts), (b-29) (0.4 to 10 parts), (b-30) (0.4 to 10 parts), (b-31) (0.4 to 10 parts), (b-32) (0.4 to 10 parts), (b-33)( 25 to 50 parts), (b-34) (0.4 to 10 parts), (b-35) (0.4 to 10 parts), (b-36) (0.4 to 10 parts), (b-38) (2 parts), (b-39) (0.4 parts), (b-40) (2 parts), (b-41) (50 parts), (b-42) (50 parts), (b-43)(2 to 10 parts), (b-44) (0.08 parts), (b-45) (10 parts), (b-46)(2 to 10 parts), (b-47) (10 parts), (b-49) (2 parts), (b-50) (2 parts), (b-51) (2 to 50 parts), (b-52) (2 to 50 parts), (b-53) (2 to 50 parts), (b-54)(2 parts), (b-55)(2 to 10 parts), (b-58) (10 to 50 parts), (b-59) (2 parts), (b-60) (10 to 50 parts), (b-61) (10 to 50 parts), (b-62)(10 to 50 parts), (b-63) (0.016 to 50 parts), (b-64) (10 parts), (b-65) (0.4 to 50 parts), (b-66) (0.4 to 50 parts), (b-67) (50 parts), (b-68) (50 parts), (b-69) (50 parts), (b-70) (50 parts), (b-71) (10 to 50 parts), (b-72)(2 to 10 parts), (b-73) (10 parts), (b-74) (0.4 to 50 parts), (b-75) (2 parts), (b-76) (25 parts), (b-77) (0.016 to 50 parts), (b-78) (0.4 parts), (b-81) (2 to 50 parts), (b-82) (0.08 to 50 parts), (b-83)(0.08 to 10 parts), (b-84)(0.0016 to 50 parts), (b-85)(10 parts), (b-88) (2 parts), (b-89)(2 parts), (b-91)(0.08 to 2 parts), (b-92)(0.4 parts), (b-93) (50 parts), (b-94)(0.4 to 10 parts), (b-95) (2 parts), (b-96) (10 to 50 parts), (b-97) (0.08 parts), (b-98) (2 parts), (b-99) (10 to 50 parts), (b-100) (0.016 to 50 parts), (b-101) (0.4 to 50 parts), (b-102) (0.4 to 50 parts), (b-103) (10 to 50 parts), (b-104) (50 parts), (b-105) (25 to 50 parts), (b-106) (25 parts).
[0057] Preparation Example 2 Suspension concentrate (SC) (bl)
Component 1 (group a) in the form of any of Compounds A, B and C (10 or 1 parts), Component II (group b) in the form of any of the compounds described below (added amount indicated), propylene glycol (7 parts), sodium lignin sulfonate (4 parts), sodium dioctylsulfosuccinate (2 parts) and water (used as the balance to bring to a total of 100 parts) were wet-crushed with a sand grinder to obtain suspension concentrate (bl).
[0058] The compounds (added amounts) used for Component II (group b) consisted of (b-1) (2 parts), (b-2) (2 parts), (b-3) (2 parts), (b-4)(2 to 10 parts), (b-5) (2 to 50 parts), (b-6) (0.4 to 50 parts), (b-7) (0.4 to 50 parts), (b-8)(0.4 to 2 parts), (b-9)(0.4 to 2 parts), (b-16)(2 parts), (b-19)(2 parts), (b-20) (0.4 to 10 parts), (b-21) (0.4 to 10 parts), (b-22) (0.4 to 10 parts), (b-23)(2 to 10 parts), (b-24) (0.4 tolO parts), (b-25) (0.4 to 10 parts), (b-26) (0.4 to 10 parts), (b-27) (0.4 to 10 parts), (b-28) (0.4 to 10 parts), (b-29) (0.4 to - 7 -
10 parts), (b-30) (0.4 to 10 parts), (b-31) (0.4 to 10 parts), (b-32) (0.4 to 10 parts), (b-33)( 25 to 50parts), (b-34) (0.4 to 10 parts), (b-35) (0.4 to 10 parts), (b-36) (0.4 to 10 parts), (b-38) (2 parts), (b-39) (0.4 parts), (b-40) (2 parts), (b-41) (50 parts), (b-42) (50 parts), (b-43)(2 to 10 parts), (b-44) (0.08 parts), (b-45) (10 parts), (b-46)(2 to 10 parts), (b-47) (10 parts), (b-49) (2 parts), (b-50) (2 parts), (b-51) (2 to 50 parts), (b-52) (2 to 50 parts), (b-53) (2 to 50 parts), (b-54)(2 parts), (b-55)(2 to 10 parts), (b-58) (10 to 50 parts), (b-59) (2 parts), (b-60) (10 to 50 parts), (b-61) (10 to 50 parts), (b-62)(10 to 50 parts), (b-63) (0.016 to 50 parts), (b-64) (10 parts), (b-65) (0.4 to 50 parts), (b-66) (0.4 to 50 parts), (b-67) (50 parts), (b-68) (50 parts), (b-69) (50 parts), (b-70) (50 parts), (b-71) (10 to 50 parts), (b-72)(2 to 10 parts), (b-73) (10 parts), (b-74) (0.4 to 50 parts), (b-75) (2 parts), (b-76) (25 parts), (b-77) (0.016 to 50 parts), (b-78) (0.4 parts), (b-81) (2 to 50 parts), (b-82) (0.08 to 50 parts), (b-83)(0.08 to 10 parts), (b-84)(0.0016 to 50 parts), (b-85)(10 parts), (b-88) (2 parts), (b-89)(2 parts), (b-91)(0.08 to 2 parts), (b-92)(0.4 parts), (b-94)(0.4 to 10 parts), (b-95) (2 parts), (b-96) (10 to 50 parts), (b-97) (0.08 parts), (b-98) (2 parts), (b-99) (10 to 50 parts), (b-100) (0.016 to 50 parts), (b-101) (0.4 to 50 parts), (b-102) (0.4 to 50 parts), (b-103) (10 to 50 parts), (b-104) (50 parts), (b-105) (25 to 50 parts), (b-106) (25 parts).
[0059] Preparation Example 3 Emulsion concentrate (EC) (cl)
Component 1 (group a) in the form of any of Compounds A, B and C (10 or 1 parts), Component II (group b) in the form of any of the compounds described below (added amount indicated), cyclohexane (10 parts), Tween20 (surfactant, 20 parts) and xylene (used as the balance to bring to a total of 100 parts) were uniformly dissolved and mixed to obtain emulsion concentrate (cl ).
[0060] The compounds (added amounts) used for Component II (group b) consisted of (b-1) (2 parts), (b-2) (2 parts), (b-3) (2 parts), (b-4)(2 to 10 parts), (b-5) (2 to 50 parts), (b-6) (0.4 to 50 parts), (b-7) (0.4 to 50 parts), (b-8)(0.4 to 2 parts), (b-9)(0.4 to 2 parts), (b-16)(2 parts), (b-19)(2 parts), (b-20) (0.4 to 10 parts), (b-21) (0.4 to 10 parts), (b-22) (0.4 to 10 parts), (b-23)(2 to 10 parts), (b-24) (0.4 to 10 parts), (b-25) (0.4 to 10 parts), (b-26) (0.4 to 10 parts), (b-27) (0.4 to 10 parts), (b-28) (0.4 to 10 parts), (b-29) (0.4 to 10 parts), (b-30) (0.4 to 10 parts), (b-31) (0.4 to 10 parts); (b-32) (0.4 to 10 parts),
(b-33)( 25 to 50 parts), (b-34) (0.4 to 10 parts), (b-35) (0.4 to 10 parts), (b-36) (0.4 to 10 parts), (b-38) (2 parts), (b-39) (0.4 parts), (b-40) (2 parts), (b-41) (50 parts), (b-42) (50 parts), (b-43)(2 to 10 parts), (b-44) (0.08 parts), (b-45) (10 parts), (b-46)(2 to 10 parts), (b-47) (10 parts), (b-49) (2 parts), (b-50) (2 parts), (b-51) (2 to 50 parts), (b-52) (2 to 50 parts), (b-53) (2 to 50 parts), (b-54)(2 parts), (b-55)(2 to 10 parts), (b-58) (10 to 50 parts), (b-59) (2 parts), (b-60) (10 to 50 parts), (b-61) (10 to 50 parts), (b-62)(10 to 50 _ _
parts), (b-63) (0.016 to 50 parts), (b-64) (10 parts), (b-65) (0.4 to 50 parts), (b-66) (0.4 to 50 parts), (b-67) (50 parts), (b-68) (50 parts), (b-69) (50 parts), (b-70) (50 parts), (b-71) (10 to 50 parts), (b-72)(2 to 10 parts), (b-73) (10 parts), (b-74) (0.4 to 50 parts), (b-75) (2 parts), (b-76) (25 parts), (b-77) (0.016 to 50 parts), (b-78) (0.4 parts), (b-81) (2 to 50 parts), (b-82) (0.08 to 50 parts), (b-83)(0.08 to 10 parts), (b-84)(0.0016 to 50 parts), (b-85)(10 parts), (b-88) (2 parts), (b-89)(2 parts), (b-91)(0.08 to 2 parts),
(b-92)(0.4 parts), (b-94)(0.4 to 10 parts), (b-95) (2 parts), (b-96) (10 to 50 parts), (b-97) (0.08 parts), (b-98) (2 parts), (b-99) (10 to 50 parts), (b-100) (0.016 to 50 parts), (b-101) (0.4 to 50 parts), (b-102) (0.4 to 50 parts), (b-103) (10 to 50 parts), (b-104) (50 parts), (b-105) (25 to 50 parts), (b-106) (25 parts).
[0061] Comparative Preparation Example 1 Wettable powder (WP) (a2)
Water-dispersible powder (a2) was obtained using the same method as
Preparation Example 1 with the exception of containing only one of either Component I (group a) or Component II (group b).
[0062] Comparative Preparation Example 2 Suspension concentrate (SC) (b2)
Suspension concentrate preparation (b2) was obtained using the same method as Preparation Example 2 with the exception of containing only one of either
Component I (group a) or Component II (group b).
[0063] Comparative Preparation Example 3 Emulsion concentrate (EC) (c2)
Emulsion (c2) was obtained using the same method as Preparation Example 3 with the exception of containing only one of either Component I (group a) or
Component II (group b).
[0064] Comparative Preparation Example 4 Wettable powder (WP) (a3)
Water-dispersible powder (a3) was obtained using the same method as
Preparation Example 1 with the exception of containing Component II (group b) compounds described below in place of those used for Wettable powder (WP) (al). The compounds (added amounts) used for Component II (group b) consisted of
Diclocymet (0.4 to 50 parts), Carpropamid (0.4 1 50 parts), Tolclofos-methyl (10 to 50 parts), and Oxolinic acid (50 parts).
[0065] Test Example 1 Tomato Gray Mold Preventive Test
Tomato plants (variety: Ohgata Fukuju) planted in plastic pots having a diameter of 5 cm were grown indoors to the second to third leaf stage. Wettable powder prepared in compliance with Preparation Example 1 and Comparative Preparation Example 1 containing the compounds indicated in Table 2 were diluted with water to a prescribed concentration followed by spraying with a sprayer in 5 ml aliquots per 2 pots. After the chemical had dried, a conidia suspension of Botrytis cinerea which prepared from previously cultured in PDA medium was inoculated by spraying onto the plants. Following inoculation, the pots were placed in the humidified chamber of an artificial inoculation room (25 °C) and after 2 days, the pots were taken out and controlling effects were examined. During the examination, the percentage of affected area exhibiting lesions on a single tomato leaf was determined in accordance with the following incidence degree indicators. In addition, control values were calculated according to the equation indicated below from the average incidence degree of each treated group. The spray test results and theoretical values as determined according to Colby's formula are shown in Table 2.
[0066] Incidence Degree Indicators
Indicator Incidence Degree
0 No lesions
0.5 Lesion area of about 1% to 2%
1 Lesion area of less than 5%
2 Lesion area of less than 25%
3 Lesion area of less than 50%
4 Lesion area of less than 75%
5 Lesion area of less than 95%
6 Lesion area of 95% or more or withered
Furthermore, the average values of each treated group and an untreated group were used for incidence degree.
[0067] Control values were calculated from the equation indicated below.
Control value = (1 - leaflet incidence rate of treated
group/leaflet incidence rate of untreated group) x 100
Furthermore, synergistic effects were evaluated using Colby's formula.
Colby's formula is expressed as X = P + Q - P x Q/100, where X represents the theoretical value of the control value, P represents the control value in the case of spraying a certain chemical agent alone, and Q represents the control value in the case of spraying the chemical agent used in combination alone. In the case the actual measured effect is greater than the effect X as calculated with the aforementioned Colby's formula, the action resulting from combining two types of active ingredients is indicated to be more than additive, that is, to be synergistic.
[0068] [Table 2-1]
Effective ingredient Treatment
Figure imgf000051_0001
- -
formula (II) (b-3)
A+ Picarbutrazox (b-78) 10 + 0.4 86 64
A+ Compound of 10 + 2
89 69 formula (XIV) (b-88)
A+ Compound of 10 + 2
82 67 formula (VII)- 1 (b-38)
B+ Compound of 10 + 2
79 57 formula (II) (b-3)
B+ Picarbutrazox (b-78) 10 + 0.4 86 57
B+ Compound of 10 + 2
79 63 formula (XIV) (b-88)
B+ Compound of 10 + 2
82 60 formula (VII)- 1 (b-38)
C+ Compound of 10 + 2
79 57 formula (II) (b-3)
C+ Picarbutrazox (b-78) 10 + 0.4 75 57
C+ Compound of 10 + 2
82 63 formula (XIV) (b-88)
C+ Compound of 10 + 2
82 60 formula (VII)- 1 (b-38)
Compound of 2
0
formula (II) (b-3)
Picarbutrazox (b-78) 0.4 0
Compound of 2
14
formula (XIV) (b-88)
Compound of 2
7
formula (VII)- 1 (b-38)
A 10 64
B 10 57
C 10 57
[0069] [Table 2-2]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Fluoxastrobin (b-51) 10 + 50 97 86
A+ Dimoxystrobin (b-52) 10 + 50 97 81 A+ Orysastrobin (b-53) 10 + 50 100 88
B+ Fluoxastrobin (b-51) 10 + 50 100 86
B+ Dimoxystrobin (b-52) 10 + 50 97 81 B+ Orysastrobin (b-53) 10 + 50 100 88
C+ Fluoxastrobin (b-51) 10 + 50 97 84
C+ Dimoxystrobin (b-52) 10 + 50 97 78 C+ Orysastrobin (b-53) 10 + 50 100 86
Fluoxastrobin (b-51) 50 40
Dimoxystrobin (b-52) 50 17
Orysastrobin (b-53) 50 47 - -
A 10 77
B 10 77
C 10 73
[0070] [Table 2-3]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Carboxin (b-41) 10 + 50 97 75
A+ Thifluzamide (b-42) 10 + 50 100 77
A+ Isopyrazam (b-7) 10 + 50 100 82
A+ Sedaxane (b-6) 10 + 50 97 85
A+ Penflufen (b-5) 10 + 50 100 84
A+ Cyprodinil (b-61) 10 + 50 97 85
A+ Fenpyrazamine (b-99) 10 + 10 97 84
B+ Carboxin (b-41) 10 + 50 97 75
B+ Thifluzamide (b-42) 10 + 50 97 77
B+ Isopyrazam (b-7) 10 + 50 97 82
B+ Sedaxane (b-6) 10 + 50 100 85
B+ Penflufen (b-5) 10 + 50 100 84
B+ Cyprodinil (b-61) 10 + 50 100 85
B+ Fenpyrazamine (b-99) 10 + 10 97 84
C+ Carboxin (b-41) 10 + 50 100 67
C+ Thifluzamide (b-42) 10 + 50 100 69
C+ Isopyrazam (b-7) 10 + 50 97 76
C+ Sedaxane (b-6) 10 + 50 100 80
C+ Penflufen (b-5) 10 + 50 97 79
C+ Cyprodinil (b-61) 10 + 50 97 80
C+ Fenpyrazamine (b-99) 10 + 10 97 79
Carboxin (b-41) 50 17
Thifluzamide (b-42) 50 23
Isopyrazam (b-7) 50 40
Sedaxane (b-6) 50 50
Penflufen (b-5) 50 47
Cyprodinil (b-61) 50 50
Fenpyrazamine (b-99) 10 47
A 10 70
B 10 70
C 10 60
[0071] [Table 2-4]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Tetraconazole (b-22) 10 + 10 97 84
A+ Epoxiconazole (b-24) 10 + 10 100 82
A+ Ipconazole (b-25) 10 + 10 100 84 - -
A+ Metconazole (b-26) 10+10 97 84
A+ Propiconazole (b-27) 10+10 100 82
A+ Cyproconazole (b-28) 10+10 100 82
A+ Difenoconazole (b-29) 10 + 10 97 84
A+ Fluquinconazole (b-30) 10+10 100 84
A+Flusilazole(b-31) 10+10 100 82
A+ Penconazole(b-32) 10+10 97 78
A+ Flutriafol (b-34) 10+10 97 82
A+ Myclobutanil (b-35) 10+10 100 82
A+ Imazalil (b-20) 10+10 100 78
A+Prochloraz(b-21) 10+10 100 78
B+ Tetraconazole (b-22) 10+10 100 84
B+ Epoxiconazole (b-24) 10+10 100 82
B+ Ipconazole (b-25) 10+10 97 84
B+ Metconazole (b-26) 10+10 100 84
B+ Propiconazole (b-27) 10+10 100 82
B+ Cyproconazole (b-28) 10+10 100 78
B+ Difenoconazole (b-29) 10+10 97 82
B+ Fluquinconazole (b-30) 10+10 97 82
B+ Flusilazole (b-31) 10+10 100 78
B+ Penconazole(b-32) 10+10 100 78
B+ Flutriafol (b-34) 10+10 100 82
B+ Myclobutanil (b-35) 10+10 100 78
B+ Imazalil (b-20) 10+10 97 78
B+ Prochloraz(b-21) 10+10 100 78
C+ Tetraconazole (b-22) 10 + 10 100 82
C+ Epoxiconazole (b-24) 10+10 100 80
C+ Ipconazole (b-25) 10+10 100 82
C+ Metconazole (b-26) 10+10 100 82
C+ Propiconazole (b-27) 10+10 97 80
C+ Cyproconazole (b-28) 10+10 97 75
C+ Difenoconazole (b-29) 10+10 97 80
C+ Fluquinconazole (b-30) 10+10 100 80
C+ Flusilazole (b-31) 10+10 97 75
C+ Penconazole(b-32) 10+10 100 75
C+ Flutriafol (b-34) 10+10 100 80
C+ Myclobutanil (b-35) 10 + 10 100 75
C+ Imazalil (b-20) 10+10 97 75
C+ Prochloraz(b-21) 10+10 97 75
Tetraconazole (b-22) 10 40
Epoxiconazole (b-24) 10 33
Ipconazole (b-25) 10 40
Metconazole (b-26) 10 40
Propiconazole (b-27) 10 33
Cyproconazole (b-28) 10 17
Difenoconazole (b-29) 10 33
Fluquinconazole (b-30) 10 33 _ _
Flusilazole (b-31) 10 17
Penconazole(b-32) 10 17
Flutriafol (b-34) 10 33
Myclobutanil (b-35) 10 17
Imazalil (b-20) 10 17
Prochloraz(b-21) 10 17
A 10 73
B 10 73
C 10 70
[0072] [Table 2-5]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Thiabendazole (b-60) 10 + 50 100 87
A+ Benomyl (b-58) 10 + 50 100 88
A+ Thiuram (b-68) 10 + 50 100 90
A+ Metiram (b-67) 10 + 50 100 90
A+ Folpet (b-70) 10 + 50 100 92
A+ Pyrisoxazole (b-103) 10 + 10 100 82
B+ Thiabendazole (b-60) 10 + 50 100 87
B+ Benomyl (b-58) 10 + 50 100 88
B+ Thiuram (b-68) 10 + 50 100 90
B+ Metiram (b-67) 10 + 50 100 90
B+ Folpet (b-70) 10 + 50 100 92
B+ Pyrisoxazole (b-103) 10 + 10 97 82
C+ Thiabendazole (b-60) 10 + 50 100 87
C+ Benomyl (b-58) 10 + 50 100 88
C+ Thiuram (b-68) 10 + 50 100 90
C+ Metiram (b-67) 10 + 50 100 90
C+ Folpet (b-70) 10 + 50 100 92
C+ Pyrisoxazole (b-103) 10 + 10 97 82
Thiabendazole (b-60) 50 57
Benomyl (b-58) 50 60
Thiuram (b-68) 50 67
Metiram (b-67) 50 67
Folpet (b-70) 50 73
Pyrisoxazole (b-103) 10 40
A 10 70
B 10 70
C 10 70
[0073] [Table 2-6]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Fenpropimorph (b-65) 10 + 50 97 78 A+ Tridemorph (b-66) 10 + 50 100 78
A+ Metrafenone (b-82) 10 + 50 100 73
A+ Quinoxyfen (b-63) 10 + 50 100 78
A+ Flutianil (b-77) 10 + 50 100 78
A+ Proquinazid (b-100) 10 + 50 100 78
A+ Spiroxamine (b- 101) 10 + 50 100 78
A+ Fenpropidin (b-102) 10 + 50 100 78
A+ Sulfur (b-96) 10 + 50 100 73
A+ Chinomethionat (b-74) 10 + 50 100 78
B+ Fenpropimorph (b-65) 10 + 50 100 83
B+ Tridemorph (b-66) 10 + 50 100 83
B+ Metrafenone (b-82) 10 + 50 97 80
B+ Quinoxyfen (b-63) 10 + 50 100 83
B+ Flutianil (b-77) 10 + 50 100 83
B+ Proquinazid (b-100) 10 + 50 100 83
B+ Spiroxamine (b- 101) 10 + 50 100 83
B+ Fenpropidin (b-102) 10 + 50 100 83
B+ Sulfur (b-96) 10 + 50 97 80
B+ Chinomethionat (b-74) 10 + 50 100 83
C+ Fenpropimorph (b-65) 10 + 50 100 81
C+ Tridemorph (b-66) 10 + 50 100 81
C+ Metrafenone (b-82) 10 + 50 100 77
C+ Quinoxyfen (b-63) 10 + 50 100 81
C+ Flutianil (b-77) 10 + 50 100 81
C+ Proquinazid (b-100) 10 + 50 97 81
C+ Spiroxamine (b-101) 10 + 50 100 81
C+ Fenpropidin (b-102) 10 + 50 97 81
C+ Sulfur (b-96) 10 + 50 100 77
C+ Chinomethionat (b-74) 10 + 50 100 81
Fenpropimorph (b-65) 50 17
Tridemorph (b-66) 50 17
Metrafenone (b-82) 50 0
Quinoxyfen (b-63) 50 17
Flutianil (b-77) 50 17
Proquinazid (b-100) 50 17
Spiroxamine (b-101) 50 17
Fenpropidin (b-102) 50 17
Sulfur (b-96) 50 0
Chinomethionat (b-74) 50 17
A 10 73
B 10 80
C 10 77
[0074] [Table 2-7]
Treatment
Effective ingredient Preventive Theoretical concentration
in the preparation value value
(ppm) - -
A+ Trifloxystrobin (b-55) 10 + 10 100 78
A+ Bixafen (b-4) 10 + 2 100 78
A+ Fluopyram (b-43) 10 + 2 97 80
A+ Prothioconazole (b-23) 10 + 2 97 78
A+ Triadimenol (b-33) 10 + 50 97 72
A+ Pyrimethanil (b-62) 10 + 10 97 78
A+ Dithianon (b-81) 10 + 50 100 78
B+ Trifloxystrobin (b-55) 10 + 10 97 78
B+ Bixafen (b-4) 10 + 2 100 78
B+ Fluopyram (b-43) 10 + 2 97 80
B+ Prothioconazole (b-23) 10 + 2 100 78
B+ Triadimenol (b-33) 10 + 50 100 72
B+ Pyrimethanil (b-62) 10 + 10 100 78
B+ Dithianon (b-81) 10 + 50 97 78
C+ Trifloxystrobin (b-55) 10 + 10 100 78
C+ Bixafen (b-4) 10 + 2 97 78
C+ Fluopyram (b-43) 10 + 2 100 80
C+ Prothioconazole (b-23) 10 + 2 97 78
C+ Triadimenol (b-33) 10 + 50 100 72
C+ Pyrimethanil (b-62) 10 + 10 100 78
C+ Dithianon (b-81) 10 + 50 97 78
Trifloxystrobin (b-55) 10 33
Bixafen (b-4) 2 33
Fluopyram (b-43) 2 40
Prothioconazole (b-23) 2 33
Triadimenol (b-33) 50 17
Pyrimethanil (b-62) 10 33
Dithianon (b-81) 50 33
A 10 67
B 10 67
C 10 67
[0075] [Table 2-8]
Treatment
Effective ingredient Preventive Theoretical concentration
in the preparation value value
(ppm)
A+ Pyriofenone (b-83) 10 + 10 97 78
A+Compound of
10 + 2 100 80 formula (XV)- 1 (b-89)
A+ Oxathiapiprolin (b-84) 10 + 50 97 78
A+ Compound of
10 + 0.4 100 80 formula (XIX) (b-94)
A+ Compound of
10 + 2 100 80 formula (XVII) (b-91)
A+ Compound of
10 + 2 100 80 formula (III) (b-8) _ _
A+ Compound of
10 + 2 100 80 formula (IV) (b-9)
A+ Fluxapyroxad (b-1) 10 + 2 100 78
A+ Benzovindiflupyr (b-2) 10 + 2 97 80
A+ Carbendazim (b-59) 10 + 2 100 80
A+ Pyribencarb (b-98) 10 + 2 97 80
A+ Pyraziflumid (b-49) 10 + 2 97 80
B+ Pyriofenone (b-83) 10 + 10 93 78
B+Compound of
10 + 2 100 80 formula (XV)- 1 (b-89)
B+ Oxathiapiprolin (b-84) 10 + 50 100 78
B+ Compound of
10 + 0.4 97 80 formula (XIX) (b-94)
B+ Compound of
10 + 2 100 80 formula (XVII) (b-91)
B+ Compound of
10 + 2 100 80 formula (III) (b-8)
B+ Compound of
10 + 2 97 80 formula (IV) (b-9)
B+ Fluxapyroxad (b-1) 10 + 2 97 78
B+ Benzovindiflupyr (b-2) 10 + 2 97 80
B+ Carbendazim (b-59) 10 + 2 100 80
B+ Pyribencarb (b-98) 10 + 2 100 80
B+ Pyraziflumid (b-49) 10 + 2 97 80
C+ Pyriofenone (b-83) 10 + 10 100 80
C+Compound of
10 + 2 100 82 formula (XV)- 1 (b-89)
C+ Oxathiapiprolin (b-84) 10 + 50 97 80
C+ Compound of
10 + 0.4 100 82 formula (XIX) (b-94)
C+ Compound of
10 + 2 100 82 formula (XVII) (b-91)
C+ Compound of
10 + 2 100 82 formula (III) (b-8)
C+ Compound of
10 + 2 100 82 formula (IV) (b-9)
C+ Fluxapyroxad (b-1) 10 + 2 100 80
C+ Benzovindiflupyr (b-2) 10 + 2 100 82
C+ Carbendazim (b-59) 10 + 2 100 82
C+ Pyribencarb (b-98) 10 + 2 97 82
C+ Pyraziflumid (b-49) 10 + 2 97 82
Pyriofenone (b-83) 10 33
Compound of 2 40
formula (XV)- 1 (b-89)
Oxathiapiprolin (b-84) 50 33
Compound of
0.4 40
formula (XIX) (b-94) _ _
Compound of
40
formula (XVII) (b-91)
Compound of
40
formula (III) (b-8)
Compound of
40
formula (IV) (b-9)
Fluxapyroxad (b-1) 2 33
Benzovindiflupyr (b-2) 2 40
Carbendazim (b-59) 2 40
Pyribencarb (b-98) 2 40
Pyraziflumid (b-49) 2 40
A 10 40
B 10 40
C 10 40
[0076] [Table 2-9]
Treatment
Effective ingredient Preventive Theoretical concentration
in the preparation value value
(ppm)
A+ Phosphorous acid (b-105) 10 + 250 93 82
A+ Propineb (b-69) 10 + 50 93 82
A+ (b-36) 10 + 10 100 84
A+ (b-88) 10 + 0.4 97 87
A+ Compound of
10 + 10 97 87
(XI)- 1 (b-85)
A+ Compound of
10 + 10 97 87
(XI)-2 (b-85)
A+ Compound of
10 + 0.4 97 87
(XVIII) (b-92)
A+ D-tagatose (b-93) 10 + 5000 93 82
B+ Phosphorous acid (b-105) 10 + 250 97 82
B+ Propineb (b-69) 10 + 50 97 82
B+ (b-36) 10 + 10 100 84
B+ (b-88) 10 + 0.4 97 87
B+ Compound of
10 + 10 97 87
(XI)-l (b-85)
B+ Compound of
10 + 10 97 87
(XI)-2 (b-85)
B+ Compound of
10 + 0.4 97 87
(XVIII) (b-92)
B+ D-tagatose (b-93) 10 + 5000 93 82
C+ Phosphorous acid (b-105) 10 + 250 93 82
C+ Propineb (b-69) 10 + 50 93 82
C+ (b-36) 10 + 10 97 84
C+ (b-88) 10 + 0.4 97 87
C+ Compound of
10 + 10 97 87
(XI)- 1 (b-85) - -
C+ Compound of
10 + 10 97 87
(XI)-2 (b-85)
C+ Compound of
10 + 0.4 93 87
(XVIII) (b-92)
C+ D-tagatose (b-93) 10 + 5000 93 82
Phosphorous acid (b-105) 250 33
Propineb (b-69) 50 33
Compound of
10 40
(V) (b-36)
Compound of
0.4 50
(XIV) (b-88)
Compound of
10 50
(XI)- 1 (b-85)
Compound of
10 50
(XI)-2 (b-85)
Compound of
0.4 50
(XVIII) (b-92)
D-tagatose (b-93) 5000 33
A 10 73
B 10 73
C 10 73
[0077] Based on the results shown in Tables 2-1 to 2-9 above, synergistic effects were determined to be obtained when Compound A, Compound B or Compound C is used in combination with a compound of group b. Furthermore, there were no symptoms of chemical damage observed on the plant bodies or tomatoes (variety: Ohgata Fukuju) even when Compound A, Compound B or Compound C was used in combination with a compound of group b.
[0078] Comparative Example 1 Tomato Gray Mold Preventive Test
Wettable powder prepared in compliance with Comparative Preparation Example 4 containing the compounds indicated in Table 2-10 were spraied to the tomato leaves, a conidia suspension of Botrytis cinerea was inoculated onto the plants, and the controlling effects were examined in a manner similar to Test Example 1. The results and theoretical values as determined according to Colby's formula are shown in Table 2-10.
[0079] [Table 2-10]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Diclocymet 10 + 50 60 72
A+ Carpropamid 10 + 50 67 72
A+ Tolclofos-methyl 10 + 50 67 72
A+ Oxolinic acid 10 + 50 60 72 B+ Diclocymet 10 + 50 67 72
B+ Carpropamid 10 + 50 67 72
B+ Tolclofos-methyl 10 + 50 60 72
B+ Oxolinic acid 10 + 50 60 72
C+ Diclocymet 10 + 50 60 72
C+ Carpropamid 10 + 50 60 72
C+ Tolclofos-methyl 10 + 50 60 72
C+ Oxolinic acid 10 + 50 63 72
Diclocymet 50 17
Carpropamid 50 17
Tolclofos-methyl 50 17
Oxolinic acid 50 17
A 10 67
B 10 67
C 10 67
[0080] Based on the results shown in Tables 2-10 above, even if these compounds are used in combination with Compound A, Compound B or Compound C, the controlling effects were under their theoretical values and the action resulting from combining two types of active ingredients is indicated to be antagonistic.
[0081] Test Example 2 Rice Blast Preventive Test
Rice plants (variety: Sachikaze) planted in plastic pots having a diameter of 5 cm were grown indoors to the third to fourth leaf stage. Wettable powder containing the compounds indicated in Table 3 were sprayed in the same manner as in Test Example 1 , and after the chemical had dried, a conidia suspension of prepared from Pyricularia oryzae which had been previously cultured in oatmeal medium was inoculated by spraying onto the plants. Following inoculation, the pots were placed in the humidified chamber of an artificial inoculation room (20°C to 23 °C), and taken out on the next day and then transferred to a greenhouse. Control effects were examined 7 days after inoculation. During the examination, the number of lesions on the rice per pot was determined in accordance with the following incidence degree indicators, and control values and theoretical values as determined according to Colby's formula were calculated in the same manner as in Test Example 1. The results are shown in Tables
3-1 to 3-3.
[0082] Indicator Incidence Degree
0 No lesions
0.5 1 to 2 lesions
3 to 5 lesions
2 6 to 10 lesions
3 1 1 to 20 lesions 4 21 to 30 lesions
5 31 to 40 lesions
6 41 or more lesions or withered
Figure imgf000062_0001
A+ Compound of 10 + 2
92 72 formula (II) (b-3)
A+ Isofetamid (b-47) 10 + 10 83 72
A+ Picarbutrazox 10 + 0.4
83 72
(b-78)
A+ Pyraziflumid 10 + 2
83 72 (b-49)
A+ Compound of 10 + 2
92 83 formula (XIV) (b-88)
A+ Compound of 10 + 2
92 83 formula (VII)- 1 (b-38)
B+ Fluxapyroxad (b-1) 10 + 2 92 72
B+ Compound of 10 + 2
92 72 formula (II) (b-3)
B+ Isofetamid (b-47) 10 + 10 92 72
B+ Picarbutrazox 10 + 0.4
83 72
(b-78)
B+ Pyraziflumid 10 + 2
83 72 (b-49)
B+ Compound of 10 + 2
100 83 formula (XIV) (b-88)
B+ Compound of 10 + 2
100 83 formula (VII)- 1 (b-38)
C+ Fluxapyroxad (b-1) 10 + 2 92 72
C+ Compound of 10 + 2
92 72 formula (II) (b-3)
C+ Isofetamid (b-47) 10 + 10 92 72
C+ Picarbutrazox 10 + 0.4
83 72
(b-78)
C+ Pyraziflumid 10 + 2
92 72 (b-49)
C+ Compound of 10 + 2
100 83 formula (XIV) (b-88)
C+ Compound of 10 + 2
100 83 formula (VII)- 1 (b-38)
Fluxapyroxad (b-1) 2 17
Compound of 2
17
formula (II) (b-3) _
Isofetamid (b-47) 10 17
Picarbutrazox 0.4
17
(b-78)
Pyraziflumid 2
17
(b-49)
Compound of 2
50
formula (XIV) (b-88)
Compound of 2
50
formula (VII)- 1 (b-38)
A 10 67
B 10 67
C 10 67
[0084] [Table 3-2]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Fluoxastrobin (b-51) 10 + 10 97 89
A+ Dimoxystrobin (b-52) 10 + 10 100 93
A+ Orysastrobin (b-53) 10 + 10 100 89
B+ Fluoxastrobin (b-51) 10 + 10 100 89
B+ Dimoxystrobin (b-52) 10 + 10 100 93
B+ Orysastrobin (b-53) 10 + 10 100 89
C+ Fluoxastrobin (b-51) 10 + 10 97 89
C+ Dimoxystrobin (b-52) 10 + 10 100 93
C+ Orysastrobin (b-53) 10 + 10 100 89
Fluoxastrobin (b-51) 10 60
Dimoxystrobin (b-52) 10 73
Orysastrobin (b-53) 10 60
A 10 73
B 10 73
C 10 73
[0085] [Table 3-3]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Tiadinil (b-45) 10 + 10 100 89
A+ Probenazole (b-73) 10 + 10 100 89
A+ Tebufloquin (b-64) 10 + 10 100 93
A+ Isoprothiolane (b-71) 10 + 50 100 87
A+ Pyroquilon (b-104) 10 + 50 100 91
A+ Pencycuron (b-76) 10 + 250 93 84
B+ Tiadinil (b-45) 10 + 10 100 89
B+ Probenazole (b-73) 10 + 10 100 89
B+ Tebufloquin (b-64) 10 + 10 100 93
B+ Isoprothiolane (b-71) 10 + 50 100 87 - -
B+ Pyroquilon (b-104) 10 + 50 97 91
B+ Pencycuron (b-76) 10 + 250 100 84
C+ Tiadinil (b-45) 10 + 10 100 89
C+ Probenazole (b-73) 10 + 10 100 89
C+ Tebufloquin (b-64) 10 + 10 100 93
C+ Isoprothiolane (b-71) 10 + 50 100 87
C+ Pyroquilon (b-104) 10 + 50 97 91
C+ Pencycuron (b-76) 10 + 250 97 84
Tiadinil (b-45) 10 60
Probenazole (b-73) 10 60
Tebufloquin (b-64) 10 73
Isoprothiolane (b-71) 50 50
Pyroquilon (b-104) 50 67
Pencycuron (b-76) 250 40
A 10 73
B 10 73
C 10 73
[0086] [Table 3-4]
Treatment
Effective ingredient Preventive Theoretical concentration
in the preparation value value
(ppm)
A+ Benzovindiflupyr (b-2) 10 + 2 100 80
A+ Bixafen (b-4) 10 + 10 97 78
A+ Picoxystrobin (b-16) 10 + 2 100 83
A+ Trifloxystrobin (b-55) 10 + 2 100 86
A+ Pyraclostrobin(b-19) 10 + 2 100 80
A+ Fluopyram (b-43) 10 + 10 100 80
A+ Prothioconazole (b-23) 10 + 10 100 78
A+ Triadimenol (b-33) 10 + 250 97 78
A+ Pyrimethanil (b-62) 10 + 50 100 78
A+ Isotianil(b-46) 10 + 10 100 83
A+ Metominostrobin (b-54) 10 + 2 100 80
A+ Acibenzolar-S -methyl
10 + 10 100 87 (b-72)
A+ Compound of
10 + 0.4 100 83 formula (XIX) (b-94)
B+ Benzovindiflupyr (b-2) 10 + 2 100 80
B+ Bixafen (b-4) 10 + 10 100 78
B+ Picoxystrobin (b-16) 10 + 2 100 83
B+ Trifloxystrobin (b-55) 10 + 2 100 86
B+ Pyraclostrobin(b-19) 10 + 2 100 80
B+ Fluopyram (b-43) 10 + 10 100 80
B+ Prothioconazole (b-23) 10 + 10 100 78
B+ Triadimenol (b-33) 10 + 250 97 78
B+ Pyrimethanil (b-62) 10 + 50 97 78
B+ Isotianil(b-46) 10 + 10 100 83 B+ Metominostrobin (b-54) 10 + 2 100 80
B+ Acibenzolar-S-methyl
10 + 10 100 87
(b-72)
B+ Compound of
10 + 0.4 100 83 formula (XIX) (b-94)
C+ Benzovindiflupyr (b-2) 10 + 2 100 80
C+ Bixafen (b-4) 10 + 10 97 78
C+ Picoxystrobin (b-16) 10 + 2 100 . 83
C+ Trifloxystrobin (b-55) 10 + 2 100 86
C+ Pyraclostrobin(b-19) 10 + 2 100 80
C+ Fluopyram (b-43) 10 + 10 97 80
C+ Prothioconazole (b-23) 10 + 10 100 78
C+ Triadimenol (b-33) 10 + 250 97 78
C+ Pyrimethanil (b-62) 10 + 50 97 78
C+ Isotianil(b-46) 10 + 10 100 83
C+ Metominostrobin (b-54) 10 + 2 100 80
C+ Acibenzolar-S-methyl
10 + 10 100 87
(b-72)
C+ Compound of
10 + 0.4 97 83 formula (XIX) (b-94)
Benzovindiflupyr (b-2) 10 + 2 40
Bixafen (b-4) 10 + 10 33
Picoxystrobin (b-16) 10 + 2 50
Trifloxystrobin (b-55) 10 + 2 57
Pyraclostrobin(b- 19) 10 + 2 40
Fluopyram (b-43) 10 + 10 40
Prothioconazole (b-23) 10 + 10 33
Triadimenol (b-33) 10 + 250 33
Pyrimethanil (b-62) 10 + 50 33
Isotianil(b-46) 10 + 10 50
Metominostrobin (b-54) 10 + 2 40
Acibenzolar-S-methyl (b-72) 10 + 10 60
Compound of
10 + 0.4 50
formula (XIX) (b-94)
A 10 67
B 10 67
C 10 67
[0087] Based on the results shown in Tables 3-1 to 3-4 above, synergistic effects were determined to be obtained when Compound A, Compound B or Compound C is used in combination with a compound of group b. Furthermore, there were no symptoms of chemical damage observed on the plant bodies or rice (variety: Sachikaze) even when Compound A, Compound B or Compound C was used in combination with a compound of group b.
[0088] Comparative Example 2 Rice Blast Preventive Test
Wettable powder prepared in compliance with Comparative Preparation - -
Example 4 containing the compounds indicated in Table 3-5 were spraied to the rice plant leaves, a conidia suspension of Pyricularia oryzae was inoculated onto the plants, and the controlling effects were examined in a manner similar to Test Example 2. The results and theoretical values as determined according to Colby's formula are shown in Table 3-5.
[0089] [Table 3-5]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Diclocymet 10 + 0.4 83 89
A+ Carpropamid 10 + 0.4 77 89
A+ Tolclofos-methyl 10 + 10 67 78
A+ Oxolinic acid 10 + 50 67 78
B+ Diclocymet 10 + 0.4 80 89
B+ Carpropamid 10 + 0.4 77 89
B+ Tolclofos-methyl 10 + 10 67 78
B+ Oxolinic acid 10 + 50 67 78
C+ Diclocymet 10 + 0.4 73 89
C+ Carpropamid 10 + 0.4 73 89
C+ Tolclofos-methyl 10 + 10 67 78
C+ Oxolinic acid 10 + 50 67 78
Diclocymet 0.4 67
Carpropamid 0.4 67
Tolclofos-methyl 10 33
Oxolinic acid 50 33
A 10 67
B 10 67
C 10 67
[0090] Based on the results shown in Tables 3-5 above, even if these compounds are used in combination with Compound A, Compound B or Compound C, the controlling effects were under their theoretical values and the action resulting from combining two types of active ingredients is indicated to be antagonistic.
[0091] Test Example 3 Barley Powdery Mildew Preventive Test
Barley plants (variety: Sekishinriki) planted in plastic pots having a diameter of 5 cm were grown indoors to the second to fourth leaf stage. Wettable powder containing the compounds indicated in Table 4 were sprayed in the same manner as in Test Example 1 , and after the chemical had dried, conidia of Blumeria graminis was inoculated onto the leaves. Following inoculation, the pots were transferred to a constant-temperature chamber (20°C to 25°C), and control effects were examined 8 days after inoculation. During the examination, the percentage of affected area exhibiting lesions on the barley plants per pot was determined in accordance with the - -
following incidence degree indicators, and control values and theoretical values as determined according to Colby's formula were calculated in the same manner as in Test Example 1. The results are shown in Table 4.
[0092] Incidence Degree Indicators
Indicator Incidence Degree
0 No lesions
0.5 Lesion area of about 1 % to 2%
1 Lesion area of less than 5%
2 Lesion area of less than 25%
3 Lesion area of less than 50%
4 Lesion area of less than 75%
5 Lesion area of 75% or more
[Table 4]
Figure imgf000067_0001
A+ Compound of 10 + 2
78 69
formula (II) (b-3)
A+ Isofetamid (b-47) 10 + 10 86 69
A+ Compound of 10 + 2
72 58
formula (XIV) (b-88)
A+ Compound of 10 + 2
97 82
formula (VII)- 1 (b-38)
B+ Fluxapyroxad (b-1) 10 + 2 67 63
B+ Benzovindiflupyr (b-2) 10 + 2 67 53
B+ Compound of 10 + 2
72 69
formula (II) (b-3)
B+ Isofetamid (b-47) 10 + 10 83 69
B+ Compound of 10 + 2
61 58
formula (XIV) (b-88)
B+ Compound of 10 + 2
89 82
formula (VII)- 1 (b-38)
C+ Fluxapyroxad (b-1) 10 + 2 86 63
C+ Benzovindiflupyr (b-2) 10 + 2 72 53
C+ Compound of 10 + 2
78 69
formula (II) (b-3)
C+ Isofetamid (b-47) 10 + 10 92 69
C+ Compound of 10 + 2
61 58
formula (XIV) (b-88)
C+ Compound of 10 + 2
83 82
formula (VII)- 1 (b-38) - -
Fluxapyroxad (b-1) 2 61
Benzovindiflupyr (b-2) 2 50
Compound of 2
67
formula (II) (b-3)
Isofetamid (b-47) 10 67
Compound of 2
56
formula (XIV) (b-88)
Compound of 2
81
formula (VII)- 1 (b-38)
10
10
10
[0094] Based on the results shown in Table 4 above, synergistic effects were determined to be obtained when Compound A, Compound B or Compound C is used in combination with a compound of group b. Furthermore, there were no symptoms of chemical damage observed on the plant bodies or barley (variety: Akashinriki) even when Compound A, Compound B or Compound C was used in combination with a compound of group b.
[0095] Test Example 4 Wheat Brown Rust Preventive Test
Wheat plants (variety: Norin 61 gou) planted in plastic pots having a diameter of 5 cm were grown indoors to the second to fourth leaf stage. Wettable powder containing the compounds indicated in Table 5 were sprayed in the same manner as in Test Example 1, and after the chemical had dried, a conidia suspension of Puccinia recondita was inoculated onto the leaves. Following inoculation, the pots were placed in the humidified chamber of an artificial inoculation room (20°C to 23 °C), removed on the following day and then transferred to a greenhouse. Control effects were examined 8 days after inoculation. During the examination, the number of lesions on five leaves of the wheat plants was determined in accordance with the following incidence degree indicators, and control values and theoretical values as determined according to Colby's formula were calculated in the same manner as in Test Example 1. The results are shown in Table 5.
[0096] Indicator Incidence Degree
0 No lesions
0.5 1 to 2 lesions
1 3 to 5 lesions
2 6 to 20 lesions
3 21 to 50 lesions
4 51 to 80 lesions
5 81 to 100 lesions - -
101 or more lesions
[0097] [Table 5]
Effective ingredient Treatment
Figure imgf000069_0001
A+ Isofetamid (b-47) 10 + 10 22 14
A+ Picarbutrazox 10 + 0.4
22 14
(b-78)
A+ Pyraziflumid 10 + 2
92 86
(b-49)
A+ Compound of 10 + 2
53 48 formula (XIV) (b-88)
A+ Compound of 10 + 2
82 73 formula (VII)- 1 (b-38)
B+ Fluxapyroxad (b-1) 10 + 2 86 74 B+ Isofetamid (b-47) 10 + 10 53 8
B+ Picarbutrazox 10 + 0.4
53 8
(b-78)
B+ Pyraziflumid 10 + 2
94 86
(b-49)
B+ Compound of 10 + 2
72 45 formula (XIV) (b-88)
B+ Compound of 10 + 2
90 71 formula (VII)- 1 (b-38)
C+ Fluxapyroxad (b-1) 10 + 2 90 75 C+ Isofetamid (b-47) 10 + 10 47 11
C+ Picarbutrazox 10 + 0.4
50 11
(b-78)
C+ Pyraziflumid 10 + 2
92 86
(b-49)
C+ Compound of 10 + 2
64 47 formula (XIV) (b-88)
C+ Compound of 10 + 2
78 72 formula (VII)- 1 (b-38)
Fluxapyroxad (b-1) 72
Isofetamid (b-47) 10 3
Picarbutrazox 0.4
(b-78)
Pyraziflumid 2
85
(b-49)
Compound of 2
42
formula (XIV) (b-88)
Compound of 2
69
formula (VII)- 1 (b-38)
A 10 1 1 B 10 6
_C 10 8
[0098] Based on the results shown in Table 5 above, synergistic effects were determined to be obtained when Compound A, Compound B or Compound C is used in combination with a compound of group b. Furthermore, there were no symptoms of chemical damage observed on the plant bodies or wheat (variety: Norin No. 61) even when Compound A, Compound B or Compound C was used in combination with a compound of group b.
[0099] Test Example 5 Tomato Late Blight Preventive Test
Tomato plants (variety: Ohgata Fukuju) planted in plastic pots having a diameter of 5 cm were grown indoors to the second to third leaf stage. Wettable powders containing the compounds indicated in Table 6 were sprayed in the same manner as in Test Example 1 , and after the chemical had dried, a zoospores and zoosporangium suspension of Phytophthora infestans was inoculated by spraying onto the plants. Following inoculation, the pots were placed in the humidified chamber of an artificial inoculation room (20°C to 22°C) and then transferred to a greenhouse on the following day followed by examining control effects 5 days after inoculation. The percentage of affected area exhibiting lesions on a single tomato leaf was determined in accordance with the same indicators as used in Test Example 1 , and control values and theoretical values as determined according to Colby's formula were calculated in the same manner as in Test Example 1. The results are shown in Tables 6-1 to 6-2.
[0100] [Table 6-1]
Effective ingredient Treatment Theoretical
Control value
in the preparation concentration (ppm) value
A+ Picarbutrazox 10 + 0.4
96 77
(b-78)
B+ Picarbutrazox 10 + 0.4
96 78
(b-78)
C+ Picarbutrazox 10 + 0.4
94 76
(b-78)
Picarbutrazox 0.4
75
(b-78)
A 10 8
B 10 13
C 10 4
[0101] [Table 6-2]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Mandipropamid (b-44) 10 + 0.08 97 78 - -
A+ Fluopicolide (b-40) 10 + 2 97 60
A+ Benalaxyl-M (b-75) 10 + 2 87 60
A+ Iprovalicarb (b-50) 10 + 2 90 67
A+ Amisulbrom (b-97) 10 + 0.08 83 67
A+ Ametoctradin (b-95) 10 + 2 87 60
A+ Zoxamide (b-39) 10 + 0.4 83 60
A+ Hymexazol (b-106) 10 + 250 73 56
B+ Mandipropamid (b-44) 10 + 0.08 93 78
B+ Fluopicolide (b-40) 10 + 2 87 60
B+ Benalaxyl-M (b-75) 10 + 2 90 60
B+ Iprovalicarb (b-50) 10 + 2 90 67
B+ Amisulbrom (b-97) 10 + 0.08 87 67
B+ Ametoctradin (b-95) 10 + 2 83 60
B+ Zoxamide (b-39) 10 + 0.4 87 60
B+ Hymexazol (b-106) 10 + 250 73 56
C+ Mandipropamid (b-44) 10 + 0.08 97 80
C+ Fluopicolide (b-40) 10 + 2 93 64
C+ Benalaxyl-M (b-75) 10 + 2 90 64
C+ Iprovalicarb (b-50) 10 + 2 90 70
C+ Amisulbrom (b-97) 10 + 0.08 90 70
C+ Ametoctradin (b-95) 10 + 2 90 64
C+ Zoxamide (b-39) 10 + 0.4 87 64
C+ Hymexazol (b-106) 10 + 250 83 60
Mandipropamid (b-44) 0.08 67
Fluopicolide (b-40) 2 40
Benalaxyl-M (b-75) 2 40
Iprovalicarb (b-50) 2 50
Amisulbrom (b-97) 0.08 50
Ametoctradin (b-95) 2 40
Zoxamide (b-39) 0.4 40
Hymexazol (b-106) 250 33
A 10 33
B 10 33
C 10 40
[0102] [Table 6-3]
Treatment
Effective ingredient Preventive Theoretical concentration
in the preparation value value
(ppm)
A+ Oxathiapiprolin (b-84) 10 + 0.0016 100 82
A+ Dithianon (b-81) 10 + 2 87 64
A+ D-tagatose (b-93) 10 + 5000 90 68
B+ Oxathiapiprolin (b-84) 10 + 0.0016 100 80
B+ Dithianon (b-81) 10 + 2 87 60
B+ D-tagatose (b-93) 10 + 5000 93 64
C+ Oxathiapiprolin (b-84) 10 + 0.0016 100 79
C+ Dithianon (b-81) 10 + 2 87 58 C+ D-tagatose (b-93) 10 + 5000 90 62
Oxathiapiprolin (b-84) 0.0016 67
Dithianon (b-81) 2 33
D-tagatose (b-93) 5000 40
A 10 47
B 10 40
C 10 37
[0103] Based on the results shown in Tables 6-1 and 6-3 above, synergistic effects were determined to be obtained when Compound A, Compound B or Compound C is used in combination with a compound of group b. Furthermore, there were no symptoms of chemical damage observed on the plant bodies or tomatoes (variety: Ohgata Fukuju) even when Compound A, Compound B or Compound C was used in combination with a compound of group b.
[0104]Test example 6 Cucumber powdery mildew preventive test
In a greenhouse, cucumber (variety: Sagamihanshiro) planted in a plastic pot having a diameter of 5 cm was grown to the 3rd to 5th-leaf stage. Spray was carried out in the same manner as in Test example 1 , and 3 days after the spray, a conidia suspension prepared from Sphaerotheca fuliginea were inoculated on the leaf surface. After inoculation, the pots were placed in a thermostatic greenhouse (20 to 25°C), and controlling effects were examined after 7 days from the inoculation. In the examination, a ratio of lesion area occupied per one leaf of cucumber was determined according to the same index as in Test example 1 , and the control value and the theoretical value according to Colby's formula were similarly calculated. The results are shown in Table 7
Figure imgf000072_0001
A+ Dimoxystrobin (b-52) 10 + 2 93 73
A+ Orysastrobin (b-53) 10 + 2 97 60
B+ Fluoxastrobin (b-51) 10 + 2 87 73
B+ Dimoxystrobin (b-52) 10 + 2 93 73
B+ Orysastrobin (b-53) 10 + 2 90 60
C+ Fluoxastrobin (b-51) 10 + 2 97 73
C+ Dimoxystrobin (b-52) 10 + 2 93 73
C+ Orysastrobin (b-53) 10 + 2 97 60
Fluoxastrobin (b-51) 2 60
Dimoxystrobin (b-52) 2 60
Orysastrobin (b-53) 2 40
A 10 33
B 10 33 - -
C 10 33
[0106] [Table 7-2]
Treatment
Effective ingredient in the Control value Theoretical value
Ull Cllll dllUll
preparation
(ppm)
A+ Carboxin (b-41) 10 + 50 87 50
A+ Thifluzamide (b-42) 10 + 50 100 78
A+ Isopyrazam (b-7) 10 + 0.4 87 50
A+ Sedaxane (b-6) 10 + 0.4 87 50
A+ Penflufen (b-5) 10 + 2 100 78
A+ Cyprodinil (b-61) 10 + 10 87 50
A+ Fenpyrazamine (b-99) 10 + 50 87 44
B+ Carboxin (b-41) 10 + 50 87 50
B+ Thifluzamide (b-42) 10 + 50 100 78
B+ Isopyrazam (b-7) 10 + 0.4 87 50
B+ Sedaxane (b-6) 10 + 0.4 87 50
B+ Penflufen (b-5) 10 + 2 100 78
B+ Cyprodinil (b-61) 10 + 10 87 50
B+ Fenpyrazamine (b-99) 10 + 50 87 44
C+ Carboxin (b-41) 10 + 50 87 50
C+ Thifluzamide (b-42) 10 + 50 100 78
C+ Isopyrazam (b-7) 10 + 0.4 93 50
C+ Sedaxane (b-6) 10 + 0.4 90 50
C+ Penflufen (b-5) 10 + 2 100 78
C+ Cyprodinil (b-61) 10 + 10 87 50
C+ Fenpyrazamine (b-99) 10 + 50 87 44
Carboxin (b-41) 50 40
Thifluzamide (b-42) 50 73
Isopyrazam (b-7) 0.4 40
Sedaxane (b-6) 0.4 40
Penflufen (b-5) 2 73
Cyprodinil (b-61) 10 40
Fenpyrazamine (b-99) 50 33
A 10 17
B 10 17
C 10 17
[0107] [Table 7-3]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Tetraconazole (b-22) 10 + 0.4 83 70
A+ Epoxiconazole (b-24) 10 + 0.4 90 64
A+ Ipconazole (b-25) 10 + 0.4 93 70
A+ Metconazole (b-26) 10 + 0.4 90 70
A+ Propiconazole (b-27) 10 + 0.4 93 64
A+ Cyproconazole (b-28) 10 + 0.4 87 64 - -
A+ Difenoconazole (b-29) 10 + 0.4 90 70
A+ Fluquinconazole (b-30) 10 + 0.4 90 70
A+ Flusilazole (b-31) 10 + 0.4 87 64
A+ Penconazole(b-32) 10 + 0.4 87 68
A+ Flutriafol (b-34) 10 + 0.4 90 64
A+ Myclobutanil (b-35) 10 + 0.4 93 68
A+ Imazalil (b-20) 10 + 0.4 90 60
A+ Prochloraz(b-21) 10 + 0.4 87 68
B+ Tetraconazole (b-22) 10 + 0.4 87 67
B+ Epoxiconazole (b-24) 10 + 0.4 83 60
B+ Ipconazole (b-25) 10 + 0.4 87 67
B+ Metconazole (b-26) 10 + 0.4 90 67
B+ Propiconazole (b-27) 10 + 0.4 87 60
B+ Cyproconazole (b-28) 10 + 0.4 83 64
B+ Difenoconazole (b-29) 10 + 0.4 87 60
B+ Fluquinconazole (b-30) 10 + 0.4 90 64
B+ Flusilazole (b-31) 10 + 0.4 87 56
B+ Penconazole(b-32) 10 + 0.4 90 64
B+ Flutriafol (b-34) 10 + 0.4 87 60
B+ Myclobutanil (b-35) 10 + 0.4 80 56
B+ Imazalil (b-20) 10 + 0.4 83 60
B+ Prochloraz(b-21) 10 + 0.4 87 67
C+ Tetraconazole (b-22) 10 + 0.4 90 67
C+ Epoxiconazole (b-24) 10 + 0.4 93 60
C+ Ipconazole (b-25) 10 + 0.4 90 67
C+ Metconazole (b-26) 10 + 0.4 90 67
C+ Propiconazole (b-27) 10 + 0.4 90 60
C+ Cyproconazole (b-28) 10 + 0.4 87 64
C+ Difenoconazole (b-29) 10 + 0.4 90 60
C+ Fluquinconazole (b-30) 10 + 0.4 87 64
C+ Flusilazole (b-31) 10 + 0.4 90 56
C+ Penconazole(b-32) 10 + 0.4 87 64
C+ Flutriafol (b-34) 10 + 0.4 83 60
C+ Myclobutanil (b-35) 10 + 0.4 87 56
C+ Imazalil (b-20) 10 + 0.4 90 60
C+ Prochloraz(b-21) 10 + 0.4 87 67
Tetraconazole (b-22) 0.4 50
Epoxiconazole (b-24) 0.4 40
Ipconazole (b-25) 0.4 50
Metconazole (b-26) 0.4 50
Propiconazole (b-27) 0.4 40
Cyproconazole (b-28) 0.4 47
Difenoconazole (b-29) 0.4 40
Fluquinconazole (b-30) 0.4 47
Flusilazole (b-31) 0.4 33
Penconazole(b-32) 0.4 47
Flutriafol (b-34) 0.4 40 - -
Myclobutanil (b-35) 0.4 33
Imazalil (b-20) 0.4 40
Prochloraz(b-21) 0.4 50
A 10 40
B 10 33
C 10 33
[0108] [Table 7-4]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Thiabendazole (b-60) 10 + 10 90 64
A+ Benomyl (b-58) 10 + 10 97 70
A+ Thiuram (b-68) 10 + 50 87 60
A+ Metiram (b-67) 10 + 50 87 60
A+ Folpet (b-70) 10 + 50 80 60
A+ Pyrisoxazole (b-103) 10 + 50 90 60
B+ Thiabendazole (b-60) 10 + 10 97 64
B+ Benomyl (b-58) 10 + 10 93 70
B+ Thiuram (b-68) 10 + 50 80 60
B+ Metiram (b-67) 10 + 50 80 60
B+ Folpet (b-70) 10 + 50 77 60
B+ Pyrisoxazole (b-103) 10 + 50 97 60
C+ Thiabendazole (b-60) 10 + 10 97 64
C+ Benomyl (b-58) 10 + 10 97 70
C+ Thiuram (b-68) 10 + 50 83 60
C+ Metiram (b-67) 10 + 50 80 60
C+ Folpet (b-70) 10 + 50 80 60
C+ Pyrisoxazole (b-103) 10 + 50 90 60
Thiabendazole (b-60) 10 40
Benomyl (b-58) 10 50
Thiuram (b-68) 50 33
Metiram (b-67) 50 33
Folpet (b-70) 50 33
Pyrisoxazole (b-103) 50 33
A 10 40
B 10 40
C 10 40
[0109] [Table 7-5]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Fenpropimorph (b-65) 10 + 0.4 80 60
A+ Tridemorph (b-66) 10 + 0.4 80 60
A+ Metrafenone (b-82) 10 + 0.08 83 64
A+ Quinoxyfen (b-63) 10 + 0.016 97 76
A+ Flutianil (b-77) 10 + 0.016 97 80 A+ Proquinazid (b-100) 10 + 0.016 97 64
A+ Spiroxamine (b-101) 10 + 0.4 83 60
A+ Fenpropidin (b-102) 10 + 0.4 97 64
A+ Sulfur (b-96) 10 + 10 100 84
A+ Chinomethionat (b-74) 10 + 0.4 83 70
B+ Fenpropimorph (b-65) 10 + 0.4 80 60
B+ Tridemorph (b-66) 10 + 0.4 80 60
B+ Metrafenone (b-82) 10 + 0.08 83 64
B+ Quinoxyfen (b-63) 10 + 0.016 83 76
B+ Flutianil (b-77) 10 + 0.016 97 80
B+ Proquinazid (b-100) 10 + 0.016 97 64
B+ Spiroxamine (b-101) 10 + 0.4 87 60
B+ Fenpropidin (b-102) 10 + 0.4 80 64
B+ Sulfur (b-96) 10 + 10 97 84
B+ Chinomethionat (b-74) 10 + 0.4 83 70
C+ Fenpropimorph (b-65) 10 + 0.4 83 60
C+ Tridemorph (b-66) 10 + 0.4 83 60
C+ Metrafenone (b-82) 10 + 0.08 93 64
C+ Quinoxyfen (b-63) 10 + 0.016 97 76
C+ Flutianil (b-77) 10 + 0.016 97 80
C+ Proquinazid (b-100) 10 + 0.016 97 64
C+ Spiroxamine (b-101) 10 + 0.4 87 60
C+ Fenpropidin (b-102) 10 + 0.4 80 64
C+ Sulfur (b-96) 10 + 10 97 84
C+ Chinomethionat (b-74) 10 + 0.4 80 70
Fenpropimo h (b-65) 0.4 33
Tridemorph (b-66) 0.4 33
Metrafenone (b-82) 0.08 40
Quinoxyfen (b-63) 0.016 60
Flutianil (b-77) 0.016 67
Proquinazid (b-100) 0.016 40
Spiroxamine (b-101) 0.4 33
Fenpropidin (b-102) 0.4 40
Sulfur (b-96) 10 73
Chinomethionat (b-74) 0.4 50
A 10 40
B 10 40
C 10 40
[01 10] [Table 7-6]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Tiadinil (b-45) 10 + 10 87 64
A+ Probenazole (b-73) 10 + 10 93 64
A+ Tebufloquin (b-64) 10 + 10 90 80
A+ Isoprothiolane (b-71) 10 + 10 83 64 - -
A+ Pyroquilon (b-104) 10 + 50 83 44
A+ Pencycuron (b-76) 10 + 250 80 60
B+ Tiadinil (b-45) 10 + 10 83 64
B+ Probenazole (b-73) 10 + 10 87 64
B+ Tebufloquin (b-64) 10 + 10 93 80
B+ Isoprothiolane (b-71) 10 + 10 80 64
B+ Pyroquilon (b-104) 10 + 50 80 44
B+ Pencycuron (b-76) 10 + 250 80 60
C+ Tiadinil (b-45) 10 + 10 93 64
C+ Probenazole (b-73) 10 + 10 90 64
C+ Tebufloquin (b-64) 10 + 10 87 80
C+ Isoprothiolane (b-71) 10 + 10 80 64
C+ Pyroquilon (b-104) 10 + 50 80 44
C+ Pencycuron (b-76) 10 + 250 77 60
Tiadinil (b-45) 10 40
Probenazole (b-73) 10 40
Tebufloquin (b-64) 10 67
Isoprothiolane (b-71) 10 40
Pyroquilon (b-104) 50 7
Pencycuron (b-76) 250 33
A 10 40
B 10 40
C 10 40
[0111] [Table 7-7]
Treatment
Effective ingredient Preventive Theoretical concentration
in the preparation value value
(ppm)
A+ Pyriofenone (b-83) 10 + 0.08 93 64
A+Compound of
10 + 2 93 64 formula (XV)- 1 (b-89)
A+ Oxathiapiprolin (b-84) 10 + 50 87 50
A+ Compound of
10 + 10 93 70 formula (XIX) (b-94)
A+ Compound of
10 + 0.08 97 64 formula (XVII) (b-91)
A+ Compound of
10 + 0.4 97 76 formula (III) (b-8)
A+ Compound of
10 + 0.4 97 76 formula (IV) (b-9)
A+ Isotianil(b-46) 10 + 2 90 60
A+ Acibenzolar-S-methyl (b-72) 10 + 2 90 60
B+ Pyriofenone (b-83) 10 + 0.08 93 64
B+Compound of
10 + 2 93 64 formula (XV)- 1 (b-89)
B+ Oxathiapiprolin (b-84) 10 + 50 87 50
B+ Compound of 10 + 10 93 70 - /o -
formula (XIX) (b-94)
B+ Compound of
10 + 0.08 97 64 formula (XVII) (b-91)
B+ Compound of
10 + 0.4 100 76 formula (III) (b-8)
B+ Compound of
10 + 0.4 97
formula (IV) (b-9) 76
B+ Isotianil(b-46) 10 + 2 93 60
B+ Acibenzolar-S-methyl (b-72) 10 + 2 93 60
C+ Pyriofenone (b-83) 10 + 0.08 93 64
C+Compound of
10 + 2 90
formula (XV)- 1 (b-89) 64
C+ Oxathiapiprolin (b-84) 10 + 50 87 50
C+ Compound of
10 + 10 93 70 formula (XIX) (b-94)
C+ Compound of
10 + 0.08 97 64 formula (XVII) (b-91)
C+ Compound of
10 + 0.4 97 76 formula (III) (b-8)
C+ Compound of
10 + 0.4 97
formula (IV) (b-9) 76
C+ Isotianil(b-46) 10 + 2 90 60
C+ Acibenzolar-S-methyl (b-72) 10 + 2 90 60
Pyriofenone (b-83) 0.08 40
Compound of
40
formula (XV)- 1 (b-89)
Oxathiapiprolin (b-84) 50 17
Compound of
10 50
formula (XIX) (b-94)
Compound of
0.08 40
formula (XVII) (b-91)
Compound of
0.4 60
formula (III) (b-8)
Compound of
0.4 60
formula (IV) (b-9)
A+ Isotianil(b-46) 2 33
A+ Acibenzolar-S-methyl (b-72) 2 33
A 10 40
B 10 40
C 10 40
[0112] [Table 7-8]
Treatment
Effective ingredient Preventive Theoretical concentration
in the preparation value value
(ppm)
A+ Phosphorous acid (b-105) 10 + 50 93 60 A+ Propineb (b-69) 10 + 50 97 50 A+ (b-36) 10 + 0.4 90 60
A+ (b-88) 10 + 0.4 93 64
A+ Compound of
10 + 10 97 70
(XI)- 1 (b-85)
A+ Compound of
10 + 10 93 70
(XI)-2 (b-85)
A+ Compound of
10 + 0.4 90 64
(XVIII) (b-92)
A+ D-tagatose (b-93) 10 + 5000 93 60
B+ Phosphorous acid (b-105) 10 + 50 90 60
B+ Propineb (b-69) 10 + 50 97 50
B+ (b-36) 10 + 0.4 93 60
B+ (b-88) 10 + 0.4 93 64
B+ Compound of
10 + 10 93 70
(XI)- 1 (b-85)
B+ Compound of
10 + 10 97 70
(XI)-2 (b-85)
B+ Compound of
10 + 0.4 97 64
(XVIII) (b-92)
B+ D-tagatose (b-93) 10 + 5000 93 60
C+ Phosphorous acid (b-105) 10 + 50 90 60
C+ Propineb (b-69) 10 + 50 97 50
C+ (b-36) 10 + 0.4 93 60
C+ (b-88) 10 + 0.4 97 64
C+ Compound of
10 + 10 90 70
(XI)- 1 (b-85)
C+ Compound of
10 + 10 90 70
(XI)-2 (b-85)
C+ Compound of
10 + 0.4 93 64
(XVIII) (b-92)
C+ D-tagatose (b-93) 10 + 5000 93 60
Phosphorous acid (b-105) 50 33
Propineb (b-69) 50 17
Compound of
0.4 33
(V) (b-36)
Compound of
0.4 40
(XIV) (b-88)
Compound of
10 50
(XI)- 1 (b-85)
Compound of
10 50
(XI)-2 (b-85)
Compound of
0.4 40
(XVIII) (b-92)
D-tagatose (b-93) 5000 33
A 10 40
B 10 40
C 10 40 - -
[0113] From the results shown in the above-mentioned Table 7-1 to 7-8, it could be understood that synergistic effects could be obtained when Compound A, B or C and the compound of Group b are used in combination. Incidentally, even when
Compound A, B or C and the compound of Group b are used in combination, no chemical damage symptom was admitted in the plant material, cucumber (variety: Sagamihanpaku).
[0114] Comparative example 3 Cucumber powdery mildew preventive test
Wettable powder prepared in compliance with Comparative Preparation Example 4 containing the compounds indicated in Table 7-9 were spraied to the cucumber leaves, a conidiospore suspension prepared from Sphaerotheca fuliginea was inoculated onto the plants, and the controlling effects were examined in a manner similar to Test Example 6. The results and theoretical values as determined according to Colby's formula are shown in Table 7-9.
[0115] [Table 7-9]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Diclocymet 10 + 50 50 60
A+ Carpropamid 10 + 50 47 64
A+ Tolclofos-methyl 10 + 50 40 60
A+ Oxolinic acid 10 + 50 40 60
B+ Diclocymet 10 + 50 40 60
B+ Carpropamid 10 + 50 40 64
B+ Tolclofos-methyl 10 + 50 40 60
B+ Oxolinic acid 10 + 50 40 60
C+ Diclocymet 10 + 50 40 60
C+ Carpropamid 10 + 50 40 64
C+ Tolclofos-methyl) 10 + 50 33 60
C+ Oxolinic acid 10 + 50 33 60
Diclocymet 50 40
Carpropamid 50 33
Tolclofos-methyl 50 33
Oxolinic acid 50 33
A 10 40
B 10 40
C 10 40
[0116] Based on the results shown in Tables 7-9 above, even if these compounds are used in combination with Compound A, Compound B or Compound C, the controlling effects were under their theoretical values and the action resulting from combining two types of active ingredients is indicated to be antagonistic. [0117] Test example 7 Cucumber downy mildew preventive test
In a greenhouse, cucumber (variety: Sagamihanshiro) planted in a plastic pot having a diameter of 5 cm was grown to the 3rd to 5th-leaf stage. Spray was carried out in the same manner as in Test example 1 , and after drying the chemical liquid, the pots were transferred into a greenhouse. After 3 days from the spray, a zoosporangium suspension of Pseudoperonospora cubensis was inoculated. After inoculation, the pots were placed in a high-humidity chamber (20 to 25 °C), transferred into a greenhouse on the next day, and controlling effects were examined after 7 days from the inoculation. A ratio of lesion area occupied per one leaf of cucumber was determined according to the same index as in Test example 1, and the control value and the theoretical value according to Colby's formula were similarly calculated. The results are shown in
Tables 8.
[0118] [Table 8]
Effective ingredient Treatment Preventive Theoretical in the preparation concentration value value
(ppm)
A+ Mandipropamid (b-44) 10 + 0.08 100 76
A+ Fluopicolide (b-40) 10 + 2 97 76
A+ Benalaxyl-M (b-75) 10 + 2 100 76
A+ Iprovalicarb (b-50) 10 + 2 93 63
A+ Amisulbrom (b-97) 10 + 0.08 93 76
A+ Ametoctradin (b-95) 10 + 2 93 63
A+ Zoxamide (b-39) 10 + 0.4 93 51
A+ Hymexazol (b-106) 10 + 250 93 39
B+ Mandipropamid (b-44) 10 + 0.08 97 74
B+ Fluopicolide (b-40) 10 + 2 93 74
B+ Benalaxyl-M (b-75) 10 + 2 97 74
B+ Iprovalicarb (b-50) 10 + 2 93 62
B+ Amisulbrom (b-97) 10 + 0.08 93 74
B+ Ametoctradin (b-95) 10 + 2 97 62
B+ Zoxamide (b-39) 10 + 0.4 93 49
B+ Hymexazol (b-106) 10 + 250 93 36
C+ Mandipropamid (b-44) 10 + 0.08 93 72
C+ Fluopicolide (b-40) 10 + 2 90 72
C+ Benalaxyl-M (b-75) 10 + 2 90 72
C+ Iprovalicarb (b-50) 10 + 2 93 58
C+ Amisulbrom (b-97) 10 + 0.08 97 72
C+ Ametoctradin (b-95) 10 + 2 97 58
C+ Zoxamide (b-39) 10 + 0.4 97 44
C+ Hymexazol (b-106) 10 + 250 87 31
Mandipropamid (b-44) 0.08 67
Fluopicolide (b-40) 2 67
Benalaxyl-M (b-75) 2 67 - -
Iprovalicarb (b-50) 2 50
Amisulbrom (b-97) 0.08 67
Ametoctradin (b-95) 2 50
Zoxamide (b-39) 0.4 33
Hymexazol (b-106) 250 17
A 10 27
B 10 23
C 10 17
[01 19] From the results of the above-mentioned Tables 8, it could be understood that synergistic effects could be obtained when Compound A, B or C and the compound of Group b are used in combination. Incidentally, even when Compound A, B or C and the compound of Group b are used in combination, no chemical damage symptom was admitted in the plant material, cucumber (variety: Sagamihanpaku).
INDUSTRIAL APPLICABILITY
[0120] The plant disease control composition of the present invention is used as a superior plant disease control agent since it has a plurality of disease spectra against various plant pathogens, including fungicide-resistant organisms (such as Pyricularia oryzae that causes rice blast or Botrytis cinerea that causes gray mold in tomatoes, cucumbers and green beans), exhibits superior control effects (synergistic control effects) that cannot be predicted from the individual components alone, demonstrates a high level of plant disease control effects even against organisms resistant to existing chemical agents, and is observed to be free of the occurrence of phytotoxicity.

Claims

1. A plant disease control composition comprising as active ingredients thereof:
(a) at least one quinoline compound represented by general formula (I) or a salt thereof (group a):
Figure imgf000083_0001
wherein R1 and R2 may be the same or different and represent a methyl group, ethyl group, propyl group, trifluoromethyl group, trifluoroethyl group, phenyl group, fluorophenyl group or chlorophenyl group,
R3 and R4 may be the same or different and represent a hydrogen atom, fluorine atom or methyl group,
X represents a fluorine atom, chlorine atom, bromine atom, methyl group, ethynyl group, furyl group, thienyl group, cyano group, methoxyethanimidoyl group, ethoxyethanimidoyl group or phenoxyethanimidoyl group and n is 0, 1 or 2, and
Y represents a fluorine atom or methyl group and m is 0 or 1 ; and
(b) one or more fungicidal compounds selected from the following (b-1) to (b-106) (group b):
pyrazole carboxamides consisting of
(b-1) Fluxapyroxad,
(b-2) Benzovindiflupyr,
-3) a compound of formula (II)
Figure imgf000083_0002
(b-4) Bixafen,
(b-5) Penflufen,
(b-6) Sedaxane,
(b-7) Isopyrazam,
(b-8) a compound of formula (III)
Figure imgf000084_0001
(III), and -9) a compound of formula (IV)
Figure imgf000084_0002
methoxyacrylates consisting of
(b-10) Enoxastrobin,
(b-11) Pyraoxystrobin,
(b-12) Coumoxystrobin,
(b-13) Coumethoxystrobin,
(b-14) Flufenoxystrobin,
(b-15) Pyriminostrobin, and
(b-16) Picoxystrobin;
methoxycarbamates consisting of
(b-17) Pyramethostrobin,
(b-18) Triclopyricarb, and
(b-19) Pyraclostrobin;
azole compounds consisting of
(b-20) Imazalil,
(b-21) Prochloraz,
(b-22) Tetraconazole,
(b-23) Prothioconazole,
(b-24) Epoxiconazole,
(b-25) Ipconazole,
(b-26) Metconazole,
(b-27) Propiconazole,
(b-28) Cyproconazole,
(b-29) Difenoconazole,
(b-30) Fluquinconazole,
(b-31) Flusilazole, (b-32) Penconazole,
(b-33) Triadimenol,
(b-34) Flutriafol,
(b-35) Myclobutanil,
(b-36) compounds of general formula (V)
Figure imgf000085_0001
wherein Rb7 represents a hydrogen atom, alkyl group, allyl group, benzyl group, cyano group or a valency that forms a double bond between a sulfur atom and a triazole ring to generate a ring represented by:
Figure imgf000085_0002
and
Rb8 represents a hydrogen atom or fluorine atom,
(b-37) compounds of general formula (VI)
Figure imgf000085_0003
wherein the broken line indicates the presence or absence of a bond, and Rb9 represents a hydrogen atom, alkyl group, allyl group, benzyl group or cyano group, and (b-38) com ounds of general formula (VII)
Figure imgf000085_0004
wherein Rb10 represents a halogen atom and Rbn represents a nitrogen atom or methine group; amide compounds consisting of
(b-39) Zoxamide,
(b-40) Fluopicolide,
(b-41) Carboxin,
(b-42) Thifluzamide,
(b-43) Fluopyram,
(b-44) Mandipropamid,
(b-45) Tiadinil,
(b-46) Isotianil,
(b-47) Isofetamid,
(b-48) Valifenalate,
-49) Pyraziflumid,
Figure imgf000086_0001
(b-50) Iprovalicarb;
strobilurin compounds consisting of
(b-51) Fluoxastrobin,
(b-52) Dimoxystrobin,
(b-53) Orysastrobin,
(b-54) Metominostrobin,
(b-55) Trifloxystrobin,
(b-56) Mandestrobin, and
(b-57) Fenaminostrobin;
benzimidazole compounds consisting of
(b-58) Benomyl,
(b-59) Carbendazim, and
(b-60) Thiabendazole;
pyrimidine compounds consisting of
(b-61) Cyprodinil, and
(b-62) Pyrimethanil;
quinolone compounds consisting of
(b-63) Quinoxyfen, and (b-64) Tebufioquin;
morpholine compounds consisting of
(b-65) Fenpropimorph, and
(b-66) Tridemorph;
organosulfur compounds consisting of
(b-67) Metiram,
(b-68)Thiuram,
(b-69) Propineb,
(b-70) Folpet,
(b-71) Isoprothiolane,
(b-72) Acibenzolar-S-methyl,
(b-73) Probenazole, and
(b-74) Chinomethionat;
anilide compounds consisting of
(b-75) Benalaxyl-M,
(b-76) Pencycuron, and
(b-77) Flutianil;
aminopyridine compounds consisting of
(b-78) Picarbutrazox, and
II)
Figure imgf000087_0001
(VIII) wherein Rbi2 represents
Figure imgf000087_0002
dithiine compounds consisting of
-80)
Figure imgf000087_0003
(IX) (X) and
(b-81) Dithianon; phenylketone compounds consisting of
(b-82) Metrafenone, and
(b-83) Pyriofenone;
other fungicidal compounds (i) consisting of
(b-84) Oxathiapiprolin,
(b-85) compounds of general formula (XI)
Figure imgf000088_0001
wherein Rbi represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group, Rb2 represents a fluorine atom or hydrogen atom, Rb3 represents a halogen atom, Rb4 represents a halogen atom, methoxy group or hydrogen atom and Z represents N or C-F,
(b-86) compounds of general formula (XII)
Figure imgf000088_0002
wherein Rb5 represents a methyl group or fluorine atom,
(b-87) compounds of general formula (XIII)
Figure imgf000088_0003
(XIII)
wherein Rb6 represents -CH2OC(0)CH(CH3)2, -C(0)CH3, -CH2OC(0)CH3, -C(0)
Figure imgf000088_0004
(b-88) a compound of formula (XIV)
Figure imgf000089_0001
(b-89) compounds of general formula (XV)
Figure imgf000089_0002
wherein Rb13 represents a chlorine atom or fluorine atom, Rb14 represents a chlorine atom or hydrogen atom and Rbis represents a chlorine atom or bromine atom,
I)
Figure imgf000089_0003
wherein Rb16 represents a fluorine atom or methyl other fungicidal compounds (ii) consisting of
b-91) a compound of formula (XVII)
Figure imgf000089_0004
(b-92) a compound of formula (XVIII)
Figure imgf000090_0001
(b-93) D-tagatose,
(b-94) compounds of general formula (XIX)
Figure imgf000090_0002
(XIX)
wherein Rb17 represents a hydrogen atom or fluorine atom;
other fungicidal compounds (iii) consisting of
(b-95) Ametoctradin,
(b-96) Sulfur;
(b-97) Amisulbrom,
(b-98) Pyribencarb,
(b-99) Fenpyrazamine,
(b-100) Proquinazid,
(b-101) Spiroxamine,
(b-102) Fenpropidin,
(b-103) Pyrisoxazole,
(b-104) Pyroquilon,
(b-105) Phosphorous acid, and
(b-106) Hydroxyisoxazole (Hymexazol).
2. The plant disease control composition according to claim 1, wherein the fungicidal compound of group b is selected from:
pyrazole carboxamides consisting of
(b-1) Fluxapyroxad,
(b-2) Benzovindiflupyr,
(b-3) a compound of formula (II)
Figure imgf000091_0001
(b-4) Bixafen,
(b-5) Penflufen,
(b-6) Sedaxane,
(b-7) Isopyrazam,
b-8) a compound of formula (III)
Figure imgf000091_0002
(b-9) a compound of formula (IV)
Figure imgf000091_0003
methoxyacrylates consisting of
(b-16) Picoxystrobin;
methoxycarbamates consisting of
(b-19) Pyraclostrobin;
azole compounds consisting of
(b-20) Imazalil,
(b-21) Prochloraz,
(b-22) Tetraconazole,
(b-23) Prothioconazole,
(b-24) Epoxiconazole,
(b-25) Ipconazole,
(b-26) Metconazole,
(b-27) Propiconazole,
(b-28) Cyproconazole,
(b-29) Difenoconazole, (b-30) Fluquinconazole,
(b-31) Flusilazole,
(b-32) Penconazole,
(b-33) Triadimenol,
(b-34) Flutriafol,
(b-35) Myclobutanil,
(b-36) com ounds of general formula (V)
Figure imgf000092_0001
wherein Rb7 represents a hydrogen atom, alkyl group, allyl group, benzyl group, cyano group or a valency that forms a double bond between a sulfur atom and a triazole ring to generate a ring represented by:
Figure imgf000092_0002
Rb8 represents a hydrogen atom or fluorine atom, and
b-38) compounds of general formula (VII)
Figure imgf000092_0003
wherein Rb10 represents a halogen atom and Rbn represents a nitrogen atom or me thine group;
amide compounds consisting of
(b-39) Zoxamide,
(b-40) Fluopicolide,
(b-41) Carboxin,
(b-42) Thifluzamide,
(b-43) Fluopyram,
(b-44) Mandipropamid,
(b-45) Tiadinil, (b-46) Isotianil,
(b-47) Isofetamid,
(b-49) Pyraziflumid,
Figure imgf000093_0001
' and
(b-50) Iprovalicarb;
strobilurin compounds consisting of
(b-51) Fluoxastrobin,
(b-52) Dimoxystrobin,
(b-53) Orysastrobin,
(b-54) Metominostrobin, and
(b-55) Trifloxystrobin;
benzimidazole compounds consisting of
(b-58) Benomyl,
(b-59) Carbendazim, and
(b-60) Thiabendazole;
pyrimidine compounds consisting of
(b-61) Cyprodinil, and
(b-62) Pyrimethanil;
quinolone compounds consisting of
(b-63) Quinoxyfen, and
(b-64) Tebufloquin;
morpholine compounds consisting of
(b-65) Fenpropimorph, and
(b-66) Tridemorph;
organosulfur compounds consisting of
(b-67) Metiram,
(b-68) Thiuram,
(b-69) Propineb,
(b-70) Folpet,
(b-71) Isoprothiolane,
(b-72) Acibenzolar-S-methyl, (b-73) Probenazole, and
(b-74) Chinomethionat;
anilide compounds consisting of
(b-75) Benalaxyl-M,
(b-76) Pencycuron, and
(b-77) Flutianil;
an aminopyridine compound consisting of
(b-78) Picarbutrazox;
a dithiine compound consisting of
(b-81) Dithianon;
phenylketone compounds consisting of
(b-82) Metrafenone, and
(b-83) Pyriofenone;
other fungicidal compounds (i) consisting of
(b-84) Oxathiapiprolin
(b-85) compounds of general formula (XI)
Figure imgf000094_0001
wherein Rbi represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group, Rb represents a fluorine atom or hydrogen atom, Rb3 represents a halogen atom, Rb4 represents a halogen atom, methoxy group or hydrogen atom and Z represents N or C-F,
b-88) a compound of formula (XIV)
Figure imgf000094_0002
(b-89) compounds of general formula (XV)
Figure imgf000095_0001
wherein Rbi3 represents a chlorine atom or fluorine atom, Rbi4 represents a chlorine atom or hydrogen atom and Rbis represents a chlorine atom or bromine atom, other fungicidal compounds (ii) consisting of:
b-91) a compound of formula (XVII)
Figure imgf000095_0002
(b-93) D-tagatose, and
(b-94) compounds of general formula (XIX)
Figure imgf000095_0003
(XIX)
wherein Rbn represents a hydrogen atom or fluorine atom; other fungicidal compounds (iii) consisting of:
(b-95) Ametoctradin,
(b-96) Sulfur;
(b-97) Amisulbrom, (b-98) Pyribencarb,
(b-99) Fenpyrazamine,
(b-100) Proquinazid,
(b- 101) Spiroxamine,
(b-102) Fenpropidin,
(b-103) Pyrisoxazole,
(b-104) Pyroquilon,
(b-105) Phosphorous acid, and
(b-106) Hydroxyisoxazole (Hymexazol).
3. The plant disease control composition according to claim 1, wherein the fungicidal compound of group b is selected from:
pyrazole carboxamides consisting of
(b-1) Fluxapyroxad,
(b-2) Benzovindiflupyr,
-3) a compound of formula (II)
Figure imgf000096_0001
-8) a compound of formula (III)
Figure imgf000096_0002
(III), and
(b-9) a compound of formula (IV)
Figure imgf000096_0003
azole compounds consisting of
(b-36) compounds of general formula (V)
Figure imgf000097_0001
wherein Rb7 represents a hydrogen atom, alkyl group, allyl group, benzyl group, cyano group or a valency that forms a double bond between a sulfur atom and a triazole ring to generate a ring represented by:
Figure imgf000097_0002
Rb¾ represents a hydrogen atom or fluorine atom, and
b-38) compounds of general formula (VII)
Figure imgf000097_0003
wherein Rb10 represents a halogen atom and Rbi j represents a nitrogen atom or methine group;
amide compounds consisting of
(b-47) Isofetamid, and
(b-49) Pyraziflumid,
Figure imgf000097_0004
' and
an aminopyridine compound consisting of
(b-78) Picarbutrazox;
other fungicidal compounds (i) consisting of
(b-84) Oxathiapiprolin
(b-85) compounds of general formula (XI)
Figure imgf000098_0001
wherein Rbt represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group, Rb2 represents a fluorine atom or hydrogen atom, Rb3 represents a halogen atom, Rb4 represents a halogen atom, methoxy group or hydrogen atom and Z represents N or C-F,
b-88) a compound of formula (XIV)
Figure imgf000098_0002
(b-89) compounds of general formula (XV)
Figure imgf000098_0003
wherein Rb13 represents a chlorine atom or fluorine atom,
Rbi4 represents a chlorine atom or hydrogen atom and
Rbis represents a chlorine atom or bromine atom;
other fungicidal compounds (ii) consisting of
(b-91) a compound of formula (XVII)
Figure imgf000098_0004
(b-92) a compound of formula (XVIII)
Figure imgf000099_0001
(b-93) D-tagatose,
(b-94) compounds of general formula (XIX)
Figure imgf000099_0002
(XIX)
wherein Rb17 represents a hydrogen atom or fluorine atom.
4. The plant disease control composition according to claim 1, wherein the fungicidal compound of group b is selected from:
pyrazole carboxamides consisting of
(b-1) Fluxapyroxad,
(b-2) Benzovindiflupyr, and
b-3)
Figure imgf000099_0003
methoxyacrylates consisting of
(b-1.0) Enoxastrobin,
(b-11) Pyraoxystrobin,
(b-12) Coumoxystrobin,
(b-13) Coumethoxystrobin,
(b-14) Flufenoxystrobin, and
(b-15) Pyriminostrobin;
methoxycarbamates consisting of
(b-17) Pyrametostrobin, and
(b-18) Triclopyricarb;
(b-84) Oxathiapiprolin; (b-56) Mandestrobin;
(b-47) Isofetamid;
(b-78) Picarbutrazox;
(b-57) Fenaminostrobin;
(b-48) Valifenalate;
(b-49) Pyraziflumid
Figure imgf000100_0001
Figure imgf000100_0002
wherein Rbi represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group, Rb2 represents a fluorine atom or hydrogen atom, Rb3 represents a halogen atom, Rb4 represents a halogen atom, methoxy group or hydrogen atom,
Figure imgf000100_0003
wherein Rb5 represents a methyl group or fluorine atom,
Figure imgf000100_0004
wherein Rb6 represents -CH2OC(0)CH(CH3)2, -C(0)CH3, -CH2OC(0)CH3,
Figure imgf000101_0001
Figure imgf000102_0001
wherein Rb represents a hydrogen atom, alkyl group, amino group or cyano group, and Rb8 represents a hydrogen atom or fluorine atom;
(b-37')
Figure imgf000102_0002
wherein the broken line indicates the presence or absence of a bond, and Rb9 represents a hydrogen atom, alkyl group, amino group or cyano group;
Figure imgf000102_0003
wherein Rb]0 represents a halogen atom and Rb] i represents a nitrogen atom or methine group; and
(b-79)
Figure imgf000102_0004
wherein Rbi2 represents
Figure imgf000102_0005
5. The plant disease control composition according to claim 1, wherein the fungicidal compound of group b is selected from:
pyrazole carboxamides consisting of
(b-1) Fluxapyroxad,
(b-2) Benzovindiflupyr, and
-3) a compound of formula (II)
Figure imgf000103_0001
(b-47) Isofetamid;
(b-78) Picarbutrazox;
-49) Pyraziflumid,
Figure imgf000103_0002
(b-85) compounds of general formula (XI)
Figure imgf000103_0003
wherein Rbi represents a chlorine atom, bromine atom, cyano group, methyl group or methoxy group, Rb2 represents a fluorine atom or hydrogen atom, Rb3 represents a halogen atom, and Rb4 represents a halogen atom, methoxy group or hydrogen atom;
(b-88) a compound of formula (XIV)
Figure imgf000104_0001
(b-89) a compound of formula (XV)- 1
Figure imgf000104_0002
(b-36) com ounds of general formula (V)
Figure imgf000104_0003
wherein Rb7 represents a hydrogen atom, alkyl group, amino group or cyano group, and Rb8 represents a hydrogen atom or fluorine atom;
(b-37') compounds of general formula (VI)
Figure imgf000104_0004
wherein the broken line indicates the presence or absence of a bond, and Rb9 represents a hydrogen atom, alkyl group, amino group or cyano group;
(b-38) compounds of general formula (VII)
Figure imgf000105_0001
wherein Rb10 represents a halogen atom and Rbn represents a nitrogen atom or methine group; and
(b-79) compounds of general formula (VIII)
Figure imgf000105_0002
wherein Rbi2 represents
Figure imgf000105_0003
6. The plant disease control composition according to any of claims 1 to 3, wherein the fungicidal compound of group b is selected from:
pyrazole carboxamides consisting of
(b-1) Fluxapyroxad,
(b-2) Benzovindiflupyr, and
-3) a compound of formula (II)
Figure imgf000105_0004
(b-47) Isofetamid;
(b-78) Picarbutrazox;
(b-49) Pyraziflumid
Figure imgf000106_0001
b-88) a compound of formula (XIV)
Figure imgf000106_0002
-38) compounds of general formula (VII)
Figure imgf000106_0003
wherein Rbio represents a halogen atom and Rbn represents a nitrogen atom or methine group.
7. The plant disease control composition according to claim 1, wherein the quinoline compound (I) of group a is:
(a- 1 ) 3 -(5-fluoro-3 ,3 -dimethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline,
(a-2) 3-(5-chloro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, (a-3) 3-(5-bromo-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, (a-4) 3-(5-ethynyl-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, (a-5) 3 -(5 ,6-difluoro-3 ,3 -dimethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline (a-6) 3-(3-ethyl-5-fluoro-3-propyl-3,4-dihydroisoquinolin-l-yl)quinoline (a-7) 3-(5-fluoro-3-methyl-3-propyl-3,4-dihydroisoquinolin-l-yl)quinoline (a-8) 3-(3-methyl-3-trifluoromethyl-3,4-dihydroisoquinolin-l-yl)quinoline (a-9) 3-[3-methyl-3-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-l-yl] quinoline
(a- 10) 3 - [3 -methyl-3 -phenyl-3 ,4-dihydroisoquinolin- 1 -yl] quinoline
(a-1 1) 3-[3-methyl-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-l -yljquinoline
(a-12) 3 -[3 -methyl-3 -(4-chlorophenyl)-3,4-dihydroisoquinolin-l -yl]quinoline (a- 13) 3 -(3 ,3 ,4,4-tetramethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline
(a- 14) 3 -(5-fluoro-3 ,3 ,4,4-tetramethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline (a- 15) 3 -(5-fluoro-3 ,3 ,4,4-tetramethyl-3 ,4-dihydroisoquinolin- 1 -yl)-6- fluoroquinoline
(a-16) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-l-yl)-8- fluoroquinoline
(a-17) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-l-yl)-8- methylquinoline
(a-18) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l -yl)quinoline (a- 19) 3 -(4,5-difluoro-3 ,3 -dimethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline,
(a-20) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, or
a salt thereof.
8. A method for controlling plant disease, comprising applying the plant disease control composition according to any of claims 1 to 7.
9. A method for controlling plant disease, comprising simultaneously applying a plant disease control composition containing a quinoline compound (I) of group a according to claim 1 or 7 as an active ingredient thereof and a plant disease control composition containing a fungicidal compound of group b according to any of claims 1 to 6 as an active ingredient thereof, or applying one of either a plant disease control composition containing a quinoline compound (I) of group a according to claim 1 or 7 as an active ingredient thereof or a plant disease control composition containing a fungicidal compound of group b according to any of claims 1 to 6 as an active ingredient thereof, followed by applying the other composition.
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016060230A1 (en) * 2014-10-16 2016-04-21 日本農薬株式会社 Horticultural fungicide and method of using same
WO2017061483A1 (en) * 2015-10-09 2017-04-13 日本曹達株式会社 Agricultural and horticultural fungicidal composition
WO2017144231A1 (en) * 2016-02-26 2017-08-31 Basf Se Fungicidal mixtures comprising fluxapyroxad
WO2017154905A1 (en) * 2016-03-07 2017-09-14 石原産業株式会社 Method for enhancing plant disease controlling effect of isofetamid and method for controlling plant disease
WO2018054721A1 (en) * 2016-09-26 2018-03-29 Basf Se Pyridine compounds for controlling phytopathogenic harmful fungi
WO2018054711A1 (en) * 2016-09-26 2018-03-29 Basf Se Pyridine compounds for controlling phytopathogenic harmful fungi
WO2019059599A2 (en) 2017-09-19 2019-03-28 전남대학교산학협력단 Composition comprising acibenzolar-s-methyl as effective ingredient for controlling bursaphelenchus xylophilus disease and method for controlling bursaphelenchus xylophilus using same
US10779536B2 (en) 2014-11-07 2020-09-22 Basf Se Pesticidal mixtures
US10905122B2 (en) 2016-03-16 2021-02-02 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals
WO2021220231A1 (en) * 2020-05-01 2021-11-04 Pi Industries Ltd. Composition of propineb and metominostrobin
US11241012B2 (en) 2016-03-16 2022-02-08 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean
US11425909B2 (en) 2016-03-16 2022-08-30 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits
US11653650B2 (en) 2017-09-06 2023-05-23 Ishihara Sangyo Kaisha, Ltd. Fungicide composition and method for controlling disease of crop
WO2023148487A1 (en) * 2022-02-04 2023-08-10 UPL Corporation Limited Fungicidal combinations
US11974572B2 (en) 2017-03-31 2024-05-07 Sygenta Participations Ag Fungicidal compositions

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10966425B2 (en) * 2016-09-28 2021-04-06 Syngenta Participations Ag Fungicidal compositions
WO2019221089A1 (en) * 2018-05-16 2019-11-21 日本曹達株式会社 Phytotoxicity-reducing agent
CN110301436A (en) * 2019-08-13 2019-10-08 福建拓烯新材料科技有限公司 A kind of microcapsule formulations composition and preparation method thereof

Citations (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986002641A1 (en) 1984-10-29 1986-05-09 Sumitomo Chemical Company, Limited Pyrazolecarboxamide derivatives, process for their preparation, and bactericides containing them as effective ingredients
WO1995027693A1 (en) 1994-04-06 1995-10-19 Shionogi & Co., Ltd. α-SUBSTITUTED PHENYLACETIC ACID DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND AGRICULTURAL BACTERICIDE CONTAINING THE SAME
EP0936213A1 (en) 1998-02-10 1999-08-18 Rohm And Haas Company Unsaturated oxime ethers and their use as fungicides and insecticides
WO2001014339A2 (en) 1999-08-20 2001-03-01 Dow Agrosciences Llc Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation
WO2002006304A1 (en) 2000-07-13 2002-01-24 Isagro Ricerca S.R.L. Process for the preparation of dipeptide derivatives
WO2002012172A1 (en) 2000-08-08 2002-02-14 Dow Agrosciences Llc Unsaturated oxime ethers and their use as fungicides
WO2003016303A1 (en) 2001-08-20 2003-02-27 Dainippon Ink And Chemicals, Inc. Tetrazoyl oxime derivative and agricultural chemical containing the same as active ingredient
WO2005044813A1 (en) 2003-11-11 2005-05-19 Shenyang Research Institute Of Chemical Industry Benzopyrone compounds, preparation method and use thereof
WO2005070917A1 (en) 2004-01-23 2005-08-04 Sankyo Agro Company, Limited 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines
WO2006016708A1 (en) 2004-08-12 2006-02-16 Ishihara Sangyo Kaisha, Ltd. Fungicidal composition containing acid amide derivative
WO2006125370A1 (en) 2005-05-26 2006-11-30 Sinochem Corporation Aromatic ether compounds,preparation and usage thereof
WO2007000098A1 (en) 2005-06-28 2007-01-04 Sinochem Corporation SUBSTITUTED p-TRIFLUOROMETHYL PHENYLETHERS, THE PREPARATIO AND THE USE THEREOF
JP2007001944A (en) 2005-06-24 2007-01-11 Sankyo Agro Kk 3,4-dihydro-1,3'-biquinoline-2-one derivative
WO2007011022A1 (en) 2005-07-22 2007-01-25 Sankyo Agro Company, Limited 3-(isoquinoline-1-yl)quinoline derivative
WO2007066601A1 (en) 2005-12-07 2007-06-14 Sumitomo Chemical Company, Limited Pyridazine compound and use thereof
WO2007072999A1 (en) 2005-12-22 2007-06-28 Nihon Nohyaku Co., Ltd Pyrazinecarboxamide derivatives and plant disease controlling agents containing the same
JP2007217353A (en) 2006-02-17 2007-08-30 Sankyo Agro Kk 1,2,3,4-tetrahydroquinoline compound
WO2008145740A1 (en) 2007-06-01 2008-12-04 Basf Se Method for the production of n-substituted (3-dihalomethyl-1-methyl-pyrazole-4-yl) carboxamides
WO2008145052A1 (en) 2007-05-25 2008-12-04 Sinochem Corporation Substituted pyrimidine ether compounds and their use
WO2009094442A2 (en) 2008-01-22 2009-07-30 Dow Agrosciences Llc 5-fluoro pyrimidine derivatives
JP2010006746A (en) 2008-06-27 2010-01-14 Mitsui Chemicals Agro Inc Plant disease controlling composition and method of controlling plant disease by applying the same
US7666884B2 (en) 2005-02-06 2010-02-23 Shenyang Research Institute Of Chemical Industry N-(2-substituted phenyl)-N-methoxycarbamates and their preparation and use thereof
WO2010043319A1 (en) 2008-10-15 2010-04-22 Bayer Cropscience Aktiengesellschaft Use of dithiin tetracarboximides for treating phytopathogenic fungi
WO2010094728A1 (en) 2009-02-19 2010-08-26 Bayer Cropscience Ag Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance
WO2010136475A1 (en) 2009-05-29 2010-12-02 Syngenta Participations Ag Substituted quinazolines as fungicides
WO2010146006A2 (en) 2009-06-18 2010-12-23 Basf Se Fungicidal mixtures
WO2010149414A1 (en) 2009-04-24 2010-12-29 Basf Se 5-mercapto-[1, 2, 4] triazolylmethyl-cyclopentanol compounds and their agricultural and pharmaceutical uses
JP2011012017A (en) * 2009-07-01 2011-01-20 Mitsui Chemicals Agro Inc Vegetable blight and insect pest-controlling agent containing quinoline-based compound and method for controlling the same
WO2011015416A1 (en) 2009-08-06 2011-02-10 Syngenta Participations Ag Process for the preparation of pyrazole carboxylic acid amides
WO2011056463A2 (en) 2009-11-04 2011-05-12 E. I. Du Pont De Nemours And Company Fungicidal mixtures
WO2011070771A1 (en) 2009-12-08 2011-06-16 Kureha Corporation Azole derivatives, methods for producing the same, intermediate thereof, agro-horticultural agents
WO2011077514A1 (en) * 2009-12-22 2011-06-30 三井化学アグロ株式会社 Plant disease control composition and method for controlling plant diseases by applying the composition
WO2011085170A1 (en) 2010-01-07 2011-07-14 E. I. Du Pont De Nemours And Company Fungicidal heterocyclic compounds
WO2012019981A1 (en) 2010-08-09 2012-02-16 Basf Se Fungicidal mixtures
WO2012031061A2 (en) 2010-09-01 2012-03-08 E. I. Du Pont De Nemours And Company Fungicidal pyrazoles and their mixtures
WO2012172061A1 (en) 2011-06-17 2012-12-20 Basf Se Compositions comprising fungicidal substituted dithiines and further actives
WO2013037717A1 (en) 2011-09-12 2013-03-21 Bayer Intellectual Property Gmbh Fungicidal 4-substituted-3-{phenyl[(heterocyclylmethoxy)imino]methyl}-1,2,4-oxadizol-5(4h)-one derivatives
WO2014079789A1 (en) * 2012-11-23 2014-05-30 Bayer Cropscience Ag Active compound combinations

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI384949B (en) 2006-12-01 2013-02-11 A soil treating agent or seed treating agent comprising quinoline compounds or salts thereof as an active ingredient, or a method for preventing plant diseases by using the same
JP5631540B2 (en) 2007-11-05 2014-11-26 石原産業株式会社 Bactericidal composition and method for controlling harmful fungi
JP2011157294A (en) * 2010-01-29 2011-08-18 Mitsui Chemicals Agro Inc Pest-controlling composition
JP2014015470A (en) * 2013-09-03 2014-01-30 Sumitomo Chemical Co Ltd Noxious organism control composition and use thereof
AR098031A1 (en) 2013-10-16 2016-04-27 Bayer Cropscience Ag COMBINATIONS OF ACTIVE COMPOUNDS THAT INCLUDE A DERIVATIVE OF (UNCLE) CARBOXAMIDE AND A FUNGIED COMPOUND
ES2675555T3 (en) * 2014-02-19 2018-07-11 Bayer Cropscience Aktiengesellschaft Fungicidal compositions of pyrazolecarboxylic acid alkoxyamides

Patent Citations (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986002641A1 (en) 1984-10-29 1986-05-09 Sumitomo Chemical Company, Limited Pyrazolecarboxamide derivatives, process for their preparation, and bactericides containing them as effective ingredients
WO1995027693A1 (en) 1994-04-06 1995-10-19 Shionogi & Co., Ltd. α-SUBSTITUTED PHENYLACETIC ACID DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND AGRICULTURAL BACTERICIDE CONTAINING THE SAME
EP0936213A1 (en) 1998-02-10 1999-08-18 Rohm And Haas Company Unsaturated oxime ethers and their use as fungicides and insecticides
WO2001014339A2 (en) 1999-08-20 2001-03-01 Dow Agrosciences Llc Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation
WO2002006304A1 (en) 2000-07-13 2002-01-24 Isagro Ricerca S.R.L. Process for the preparation of dipeptide derivatives
WO2002012172A1 (en) 2000-08-08 2002-02-14 Dow Agrosciences Llc Unsaturated oxime ethers and their use as fungicides
WO2003016303A1 (en) 2001-08-20 2003-02-27 Dainippon Ink And Chemicals, Inc. Tetrazoyl oxime derivative and agricultural chemical containing the same as active ingredient
WO2005044813A1 (en) 2003-11-11 2005-05-19 Shenyang Research Institute Of Chemical Industry Benzopyrone compounds, preparation method and use thereof
WO2005070917A1 (en) 2004-01-23 2005-08-04 Sankyo Agro Company, Limited 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines
WO2006016708A1 (en) 2004-08-12 2006-02-16 Ishihara Sangyo Kaisha, Ltd. Fungicidal composition containing acid amide derivative
US7666884B2 (en) 2005-02-06 2010-02-23 Shenyang Research Institute Of Chemical Industry N-(2-substituted phenyl)-N-methoxycarbamates and their preparation and use thereof
WO2006125370A1 (en) 2005-05-26 2006-11-30 Sinochem Corporation Aromatic ether compounds,preparation and usage thereof
JP2007001944A (en) 2005-06-24 2007-01-11 Sankyo Agro Kk 3,4-dihydro-1,3'-biquinoline-2-one derivative
WO2007000098A1 (en) 2005-06-28 2007-01-04 Sinochem Corporation SUBSTITUTED p-TRIFLUOROMETHYL PHENYLETHERS, THE PREPARATIO AND THE USE THEREOF
WO2007011022A1 (en) 2005-07-22 2007-01-25 Sankyo Agro Company, Limited 3-(isoquinoline-1-yl)quinoline derivative
WO2007066601A1 (en) 2005-12-07 2007-06-14 Sumitomo Chemical Company, Limited Pyridazine compound and use thereof
WO2007072999A1 (en) 2005-12-22 2007-06-28 Nihon Nohyaku Co., Ltd Pyrazinecarboxamide derivatives and plant disease controlling agents containing the same
JP2007217353A (en) 2006-02-17 2007-08-30 Sankyo Agro Kk 1,2,3,4-tetrahydroquinoline compound
WO2008145052A1 (en) 2007-05-25 2008-12-04 Sinochem Corporation Substituted pyrimidine ether compounds and their use
WO2008145740A1 (en) 2007-06-01 2008-12-04 Basf Se Method for the production of n-substituted (3-dihalomethyl-1-methyl-pyrazole-4-yl) carboxamides
WO2009094442A2 (en) 2008-01-22 2009-07-30 Dow Agrosciences Llc 5-fluoro pyrimidine derivatives
JP2010006746A (en) 2008-06-27 2010-01-14 Mitsui Chemicals Agro Inc Plant disease controlling composition and method of controlling plant disease by applying the same
WO2010043319A1 (en) 2008-10-15 2010-04-22 Bayer Cropscience Aktiengesellschaft Use of dithiin tetracarboximides for treating phytopathogenic fungi
WO2010094728A1 (en) 2009-02-19 2010-08-26 Bayer Cropscience Ag Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance
WO2010149414A1 (en) 2009-04-24 2010-12-29 Basf Se 5-mercapto-[1, 2, 4] triazolylmethyl-cyclopentanol compounds and their agricultural and pharmaceutical uses
WO2010136475A1 (en) 2009-05-29 2010-12-02 Syngenta Participations Ag Substituted quinazolines as fungicides
WO2010146006A2 (en) 2009-06-18 2010-12-23 Basf Se Fungicidal mixtures
JP2011012017A (en) * 2009-07-01 2011-01-20 Mitsui Chemicals Agro Inc Vegetable blight and insect pest-controlling agent containing quinoline-based compound and method for controlling the same
WO2011015416A1 (en) 2009-08-06 2011-02-10 Syngenta Participations Ag Process for the preparation of pyrazole carboxylic acid amides
WO2011056463A2 (en) 2009-11-04 2011-05-12 E. I. Du Pont De Nemours And Company Fungicidal mixtures
WO2011070771A1 (en) 2009-12-08 2011-06-16 Kureha Corporation Azole derivatives, methods for producing the same, intermediate thereof, agro-horticultural agents
WO2011077514A1 (en) * 2009-12-22 2011-06-30 三井化学アグロ株式会社 Plant disease control composition and method for controlling plant diseases by applying the composition
WO2011085170A1 (en) 2010-01-07 2011-07-14 E. I. Du Pont De Nemours And Company Fungicidal heterocyclic compounds
WO2012019981A1 (en) 2010-08-09 2012-02-16 Basf Se Fungicidal mixtures
WO2012031061A2 (en) 2010-09-01 2012-03-08 E. I. Du Pont De Nemours And Company Fungicidal pyrazoles and their mixtures
WO2012172061A1 (en) 2011-06-17 2012-12-20 Basf Se Compositions comprising fungicidal substituted dithiines and further actives
WO2013037717A1 (en) 2011-09-12 2013-03-21 Bayer Intellectual Property Gmbh Fungicidal 4-substituted-3-{phenyl[(heterocyclylmethoxy)imino]methyl}-1,2,4-oxadizol-5(4h)-one derivatives
WO2014079789A1 (en) * 2012-11-23 2014-05-30 Bayer Cropscience Ag Active compound combinations

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
COLBY SR: "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", WEED, vol. 15, 1967, pages 20 - 22, XP001112961
See also references of EP3119200A4

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016060230A1 (en) * 2014-10-16 2016-04-21 日本農薬株式会社 Horticultural fungicide and method of using same
US10779536B2 (en) 2014-11-07 2020-09-22 Basf Se Pesticidal mixtures
RU2720251C2 (en) * 2015-10-09 2020-04-28 Ниппон Сода Ко., Лтд. Fungicidal composition for use in agriculture and horticulture
KR102569067B1 (en) * 2015-10-09 2023-08-21 닛뽕소다 가부시키가이샤 Fungicide composition for agricultural and horticultural use
AU2016334757B2 (en) * 2015-10-09 2020-05-21 Nippon Soda Co., Ltd. Agricultural and horticultural fungicidal composition
CN108135171B (en) * 2015-10-09 2020-10-20 日本曹达株式会社 Agricultural and horticultural bactericide composition
CN108135171A (en) * 2015-10-09 2018-06-08 日本曹达株式会社 Agricultural or horticultural use microbicide compositions
KR20180064404A (en) * 2015-10-09 2018-06-14 닛뽕소다 가부시키가이샤 Composition for agricultural and horticultural use
JPWO2017061483A1 (en) * 2015-10-09 2018-07-26 日本曹達株式会社 Agricultural / horticultural fungicide composition
WO2017061483A1 (en) * 2015-10-09 2017-04-13 日本曹達株式会社 Agricultural and horticultural fungicidal composition
US10463043B2 (en) 2015-10-09 2019-11-05 Nippon Soda Co., Ltd. Fungicide composition for agricultural and horticultural use
EP3360415A4 (en) * 2015-10-09 2019-04-03 Nippon Soda Co., Ltd. Agricultural and horticultural fungicidal composition
WO2017144231A1 (en) * 2016-02-26 2017-08-31 Basf Se Fungicidal mixtures comprising fluxapyroxad
KR20180114931A (en) * 2016-03-07 2018-10-19 이시하라 산교 가부시끼가이샤 A method for enhancing the plant disease control effect of isopotamide and a method for controlling the plant disease
IL261477A (en) * 2016-03-07 2018-10-31 Ishihara Sangyo Kaisha Method for enhancing plant disease controlling effects of isofetamid and method for controlling plant diseases
CN108697085A (en) * 2016-03-07 2018-10-23 石原产业株式会社 The Enhancement Method and method for controlling plant disease of the plant disease control effect of isopropyl metsulfovax
WO2017154905A1 (en) * 2016-03-07 2017-09-14 石原産業株式会社 Method for enhancing plant disease controlling effect of isofetamid and method for controlling plant disease
JPWO2017154905A1 (en) * 2016-03-07 2018-12-27 石原産業株式会社 Method for enhancing plant disease control effect of isofetamide and method for controlling plant disease
RU2739947C2 (en) * 2016-03-07 2020-12-30 Исихара Сангио Кайся, Лтд. Method of intensifying the effects of isofetamid control of plant diseases and a method of controlling plant diseases
AU2017230471B2 (en) * 2016-03-07 2021-07-22 Ishihara Sangyo Kaisha, Ltd. Method for enhancing plant disease controlling effect of isofetamid and method for controlling plant disease
KR102317161B1 (en) * 2016-03-07 2021-10-26 이시하라 산교 가부시끼가이샤 Method for enhancing plant disease control effect of isopetamide and control method for plant disease
US11412733B2 (en) 2016-03-07 2022-08-16 Ishihara Sangyo Kaisha, Ltd. Method for enhancing plant disease controlling effects of isofetamid and method for controlling plant diseases
US11425909B2 (en) 2016-03-16 2022-08-30 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits
US11241012B2 (en) 2016-03-16 2022-02-08 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean
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WO2018054721A1 (en) * 2016-09-26 2018-03-29 Basf Se Pyridine compounds for controlling phytopathogenic harmful fungi
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US11974572B2 (en) 2017-03-31 2024-05-07 Sygenta Participations Ag Fungicidal compositions
US11653650B2 (en) 2017-09-06 2023-05-23 Ishihara Sangyo Kaisha, Ltd. Fungicide composition and method for controlling disease of crop
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