Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
• • 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
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
  • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
• • 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
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/12—Powders or granules
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P3/00—Fungicides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
  • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
  • C07D471/04—Ortho-condensed systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
  • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
  • C07D471/14—Ortho-condensed systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
  • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
  • C07D487/04—Ortho-condensed systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
  • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
  • C07D495/04—Ortho-condensed systems

Definitions

• the present invention relates to an agricultural and horticultural fungicide containing an oxadiazolin compound or a salt thereof as an active ingredient, and a method for using the same.
• Patent Documents 1 and 2 describe that a compound having oxadiazoline having a trifluoromethyl group in its structure has a bactericidal activity against a causative bacterium of a plant disease. However, there is no specific description in those documents regarding the compound in which the oxadiazolin ring is bound to thiophene.
• the present inventors have found that the compound represented by the general formula (I) of the present invention or a salt thereof is useful as a bactericidal agent for agriculture and horticulture. , The present invention has been completed.
• L represents any structure of the following structural formulas L 1 , L 2 or L 3 .
• Q is (a1) (C 1- C 6 ) Alkyl group; (a2) (C 2- C 6 ) Alkenyl group; (a3) (C 2 -C 6 ) alkynyl group; (a4) (C 3- C 6 ) Cycloalkyl group; (a5) (C 1- C 6 ) Alkoxy group; (a6) Halo (C 1- C 6 ) alkyl group; (a7) halo (C 2 -C 6) alkenyl group; (a8) halo (C 2 -C 6) alkynyl group; (a9) Halo (C 3- C 8 ) cycloalkyl group; (a10) Halo (C 1- C 6 ) alkoxy group; (a11) (C 1- C 6 ) Alkylthio group; (a12) (C 1- C 6 ) Alkyl sul
• R 1 and R 2 are independent of each other (b1) Hydrogen atom; (b2) Halogen atom; (b3) (C 1- C 6 ) Alkyl group; (b4) Halo (C 1- C 6 ) alkyl group; or (b5) (C 1- C 6 ) Shows an alkoxy group.
• R 1 and R 2 may be combined with their bonded carbon atoms to form a cyclopropane ring.
• R 3 and R 4 are independent of each other (c1) Hydrogen atom; (c2) (C 1- C 6 ) Alkyl group; (c3) (C 2 -C 6 ) alkenyl group; (c4) (C 2 -C 6 ) alkynyl group; (c5) (C 3- C 6 ) Cycloalkyl group; (c6) (C 1- C 6 ) Alkoxy group; (c7) Halo (C 1- C 6 ) alkyl group; (c8) (C 1- C 6 ) Alkylthio group; (c9) (C 1- C 6 ) Alkyl sulfinyl group; (c10) (C 1- C 6 ) Alkylsulfonyl group; (c11) (C 3- C 6 ) Cycloalkylsulfonyl group; (c12) Phenylsulfonyl group; (c13) (C 3- C 6 ) cycloalkyl (C 1- C 6 ) alkyl group; (c14) (C
• R 5 is (d1) Hydrogen atom; (d2) (C 1- C 6 ) Alkyl group; (d3) (C 1- C 6 ) Alkylcarbonyl group; (d4) (C 1- C 6 ) Alkoxycarbonyl group; or (d5) (C 1- C 6 ) Alkyl (C 1- C 6 ) Alkyl group is shown.
• Q is (a1) (C 1- C 6 ) Alkyl group; (a11) (C 1- C 6 ) Alkylthio group; (a12) (C 1- C 6 ) Alkyl sulfinyl group; (a13) (C 1- C 6 ) Alkylsulfonyl group; (a17) R 3 (R 4 ) N groups; or (a21) Independently, halogen atom, cyano group, nitro group, (C 1- C 6 ) alkyl group, (C 1- C 6 ) alkoxy group, (C 3- C 6 ) cycloalkyl group, halo (C 3-C 6) 1- C 6 ) alkyl group, halo (C 1- C 6 ) alkoxy group, halo (C 3- C 6 ) cycloalkyl group, (C 1- C 6 ) alkyl thio group, (C 1- C 6 ) alkyl sulfinyl Group, (C
• R 1 and R 2 are independent of each other (b1) Hydrogen atom; (b3) (C 1- C 6 ) Alkyl group; or (b5) (C 1- C 6 ) Shows an alkoxy group and R 3 and R 4 are independent (c1) Hydrogen atom; (c2) (C 1- C 6 ) Alkyl group; (c3) (C 2 -C 6 ) alkenyl group; (c4) (C 2 -C 6 ) alkynyl group; (c5) (C 3- C 6 ) Cycloalkyl group; (c6) (C 1- C 6 ) Alkoxy group; (c10) (C 1- C 6 ) Alkylsulfonyl group; (c11) (C 3- C 6 ) Cycloalkylsulfonyl group; (c12) Phenylsulfonyl group; (c13) (C 3- C 6 ) cycloalkyl (C 1- C 6 ) alkyl group; (c14) (C 1- C 6 ) Alk
• Q is (a13) (C 1- C 6 ) Alkylsulfonyl group; (a17) R 3 (R 4 ) N groups; or (a21) Independently, halogen atom, cyano group, nitro group, (C 1- C 6 ) alkyl group, (C 1- C 6 ) alkoxy group, (C 3- C 6 ) cycloalkyl group, halo (C 3-C 6) 1- C 6 ) alkyl group, halo (C 1- C 6 ) alkoxy group, halo (C 3- C 6 ) cycloalkyl group, (C 1- C 6 ) alkyl thio group, (C 1- C 6 ) alkyl sulfinyl Group, (C 1- C 6 ) alkyl sulfonyl group, halo (C 1- C 6 ) alkyl thio group, halo (C 1- C 6 ) alkyl sulfinyl group, halo (C 1- C 6
• R 3 and R 4 are independent (c1) Hydrogen atom; (c2) (C 1- C 6 ) Alkyl group; (c10) (C 1- C 6 ) Alkylsulfonyl group; (c14) (C 1- C 6 ) Alkoxy (C 1- C 6 ) Alkoxycarbonyl group; (c20) (C 1- C 6 ) Alkylcarbonyl group; (c22) (C 3- C 6 ) Cycloalkylcarbonyl group; (c23) Benzoyl group; (c24) Mono ((C 1- C 6 ) alkyl) aminocarbonyl group; (c30) Tetrahydropyran-4-ylcarbonyl group; (c34) Formylation group; or (c35) Shows a pyrimidinyl group, R 5 (d1) The compound according to the above [1] or [2] or a salt thereof, which represents a hydrogen atom.
• a fungicide comprising the compound according to any one of [1] to [3] or salts thereof as an active ingredient.
• a method for controlling plant diseases which comprises treating a plant or soil with an effective amount of the fungicide according to the above [4].
• the present invention relates to the use of the compound according to any one of the above [1] to [3] or a salt thereof as a bactericide.
• the compound of the present invention or salts thereof has an excellent effect as a fungicide for agriculture and horticulture.
• Halo means "halogen atom” and indicates chlorine atom, bromine atom, iodine atom or fluorine atom.
• the "(C 1- C 6 ) alkyl group” means, for example, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a normal pentyl group, and an isopentyl group.
• (C 2 -C 6) alkenyl group for example, vinyl group, allyl group, isopropenyl group, 1-butenyl, 2-butenyl, 2-methyl-2-propenyl group, 1-methyl-2 -Propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, etc.
• the "(C 2 -C 6) alkynyl group” such as ethynyl group, 1-propynyl, 2-propynyl, 1-butynyl group, 2-butynyl, 3-butynyl, 3-methyl - Linear or split chain such as 1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,3-dimethyl-1-butynyl group, etc. Shows an alkynyl group having 2 to 6 carbon atoms.
• the “(C 3- C 6 ) cycloalkyl group” indicates, for example, a cyclic alkyl group having 3 to 6 carbon atoms such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group, and “(C 1”.
• the "-C 6 ) alkoxy group” includes, for example, a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal butoxy group, a secondary butoxy group, a tertiary butoxy group, a normal pentyloxy group, an isopentyloxy group, and a tasha.
• Lepentyloxy group neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normalhexyloxy group, isohexyloxy group, 1,1,2-trimethyl Indicates a linear or branched alkoxy group having 1 to 6 carbon atoms such as a propyloxy group.
• the "(C 1- C 6 ) alkyl thio group” means, for example, a methyl thio group, an ethyl thio group, a normal propyl thio group, an isopropyl thio group, a normal butyl thio group, a secondary butyl thio group, a tertiary butyl thio group, a normal pentyl thio group.
• the “(C 1- C 6 ) alkyl sulfinyl group” means, for example, a methyl sulfinyl group, an ethyl sulfinyl group, a normal propyl sulfinyl group, an isopropyl sulfinyl group, a normal butyl sulfinyl group, a secondary butyl sulfinyl group, a tertiary butyl sulfinyl group, and the like.
• Normal Pentyl Sulfinyl Group Isopentyl Sulfinyl Group, Terriary Pentyl Sulfinyl Group, Neopentyl Sulfinyl Group, 2,3-Dimethylpropyl Sulfinyl Group, 1-Ethylpropyl Sulfinyl Group, 1-Methyl Butyl Sulfinyl Group, Normal Hexyl Sulfinyl Group, Iso It shows a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a hexylsulfinyl group and a 1,1,2-trimethylpropylsulfinyl group.
• the "(C 1- C 6 ) alkyl sulfonyl group” means, for example, a methyl sulfonyl group, an ethyl sulfonyl group, a normal propyl sulfonyl group, an isopropyl sulfonyl group, a normal butyl sulfonyl group, a secondary butyl sulfonyl group, a tertiary butyl sulfonyl group, and the like.
• Normal pentylsulfonyl group isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normalhexylsulfonyl group, iso It shows a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms, such as a hexylsulfonyl group and a 1,1,2-trimethylpropylsulfonyl group.
• the “(C 1- C 6 ) alkylcarbonyl group” means, for example, an acetyl group, a propanoyl group, a butanoyl group, a 2-methylpropanoyl group, a pentanoyl group, a 2-methylbutanoyl group, a 3-methylbutanoyl group, and the like. shown pivaloyl group, a hexanoyl group, wherein such cyclopropylcarbonyl group such as an alkyl carbonyl group having a (C 1 -C 6) alkyl group, an alkylcarbonyl group having 2 to 7 carbon atoms.
• (C 1- C 6 ) alkoxycarbonyl group means, for example, methoxycarbonyl group, ethoxycarbonyl group, normal propoxycarbonyl group, isopropoxycarbonyl group, normal butoxycarbonyl group, isobutoxycarbonyl group, secondary butoxycarbonyl group, shown tert-butoxycarbonyl group, such as alkoxycarbonyl groups having a (C 1 -C 6) alkoxy group such as pentyloxy group, an alkoxycarbonyl group having 2 to 7 carbon atoms.
• halogen atoms may be substituted at the substitutable positions of, and when the number of halogen atoms to be substituted is two or more, the halogen atoms may be the same or different.
• These groups are referred to as "halo (C 1- C 6 ) alkyl group", “halo (C 2- C 6 ) alkenyl group”, “halo (C 2- C 6 ) alkynyl group”, and “halo (C 3)", respectively.
• aryl group and “aryl” indicate, for example, an aromatic hydrocarbon group having 6 to 10 carbon atoms, such as a phenyl group and a naphthyl group.
• the “5- to 6-membered heterocycle” indicates, for example, a structure as shown below. ⁇ Indicates the connection position.
• the “8 to 10-membered condensed heterocycle” has, for example, a structure as shown below. ⁇ Indicates the connection position.
• salts of the compound represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochlorides, sulfates, nitrates and phosphates, acetates, fumarates, maleates and oxalates.
• examples thereof include organic acid salts such as methane sulfonate, benzene sulfonate and paratoluene sulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion and trimethylammonium.
• the compound represented by the general formula (I) of the present invention and salts thereof may have one or more asymmetric centers in the structural formula, and two or more kinds of optical isomers and diastereomers may be present. In some cases, the present invention also includes all optical isomers and mixtures containing them in arbitrary proportions. Further, the compound represented by the general formula (I) of the present invention and salts thereof may have two kinds of geometric isomers derived from carbon-carbon double bonds in the structural formula, but the present invention Also includes all geometric isomers and mixtures containing them in arbitrary proportions.
• Q (a1) (C 1- C 6 ) Alkyl group; (a11) (C 1- C 6 ) Alkylthio group; (a12) (C 1- C 6 ) Alkyl sulfinyl group; (a13) (C 1- C 6 ) Alkylsulfonyl group; (a17) R 3 (R 4 ) N groups; or (a21) Independently, halogen atom, cyano group, nitro group, (C 1- C 6 ) alkyl group, (C 1- C 6 ) alkoxy group, (C 3- C 6 ) cycloalkyl group, halo (C 3-C 6) 1- C 6 ) alkyl group, halo (C 1- C 6 ) alkoxy group, halo (C 3- C 6 ) cycloalkyl group, (C 1- C 6 ) alkyl thio group, (C 1- C 6 )
• R 1 and R 2 are preferably independent of each other.
• R 3 and R 4 are preferably independent of each other.
• R 5 Preferably as R 5, (d1) Hydrogen atom; or (d2) (C 1- C 6 ) Alkyl group, More preferably (d1) It is a hydrogen atom.
• HDAC4 inhibitory activity are preferable. Since HDAC exhibits multifaceted effects, its inhibitors are expected to be used as anticancer agents and the like. However, due to its multifaceted nature, non-selective inhibition and excessive inhibition have the potential to develop various toxicities such as teratogenicity (Herberland, M., Nat. Rev. Genet. , 2009, 10, 32-42. And Currant Pharmaceutical Design, 2014, Vol. 20, No. 00).
• the various compounds of the present invention can be produced by, for example, the following production methods, but the production method of the compound of the present invention is not limited thereto.
• Step [a] A step of producing a compound represented by the general formula (I-1) by reducing the compound represented by the general formula (3).
• Step [b] A step of producing a compound represented by the general formula (I-2) by reacting the compound represented by the general formula (I-1) with the compound represented by the general formula (2).
• the compounds represented by the general formula (I-1) are International Publication No. 2019/131867, International Publication No. 2017/213252 Pamphlet, International Publication No. 2017/055473 Pamphlet, International Publication No. 2015/ 185485 Pamphlet, International Publication No. 2017/118689 Pamphlet, International Publication No. 2017/080859 Pamphlet, International Publication No. 2013/008162 Pamphlet, International Publication No. 2017/076935 Pamphlet, International Publication No. 2015/185485 Pamphlet and Special It can be produced by reacting a compound represented by the general formula (3), which can be produced by the method described in Kaisho 63-162680, with a reducing agent in an inert solvent.
• Examples of the reducing agent that can be used in this reaction include lithium aluminum hydride, sodium aluminum hydride, sodium borohydride, sodium cyanoborohydride, and the like.
• the compound represented by 3) may be appropriately selected from the range of 0.25 times mol to 2 times mol.
• the inert solvent used in this reaction may be any solvent as long as it does not significantly inhibit the progress of this reaction.
• aliphatic hydrocarbons such as pentane, hexane and cyclohexane; diethyl ether, methyl tertiary butyl ether and cyclopentylmethyl.
• Ethers such as ethers, tetrahydrofuran and dioxane; inert solvents such as alcohols such as methanol, ethanol, 1-propanol and 2-propanol can be exemplified, and these inert solvents can be used alone or in combination of two or more.
• the amount to be used may be appropriately selected from the range of usually 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (3).
• reaction temperature can be usually carried out in the boiling point range of the inert solvent used from room temperature, and the reaction time is not constant depending on the reaction scale and the reaction temperature, but is usually in the range of several minutes to 48 hours.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
• the compound represented by the general formula (I-2) contains a compound represented by the general formula (I-1) and a compound represented by the general formula (2) as a base. Below, it can be produced by reacting in an inert solvent.
• bases examples include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc .; sodium hydride, hydrogenation.
• Alkali metal hydrides such as potassium; Alkali metal alkoxides such as potassium t-butoxide, sodium methoxydo, sodium ethoxydo; triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, etc.
• Tertiary amines nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine can be exemplified, and the amount used thereof is usually 1-fold molar amount of the compound represented by the general formula (I-1). It may be appropriately selected from the range of up to 5 times the molar amount.
• the inert solvent used in this reaction may be any solvent as long as it does not significantly inhibit the progress of this reaction.
• aromatic hydrocarbons such as benzene, toluene and xylene; methylene chloride, chloroform, carbon tetrachloride and the like.
• Halogenized hydrocarbons Halogenized aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, cyclopentyl methyl ether, dioxane, tetrahydrofuran, and esters such as ethyl acetate.
• Amidos such as dimethylformamide and dimethylacetamide; Ketones such as acetone and methylethylketone; Aprotonic polar solvents such as dimethylsulfoxide and 1,3-dimethyl-2-imidazolidinone can be exemplified.
• the inert solvent can be used alone or in combination of two or more. The amount to be used may be appropriately selected from the range of usually 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (I-1).
• reaction temperature can be usually carried out in the boiling point range of the inert solvent used from room temperature, and the reaction time is not constant depending on the reaction scale and the reaction temperature, but is usually in the range of several minutes to 48 hours.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
• the agricultural and horticultural fungicides containing the compound represented by the general formula (I) of the present invention or salts thereof as an active ingredient are suitable for controlling diseases occurring in cereals, fruit trees, vegetables, other crops and flowers.
• Target diseases include filamentous fungal diseases, bacterial diseases, viral diseases, and the like.
• Filamentous fungal diseases include, for example, diseases caused by incomplete fungi (for example, Botrytis disease, Helminthosporium disease, Fusarium disease, Septoria disease, Sercospora).
• Genus disease Pseudocercosporella genus disease, Rynchosporium genus disease, Pyricularia genus disease, Alternaria genus disease, Alternaria genus disease, etc.); Genus disease, Rhizoctonia disease, Ustylago disease, Typhula disease, Puccinia disease, etc.); Diseases caused by ascospores (for example, Venturia disease, Venturia disease) (Podosphaera) disease, Leptosphaeria disease, Blumeria disease, Elysiphe disease, Microdocium disease, Microdochium disease, Screlothinia Diseases, diseases of the genus Monilinia, diseases of the genus Unsinula, etc.); Diseases caused by and other fungi (eg, diseases of the genus Ascochyta, diseases of the genus Phoma, diseases of the genus Phythium, cortium) (Corticium) genus disease, Pyrenophora
• filamentous fungal diseases include, for example, powdery mildew (Pyricularia oryzae), powdery mildew (Rhizoctonia solani), powdery mildew (Cochiobolus miyabeanus), and Fusarium seedlings (Fusarium fusarium).
• Powdery mildew powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mild
• Various plant vegetation diseases such as viticola), apple scab (Venturia inaequalis), apple scab deciduous disease (Alternaria mari), pear scab (Alternaria kikuchiana), citrus scab (Diaporthe citrus) (Elsinoe fawcetti), Cercospora beticola, Cercospora arachidicola, Cercospora persona, Wheat leaf blight (Cercospora), Wheat leaf blight (Septori) Apple scab (Pyrenophora teres), apple scab (Pyrenophora graminea), apple scab (Rhinchosporium ceralis), wheat scab (Ustilago nuda), wheat scab (Ustilago nuda), wheat scab (wheat scab) Examples include Rhizoctonia solani) and Cercospora homeocarpa (Cercospora).
• Specific diseases of bacterial diseases include diseases caused by the genus Pseudomonas, for example, Pseudomonas syringae pv. Lachrymans, Pseudomonas solanacearum, Xanthomonas genus Xanthomonas, and rice blight. Diseases caused by, for example, Xanthomonas bacterium, Xanthomonas oryzae and Xanthomonas citri, diseases caused by the genus Erwinia, such as cabbage soft rot.
• the useful plants to which the compound represented by the general formula (I) of the present invention or salts thereof can be used are not particularly limited, but for example, grains (for example, rice, barley, wheat, melon, oat, etc. Corn, etc.), beans (soybeans, red beans, sky beans, pea, green onions, peanuts, etc.), fruit trees / fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherry blossoms, melons, chestnuts, almonds, bananas, etc.) , Leaves and fruit vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, green onion (asatsuki, scallions), peppers, eggplant, strawberry, pepper, okura, nira, etc.), root vegetables (carrot, horse bell melon, sweet potato, satoimo) , Daikon, Kabu, Renkon, Gobo, Carrot, Rakkyo, etc.), Processing crops (Fruit, hemp, Beet, Hop,
• plants include HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapill and thifensulfuronmethyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as gluhosinate, and setoxydim. Also included are plants that have been imparted to resistance to herbicides such as acetyl-CoA carboxylase inhibitors, bromoxynyl, dicamba, 2,4-D by classical breeding methods or genetic recombination techniques.
• HPPD inhibitors such as isoxaflutol
• ALS inhibitors such as imazetapill and thifensulfuronmethyl
• EPSP synthase inhibitors such as glyphosate
• glutamine synthase inhibitors such as gluhosinate
• setoxydim setoxydim.
• plants that have been imparted to resistance to herbicides such as acetyl-CoA carboxylase inhibitors, bromoxynyl
• plants that have been endowed with resistance by classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapill, and the trade name of Clearfield (registered trademark). Already sold at. Similarly, there are soybeans resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuronmethyl by classical breeding methods, which are already sold under the trade name of STS soybeans.
• SR corn and the like are examples of plants to which resistance to acetyl-CoA carboxylase inhibitors such as trionoxime-based and aryloxyphenoxypropionic acid-based herbicides has been imparted by classical breeding methods. Plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors are the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA) 87, pp. 7175-7179 (1990), etc. In addition, mutant acetyl CoA carboxylase resistant to acetyl CoA carboxylase inhibitors has been reported in Weed Science, Vol. 53, pp.
• toxins expressed in transgenic plants ⁇ - such as bacillus seleus and bacillus popiliae-derived insecticidal proteins; Endotoxins; insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP) such as lysine, corn-RIP, abrin, rufin, saporin, briozin; 3- Steroid metabolizing enzymes such as hydroxysteroid oxidase, exdisteroid-UDP-glucosyl transferase, cholesterol oxidase; ecdison inhibitor; HMG-Co
• ⁇ -endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab; Insecticidal protein hybrid toxins; partially deficient toxins; modified toxins are also included.
• Hybrid toxins are created using recombinant technology by a new combination of different domains of these proteins.
• Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
• the modified toxin one or more of the amino acids of the natural toxin have been replaced.
• Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073 and the like.
• the agricultural and horticultural fungicides of the present invention can be used in combination with these techniques or systematically.
• the agricultural and horticultural bactericide of the present invention is used as it is for controlling various diseases, or diluted or suspended with water or the like in an amount effective for disease control for plants in which the occurrence of the disease is predicted. It may be used, for example, for diseases occurring in fruit trees, grains, vegetables, etc., in addition to spraying on the foliage, soaking seeds in chemicals, seed treatment such as seed powder coating, calper treatment, etc., mixing all layers of soil It can also be used by treating it with soil, etc. and absorbing it from the roots, such as cropping, soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface application, etc. In addition, it can be applied to nutrient solution in hydroponic cultivation, smoked or injected into a tree trunk.
• the agricultural and horticultural fungicide of the present invention may be used as it is, or appropriately diluted with water or the like, or suspended in an amount effective for disease control in a place where the occurrence of the disease is predicted. ..
• a method of seed treatment for example, a method of immersing seeds in a liquid state without diluting or diluting a liquid or solid preparation to allow a drug to permeate, mixing a solid preparation or a liquid preparation with seeds, and powder coating.
• a method of treating and adhering to the surface of seeds a method of mixing with an adhesive carrier such as a resin or a polymer and coating the seeds, and a method of spraying the seeds at the same time as planting.
• the "seed" for which the seed treatment is performed means a plant body in the early stage of cultivation used for propagation of plants, for example, for bulbs, tubers, seed potatoes, plant buds, propagules, scales, or cuttings in addition to seeds. Plants for vegetative propagation can be mentioned.
• the "soil” or “cultivation carrier” of a plant when the method of use of the present invention is carried out indicates a support for cultivating a crop, particularly a support for growing roots, and the material is not particularly limited. However, any material can be used as long as it can grow plants, so-called soil, seedling mat, water, etc., and specific materials include, for example, sand, pebble, vermiculite, diatomaceous earth, agar, gel-like substance, and high. It may be a molecular substance, rock wool, glass wool, wood chips, bark or the like.
• a liquid preparation such as an emulsion or a flowable agent or a solid preparation such as a wettable powder or a granule wettable powder is appropriately diluted with water and sprayed, or a powder is sprayed.
• a powder is sprayed. Examples include fumigation.
• Examples of the method of application to soil include a method of applying a liquid preparation to a plant stock or a nursery for raising seedlings without diluting or diluting it with water, and a method of applying granules to a plant stock or seedling raising.
• Method of spraying on nursery, etc. method of spraying powder, wettable powder, granule wettable powder, granule, etc. before sowing or transplantation and mixing with the whole soil, planting hole, cropping before sowing or before planting Examples include a method of spraying a powder, a wettable powder, a granule wettable powder, a granule, etc. on the strips and the like.
• the dosage form may differ depending on the application time such as application at the time of sowing, application during the greening period, application at the time of transplantation, etc. It can be applied with a mold. It can also be applied by mixing with hilling soil, and can be mixed with hilling soil and powder, granule wettable powder, granules, etc., for example, bed soil mixing, soil covering mixing, mixing with the entire hilling soil, and the like. You may simply apply the hilling and various preparations in layers alternately.
• solid formulations such as jumbo agents, pack agents, granules and granule wettable powders, and liquid formulations such as flowables and emulsions are usually sprayed on paddy fields in a flooded state.
• an appropriate preparation can be sprayed or injected into the soil as it is or mixed with fertilizer.
• a chemical solution such as an emulsion or a flowable as an inflow source of water into a paddy field such as a water outlet or an irrigation device, it can be applied labor-savingly with the supply of water.
• the seedbed for raising seedlings is preferably irrigated with a liquid chemical or sprayed with granules. It is also preferable to treat the planting holes with granules at the time of planting or to mix them with a cultivation carrier near the transplanting site.
• the compound represented by the general formula (I) of the present invention or a salt thereof is generally formulated and used in a shape convenient for use according to a conventional method for pesticide preparation.
• the compound represented by the general formula (I) of the present invention or a salt thereof is dissolved, separated, or suspended by blending them with an appropriate inert carrier or, if necessary, with an auxiliary agent in an appropriate ratio.
• Turbidity, mixing, impregnation, adsorption or adhesion, and appropriate dosage forms such as suspending agents (flowable agents), emulsions, oils, liquids, wettable powders, granule wettable powders, granules, powders, tablets, packs, It may be used as a formulation in a jumbo agent, a suspension emulsion, or the like.
• the agricultural and horticultural fungicide of the present invention can contain, if necessary, an additive component usually used in pesticide preparations, in addition to the active ingredient.
• additive components include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, spreading agents, and antifreeze agents. , Anticaking agent, disintegrant, decomposition inhibitor and the like.
• preservatives, plant pieces and the like may be used as additive components. These additive components may be used alone or in combination of two or more.
• the solid carrier examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, cericite, talc, bentonite, acidic white clay, attapulsite, zeolite and diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride.
• natural minerals such as quartz, clay, kaolinite, pyrophyllite, cericite, talc, bentonite, acidic white clay, attapulsite, zeolite and diatomaceous earth
• inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride.
• Synthetic silicic acid synthetic silicate, starch, cellulose, organic solid carriers such as plant powders (eg, shavings, coconut husks, corn stalks, tobacco stems, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea, Examples thereof include an inorganic hollow body, a plastic hollow body, and fumed silica (white carbon). These may be used alone or in combination of two or more.
• liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerin.
• monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol
• polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerin.
• Such alcohols polyhydric alcohol compounds such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, THF and the like.
• ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, THF and the like.
• Ethers normal paraffins, naphthenes, isoparaffins, kerosines, aliphatic hydrocarbons such as mineral oils, aromatic hydrocarbons such as benzene, toluene, xylene, solventnaphtha, alkylnaphthalene, dichloromethane, chloroform, carbon tetrachloride, etc.
• Halogenated hydrocarbons ethyl acetate, diisopropylphthalate, dibutylphthalate, dioctylphthalate, esters such as dimethyl adipate, lactones such as ⁇ -butyrolactone, dimethylformamide, diethylformamide, dimethylacetamide, amides such as N-alkylpyrrolidinone.
• Examples include nitriles such as acetonitrile, sulfur compounds such as dimethyl sulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil, and water. These may be used alone or in combination of two or more.
• surfactant used as a dispersant and a wettable powder examples include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, and polyoxyethylene fatty acid diester.
• binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, citrus sugar, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000.
• Thickeners include, for example, xanthan gum, guar gum, daiyutan gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound, water-soluble polymer such as polysaccharide, high-purity bentonite, fumed silica (fumed). Examples thereof include inorganic fine powders such as silica (white carbon).
• colorant examples include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, alizarin dyes, azo dyes, and organic dyes such as metallic phthalocyanine dyes.
• antifreeze agent examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
• polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, etc.
• polysaccharides such as starch, alginic acid, mannose, and galactose
• polyvinylpyrrolidone fumed silica (white carbon)
• ester gum white carbon
• petroleum resin sodium tripolyphosphate, etc.
• examples include polymers.
• decomposition inhibitor examples include desiccants such as zeolite, quicklime and magnesium oxide, antioxidants such as phenol compounds, amine compounds, sulfur compounds and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. Be done.
• desiccants such as zeolite, quicklime and magnesium oxide
• antioxidants such as phenol compounds, amine compounds, sulfur compounds and phosphoric acid compounds
• ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. Be done.
• preservative examples include potassium sorbate, 1,2-benzothiazolin-3-one and the like.
• activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, and other supplements such as ultraviolet absorbers. Agents can also be used.
• the blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight out of 100 parts by weight of the agricultural and horticultural fungicide of the present invention. , 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural fungicide) is suitable for powders, granules, emulsions or wettable powders.
• the amount of the compound represented by the general formula (I) of the present invention or a salt thereof used is various factors such as purpose, target weed, crop growth condition, weed development tendency, weather, environmental condition, dosage form, application method. Although it varies depending on the place of application, the time of application, etc., the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 ares according to the purpose.
• fungicide for agriculture and horticulture containing the compound represented by the general formula (I) of the present invention or a salt thereof as an active ingredient, dilute it to an appropriate concentration and spray it or apply it as it is.
• the agricultural and horticultural fungicide of the present invention is another agricultural and horticultural insecticide, acaricide, herbicide, fungicide, for the purpose of expanding the disease to be controlled, the optimum time for control, or the purpose of reducing the amount of the drug. It can be mixed with biological pesticides and the like, and it can also be mixed with herbicides, plant growth regulators, fertilizers and the like depending on the usage situation. Representative compounds are exemplified below, but the compounds are not limited thereto.
• Other agricultural and horticultural fungicides used for this purpose include, for example, aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar S-methyl (acibenzolar-S-). methyl, azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, ambam, Isotianil, isovaledione, isopyrazam, isofetamid, isoprothiolane, ipconazole, iprodione, iprodione, iprovalicarb, iprovalicarb, iprovalicarb Iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, echlomez Edifenphos, etacon
• Agricultural and horticultural insecticides, acaricides, and nematode insecticides used for the same purpose include, for example. 3,5-xylyl methylcarbamate (XMC), Bacillus thuringiensis aizawai, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis kurstaki, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis tenebrionis chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1, 3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O
• Propatrin fenpropathrin
• fenbendazole fenbendazole
• pho Fosthiazate formetanate, butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluazaindolizine, fluazaindolizine, fluazinam Sulfone (fluensulfone), fluxametamide, flucycloxuron, flucythrinate, fluvalinate, flufiprole, flupyradifurone, flupyrazofos, flufenerim, flufenoxystrobin, flufenoxystrobin, flufenoxystrobin , Flufenzine, flufenoprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flumethrin, flurimfen, prothiophos (flurimfen) prothiofos), protrifenbute, flonica
• Herbicides used for the same purpose include, for example, 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4. -D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP , MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, ashlam, acetamide Acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicrabazone, amidosulfuron, amitrol (Amitrole), aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametrid
• hlorfenac chlorfenprop, chlorbufam, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chlormequat chloreturon, chloroxynil, chloroxuron, chloropon, saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat, diethamquat Diquat, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron, cyclopyrimorate, dichlorprop, dicroprop- P (dichlorprop-P), dichlobenil, dichlobenil, diclohop-methyl, dichlormate, dichlormate, dichloralurea, diquat, cisanilide, disul ), Siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoceb, dinoter
• biopesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and insect poxvirus (Entomopoxivirus).
• Virus preparations such as EPV, Monocrossporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans
• Bactericidal agents such as microbial pesticides used as insecticides, Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc. The same effect can be expected by using it in combination with a microbial pesticide used as a virus or a biopesticide used as a herbicide such as Xanthomonas campestris.
• biopesticides for example, Onshitsutsuyakobachi (Encarsia formosa), Koreman Aphidius colemani (Aphidius colemani), Cecidomyiidae (Aphidoletes aphidimyza), Isaea Himekobachi (Diglyphus isaea), Hamoglyphus isaea (Dacnusa) Natural enemy organisms such as Phytoseiulus persimilis, Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl-acetate, (E) Z) -4,10-Tetradecazineiel-acetate, (Z) -8-dodecenyl-acetate, (Z) -11-tetradecenyl-acetate, (Z) -13-ikos
• Preparation example 1 Compound represented by the general formula (I) of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 10 parts or more are uniformly mixed and dissolved to form an emulsion. To do.
• Preparation example 2 Compound represented by the general formula (I) of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts or more are uniformly mixed and pulverized to obtain a powder.
• Preparation example 3 Compound represented by the general formula (I) of the present invention 5 parts Bentonite and clay mixed powder 90 parts Calcium lignin sulfonate 5 parts or more are uniformly mixed, kneaded with an appropriate amount of water, granulated and dried. Use as granules.
• Preparation example 4 Compound represented by the general formula (I) of the present invention 20 parts Mixture of kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts or more are uniformly mixed and pulverized. Use as a wettable powder.
• Test example 1 Bactericidal effect test against soybean rust disease A pot containing a compound represented by the general formula (I) of the present invention prepared according to Preparation Examples 1 to 4 as an active ingredient and diluted with water to a predetermined concentration and having a diameter of 6 cm. Soybeans (variety: Enrei, 2 leaf stage) raised in seedlings were sprayed with foliage at a ratio of 10 ml per pot. After air-drying with a chemical solution, a spore suspension prepared from spores obtained from soybean leaves infected with soybean rust (Phakopsora pachyrhizi) is spray-injected, kept at 20 ° C. for 24 hours, and then transferred to a greenhouse for 10 hours. I left it around the day. For the evaluation, various diseased area ratios were assessed, and the control value was calculated from the following formula 1. (Equation 1)
• Control value is 9% or less 1: Control value is 10 to 19% 2: Control price is 20-29% 3: Control price is 30-39% 4: Control price is 40-49% 5: Control price is 50-59% 6: Control value is 60-69% 7: Control value is 70-79% 8: Control price is 80-89% 9: Control price is 90-99% 10: 100% control price
• the compound represented by the general formula (I) of the present invention or salts thereof has an excellent effect as a fungicide for agriculture and horticulture. Therefore, the present invention may contribute to the development of the agrochemical industry, agriculture, and related fields thereof.

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