Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D231/18—One oxygen or sulfur atom
• • 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
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
• • 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
  • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
• • 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
  • A01P13/00—Herbicides; Algicides
• • 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
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
  • A61K31/415—1,2-Diazoles
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
  • A61P31/04—Antibacterial agents
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
  • A61P31/10—Antimycotics
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/10—Anthelmintics
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
  • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
  • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

• the present invention relates to novel pyrazole compounds and salts thereof, intermediates for their production, and pest control agents containing the compounds and salts thereof as active ingredients.
• Patent Documents 1 and 2 disclose certain pyrazole compounds, they do not disclose anything regarding the pyrazole compound according to the present invention.
• Patent Documents 3 and 4 disclose that certain pyrazole compounds are useful as bactericidal agents, they do not disclose anything about the pyrazole compound according to the present invention.
• Patent Documents 5 to 8 disclose that certain heterocyclic compounds are useful as fungicides, but do not disclose anything about the pyrazole compound according to the present invention.
• a novel pyrazole compound represented by the following formula (1) according to the present invention is excellent as a fungicide, especially as an agricultural and horticultural fungicide.
• the present invention was completed based on the discovery that the plant exhibits a pesticidal activity.
• pyrazole compounds according to the present invention are not disclosed in any literature, and their usefulness as pest control agents is unknown.
• the present invention relates to the following [1].
• G represents G-1
• G-1 represents a structure represented by the following structural formula
• X 1 represents a halogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy
• R Y represents a hydrogen atom, a halogen atom, or a C 1 to C 6 alkyl
• R 1 represents a hydrogen atom or C 1 to C 6 alkyl
• R 2 represents a hydrogen atom or C 1 to C 6 alkyl
• R 5 represents a hydrogen atom or C 1 to C 6 alkyl
• R 6 represents a hydrogen atom or C 1 to C 6 alkyl
• r 1 represents an integer of 2
• two R 5 and two R 6 may be the same or different from each other
• R 7 represents C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl or phenyl
• R 8 represents a hydrogen atom or C 1 to C 6 alkyl
• R 9 represents a hydrogen atom or C 1 to C 6 alkyl
• Z represents Z-1, Z-2, Z-3, Z-4, Z-5, Z-6 or Z-7
• Z-1 to Z-7 each represent a structure represented by the following structural formula
• substitution position of Z 1 represents substitution on the aromatic ring of Z-1 to Z-7
• Z 1 is hydroxy, carboxy, amino, nitro, cyano, halogen atom, C 1 to C 6 alkyl, C 3 to C 10 cycloalkyl, C 1 to C 6 haloalkyl, C 3 to C 10 halocycloalkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylamino, C 1 -C 6 alkylcarbonyl , C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkyl substituted with R i , -OR d , -NHC(O)R e , -NR h C(O)R e , -NHSO 2 R i
• F-1 to F-15 each represent a structure represented by the following structural formula
• Z a is a halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylcarbonyl or C 1 -C represents 6 alkoxycarbonyl,
• v7 represents an integer of 2, 3, 4, 5, 6 or 7
• each Z a may be the same or different from each other
• v6 represents an integer of 2, 3, 4, 5 or 6
• each Z a may be the same or different from each other
• v5 represents an integer of 2, 3, 4 or 5
• each Z a may be the same or different from each other
• v4 represents an integer of 2, 3 or 4
• each Z a may be the same or different from each other
• v3 represents an integer of 2 or 3
• each Z a may be the same or different from each other
• v3 represents an integer of 2 or 3
• each Z a when
• the compound of the present invention represented by formula (1) exhibits excellent control activity against many pathogenic bacteria. Therefore, the present invention can provide a useful fungicide, particularly a fungicide for agriculture and horticulture.
• the compounds of the present invention may exist in E-form and Z-form geometric isomers; Includes mixtures containing Z-forms in arbitrary proportions.
• compounds having geometric isomers are represented as compounds having a wavy line bond, for example, as in formula (1-R a -6).
• the compounds of the present invention may have optically active forms due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, but the compounds of the present invention may have all optical activities. including racemic body or racemic body.
• the compounds of the present invention may have tautomers depending on the type of substituent, but the compounds of the present invention may include all tautomers or a mixture of tautomers in any proportion. include.
• the compound of the present invention may exist as one or more rotamers due to restricted bond rotation caused by steric hindrance between substituents; however, the compound of the present invention may exist as one or more rotamers. It includes rotamers or mixtures of diastereomers in any proportion.
• n- means normal
• i- means iso
• s- means secondary
• tert- means tertiary
• Ph means phenyl
• halogen atom includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• halo in this specification also represents these halogen atoms.
• C a -C b alkyl represents a linear or branched saturated hydrocarbon group having a to b carbon atoms.
• Examples of “C a - C b alkyl” include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl Specific examples include n-hexyl and n-hexyl.
• C a -C b alkyl is selected within the specified range of carbon atoms.
• C a - C b haloalkyl refers to a linear or branched chain consisting of a to b carbon atoms, in which the hydrogen atom bonded to the carbon atom is optionally substituted with a halogen atom. represents a saturated hydrocarbon group. When substituted by two or more halogen atoms, those halogen atoms may be the same or different from each other.
• C a - C b haloalkyl examples include fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2- Specific examples include fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl and 2,2,2-trichloroethyl. Examples include: “C a -C b haloalkyl” is selected within the specified range of carbon atoms.
• C a -C b alkenyl refers to a linear or branched chain consisting of a to b carbon atoms, and one or more double bonds in the molecule. represents an unsaturated hydrocarbon.
• Examples of “C a - C b alkenyl” include vinyl, 1-propenyl, 2-propenyl (hereinafter also referred to as allyl), 1-methylethenyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl Specific examples include -2-butenyl and 1,1-dimethyl-2-propenyl.
• C a -C b alkenyl is selected within the specified range of carbon atoms.
• C a -C b alkynyl refers to a linear or branched chain consisting of a to b carbon atoms, and having one or more triple bonds in the molecule. Represents an unsaturated hydrocarbon.
• Specific examples of “C a -C b alkynyl” include ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl and 1-hexynyl.
• C a -C b alkynyl is selected within the specified range of carbon atoms.
• C a -C b alkoxy represents alkyl-O-, which has the above meaning and has a to b carbon atoms.
• Examples of “C a - C b alkoxy” include methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, and 2-ethylhexyloxy.
• Examples include: "C a -C b alkoxy” is selected within the specified range of carbon atoms.
• C a -C b haloalkoxy represents haloalkyl-O-, which has the above meaning and has a to b carbon atoms.
• Examples of “C a - C b haloalkoxy” include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1, Specific examples include 1,2,2,-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy and 1,1,2,3,3,3-hexafluoropropyloxy.
• “C a -C b haloalkoxy” is selected within the specified number of carbon atoms.
• C a -C b alkenyloxy represents alkenyl-O-, which has the above meaning and has a to b carbon atoms.
• Examples of “C a - C b alkenyloxy” include vinyloxy, 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 2-butenyloxy, 2-methyl-2-propenyloxy, 3-methyl-2 Specific examples include -butenyloxy, 1,1-dimethyl-2-propenyloxy and the like.
• “C a -C b alkenyloxy” is selected within the specified number of carbon atoms.
• C a -C b alkylthio represents alkyl-S-, which has the above meaning and has a to b carbon atoms.
• Specific examples of "C a -C b alkylthio” include methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio and tert-butylthio.
• C a -C b alkylthio is selected within the specified range of carbon atoms.
• C a -C b alkylsulfinyl represents alkyl-S(O)-, which has the above meaning and has a to b carbon atoms.
• Examples of “C a - C b alkylsulfinyl” include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, S-butylsulfinyl, and tert-butylsulfinyl.
• a specific example is given.
• “C a -C b alkylsulfinyl” is selected within the specified number of carbon atoms.
• C a -C b alkylsulfonyl represents alkyl-SO 2 - having the above meaning of a to b carbon atoms.
• Examples of “C a - C b alkylsulfonyl” include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, and tert-butylsulfonyl.
• a specific example is given.
• “C a -C b alkylsulfonyl” is selected within the specified number of carbon atoms.
• C a -C b cycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms.
• C a -C b cycloalkyl can form, for example, a 3- to 10-membered monocyclic or composite ring structure.
• hydrogen in each ring may be optionally substituted with alkyl within the specified number of carbon atoms.
• Specific examples of “C a -C b cycloalkyl” include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
• C a -C b cycloalkyl is selected within the specified number of carbon atoms.
• C a - C b halocycloalkyl refers to a cyclic hydrocarbon group consisting of a to b carbon atoms, in which the hydrogen atom bonded to the carbon atom is optionally substituted with a halogen atom. represents. When substituted by two or more halogen atoms, those halogen atoms may be the same or different from each other.
• C a - C b halocycloalkyl examples include 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl, Specific examples include 2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl, and 2,2,3,3-tetrafluorocyclobutyl.
• C a -C b halocycloalkyl is selected within the specified range of carbon atoms.
• C a -C b alkylamino refers to amino in which one of the hydrogen atoms is substituted with alkyl having the above meaning and having a to b carbon atoms.
• Specific examples of “C a - C b alkylamino” include methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, and tert-butylamino. It will be done.
• “C a -C b alkylamino” is selected within the specified range of carbon atoms.
• di(C a - C b alkyl) amino refers to the above meaning in which both hydrogen atoms have a to b carbon atoms, which may be the same or different from each other. represents an amino substituted by an alkyl.
• Examples of "di(C a -C b alkyl)amino” include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, Specific examples include amino and di(n-butyl)amino.
• Each alkyl in "di(C a -C b alkyl)amino” is selected within the specified number of carbon atoms.
• C a -C b alkylcarbonyl represents alkyl-C(O)-, which has the above meaning and has a to b carbon atoms.
• Specific examples of “C a -C b alkylcarbonyl” include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl and heptanoyl.
• “C a -C b alkylcarbonyl” is selected within the specified range of carbon atoms.
• C a -C b alkoxycarbonyl represents alkyl-O-C(O)-, which has the above meaning and has a to b carbon atoms.
• Examples of "C a - C b alkylcarbonyl” include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl Specific examples include 2-ethylhexyloxycarbonyl and 2-ethylhexyloxycarbonyl.
• “C a -C b alkylcarbonyl” is selected within the specified range of carbon atoms.
• C a -C b alkylaminocarbonyl represents carbamoyl in which one of the hydrogen atoms is substituted with alkyl having the above meaning and having a to b carbon atoms.
• Examples of “C a - C b alkylaminocarbonyl” include methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, s-butylcarbamoyl and tert-butylcarbamoyl. etc. are given as specific examples.
• “C a -C b alkylaminocarbonyl” is selected within the specified range of carbon atoms.
• C a -C b cycloalkylaminocarbonyl in the present specification represents carbamoyl in which one of the hydrogen atoms is substituted with cycloalkyl having the above meaning of a to b carbon atoms.
• Specific examples of "C a - C b cycloalkylaminocarbonyl” include cyclopropylcarbamoyl, cyclobutylcarbamoyl, cyclopentylcarbamoyl, and cyclohexylcarbamoyl.
• C a -C b cycloalkylaminocarbonyl is selected within the specified range of carbon atoms.
• di(C a -C b )alkylaminocarbonyl refers to the above-mentioned compound in which both hydrogen atoms have a to b carbon atoms, which may be the same or different from each other. represents carbamoyl substituted by alkyl with the meaning.
• di(C a -C b )alkylaminocarbonyl examples include N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N,N-di(n- Examples include propyl)carbamoyl and N,N-di(n-butyl)carbamoyl.
• Each alkyl in "di(C a -C b )alkylaminocarbonyl" is selected within the specified number of carbon atoms.
• tri(C a -C b )alkylsilyl refers to alkyl substituted with alkyl having the above meaning and having a to b carbon atoms, which may be the same or different from each other. represents Cyril.
• Specific examples of "tri(C a - C b ) alkylsilyl” include trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethyl Examples include silyl and tert-butyldimethylsilyl.
• Each alkyl in "tri(C a -C b )alkylsilyl” is selected within the specified number of carbon atoms.
• C a -C b alkyl substituted with R c is the above alkyl having a to b carbon atoms, in which any hydrogen atom bonded to the alkyl carbon atom is partially or completely substituted with one or more substituents R c , R i or R 10 represents an alkyl meaning. Each of these is selected within a specified range of carbon atoms. When two or more substituents R c , R i or R 10 are present, the substituents R c , R i or R 10 may be the same or different from each other.
• C a -C b alkoxy substituted with R b means that any hydrogen atom bonded to a carbon atom is partially or completely substituted with one or more substituents R b . represents alkoxy having the above meaning and having a to b carbon atoms. “C a -C b alkoxy substituted with R b ” is selected within the specified number of carbon atoms. When two or more substituents R b are present, the substituents R b may be the same or different from each other.
• benzyl herein represents -CH 2 C 6 H 5 .
• benzyloxy herein represents -O-CH 2 C 6 H 5 .
• the compound of the present invention represented by formula (1) can be produced, for example, by the following method. Note that the following explanation is merely an example, and the compound of the present invention represented by formula (1) may be produced by other methods.
• the “compound of the present invention represented by formula (1)” is also referred to as “compound (1)”
• the “compound represented by formula (2)” is also referred to as “compound (2)”. be written. Other compounds are also described in the same manner.
• Compound (1) of the present invention can be produced, for example, by the following production method.
• Compound (1) is a combination of compound (1-1) and compound (1-a) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, sulfur). It is produced by reacting a dehydration condensation agent (acid acid salt or para-toluene sulfonate salt, etc.) with a dehydration condensation agent in a solvent or without a solvent, and in some cases in the presence of a base and/or an additive. be able to.
• a dehydration condensation agent as acid salt or para-toluene sulfonate salt, etc.
• the amount of compound (1-a) or its salt and dehydration condensation agent used may be 0.5 to 50 equivalents per equivalent of compound (1-1).
• dehydration condensation agent examples include 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N'-dicyclohexylcarbodiimide, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. salts, and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate.
• the solvent used may be inert to the reaction, and examples of the solvent include water; alcoholic solvents such as methanol, ethanol, or tert-butyl alcohol; diethyl ether, tetrahydrofuran, and 1,4-dioxane.
• 1,2-dimethoxyethane or diglyme 1,2-dimethoxyethane or diglyme
• aromatic hydrocarbon solvents such as benzene, xylene or toluene
• aliphatic hydrocarbon solvents such as n-pentane, n-hexane or cyclohexane
• Halogenated hydrocarbon solvents such as 2-dichloroethane
• nitrile solvents such as acetonitrile or propionitrile
• amide solvent dimethyl sulfoxide; pyridine; or a mixed solvent thereof; and the like.
• the reaction can be carried out in the presence of a base.
• bases that can be used include pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2 ] an organic base such as octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) or 1,5-diazabicyclo[4.3.0]-5-nonene (DBN); Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium bicarbonate, potassium carbonate, cesium carbonate or potassium phosphate; metal alkoxides such as sodium methoxide, sodium ethoxide or potassium tert-butoxide; .
• the amount of the base used may be 0.1 to 100 equivalents per 1 equivalent of compound (1-1).
• the reaction can be carried out in the presence of additives.
• additives examples include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, and 4-(dimethylamino)pyridine.
• the amount of the additive used may be 0.005 to 100 equivalents per 1 equivalent of compound (1-1).
• the reaction temperature can be set at any temperature from -78°C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate or the reaction temperature, but is usually within the range of 5 minutes to 100 hours. Can be set to
• Compound (2) of the present invention can be produced, for example, by the following production method.
• L is a chlorine atom, a bromine atom, an iodine atom, C 1 -C 4 alkylsulfonyloxy (e.g., methanesulfonyloxy, etc.), halosulfonyloxy (e.g., fluorosulfonyloxy, etc.), C 1 -C 4 haloalkyl represents a leaving group such as sulfonyloxy (for example, trifluoromethanesulfonyloxy, etc.) or arylsulfonyloxy (for example, paratoluenesulfonyloxy, etc.), and R Xa is C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, represents C 1 -C 6 alkyl or benzyl substituted with R c , G, T, R Y , R 1 , R 2 , R
• Compound (2) can be produced by reacting compound (2-1) and compound (D) in a solvent or without a solvent, optionally in the presence of a base.
• the amount of compound (D) used may be 0.5 to 50 equivalents per 1 equivalent of compound (2-1).
• compound (D) Some of the compounds represented by compound (D) are known compounds and are available as commercial products. Further, other compounds represented by compound (D) can also be produced according to general synthesis methods for known compounds described in literature.
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• Examples of the base that can be used in this reaction include the bases exemplified in Production Example 1.
• the amount of the base used may be 0.1 to 100 equivalents per 1 equivalent of compound (2-1).
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• Compound (5) or compound (6) can be produced by reacting the compound (4) of the present invention and an oxidizing agent in a solvent or without a solvent.
• oxidizing agent examples include hydrogen peroxide and metachloroperbenzoic acid.
• the amount of the oxidizing agent used may be 0.1 to 100 equivalents per equivalent of compound (4).
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• R 1a represents C 1 to C 6 alkyl, and G, L , T , R . ]
• Compound (8) can be produced by reacting compound (7) of the present invention and compound (D1) in a solvent or without a solvent, optionally in the presence of a base.
• the amount of compound (D1) to be used may be 0.5 to 50 equivalents per 1 equivalent of compound (7).
• compound (D1) Some of the compounds represented by compound (D1) are known compounds and are available as commercial products. Further, other compounds represented by compound (D1) can also be produced according to general synthesis methods for known compounds described in literature.
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1.
• the amount of the base used may be 0.1 to 100 equivalents per 1 equivalent of compound (7).
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• Compound (10) of the present invention can be produced, for example, by the following production method.
• Compound (10) is a combination of compound (9) of the present invention and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide (hereinafter also referred to as "Lawson's reagent"). (described below) in a solvent or without a solvent, and optionally in the presence of a base.
• Lawson's reagent 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide
• the amount of Lawson's reagent used may be 0.5 to 50 equivalents per 1 equivalent of compound (9).
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• Compound (9) can be synthesized according to the method of Production Example 1.
• Compound (12) of the present invention can be produced, for example, by the following production method.
• R d1 represents C 1 to C 6 alkyl or R d
• G, L, T, R X , R Y , R 2 , R 3 , R 4 , R a , R d and p are express the same meaning.
• Compound (12) can be produced by reacting compound (11) of the present invention and compound (D2) in a solvent or without a solvent, optionally in the presence of a base.
• the amount of compound (D2) used may be 0.5 to 50 equivalents per 1 equivalent of compound (11).
• compound (D2) Some of the compounds represented by compound (D2) are known compounds and are available as commercial products. Further, other compounds represented by compound (D2) can also be produced according to general methods for synthesizing known compounds described in literature.
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1.
• the amount of the base used may be 0.1 to 100 equivalents per 1 equivalent of compound (11).
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• Compound (11) can be synthesized according to the method of Production Example 1.
• L 1 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, or a C 1 -C 4 alkylcarbonyloxy (e.g., acetoxy)
• L 2 represents a chlorine atom, a bromine atom, an iodine atom , C 1 -C 4 alkylsulfonyloxy (for example, methanesulfonyloxy, etc.), halosulfonyloxy (for example, fluorosulfonyloxy, etc.), C 1 -C 4 haloalkylsulfonyloxy (for example, trifluoromethanesulfonyloxy, etc.), or arylsulfonyl represents a leaving group such as oxy (for example, para-toluenesulfonyloxy), and G, T, R X , R Y , R 2 , R 3 , R 4 , R
• Compound (14) or compound (15) can be obtained by reacting the compound (13) of the present invention with compound (E) or compound (F) in a solvent or without a solvent, optionally in the presence of a base. It can be manufactured in
• the amount of compound (E) or compound (F) used may be 0.5 to 50 equivalents per 1 equivalent of compound (13).
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1.
• the amount of the base used may be 0.1 to 100 equivalents per 1 equivalent of compound (13).
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• Compound (13) can be synthesized according to the method of Production Example 1.
• Compound (1-1) used in Production Example 1 can be produced, for example, according to the production route (reaction route) shown in Reaction Formula 1 below.
• X represents a halogen atom
• G, T, R X and R Y represent the same meanings as above.
• Compound (1-1) is prepared by combining compound (1-2) and compound (A) in a solvent or without a solvent, in the presence of a base, and optionally with one of a copper catalyst and an additive, or It can be obtained by reacting in the presence of both.
• compound (1-1) can be obtained by reacting compound (1-2) and compound (A) in the presence of a base, optionally in the presence of a palladium catalyst and a ligand. can.
• the amount of compound (A) used may be 0.5 to 50 equivalents per 1 equivalent of compound (1-2).
• compound (A) Some of the compounds represented by compound (A) are known compounds and are available as commercial products. Further, other compounds represented by compound (A) can also be produced according to general synthesis methods for known compounds described in literature.
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• the reaction can be carried out in the presence of a base.
• a base examples include the bases exemplified in Production Example 1.
• the amount of the base used may be 0.1 to 100 equivalents per 1 equivalent of compound (1-2).
• the reaction can be carried out in the presence of a copper catalyst.
• the copper catalyst that can be used include copper iodide (monovalent), copper trifluoromethanesulfonate (monovalent) benzene complex, copper trifluoromethanesulfonate (monovalent) toluene complex, and the like.
• the amount of the copper catalyst used may be 0.001 to 50 equivalents per equivalent of compound (1-2).
• the reaction can be carried out in the presence of additives.
• additives examples include N,N-dimethylglycine and 4-(dimethylamino)pyridine.
• the amount of the additive used may be 0.001 to 100 equivalents per equivalent of compound (1-2).
• the reaction can be carried out in the presence of a palladium catalyst.
• palladium catalysts examples include palladium (bivalent) ( ⁇ -cinnamyl) chloride (dimer) and allylpalladium (divalent) chloride (dimer).
• the amount of palladium catalyst used may be 0.001 to 50 equivalents per equivalent of compound (1-2).
• the reaction can be carried out in the presence of a ligand.
• ligands examples include 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tert-butyl-XPhos), tetramethyl-di-tert-butyl Phosphino-2',4',6'-triisopropylbiphenyl (tetramethyldi-tert-butyl-XPhos), 2-di-(tert-butyl)phosphino-2',4',6'-triisopropyl-3- Examples include methoxy-6-methylbiphenyl (R GmbHckPhos) and 2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl (BrettPhos).
• the amount of the ligand used may be 0.001 to 50
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• compounds (1-1-1) in which T is an oxygen atom and R Y is a hydrogen atom are produced, for example, according to the production route (reaction route) shown in the following reaction formula. be able to.
• R 101 represents C 1 to C 6 alkyl, and G and R X have the same meanings as above. ]
• Step 1 Compound (1-3) is compound (1-4) and compound (B) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate or para-toluenesulfonate) in a solvent or without a solvent, optionally in the presence of a base.
• a salt thereof e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate or para-toluenesulfonate
• the amount of compound (B) or a salt thereof to be used may be 0.5 to 50 equivalents relative to 1 equivalent of compound (1-4).
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• the reaction can be carried out in the presence of a base.
• a base examples include the bases exemplified in Production Example 1.
• the amount of the base used may be 0.1 to 100 equivalents per 1 equivalent of compound (1-4).
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• Step 2 Compound (1-1-1) can be obtained by reacting compound (1-3) and an oxidizing agent in a solvent or without a solvent.
• oxidizing agents examples include potassium permanganate.
• the amount of the oxidizing agent used may be 0.1 to 100 equivalents per equivalent of compound (1-3).
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• compounds (1-1-1) in which T is an oxygen atom and R Y is a hydrogen atom are produced, for example, according to the production route (reaction route) shown in the following reaction formula. be able to.
• Step 1 Compound (1-5) can be obtained by reacting compound (1-6) under the same conditions as in step 1 in reaction formula 2.
• Step 2 Compound (1-1-1) can be obtained by reacting compound (1-5) and carbon dioxide in the presence of a base in a solvent or without a solvent.
• Examples of the base that can be used include n-butyllithium.
• the amount of the base used may be 0.1 to 100 equivalents per 1 equivalent of compound (1-5).
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• Step 1 Compound (1-a'-2) is prepared by combining compound (1-a'-1) and compound (C1) or compound (C2) in a solvent or without a solvent, in some cases in the presence of a base. , can be produced by reacting in the presence of a phase transfer catalyst, if necessary.
• compound (C1) or compound (C2) are known compounds and are available as commercial products. Further, other compounds represented by compound (C1) or compound (C2) can also be produced according to general synthesis methods for known compounds described in literature.
• the amount of compound (C1) or compound (C2) used may be 0.5 to 50 equivalents relative to 1 equivalent of compound (1-a'-1).
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• the reaction can be carried out in the presence of a base.
• a base examples include the bases exemplified in Production Example 1.
• the amount of the base used may be 0.1 to 100 equivalents per equivalent of compound (1-a'-1).
• phase transfer catalyst examples include quaternary ammonium salts such as tetrabutylammonium bromide.
• the amount of the phase transfer catalyst used may be 0.001 to 10 equivalents relative to 1 equivalent of compound (1-a'-1).
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• Step 2 Compound (1-a') or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, or para-toluenesulfonate, etc.) ) can be produced by reacting compound (1-a'-2) and an acid in a solvent or without a solvent.
• a salt thereof e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, or para-toluenesulfonate, etc.
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• the reaction can be carried out in the presence of an acid.
• acids that can be used include hydrochloric acid, sulfuric acid, acetic acid, and trifluoroacetic acid.
• the amount of acid used may be 0.5 to 1000 equivalents per equivalent of compound (1-a'-2).
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• Compound (2-1) used in Production Example 2 can be produced, for example, according to the production route (reaction route) shown in Reaction Formula 5 below.
• Compound (2-1) can be produced by reacting the compound (3) of the present invention with an acid in a solvent or without a solvent.
• the solvent used only needs to be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
• acids that can be used in the reaction include acids such as hydrochloric acid, sulfuric acid, formic acid, and trifluoroacetic acid.
• the amount of acid used may be 0.1 to 100 equivalents per equivalent of compound (3).
• the reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
• Compound (3) can be synthesized according to the method of Production Method 1.
• the compounds of the present invention are generally used as agricultural and horticultural bactericides and fungicides to combat various diseases caused by Nephromycetes, Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, bacteria, or viruses. It can be used against.
• Phathogen means a microorganism that causes plant diseases, and specifically includes, but is not limited to, the following microorganisms.
• Taphrina spp. e.g., Taphrina deformans, T. pruni, etc.
• Pneumocystis spp. Geotrichum spp.
• Candida spp. e.g., Candida albicans, C. sorbosa, etc.
• Pichia spp. e.g., Pichia kluyveri, etc.
• Capnodium spp. Fumago spp.
• Hypocapnodium spp. Cercospora spp. (e.g. Cercospora apii, C. asparagi, C. beticola, C. capsici, C. carotae, C. kaki, C.
• kikuchii C. zonata, etc.
• Cercosporidium spp. Cladosporium spp. (e.g., Cladosporium colocasiae, C. cucumerinum, C. variabile, etc.), Davidiella spp., Didymosporium spp., Heterosporium spp. (e.g., Heterosporium allii, etc.), Mycosphaerella spp. (e.g., Mycosphaerella arachidis) , M. berkeleyi, M. cerasella, M. fijiensis, M. fragariae, M. graminicola, M. nawae, M. pinodes, M.
• pomi, M. zingiberis, etc. Mycovellosiella spp. (e.g., Mycovellosiella fulva, M. nattrassii etc.), Paracercospora spp. (e.g. Paracercospora egenula etc.), Phaeoisariopsis spp., Phaeoramularia spp., Pseudocercospora spp. (e.g. Pseudocercospora abelmoschi, P. fuligena, P. vitis etc.), Pseudocercosporella spp.
• Mycovellosiella spp. e.g., Mycovellosiella fulva, M. nattrassii etc.
• Paracercospora spp. e.g. Paracercospora egenula etc.
• Phaeoisariopsis spp. Phaeoramularia s
• Ramichloridium spp. Ramularia spp., Septogloeum spp., Septoria spp. (e.g., Septoria albopunctata, S. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (e.g. Elsinoe ampelina, E. araliae, E. fawcettii etc.), Sphaceloma spp.
• Ramichloridium spp. Ramularia spp.
• Septogloeum spp. Septoria spp.
• Septoria spp. e.g., Septoria albopunctata, S. apiicola, S.
• Ascochyta spp. e.g. Ascochyta pisi (e.g., Corynespora cassiicola, etc.), Leptosphaeria spp. (e.g., Leptosphaeria coniothyrium, L. maculans, etc.), Saccharicola spp., Phaeosphaeria spp. (e.g., Phaeosphaeria nodorum, etc.), Ophiosphaerella spp., Setophoma spp. ., Helminthosporium spp., Alternaria spp. (e.g.
• Alternaria alternata A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A. panax , A. porri, A. radicina, A. solani etc.
• Bipolaris spp. e.g. Bipolaris sorghicola etc.
• Cochliobolus spp. e.g. Cochliobolus heterostrophus, C. lunatus, C. miyabeanus etc.
• Curvularia spp. e.g. , Curvularia geniculata, C.
• Drechslera spp. Pleospora spp. (e.g., Pleospora herbarum, etc.), Pyrenophora spp. (e.g., Pyrenophora graminea, P. teres, etc.), Setosphaeria spp. (e.g., Setosphaeria turcica, etc.) , Stemphylium spp. (e.g., Stemphylium botryosum, S. lycopersici, S. solani, S. vesicarium, etc.), Fusicladium spp., Venturia spp. (e.g., Venturia carpophila, V.
• Pleospora spp. e.g., Pleospora herbarum, etc.
• Pyrenophora spp. e.g., Pyrenophora graminea, P. teres, etc.
• Setosphaeria spp. e
• Didymella spp. e.g. Didymella bryoniae, D. fabae etc.
• Hendersonia spp. Phoma spp. (e.g. Phoma erratica var. mikan, P. exigua var. exigua, P. wasabiae etc.)
• Pyrenochaeta spp. e.g. , Pyrenochaeta lycopersici, etc.
• Stagonospora spp. e.g., Stagonospora sacchari, etc.
• Phyllosticta spp. e.g., Botryosphaeria berengeriana f. sp. piricola, B. dothidea, etc.
• Dothiorella spp. Fusicoccum spp., Guignardia spp., Lasiodiplodia (e.g. Lasiodiplodia theobromae, etc.), Macrophoma spp., Macrophomina spp., Neofusicoccum spp., Phyllosticta spp. (e.g., Phyllosticta zingiberis, etc.), Schizothyrium spp.
• spp. e.g., Schizothyrium pomi, etc.
• Acrospermum spp. Leptosphaerulina spp. ., Aspergillus spp.
• Penicillium spp. e.g. Penicillium digitatum, P. italicum, P. sclerotigenum, etc.
• Microsporum spp. Trichophyton spp. (e.g. Trichophyton mentagrophytes, T. rubrum, etc.), Histoplasma spp.
• Blumeria spp. e.g., Blumeria graminis f. sp. hordei, B. g. f. sp.
• Erysiphe spp. e.g., Erysiphe betae, E. cichoracearum, E. c. var. cichoracearum, E. heraclei, E. pisi, etc.
• Golovinomyces spp. e.g., Golovinomyces cichoracearum var. latisporus, etc.
• Leveillula spp. e.g., Leveillula taurica, etc.
• Microsphaera spp. Oidium spp. (e.g., Oidium neolycopersici, etc.), Phyllactinia spp.
• Podosphaera spp. e.g., Podosphaera fusca, P. leucotricha, P. pannosa, P. tridactyla var. tridactyla, P. xanthii, etc.
• Sphaerotheca spp. e.g., Sphaerotheca aphanis var aphanis, S. fuliginea, etc.
• Uncinula spp. e.g., Uncinula necator, U. n. var. necator, etc.
• Botryotinia spp. e.g., Botryotinia fuckeliana, etc.
• Botrytis spp. e.g., Botrytis allii, B. byssoidea, B. cinerea, B. elliptica, B. fabae, B. squamosa, etc.
• Ciborinia spp. Grovesinia spp., Monilia mumecola, Monilinia spp. (e.g. Monilinia fructicola, M. fructigena, M. laxa, M. mali, M.
• Sclerotinia spp. e.g., Sclerotinia borealis, S. homoeocarpa, S. minor, S. sclerotiorum, etc.
• Valdensia spp. e.g., Valdensia heterodoxa, etc.
• Claviceps spp. e.g., Claviceps sorghi, C. sorghicola
• Epichloe spp. Ephelis japonica, Villosiclava virens
• Hypomyces spp. e.g., Hypomyces solani f. sp. mori, H. s. f. sp.
• Trichoderma spp. e.g., Trichoderma viride, etc.
• Calonectria spp. e.g. Calonectria ilicicola etc.
• Candelospora spp. Cylindrocarpon spp.
• Cylindrocladium spp. Fusarium spp. (e.g. Fusarium arthrosporioides, F. crookwellense, F. culmorum, F. cuneirostrum, F. oxysporum, F. o. f. sp. adzukicola, F. o. f. sp. allii, F. o. f. sp.
• Gibberella spp. Gibberella avenacea, G. baccata, G. fujikuroi, G. zeae, etc.
• Haematonectria spp. Nectria spp., Ophionectria spp., Caldariomyces spp., Myrothecium spp., Trichothecium spp., Verticillium spp. albo-atrum, V. dahliae, V.
• Ceratocystis spp. e.g., Ceratocystis ficicola, C. fimbriata, etc.
• Thielaviopsis spp. e.g., Thielaviopsis basicola, etc.
• Adisciso spp. Monochaetia spp.
• Pestalotia spp. e.g., Pestalotia eriobotrifolia, etc.
• Pestalotiopsis spp. e.g., Pestalotiopsis funerea, P. longiseta, P. neglecta, P.
• Physalospora spp. Nemania spp., Nodulisporium spp., Roselinia spp. (e.g., Rosellinia necatrix, etc.), Monographella spp. (e.g., Monographella nivalis, etc.), Ophiostoma spp., Cryphonectria spp. (e.g., Cryphonectria parasitica, etc.), Diaporthe spp. (e.g., Diaporthe citri, D. kyushuensis, D. nomurai, D. tanakae, etc.), Diaporthopsis spp., Phomopsis spp.
• Cryptosporella spp. e.g., Phomopsis asparagi, P. fukushii, P. obscurans, P. vexans, etc.
• Cryptosporella spp. e.g., Phomopsis asparagi, P. fukushii, P. obscurans, P. vexans, etc.
• Cryptosporella spp. e.g., Discula theae-sinensis, etc.
• Gnomonia spp. . Coniella spp., Coryneum spp., Greeneria spp., Melanconis spp., Cytospora spp., Leucostoma spp., Valsa spp. (e.g.,
• Valsa ceratosperma etc. Tubakia spp., Monosporascus spp., Clasterosporium spp., Gaeumannomyces (e.g., Gaeumannomyces graminis, etc.), Magnaporthe spp. (e.g., Magnaporthe grisea, etc.), Pyricularia spp. (e.g., Pyricularia zingiberis, etc.), Monilochaetes infuscans, Colletotrichum spp. (e.g., Colletotrichum acutatum, C. capsici, C. cereale, C. destructivum, C. fragariae, C.
• Colletotrichum spp. e.g., Colletotrichum acutatum, C. capsici, C. cereale, C. destructivum, C. fragariae, C.
• Glomerella spp. e.g., Glomerella cingulata, etc.
• Khuskaia oryzae e.g., Phyllachora spp.
• Ellisembia spp. Briosia spp.
• Cephalosporium spp. e.g., Cephalosporium gramineum, etc.
• Epicoccum spp. Gloeocercospora sorghi, Mycocentrospora spp., Peltaster spp.
• Helicobasidium spp. e.g., Helicobasidium longisporum, etc.
• Coleosporium spp. e.g., Coleosporium plectranthi, etc.
• Cronaartium spp. Phakopsora spp. (e.g., Phakopsora artemisiae, etc.) P. nishidana, P. pachyrhizi, etc.)
• Physopella spp. e.g., Physopella ampelopsidis, etc.
• Kuehneola spp. e.g., Kuehneola japonica, etc.
• Gymnosporangium spp. e.g., Gymnosporangium asiaticum, G. yamadae, etc.
• Puccinia spp. e.g., Puccinia allii, P. brachypodii var. poae-nemoralis, P. coronata, P. c. var. coronata, P. cynodontis, P. graminis, P. g. subsp. graminicola, P. hordei, P. horiana, P.
• Uromyces spp. e.g., Uromyces phaseoli var. azukicola, U. p. var. phaseoli, Uromyces viciae-fabae var. viciae-fabae, etc.
• Naohidemyces vaccinii Nyssopsora spp., Leucotelium spp. , Tranzschelia spp.
• Tranzschelia discolor, etc. Aecidium spp., Blastospora spp. (e.g., Blastospora smilacis, etc.), Uredo spp., Sphacelotheca spp., Urocystis spp., Sporisorium spp. (e.g., Sporisorium scitamineum, etc.), Ustilago spp. (e.g. Ustilago maydis, U. nuda etc.), Entyloma spp., Exobasidium spp. (e.g. Exobasidium reticulatum, E.
• Exobasidium spp. e.g. Exobasidium reticulatum, E.
• Tilletia spp. e.g. Tilletia caries, T. controversa , T. laevis, etc.
• Itersonilia spp. e.g., Itersonilia perplexans, etc.
• Cryptococcus spp. Bovista spp. (e.g., Bovista dermoxantha, etc.)
• Lycoperdon spp. e.g., Lycoperdon curtisii, L. perlatum, etc.
• Conocybe spp. e.g., Conocybe apala, etc.
• Athelia spp. e.g., Athelia rolfsii, etc.
• Fungi of the phylum Blastocladiomycota such as Physoderma spp. Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis, etc.), Rhizopus spp. (e.g., Rhizopus arrhizus, R. chinensis, R. oryzae, R. stolonifer var. ) fungi.
• Protists of the phylum Cercozoa such as Plasmodiophora spp. (e.g. Plasmodiophora brassicae), Spongospora subterranea f. sp.
• Aphanomyces spp. e.g., Aphanomyces cochlioides, A. raphani, etc.
• Albugo spp. e.g., Albugo macrospora, A. wasabiae, etc.
• Bremia spp. e.g., Bremia lactucae, etc.
• Hyalopronospora spp. Peronosclerospora spp.
• Peronospora spp. e.g., Peronospora alliariae-wasabi, P. chrysanthemi-coronarii, P. destructor, P. farinosa f. sp. spinaciae, P.
• Plasmopara spp. e.g., Plasmopara halstedii, P. nivea, P. viticola, etc.
• Pseudoperonospora spp. e.g., Pseudoperonospora cubensis, etc.
• Sclerophthora spp. e.g., Phytophthora cactorum, P. capsici, P. citricola, P. citrophthora, P. cryptogea, P. fragariae, P. infestans, P. melonis, P.
• nicotianae P. palmivora, P. porri, P. sojae, P. syringae, P. vignae f. sp. adzukicola, etc.
• Pythium spp. e.g. , P. afertile, P. aphanidermatum, P. apleroticum, P. aristosporum, P. arrhenomanes, P. buismaniae, P. debaryanum, P. graminicola, P. horinouchiense, P. irregulare, P. iwayamai, P. myriotylum, P. okanoganense, P. paddicum, P. paroecandrum, P.
• P. afertile P. aphanidermatum, P. apleroticum, P. aristosporum, P. arrhenomanes, P. buismaniae, P. debaryanum, P. gramini
• Gram-positive fungi Gram-positive fungi of the phylum Firmicutes such as Clostridium sp. Gram-positive fungi of the phylum Tenericutes, such as Phytoplasma. Rhizobium spp. (e.g. Rhizobium radiobacter etc.), Acetobacter spp., Burkholderia spp. (e.g. Burkholderia andropogonis, B. cepacia, B. gladioli, B. glumae, B. plantarii etc.), Acidovorax spp. (e.g. Acidovorax avenae) subsp.
• Rhizobium spp. e.g. Rhizobium radiobacter etc.
• Acetobacter spp. e.g. Burkholderia andropogonis, B. cepacia, B. gladioli, B. glumae, B. plantarii etc.
• Acidovorax spp.
• avenae A. a. subsp. citrulli, A. konjaci, etc.
• Herbaspirillum spp. Ralstonia spp. (e.g., Ralstonia solanacearum, etc.)
• Xanthomonas spp. e.g., Xanthomonas albilineans, X. arboricola pv. pruni, X axonopodis pv. vitians, X. campestris pv. campestris, X. c. pv. cucurbitae, X. c. pv. glycines, X. c. pv.
• plant diseases caused by infection and proliferation of these pathogenic bacteria include, but are not limited to, the following plant diseases.
• Leaf curl (Taphrina deformans), Plum pockets (Taphrina pruni), Leaf spot (Cercospora asparagi), Cercospora leaf spot (Cercospora beticola), Frogeye leaf spot (Cercospora capsici), Angular leaf spot (Cercospora kaki), Purple stain (Cercospora kikuchii), Brown Leaf spot (Mycosphaerella arachidis), Cylindrosporium leaf spot ( Mycosphaerella cerasella, Blumeriella jaapii), Black sigatoka (Mycosphaerella fijiensis), Yellow sigatoka (Mycosphaerell musicola), Speckled leaf blotch (Mycosphaerella graminicola), Circular leaf spot ( Mycosphaerella nawae), Mycosphaerella blight (Mycosphaerella pinodes), Leaf spot (Mycosphaerella zingiberis), Leaf mold (Mycov
• cucumber powdery mildew (Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii), eggplant powdery mildew (Erysiphe cichoracearum, Leveillula) taurica, Sphaerotheca fuliginea), carrot and parsley powdery mildew (Erysiphe heraclei), pea powdery mildew (Erysiphe pisi), tomato powdery mildew (Leveillula taurica, Oidium neolycopersici, Oidium sp.), green pepper powdery mildew (Leveillula taurica) ), pumpkin powdery mildew (Oidium sp., Podosphaera xanthii), bitter melon powdery mildew (Oidium sp.), oyster powdery mildew (Phyllactinia kakicola), burdock powdery mildew (Phyllact
• simulans U. s. var. tandae
• powdery mildew of zucchini green melon
• Podosphaera xanthii powdery mildew of strawberries
• powdery mildew of strawberries Sphaerotheca aphanis var. aphanis
• watermelon Melon powdery mildew
• Grape powdery mildew Uncinula necator, U. n. var.
• Botrytis blight Botrytis cinerea
• Leaf blight Botrytis cinerea, B. byssoidea, B. squamosa
• Chocolate spot Botrytis cinerea, B. elliptica, B. fabae
• Brown rot Monilinia fructicola, M. fructigena, M.
• Blossom blight (Monilinia mali), Dollar spot (Sclerotinia homoeocarpa), Sclerotinia rot, Stem rot (Sclerotinia sclerotiorum), Rice mildew False smut (Villosiclava virens), Soybean black root rot (Calonectria ilicicola), Wheat Fusarium blight (Fusarium crookwellense, F. culmorum, Gibberella avenacea, G. zeae, Monographella nivalis), Fusarium blight (Fusarium culmorum, Gibberella avenacea, G.
• Endothia canker (Cryphonectria parasitica), Melanose (Diaporthe citri), Asparagus stem blight (Phomopsis asparagi), Phomopsis canker (Phomopsis fukushii), Brown spot (Phomopsis vexans), Tea anthracnose (Discula theae-sinensis), Valsa canker (Valsa ceratosperma), Rice blast disease Blast (Magnaporthe grisea), Strawberry anthracnose Crown rot (Colletotrichum acutatum, C.
• Bacterial fruit blotch (Acidovorax avenae subsp. citrulli), Bacterial leaf blight (Acidovorax konjaci), Bacterial wilt (Ralstonia solanacearum), Bacterial shot hole (Xanthomonas arboricola pv. pruni) , Pseudomonas syringae pv. syringae, Brenneria nigrifluens), Bacterial leaf spot (Xanthomonas arboricola pv. pruni), Bacterial leaf spot (Xanthomonas axonopodis pv.
• Bacterial black spot (Pseudomonas syringae pv. maculicola), Bacterial canker (Pseudomonas) syringae pv. morsprunorum, Erwinia sp.), Bacterial shoot blight (Pseudomonas syringae pv. theae), Bacterial soft rot (Dickeya sp., Pectobacterium carotovorum), Fire blight in the Rosaceae family, Pectobacterium subfamily. (Erwinia amylovora), Soft rot (Pectobacterium carotovorum), Bacterial soft rot (Pectobacterium carotovorum).
• control agents for diseases of agricultural and horticultural crops has progressed, and a wide variety of agents have been put into practical use to date.
• pathogenic bacteria have acquired drug resistance, and there have been an increasing number of cases in which pathogenic bacteria have become difficult to control with conventionally used existing fungicides.
• the problem of some of the existing drugs being highly toxic and remaining in the environment for a long time, disturbing the ecosystem, is becoming apparent.
• the compounds of the present invention have excellent control activity against many pathogenic bacteria and are highly safe for target crops.
• the compounds of the present invention can exhibit sufficient control effects against pathogenic bacteria that have acquired resistance to existing fungicides.
• the compounds of the present invention do not cause phytotoxicity to target crops, have almost no adverse effects on mammals, fish, and beneficial insects, have low persistence, and have a light burden on the environment.
• the compounds of the present invention are also useful as medical antibacterial agents and veterinary antibacterial agents that are used as antifungal agents or endoparasite control agents, wood, paper/pulp, adhesives, and paints. It can also be used as an antibacterial and antifungal agent for textiles and leather, and as an industrial disinfectant for cooling waterways in manufacturing plants.
• pathogenic bacteria examples include Trichophyton fungi such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida fungi such as Candida albicans, Aspergillus fungi such as Aspergillus fumigatus, and Cryptococcus fungi such as Cryptococcus neoformas.
• Trichophyton fungi such as Trichophyton rubrum and Trichophyton mentagrophytes
• Candida fungi such as Candida albicans
• Aspergillus fungi such as Aspergillus fumigatus
• Cryptococcus fungi such as Cryptococcus neoformas.
• Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa and Haemophilus influenzae
• Gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes, etc. These include, but are not limited to.
• Examples of bacterial strains that can be used as antibacterial and fungicidal agents include wood-decaying fungi such as Tyromyces palustris and Coriolus versicolor, Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, Cladosporium cladosporioides, and Aureobasidium pullulans. , Gliocladium virens, Chaetomium globosum, Fusarium moniliforme, and Myrothecium verrucaria.
• Bacterial strains that can be used as industrial fungicides include, but are not limited to, slime fungi such as Sphaerotilis natans and Zoogloea ramigera.
• the compound of the present invention can also be used as an internal parasite control agent for livestock, poultry, pets, etc.
• target internal parasites include, but are not limited to, the following:
• Haemonchus Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Esphagostomum Oesophagostomum, Chabertia, Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis ), nematodes such as Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris, etc.
• Filariidae nematodes such as Wuchereria, Brugia, Onchoceca, Dirofilaria, and Loa
• Nematodes of the Dracunculidae family such as the genus Dracunculus; Dog tapeworm (Dipylidium caninum), cat tapeworm (Taenia taeniaeformis), Taenia solium (Taenia solium), Taenia saginata (Taenia saginata), reduced tapeworm (Hymenolepis diminuta), Beneden tapeworm (Moniezia benedeni), Cestodes such as Diphyllobothrium latum, Diphyllobothrium erinacei, Echinococcus granulosus, and Echinococcus multilocularis; Fasciola hepatica, F.
• the compound of the present invention can also be used as an antifungal agent.
• pathogenic bacteria targeted as antifungal agents include, but are not limited to, the following:
• Trichophyton fungi such as Trichophyton rubrum and Trichophyton mentagrophytes
• Candida fungi such as Candida albicans
• Aspergillus fungi such as Aspergillus fumigatus
• Cryptococcus fungi such as Cryptococcus neoformas, etc.
• the compounds of the present invention are usually mixed with a suitable solid or liquid carrier and, if desired, surfactants, penetrants, and spreading agents.
• a suitable solid or liquid carrier By adding adhesives, thickeners, anti-freeze agents, binders, anti-caking agents, disintegrants, or anti-decomposition agents, etc., it is possible to create liquid concentrates, emulsifiable concentrates, wettable powders. , water soluble powder, water dispersible granule, water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion
• the preparation in any of the above dosage forms can be enclosed in a water-soluble package and provided.
• Solid carriers include, for example, natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite or diatomaceous earth; calcium carbonate, ammonium sulfate, sodium sulfate or potassium chloride. Inorganic salts; synthetic silicic acid; or synthetic silicates; and the like.
• liquid carriers examples include alcohols such as ethylene glycol, propylene glycol or isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene or alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone; and ⁇ -butyrolactone.
• esters include esters; acid amides such as N-methylpyrrolidone or N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil or castor oil; or water; and the like.
• These solid and liquid carriers may be used alone or in combination of two or more.
• surfactant examples include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styrylphenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, or polyoxyethylene.
• Nonionic surfactants such as sorbitan fatty acid esters; alkyl sulfates, alkylbenzenesulfonates, ligninsulfonates, alkylsulfosuccinates, naphthalenesulfonates, alkylnaphthalenesulfonates, salts of formalin condensates of naphthalenesulfonic acids , salts of formalin condensates of alkylnaphthalene sulfonic acids, polyoxyethylene alkylaryl ether sulfates or phosphates, polyoxyethylene styrylphenyl ether sulfates or phosphates, polycarboxylate or polystyrene sulfonates, etc. Active agents; cationic surfactants such as alkylamine salts or alkyl quaternary ammonium salts; or amphoteric surfactants such as amino acid type or betaine type; and the like.
• the content of these surfactants is not particularly limited, but it is generally desirable to range from 0.05 to 20 parts by weight per 100 parts by weight of the formulation of the present invention. Further, these surfactants may be used alone or in combination of two or more.
• the compound of the present invention When the compound of the present invention is used as an agricultural chemical, other herbicides, various insecticides, acaricides, nematicides, fungicides, and plant growth regulators may be used at the time of formulation or spraying, as necessary. , synergist, fertilizer, soil conditioner, etc. may be applied in combination.
• the types of pesticides used in combination with the compound of the present invention include, for example, compounds described in The Pesticide Manual, 18th edition, 2018. Specific examples of the common names are as follows. However, the agricultural chemicals used in combination are not necessarily limited to these.
• Fungicides acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M (benalaxyl-M), benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacryl, benzamorf, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, bordeaux mixture, boscalid, bromoconazole, bupirimate, buthiobate, butylamine, calcium polysulfide, captafol
• Insecticides abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acynonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb ( aldicarb), allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethiphos, azinphos-ethyl ), azinphos-methyl, azocyclotin, bacillus thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate ( benzoximate), benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, bioresmethrin , bistriflur
• Parasitic drugs esfenvalerate, fenpropathrin, fenvalerate, alphacypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox ( etofenprox), lambda-cyhalothrin, permethrin, tefluthrin, zeta-cypermethrin, acetamiprid, clothianidin, dinotefuran, imidacloprid ), nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, pyriproxyfen, triflumuron, chlorpyrifos, Chlorpyrifos-methyl, diazinon, dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlor
• Antifungal agents such as ketoconazole and miconazole nitrate.
• Antibacterial agents amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, cefapirin, cefazolin, cefquinome, ceftiofur, chlortetracycline (chlortetracycline), clavulanic acid, danofloxacin, difloxacin, dinitolmide, enrofloxacin, florfenicol, lincomycin, lomefloxacin ( lomefloxacin, marbofloxacin, miloxacin, horramycin, nitrapyrin, norfloxacin, octhilinone, ofloxacin, orbifloxacin, oxolinic Oxolinic acid, oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate, tylosin isovalerate acetate (acetyl
• the amount of the compound of the present invention to be applied varies depending on the application situation, application time, application method, cultivated crop, etc., but in general, the appropriate amount of active ingredient is 0.005 to 50 kg per hectare (ha). Yes, preferably 0.01 to 1 kg.
• ⁇ emulsion ⁇ Compound of the present invention 0.1 to 30 parts
• Liquid carrier 45 to 95 parts
• Surfactant 4.9 to 15 parts
• Others 0 to 10 parts
• Other examples include spreading agents and decomposition inhibitors.
• Liquid Compound of the present invention: 0.01 to 70 parts Liquid carrier: 20 to 99.99 parts Others: 0 to 10 parts Other examples include antifreeze agents and spreading agents.
• the above preparation is diluted with water 1 to 10,000 times, preferably 100 to 10,000 times, or sprayed without dilution.
• formulations of agricultural and horticultural fungicides containing the compound of the present invention as an active ingredient will be shown, but the formulations of the present invention, including the compound of the present invention, are not limited to these.
• "parts" mean parts by weight.
• Emulsion Compound No. of the present invention 1-001 20 parts Methylnaphthalene 55 parts Cyclohexanone 20 parts Solpol 2680 5 parts (Mixture of nonionic surfactant and anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) The above components are mixed uniformly to form an emulsion. When used, the emulsion is diluted 50 to 20,000 times with water and sprayed at an amount of active ingredient of 0.005 to 50 kg per hectare.
• Hydrating agent Compound No. of the present invention 1-001 25 parts Pyrophyllite 66 parts Solpol 5039 4 parts (Anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) Carplex #80D 3 parts (white carbon: manufactured by Shionogi & Co., Ltd., product name) Calcium ligninsulfonate 2 parts
• the above ingredients are mixed and ground uniformly to make a wettable powder.
• the above-mentioned hydrating agent is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.
• Powder Compound No. 3 of the present invention 1-001 3 parts Carplex #80D 0.5 parts (white carbon: manufactured by Shionogi & Co., Ltd., product name) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above ingredients are uniformly mixed and ground to form a powder. When used, the powder is applied so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
• Granular hydrating agent Compound No. 6 of the present invention 1-001 75 parts Hytenol NE-15 5 parts (Anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd., trade name) Vanillex N 10 parts (anionic surfactant: manufactured by Nippon Paper Industries, trade name) Carplex #80D 10 parts (white carbon: manufactured by Shionogi & Co., Ltd., product name)
• the above ingredients are uniformly mixed and pulverized, a small amount of water is added, the mixture is stirred, the mixture is granulated using an extrusion granulator, and the mixture is dried to obtain a dry flowable agent. When using it, dilute it 50 to 20,000 times with water and spray it at a concentration of 0.005 to 50 kg of the active ingredient per hectare.
• Methods for applying the compound of the present invention include foliage spraying, soil treatment, and seed disinfection, but common methods commonly used by those skilled in the art are also effective.
• the present invention relates to the following [1] to [70].
• G represents G-1
• G-1 represents a structure represented by the following structural formula
• X 1 represents a halogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy
• R Y represents a hydrogen atom, a halogen atom, or a C 1 to C 6 alkyl
• R 1 represents a hydrogen atom or C 1 to C 6 alkyl
• R 2 represents a hydrogen atom or C 1 to C 6 alkyl
• R 5 represents a hydrogen atom or C 1 to C 6 alkyl
• R 6 represents a hydrogen atom or C 1 to C 6 alkyl
• r 1 represents an integer of 2
• two R 5 and two R 6 may be the same or different from each other
• R 7 represents C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl or phenyl
• R 8 represents a hydrogen atom or C 1 to C 6 alkyl
• R 9 represents a hydrogen atom or C 1 to C 6 alkyl
• Z represents Z-1, Z-2, Z-3, Z-4, Z-5, Z-6 or Z-7
• Z-1 to Z-7 each represent a structure represented by the following structural formula
• substitution position of Z 1 represents substitution on the aromatic ring of Z-1 to Z-7
• Z 1 is hydroxy, carboxy, amino, nitro, cyano, halogen atom, C 1 to C 6 alkyl, C 3 to C 10 cycloalkyl, C 1 to C 6 haloalkyl, C 3 to C 10 halocycloalkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylamino, C 1 -C 6 alkylcarbonyl , C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkyl substituted with R i , -OR d , -NHC(O)R e , -NR h C(O)R e , -NHSO 2 R i
• F-1 to F-15 each represent a structure represented by the following structural formula
• Z a is a halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylcarbonyl or C 1 -C 6 represents 6 alkoxycarbonyl,
• v7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z a may be the same or different from each other
• v6 represents an integer of 2, 3, 4, 5 or 6, each Z a may be the same or different from each other
• v5 represents an integer of 2, 3, 4 or 5
• each Z a may be the same or different from each other
• v4 represents an integer of 2, 3 or 4
• each Z a may be the same or different from each other
• v3 represents an integer of 2 or 3
• each Z a when v3 represents an integer of 2 or 3, each Z a
• R b represents cyano or phenyl
• X 1 represents a halogen atom
• R a represents a hydrogen atom, C 1 to C 6 alkyl, R a -1 or R a -4
• R 5 represents a hydrogen atom
• R 6 represents a hydrogen atom
• R 7 represents C 1 -C 6 alkyl
• Z represents Z-1, Z-2, Z-3, Z-4 or Z-6
• Z 1 is hydroxy, carboxy, amino, nitro, cyano, halogen atom, C 1 to C 6 alkyl, C 3 to C 10 cycloalkyl, C 1 to C 6 haloal
• R 2 represents a hydrogen atom, The pyrazole compound or a salt thereof according to [2] above, wherein p represents an integer of 1.
• G 1 represents a halogen atom, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy
• T represents an oxygen atom
• R X represents C 1 -C 6 alkyl, benzyl, R X -1 or R X -2
• R 1 represents a hydrogen atom
• R a represents a hydrogen atom
• Z represents Z-1, Z-2 or Z-3
• Z 1 represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy
• n5 represents an integer of 0, 1 or 2
• G 1 represents a halogen atom, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy
• T represents an oxygen atom
• R X represents C 1 -C 6 alkyl, benzyl, R X -1 or R X -2
• RY represents a hydrogen atom
• R 1 represents a hydrogen atom
• R a represents a hydrogen atom, C 1 to C 6 alkyl or R a -1
• R 5 represents a hydrogen atom
• R 6 represents a hydrogen atom
• Z represents Z-1, Z-2 or Z-3
• Z 1 represents a halogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio
• Z 1 when n5 represents an integer of 2, each Z 1 may be the same
• G 1 represents a halogen atom or C 1 to C 6 haloalkyl
• T represents an oxygen atom
• R X represents C 1 to C 6 alkyl
• RY represents a hydrogen atom
• R 1 represents a hydrogen atom
• R 2 represents a hydrogen atom
• R 3 represents a hydrogen atom
• R 4 represents a hydrogen atom
• R 5 represents a hydrogen atom
• R 6 represents a hydrogen atom
• R 7 represents C 1 -C 6 alkyl
• Z represents Z-1
• Z 1 represents a halogen atom or C 1 to C 6 alkyl
• each Z 1 may be the same or different from each other
• m5 represents an integer of
• G 1 represents C 1 -C 6 alkyl or C 1 -C 6 haloalkyl
• R represents a hydrogen atom or C 1 to C 6 alkyl
• T represents an oxygen atom
• R represents a hydrogen atom or C 1 to C 6 alkyl
• R' represents C 1 to C 6 alkyl
• R X represents C 1 to C 6 alkyl
• RY represents a hydrogen atom
• R 1 represents a hydrogen atom or R 2 represents a hydrogen atom
• R 3 represents a hydrogen atom
• R 4 represents a hydrogen atom
• R a represents a hydrogen atom
• Z represents Z-1
• G 1 represents C 1 to C 6 haloalkyl
• T represents an oxygen atom
• R X represents C 1 to C 6 alkyl
• RY represents a hydrogen atom
• R 1 represents C 1 -C 6 alkyl
• R 2 represents a hydrogen atom
• R 3 represents a hydrogen atom
• R 4 represents a hydrogen atom
• R a represents a hydrogen atom
• Z represents Z-1
• Z 1 represents C 1 -C 6 alkyl or C 1 -C 6 alkyl substituted with R i
• Z 1 when n5 represents an integer of 2, each Z 1 may be the same or different from each other, R i represents C 1 to C 6 alkoxy, m5 represents an integer of 0 or 1, The pyrazole compound or a salt thereof according to [3] above, wherein n5 represents an integer of 1 or 2.
• G 1 represents C 1 to C 6 haloalkyl
• T represents a sulfur atom
• R X represents C 1 to C 6 alkyl or R X -1
• RY represents a hydrogen atom
• R 1 represents a hydrogen atom
• R 2 represents a hydrogen atom
• R 3 represents a hydrogen atom
• R 4 represents a hydrogen atom
• R a represents a hydrogen atom
• Z represents Z-1
• Z 1 represents C 1 to C 6 alkyl
• Z 1 represents C 1 to C 6 alkyl
• n5 represents an integer of 2
• m5 represents an integer of 1
• n5 represents an integer of 1 or 2
• u5 represents an integer of 0.
• G 1 represents C 1 to C 6 haloalkyl
• T represents an oxygen atom
• R X represents C 1 to C 6 alkyl
• RY represents a hydrogen atom
• R 1 represents a hydrogen atom
• R 2 represents a hydrogen atom
• R 3 represents a hydrogen atom
• R 4 represents a hydrogen atom
• R a represents a hydrogen atom
• Z represents Z-1
• Z 1 represents C 1 -C 6 alkyl or -OR d
• n5 represents an integer of 2
• each Z 1 may be the same or different from each other
• R d represents C 1 to C 6 haloalkyl
• m5 represents an integer of 1
• G 1 represents C 1 to C 6 haloalkyl
• T represents an oxygen atom
• R X represents C 1 to C 6 alkyl
• RY represents a hydrogen atom
• R 1 represents a hydrogen atom
• R 2 represents a hydrogen atom
• R 3 represents a hydrogen atom
• R 4 represents a hydrogen atom
• R a represents a hydrogen atom
• Z represents Z-1
• Z 1 represents E-1 or E-2
• Z a represents a halogen atom
• Z a when v5 represents an integer of 2, each Z a may be the same or different from each other, m5 represents an integer of 2, n5 represents an integer of 2, v4 represents an integer of 0,
• G 1 represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl
• R X represents C 1 to C 6 alkyl or R X -1
• RY represents a hydrogen atom
• R a represents a hydrogen atom or C 1 to C 6 alkyl
• Z represents Z-1
• Z 1 represents hydroxy, a halogen atom, C 1 to C 6 alkyl, -NHC(O)R e , -NR h C(O)R e or E-2
• n5 represents an integer of 0, 1 or 2
• the pyrazole compound or its salt according to any one of [1] to [15] above, wherein u5 represents an integer of 0.
• G 1 represents a chlorine atom, a bromine atom, methyl or trifluoromethyl
• R X represents t-butyl or R X -1
• R a represents a hydrogen atom or methyl
• G 1 is a halogen atom, C 1 to C 6 alkyl, C 3 to C 10 cycloalkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 1 to C 6 alkylthio , C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkyl represents aminocarbonyl, C3 - C10 cycloalkylaminocarbonyl or di(C1 - C6 alkyl)aminocarbonyl,
• m5 represents an integer of 2
• each G1 may be the same or different from each other,
• the pyrazole compound or a salt thereof according to any one of [1] to
• G 1 is a halogen atom, C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, di(C 1 -C 6 haloalkoxy), 6alkyl )amino, C1- C6alkylcarbonyl , C1 - C6alkoxycarbonyl , C1 -C6alkylaminocarbonyl , C3 - C10cycloalkylaminocarbonyl or di( C1 - C6alkyl )amino represents carbonyl,
• m5 represents an integer of 2
• each G1 may be the same or different from each other,
• G 1 is a halogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylcarbonyl, or C 1 -C 6 alkoxy represents carbonyl,
• m5 represents an integer of 2
• each G1 may be the same or different from each other,
• G 1 represents a halogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy,
• m5 represents an integer of 2
• each G1 may be the same or different from each other,
• G 1 represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl
• m5 represents an integer of 2
• each G1 may be the same or different from each other,
• G 1 represents a chlorine atom, a bromine atom, methyl, ethyl or trifluoromethyl
• each G1 may be the same or different from each other,
• G 1 represents a halogen atom or C 1 to C 6 haloalkyl
• each G1 may be the same or different from each other,
• G 1 represents a chlorine atom, a bromine atom or trifluoromethyl
• each G1 may be the same or different from each other,
• R X is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl , C 1 -C 6 alkyl substituted with R c , benzyl , R -4, X 1 represents a halogen atom,
• each X 1 may be the same or different from each other, X 1 represents a halogen atom, R c represents cyano, C 3 -C 10 cycloalkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl or di(C 1 -C 6 alkyl)aminocarbonyl,
• u5 represents an integer of 0 or 1
• the pyrazole compound or its salt according to any one of [1] to [6] and [18] to [27] above, wherein u4 represents an integer of 0.
• R X represents C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, R x -1, R x -2, R x -3 or R x -4, u5 represents an integer of 0,
• u4 represents an integer of 0.
• R X represents C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, R x -1 or R x -2, u5 represents an integer of 0, The pyrazole compound or a salt thereof according to [29] above, wherein u4 represents an integer of 0.
• R X represents C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or R x -1, The pyrazole compound or a salt thereof according to [30] above, wherein u5 represents an integer of 0.
• R X represents C 1 to C 6 alkyl or R X -1, The pyrazole compound or a salt thereof according to [31] above, wherein u5 represents an integer of 0.
• R a represents a hydrogen atom, C 1 to C 6 alkyl, R a -1 or R a -4, R 5 represents a hydrogen atom, R 6 represents a hydrogen atom, R 7 represents C 1 -C 6 alkyl; r 1 represents an integer of 1, The pyrazole compound or its salt according to any one of the above [1] to [6] and [18] to [34], wherein t represents an integer of 0, 1 or 2.
• R a represents R a -1 or R a -4, R 5 represents a hydrogen atom, R 6 represents a hydrogen atom, R 7 represents C 1 -C 6 alkyl; r 1 represents an integer of 1, The pyrazole compound or a salt thereof according to [35] above, wherein t represents an integer of 0, 1 or 2.
• R a represents R a -1
• R 5 represents a hydrogen atom
• R 6 represents a hydrogen atom
• R 7 represents methyl
• R a represents R a -4
• R 5 represents a hydrogen atom
• R 6 represents a hydrogen atom
• R 7 represents methyl
• Z 1 is substituted with hydroxy, halogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, R i C 1 to C 6 alkyl, -OR d , -NHC(O)R e , -NR h C(O)R e or E-2, The pyrazole compound or a salt thereof according to [45] above, wherein R d represents C 1 to C 6 haloalkyl.
• Z 1 is a halogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C substituted with R i 1 to C 6 alkyl, -OR d , -NHC(O)R e , -NR h C(O)R e or E-2, The pyrazole compound or a salt thereof as described in [46] above, wherein R d represents C 1 to C 6 haloalkyl.
• Z 1 represents a halogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, -OR d or E-2, The pyrazole compound or a salt thereof as described in [47] above, wherein R d represents C 1 to C 6 haloalkyl.
• Z 1 represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy, The pyrazole compound or a salt thereof according to the above [7] or [48], wherein n5 represents an integer of 0, 1 or 2.
• Z 1 represents a chlorine atom, a bromine atom, methyl or methoxy
• n5 represents an integer of 0, 1 or 2.
• n5 represents an integer of 1 or 2.
• n5 represents an integer of 2.
• Z represents Z-2 or Z-3, The pyrazole compound or a salt thereof according to any one of [1] to [7] and [18] to [42] above, wherein n7 represents an integer of 0.
• Z represents Z-4 or Z-6
• Z 1 represents a halogen atom
• the pyrazole compound or a salt thereof according to any one of [1] to [6] and [18] to [42] above, wherein n3 represents an integer of 0 or 1.
• G 1 represents a halogen atom, C 3 to C 6 cycloalkyl or C 1 to C 6 haloalkyl
• R X represents C 1 -C 6 alkyl, benzyl or R X -1
• X 1 represents a halogen atom or C 1 to C 6 alkyl
• R Y represents a hydrogen atom, a halogen atom, or a C 1 to C 6 alkyl
• R 1 represents a hydrogen atom or C 1 to C 6 alkyl
• R 2 represents a hydrogen atom or C 1 to C 6 alkyl
• R 3 represents a hydrogen atom, a halogen atom or a C 1 to C 6 alkyl
• R 4 represents a hydrogen atom
• T represents an oxygen atom
• X 1 represents a halogen atom
• RY represents a hydrogen atom
• R 1 represents a hydrogen atom
• R 3 represents a halogen atom
• R 4 represents a halogen atom
• R a represents a hydrogen atom or C 1 to C 6 alkyl
• Z 1 represents C 1 to C 6 alkyl
• m5 and n5 represent an integer of 1 or 2
• G 1 represents a halogen atom, C 3 to C 10 cycloalkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, or di(C 1 to C 6 alkylamino);
• R X represents C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, benzyl or R X -1
• X 1 represents a halogen atom or C 1 to C 6 alkyl
• R Y represents a hydrogen atom, a halogen atom, or a C 1 to C 6 alkyl
• R 1 represents a hydrogen atom or C 1 to C 6 alkyl
• R 2 represents a hydrogen atom
• G 1 represents a halogen atom, C 3 -C 10 cycloalkyl or C 1 -C 6 haloalkyl
• T represents an oxygen atom
• X 1 represents a halogen atom
• RY represents a hydrogen atom
• R 1 represents a hydrogen atom
• R 3 represents a hydrogen atom or a halogen atom
• R 4 represents a hydrogen atom or a halogen atom
• R a represents a hydrogen atom, C 1 to C 6 alkyl or R a -1
• R 5 represents a hydrogen atom
• R 6 represents a hydrogen atom
• R 7 represents C 1 -C 6 alkyl
• Z represents Z-1 or Z-2
• m5 represents an integer of 0, 1 or 2
• n5 represents an integer of 1 or 2
• u5 represents an integer of 0 or 1
• n7 represents an integer of 0,
• R b is cyano
• G represents G-1
• G-1 represents a structure represented by the following structural formula
• X 1 represents a halogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy
• R Y represents a hydrogen atom, a halogen atom, or a C 1 to C 6 alkyl
• m5 and u5 represent integers of 0, 1, 2, 3, 4 or 5, u
• G 1 represents a halogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 alkylthio
• R x represents C 1 -C 6 alkyl, benzyl, R x -1, R x -2, or R x -3
• X 1 represents a halogen atom
• RY represents a hydrogen atom
• m5 represents an integer of 0, 1 or 2
• u5 represents an integer of 0 or 1
• An antifungal agent containing as an active ingredient one or more selected from the pyrazole compounds and salts thereof according to any one of [1] to [63] above.
• An internal parasite control agent containing as an active ingredient one or more selected from the pyrazole compounds and salts thereof according to any one of [1] to [63] above.
• the chemical shift value of the proton nuclear magnetic resonance spectrum (hereinafter referred to as 1 H-NMR) described below was determined using Me 4 Si (tetramethylsilane) as a reference material and 300 MHz (model: JNM-ECX300). or JNM-ECP300, manufactured by JEOL) or 400 MHz (model: JNM-ECZ400S, manufactured by JEOL).
• the symbols in the chemical shift values of 1 H-NMR represent the following meanings. s: singlet, d: doublet, dd: double doublet, t: triplet, dt: double triplet, q: quartet, sep: septet, m: multiplet, br: broad singlet.
• Step 1 Synthesis of 1-phenyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid 4-iodo-1-phenyl-1H- Add 0.42 ml of 3-(trifluoromethyl)phenol, 1.6 g of cesium carbonate, 19 mg of 4-(dimethylamino)pyridine, and trifluoromethanesulfone to a mixed solution of 1.0 g of pyrazole-5-carboxylic acid and 5 ml of xylene at room temperature. 33 mg of acid copper (monovalent) toluene complex was sequentially added. After purging with nitrogen, the mixture was stirred at reflux temperature for 8 hours.
• Step 2 N-(2-(2,4-dimethylphenyl)-2,2-difluoroethyl)-1-phenyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide ( Synthesis of Compound No. 2-001) A mixed solution of 173 mg of 1-phenyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid obtained in Step 1 and 4 ml of dichloromethane was added at room temperature.
• the obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
• the obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate [gradient from 9:1 to 1:9 (volume ratio, the same applies hereinafter)] as an eluent to obtain 62 mg of the target product. Obtained as a yellow solid. Melting point: 82-85°C.
• Synthesis Example 2 Synthesis of N-(2,4-dimethylphenethyl)-1-ethyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 2-159) N -(2,4-Dimethylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide 500 mg, potassium carbonate 332 mg, and dimethylformamide 5 ml were added to a mixed solution of ethyl iodide at room temperature. 0.19 ml was added and stirred at 50°C for 1 hour.
• the obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
• the resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as the eluent to obtain 61 mg of the desired product as a solid. Melting point 131-133°C.
• the obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
• the resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as the eluent to obtain 65 mg of the desired product as a colorless oil.
• Synthesis Example 5 Synthesis of 1-isopropyl-N-(4-methylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carbothioamide (Compound No. 6-002) 1- Add 340 mg of Lawesson's reagent to a mixed solution of 300 mg of isopropyl-N-(4-methylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 4 ml of xylene at room temperature, The mixture was stirred at room temperature of 120°C for 2 hours.
• Reference Example 1 Synthesis of 4-iodo-1-phenyl-1H-pyrazole-5-carboxylic acid N- 2.5 g of iodosuccinimide was added and stirred at 80° C. for 30 minutes. After the reaction was completed, 50 ml of water was added at room temperature, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure to obtain 2.69 g of the target product as a pink solid. Melting point 191-193°C.
• Step 2 Synthesis of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole 4-(dimethylamino)-3-(3-(trifluoromethyl)
• Step 3 Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid
• 1-(tert-butyl)-5-methyl-4-(3 1.48 g of potassium permanganate was added to a mixed solution of 930 mg of -(trifluoromethyl)phenoxy)-1H-pyrazole, 8.5 ml of tert-butyl alcohol, and 4.3 ml of water at room temperature, and the mixture was heated to 100°C for 2 hours. Stir for hours. After the stirring was completed, 1.48 g of potassium permanganate was added to the reaction mixture at the same temperature, and the mixture was stirred at the same temperature for 2 hours.
• the reaction mixture was filtered through Celite, and the Celite was washed with 20 ml of water.
• a 1 mol/l aqueous hydrochloric acid solution was added until the pH reached 1, and the mixture was extracted with chloroform (20 ml x 2).
• the obtained organic layer was washed with water, then dehydrated and dried with saturated brine and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
• the obtained solid was washed with 5 ml of n-hexane and then dried under reduced pressure to obtain 209 mg of the desired product as a white solid. Melting point: 120-124°C.
• the mixture was stirred at °C for 30 minutes. After the reaction was completed, the reaction mixture was added to a mixed solution of 28 g of potassium carbonate, 50 ml of water, and 5 ml of ethanol, and stirred at room temperature for 1 hour. After the stirring was completed, the reaction mixture was extracted with toluene (40 ml x 2). The obtained organic layer was washed with water, then dehydrated and dried over saturated brine and then over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 4.40 g of the desired product as a brown oil.
• Step 2 Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole 2.0 g of 3-(dimethylamino)-2-(3-(trifluoromethyl)phenoxy)acryaldehyde, A mixed solution of 2.4 g of benzylhydrazine hydrochloride, 2.1 ml of triethylamine and 25 ml of 1,4-dioxane was stirred at 100° C. for 3 hours. After the reaction was completed, 20 ml of a 1 mol/l aqueous hydrochloric acid solution was added to the reaction mixture at room temperature, and the mixture was extracted with chloroform (30 ml x 2).
• Step 3 Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid 1-benzyl-4-(3-(trifluoromethyl)phenoxy) under nitrogen atmosphere
• 1.0 g of dry ice was added to the reaction mixture at -78°C, and the mixture was stirred at the same temperature for 5 minutes.
• Step 2 Synthesis of tert-butyl (1-(2,4-dimethylphenyl)-3-ethoxypropan-2-yl)carbamate (1-(2,4-dimethylphenyl)-3-hydroxypropane-2- 2 ml of a 50% by mass aqueous sodium hydroxide solution, 12 mg of tetrabutylammonium bromide and 828 mg of diethyl sulfate were added in sequence to a mixed solution of 1.0 g of tert-butyl carbamate and 20 ml of n-hexane at room temperature, and at 65°C. Stirred for 5 hours.
• Step 3 Synthesis of 1-(2,4-dimethylphenyl)-3-ethoxypropan-2-amine tert-butyl (1-(2,4-dimethylphenyl)-3-ethoxypropan-2-yl)carbamate
• a mixed solution of 1.04 g and 15 ml of 1,4-dioxane was added 5 ml of a 35% by mass hydrochloric acid aqueous solution at room temperature, and the mixture was stirred at the same temperature for 18 hours.
• the solvent of the reaction mixture was distilled off under reduced pressure, and 10 ml of water was added to the resulting residue, which was washed with a mixed solution of 10 ml of n-hexane and 10 ml of ethyl acetate.
• a 1 mol/l aqueous sodium hydroxide solution was added to the resulting aqueous layer to adjust the pH to 10, followed by extraction with 20 ml of ethyl acetate.
• the obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 657 mg of the desired product as a colorless oil.
• Step 2 Synthesis of ethanethioic acid S-(2-((tert-butoxycarbonyl)amino)-3-(2,4-dimethylphenyl)propyl) 4-methylbenzenesulfonic acid 2-((tert-butoxycarbonyl)amino) )
• 0.75 g of potassium thioacetate was added at room temperature, and the mixture was heated at the same temperature for 2 hours and 30 minutes. Stirred.
• Step 3 Synthesis of tert-butyl (1-(2,4-dimethylphenyl)-3-(methylthio)propan-2-yl)carbamate S-(2-((tert-butoxycarbonyl)amino)- To a mixed solution of 1.51 g of 3-(2,4-dimethylphenyl)propyl), 1.21 g of potassium carbonate, and 8 ml of methanol was added 0.93 g of methyl iodide at room temperature, and the mixture was heated at the same temperature for 1 hour and 30 minutes. Stirred. After the reaction was completed, the solvent was distilled off under reduced pressure.
• Step 4 Synthesis of 1-(2,4-dimethylphenyl)-3-(methylthio)propan-2-amine (1-(2,4-dimethylphenyl)-3-(methylthio)propan-2-yl)carbamine
• a mixed solution of 1.28 g of tert-butyl acid and 10 ml of 1,4-dioxane was added 3 ml of 35% by mass hydrochloric acid at room temperature, and the mixture was stirred at the same temperature for 3 hours and 30 minutes. After the reaction was completed, the solvent was distilled off under reduced pressure.
• a 1 mol/l aqueous sodium hydroxide solution was added to the resulting aqueous layer until the pH reached 13, and the mixture was extracted with ethyl acetate (10 ml x 1).
• the solvent was distilled off under reduced pressure to obtain 0.61 g of the desired product as an oil.
• Step 2 Synthesis of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate (compound No. ii-005) Under nitrogen atmosphere, (4-(3-bromo Add 0.50 g of methyl phenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate, 0.89 g of trimethylboroxine, 0.92 g of cesium carbonate, and 10 ml of 1,4-dioxane to a mixed solution of 10 ml of 1,4-dioxane at room temperature.
• Step 3 Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid (compound No. i-036) (1-(tert-butyl)-4-( A mixed solution of 27.1 g of sodium hydroxide and 100 ml of water was added to a mixed solution of 39.0 g of methyl 3-methylphenoxy)-1H-pyrazole-5-carboxylate and 100 ml of methanol at room temperature, and the mixture was heated at 45°C for 16 hours. The mixture was stirred for an hour. After the reaction was completed, the solvent was distilled off under reduced pressure.
• the compound of the present invention can be synthesized according to the aforementioned Synthesis Examples and Reference Examples.
• Tables 1 to 7 list examples of pyrazole compounds included in the present invention that were produced in the same manner as Synthesis Examples 1 to 7, and Table 7 lists examples of production intermediates that were produced in the same manner as Reference Examples 1 to 6. Although shown in Tables 8 to 9, the pyrazole compounds and production intermediates included in the present invention are not limited thereto.
• the notation "*" indicates that the compound is an oily or resinous compound with no melting point
• "**” indicates that the compound was decomposed when the melting point was measured
• "m.p. .'' represents the melting point (unit: °C).
• ">” in the table represents a higher temperature; for example, ">300” in the table means that the compound whose melting point was measured did not melt at 300°C.
• "4-" in “4-Me-Ph” represents a substitution position on the phenyl group as described below.
• “4-Me-Ph” represents 4-methylphenyl
• "2,6-F 2 -Ph” represents 2,6-difluorophenyl.
• the description "4-" in "1-Me-Ph” represents a substitution position on the phenyl group as described below.
• “4-Me-Ph” represents 4-methylphenyl
• "2,6-F 2 -Ph” represents 2,6-difluorophenyl.
• the substituents represented by 1d, Z-2a, Z-3a, Z-4a, Z-4b and Z-6a each represent the following structures.
• test chemical solution The compound of the present invention was mixed with an emulsified white sample (Solpol (registered trademark) 3005XL (manufactured by Toho Chemical Industry Co., Ltd.), N-methylpyrrolidone, and Solvesso (registered trademark) 200 (manufactured by ExxonMobil) [1:5 :28 (weight ratio)] to prepare emulsions with a concentration of 1% by mass, 5% by mass, or 20% by mass. These emulsions were used as test solutions in Test Examples 1 to 7 below. .
• Solpol registered trademark
• 3005XL manufactured by Toho Chemical Industry Co., Ltd.
• N-methylpyrrolidone N-methylpyrrolidone
• Solvesso (registered trademark) 200 manufactured by ExxonMobil
• the following compounds showed a control value of 70% or more.
• Test Example 2 Tomato powdery mildew control effect test Tomatoes (variety: Momotaro) were planted in a 90 cm 3 plastic pot, and at the 2-leaf stage, 5 ml of the test chemical solution diluted with water to 500 ppm was sprayed. . After air-drying, the tomatoes were placed in an air-conditioned greenhouse (temperature 20° C., humidity 70% RH), and a conidial suspension of tomato powdery mildew fungus (Levillula taurica) was spray inoculated. After leaving it for 14 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.
• the following compounds showed a pest control value of 70% or more.
• Test Example 3 Cucumber Gray Mold Control Efficacy Test Cucumbers (variety: Frost-free Chizo) were planted in a 90 cm 3 plastic pot, and at the cotyledon stage, 5 ml of the test chemical solution diluted with water to 500 ppm was sprayed. processed and air dried. The treated leaves were then cut and placed in a plastic container. A conidial suspension of Botrytis cinerea and dissolved PDA medium were mixed at a ratio of 1:1 (volume ratio), and 30 ⁇ l each was inoculated dropwise onto the treated leaves. After inoculation, the plants were placed at 20° C. and under high humidity (100% RH) for 3 days. Thereafter, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.
• the following compounds showed a control value of 70% or more.
• Test Example 4 Cucumber Sclerotinia Disease Control Efficacy Test Cucumbers (variety: Shimozushijijiori) were planted in a 90 cm 3 plastic pot, and at the cotyledon stage, 5 ml of the test chemical solution diluted with water to 500 ppm was sprayed. and air dried. The treated leaves were then placed in a plastic container. Agar pieces (diameter 5 mm) containing bacteria of cucumber Sclerotinia sclerotiorum, which had been cultured in PDA medium in advance, were inoculated onto cotyledons of cucumbers treated with the drug.
• the plastic container was covered with vinyl, humidified (humidity 100% RH), and placed at 20°C for 2 days. Thereafter, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.
• the following compounds showed a control value of 70% or more.
• Test Example 5 Cucumber Powdery Mildew Control Efficacy Test A cucumber (variety: Frost-free Chizo) was planted in a 90 cm 3 plastic pot, and at the cotyledon stage, 5 ml of the test chemical solution diluted with water to 500 ppm was sprayed. Processed. After air-drying, the cucumbers were placed in an air-conditioned greenhouse (temperature 20° C., humidity 70% RH), and a conidial suspension of cucumber powdery mildew fungus (Erysiphe polygoni) was spray inoculated. After leaving for 9 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.
• the following compounds showed a control value of 70% or more.
• Test Example 6 Cucumber Anthracnose Control Efficacy Test Cucumbers (variety: Shimozurejizo) were planted in a 90 cm 3 plastic pot, and at the cotyledon stage, 5 ml of the test chemical solution diluted with water to 500 ppm was sprayed. did. One day after the spraying, cucumbers were spray-inoculated with a conidial suspension of Colletotrichum lagenarium and placed in an inoculation box at a temperature of 25° C. and a humidity of 100% RH for 2 days. Thereafter, it was placed in an air-conditioned greenhouse (temperature 23°C, humidity 60% RH) and maintained for 7 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.
• the following compounds showed a control value of 70% or more.
• Test Example 7 Soybean Rust Control Efficacy Test Soybean (variety: Enrei) was planted in a 90 cm 3 plastic pot, and at the single leaf stage, 5 ml of a test chemical solution diluted with water to 500 ppm was sprayed. One day after the spraying, soybeans were spray-inoculated with a conidial suspension of Phakopsora pachyrhizi and placed in an inoculation box at a temperature of 20° C. and a humidity of 100% RH for two days. Thereafter, it was placed in an air-conditioned greenhouse (temperature 20° C., humidity 60% RH) and kept for 10 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.
• the following compounds showed a control value of 70% or more.
• the pyrazole compound according to the present invention is an extremely useful compound that exhibits excellent pest control activity, especially bactericidal activity, and has almost no adverse effects on non-target organisms such as mammals, fish, and useful insects. be.

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