Classifications

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  • 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
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  • 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
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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  • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
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  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P13/00—Herbicides; Algicides
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  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P3/00—Fungicides
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  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P5/00—Nematocides
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  • A01P7/00—Arthropodicides
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  • 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
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  • 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
  • A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
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  • 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
  • A61K31/42—Oxazoles
  • A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
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  • 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
  • A61K31/4245—Oxadiazoles
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  • 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
  • A61K31/425—Thiazoles
  • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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  • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
  • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
  • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
  • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
• • A—HUMAN NECESSITIES
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  • A61K31/47—Quinolines; Isoquinolines
  • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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• • A—HUMAN NECESSITIES
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  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
  • A61P31/04—Antibacterial agents
• • A—HUMAN NECESSITIES
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  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
  • A61P31/10—Antimycotics
• • A—HUMAN NECESSITIES
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• • A—HUMAN NECESSITIES
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  • 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
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  • 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
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  • 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
  • C07D401/12—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 linked by a chain containing hetero atoms as chain links
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  • 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
  • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
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  • 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
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  • C07F7/12—Organo silicon halides

Definitions

• the present invention relates to novel pyrazole compounds and their salts, as well as pest control agents containing the compounds and their salts as active ingredients.
• Patent documents 1 to 3 disclose certain pyrazole compounds, but do not disclose anything about the pyrazole compounds of the present invention.
• Patent Documents 4 and 5 disclose that certain pyrazole compounds are useful as fungicides, but do not disclose anything about the pyrazole compounds of the present invention.
• novel pyrazole compound according to the present invention represented by the following formula (1), exhibits excellent control activity as a fungicide, particularly as an agricultural and horticultural fungicide, and have completed the present invention.
• the pyrazole compounds of the present invention have not been disclosed in any literature, and their usefulness as pest control agents is not known.
• the present invention relates to the following [1].
• G represents G-1
• G-1 represents a structure represented by the following structural formula:
• G 1 represents hydroxy, nitro, cyano, a halogen atom, C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl , C 1 -C 6 alkylsulfonyl or di(C 1 -C 6 alkyl)amino;
• T represents an oxygen atom
• W represents -O- or -N(R W )-
• R X represents C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, benzyl,
• X 1 represents a halogen atom, a C 1 -C 6 alkyl, a C 1 -C 6 haloalkyl or a C 1 -C 6 alkoxy;
• each X1 when u5 represents an integer of 2, 3, 4 or 5, each X1 may be the same as or different from each other;
• each X1 when u4 represents an integer of 2, 3 or 4, each X1 may be the same as or different from each other;
• R Y represents a hydrogen atom, a halogen atom or a C 1 -C 6 alkyl group;
• R 1 represents a hydrogen atom, a C 1 -C 6 alkyl or a C 1 -C 6 alkyl substituted with R i ;
• R W is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl substituted with R a, C 2 -C 6 alkenyl,
• R D represents a halogen atom, nitro or C 1 -C 6 alkyl; In the relationship with R D , when t5 represents an integer of 2, 3, 4 or 5, each R D may be the same as or different from each other; R e represents C 1 -C 6 alkyl or C 1 -C 6 alkoxy; R f represents C 1 -C 6 alkyl; R g represents Q-1 to Q-53 or Q-54; R h represents cyano or C 1 -C 6 alkoxy; R i represents cyano or C 1 -C 6 alkoxy; Z represents Z-1 to Z-49 or Z-50; Z-1 to Z-50 each represent a structure represented by the following structural formula:
• Z1 represents that it is substituted on the aromatic ring of Z-1 to Z-50.
• Z a represents a halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted with R 6 , C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy , C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, phenyl, S-1 to S-5 or S-6;
• v5 represents an integer of 2, 3, 4 or 5 in relation to Z a
• each Z a may be the same as or different from each other;
• v4 represents an integer of 2, 3 or 4 in relation to Z a
• each Z a may be the same as or different from each other;
• v3 represents an integer of 2 or 3 relative to Z a
• each Z a may be the same as or different from each other;
• v2 represents an integer of 2 in relation to Z
• Q-1 to Q-54 each represent a structure represented by the following structural formula:
• Zc represents 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 alkoxycarbonyl;
• w5 represents an integer of 2, 3, 4 or 5
• each Zc may be the same as or different from each other
• w4 represents an integer of 2, 3 or 4
• each Zc may be the same as or different from each other;
• Zc when w3 represents an integer of 2 or 3, each Zc may be the same as or different from each other;
• Zc when w2 represents an integer of 2
• each Zc may be the same as or different from each other;
• Zd represents C 1 -C 6 alkyl;
• m5 represents an integer of 0, 1, 2, 3, 4 or 5;
• n2 represents an integer of 0,
• the compound of the present invention represented by formula (1) exhibits excellent control activity against many pathogens. Therefore, the present invention can provide a useful fungicide, particularly a fungicide for agricultural and horticultural use.
• the compounds of the present invention may have geometric isomers, E- and Z-isomers, depending on the type of substituents, and the present invention includes mixtures containing these E-, Z-, or E- and Z-isomers in any ratio.
• the compounds of the present invention may exist in optically active forms due to the presence of one or more asymmetric carbon atoms or sulfur atoms, but the present invention encompasses all optically active forms and racemic forms.
• the compounds of the present invention may have tautomers depending on the type of substituents, but the present invention includes all tautomers or mixtures of tautomers in any ratio.
• the compounds of the present invention may exist as one or more rotational isomers due to restricted bond rotation caused by steric hindrance between substituents, but the present invention encompasses all rotational isomers or mixtures of diastereomers containing them in any ratio.
• n- means normal
• i- means iso
• s- means secondary
• tert- means tertiary
• Ph means phenyl
• halogen atom includes fluorine atom, chlorine atom, bromine atom and iodine atom. In this specification, the term “halo” also refers to these halogen atoms.
• C a -C b alkyl in this specification represents a linear or branched saturated hydrocarbon group having a to b carbon atoms, specific examples of which include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, and n-hexyl, each of which is selected within the range of the number of carbon atoms specified.
• C a -C b haloalkyl represents a linear or branched saturated hydrocarbon group having a to b carbon atoms in which hydrogen atoms bonded to the carbon atoms are optionally substituted with halogen atoms, and in this case, when substituted with two or more halogen atoms, the halogen atoms may be the same or different from each other.
• Specific examples include fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl, and the like, and each is selected within the range of the number of carbon atoms specified.
• C a -C b alkenyl in this specification represents a linear or branched unsaturated hydrocarbon having a to b carbon atoms and having one or more double bonds in the molecule, and specific examples thereof include vinyl, 1-propenyl, 2-propenyl (hereinafter also referred to as allyl), 1-methylethenyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl, 1,1-dimethyl-2-propenyl, and the like, each of which is selected within the specified range of the number of carbon atoms.
• C a -C b alkynyl in the present specification represents a linear or branched unsaturated hydrocarbon having a to b carbon atoms and having one or more triple bonds in the molecule, and specific examples thereof include ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-hexynyl, etc., each of which is selected within the range of the specified number of carbon atoms.
• C a -C b alkoxy in the present specification represents alkyl-O- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, 2-ethylhexyloxy, and the like, each selected within the range of the specified number of carbon atoms.
• C a -C b haloalkoxy in the present specification represents haloalkyl-O- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 1,1,2,3,3,3-hexafluoropropyloxy, and the like, each of which is selected within the range of the specified number of carbon atoms.
• C a -C b alkenyloxy in the present specification represents alkenyl-O- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include vinyloxy, 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 2-butenyloxy, 2-methyl-2-propenyloxy, 3-methyl-2-butenyloxy, 1,1-dimethyl-2-propenyloxy, and the like, each selected within the specified range of carbon atoms.
• C a -C b alkylthio in the present specification represents alkyl-S- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, tert-butylthio, etc., each of which is selected within the range of the specified number of carbon atoms.
• C a -C b haloalkylthio in the present specification represents haloalkyl-S- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2,-tetrafluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, 1,1,2,3,3,3-hexafluoropropylthio, and the like, each of which is selected within the range of the specified number of carbon atoms.
• C a -C b alkylsulfinyl in the present specification represents alkyl-S(O)- as defined above having a to b carbon atoms, and specific examples thereof include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, S-butylsulfinyl, tert-butylsulfinyl, and the like, each selected within the range of the specified number of carbon atoms.
• C a -C b alkylsulfonyl in this specification represents alkyl-SO 2 - having a to b carbon atoms as defined above, and specific examples thereof include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, tert-butylsulfonyl, and the like, each selected within the range of the specified number of carbon atoms.
• C a -C b cycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms, and can form a 3- to 10-membered monocyclic or composite ring structure. Each ring may be optionally substituted with an alkyl group within the specified range of carbon atoms. Specific examples include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, each of which is selected within the specified range of carbon atoms.
• C a -C b alkylamino in the present specification represents an amino in which one of the hydrogen atoms is substituted by alkyl having a to b carbon atoms as defined above, and specific examples thereof include methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, tert-butylamino, etc., each of which is selected within the range of the specified number of carbon atoms.
• di(C a -C b alkyl)amino represents amino in which both hydrogen atoms are substituted with alkyl as defined above, each of which may be the same or different and has a to b carbon atoms, and specific examples thereof include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, di(n-butyl)amino, etc., each of which is selected within the range of the specified number of carbon atoms.
• C a -C b alkylcarbonyl in the present specification represents alkyl-C(O)- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, heptanoyl, and the like, each of which is selected within the range of the specified number of carbon atoms.
• C a -C b haloalkylcarbonyl in the present specification represents haloalkyl-C(O)- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include difluoroacetyl, trichloroacetyl, trifluoroacetyl, etc., each of which is selected within the range of the specified number of carbon atoms.
• C a -C b alkenylcarbonyl in the present specification represents alkenyl-C(O)- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include vinylcarbonyl, 1-propenylcarbonyl, 2-propenylcarbonyl, 1-methylethenylcarbonyl, 2-butenylcarbonyl, 2-methyl-2-propenylcarbonyl, 3-methyl-2-butenylcarbonyl, 1,1-dimethyl-2-propenylcarbonyl, and the like, each selected within the specified range of carbon atoms.
• C a -C b cycloalkylcarbonyl in this specification represents cycloalkyl-C(O)- as defined above having a to b carbon atoms, and specific examples thereof include cyclopropylcarbonyl, 1-methylcyclopropylcarbonyl, 2-methylcyclopropylcarbonyl, 2,2-dimethylcyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, and the like, each selected within the range of the specified number of carbon atoms.
• C a -C b alkoxycarbonyl in the present specification represents alkyl-O-C(O)- as defined above having a to b carbon atoms, and specific examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, 2-ethylhexyloxycarbonyl, and the like, each selected within the range of the specified number of carbon atoms.
• C a -C b haloalkoxycarbonyl in this specification represents haloalkyl-O-C(O)- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include 2,2,2-trichloroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-chloro-2,2-difluoroethoxycarbonyl, 3,3,3-trifluoropropyloxycarbonyl, and the like, each of which is selected within the range of the specified number of carbon atoms.
• C a -C b alkenyloxycarbonyl in the present specification represents alkenyl-O-C(O)- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include vinyloxycarbonyl, 1-propenyloxycarbonyl, 2-propenyloxycarbonyl, 1-methylethenyloxycarbonyl, 2-butenyloxycarbonyl, 2-methyl-2-propenyloxycarbonyl, 3-methyl-2-butenyloxycarbonyl, 1,1-dimethyl-2-propenyloxycarbonyl, and the like, each selected within the specified range of carbon atoms.
• C a -C b alkylcarbonyloxy in the present specification represents alkyl-C(O)-O- having a to b carbon atoms as defined above, and specific examples thereof include acetyloxy, propionyloxy, and pivaloyloxy, each of which is selected within the range of the number of carbon atoms specified.
• C a -C b alkoxycarbonyloxy in the present specification represents alkyl-O-C(O)-O- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include methoxycarbonyloxy, ethoxycarbonyloxy, i-butoxycarbonyloxy, and the like, each selected within the specified range of the number of carbon atoms.
• C a -C b alkylaminocarbonyl in the present specification represents carbamoyl in which one of the hydrogen atoms is substituted by alkyl having a to b carbon atoms as defined above, and specific examples thereof include methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, s-butylcarbamoyl, tert-butylcarbamoyl, and the like, each selected within the range of the specified number of carbon atoms.
• di(C a -C b alkyl)aminocarbonyl in this specification represents carbamoyl in which both hydrogen atoms are substituted with alkyl having a to b carbon atoms, each of which may be the same or different, as defined above.
• Specific examples include N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N,N-di(n-propyl)carbamoyl, N,N-di(n-butyl)carbamoyl, etc., each of which is selected within the range of the number of carbon atoms specified.
• C a -C b alkylaminothiocarbonyl in the present specification represents alkylamino-C( ⁇ S)- as defined above, in which one of the hydrogen atoms has a to b carbon atoms.
• Specific examples thereof include methylthiocarbamoyl, ethylthiocarbamoyl, n-propylthiocarbamoyl, i-propylthiocarbamoyl, n-butylthiocarbamoyl, i-butylthiocarbamoyl, s-butylthiocarbamoyl, tert-butylthiocarbamoyl, and the like, each selected within the specified range of the number of carbon atoms.
• di(C a -C b alkyl)aminothiocarbonyl in this specification represents alkylamino-C( ⁇ S)- as defined above, in which both hydrogen atoms, which may be the same or different, have a to b carbon atoms.
• Specific examples include N,N-dimethylthiocarbamoyl, N-ethyl-N-methylthiocarbamoyl, N,N-diethylthiocarbamoyl, N,N-di(n-propyl)thiocarbamoyl, N,N-di(n-butyl)thiocarbamoyl, and the like, each selected within the range of the specified number of carbon atoms.
• tri(C a -C b alkyl)silyl in this specification represents silyl substituted by alkyl having a to b carbon atoms, which may be the same or different, as defined above. Specific examples include trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl, tert-butyldimethylsilyl, etc., each of which is selected within the range of the number of carbon atoms specified.
• C a -C b alkylcarbonyl substituted with R a refers to alkyl-C(O)- as defined above, in which any hydrogen atom bonded to a carbon atom is partially or completely substituted with one or more substituents R a and the number of carbon atoms is a to b, selected within the range of the number of carbon atoms specified for each group.
• the substituents R a may be the same or different from each other.
• C a -C b alkenylcarbonyl substituted with R a refers to alkenyl-C(O)- as defined above, in which any hydrogen atom bonded to a carbon atom is partially or completely substituted with one or more substituents R a and the number of carbon atoms is a to b, selected within the range of the number of carbon atoms specified for each group. In this case, when there are two or more substituents R a , the substituents R a may be the same or different.
• C a -C b alkoxycarbonyl substituted with R a refers to alkyl-O-C(O)- as defined above, in which any hydrogen atom bonded to a carbon atom is partially or completely substituted with one or more substituents R a and the number of carbon atoms is a to b, selected within the range of the number of carbon atoms specified for each group. In this case, when there are two or more substituents R a , the substituents R a may be the same or different from each other.
• benzyl herein refers to --CH 2 C 6 H 5 .
• benzyloxy herein refers to -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 illustrative, and the compound of the present invention represented by formula (1) may also be produced by other methods.
• the "compound of the present invention represented by formula (1)” will also be described as “compound of the present invention (1),” and the “compound of formula (2)” will also be described as “compound (2).”
• Other compounds will also be described in a similar manner.
• the compound (1) of the present invention can be produced, for example, by the following production method.
• J1 represents a chlorine atom, a bromine atom, a C1 - C4 alkylcarbonyloxy or a C1 - C4 alkoxycarbonyloxy
• G, T, Rx, Ry , R1 , R2 , R3 , W, Z and p are as defined above.
• the compound (1) of the present invention can be produced by reacting compound (2), compound (3) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.), and a dehydration condensation agent in a solvent or without a solvent, and optionally in the presence of either or both of a base and an additive.
• a salt thereof e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluene
• compound (1) of the present invention can also be produced by reacting compound (2-1) with compound (3) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, optionally in the presence of either a base or an additive, or both.
• compound (3) or a salt thereof e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.
• the amount of compound (3) or a salt thereof used may be 0.5 to 50 equivalents per equivalent of compound (2) or compound (2-1).
• the amount of the dehydration condensation agent used may be 0.5 to 50 equivalents per equivalent of compound (2).
• dehydration condensation agents examples include 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N'-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxidehexafluorophosphate, etc.
• the solvent used may be any solvent that is inert to the reaction, and examples thereof include water; alcohol solvents such as methanol, ethanol, and tert-butyl alcohol; ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, and diglyme; aromatic hydrocarbon solvents such as benzene, xylene, and toluene; aliphatic hydrocarbon solvents such as n-pentane, n-hexane, and cyclohexane; halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1,2-dichloroethane; nitrile solvents such as acetonitrile and propionitrile; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and N,N'-dimethylimid
• Bases that can be used in the reaction include, for example, organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) and 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 and potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide.
• the amount of base used (equivalents) can be 0.1 to 100 equivalents per equivalent of compound (2) or compound (2-1).
• Additives that can be used in the reaction include, for example, 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, 4-(dimethylamino)pyridine, etc.
• the amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of compound (2) or compound (2-1).
• the reaction temperature can be set at any temperature between -78°C and the reflux temperature of the reaction mixture.
• the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be set at any time within the range of 5 minutes to 100 hours.
• the compound of the present invention (1-1-1) can be produced, for example, by the following production method.
• L represents a leaving group such as 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 haloalkylsulfonyloxy (e.g., trifluoromethanesulfonyloxy, etc.), or arylsulfonyloxy (e.g., paratoluenesulfonyloxy, etc.), C 1 -C 4 alkylcarbonyloxy, or C 1 -C 4 alkoxycarbonyloxy, and G, T, R X , R Y , R 1 , R 2 , R 3 and Z have the same meanings as above.]
• the compound (1-1-1) of the present invention can be produced by reacting
• the amount of compound (C) used may be 0.5 to 50 equivalents per equivalent of compound (2-5).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2-5).
• Additives that can be used in the reaction include, for example, sodium iodide and potassium iodide.
• the amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of compound (2-5).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound of the present invention (1-1-3) can be produced, for example, by the following production method.
• the compound (1-1-3) of the present invention can also be produced by reacting the compound (1-1-2) of the present invention with the compound (D) or the compound (E) in a solvent or without a solvent, and optionally in the presence of either one or both of a base and an additive.
• the amount of compound (D) or compound (E) used may be 0.5 to 50 equivalents per equivalent of the compound of the present invention (1-1-2).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of the compound of the present invention (1-1-2).
• Additives that can be used in this reaction include, for example, the additives exemplified in Production Example 1.
• the amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of the compound of the present invention (1-1-2).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound of the present invention (1-1-2) can be synthesized according to the method of Production Method 1.
• the compound of the present invention (1-1-5) can be produced, for example, by the following production method.
• R 101 represents C 1 -C 6 alkyl
• G, R x , R y , R 1 , R 2 , R 3 , Z 1 , n4 and p have the same meanings as defined above.
• the compound of the present invention (1-1-5) can be obtained by hydrolyzing the compound of the present invention (1-1-4) in a solvent or without a solvent, and optionally in the presence of a base.
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of the compound of the present invention (1-1-4).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound of the present invention (1-1-4) can be synthesized according to the method of Production Method 1.
• the compound of the present invention (1-1-6) can be produced, for example, by the following production method.
• the compound (1-1-6) of the present invention can be produced by reacting the compound (1-1-5) of the present invention, compound (H) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.), and a dehydration condensation agent in a solvent or without a solvent, and optionally in the presence of either a base or an additive, or both.
• a salt thereof e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.
• the amount of compound (H) or a salt thereof used may be 0.5 to 50 equivalents per equivalent of the compound of the present invention (1-1-5).
• the dehydrating condensation agent that can be used in this reaction includes, for example, the dehydrating condensation agent exemplified in Production Example 1.
• the amount (equivalent) of the dehydrating condensation agent used can be 0.1 to 100 equivalents per equivalent of the compound of the present invention (1-1-5).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of the compound of the present invention (1-1-5).
• Additives that can be used in this reaction include, for example, the additives exemplified in Production Example 1.
• the amount (equivalent) of the additive used can be 0.1 to 100 equivalents per equivalent of the compound of the present invention (1-1-5).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound of the present invention (1-1-7) can be produced, for example, by the following production method.
• Z a1 represents C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl or C 1 -C 6 haloalkyl
• G, R x , R y , R 1 , R 2 , R 3 , Z 1 , n4 and p have the same meanings as above.
• the compound (1-1-7) of the present invention can be produced by reacting the compound (2-7) in a solvent or without a solvent, and optionally in the presence of a base.
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2-7).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound of the present invention (1-1-9) can be produced, for example, by the following production method.
• the compound of the present invention (1-1-9) can be produced by reacting the compound of the present invention (1-1-8) with hydroxylamine or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, and optionally in the presence of a base.
• hydroxylamine or a salt thereof e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of the compound of the present invention (1-1-8).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound of the present invention (1-1-8) can be synthesized according to the method of Production Method 1.
• the compound of the present invention (1-1-10) can be produced, for example, by the following production method.
• the compound (1-1-10) of the present invention can be produced by reacting the compound (1-1-9) of the present invention with a compound (D1) or a compound (E1) in a solvent or without a solvent, and optionally in the presence of a base.
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of the compound of the present invention (1-1-8).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound of the present invention (1-1-11) can be produced, for example, by the following production method.
• the compound (1-1-11) of the present invention can be produced by reacting the compound (2-8) with a dehydrating agent in a solvent or without a solvent.
• dehydrating agents examples include methyl N-(triethylammoniosulfonyl)carbamate.
• the amount (equivalent) of the dehydrating agent used can be 0.1 to 100 equivalents per equivalent of compound (2-8).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound (1-2-2) of the present invention in which W is --N( R.sub.W )-- and R.sub.W is a hydrogen atom can also be produced, for example, by the following production method.
• the compound of the present invention (1-2-2) can be produced by reacting the compound of the present invention (1-2-1) with a nucleophile in the presence of a palladium catalyst in a solvent or without a solvent.
• the amount of the nucleophile used may be 0.5 to 50 equivalents per equivalent of the compound of the present invention (1-2-1).
• Nucleophiles include, for example, morpholine and 1,3-dimethylbarbituric acid.
• palladium catalysts examples include tetrakis(triphenylphosphine)palladium (zero valence).
• the amount (equivalent) of the palladium catalyst used can be 0.001 to 50 equivalents per equivalent of the compound of the present invention (1-2-1).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound of the present invention (1-2-1) can be synthesized according to the method of Production Method 1.
• the compound of the present invention (1-2-4) can also be produced, for example, by the following production method.
• R W' represents C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl substituted with R a , C 2 -C 6 alkenyl, C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenylcarbonyl , C 3 -C 10 cycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonyl substituted with R a , C 2 -C 6 alkenyloxycarbonyl, di(C 1 -C 6 ) alkylaminocarbonyl, di(C 1 -C 6 ) alkylaminothiocarbonyl C 1 -C 6 alkylsulfonyl, or -C(O)OR d ; L, G, T, R X , R Y , R 1 , R 2 , R 3 , R a , R d
• the amount of compound (L) used may be 0.5 to 50 equivalents per equivalent of the compound of the present invention (1-2-2).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of the compound of the present invention (1-2-2).
• Additives that can be used in the reaction include, for example, potassium iodide.
• the amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of the compound of the present invention (1-2-2).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound (1-2-3) of the present invention in which W is --N(R W )-- and R W is --C(W 1 )NHR Wa can also be produced, for example, by the following production method.
• the compound (1-2-3) of the present invention can be produced by reacting the compound (1-2-2) of the present invention with a compound (M) in a solvent or without a solvent, and optionally in the presence of a base.
• the amount of compound (M) used may be 0.5 to 50 equivalents per equivalent of the compound of the present invention (1-2-2).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of the compound of the present invention (1-2-2).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound of the present invention (1-2-5) can also be produced, for example, by the following production method.
• the compound (1-2-5) of the present invention can be produced by reacting the compound (2-9), the compound (N) and a reducing agent in the presence of an acid in a solvent or without a solvent.
• the amount of compound (N) used may be 0.5 to 50 equivalents per equivalent of compound (2-9).
• the amount of the reducing agent used can be 0.5 to 50 equivalents per equivalent of compound (2-9).
• Reducing agents include 2-picoline borane, etc.
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the amount of acid used can be 0.1 to 100 equivalents per equivalent of compound (2-9).
• acids examples include hydrochloric acid and acetic acid.
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound of the present invention (1-2-7) can also be produced, for example, by the following production method.
• R1 ' represents C1 - C6 alkyl or C1- C6 alkyl substituted with R1, and L, G, T, Rx, Ry, R1, R2, R2 , R3 , Rw , Z and p represent the same meanings as above.
• the compound of the present invention (1-2-7) can be produced by reacting the compound of the present invention (1-2-6) with a compound (L1) in the presence of a base in a solvent or without a solvent.
• the amount of compound (L1) used may be 0.5 to 50 equivalents per equivalent of the compound of the present invention (1-2-6).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of the compound of the present invention (1-2-6).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound of the present invention (1-2-6) can be synthesized according to the method of Production Method 1.
• Compound (2) used in Preparation Example 1 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 1.
• Compound (2) can be obtained by reacting compound (2-A) with compound (A) in a solvent or without a solvent in the presence of a base and, if necessary, in the presence of either a copper catalyst or an additive, or in the presence of both, or alternatively in the presence of a base and, if necessary, in the presence of a palladium catalyst and a ligand.
• the amount of compound (A) used may be 0.5 to 50 equivalents per equivalent of compound (2-A).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2-A).
• copper catalysts examples include copper iodide (monovalent), copper trifluoromethanesulfonate (monovalent) benzene complex, and copper trifluoromethanesulfonate (monovalent) toluene complex.
• the amount of the copper catalyst that can be used is 0.001 to 50 equivalents per equivalent of compound (2-A).
• Additives that can be used in this reaction include, for example, N,N-dimethylglycine, 4-(dimethylamino)pyridine, etc.
• the amount (equivalent) of the additive used can be 0.001 to 100 equivalents per equivalent of compound (2-A).
• palladium catalysts examples include palladium (2) ( ⁇ -cinnamyl) chloride (dimer), allylpalladium (2) chloride (dimer), and tris(dibenzylideneacetone)dipalladium (0 valent).
• the amount (equivalent) of the palladium catalyst used can be 0.001 to 50 equivalents per equivalent of compound (2-A).
• Examples of the ligand that can be used in the reaction include 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tert-butyl-XPhos), tetramethyl-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tetramethyldi-tert-butyl-XPhos), 2-di-(tert-butyl)phosphino-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl (RockPhos), 2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl (BrettPhos), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl ( The amount (e
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound (2-1) used in Production Example 1 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 2.
• Compound (2-1) can be obtained by reacting compound (2) with a halogenating agent such as thionyl chloride, phosphorus pentachloride, or oxalyl chloride in accordance with a known method described in the literature, for example, the method described in Journal of Medicinal Chemistry [J. Med. Chem.], 1991, vol. 34, p. 1630, etc.
• a halogenating agent such as thionyl chloride, phosphorus pentachloride, or oxalyl chloride
• compound (2-1) can be obtained by reacting compound (2) with an organic acid halide such as pivaloyl chloride or isobutyl chloroformate in the presence of a base, if necessary, in accordance with the methods described in Tetrahedron Lett., 2003, vol. 44, p. 4819 and Journal of Medicinal Chemistry [J. Med. Chem.], 1991, vol. 34, p. 222, etc.
• organic acid halide such as pivaloyl chloride or isobutyl chloroformate
• the compound (2-2) in which R 1 and Y are hydrogen atoms can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 3.
• Step 1 Compound (2-C) can be obtained by reacting compound (2-B) with compound (B) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, and optionally in the presence of a base.
• a salt thereof e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.
• the amount of compound (B) or a salt thereof used may be 0.5 to 50 equivalents per equivalent of compound (2-B).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2-B).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• Step 2 Compound (2-2) can be obtained by reacting compound (2-C) with an oxidizing agent in a solvent or without a solvent.
• oxidizing agents examples include potassium permanganate.
• the amount (equivalent) of the oxidizing agent used can be 0.1 to 100 equivalents per equivalent of compound (2-C).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• Compound (2-2) can also be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 4.
• Step 1 Compound (2-D) is reacted under the same conditions as in Step 1 of Reaction Scheme 3 to obtain compound (2-E).
• Step 2 Compound (2-2) can be obtained by reacting compound (2-E) with carbon dioxide in the presence of a base, either in a solvent or without a solvent.
• An example of a base that can be used is n-butyllithium.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2-E).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• compound (3-1) in which R 1 is a hydrogen atom, W is -N(R W )-, and p is an integer of 1 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 5.
• Step 1 Compound (3-B) can be produced by reacting compound (3-A) with compound (C) in a solvent or without a solvent, optionally in the presence of either or both of a base and an additive.
• the amount of compound (C) used may be 0.5 to 50 equivalents per equivalent of compound (3-A).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (3-A).
• Additives that can be used in the reaction include, for example, potassium iodide.
• the amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of compound (3-A).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• Step 2 Compound (3-1) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) can be produced by reacting compound (3-B) with hydroxylamine or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, optionally in the presence of a base and/or an additive.
• hydroxylamine or a salt thereof e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (3-B).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• Compound (2-4) can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 6.
• Step 1 Compound (2-F) can be obtained by reacting compound (2-3) with compound (F) in the presence of a base in a solvent or without a solvent.
• the amount of compound (F) used may be 0.5 to 50 equivalents per equivalent of compound (2-3).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2-3).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• Step 2 Compound (2-G) can be obtained by reacting compound (2-F) with compound (G) in a solvent or without a solvent, in the presence of a base, and, if necessary, in the presence of a palladium catalyst and a ligand.
• the amount of compound (G) used may be 0.5 to 50 equivalents per equivalent of compound (2-F).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2-F).
• the palladium catalyst that can be used in this reaction is, for example, the palladium catalyst exemplified in reaction formula 1.
• the amount (equivalent) of the palladium catalyst used can be 0.001 to 50 equivalents per equivalent of compound (2-F).
• the ligands that can be used in this reaction include, for example, the ligands exemplified in reaction formula 1.
• the amount (equivalent) of the ligand used can be 0.001 to 50 equivalents per equivalent of compound (2-F).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• Step 3 Compound (2-4) can be obtained by reacting compound (2-G) in a solvent or without a solvent, and optionally in the presence of a base.
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2-G).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound (2-5) used in Preparation Example 2 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 7.
• Compound (2-5) can be produced by reacting compound (2), hydroxylamine or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.), and a dehydration condensation agent in a solvent or without a solvent, and optionally in the presence of either a base or an additive, or both.
• hydroxylamine or a salt thereof e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.
• compound (2-5) can also be produced by reacting compound (2-1) with hydroxylamine or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, optionally in the presence of a base or an additive, or both.
• hydroxylamine or a salt thereof e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.
• the amount of hydroxylamine or its salt used may be 0.5 to 50 equivalents per equivalent of compound (2) or compound (2-1).
• the dehydrating condensation agent that can be used in this reaction includes, for example, the dehydrating condensation agent exemplified in Production Example 1.
• the amount (equivalent) of the dehydrating condensation agent used can be 0.1 to 100 equivalents per equivalent of compound (2).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in the reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2) or compound (2-1).
• Additives that can be used in this reaction include, for example, the additives exemplified in Production Example 1.
• the amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of compound (2) or compound (2-1).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• Compound (2-9) can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 8.
• Compound (2-9) can be obtained by reacting compound (2-1) with hydrazine monohydrate in the presence of a base, either in a solvent or without a solvent.
• the amount of hydrazine monohydrate used can be 0.5 to 50 equivalents per equivalent of compound (2-1).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• the base that can be used in this reaction includes, for example, the bases exemplified in Production Example 1.
• the amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2-1).
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• Compound (2-6) can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 9.
• Step 1 Compound (2-J) can be obtained by reacting compound (2-H) with a halogenating agent in a solvent or without a solvent.
• Halogenating agents that can be used include, for example, chlorine, N-chlorosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, bromine, N-bromosuccinimide, and N-iodosuccinimide.
• the amount (equivalent) of the halogenating agent used can be 0.1 to 100 equivalents per equivalent of compound (2-H).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• Step 2 Compound (2-K) can be obtained by hydrolyzing compound (2-J) in the presence of an acid such as hydrochloric acid or sulfuric acid or a base such as calcium carbonate or sodium acetate in accordance with a known method described in the literature, for example, the method described in Japanese Patent Application Publication No. 2014/214118 and Journal of Heterocyclic Chemistry, Vol. 29, p. 691, 1992.
• Step 3 Compound (2-6) can be obtained by oxidizing compound (2-K) according to a known method described in the literature, for example, the method described in WO 2008/028688.
• the compound (2-7) used in Preparation Example 6 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 10.
• Compound (2-7) can be obtained by reacting compound (1-1-5) of the present invention with compound (J) in accordance with a known method described in the literature, for example, the method described in WO 2008/156721.
• the compound (2-8) used in Preparation Example 9 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 11.
• Compound (2-8) can be obtained by reacting compound (1-1-5) of the present invention with compound (K) in accordance with a known method described in the literature, for example, the method described in WO 2008/016123.
• Compound (2) can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 11.
• Step 1 Compound (2-M) can be produced by reacting compound (2-L) with a halogenating agent in a solvent or without a solvent.
• halogenating agents examples include the halogenating agents exemplified in step 1 of reaction scheme 9.
• the amount (equivalent) of the halogenating agent used can be 0.1 to 100 equivalents per equivalent of compound (2-L).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compound (2-L) can be synthesized according to the method of Reaction Scheme 3.
• Step 2 Compound (2-N) can be obtained by hydrolyzing compound (2-M) in the presence of water and a base such as sodium hydroxide, potassium hydroxide, or lithium hydroxide in accordance with a known method described in the literature, for example, the methods described in WO 2006/067443 and WO 2023/033142.
• Step 3 Compound (2) can be obtained by reacting compound (2-N) with an oxidizing agent in a solvent or without a solvent, in the presence of a catalyst, and optionally in the presence of either or both of a buffer and an additive.
• oxidizing agents examples include sodium chlorite, an aqueous solution of sodium chlorite, sodium hypochlorite, an aqueous solution of sodium hypochlorite, and sodium hypochlorite pentahydrate.
• the amount of the oxidizing agent used can be 0.001 to 100 equivalents per equivalent of compound (2-N).
• Catalysts that can be used in this reaction include, for example, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), 2-azaadamantane-N-oxyl (AZADO), etc.
• the amount of catalyst used can be 0.001 to 100 equivalents per equivalent of compound (2-N).
• Buffers that can be used in the reaction include, for example, sodium dihydrogen phosphate, sodium dihydrogen phosphate dihydrate, acetic acid, etc.
• the amount of the buffer used can be 0.5 to 100 equivalents per equivalent of compound (2-N).
• Additives that can be used in this reaction include, for example, potassium bromide, tetrabutylammonium bromide, etc.
• the amount of catalyst used can be 0.001 to 100 equivalents per equivalent of compound (2-N).
• the solvent used is inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.
• reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.
• the compounds of the present invention can generally be used as agricultural and horticultural bactericides and fungicides against various diseases caused by fungi, oomycetes, zygomycetes, ascomycetes, basidiomycetes, fungi imperfecti, bacteria, or viruses.
• pathogenic microorganism refers to a microorganism that causes a plant disease, and specific examples thereof include, but are 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., Cerco spora spp.
• Taphrina spp. e.g., Taphrina deformans, T. pruni, etc.
• Pneumocystis spp. Geotrichum spp.
• Candida spp. e.g., Candida
• Cercospora apii Cercospora apii, C. asparagi, C. beticola, C. capsici, C. carotae, C. kaki, C. kikuchii, C. zonata, etc.
• Cercosporidium spp. Cercosporidium spp.
• Cladosporium spp. e.g., Cladosporium colocasiae, C. cucumerinum, C. variabile, etc.
• Davidiella spp. Didymospor ium spp.
• Heterosporium spp. e.g., Heterosporium allii, etc.
• Mycosphaerella spp. e.g., Mycosphaerella arachidis, M.
• 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.
• Pseudocercospora abelmoschi P. fuligena, P. vitis, etc.
• Pseudocercosporella spp. e.g., Pseudocercosporella capsellae, etc.
• Ramichloridium spp. Ramularia spp.
• Septogloeum spp. Septoria spp. (e.g., Septoria albopunctata, S. apiicola, S. chrysanthemella, S. helianthi, S.
• Sphaerulina spp. Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (e.g., Elsinoe ampelina, E. araliae, E. fawcettii, etc.), Sphaceloma spp. (e.g., Sphaceloma caricae, etc.), Ascochyta spp. (e.g., Ascochyta pisi, etc.), Corynespora spp.
• Elsinoe spp. e.g., Elsinoe ampelina, E. araliae, E. fawcettii, etc.
• Sphaceloma spp. e.g., Sphaceloma caricae, etc.
• Ascochyta spp. e.g., Ascochyta
• 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.
• 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. verruculosa, etc.
• Drechslera spp. Pleospora spp. turcica etc.
• Stemphylium spp. e.g. Stemphylium botryosum, S. lycopersici, S.
• Venturia spp. e.g. Venturia carpophila, V. Inaequalis, V. nashicola, V. pirina etc.
• Didymella spp. . 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.
• Botryosphaeria spp. e.g. Botryosphaeria berengeriana f. sp. piricola, B. dothidea, etc.
• Dothiorella spp. Fusicoccum spp., Guignardia spp., Lasiodiplodia spp. (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. phytes, T. rubrum, etc.
• Histoplasma spp. e.g., Blumeria graminis f. sp. hordei, B. g. f. sp. tritici, etc.
• Golovinomyces spp. e.g. Golovinomyces cichoracearum var. latisporus, 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. (e.g. Phyllactinia kakicola, P. mali, P.
• 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.
• Uncinuliella spp. e.g., Uncinuliella simulans var. simulans, U. s. var.
• Blumeriella spp. e.g., Blumeriella jaapii, etc.
• Cylindrosporium spp. Diplocarpon spp. (e.g., Diplocarpon mali, D. mespili, D. rosae, etc.), Gloeosporium spp. (e.g., Gloeosporium minus, etc.), Marssonina spp., Tapesia spp. (e.g., Tapesia acuformis, T. yallundae, etc.), Lachnum spp., Scleromitrula spp., Botryotinia spp.
• Botryotinia fuckeliana, etc. Botrytis spp.
• 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. vaccinii-corymbosi, etc.), Sclerotinia spp. (e.g., Sclerotinia borealis, S.
• Valdensia spp. e.g., Valdensia heterodoxa, etc.
• Claviceps spp. e.g., Claviceps sorghi, C. sorghicola, etc.
• Epichloe spp. Ephelis japonica, Villosiclava virens
• Hypomyces spp. e.g., Hypomyces solani f. sp. mori, H. s. f. sp. pisi, etc.
• Trichoderma spp. e.g. Trichoderma viride, etc.
• raphani F. o. f. sp. spinaciae, F. sporotrichioides, F. solani, F. s. sp. glycines, F. s. f. sp. pisi, F. s. rothecium spp., Trichothecium spp., Verticillium spp. (e.g., Verticillium albo-atrum, V. dahliae, V. longisporum, etc.), Ceratocystis spp. (e.g., Ceratocystis ficicola, C. fimbriata, etc.), Thielaviopsis spp.
• Verticillium spp. e.g., Verticillium albo-atrum, V. dahliae, V. longisporum, etc.
• Ceratocystis spp. e.g., Ceratocystis fic
• Pestalotia spp. e.g., Pestalotia eriobotrifolia, etc.
• Pestalotiopsis spp. e.g., Pestalotiopsis funerea, P. longiseta, P. neglecta, P. theae, etc.
• Physalospora spp. Nemania spp., Nodulisporium spp., Rosellinia spp. (e.g., Rosellinia necatrix, etc.), Monographella spp.
• Phyllachora pomigena, etc. Ellisembia spp., Briosia spp., Cephalosporium spp. (e.g. Cephalosporium gramineum, etc.), Epicoccum spp., Gloeocercospora sorghi, Mycocentrospora spp., Peltaster spp. (e.g. Peltaster fructicola, etc.), Phaeocytostroma spp., Phialophora spp.
• Phakopsora spp. e.g., Phakopsora artemisiae, P. nishidana, P. pachyrhizi, etc.
• Physopella spp. e.g., Physopella ampelopsidis, etc.
• Kuehneola spp. e.g., Kuehneola japonica, etc.
• Phragmidium spp. e.g., Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae, 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. kuehnii, P. melanocephala, P. recondita, P. str iiformis var. striiformis, P. tanaceti var.
• 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
• Uromyces spp. e.g. Uromyces phaseoli var. azukicola, U. p. var. spp., Leucotelium spp., Tranzschelia spp. (e.g., Tranzschelia discolor, etc.), Aecidium spp., Blastospora spp. (e.g., Blastospora smilacis, etc.), Uredo spp., Sphacelotheca spp., Urocystis spp., Sporisorium spp.
• Uromyces spp. e.g. Uromyces phaseoli var. azukicola, U. p. var. spp., Leucotelium spp., Tranzschelia spp. (e.g., Tranzschelia discolor, etc.), Aecidium spp., Blastospora spp. (e.g., Blas
• Ustilago spp. e.g., Ustilago maydis, U. nuda, etc.
• Entyloma spp. Exobasidium spp. (e.g. Exobasidium reticulatum, E. vexans, etc.), Microstroma spp., Tilletia spp. (e.g. Tilletia caries, T. controversa, T. laevis, etc.), Itersonilia spp. (e.g. Itersonilia perplexans, etc.), Cryptococcus spp., Bovista spp. (e.g.
• Lycoperdon spp. e.g. Lycoperdon curtisii, L. perlatum, etc.
• Conocybe spp. e.g. Conocybe apala, etc.
• Marasmius spp. e.g. Marasmius oreades, etc.
• Armillaria spp. Helotium spp.
• Lepista spp. e.g. Lepista subnuda, etc.
• Sclerotium spp. e.g., Sclerotium cepivorum, etc.
• Typhula spp. e.g., Typhula incarnata, T.
• ishikariensis var. ishikariensis, etc. Athelia spp. (e.g., Athelia rolfsii, etc.), Ceratobasidium spp. (e.g., Ceratobasidium cornigerum, etc.), Ceratorhiza spp., Rhizoctonia spp. (e.g., Rhizoctonia solani, etc.), Thanatephorus spp.
• Fungi of the phylum Chitridiomycota such as Olpidium spp.
• Fungi of the phylum Blastocladiomycota such as Physoderma spp.
• Fungi of the subphylum Mucoromycotina such as Choanephora spp., Choanephoroidea cucurbitae, Mucor spp.
• Rhizopus spp. e.g. Rhizopus arrhizus, R. chinensis, R. oryzae, R. stolonifer var. stolonifer, etc.
• Protists of the phylum Cercozoa such as Plasmodiophora spp. (e.g. Plasmodiophora brassicae, etc.), Spongospora subterranea f. sp. Subterranea, etc.
• Aphanomyces spp. e.g., Aphanomyces cochlioides, A. raphani, etc.
• Plasmopara spp. e.g. Plasmopara halstedii, P.
• P. ythium spp. e.g., Pythium afertile, P.
• Gram-positive fungi of the Actinobacteria such as Clavibacter spp. (e.g., Clavibacter michiganensis subsp. michiganensis, etc.), Curtobacterium spp., Leifsonia spp. (e.g., Leifsonia xyli subsp. xyli, etc.), Streptomyces spp. (e.g., Streptomyces ipomoeae, etc.) Gram-positive fungi of the Firmicutes, such as Clostridium sp. Gram-positive bacteria of the phylum Tenericutes, such as Phytoplasma. Rhizobium spp.
• Plant diseases caused by infection and proliferation of these pathogens include, but are not limited to, the following plant diseases.
• Leaf spot (Cercospora asparagi) on asparagus Cercospora leaf spot (Cercospora beticola) on sugar beet
• Frogeye leaf spot (Cercospora capsici) on bell pepper Frogeye leaf spot (Cercospora capsici) on bell pepper
• Purple stain (Cercospora kikuchii) on soybean Brown leaf spot (Mycosphaerella arachidis) on peanut, Cylindrosporium leaf spot (Mycosphaerella cerasella, Blumeriella jaapii) on cherry, Black sigatoka disease (Mycosphaerella fijiensis) on cherry, Yellow sigatoka disease (
• 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.), pepper powdery mildew (Leveillula taurica), pumpkin powdery mildew (Oidium sp., Podosphaera xanthii), bitter melon powdery mildew (Oidium sp.), powdery mildew of persimmon (Phyllactinia kakicola), powdery mildew of burdock
• simulans U. s. var. tandae
• powdery mildew of zucchini and Japanese melon Podosphaera xanthii
• powdery mildew of strawberry Sphaerotheca aphanis var. aphanis
• powdery mildew of watermelon and melon Sphaerotheca fuliginea
• powdery mildew of grape Uncinula necator, U. n. var.
• Botrytis cinerea 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.
• Endothia canker (Cryphonectria parasitica) of chestnuts, Melanose (Diaporthe citri) of citrus, Stem blight (Phomopsis asparagi) of asparagus, Phomopsis canker (Phomopsis fukushii) of pears, Brown spot (Phomopsis vexans) of eggplants, Anthracnose (Discula theae-sinensis) of teas, Valsa canker (Valsa ceratosperma), Blast (Magnaporthe grisea), Crown rot (Strawberry anthracnose, C.
• Bacterial leaf blight (Acidovorax konjaci), Bacterial wilt (Ralstonia solanacearum), peach hole 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. vitians), Black rot of Brassicaceae rot (Xanthomonas campestris pv.
• plum canker Pulm canker
• tea shoot blight Pseudomonas syringae pv. theae
• onion soft rot Dikeya sp., Pectobacterium carotovorum
• fire blight Erwinia amylovora of the Rosaceae subfamily Pear family
• soft rot Pectobacterium carotovorum
• bacterial soft rot Pierotovorum
• control agents for diseases of horticultural crops has progressed, and a wide variety of agents have been put to practical use to date.
• pathogens have acquired drug resistance, and there are an increasing number of cases in which control with existing fungicides that have been used in the past has become difficult.
• some existing agents are highly toxic, and some remain in the environment for long periods of time, which has led to the emergence of problems such as disturbance of the ecosystem.
• the compound of the present invention has excellent control activity against many pathogens and is highly safe for the target crops.
• the compound of the present invention can exert a sufficient control effect even against pathogens that have acquired resistance to existing fungicides.
• the compound of the present invention does not cause phytotoxicity to the target crops, has almost no adverse effects on mammals, fish, and beneficial insects, and has low residual properties and a low burden on the environment.
• the compound of the present invention can also be used as a medical antibacterial agent and an antibacterial agent for animals, used as an antifungal agent or an internal parasite control agent, as an antibacterial and antifungal agent for wood, paper and pulp, adhesives and paints, fibers and leather, and as an industrial fungicide for cooling water channels in manufacturing plants, etc.
• Pathogenic bacteria that may be targeted as medical or veterinary antibacterial agents include, but are not limited to, tinea 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, and gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes.
• tinea 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
• fungal strains that can be used as antibacterial and antifungal agents include, but are not limited to, wood-rotting fungi such as Tyromyces palustris and Coriolus versicolor, and material-deteriorating microorganisms such as Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, Cladosporium cladosporioides, Aureobasidium pullulans, Gliocladium virens, Chaetomium globosum, Fusarium moniliforme, and Myrothecium verrucaria.
• wood-rotting fungi such as Tyromyces palustris and Coriolus versicolor
• material-deteriorating microorganisms such as Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium
• Strains of interest 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 agent for controlling internal parasites in livestock, poultry, pets, etc.
• target internal parasites include, but are not limited to, the following: The genera Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Strongylus, ylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris, and other nematodes; Filariidae nematodes, such as Wuchereria, Brugia, Onchoceca, Dirofilaria, and Loa; Dracunculidae nematodes, such as Deacunculus; Tapeworms such as Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymeno
• Eimeria spp. such as Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria ovinoidalis; Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesia spp., Trichomonadidae spp., Histomanas spp., Giardia spp., Toxoplasma spp., Entamoeba histolytica, Theileria spp., and the like.
• the compounds of the present invention can be used as antifungal agents in addition to being used as agricultural and horticultural fungicides.
• pathogenic bacteria that can be used as antifungal agents include, but are not limited to, the following. Trichophyton rubrum, Trichophyton mentagrophytes and other tinea fungi, Candida albicans and other Candida fungi, Aspergillus fumigatus and other Aspergillus fungi, Cryptococcus neoformas and other Cryptococcus fungi, and the like.
• the compound of the present invention When the compound of the present invention is applied as an agent for controlling plant diseases and plant pests, it is usually mixed with a suitable solid or liquid carrier and, if desired, surfactants, penetrating agents, spreading agents, thickeners, antifreeze agents, binders, anticaking agents, disintegrants, antidecomposition agents, etc. may be added to prepare the compound for practical use in any formulation type, such as a soluble concentrate, emulsifiable concentrate, wettable powder, water soluble powder, water dispersible granule, water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder, granule, gel, etc.
• any of the above formulations in any dosage form can be provided sealed in a water-soluble package.
• Solid carriers include, for example, natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride; synthetic silicic acid and synthetic silicates.
• natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth
• inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride
• synthetic silicic acid and synthetic silicates synthetic silicic acid and synthetic silicates.
• Liquid carriers include, for example, alcohols such as ethylene glycol, propylene glycol, and isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene, and alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone; esters such as ⁇ -butyrolactone; acid amides such as N-methylpyrrolidone and N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil; water; and the like. These solid and liquid carriers may be used alone or in combination of two or more.
• Surfactants include, for example, nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styryl phenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters; anionic surfactants such as alkyl sulfates, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkylnaphthalene sulfonic acid, polyoxyethylene alkylaryl ether sulfates or phosphates, polyoxyethylene s
• the content of these surfactants is not particularly limited, but is generally preferably in the range of 0.05 to 20 parts by weight per 100 parts by weight of the formulation of the present invention containing the surfactant.
• These surfactants may be used alone or in combination of two or more types.
• the compound of the present invention when used as a pesticide, it may be mixed with other herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners, etc. at the time of formulation or spraying, if necessary.
• the types of pesticides to be mixed with the compound of the present invention include, for example, compounds described in The Pesticide Manual, 18th Edition, 2018. Specific examples of their common names are as follows. However, the pesticides to be mixed 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.
• polysulfide benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorph, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, Bordeaux mixture mixture), boscalid, bromoconazole, bupirimate, buthiobate, butylamine, calcium polysulfide, captafol, captan, carbamorph, carbendazim, carboxin, carpropamid, carvone, cheshunt mixture mixture), chinomethionat, chlobenthiazone, chloraniformethane, chloranil, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlorquinox, chlozolinate, climbazole,
• Destrobin mandipropamid, maneb, mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, mepronil, meptyldinocap, metalaxyl, metalaxyl-M, metam, metazoxolone, metconazole e), methasulfocarb, metofuroxam, metyltetraprole, metiram, metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, nabam, naftifine, natamycin, organic nickel bis (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxyquinoline copper, oxpoconazole
• Insecticides abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acinonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb, allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethiphos, azinphos-ethyl, azinphos-methyl, azocyclotin, bacillus thuringiensis thuringiensis), bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate, benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, bioresmethrin, bistrifluron, broflanilide
• Parasitic drugs esfenvalerate, fenpropathrin, fenvalerate, alphacypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox, lambda-cyhalothrin, permethrin, tefluthrin, zeta-cypermethrin, acetamiprid, clothianid Clothianidin, dinotefuran, imidacloprid, nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, diazinon, dichlorvos ), fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvinphos,
• Antifungals such as ketoconazole and miconazole nitrate.
• Antibacterial agents amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, cefapirin, cefazolin, cefquinome, ceftiofur, chlortetracycline, clavulanic acid acid), danofloxacin, difloxacin, dinitolmide, enrofloxacin, florfenicol, lincomycin, lomefloxacin, marbofloxacin, miloxacin, mimycin, nitrapyrin, norfloxacin, octhilinone, ofloxacin, orbifloxacin, oxolinic acid acid), oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate, acetylisovaleryltylosin
• the dosage of the compound of the present invention varies depending on the application site, application time, application method, cultivated crop, etc., but generally, an amount of active ingredient of 0.005 to 50 kg per hectare (ha) is appropriate, with 0.01 to 1 kg being preferable.
• ⁇ emulsion ⁇ Compound of the present invention 0.1-30 parts
• Liquid carrier 45-95 parts
• Surfactant 4.9-15 parts
• Others 0-10 parts
• Examples of other additives include a spreading agent and a decomposition inhibitor.
• Liquid Compound of the present invention: 0.01-70 parts
• Liquid carrier 20-99.99 parts
• Others 0-10 parts
• antifreeze agents, spreading agents, etc. can be mentioned.
• the above formulation is diluted with water 1 to 10,000 times, preferably 100 to 10,000 times, or sprayed undiluted.
• Formulation Example 1 Emulsion Compound No. 1-001 of the present invention 20 parts Methylnaphthalene 55 parts Cyclohexanone 20 parts Sorpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: product name, manufactured by Toho Chemical Industry Co., Ltd.) The above ingredients are mixed uniformly to prepare an emulsifiable concentrate, which is then 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.
• Formulation Example 2 Wettable powder Compound No. 1-001 of the present invention 25 parts Pyrophyllite 66 parts Sorpol 5039 4 parts (anionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) Carplex #80D 3 parts (white carbon: Shionogi & Co., Ltd., product name) Calcium lignin sulfonate 2 parts
• the above ingredients are mixed and ground uniformly to prepare a wettable powder.
• the wettable powder 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.
• Formulation Example 3 Powder Compound of the present invention No. 1-001 3 parts Carplex #80D 0.5 parts (White carbon: Shionogi & Co., Ltd., trade name) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above ingredients are mixed and ground uniformly to obtain a powder. When used, the powder is spread so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
• Formulation Example 4 Granules Compound No. 1-001 of the present invention 5 parts Bentonite 30 parts Talc 64 parts Calcium lignosulfonate 1 part The above ingredients are homogeneously mixed and pulverized, a small amount of water is added, the mixture is stirred and mixed, granulated in an extrusion granulator, and dried to obtain granules. When used, the granules are sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
• Formulation Example 5 Flowable formulation Compound No. 1-001 of the present invention 25 parts Sorpol 3353 5 parts (non-ionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) Lunox 1000C 0.5 parts (anionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) Xanthan gum (natural polymer) 0.2 parts Sodium benzoate 0.4 parts Propylene glycol 10 parts Water 58.9 parts
• the above ingredients except for the active ingredient (the compound of the present invention) are uniformly dissolved, and then the compound of the present invention is added and stirred thoroughly, followed by wet grinding in a sand mill to obtain a flowable agent. When used, the flowable agent is diluted 50 to 20,000 times with water and sprayed so that the amount of the active ingredient becomes 0.005 to 50 kg per hectare.
• Formulation Example 6 Dry flowable formulation Compound No. 1-001 of the present invention 75 parts Hitenol NE-15 5 parts (anionic surfactant: product name, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Vanilex N 10 parts (anionic surfactant: product name, manufactured by Nippon Paper Industries Co., Ltd.) Carplex #80D 10 parts (white carbon: Shionogi & Co., Ltd., product name)
• the above ingredients are mixed and pulverized uniformly, a small amount of water is added, the mixture is stirred and mixed, granulated in an extrusion granulator, and dried to obtain a dry flowable agent. When used, the mixture is diluted 50 to 20,000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare.
• the compounds of the present invention can be applied by foliage spray, soil treatment, seed disinfection, etc., but common methods commonly used by those skilled in the art are also effective.
• the present invention relates to the following [1] to [65].
• G represents G-1
• G-1 represents a structure represented by the following structural formula:
• G 1 represents hydroxy, nitro, cyano, a halogen atom, C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl , C 1 -C 6 alkylsulfonyl or di(C 1 -C 6 alkyl)amino;
• T represents an oxygen atom
• W represents -O- or -N(R W )-
• R X represents C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, benzyl,
• X1 represents a halogen atom, a C1 - C6 alkyl, a C1 - C6 haloalkyl or a C1 - C6 alkoxy;
• each X1 when u5 represents an integer of 2, 3, 4 or 5, each X1 may be the same as or different from each other;
• each X1 when u4 represents an integer of 2, 3 or 4, each X1 may be the same as or different from each other;
• R Y represents a hydrogen atom, a halogen atom or a C 1 -C 6 alkyl group;
• R 1 represents a hydrogen atom, a C 1 -C 6 alkyl or a C 1 -C 6 alkyl substituted with R i ;
• R W is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl substituted with R a, C 2 -C 6 alkenyl,
• R D represents a halogen atom, nitro or C 1 -C 6 alkyl; In the relationship with R D , when t5 represents an integer of 2, 3, 4 or 5, each R D may be the same as or different from each other; R e represents C 1 -C 6 alkyl or C 1 -C 6 alkoxy; R f represents C 1 -C 6 alkyl; R g represents Q-1 to Q-53 or Q-54; R h represents cyano or C 1 -C 6 alkoxy; R i represents cyano or C 1 -C 6 alkoxy; Z represents Z-1 to Z-49 or Z-50; Z-1 to Z-50 each represent a structure represented by the following structural formula:
• Z1 represents that it is substituted on the aromatic ring of Z-1 to Z-50.
• Z a represents a halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted with R 6 , C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy , C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, phenyl, S-1 to S-5 or S-6;
• v5 represents an integer of 2, 3, 4 or 5 in relation to Z a
• each Z a may be the same as or different from each other;
• v4 represents an integer of 2, 3 or 4 in relation to Z a
• each Z a may be the same as or different from each other;
• v3 represents an integer of 2 or 3 relative to Z a
• each Z a may be the same as or different from each other;
• v2 represents an integer of 2 or 3 relative to Z
• Q-1 to Q-54 each represent a structure represented by the following structural formula:
• Zc represents 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 alkoxycarbonyl;
• w5 represents an integer of 2, 3, 4 or 5
• each Zc may be the same as or different from each other
• w4 represents an integer of 2, 3 or 4
• each Zc may be the same as or different from each other;
• Zc when w3 represents an integer of 2 or 3, each Zc may be the same as or different from each other;
• Zc when w2 represents an integer of 2
• each Zc may be the same as or different from each other;
• Zd represents C 1 -C 6 alkyl;
• m5 represents an integer of 0, 1, 2, 3, 4 or 5;
• n2 represents an integer of 0,
• G 1 represents a halogen atom, a C 1 -C 6 alkyl, a C 3 -C 6 cycloalkyl, a C 1 -C 6 haloalkyl, a C 2 -C 6 alkenyl, a C 1 -C 6 alkoxy, a C 1 -C 6 haloalkoxy, a C 1 -C 6 alkylthio, a C 1 -C 6 alkylsulfinyl, a C 1 -C 6 alkylsulfonyl or a di(C 1 -C 6 alkyl)amino;
• R X represents C 1 -C 6 alkyl, R X -1, R X -2, R X -3 or R X -4;
• R Y represents a hydrogen atom or a halogen atom;
• R W is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl
• R 1 represents a hydrogen atom
• R W is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl substituted with R a , C 2 -C 6 alkenyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkylcarbonyl substituted with R a , C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkenylcarbonyl substituted with R a, C 3 -C 10 cycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkoxycarbonyl substituted with R a , C 2 -C 6 alkenyloxycarbonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 alkyl
• G 1 represents a halogen atom, a C 1 -C 6 alkyl, a C 1 -C 6 haloalkyl, a C 1 -C 6 alkoxy, a C 1 -C 6 haloalkoxy , a C 1 -C 6 alkylthio, a C 1 -C 6 alkylsulfinyl, a C 1 -C 6 alkylsulfonyl or a di(C 1 -C 6 alkyl)amino;
• R X represents C 1 -C 6 alkyl, R X -1, R X -2 or R X -3;
• R Y represents a hydrogen atom or a halogen atom;
• R 1 represents a hydrogen atom;
• R2 represents a hydrogen atom or a C1 - C6 alkyl group;
• R3 represents a hydrogen atom;
• Z is Z-1, Z-2, Z-3, Z-4, Z-6, Z
• the pyrazole compound or salt thereof according to the above-mentioned [5], wherein p represents an integer of 1.
• G 1 represents a halogen atom, a C 1 -C 6 alkyl, a C 3 -C 6 cycloalkyl, a C 1 -C 6 haloalkyl, a C 2 -C 6 alkenyl, a C 1 -C 6 alkoxy, a C 1 -C 6 haloalkoxy, a C 1 -C 6 alkylthio, a C 1 -C 6 alkylsulfinyl, a C 1 -C 6 alkylsulfonyl or a di(C 1 -C 6 alkyl)amino;
• R X represents C 1 -C 6 alkyl, R X -1, R X -2, R X -3 or R X -4;
• R Y represents a hydrogen atom or a halogen atom;
• R W is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl
• R 1 represents a hydrogen atom
• R W is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl substituted with R a , C 2 -C 6 alkenyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkylcarbonyl substituted with R a , C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkenylcarbonyl substituted with R a, C 3 -C 10 cycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkoxycarbonyl substituted with R a , C 2 -C 6 alkenyloxycarbonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 alkyl
• W represents -N(R W )-;
• R W represents a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl substituted with R a, C 2 -C 6 alkenyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkylcarbonyl substituted with R a , C 3 -C 10 cycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonyl substituted with R a , C 2 -C 6 alkenyloxycarbonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 alkyl)aminocarbonyl, C 1 -C 6 alkylaminothiocarbonyl, C 1 -C 6 alkylsulfonyl,
• R W represents a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 10 cycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonyl substituted with R a , C 2 -C 6 alkenyloxycarbonyl or -C(O)R g ; R a represents cyano, C 3 -C 10 cycloalkyl or Q-1;
• the pyrazole compound or a salt thereof according to the above-mentioned [11], wherein R g represents Q-1 or Q-11.
• G 1 represents a halogen atom, a C 1 -C 6 alkyl, a C 3 -C 6 cycloalkyl, a C 1 -C 6 haloalkyl, a C 1 -C 6 alkoxy, a C 1 -C 6 haloalkoxy, a C 1 -C 6 alkylthio, a C 1 -C 6 alkylsulfinyl, a C 1 -C 6 alkylsulfonyl or a di(C 1 -C 6 alkyl)amino;
• the pyrazole compound or salt thereof according to any one of the above [1] to [19], wherein m5 represents an integer of 0, 1 or 2.
• G 1 represents a halogen atom, a C 1 -C 6 alkyl, a C 1 -C 6 haloalkyl, a C 3 -C 6 cycloalkyl or a C 1 -C 6 alkoxy;
• m5 represents an integer of 0 or 1
• G1 represents a C1 - C6 haloalkyl
• G represents a halogen atom
• G1 represents C1 - C6 alkyl; The pyrazole compound or salt thereof according to any one of the above [1] to [23], wherein m5 represents an integer of 1.
• G 1 represents a halogen atom, a C 3 -C 6 cycloalkyl or a C 1 -C 6 alkoxy;
• W represents -O-;
• Z represents Z-1;
• Z 1 represents C 1 -C 6 haloalkoxy, -OR j , -C( ⁇ NOH)NH 2 , E-1, E-2, E-3, E-4, E-13, E-14, E-25, E-28, E-37, E-38, E-41 or E-55;
• R j represents C 1 -C 6 alkyl substituted with R 4 ;
• R4 represents E-2 or E-3;
• Z a represents a halogen atom, a C 1 -C 6 alkyl, a C 1 -C 6 alkyl substituted with R 6 , a C 3 -C 10 cycloalkyl or a C 1 -C 6 haloalkyl;
• the pyrazole compound or a salt thereof according to any one of the above [1] to [28], wherein R 6 represents C 1 -C 6 alkoxy.
• Z represents Z-3, Z-4, Z-8, Z-9, Z-17, Z-19, Z-25, Z-27, Z-46, Z-47, Z-49 or Z-50,
• Z 1 represents cyano, a halogen atom, a C 1 -C 6 alkyl, a C 1 -C 6 alkoxy, E-1, E-2, E-3, E-4, E-13 or E-14.
• Z represents Z-9, Z-25, Z-46, Z-47, Z-49 or Z-50;
• Z represents Z-25; The pyrazole compound or a salt thereof according to the above-mentioned [40], wherein Z 1 represents a halogen atom, a C 1 -C 6 alkyl, a C 1 -C 6 alkoxy, E-1, E-2, E-3, E-4, E-13 or E-14.
• Z is Z-1, Z-2, Z-3, Z-4, Z-6, Z-8, Z-9, Z-17, Z-19, Z-25, Z-27, Z-28, Z-34, Z-44, Z-45, Z-46, Z-47, Z- 48, represents Z-49 or Z-50,
• the pyrazole compound or salt thereof according to any one of the above [1] to [28], wherein Z1 represents E-1, E-2, E-3, E-4, E-13, E-14, E-25, E-28, E-37, E-38, E-41 or E-55.
• W represents -N(R W )-;
• Z represents Z-1;
• Z1 represents hydroxy, nitro, cyano, a halogen atom, C1 - C6 alkyl, C1 - C6 haloalkyl, C1 - C6 haloalkoxy, C1 - C6 alkylthio, C1- C6 haloalkylthio, C1 -C6 alkoxycarbonyl, or E-1.
• W represents -O-;
• G 1 represents hydroxy, nitro, cyano, 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, C 1 -C 6 alkylthio or di(C 1 -C 6 alkyl)amino;
• G 1 when m5 represents an integer of 2, 3, 4 or 5, each G 1 may be the same as or different from each other;
• R X represents C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, benzyl, R X -1 to R X -3 or R X -4;
• X1 represents a halogen atom, a C1 - C6 alkyl, a C1 - C6 haloalkyl or
• G 1 represents a halogen atom, a C 1 -C 6 haloalkyl, a C 1 -C 6 alkoxy or a C 1 -C 6 haloalkoxy;
• R X represents C 1 -C 6 alkyl;
• R Y represents a hydrogen atom;
• R 1 represents a hydrogen atom;
• R2 represents a hydrogen atom;
• R3 represents a hydrogen atom;
• Z represents Z-1;
• Z 1 represents a halogen atom, a C 1 -C 6 alkyl or a C 1 -C 6 haloalkyl;
• m5 represents an integer of 0, 1 or 2;
• n5 represents an integer of 0, 1 or 2;
• W represents -O-;
• G 1 represents hydroxy, nitro, cyano, 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 , C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl or di(C 1 -C 6 alkyl)amino;
• R X represents C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, benzyl, R X -1 to R X -3 or R X -4;
• X1 represents a halogen atom, C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1
• G 1 represents a halogen atom, a C 1 -C 6 alkyl, a C 1 -C 6 haloalkyl, a C 1 -C 6 alkoxy, a C 1 -C 6 haloalkoxy , a C 1 -C 6 alkylthio, a C 1 -C 6 alkylsulfinyl, a C 1 -C 6 alkylsulfonyl or a di(C 1 -C 6 alkyl)amino;
• R X represents C 1 -C 6 alkyl, R X -1, R X -2 or R X -3;
• R Y represents a hydrogen atom;
• R 1 represents a hydrogen atom;
• R2 represents a hydrogen atom;
• R3 represents a hydrogen atom;
• Z represents Z-1, Z-3 or Z-4;
• Z 1 represents nitro, cyano, a halogen atom, C 1 -C 6 alky
• W represents -O-;
• G 1 represents hydroxy, nitro, cyano, 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 , C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl or di(C 1 -C 6 alkyl)amino;
• R X represents C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, benzyl, R X -1 to R X -3 or R X -4;
• X1 represents a halogen atom, C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1
• G 1 represents a halogen atom, a C 1 -C 6 alkyl, a C 1 -C 6 haloalkyl, a C 1 -C 6 alkoxy, a C 1 -C 6 haloalkoxy , a C 1 -C 6 alkylthio, a C 1 -C 6 alkylsulfinyl, a C 1 -C 6 alkylsulfonyl or a di(C 1 -C 6 alkyl)amino;
• R X represents C 1 -C 6 alkyl, R X -1, R X -2 or R X -3;
• R Y represents a hydrogen atom or a halogen atom;
• R 1 represents a hydrogen atom;
• R3 represents a hydrogen atom;
• Z represents Z-1, Z-2, Z-3, Z-4, Z-6, Z-8, Z-9, Z-17, Z-19, Z-25, Z-27, Z-34, Z-
• W represents -N(R W )-;
• G 1 represents hydroxy, nitro, cyano, 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, C 1 -C 6 alkylthio, or di(C 1 -C 6 alkyl)amino;
• G 1 when m5 represents an integer of 2, 3, 4 or 5, each G 1 may be the same as or different from each other;
• R X represents C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, benzyl, R X -1, R X -2, R X -3 or R X -4;
• X1 represents a halogen atom or a C1 -C6 alkyl group;
• G 1 represents a halogen atom, a C 1 -C 6 alkyl, a C 1 -C 6 haloalkyl, a C 1 -C 6 alkoxy or a C 1 -C 6 haloalkoxy;
• R X represents C 1 -C 6 alkyl;
• R Y represents a hydrogen atom;
• R 1 represents a hydrogen atom;
• R W is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl substituted with R a, C 2 -C 6 alkenyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkylcarbonyl substituted with R a , C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkenylcarbonyl substituted with R a , C 3 -C
• W represents -N(R W )-;
• G 1 represents hydroxy, nitro, cyano, a halogen atom, C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl , C 1 -C 6 alkylsulfonyl or di(C 1 -C 6 alkyl)amino;
• R X represents C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, benzyl, R X -1, R X
• G 1 represents a halogen atom, a C 1 -C 6 alkyl, a C 3 -C 6 cycloalkyl, a C 1 -C 6 haloalkyl, a C 2 -C 6 alkenyl, a C 1 -C 6 alkoxy, a C 1 -C 6 haloalkoxy, a C 1 -C 6 alkylthio, a C 1 -C 6 alkylsulfinyl, a C 1 -C 6 alkylsulfonyl or a di(C 1 -C 6 alkyl)amino;
• R X represents C 1 -C 6 alkyl, R X -1 to R X -3 or R X -4;
• R Y represents a hydrogen atom;
• R W is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl substituted with R
• W represents -N(R W )-;
• G 1 represents hydroxy, nitro, cyano, a halogen atom, C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl , C 1 -C 6 alkylsulfonyl or di(C 1 -C 6 alkyl)amino;
• R X represents C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkyl, benzyl, R X -1, R X
• G 1 represents a halogen atom, a C 1 -C 6 alkyl, a C 3 -C 6 cycloalkyl, a C 1 -C 6 haloalkyl, a C 2 -C 6 alkenyl, a C 1 -C 6 alkoxy, a C 1 -C 6 haloalkoxy, a C 1 -C 6 alkylthio, a C 1 -C 6 alkylsulfinyl, a C 1 -C 6 alkylsulfonyl or a di(C 1 -C 6 alkyl)amino;
• R X represents C 1 -C 6 alkyl, R X -1 to R X -3 or R X -4;
• R Y represents a hydrogen atom or a halogen atom;
• R W is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C
• An agricultural chemical comprising, as an active ingredient, at least one selected from the pyrazole compounds and salts thereof according to any one of [1] to [62] above.
• a fungicide comprising at least one pyrazole compound and a salt thereof as described in any one of [1] to [62] above as an active ingredient.
• An agricultural and horticultural fungicide comprising at least one pyrazole compound and a salt thereof as an active ingredient, the pyrazole compound and salt thereof being selected from the group consisting of pyrazole compounds and salts thereof as described in any one of [1] to [62] above.
• An antifungal agent comprising, as an active ingredient, at least one selected from the pyrazole compounds and salts thereof according to any one of the above [1] to [62].
• An internal parasite control agent comprising, as an active ingredient, at least one selected from the pyrazole compounds and salts thereof according to any one of [1] to [62] above.
• the medium pressure preparative liquid chromatography described in the synthesis examples was performed using a Yamazen Corporation medium pressure preparative apparatus: YFLC-Wprep (flow rate 18 ml/min, silica gel 40 ⁇ m column).
• the chemical shift values of the proton nuclear magnetic resonance spectrum (hereinafter, referred to as 1 H-NMR) described below were measured using Me 4 Si (tetramethylsilane) as a standard substance at 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 have the following meanings. s: singlet, d: doublet, dd: double doublet, t: triplet, dt: double triplet, q: quartet, dq: double quartet, sep: septet, m: multiplet, br: broad singlet.
• Synthesis Example 2 Synthesis of 1-(tert-butyl)-N-((4-methylbenzyl)oxy)-4-phenoxy-1H-pyrazole-5-carboxamide (Compound No. 1-011) To a mixed solution of 50 mg of 1-(tert-butyl)-N-hydroxy-4-phenoxy-1H-pyrazole-5-carboxamide, 34 mg of 1-(bromomethyl)-4-methylbenzene, 27 mg of sodium iodide, and 90 ⁇ l of N,N-dimethylformamide, 47 mg of N,N-diisopropylethylamine was added under ice cooling, and the mixture was stirred at the same temperature for 3 hours and then at room temperature for 12 hours.
• Synthesis Example 4 Synthesis of 4-(((1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamido)oxy)methyl)benzoic acid (Compound No. 1-088) To a mixed solution of 6.20 g of methyl 4-(((1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamido)oxy)methyl)benzoate and 40 ml of ethanol, a 1 mol/l aqueous sodium hydroxide solution was added at room temperature, and the mixture was stirred at the same temperature for 18 hours. After completion of the reaction, the solvent was distilled off under reduced pressure.
• Step 1 Synthesis of N-((4-((acetimidamideoxy)carbonyl)benzyl)oxy)-1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide
• Step 2 Synthesis of 1-(tert-butyl)-N-((4-(3-methyl-1,2,4-oxadiazol-5-yl)benzyl)oxy)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide
• a mixed solution of N-((4-((acetimidamideoxy)carbonyl)benzyl)oxy)-1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide obtained in step 1 and 3 ml of pyridine was stirred at 80° C. for 6 hours. After stirring, the mixture was stirred at room temperature for 16 hours and at 80° C. for 8 hours.
• Synthesis Example 7 Synthesis of 1-(tert-butyl)-N-((4-(N'-hydroxycarbamimidoyl)benzyl)oxy)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 2-046) To a mixed solution of 2.30 g of 1-(tert-butyl)-N-((4-cyanobenzyl)oxy)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 25 ml of ethanol, 0.66 g of a 50% by mass aqueous hydroxylamine solution was added at room temperature, and the mixture was stirred at 80°C for 4 hours.
• the obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then 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) as an eluent to obtain 82 mg of the target product as an oil.
• Step 1 Synthesis of N-((4-(2-acetylhydrazine-1-carbonyl)benzyl)oxy)-1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide
• 68 mg of 1,1'-carbonyldiimidazole was added under ice cooling, and the mixture was stirred at room temperature for 4 hours.
• Step 2 Synthesis of 1-(tert-butyl)-N-((4-(5-methyl-1,3,4-oxadiazol-2-yl)benzyl)oxy)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide
• a mixed solution of 126 mg of N-((4-(2-acetylhydrazine-1-carbonyl)benzyl)oxy)-1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 4 ml of 1,2-dichloroethane 100 mg of methyl N-(triethylammoniosulfonyl)carbamate was added at room temperature and stirred for 3 hours under reflux conditions.
• Synthesis Example 10 Synthesis of 2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate allyl (Compound No. 10-005) To a mixed solution of 200 mg of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid and 3 ml of dichloromethane, 78 ⁇ l of oxalyl chloride and 19 mg of N,N-dimethylformamide were added successively at room temperature, and the mixture was stirred at the same temperature for 10 minutes.
• the organic layer obtained was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
• the residue obtained was purified by silica gel column chromatography using n-hexane:ethyl acetate [5:1 (volume ratio, the same applies below)] as an eluent, and 318 mg of the target product was obtained as a pale yellow solid. Melting point: 110-113°C.
• Synthesis Example 13 Synthesis of 2-(1-(tert-butyl)-4-phenoxy-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)-N-ethylhydrazine-1-carboxamide (Compound No. 10-015)
• Synthesis Example 14 Synthesis of N'-(4-bromo-2-chlorobenzyl)-1-(tert-butyl)-4-phenoxy-1H-pyrazole-5-carbohydrazide (Compound No. 10-165) 280 mg of 4-bromo-2-chlorobenzaldehyde was added to a mixed solution of 350 mg of 1-(tert-butyl)-4-phenoxy-1H-pyrazole-5-carbohydrazide and 12 ml of methanol at room temperature, and the mixture was stirred at the same temperature for 30 minutes.
• Reference Example 1 Synthesis of 4-iodo-1-phenyl-1H-pyrazole-5-carboxylic acid 2.5 g of N-iodosuccinimide was added to a mixed solution of 2.0 g of 1-phenyl-1H-pyrazole-5-carboxylic acid and 10 ml of acetic acid at room temperature, and the mixture was 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 A mixed solution of 2.4 g of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)but-3-en-2-one, 1.64 g of tert-butylhydrazine hydrochloride, and 25 ml of 1,4-dioxane was stirred at 100° C. for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. 20 ml of water was added to the resulting residue, and the mixture was extracted with n-hexane (20 ml ⁇ 2 times).
• Step 3 Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid
• a mixed solution of 930 mg of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole, 8.5 ml of tert-butyl alcohol, and 4.3 ml of water 1.48 g of potassium permanganate was added at room temperature, and the mixture was stirred at 100° C. for 2 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.
• the aqueous layer of the obtained filtrate was washed with chloroform (20 ml ⁇ 2 times), and then 1 mol/l hydrochloric acid was added until the pH became 1, and the mixture was extracted with chloroform (20 ml ⁇ 2 times).
• the obtained organic layer was washed with water, dehydrated and dried with saturated saline 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 dried under reduced pressure to obtain 209 mg of the target product as a white solid. Melting point: 120-124°C.
• Step 2 Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole
• 20 ml of 1 mol/l hydrochloric acid was added to the reaction mixture at room temperature, and the mixture was extracted with chloroform (30 ml x 2 times).
• the organic layer obtained was washed with water, dehydrated and dried with saturated saline and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
• the residue obtained was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent, and 400 mg of the target product was obtained as a red oil.
• Step 3 Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Under a nitrogen atmosphere, 0.85 ml of a 1.6 mol/l n-butyllithium n-hexane solution was dropped at ⁇ 78° C.
• the resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate:acetic acid (gradient from 74:25:1 to 39:60:1) as an eluent to give 45 mg of the desired product as a colorless solid. Melting point: 124-126°C.
• the reaction mixture was added to a mixed solution of 1.06 g of hydroxylamine hydrochloride, 1.96 g of N,N-diisopropylethylamine, and 30 ml of dichloromethane under ice cooling, and the mixture was stirred at room temperature for 2 hours.
• 1 mol/l hydrochloric acid was added to the reaction mixture, and the mixture was extracted with dichloromethane (10 ml x 1 time).
• the resulting organic layer was dehydrated and dried over saturated saline and then over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure to obtain 1.08 g of the target product as a pale yellow solid. Melting point: 122-124°C.
• Step 2 Synthesis of 1-(2,4-dimethylbenzyl)-2-(9H-fluoren-9-ylidene)hydrazine-1-allyl carboxylate 6.20 g of 1-(chloromethyl)-2,4-dimethylbenzene was added to a mixed solution of 9.71 g of 2-(9H-fluoren-9-ylidene)hydrazine-1-allyl carboxylate, 22.0 g of 35% by mass aqueous tetraethylammonium hydroxide solution, 579 mg of potassium iodide, and 70 ml of tetrahydrofuran at room temperature, and the mixture was stirred at 60° C. for 1 hour.
• Step 3 Synthesis of 1-(2,4-dimethylbenzyl)hydrazine-1-allyl carboxylate
• a mixed solution of 14.5 g of 1-(2,4-dimethylbenzyl)-2-(9H-fluoren-9-ylidene)hydrazine-1-allyl carboxylate and 70 ml of pyridine 9.70 g of hydroxylamine hydrochloride was added at room temperature and stirred at 60° C. for 1 hour. After the reaction was completed, the solvent was distilled off under reduced pressure. 50 ml of water was added to the resulting residue, and the mixture was extracted with diisopropyl ether (100 ml x 1 time).
• the resulting organic layer was washed with water (50 ml x 2 times) and back-extracted with 3 mol/l hydrochloric acid (50 ml x 3 times).
• a 10 mol/l aqueous sodium hydroxide solution was added to the resulting aqueous layer under ice cooling until the pH became 8, and the mixture was extracted with chloroform (50 ml x 3 times).
• the resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure to obtain 7.04 g of the target product as a yellow oil.
• the reaction mixture was added dropwise to a mixed solution of 9.6 ml of hydrazine monohydrate and 100 ml of dichloromethane under ice cooling, and the mixture was stirred at the same temperature for 1 hour. After the reaction was completed, 100 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (100 ml x 2 times). The obtained organic layer was washed with water, dehydrated and dried with saturated saline and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with 20 ml of n-hexane and dried under reduced pressure to obtain 3.69 g of the target product as a white solid. Melting point: 81-83°C.
• Step 2 Synthesis of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate (Compound No. ii-005) Under a nitrogen atmosphere, 0.50 g of methyl (4-(3-bromophenoxy)-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 were added with 0.10 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium (divalent) dichloride at room temperature, and the mixture was stirred at 100°C for 16 hours.
• Step 3 Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid (Compound No. i-036)
• 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 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate and 100 ml of methanol at room temperature, and the mixture was stirred at 45° C. for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure.
• Step 2 Synthesis of 1-(tert-butyl)-3-chloro-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carbaldehyde
• a mixed solution of 7.29 g of 1-(tert-butyl)-3-chloro-5-(dichloromethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole, 16 ml of N,N-dimethylformamide, and 8 ml of water 5.04 g of calcium carbonate was added at room temperature, and the mixture was stirred at 100° C. for 5 hours.
• Step 3 Synthesis of 1-(tert-butyl)-3-chloro-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid 4.00 g of 1-(tert-butyl)-3-chloro-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carbaldehyde, 8.06 g of 2-methyl-2-butene, 30 ml of tert-butanol, and 10 ml of water were added with 3.60 g of sodium dihydrogen phosphate dihydrate and 2.61 g of sodium chlorite (purity: 80 mass%) under ice cooling, and stirred at room temperature for 1 hour.
• Step 2 Synthesis of (1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-yl)methanol
• 2 ml of 1 mol/l aqueous sodium hydroxide solution was added at room temperature, and the mixture was stirred at 80° C. for 1.5 hours.
• 5 ml of water was added at room temperature, and the mixture was extracted with dichloromethane (5 ml ⁇ 1 time).
• Step 3 Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid (1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazol-5-yl)methanol 395 mg, sodium dihydrogen phosphate dihydrate 500 mg, acetonitrile 6 ml and water 4.8 ml mixed solution, 20 mg of 2,2,6,6-tetramethylpiperidine-1-oxyl, 40 ⁇ l of sodium hypochlorite aqueous solution (effective chlorine concentration 8 mass% or more) and 284 mg of sodium chlorite (purity: 80 mass%) in 1.2 ml of water were added in that order at room temperature, and stirred at the same temperature for 19 hours.
• the compounds of the present invention can be synthesized in accordance with the above Synthesis Examples and Reference Examples. Examples of compounds of the present invention produced in the same manner as Synthesis Examples 1 to 15 are shown in Tables 1 to 14, and examples of intermediates produced in the same manner as Reference Examples 1 to 9 are shown in Tables 15 to 18, but the compounds of the present invention and intermediates are not limited to these.
• the substituents represented by S-14a, E-25a, E-28a, E-37a, E-38a, E-41a, E-55a, S-1a, S-4a and S-6a are each represented by the following structures: Represents.
• 1-163(#1): ⁇ 8.86 (br, 1H), 7.48-7.35 (m, 2H), 7.24 (s, 1H), 7.16-7.08 (m, 3H), 7.06-7.01 (m, 1H) , 6.93 (d, J 8.4 Hz, 1H), 4.88 (s, 2H), 1.72 (s, 9H).
• 1-214(#1): ⁇ 9.13-8.94 (m, 1H), 7.60-7.48 (m, 1H), 7.41-6.77 (m, 6H), 6.72-6.58 (m, 2H), 6.49-6.41 ( m, 1H), 5.07 (s, 2H), 3.70 (s, 3H), 2.27 (s, 3H), 1.73 (s, 9H).
• 1-215(#1): ⁇ 9.12-8.93 (m, 1H), 7.60-7.50 (m, 1H), 7.42-6.94 (m, 7H), 6.88-6.74 (m, 2H), 6.50-6.40 ( m, 1H), 5.06 (s, 2H), 3.68 (s, 3H), 1.73 (s, 9H).
• 1-216(#1): ⁇ 8.98-8.78 (m, 1H), 7.59-7.48 (m, 1H), 7.37-6.76 (m, 6H), 6.73-6.58 (m, 2H), 6.51-6.41 ( m, 1H), 5.07 (s, 2H), 3.71 (s, 3H), 1.72 (s, 9H).
• 2-011(#2): ⁇ 8.92-8.84 (m, 1H), 7.59-7.51 (m, 4H), 7.49-7.31 (m, 7H), 7.28-7.25 (m, 1H), 7.15 (s, 1H), 7.13-7.07 (m, 1H), 4.97 (s, 2H), 1.73 (s, 9H).
• 2-032(#1): ⁇ 8.96-8.81 (m, 1H), 7.51-7.21 (m, 5H), 7.19-7.06 (m, 2H), 6.91-6.78 (m, 2H), 4.87 (s, 2H), 4.38-4.24 (m, 2H), 1.72 (s, 9H).
• 2-153(#1): ⁇ 9.00-8.82 (m, 1H), 8.03-7.91 (m, 2H), 7.57-6.96 (m, 7H), 4.99 (s, 2H), 2.94 (t, J 7.5 Hz, 2H), 2.06-1.09 (m, 15H), 0.99-0.78 (m, 3H).
• 10-211(#2): ⁇ 8.00-7.90 (m, 1H), 7.45-7.27 (m, 3H), 7.21-7.05 (m, 3H), 6.97-6.90 (m, 2H), 5.21-5.12 ( m, 1H), 4.02 (d, J 5.4 Hz, 2H), 1.70 (s, 9H).

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