WO2016039459A1 - Composé d'ester d'acide nicotinique, fongicide agricole et horticole et procédé de lutte contre les maladies de plantes - Google Patents

Composé d'ester d'acide nicotinique, fongicide agricole et horticole et procédé de lutte contre les maladies de plantes Download PDF

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WO2016039459A1
WO2016039459A1 PCT/JP2015/075902 JP2015075902W WO2016039459A1 WO 2016039459 A1 WO2016039459 A1 WO 2016039459A1 JP 2015075902 W JP2015075902 W JP 2015075902W WO 2016039459 A1 WO2016039459 A1 WO 2016039459A1
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compound
substituted
alkyl
formula
salt
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晋太朗 佃
将和 芹澤
岩本　拓也
太一 森山
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石原産業株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—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 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N47/06—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 containing —O—CO—O— groups; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a novel nicotinic acid ester compound or a salt thereof, an agricultural and horticultural fungicide containing the compound or a salt thereof as an active ingredient, and a method for controlling plant diseases using the compound or a salt thereof.
  • Patent Documents 1, 5, 6, 7 and 8 describe that 2-aminonicotinic acid ester derivatives are useful as fungicides.
  • Patent Document 2 discloses that 2-aminonicotinic acid benzyl derivatives in which halogen, methyl, methoxy, trifluoromethyl and the like are present on benzyl are useful as herbicides, and 2-aminonicotine protected with paramethoxybenzyl. Acids are described as synthetic intermediates in Patent Document 3 and Non-Patent Document 1, respectively.
  • Patent Document 4 various compounds are described in Patent Document 4 as nicotinic acid ester derivatives having insecticidal and acaricidal action.
  • Patent Documents 1, 5, 6, 7 and 8 only describe a phytopathogenic fungus belonging to a part of Ascomycota as a fungicide. Accordingly, there is a demand for the creation of agricultural and horticultural fungicides that exhibit a high control effect against a wide range of plant pathogens regardless of the application situation.
  • the present invention aims to provide a compound effective for an agricultural and horticultural fungicide that exhibits an excellent control effect against various plant diseases, or a salt thereof, an agricultural and horticultural fungicide, and a method for controlling plant diseases.
  • Patent Documents 2 and 3 and Non-Patent Document 1 do not describe a compound represented by the following formula (I) or a salt thereof according to the present invention.
  • Patent Document 4 does not specifically describe any compound having amino at the 2-position of nicotinic acid ester.
  • the present inventors have found that the compound represented by the formula (I) or a salt thereof has useful properties as an agricultural and horticultural fungicide and is useful for various plant diseases.
  • the present invention was completed by obtaining knowledge that an excellent control effect was exhibited.
  • R A is COR a , COOR a , CONR a R b , SO 2 R a or SO 2 NR a R b ,
  • R B is hydrogen, COR a , COOR a , alkyl, cycloalkyl, or haloalkyl;
  • R C is hydrogen, alkyl, phenyl or cycloalkyl;
  • R D is alkyl;
  • R a is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, alkoxyalkyl, aryl-alkyl, heterocycle-alkyl, cycloalkyl-alkyl, cycloalkyl, aryl or a heterocyclic group;
  • R b is hydrogen, alkyl, haloalkyl or cycloalkyl;
  • R 2 is hydrogen, alkyl,
  • Y 3 is selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, dialkylamino, alkylamino, amino, alkylthio, alkylsulfinyl, alkylsulfonyl and cyano;
  • W is the formula: -W A -W B -W C- [Where: W A , W B and W C are each independently a bond, CHQ 1 , O, C ( ⁇ O), S (O) n or NQ 1 ;
  • Q 1 is hydrogen or alkyl;
  • n is an integer of 0, 1 or 2],
  • Z is one or more of which may be substituted carbocyclic group in Y 1, one or more of Y 1 is substituted with a which may heterocyclic group or one or more of Y 2 in which may be substituted hydrocarbon group
  • Y 2 is halogen, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, trialkylsilyl, nitro, cyano, dialkylamino, alkylamino, amino, hydroxy, formyl, dioxolanyl, dioxanyl, cycloalkyl, phenyl Selected from the group consisting of thienyl, pyridyl, phenoxy and pyridyloxy, When there are a plurality of R A , R B , R a , R b , R E , Y 3 , Q 1 , Y 1 or Y 2 , they may be the same or different from each other; However, (1) A is 1 or more Y 3 has been or pyridyl substituted with phenyl which may be substituted or one or more Y 3 in, W is is O, and
  • R 2 in the formula (I) is amino;
  • A is selected from the group consisting of pyridine, pyrimidine, pyridazine, pyrazine, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, tetrazole, oxazole, isoxazole, thiazole, isothiazole, crosslinkable piperidine and crosslinkable cycloalkane.
  • the compound or a salt thereof according to ⁇ 1>, wherein the ring may be substituted with one or more Y 3 .
  • R 2 in the formula (I) is amino; Z is substituted with one or more halogen, hydroxy, alkoxy, haloalkoxy, formyl, amino, alkylamino, dialkylamino, alkylthio, haloalkylthio, dioxolanyl or dioxanyl, substituted with one or more Y 1 Te good heterocyclic group, one or more has been or cycloalkyl substituted with Y 1, is which may alkynyl substituted with one or more Y 2 alkenyl may be substituted or with one or more Y 2
  • R 2 in the formula (I) is amino; In order from the side where W is bonded to A, CH 2 , CH 2 O, CHQ 1 OCHQ 1 , S or NQ 1 ; The compound or a salt thereof according to ⁇ 1>, wherein Z is phenyl which may be substituted with one or more Y 1 .
  • R 2 in the formula (I) is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or halogen, which may be substituted with one or more R E , The compound or a salt thereof according to ⁇ 1>, wherein A is a cycloalkane which may be cross-linked.
  • R 2 in the formula (I) is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or halogen which may be substituted with one or more R E ,
  • R 2 in the formula (I) is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or halogen, which may be substituted with one or more R E , W is O, Z is cycloalkyl substituted with one or more Y 1, one or more of Y 1 is substituted by by or 3 or 4-membered heterocyclic group, having 4 to 6 alkenyl or 1 or more carbon
  • the compound or a salt thereof according to the above ⁇ 1> which is alkyl having 2 to 6 carbon atoms substituted with dioxolanyl or dioxanyl.
  • R 2 in the formula (I) is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or halogen, which may be substituted with one or more R E , W is S or NQ 1 ,
  • Z is a hydrocarbon group which may be substituted with one or more Y 2 , or a cycloalkyl substituted with one or more Y 1 .
  • ⁇ 12> A method for controlling plant diseases by applying the compound according to any one of ⁇ 1> to ⁇ 10> or a salt thereof to a plant or soil.
  • the compound of the present invention has a high control effect against various plant diseases.
  • C n and C mn are both natural numbers
  • carbon number n and “carbon number m to n” (m and n are both natural numbers), respectively. It is synonymous. “Equivalent” means molar equivalent.
  • the present invention relates to a compound represented by the following formula (I) or a salt thereof (hereinafter sometimes collectively referred to as “the present compound”).
  • the present invention also relates to an agricultural and horticultural fungicide containing the compound of the present invention as an active ingredient, and further relates to a method for controlling plant diseases by applying the compound of the present invention to plants or soil.
  • R A is COR a , COOR a , CONR a R b , SO 2 R a or SO 2 NR a R b ,
  • R B is hydrogen, COR a , COOR a , alkyl, cycloalkyl, or haloalkyl;
  • R C is hydrogen, alkyl, phenyl or cycloalkyl;
  • R D is alkyl;
  • R a is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, alkoxyalkyl, aryl-alkyl, heterocycle-alkyl, cycloalkyl-alkyl, cycloalkyl, aryl or a heterocyclic group;
  • R b is hydrogen, alkyl, haloalkyl or cycloalkyl;
  • R 2 is hydrogen, alkyl,
  • Y 3 is selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, dialkylamino, alkylamino, amino, alkylthio, alkylsulfinyl, alkylsulfonyl and cyano;
  • W is the formula: -W A -W B -W C- [Where: W A , W B and W C are each independently a bond, CHQ 1 , O, C ( ⁇ O), S (O) n or NQ 1 ;
  • Q 1 is hydrogen or alkyl;
  • n is an integer of 0, 1 or 2],
  • Z is one or more of which may be substituted carbocyclic group in Y 1, one or more of Y 1 is substituted with a which may heterocyclic group or one or more of Y 2 in which may be substituted hydrocarbon group
  • Y 2 is halogen, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, trialkylsilyl, nitro, cyano, dialkylamino, alkylamino, amino, hydroxy, formyl, dioxolanyl, dioxanyl, cycloalkyl, phenyl Selected from the group consisting of thienyl, pyridyl, phenoxy and pyridyloxy, When there are a plurality of R A , R B , R a , R b , R E , Y 3 , Q 1 , Y 1 or Y 2 , they may be the same or different from each other; However, (1) A is 1 or more Y 3 has been or pyridyl substituted with phenyl which may be substituted or one or more Y 3 in, W is is O, and
  • halogen or the halogen as a substituent include fluorine, chlorine, bromine and iodine.
  • the number of halogens as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen may be the same or different.
  • the halogen substitution position may be any position.
  • the hydrocarbon group means alkyl, alkenyl or alkynyl.
  • the alkyl or the alkyl moiety may be linear or branched, and specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl. , tert- butyl, pentyl, and the like as a C 1-6, such as hexyl.
  • the alkenyl or alkenyl moiety may be linear or branched, and specific examples thereof include vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, C 2 such as 2-butenyl, 3-butenyl, 1,3-butadienyl, 3-methyl-2-butenyl, 3-pentenyl, 3-methyl-2-pentenyl, 4-methyl-3-pentenyl, 1-hexenyl -6 and so on.
  • alkynyl or alkynyl moiety may be linear or branched, and specific examples thereof include ethynyl, propargyl, 2-butynyl, 2-pentynyl, and 3-pentyne. Examples include C 2-7 such as -2-yl, 3-hexynyl and 4,4-dimethyl-2-pentynyl.
  • the carbocyclic group represents cycloalkyl or aryl.
  • examples of cycloalkane include C 3-6 such as cyclopropane, cyclobutane, cyclopentane and cyclohexane, which may be bridged, and have a benzene ring and a condensed ring. It may be formed. Examples of such a condensed ring include indane, 5,6,7,8-tetrahydronaphthalene and the like.
  • the cycloalkyl includes a group obtained by removing a hydrogen atom from the ring exemplified as the cycloalkane.
  • examples of the aryl or aryl moiety include those of C 6-10 such as phenyl and naphthyl.
  • a heterocycle or a heterocycle moiety is a 3- to 8-membered heterocycle or fused heterocycle containing 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur.
  • a ring which may be bridged or substituted with an oxo group ( ⁇ O).
  • Examples of the 3- to 8-membered heterocycle include a 3-membered ring such as aziridine, a 4-membered ring such as azetidine and oxetane, pyrrolidine, pyrrole, imidazole, pyrazole, triazole, tetrazole, furan, tetrahydrofuran, oxazole, isoxazole, thiophene, 5-membered rings such as thiazole, isothiazole, thiadiazole, dioxolane, 6-membered rings such as pyran, dihydropyran, piperidine, morpholine, thiomorpholine, thiazine, pyridine, pyrimidine, pyrazine, pyridazine, triazine, dioxane, 7-members such as azepan And condensed heterocycles include indole, quinoline, isoquinoline, benzothiazole, be
  • alkylene examples include linear or branched C 1-4 such as methylene, ethylene, trimethylene, tetramethylene, methylmethylene and dimethylmethylene.
  • R 2 R alkyl which may be substituted with R E represented by 3 or R 4 may each have a substituent represented by one to seven R E at substitutable positions. When there are two or more substituents, each substituent may be the same or different.
  • A is benzene, pyridine, pyrimidine, pyridazine, pyrazine, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, tetrazole, oxazole, isoxazole, thiazole, isothiazole, piperidine, cycloalkane which may be cross-linked and piperidine which may be cross-linked And each of the substitutable positions may have 1 to 11 substituents represented by Y 3 . When there are two or more substituents, each substituent may be the same or different.
  • the cycloalkane which may be cross-linked and the piperidine which may be cross-linked include cycloalkane or piperidine which may be cross-linked with alkylene at any position, and specific examples thereof include norbornane and bicyclo [1.1.1] pentane. , Bicyclo [2.2.2] octane, bicyclo [3.2.1] octane, quinuclidine, 3-azabicyclo [3.2.1] octane, 8-azabicyclo [3.2.1] octane, and the like. .
  • Z is substituted with Y 1 which may carbocyclic group, a substituted substituted hydrocarbon group may be a substituted heterocyclic group, or Y 2 in Y 1, ⁇ 1 at substitutable positions, respectively 11 pieces of Y It may have a substituent represented by 1 or Y 2 , and when there are 2 or more substituents, each substituent may be the same or different.
  • the salt of the compound of the formula (I) includes any salt that is acceptable in the technical field.
  • a salt with an inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or the like.
  • Salt with organic carboxylic acid such as tartaric acid, formic acid, acetic acid, citric acid, fumaric acid, maleic acid, trichloroacetic acid, trifluoroacetic acid; methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, mesitylenesulfonic acid, naphthalene
  • salts with sulfonic acids such as sulfonic acids.
  • the compound of formula (I) or a salt thereof may be in the form of a hydrate.
  • the compound of the present invention may have isomers such as geometric isomers, tautomers and optical isomers, and the present invention includes both isomers and isomer mixtures.
  • isomers are described as a mixture unless otherwise specified.
  • the present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field.
  • A is benzene, pyridine, pyrimidine, pyridazine, pyrazine, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, tetrazole, oxazole, isoxazole, thiazole, isothiazole, cross-linked piperidine or cross-linked cyclo
  • the compound or a salt thereof according to any one of [1] to [9], which is an alkane.
  • Z is 1 or more Y 1 is substituted with with or carbocyclic group or one or more of Y 1 is substituted with a which may heterocyclic group, any of [1] to [11] Or a salt thereof.
  • Z may be substituted with one or more Y 1 , phenyl, naphthyl, cyclopentyl, cyclohexyl, indaryl, 5,6,7,8-tetrahydronaphthyl, pyridyl, pyrimidinyl, pyridazyl, pyrazyl, furyl, Thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, tetrahydrofuryl, indolyl, quinolyl, isoquinolyl, 2-oxo-2H-chromenyl
  • R 2 is alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio, amino, NR A R B or halogen substituted with one or more R E , and A is phenyl or pyridyl , W is a O, Z is 1 or more substituted with Y 1 which may be phenyl or one or more has been or pyridyl substituted with Y 1, compound or its salt of [1] .
  • At least one of R 3 and R 4 is alkyl or halogen substituted with one or more R E , A is phenyl or pyridyl, W is O, Z is 1 or more is has been or pyridyl substituted with phenyl which may be substituted or one or more Y 1 in Y 1, compound or a salt thereof of [1].
  • at least one of R 5 and R 6 is halogen, A is phenyl or pyridyl, W is O, Z is phenyl optionally substituted by one or more Y 1 , or The compound of the above-mentioned [1] or a salt thereof, which is pyridyl optionally substituted with one or more Y 1 .
  • R 5 and R 6 are both alkyl, A is phenyl or pyridyl, W is O, Z is phenyl optionally substituted with one or more Y 1 or 1 or a or pyridyl substituted with more Y 1, compound or a salt thereof of [1].
  • A is phenyl
  • W is a bond or O
  • Z may be substituted with Y 2
  • R 1 is NHCOR a , A is phenyl, W is a bond or O, and Z is not methyl optionally substituted with fluorine, or a compound thereof salt.
  • R 1 is NHCOR a , A is phenyl, W is a bond or O, Z is a carbocyclic group which may be substituted with one or more Y 1 , or 1 or The compound of the above-mentioned [2] or a salt thereof, which is a heterocyclic group which may be further substituted with Y 1 .
  • R 1 is NHCOR a , A is phenyl, W is a bond or O, and Z may be substituted with one or more Y 2 , C 2-6 Alkyl, alkenyl having 2 to 6 carbons or alkenyl having 2 to 7 carbons, and Y 2 is chlorine, bromine, iodine, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, trialkylsilyl Nitro, cyano, dialkylamino, alkylamino, amino, cycloalkyl, phenyl, thienyl, pyridyl, phenoxy and pyridyloxy, the compound of the above-mentioned [2] or a salt thereof.
  • R 2 is alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio, amino, NR A R B or halogen substituted with one or more R E , and A is phenyl or pyridyl , W is a O, Z is not a may pyridyl substituted with one or more Y 1 which may phenyl and substituted with one or more of Y 1, of the [2] or [3] Compound or salt thereof.
  • At least one of R 3 and R 4 is alkyl or halogen substituted with one or more R E , A is phenyl or pyridyl, W is O, Z is 1 or more Y not be pyridyl substituted 1 has been or phenyl and one or more Y 1 substituted with a compound or a salt thereof of [2] or [3].
  • R 2 is alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio, amino, NR A R B or halogen substituted with one or more R E , and A is phenyl or pyridyl , W is O, and Z may be substituted with one or more Y 1 , naphthyl, cyclopentyl, cyclohexyl, indaryl, 5,6,7,8-tetrahydronaphthyl, pyrimidinyl, pyridazyl, pyrazyl, furyl , Thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, tetrahydrofuryl, indolyl, quinolyl, isoquinolyl, 2-ox
  • At least one of R 3 and R 4 is alkyl or halogen substituted with one or more R E ,
  • A is phenyl or pyridyl
  • W is O
  • Z is 1 or more may be substituted with Y 1, naphthyl, cyclopentyl, cyclohexyl, Indariru, 5,6,7,8-tetrahydronaphthyl, pyrimidinyl, pyridazinyl, pyrazinyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl Oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, tetrahydrofuryl, indolyl, quinolyl, isoquinolyl, 2-oxo-2H-chromenyl, 4-oxo-4H-chromenyl, 2-oxo-2,3-di
  • R 2 is alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio, amino, NR A R B or halogen substituted with one or more R E , and A is phenyl or pyridyl , W is O, and Z is a hydrocarbon group which may be substituted with one or more Y 2 , or a compound or a salt thereof according to [2] or [3].
  • At least one of R 3 and R 4 is alkyl or halogen substituted with one or more R E ,
  • A is phenyl or pyridyl, W is O,
  • Z is 1 Or a compound of the above [2] or [3] or a salt thereof, which is a hydrocarbon group which may be substituted with more Y 2 .
  • R 2 is alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio, amino, NR A R B or halogen substituted with one or more R E , wherein A is one or more Phenyl substituted with Y 3 or pyridyl substituted with one or more Y 3 , W is O, Z is phenyl optionally substituted with one or more Y 1 and 1 or more The compound or a salt thereof according to any one of the above [1] to [3], which is not pyridyl which may be substituted with the above Y 1 .
  • At least one of R 3 and R 4 is alkyl or halogen substituted with one or more R E , and A is phenyl substituted with one or more Y 3 or one or more a of Y 3-pyridyl substituted by, W is a O, Z is not the one or more Y 1 which may phenyl and substituted with one or more of the pyridyl may be substituted with Y 1 Any one of the above-mentioned [1] to [3] or a salt thereof.
  • R 2 is alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio, amino, NR A R B or halogen substituted with one or more R E , and A is one or more Naphthyl, cyclopentyl, phenyl substituted with Y 3 or pyridyl substituted with one or more Y 3 , W is O, and Z may be substituted with one or more Y 1 , Cyclohexyl, indaryl, 5,6,7,8-tetrahydronaphthyl, pyrimidinyl, pyridazyl, pyrazyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, tetrahydrofuryl, ind
  • At least one of R 3 and R 4 is alkyl or halogen substituted with one or more R E and A is phenyl substituted with one or more Y 3 or one or more Naphthyl, cyclopentyl, cyclohexyl, indaryl, 5,6,7,8-, which is pyridyl substituted with Y 3 , W is O, and Z may be substituted with one or more Y 1 Tetrahydronaphthyl, pyrimidinyl, pyridazyl, pyrazyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, tetrahydrofuryl, indolyl, quinolyl, isoquinolyl, 2-oxo-2H-chromenyl, 4- Oxo
  • R 2 is alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio, amino, NR A R B or halogen substituted with one or more R E , wherein A is one or more Phenyl substituted with Y 3 or pyridyl substituted with one or more Y 3 , W is O, and Z is a hydrocarbon group optionally substituted with one or more Y 2 Any one of the above-mentioned [1] to [3] or a salt thereof.
  • At least one of R 3 and R 4 is alkyl or halogen substituted with one or more R E , and A is phenyl substituted with one or more Y 3 or one or more Any one of [1] to [3] above, which is pyridyl substituted with Y 3 , W is O, and Z is a hydrocarbon group which may be substituted with one or more Y 2. Or a salt thereof.
  • Y 2 is halogen, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, trialkylsilyl, nitro, cyano, dialkylamino, alkylamino, amino, cycloalkyl, phenyl, thienyl, pyridyl, The compound or a salt thereof according to any one of [1] to [40], selected from the group consisting of phenoxy and pyridyloxy.
  • [1 ′] A compound of formula (I) or a salt thereof, wherein R 2 is alkylthio or NR A R B.
  • [2 ′] A compound of the formula (I) or a salt thereof, wherein R 1 is NR A R B and R 2 is amino.
  • R 2 is amino
  • A is pyridine, pyrimidine, pyridazine, pyrazine, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, tetrazole, oxazole, isoxazole, thiazole, isothiazole, piperidine which may be cross-linked and A compound of the formula (I) or a salt thereof, which is one ring selected from the group consisting of cycloalkanes which may be bridged, wherein said ring may be substituted with one or more Y 3 .
  • R 2 is amino and Z is substituted with one or more of halogen, hydroxy, alkoxy, haloalkoxy, formyl, amino, alkylamino, dialkylamino, alkylthio, haloalkylthio, dioxolanyl or dioxanyl alkyl, one or more of Y 1 is substituted with a which may heterocyclic group, one or more of Y 1 in which may be substituted cycloalkyl, one or more of Y 2 which may alkenyl or one or a substituted by A compound of the formula (I) or a salt thereof which is alkynyl which may be substituted with Y 2 above.
  • R 2 is amino
  • W is CH 2 , CH 2 O, CHQ 1 OCHQ 1 , S or NQ 1 in that order from the side where W is bonded to A
  • Z is 1 or more Y 1
  • R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy or halogen optionally substituted with one or more R E , and A is a cycloalkane which may be bridged Or a salt thereof.
  • R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy or halogen which may be substituted with one or more R E , and OC ( ⁇ O ), NQ 1 C ( ⁇ O), CHQ 1 OCHQ 1 , CHQ 1 OC ( ⁇ O) or CHQ 1 NQ 1 C ( ⁇ O) or a salt thereof.
  • R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or halogen, optionally substituted by one or more R E , W is O, and Z is one or more Y substituted cycloalkyl with 1, one or more Y 1 in which may be substituted 3 or 4-membered heterocyclic group, C 4-6 alkenyl or 1 or the more, C 2 substituted with dioxolanyl or dioxanyl A compound of formula (I) or a salt thereof which is -6 alkyl.
  • R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy or halogen optionally substituted by one or more R E , W is S or NQ 1 , Z is 1 Or a compound of formula (I) or a salt thereof which is a hydrocarbon group optionally substituted with more Y 2 or a cycloalkyl substituted with one or more Y 1 .
  • [10 ′] The compound of [1 ′] or a salt thereof, wherein R 2 is NR A R B. [11 '] or a salt thereof A is the [10 is pyridyl may be substituted with phenyl which may be substituted or one or more Y 3 in one or more of Y 3']. [12 ′] The compound of [10 ′] or a salt thereof, wherein R 1 is NH 2 or NR A R B. [13 '] or a salt thereof A is the [2 is pyridyl may be substituted with one or more Y 3 phenyl may be substituted with or one or more of Y 3'].
  • [14 ′] The compound of [2 ′] or a salt thereof, which is O, CH 2 , CH 2 O, or CHQ 1 OCHQ 1 in this order from the side where W is bonded to A.
  • [15 '] or a salt thereof A is the [3 thienyl which may be substituted with one or more Y 3-pyridyl may be substituted with or one or more of Y 3'].
  • [16 ′] The compound of [3 ′] or [4 ′] or a salt thereof, wherein W is O or CH 2 .
  • [17 ′] The compound according to [5 ′] or a salt thereof, which is CH 2 , CH 2 O, or CHQ 1 OCHQ 1 in this order from the side where W is bonded to A.
  • [18 ′] The compound of [7 ′] or [8 ′] or a salt thereof, wherein R 2 is hydrogen or alkyl optionally substituted with one or more R E.
  • [19 ′] A hydrate of the compound according to any one of [1 ′] to [18 ′] or a salt thereof.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A, W and Z are as described above, and X 1 is hydroxy, alkoxy or halogen.
  • the production method [1] can be usually carried out by reacting the compound of formula (II) with the compound of formula (III) in the presence of a base and a solvent.
  • the compound of the formula (II) and the compound of the formula (III) can be produced according to a known method or by the method described later, or commercially available products may be used.
  • the compound of the formula (III) can be used in a ratio of 1 to 50 equivalents, desirably 1 to 5 equivalents, relative to 1 equivalent of the compound of the formula (II).
  • the base used in this reaction is not particularly limited as long as the reaction proceeds.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate; sodium methoxide, sodium ethoxide, potassium tertiary butoxide
  • alkali metal alkoxides alkali metal hydrogen carbonates such as sodium hydrogen carbonate
  • alkaline earth metal carbonates such as calcium carbonate
  • metal hydroxides such as sodium hydroxide and potassium hydroxide
  • sodium hydride Metal hydrides such as potassium hydride
  • organic amines such as triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, and the like.
  • the base can be used in an amount of 1 to 20 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (III).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually 0 ° C. to 200 ° C., desirably 50 to 120 ° C.
  • the reaction time is usually 1 to 48 hours.
  • the reaction of the production method [1] can be performed by adding an additive or a base as necessary in the presence of a condensing agent and a solvent.
  • a condensing agent examples include carbonyldiimidazole (CDI), N, N′-dicyclohexylcarbodiimide (DCC), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDC), chlorocarbonates, etc.
  • CDI carbonyldiimidazole
  • DCC N, N′-dicyclohexylcarbodiimide
  • EDC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride
  • chlorocarbonates etc.
  • the condensing agent can be used in a proportion of 1 to 10 equivalents, preferably 1 to 3 equivalents, relative to 1 equivalent of the compound of formula (II).
  • Examples of the additive include 1-hydroxybenzotriazole monohydrate (HOBt).
  • the additive can be used in a proportion of 0.1 to 10 equivalents, preferably 0.5 to 3 equivalents, relative to 1 equivalent of the compound of formula (II).
  • Examples of the base include organic amines such as triethylamine, diisopropylethylamine, pyridine, and 4- (N, N-dimethylamino) pyridine.
  • the base can be used in an amount of 1 to 20 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (III).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonitrile
  • the reaction temperature is usually 0 ° C. to 200 ° C., desirably 50 ° C. to 150 ° C.
  • the reaction time is usually 1 to 48 hours.
  • the reaction of the production method [1] can also be performed by reacting in the presence of azodicarboxylic acids, phosphines and a solvent.
  • azodicarboxylic acids include diethyl azodicarboxylate (DEAD), diisopropyl azodicarboxylate (DIAD), N, N, N ′, N′-tetramethylazodicarboxamide (TMAD), 1,1 ′-(azo And dicarbonyl) dipiperidine (ADDP).
  • phosphines include triphenylphosphine and phenoxydiphenylphosphine.
  • phospholanes such as cyanomethylenetributylphosphorane can be used instead of azodicarboxylic acids and phosphines.
  • Azodicarboxylic acids can be used in a proportion of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (III).
  • the phosphines can be used at a ratio of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (III).
  • the phosphoranes can be used in a proportion of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (III).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually 0 ° C. to 200 ° C., preferably 10 to 100 ° C.
  • the reaction time is usually 1 to 48 hours.
  • the reaction of the production method [1] can also be performed in the presence of a halogenating agent, a base and a solvent.
  • a halogenating agent include thionyl chloride, thionyl bromide, phosphorus oxychloride, phosphorus oxybromide and the like.
  • the halogenating agent can be used in a proportion of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (III).
  • the base used in this reaction is not particularly limited as long as the reaction proceeds.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate; sodium methoxide, sodium ethoxide, potassium tertiary butoxide
  • alkali metal alkoxides alkali metal hydrogen carbonates such as sodium hydrogen carbonate
  • alkaline earth metal carbonates such as calcium carbonate
  • metal hydroxides such as sodium hydroxide and potassium hydroxide
  • sodium hydride And metal hydrides such as potassium hydride.
  • the base can be used in a proportion of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (II).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually 0 ° C. to 200 ° C., preferably 10 to 120 ° C.
  • the reaction time is usually 1 to 48 hours.
  • R 1 is NR A R B among the compounds of the present invention, it can also be produced by the production method [2] represented by the following reaction formula.
  • R 2 , R 3 , R 4 , R 5 , R 6 , A, W, Z, R A , R B and X 1 are as described above.
  • Production method [2] can usually be carried out by reacting the compound of formula (I-2) with the compound of formula (IV) in the presence of a base and a solvent.
  • the compound of the formula (I-2) can be produced according to the method of the above production method [1].
  • the compound of the formula (IV) can be produced according to a known method, or a commercially available product may be used.
  • the compound of the formula (IV) can be used at a ratio of 1 to 50 equivalents, preferably 1 to 5 equivalents with respect to 1 equivalent of the compound of the formula (I-2).
  • the base used in this reaction is not particularly limited as long as the reaction proceeds.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate; sodium methoxide, sodium ethoxide, potassium tertiary butoxide
  • alkali metal alkoxides alkali metal hydrogen carbonates such as sodium hydrogen carbonate
  • alkaline earth metal carbonates such as calcium carbonate
  • metal hydroxides such as sodium hydroxide and potassium hydroxide
  • sodium hydride Metal hydrides such as potassium hydride
  • organic amines such as triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, and the like.
  • the base can be used in an amount of 1 to 20 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (IV).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually 0 ° C. to 200 ° C., desirably 50 ° C. to 150 ° C.
  • the reaction time is usually 1 to 48 hours.
  • the reaction of the production method [2] can be performed by adding an additive or a base as necessary in the presence of a condensing agent and a solvent.
  • a condensing agent examples include carbonyldiimidazole (CDI), N, N′-dicyclohexylcarbodiimide (DCC), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDC), chlorocarbonates, etc.
  • CDI carbonyldiimidazole
  • DCC N, N′-dicyclohexylcarbodiimide
  • EDC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride
  • chlorocarbonates etc.
  • the condensing agent can be used in an amount of 1 to 10 equivalents, preferably 1 to 3 equivalents, relative to 1 equivalent of the compound of formula (I-2).
  • Examples of the additive include 1-hydroxybenzotriazole monohydrate (HOBt).
  • the additive can be used in a proportion of 0.1 to 10 equivalents, preferably 0.5 to 3 equivalents, relative to 1 equivalent of the compound of formula (I-2).
  • Examples of the base include organic amines such as triethylamine, diisopropylethylamine, pyridine, and 4- (N, N-dimethylamino) pyridine.
  • the base can be used in an amount of 1 to 20 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (IV).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually 0 ° C. to 200 ° C., desirably 50 ° C. to 150 ° C.
  • the reaction time is usually 1 to 48 hours.
  • R 1 is N ⁇ CHNR C R D
  • it can also be produced by the following production methods [3] to [5].
  • Manufacturing method [3] Production method [3] is represented by the following reaction formula.
  • R 2 , R 3 , R 4 , R 5 , R 6 , A, W, Z, RC and RD are as described above.
  • L 1 , L 2 and L 3 are each independently alkyl or cycloalkyl.
  • the compound of the formula (I-4) is usually reacted with the compound of the formula (V) in the presence of an acid or a base and a solvent (step 3-1), and the resulting reaction mixture is subjected to reaction.
  • the reaction can be carried out by reacting the compound of formula (VI) (step 3-2).
  • the compound of the formula (I-4) can be produced according to the method of the above production method [1].
  • the compounds of formula (V) and formula (VI) can be produced according to known methods, respectively, or commercially available products may be used.
  • the compounds of formula (V) and formula (VI) can be used in a ratio of 0.8 to 80 equivalents, preferably 5 to 50 equivalents, per 1 equivalent of the compound of formula (I-4).
  • the acid used for reacting the compound of formula (I-4) with the compound of formula (V) is not particularly limited as long as the reaction proceeds.
  • p-toluenesulfonic acid examples include benzenesulfonic acid, methanesulfonic acid, hydrochloric acid and the like.
  • the base is not particularly limited as long as the reaction proceeds.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate
  • alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide.
  • Alkaline metal carbonates such as calcium carbonate; alkaline earth metal carbonates such as calcium carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; sodium hydride and potassium hydride
  • Metal hydrides such as: triethylamine, diisopropylethylamine, pyridine, and organic amines such as 4- (N, N-dimethylamino) pyridine.
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually 0 ° C. to 200 ° C., desirably 50 ° C. to 150 ° C.
  • the reaction time is usually 1 to 48 hours.
  • Step 3-2 in which the reaction mixture obtained in the reaction of Step 3-1 is reacted with the compound of formula (VI) is performed in the presence of a solvent.
  • a solvent those similar to those in Step 3-1 can be used.
  • the reaction temperature at this time is usually 0 ° C. to 200 ° C., preferably 10 to 150 ° C.
  • Manufacturing method [4] The production method [4] is represented by the following reaction formula.
  • R 2 , R 3 , R 4 , R 5 , R 6 , A, W, Z, RC and RD are as described above.
  • the production method [4] can usually be carried out by reacting the compound of formula (I-4) with the compound of formula (VII) in the presence of a halogenating agent and a solvent.
  • the compound of the formula (I-4) can be produced according to the method of the above production method [1].
  • the compound of the formula (VII) can be produced according to a known method, or a commercially available product may be used.
  • the compound of the formula (VII) can be used in a ratio of 0.8 to 80 equivalents, desirably 1 to 10 equivalents with respect to 1 equivalent of the compound of the formula (I-4).
  • halogenating agent examples include phosphorus pentachloride, phosphorus trichloride, phosphorus oxychloride, thionyl chloride and the like.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • those mentioned in the production method [3] can be used.
  • the reaction temperature is usually 0 ° C. to 200 ° C., preferably 20 to 150 ° C.
  • the reaction time is usually 1 to 48 hours.
  • Manufacturing method [5] The production method [5] is represented by the following reaction formula.
  • R 2 , R 3 , R 4 , R 5 , R 6 , A, W, Z, R C , R D , L 1 and L 2 are as described above.
  • the production method [5] can usually be carried out by reacting the compound of the formula (I-4) with the compound of the formula (VIII) in the presence of an acid or a base and a solvent.
  • the compound of the formula (I-4) can be produced according to the method of the above production method [1].
  • the compound of the formula (VIII) can be produced according to a known method, or a commercially available product may be used.
  • the compound of the formula (VIII) can be used in a ratio of 0.8 to 50 equivalents, desirably 1 to 10 equivalents with respect to 1 equivalent of the compound of the formula (I-4).
  • the solvent is not particularly limited as long as the reaction proceeds.
  • those mentioned in the production method [3] can be used.
  • the reaction temperature is usually 0 ° C. to 200 ° C., preferably 20 to 150 ° C.
  • the reaction time is usually 1 to 48 hours.
  • R 2 , R 3 , R 4 , R A , R B and X 1 are as described above.
  • the intermediate production method [1] can be carried out by reacting the compound of formula (II-2) and the compound of formula (IV) by a method according to the production method [2].
  • the compound of the formula (II-2) can be produced according to a known method, or a commercially available product may be used.
  • R 2 , R 3 , R 4 , R C and R D are as described above.
  • the intermediate production method [2] can be carried out by reacting the compound of the formula (II-4) by a method according to the production method [3], [4] or [5].
  • the compound of the formula (II-4) can be produced according to a known method, or a commercially available product may be used.
  • a and Z are as described above, X 2 is hydrogen, hydroxy or alkoxy, W 1 is O, S, NQ 1 , CHQ 1 O, CHQ 1 S, in order from the side bonded to A, CHQ 1 NQ 1 , OCHQ 1 , SCHQ 1 , NQ 1 CHQ 1 , CHQ 1 OCHQ 1 , CHQ 1 SCHQ 1 , CHQ 1 NQ 1 CHQ 1 or CHQ 1 .
  • the intermediate production method [3] can be usually carried out by reacting the compound of the formula (IX) with a reducing agent in the presence of a solvent.
  • the compound of the formula (IX) can be produced according to a known method or by the method described later, or a commercially available product may be used.
  • the reducing agent can be used in a ratio of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (IX).
  • the reducing agent used in this reaction is not particularly limited as long as the reaction proceeds, and examples include lithium aluminum hydride, lithium borohydride, sodium borohydride and the like.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • aromatic hydrocarbons such as benzene and toluene
  • aliphatic hydrocarbons such as hexane and heptane
  • ethers such as diethyl ether, tetrahydrofuran and dioxane
  • methanol One or two or more kinds can be selected as appropriate from alcohols such as ethanol and mixed solvents thereof.
  • the reaction temperature is usually ⁇ 100 ° C. to 200 ° C., desirably ⁇ 78 ° C. to 100 ° C.
  • the reaction time is usually 5 minutes to 24 hours.
  • R 5a is alkyl
  • R 6a is hydrogen or alkyl
  • Step 4-1 can usually be performed by reacting the compound of formula (III-3) with an oxidizing agent in the presence of a solvent.
  • the compound of the formula (III-3) can be produced according to a known method or by the aforementioned method, or a commercially available product may be used.
  • the oxidizing agent can be used in a proportion of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (III-3).
  • the oxidizing agent used in this reaction is not particularly limited as long as the reaction proceeds, and examples thereof include potassium permanganate, pyridinium chlorochromate (PCC), pyridinium dichromate (PDC), and Dess-Martin reagent.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • aromatic hydrocarbons such as benzene and toluene
  • aliphatic hydrocarbons such as hexane and heptane
  • halogenated carbonization such as chloroform, dichloroethane, and carbon tetrachloride.
  • 1 type or 2 types or more can be suitably selected from hydrogen, water, and these mixed solvents.
  • the reaction temperature is usually 0 ° C. to 200 ° C., desirably 10 ° C. to 100 ° C.
  • the reaction time is usually 5 minutes to 48 hours.
  • Step 4-2 can usually be performed by reacting the compound of the formula (X) with an organometallic reagent in the presence of a solvent.
  • the organometallic reagent can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (X).
  • the organometallic reagent used in this reaction is not particularly limited as long as the reaction proceeds, and examples thereof include alkyl lithium, alkyl magnesium halide, and dialkyl zinc. These organometallic reagents can be prepared according to known methods, or commercially available products may be used.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • aromatic hydrocarbons such as benzene and toluene
  • aliphatic hydrocarbons such as hexane and heptane
  • ethers such as diethyl ether, tetrahydrofuran and dioxane, and these 1 type, or 2 or more types can be suitably selected from these mixed solvents.
  • the reaction temperature is usually ⁇ 100 ° C. to 200 ° C., desirably ⁇ 78 ° C. to 100 ° C.
  • the reaction time is usually 5 minutes to 48 hours.
  • A, W 1 and Z are as described above, and X 3 is hydrogen or hydroxy.
  • the intermediate production method [5] can be usually carried out by reacting the compound of the formula (IX-2) with an acid or a base in the presence of a solvent.
  • the compound of the formula (IX-2) can be produced according to a known method or by the method described later, or a commercially available product may be used.
  • the acid or base can be used in a ratio of 1 to 20 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the compound of formula (IX-2).
  • the acid used in this reaction is not particularly limited as long as the reaction proceeds.
  • hydrochloric acid, sulfuric acid, trifluoroacetic acid, p-toluenesulfonic acid and the like can be used.
  • the base used in this reaction is not particularly limited as long as the reaction proceeds.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate; sodium methoxide, sodium ethoxide, potassium tertiary butoxide
  • alkali metal alkoxides alkali metal hydrogen carbonates such as sodium hydrogen carbonate
  • alkaline earth metal carbonates such as calcium carbonate
  • metal hydroxides such as sodium hydroxide and potassium hydroxide
  • sodium hydride Metal hydrides such as potassium hydride
  • organic amines such as triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, and the like.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • aromatic hydrocarbons such as benzene and toluene
  • aliphatic hydrocarbons such as hexane and heptane
  • ethers such as diethyl ether, tetrahydrofuran and dioxane
  • methanol Alcohols such as ethanol
  • halogenated hydrocarbons such as chloroform, dichloroethane, and carbon tetrachloride
  • one or two or more kinds can be appropriately selected from water and a mixed solvent thereof.
  • the reaction temperature is usually 0 ° C. to 200 ° C., desirably 0 ° C. to 100 ° C.
  • the reaction time is usually 1 hour to 48 hours.
  • Intermediate production method [5] can also be carried out by reacting the compound of formula (IX-2) with a reducing agent in the presence of a solvent and decomposing the resulting reaction mixture with an acid.
  • the reducing agent used in this reaction can be used in a ratio of 1 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 equivalent of the compound of formula (IX-2).
  • Examples of the reducing agent used in this reaction include diisobutylaluminum hydride (DIBAL-H), sodium bis (2-methoxyethoxy) aluminum hydride (Red-Al), and the like.
  • DIBAL-H diisobutylaluminum hydride
  • Red-Al sodium bis (2-methoxyethoxy) aluminum hydride
  • the acid used in this reaction is not particularly limited as long as the reaction proceeds, and examples thereof include hydrochloric acid, sulfuric acid, trifluoroacetic acid, p-toluenesulfonic acid and the like.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • aromatic hydrocarbons such as benzene and toluene
  • aliphatic hydrocarbons such as hexane and heptane
  • ethers such as diethyl ether, tetrahydrofuran and dioxane
  • chloroform One or two or more kinds can be appropriately selected from halogenated hydrocarbons such as dichloroethane and carbon tetrachloride, and mixed solvents thereof.
  • the reaction temperature is usually ⁇ 100 ° C. to 200 ° C., desirably ⁇ 78 ° C. to 100 ° C.
  • the reaction time is usually 10 minutes to 24 hours.
  • A, Q 1 and Z are as described above, T is alkoxycarbonyl or cyano, and W 5 is O, S, NQ 1 , CHQ 1 O, CHQ 1 S in this order from the side bonded to A.
  • G 1 and G 2 are halogen, OH, NHQ 1 or SH, and when G 1 is halogen, G 2 is OH, NHQ 1 or SH, and G 1 is OH, NHQ 1 or SH Sometimes G 2 is halogen.
  • p and q are integers of 0 to 2, and p + q ⁇ 2.
  • the intermediate production method [6] can be carried out by reacting the compound of the formula (XI) and the compound of the formula (XII) with the addition of a phase transfer catalyst as necessary in the presence of a base and a solvent.
  • the compounds of formula (XI) and formula (XII) can be produced according to known methods, or commercially available products may be used.
  • the compound of the formula (XII) can be used at a ratio of 1 to 20 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of the formula (XI).
  • the base used in this reaction is not particularly limited as long as the reaction proceeds.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate; sodium methoxide, sodium ethoxide, potassium tertiary butoxide
  • alkali metal alkoxides alkali metal hydrogen carbonates such as sodium hydrogen carbonate
  • alkaline earth metal carbonates such as calcium carbonate
  • metal hydroxides such as sodium hydroxide and potassium hydroxide
  • sodium hydride Metal hydrides such as potassium hydride
  • organic amines such as triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, and the like.
  • the base can be used in an amount of 1 to 20 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (XII).
  • phase transfer catalyst examples include quaternary ammonium salts such as tetrabutylammonium bromide, tetrabutylammonium iodide, and benzyltriethylammonium bromide; 18-crown 6-ether.
  • the phase transfer catalyst can be used at a ratio of 0.01 to 0.5 equivalent, preferably 0.05 to 0.2 equivalent, relative to 1 equivalent of the compound of formula (XI).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually 0 ° C. to 200 ° C., desirably 50 ° C. to 150 ° C.
  • the reaction time is usually 1 to 48 hours.
  • the intermediate production method [7] can be carried out by reacting the compound of the formula (XIII) in the presence of an acid or a fluorine compound and a solvent.
  • the compound of the formula (XIII) can be produced according to a known method or by the method described later, or a commercially available product may be used.
  • the acid used in this reaction is not particularly limited as long as the reaction proceeds, and examples thereof include hydrochloric acid, acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, benzenesulfonic acid, methanesulfonic acid and the like.
  • the acid can be used in a ratio of 1 to 20 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (XIII).
  • the fluorine compound used in this reaction is not particularly limited as long as the reaction proceeds, and examples thereof include tetrabutylammonium fluoride (TBAF), cesium fluoride, and HF-pyridine.
  • TBAF tetrabutylammonium fluoride
  • cesium fluoride cesium fluoride
  • HF-pyridine HF-pyridine.
  • the fluorine compound can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (XIII).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually 0 ° C to 200 ° C, preferably 0 to 50 ° C.
  • the reaction time is usually 1 to 24 hours.
  • G 3 and G 4 are C ( ⁇ O) X 1 , S ( ⁇ O) X 1 , S ( ⁇ O) 2 X 1 , OH, NHQ 1 or SH, and G 3 is C ( ⁇ O).
  • G 4 is OH, NHQ 1 or SH
  • G 3 is OH, NHQ 1 or SH
  • G 4 Is C ( ⁇ O) X 1 , S ( ⁇ O) X 1 or S ( ⁇ O) 2 X 1 , where X 1 is as described above.
  • the intermediate production method [8] can be carried out by reacting the compound of formula (XIV) with the compound of formula (XV) by a method according to the production method [2].
  • the compound of the formula (XIV) can be produced according to a known method or by the method described later, or a commercially available product may be used.
  • the compound of the formula (XV) can be produced according to a known method, or a commercially available product may be used.
  • R 5 , R 6 , A, L 4 , L 5 , L 6 , Q 1 and G 3 are as described above, and X 4 is halogen.
  • the intermediate production method [9] can be carried out by reacting the compound of formula (XVI) with the compound of formula (XVII) in the presence of a base and a solvent.
  • Compounds of formula (XVI) and (XVII) can be produced according to known methods, or commercially available products may be used.
  • the compound of the formula (XVII) can be used at a ratio of 1 to 20 equivalents, desirably 1 to 5 equivalents with respect to 1 equivalent of the compound of the formula (XVI).
  • the base used in this reaction is not particularly limited as long as the reaction proceeds.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate; sodium methoxide, sodium ethoxide, potassium tertiary butoxide
  • alkali metal alkoxides alkali metal hydrogen carbonates such as sodium hydrogen carbonate
  • alkaline earth metal carbonates such as calcium carbonate
  • metal hydroxides such as sodium hydroxide and potassium hydroxide
  • sodium hydride And metal hydrides such as potassium hydride
  • organic amines such as triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, and imidazole.
  • the base can be used in an amount of 1 to 20 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the compound of formula (XVI).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually ⁇ 100 ° C. to 200 ° C., desirably 0 to 100 ° C.
  • the reaction time is usually 1 to 48 hours.
  • Step 10-1 can usually be performed by reacting the compound of formula (XVIII) with triphosgene in the presence of a base and a solvent.
  • the compound of the formula (XVIII) can be produced according to a known method, or a commercially available product may be used.
  • Triphosgene can be used in a proportion of 0.1 to 5 equivalents, preferably 0.2 to 0.5 equivalents, relative to 1 equivalent of the compound of formula (XVIII).
  • the base used in this reaction is not particularly limited as long as the reaction proceeds.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate; sodium methoxide, sodium ethoxide, potassium tertiary butoxide
  • alkali metal alkoxides alkali metal hydrogen carbonates such as sodium hydrogen carbonate
  • alkaline earth metal carbonates such as calcium carbonate
  • metal hydroxides such as sodium hydroxide and potassium hydroxide
  • sodium hydride And metal hydrides such as potassium hydride
  • organic amines such as triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, and imidazole.
  • the base can be used in a ratio of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (XVIII).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually ⁇ 100 ° C. to 200 ° C., desirably 0 to 100 ° C.
  • the reaction time is usually 1 to 48 hours.
  • Step 10-2 can usually be performed by reacting the compound of formula (XIX) with the compound of formula (XX) in the presence of a base and a solvent.
  • the compound of the formula (XX) can be produced according to a known method or by the method described later, or a commercially available product may be used.
  • the compound of the formula (XX) can be used at a ratio of 1 to 5 equivalents, desirably 1 to 10 equivalents, relative to 1 equivalent of the compound of the formula (XIX).
  • the base used in this reaction is not particularly limited as long as the reaction proceeds.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate; sodium methoxide, sodium ethoxide, potassium tertiary butoxide
  • alkali metal alkoxides alkali metal hydrogen carbonates such as sodium hydrogen carbonate
  • alkaline earth metal carbonates such as calcium carbonate
  • metal hydroxides such as sodium hydroxide and potassium hydroxide
  • sodium hydride And metal hydrides such as potassium hydride
  • organic amines such as triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, and imidazole.
  • the base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (XIX).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually 0 ° C. to 200 ° C., preferably 0 to 100 ° C.
  • the reaction time is usually 1 to 48 hours.
  • the compound of formula (XIII-2) is obtained by reacting the compound of formula (XVIII) with triphosgene in the presence of a base and a solvent according to Step 10-1, and then reacting the resulting product with formula (XX). Can also be produced by reacting the compound according to step 10-2 in the presence of a base and a solvent.
  • R 5 , R 6 , A, L 4 , L 5 , L 6 , G 6 and X 4 are as described above.
  • the intermediate production method [11] can be carried out by reacting the compound of formula (XXI) with the compound of formula (XVII) by a method according to the intermediate production method [9].
  • Compounds of formula (XXI) and (XVII) can be produced according to known methods, or commercially available products may be used.
  • A, R 5 , R 6 , X 4 and Z are as described above, and M is a metal atom such as magnesium or zinc or a salt thereof, or a residue of boronic acid or an ester thereof.
  • the intermediate production method [12] can be usually performed by reacting a compound of the formula (XXII) with an organometallic reagent of the formula (XXIII) in the presence of a transition metal catalyst and a solvent.
  • the compound of the formula (XXII) and the organometallic reagent of the formula (XXIII) can be produced according to known methods, or commercially available products may be used.
  • the organometallic reagent can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (XXII).
  • the organometallic reagent used in this reaction is not particularly limited as long as the reaction proceeds, and examples thereof include a Grignard reagent, an organozinc reagent, and an organoboron compound. These organometallic reagents can be prepared according to known methods, or commercially available products may be used.
  • transition metal catalysts include catalysts containing transition metals such as palladium, rhodium, ruthenium, nickel, cobalt, and molybdenum.
  • transition metal catalyst those having various known structures used for cross-coupling reactions of organic halides can be used, and a transition metal catalyst containing palladium is particularly useful for this reaction.
  • a tertiary phosphine and a tertiary phosphite can be used as a ligand as needed.
  • Tertiary phosphines and tertiary phosphites include triphenylphosphine, phenyldimethylphosphine, tri-o-tolylphosphine, tri-p-tolylphosphine, 1,2-bis (diphenylphosphino) ethane, 1, Examples thereof include 3-bis (diphenylphosphino) propane, 1,4-bis (diphenylphosphino) butane, 1,1′-bis (diphenylphosphino) ferrocene, and triphenyl phosphite.
  • the transition metal catalyst is usually used in an amount of 0.001 to 0.5 equivalent, preferably 0.05 to 0.2 equivalent, relative to 1 equivalent of the compound of the formula (XXII).
  • the ligand can be used in an amount of usually 1 to 50 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the transition metal catalyst. However, depending on the reaction conditions, an amount outside this range can be used.
  • This reaction can be performed by adding a base, if necessary.
  • the base include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; and alkali metal carbonates such as sodium hydrogen carbonate.
  • the base can be used at a ratio of 1 to 20 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the compound of formula (XXII).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually ⁇ 100 ° C. to 200 ° C., desirably ⁇ 78 ° C. to 100 ° C.
  • the reaction time is usually 5 minutes to 48 hours.
  • A, R 5 , R 6 and Z are as described above, and r is an integer of 1 or 2.
  • the intermediate production method [13] can usually be carried out by reacting the compound of the formula (III-7) with an oxidizing agent in the presence of a solvent.
  • the compound of the formula (III-7) can be produced according to a known method or by the aforementioned method, or a commercially available product may be used.
  • the oxidizing agent can be used in a proportion of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (III-7).
  • oxidizing agent used in this reaction examples include hydrogen peroxide, peracetic acid, m-chloroperbenzoic acid and the like. These oxidizing agents can be prepared according to known methods, or commercially available products may be used.
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually 10 ° C. to 200 ° C., desirably 20 ° C. to 100 ° C.
  • the reaction time is usually 1 to 24 hours.
  • G 7 and G 8 are CHQ 1 X 4 or M.
  • G 7 is CHQ 1 X 4
  • G 8 is M
  • G 7 is M
  • G 8 is CHQ 1 X 4 .
  • Yes, X 4 and M are as described above.
  • the intermediate production method [14] can be usually carried out by reacting the compound of the formula (XXIV) with the compound of the formula (XXV) in the presence of a transition metal catalyst, a base and a solvent.
  • the compound of the formula (XXIV) and the compound of the formula (XXV) can be produced according to known methods, or commercially available products may be used.
  • the compound of the formula (XXV) can be used in a ratio of 1 to 10 equivalents, preferably 1 to 3 equivalents, relative to 1 equivalent of the compound of the formula (XXIV).
  • transition metal catalysts include catalysts containing transition metals such as palladium, rhodium, ruthenium, nickel, cobalt, and molybdenum.
  • transition metal catalyst those having various known structures used for cross-coupling reactions of organic halides can be used, and a transition metal catalyst containing palladium is particularly useful for this reaction.
  • a tertiary phosphine and a tertiary phosphite can be used as a ligand as needed.
  • Tertiary phosphines and tertiary phosphites include triphenylphosphine, phenyldimethylphosphine, tri-o-tolylphosphine, tri-p-tolylphosphine, 1,2-bis (diphenylphosphino) ethane, 1, Examples thereof include 3-bis (diphenylphosphino) propane, 1,4-bis (diphenylphosphino) butane, 1,1′-bis (diphenylphosphino) ferrocene, and triphenyl phosphite.
  • the transition metal catalyst is usually used in an amount of 0.001 to 0.5 equivalent, preferably 0.05 to 0.2 equivalent, relative to 1 equivalent of the compound of the formula (XXIV).
  • the ligand can be used in an amount of usually 1 to 50 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the transition metal catalyst. However, depending on the reaction conditions, an amount outside this range can be used.
  • the base examples include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; and alkali metal carbonates such as sodium hydrogen carbonate.
  • the base can be used in an amount of 1 to 20 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the compound of formula (XXIV).
  • the solvent is not particularly limited as long as the reaction proceeds, and for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; methyl acetate, ethyl acetate Esters such as; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, propionitrile, acrylonite Ni
  • the reaction temperature is usually ⁇ 100 ° C. to 200 ° C., desirably ⁇ 78 ° C. to 100 ° C.
  • the reaction time is usually 5 minutes to 48 hours.
  • the fungicide for agricultural and horticultural use and the method for controlling plant diseases for example, Mastigomytina, Ascomycotina, Basidiomycotina, incomplete fungus It is possible to control phytopathogenic fungi belonging to Amonia (Deuteromycotina), Zygomycotina, and the like.
  • plant pathogenic bacteria More specific examples include the following.
  • Phytophthora capsici such as tomato gray plague (Pseudoperonospora penicillium) Pola (Pseudoperonospora); Plasmopara genus such as Plasmopara viticola; Rice seedling blight (Pythium graminicola), Wheat brown snow rot (Pythium pylori) And so on.
  • Erysiphe genus such as wheat powdery mildew (Erysiphe graminis); A genus Uncinula such as Grape powdery mildew (Uncinula necator); a genus Podosphaera pelosphaera (Podosphaeraella); Mycosphaerella fungus ), Banana Black Shigato Mycosphaerella inu genus V. var. Genus Mycosphaerella inu, genus Mycosphaerella in genus Mycosphaerella inu, and genus Mycosphaerella inu.
  • Venturia genus Pyrenophora genus such as Pyrenophora teres, Pyrenophora glaminea; Sclerotinosculus sclerotia genus Erotinia; Cochliobolus genus such as Cochliobolus miyabeanus; Gibberella genus such as: Elsinoe ampelina, Elsinoe genus Elsinoe such as citrus scab (Dipsorthepitus citrus), Diaporthe genus such as; apple Monilia fungus (Monilin) ia mali, Monilinia genus such as Monilinia fructicola; Glomerella genus such as Gramerella cinulata; Rice blast fungus (Magnagoleporella) Magnaporthe) genus; and the like.
  • Pyrenophora genus such as Pyrenophora teres, Pyrenophora glaminea
  • Rhizoctonia genus such as rice rot (Rhizoctonia solani); Ustylago genus (Ustilago genus) such as wheat brown rot; Examples include wheat red rust fungus (Puccinia recondita) and genus Puccinia such as wheat yellow rust fungus (Puccinia striformis).
  • Septoria nodorum Septoria tritici such as Septoria tritici
  • Botrytis genus such as Botrytis cinerea
  • Botrytis genus Botrytis Botrytis cinerea
  • Cercospora beticola Cercospora beticola
  • Cercospora genus such as Cercospora kakivola
  • Colletoliterum genus Coltotartrum leaflet apple (pathotype), pear black spot fungus ( Alternaria spruce (Alternaria sp.), such as litteraria alternata, Japan pear pathotype, potato summer rot or Alternaria sosali, cabbage black spot fungus (Alternaria sp.).
  • Cosporella Pseudocercosporella
  • Pseudocercospora vits such as Pseudocercospora vits
  • Rychosporium sericis Rychosporium salis genus chosporium
  • genus Cladosporium such as Cladosporia carpophilum
  • Examples include the genus Gloeosporium; the genus Fulvia such as Tomato leaf fungus (Fulvia fulva); and the genus Corynespora such as Corynespora cassiicola.
  • Examples of the zygomycota include the genus Rhizopus such as strawberry soft rot fungus and Rhizopus nigricans.
  • the compound of the present invention is useful as an active ingredient of an agricultural and horticultural fungicide, and in the method according to the present invention, an agricultural and horticultural fungicide and a method for controlling plant diseases, for example, rice blast, sesame leaf blight, crest Blight; wheat powdery mildew, red mold, rust, snow rot, naked smut, eye spot, leaf blight, blight; citrus sunspot, scab; apple moniliosis , Powdery mildew, spotted leaf disease, black spot disease, anthracnose disease, brown spot disease, ring pattern disease, soot spot disease, soot spot disease, black spot disease; pear black star disease, black spot disease, powdery mildew disease, plague; Pear ring-shaped disease, powdery mildew; peach blight, black rot, homoposis rot; grape black rot, late rot, powdery mildew, mildew, gray mold, brown spot, Branch scab; oyster anthracnose
  • the compound of the present invention is usually prepared by mixing the compound with various agricultural adjuvants, powders, granules, granule wettable powders, wettable powders, aqueous suspensions, oily suspensions, aqueous solvents, emulsions, Formulated in various forms such as liquids, pastes, aerosols, microdispersions, etc., and used as agricultural and horticultural fungicides, etc., as long as they meet the purpose of the present invention, they are usually used in the field Any formulation can be used.
  • Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; water, Solvents such as toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol Fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylates, alkyl sulfate esters, alkyl sulfates, alkylaryl s
  • each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. Further, in addition to the above-mentioned adjuvants, it can also be used by appropriately selecting from those known in the art, a bulking agent, a thickener, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a safener, Various commonly used adjuvants such as antifungal agents can also be used.
  • the compounding ratio of the compound of the present invention and various adjuvants is generally 0.005: 99.995 to 95: 5, preferably 0.2: 99.8 to 90:10, by weight. Therefore, the content of the compound of the present invention in the agricultural and horticultural fungicide is 0.005% to 95% by weight, desirably 0.2% to 90% by weight.
  • these preparations use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.
  • the concentration of the compound of the present invention varies depending on the target crop, method of use, formulation, application rate, etc., and cannot be generally defined.
  • foliage treatment it is usually 0.1 to 10,000 ppm, preferably 1 ⁇ 2,000 ppm.
  • soil treatment it is usually 10 to 100,000 g / ha, preferably 200 to 20,000 g / ha.
  • seed treatment it is usually 0.01 to 100 g / Kg seed, preferably 0.02 to 20 g / Kg seed.
  • the compound of the present invention can be applied to plants, soils, and the like by a generally used application method for application of various preparations such as agricultural and horticultural fungicides or dilutions thereof.
  • spraying eg spraying, spraying, misting, atomizing, dusting, water surface application, etc.
  • soil application mixed, irrigation, etc.
  • surface application application, powder coating, coating, etc.
  • ultra-low concentration small volume application method ultra low volume application method. In this method, it is possible to contain 100% of the active ingredient.
  • the compound of the present invention may contain other agrochemicals as required, such as fungicides, insecticides, acaricides, nematicides, soil insecticides, antiviral agents, attractants, herbicides, plant growth regulators, etc. Can be mixed and used together. In this case, a more excellent effect may be exhibited.
  • bactericide for example, anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil; Tria such as 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine Zolopyrimidine compounds; Pyridinamine compounds such as fluazinam; Triadimefone, bittertanol, triflumizole, etaconazole, propiconazole, penconazole, luconilole, flusilazole, penconazole, flusilazole.
  • cyproconazole tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiazole ), Tetraconazole, oxpoconazole fumarate, prothioconazole, triadimenol, flutria folate, difinaconol, flutria folate (Fluquinconazole), fenbuconazole, bromuconazole, diniconazole, tricyclazole, probenazole (probenazole), probenazole (probenazole), probenazole (probenazole) furazoate), ipconazole (ipconazole), imibenconazole (imibenconazole), azole compounds such as azaconazole (azaconazole), triticonazole (triticonazole), imazalil (imazalil); Quinoxaline-based compounds such as quinometh
  • Amide compounds such as pydiflumethofen; Benzamide compounds such as fluopyram and zoxamide; Piperazine-based compounds such as triforine; Pyridine compounds such as pyrifenox, pyrisoxazole; Carbinol compounds such as fenarimol, nuarimol; Piperidine compounds such as fenpropidin; Morpholine-based compounds such as fenpropimorph, tridemorph; Organotin compounds such as fentin hydroxide and fentin acetate; Urea-based compounds such as pencycuron; Synamic acid-based compounds such as dimethomorph, flumorph; Phenyl carbamate compounds such as dietofencarb; Cyanopyrrole-based compounds such as fludioxonil, fenpiclonil; Azoxystrobin, cresoxime-methyl, methminostrobin, trifloxystrobin, picoxystrobin, oryzrobine, oryzodistrob
  • Insecticides acaricides, nematicides or soil pesticides in the above-mentioned other pesticides, that is, active ingredient compounds of pesticides (generic name; including some pending applications or Japan Plant Protection Association test code) ),
  • pesticides for example, Profenofos, dichlorvos, fenamifos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifosmethyl, chlorpyriphosmethyl Phosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, etionfos, etrimfos, quinalph s), dimethylvinphos (dimethyvinphos), dimethoate (sulfofos), thiomethon (thiometon), bamidthione (vamidothion), pyraclothiophosphine (pyridiophthropyphos) ), Fos
  • Bacillus thuringiensis produces, entomopathogenic viral agents, entomopathogenic fungus agent, nematode pathogenic fungi agents such as Microbial pesticides such as: avermectin, emamectin benzoate, milbemectin, milbemycin, Antibiotics and semi-synthetic antibiotics such as nosad, ivermectin, repimectin, DE-175, abamectin, emamectin, spinetoram; azadiractin Natural products such as, rotenone, ryanodine; repellents such as deet; It can also be used in combination
  • Methyl 4- (bromomethyl) benzoate (5 g), phenylboronic acid (3.19 g) and tetrakis (triphenylphosphine) palladium (2.52 g) were added to the flask, and the atmosphere was replaced with nitrogen.
  • An aqueous solution (16 mL) of ethylene glycol dimethyl ether (80 mL) and sodium carbonate (4.63 g) was added, and the mixture was stirred at 100 ° C. for 4 hours.
  • the reaction mixture was cooled to room temperature, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate.
  • Solution (I) To a solution of (4-benzylphenyl) methanol (142 mg) in dimethylformamide (1.5 mL) was added dropwise thionyl chloride (82 mg) at 0 ° C. and stirred for 30 minutes to prepare Solution (I). To a solution of 2,6-diaminonicotinic acid (100 mg) in dimethylformamide (2.5 mL) was added potassium carbonate (406 mg), and the mixture was stirred at 40 ° C. for 30 minutes, then solution (I) was added, and 90 ° C. was added for 1 hour. The mixture was stirred halfway, heated to 100 ° C. and further stirred for 5 hours.
  • the reaction mixture was cooled to 0 ° C., water was added, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate / heptane) to obtain the desired product (57 mg).
  • the obtained compound of the present invention was designated as No. 1 in Table 1. 1-No. 435.
  • Table 1 the numerical values shown as physical properties are melting points (° C.). These compounds can be synthesized based on the above synthesis examples or the above-described production method of the compound of the present invention.
  • Me is methyl
  • Et is ethyl
  • nPr is propyl
  • iPr is isopropyl
  • cPr is cyclopropyl
  • nBu butyl
  • tBu is tert-butyl
  • sBu sec-butyl
  • iBu is isobutyl
  • nHex hexyl.
  • Ph represents phenyl
  • Ac represents acetyl.
  • Table 2 shows 1 H-NMR data [measured by 1 H-nuclear magnetic resonance spectroscopy; ⁇ is a chemical shift value (ppm)] for some of the compounds of the present invention.
  • TMS means tetramethylsilane.
  • Test example 1 (wheat powdery mildew prevention effect test) Growing wheat (variety: Norin 61) in a plastic pot with a diameter of 6.0 cm and spraying 10 ml of a chemical solution with the compound of the present invention adjusted to a predetermined concentration when the 1.5 leaf stage is reached with a spray gun did. After the drug solution was dried, conidia of wheat powdery mildew (Erysiphe graminis) were sprinkled and inoculated, and kept in a constant temperature room at 20 ° C. Seven days after the inoculation, the number of lesions was investigated, and a control index was determined according to the above evaluation criteria. The compound No. 1 described in Table 1 was used. 27, 196, 197, 198, 212, 231, 232, 266, and 267 were tested, and all showed an effect of the compound concentration of 400 ppm and a control index of 4 or more.
  • Test Example 2 Tomato plague prevention effect test
  • Growing tomato (variety: yellow pair, the best in the world) in a 7.5cm diameter plastic pot, and when the 3-4 leaf stage is reached, use a spray gun to add a sufficient amount of the drug solution adjusted to the prescribed concentration Scattered.
  • a zoospore suspension of Phytophthora infestans was spray-inoculated and kept in a constant temperature room at 20 ° C.
  • the lesion area was examined, and the control index was determined according to the evaluation criteria.
  • the compound No. 1 described in Table 1 was used. When 34, 85, 109, 112, 132, 212, 231, 233, 263, 283, 294, 295 and 322 were tested, all showed an effect of the compound concentration of 400 ppm and a control index of 4 or more.
  • Test Example 3 Cucumber downy mildew prevention test
  • Cucumber (variety: Sagamihanjiro) was cultivated in a plastic pot with a diameter of 7.5 cm, and when the 1.5 leaf stage was reached, a sufficient amount of chemical solution adjusted to a predetermined concentration of the compound of the present invention was sprayed with a spray gun. .
  • the zoosporangium suspension of Pseudoperonospora cubensis was sprayed and inoculated in a 20 ° C. inoculation box for about 1 day and kept in a constant temperature room at 20 ° C.
  • the lesion area was examined 6 to 7 days after the inoculation, and the control index was determined according to the above evaluation criteria.
  • the compound No. 1 described in Table 1 was used. When 34, 48, 109, 112, 212, 230, 248, 263, 266, 294 and 295 were tested, the compound concentration was 400 ppm and the control index was 4 or more.
  • Test Example 4 Cucumber powdery mildew prevention effect test
  • Cucumber (variety: Sagamihanjiro) was cultivated in a plastic pot with a diameter of 7.5 cm, and when the 1.5 leaf stage was reached, a sufficient amount of chemical solution adjusted to a predetermined concentration of the compound of the present invention was sprayed with a spray gun. . After the chemical solution was dried, a spore suspension of Sphaerotheca furiginea was spray-inoculated and kept in a constant temperature room at 20 ° C. Seven days after the inoculation, the lesion area was examined, and the control index was determined according to the evaluation criteria. The compound No. 1 described in Table 1 was used. When 109, 132, 196, 197, 212, 248, 263, 307 and 322 were tested, the compound concentration was 400 ppm and the control index was 4 or more.
  • Test Example 5 Green Bean Fungus Prevention Effect Test
  • Green beans variety: Taishokin
  • a sufficient amount of a chemical solution adjusted to a predetermined concentration of the compound of the present invention was sprayed with a spray gun.
  • a conidial spore suspension of Botrytis cinerea was soaked in a paper disk having a diameter of 8 mm, inoculated on a floor, and kept in a constant temperature room at 20 ° C.
  • the lesion area was examined, and the control index was determined according to the evaluation criteria.
  • the compound No. 1 described in Table 1 was used.
  • Test Example 6 (Test for preventing kidney bean nuclear disease) Green beans (variety: Taishokin) were cultivated in a plastic pot with a diameter of 12 cm, and when the 2 to 3 leaf stage was reached, a sufficient amount of a chemical solution adjusted to a predetermined concentration of the compound of the present invention was sprayed with a spray gun. After the drug solution was dried, the flora disc of sclerotia sclerotium cultured in PSA medium was punched and inoculated with a cork borer having a diameter of 4 mm and kept in a constant temperature room at 20 ° C. Three days after the inoculation, the lesion area was examined, and the control index was determined according to the evaluation criteria. The compound No. 1 described in Table 1 was used.
  • Formulation examples using the compound of the present invention are shown below.
  • Formulation Example 1 (1) Compound of the present invention 20 parts by weight (2) 72 parts by weight of clay (3) Sodium lignin sulfonate 8 parts by weight The above is uniformly mixed to obtain a wettable powder.
  • Formulation Example 2 (1) Compound of the present invention 5 parts by weight (2) 95 parts by weight of talc The above components are uniformly mixed to form a powder.
  • Formulation Example 3 (1) 20 parts by weight of the compound of the present invention (2) 20 parts by weight of N, N-dimethylacetamide (3) 10 parts by weight of polyoxyethylene alkylphenyl ether (4) 50 parts by weight of xylene To make an emulsion.
  • Formulation Example 4 (1) Clay 68 parts by weight (2) Lignin sulfonic acid soda 2 parts by weight (3) Polyoxyethylene alkylaryl ether sulfate 5 parts by weight (4) Fine silica 25 parts by weight Are mixed at a weight ratio of 4: 1 to obtain a wettable powder.
  • Formulation Example 5 (1) Compound of the present invention 50 parts by weight (2) Oxidated polyalkylphenyl phosphate triethanolamine 2 parts by weight (3) Silicone 0.2 parts by weight (4) Water 47.8 parts by weight (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are further added to the mixed and crushed stock solution, and the mixture is uniformly mixed, granulated and dried to obtain a granulated wettable powder.
  • Formulation Example 6 (1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene phosphate ester 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1) to (3) is uniformly mixed in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove the acetone and form granules.
  • Formulation Example 7 (1) 2.5 parts by weight of the compound of the present invention (2) 2.5 parts by weight of N-methyl-2-pyrrolidone (3) 95.0 parts by weight of soybean oil (Ultra low volume formulation).
  • Formulation Example 8 (1) Compound of the present invention 20 parts by weight (2) Oxidated polyalkylphenyl phosphate triethanolamine 2 parts by weight (3) Silicone 0.2 parts by weight (4) Xanthan gum 0.1 part by weight (5) Ethylene glycol 5 Part by weight (6) Water 72.7 parts by weight The above is uniformly mixed and pulverized to obtain an aqueous suspension.
  • the compound of the present invention has a high control effect against a wide range of plant pathogens and is useful as an agricultural and horticultural fungicide.

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Abstract

　L'objectif de la présente invention est de fournir : un composé, ou un sel de celui-ci, qui est efficace dans un fongicide agricole et horticole manifestant un effet de lutte exceptionnel contre diverses maladies de plantes ; un fongicide agricole et horticole ; et un procédé de lutte contre des maladies de plantes. La présente invention concerne un composé représenté par la formule (I), ou un sel de celui-ci, ainsi qu'un fongicide agricole et horticole contenant ce composé ou un sel de celui-ci comme principe actif et un procédé de lutte contre des maladies de plantes.
PCT/JP2015/075902 2014-09-12 2015-09-11 Composé d'ester d'acide nicotinique, fongicide agricole et horticole et procédé de lutte contre les maladies de plantes WO2016039459A1 (fr)

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CN108473431A (zh) * 2016-01-21 2018-08-31 阿格罗－金正株式会社 2-氨基烟酸苄酯衍生物的制造方法
CN115197131A (zh) * 2021-04-13 2022-10-18 华东理工大学 偶氮类2-氨基烟酸苄酯衍生物及其制备方法和用途

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JPH09506591A (ja) * 1993-09-14 1997-06-30 ヘキスト・シェーリング・アグレボ・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 置換ピリジン、その製造方法及び農薬及び殺菌剤としてのその使用方法
WO2014006945A1 (fr) * 2012-07-04 2014-01-09 アグロカネショウ株式会社 Dérivé d'ester d'acide 2-aminonicotinique et bactéricide le contenant comme principe actif
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WO2015060378A1 (fr) * 2013-10-25 2015-04-30 日本曹達株式会社 Dérivé d'aminopyridine et fongicide agricole et horticole
JP2015089883A (ja) * 2013-11-06 2015-05-11 アグロカネショウ株式会社 ２−アミノニコチン酸ベンジルエステル誘導体およびこれを有効成分とする殺菌剤

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JPH05255255A (ja) * 1992-03-12 1993-10-05 Kumiai Chem Ind Co Ltd ６−ｎ−置換アミノピコリン酸誘導体及びその製造法
JPH09506591A (ja) * 1993-09-14 1997-06-30 ヘキスト・シェーリング・アグレボ・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 置換ピリジン、その製造方法及び農薬及び殺菌剤としてのその使用方法
WO2014006945A1 (fr) * 2012-07-04 2014-01-09 アグロカネショウ株式会社 Dérivé d'ester d'acide 2-aminonicotinique et bactéricide le contenant comme principe actif
JP2015030693A (ja) * 2013-08-01 2015-02-16 アグロカネショウ株式会社 ２−アミノニコチン酸ベンジル誘導体およびこれを有効成分とする殺菌剤
WO2015060378A1 (fr) * 2013-10-25 2015-04-30 日本曹達株式会社 Dérivé d'aminopyridine et fongicide agricole et horticole
JP2015089883A (ja) * 2013-11-06 2015-05-11 アグロカネショウ株式会社 ２−アミノニコチン酸ベンジルエステル誘導体およびこれを有効成分とする殺菌剤

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Publication number Priority date Publication date Assignee Title
CN108473431A (zh) * 2016-01-21 2018-08-31 阿格罗－金正株式会社 2-氨基烟酸苄酯衍生物的制造方法
CN108473431B (zh) * 2016-01-21 2021-08-10 阿格罗－金正株式会社 2-氨基烟酸苄酯衍生物的制造方法
CN115197131A (zh) * 2021-04-13 2022-10-18 华东理工大学 偶氮类2-氨基烟酸苄酯衍生物及其制备方法和用途

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