WO2015068773A1 - Composé hétérocyclique saturé contenant de l'azote - Google Patents

Composé hétérocyclique saturé contenant de l'azote Download PDF

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WO2015068773A1
WO2015068773A1 PCT/JP2014/079488 JP2014079488W WO2015068773A1 WO 2015068773 A1 WO2015068773 A1 WO 2015068773A1 JP 2014079488 W JP2014079488 W JP 2014079488W WO 2015068773 A1 WO2015068773 A1 WO 2015068773A1
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compound
alkyl
salt
hydrogen
substituted
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Japanese (ja)
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智裕 岡本
晋太朗 佃
ゆずか 河合
真徳 若林
将也 大野
勝也 石原
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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
    • 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
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • 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
    • A01N43/72—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
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D405/14—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 three or more hetero rings
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D475/00—Heterocyclic compounds containing pteridine ring systems
    • C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to a novel compound having a nitrogen-containing saturated heterocyclic ring or a salt thereof, an agricultural and horticultural fungicide containing the compound or the salt as an active ingredient, and a method for controlling phytopathogenic fungi, wherein the compound or the salt is applied.
  • the present invention relates to a method for controlling plant diseases.
  • Patent Document 1 discloses an aminoquinazoline compound having a piperidine ring substituted at the 3-position with an ethenyl group, which is useful as an antibacterial agent.
  • Patent Documents 2 and 3 describe aminopyrimidine compounds characterized by substituents on the pyrimidine ring, which are useful as BTK (Bruton's tyrosine kinase) inhibitors.
  • Patent Document 4 discloses an aminothienopyrimidine compound substituted with an alkenyl group as a drug useful for neuropathic pain.
  • diflumetrim which is an aminopyrimidine compound is used as an agricultural and horticultural fungicide, it does not have a nitrogen-containing saturated heterocyclic ring (nonpatent literature 1).
  • a compound represented by the following formula (I) having a nitrogen-containing saturated heterocyclic ring that is useful as an agricultural and horticultural fungicide is not known.
  • 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 has various plant diseases.
  • the present invention was completed by obtaining knowledge that an excellent control effect was exhibited.
  • the present invention applies the compound represented by formula (I) or a salt thereof (hereinafter also referred to as the present compound), an agricultural and horticultural fungicide containing the present compound as an active ingredient, and the present compound.
  • the present compound an agricultural and horticultural fungicide containing the present compound as an active ingredient, and the present compound.
  • A is a group represented by the following formula
  • X 1 to X 18 , X 20 , X 21 , X 23 to X 26 , and X 28 to X 33 are the same or different and each represents hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, Selected from the group consisting of alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio, haloalkylthio, alkylamino and dialkylamino;
  • X 19 and X 27 are the same or different and are selected from the group consisting of hydrogen, alkyl, haloalkyl and alkoxycarbonyl;
  • X 22 is selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio, haloalkylthio, al
  • R 2 is hydrogen, alkyl or haloalkyl
  • B is pyrrolidine, piperidine or azepan, which may be crosslinked with alkylene
  • R 3 is halogen or alkyl
  • n is an integer from 0 to 4
  • Zb is a bond or a group represented by -Zb 1 -Zb 2-
  • Zb 1 is carbonyl, thiocarbonyl, sulfonyl, sulfinyl, alkylene or haloalkylene
  • Zb 2 is a bond, carbonyl, thiocarbonyl, sulfonyl, sulfinyl, alkylene, haloalkylene or —NR a —
  • R a is hydrogen Or Zb 1 and Zb 2 are not the same
  • R 4 is alkyl which may be substituted by Y 1, alkenyl which may be substituted with Y 1, cycloalkyl which may be substituted by Y 2, hydroxy
  • the compound of the present invention has a high control effect against a wide range of plant pathogens.
  • examples of the 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. Further, the halogen substitution position may be any position.
  • the alkyl or alkyl moiety may be linear or branched, and specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t- Examples thereof include those of C 1-6 such as butyl, pentyl, isopentyl, neopentyl and hexyl.
  • alkenyl or alkenyl moiety may be linear or branched, and specific examples thereof include vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl. , 3-butenyl, 1,3-butadienyl, C 2-6 such as 1-hexenyl, and the like.
  • cycloalkyl may be bridged, and specific examples thereof include C 3-10 such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornanyl, adamantyl, and indanyl. Things.
  • examples of the aryl or aryl moiety include those of C 6-10 such as phenyl, naphthyl, and indenyl.
  • the heterocyclyl or heterocyclyl moiety is derived from a saturated or unsaturated ring containing 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom as ring members. Group to be used.
  • the heterocyclyl or heterocyclyl moiety may be monocyclic or polycyclic and may be substituted with an oxo group ( ⁇ O).
  • oxiranyl such as oxiranyl; furyl, dihydrofuryl, tetrahydrofuryl, thienyl, dihydrothienyl, tetrahydrothienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, imidazolinyl, 5-membered rings such as imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; Benzofuranyl, isobenzofuranyl, dihydrobenzofuranyl, dihydroisobenzofura Benzothienyl, isobenzothienyl, dihydrobenzothienyl, dihydrobenz
  • alkylene may be linear or branched, and specific examples thereof include methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, (methyl C 1-6 things like methylene, (ethyl) methylene, (propyl) methylene, (isopropyl) methylene, di (methyl) methylene, (methyl) (ethyl) methylene, 1-methylethylene, 2-methylethylene Is mentioned.
  • A is a group represented by the following formula.
  • X 1 to X 18 , X 20 , X 21 , X 23 to X 26 , and X 28 to X 33 may be the same or different and are each hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy Selected from the group consisting of haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio, haloalkylthio, alkylamino and dialkylamino;
  • X 19 and X 27 may each be the same or different and are selected from the group consisting of hydrogen, alkyl, haloalkyl and alkoxycarbonyl;
  • X 22 is selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio, haloalkylthio
  • X 1 is preferably selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, alkoxycarbonyl, alkylamino and dialkylamino, more preferably hydrogen, alkyl, Selected from the group consisting of haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro and alkoxycarbonyl, more preferably hydrogen or alkyl.
  • X 2 is preferably selected from the group consisting of halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio, haloalkylthio, alkylamino and dialkylamino, and more Preferably, selected from the group consisting of halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio, more preferably halogen, alkyl, haloalkyl, or Alkoxycarbonyl.
  • X 3 is preferably selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, cyano, alkoxycarbonyl, alkylthio, haloalkylthio, alkylamino and dialkylamino, and more Preferably, selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, cyano, alkoxycarbonyl, alkylthio and haloalkylthio, more preferably hydrogen, halogen, alkoxy, or Alkoxycarbonyl. Further, it is preferable that both X 2 and X 3 are not hydrogen.
  • X 4 is more preferably hydrogen.
  • X 5 is more preferably hydrogen or halogen (particularly fluorine).
  • X 6 is more preferably hydrogen.
  • X 7 is preferably selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio, more preferably hydrogen.
  • X 8 is preferably selected from the group consisting of hydrogen, fluorine, chlorine, iodine, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio, and more Preferred is hydrogen or fluorine.
  • X 8 is halogen
  • X 5 is preferably halogen.
  • X 9 , X 10 and X 11 may be the same or different and are preferably hydrogen or alkyl, more preferably hydrogen.
  • X 12 , X 13 , X 14 , X 15 and X 16 are more preferably hydrogen.
  • X 17 and X 18 may be the same or different, and are preferably hydrogen or alkyl, more preferably hydrogen.
  • X 19 is more preferably alkyl.
  • X 20 and X 21 are more preferably hydrogen.
  • X 22 is preferably hydrogen, alkyl, halogen, or haloalkyl, more preferably hydrogen or halogen.
  • X 23 and X 24 are preferably hydrogen or alkyl, and more preferably hydrogen.
  • X 25 and X 26 may be the same or different and are preferably hydrogen, alkyl, halogen, haloalkyl, or alkoxy, more preferably hydrogen or alkyl.
  • X 27 is more preferably an alkyl.
  • X 28 is preferably hydrogen, alkyl, halogen, haloalkyl, or alkoxy, more preferably alkyl.
  • X 29 is more preferably hydrogen or halogen.
  • X 30 is more preferably hydrogen.
  • X 31 and X 32 are more preferably hydrogen.
  • X 33 is more preferably hydrogen or halogen.
  • R 1 is hydrogen, alkyl, cycloalkyl, haloalkyl, or alkoxyalkyl, preferably hydrogen, alkyl, or haloalkyl.
  • Za is a bond or alkylene, more preferably a bond, methylene, ethylene, (methyl) methylene, or (ethyl) methylene.
  • the left side of the wavy line is bonded to the Za group, and the right side is bonded to the B ring.
  • the three carbon atoms constituting the cyclopropylene ring one carbon atom overlapping the wavy line is the B ring. It is also a part of.
  • R 2 is hydrogen, alkyl or haloalkyl, preferably hydrogen or alkyl.
  • the ring represented by B in formula (I) is pyrrolidine, piperidine, or azepane, and may be bridged with alkylene.
  • the alkylene to be bridged is preferably C 1-3 such as methylene and ethylene, and the crosslinking position is not particularly limited.
  • the ring represented by B in formula (I) is preferably piperidine.
  • the ring represented by B may be substituted with R 3 , and when n is 2 or more, 2 or more R 3 may be the same or different. Moreover, the substitution position of R 3 may be any position.
  • R 3 is halogen or alkyl, preferably halogen.
  • Zb is a bond or a group represented by —Zb 1 —Zb 2 —.
  • Zb 1 and Zb 2 are not the same, Zb 1 is carbonyl, thiocarbonyl, sulfonyl, sulfinyl, alkylene or haloalkylene, and Zb 2 is a bond, carbonyl, thiocarbonyl, sulfonyl, sulfinyl, alkylene , Haloalkylene or —NR a — (R a is hydrogen or alkyl).
  • Zb 1 is preferably carbonyl, thiocarbonyl, sulfonyl, or alkylene
  • Zb 2 is preferably a bond, carbonyl, alkylene, haloalkylene, or —NR a — (R a is as defined above. ).
  • Zb examples include a bond, carbonyl, sulfonyl, alkylene, carbonyl-alkylene, carbonyl-haloalkylene, thiocarbonyl-alkylene, alkylene-carbonyl, carbonyl-NR a- (R a is as defined above), Alternatively, thiocarbonyl-NR a — (R a is as defined above) can be mentioned.
  • R 4 is alkyl which may be substituted by Y 1, alkenyl which may be substituted with Y 1, cycloalkyl which may be substituted by Y 2, hydroxy, alkoxy substituted by Y 1, by Y 1 optionally substituted alkenyloxy, Y 2 may aryloxy substituted with, Y good heterocyclyloxy be substituted with, alkylthio be substituted with Y 1, amino which may be substituted by Y 2, aryl which may be substituted by Y 2, or heterocyclyl, optionally substituted by Y 2.
  • the alkyl may be substituted by Y 1, Y 2 which may be substituted with a cycloalkyl, Y 1 in an optionally substituted alkoxy, which may be aryloxy optionally substituted with Y 2, is substituted with Y 2 which may be heterocyclyloxy, aryl which may be substituted by Y 2, or heterocyclyl, optionally substituted by Y 2.
  • the number of substitutions for Y 1 and Y 2 may be 1 or 2 or more, and in the case of 2 or more, these substituents may be the same or different. Further, the substitution position of Y 1 and Y 2 may be any positions.
  • Y 1 include halogen, aryl and the like
  • Y 2 include halogen, alkyl, haloalkyl, alkoxy, nitro, alkoxycarbonyl, alkylcarbonyl and the like.
  • Examples of the salt of the compound of the present invention include any salt that is acceptable in the technical field, for example, salts with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid; tartaric acid, Salts with organic carboxylic acids such as formic acid, acetic acid, citric acid, fumaric acid, maleic acid, trichloroacetic acid and trifluoroacetic acid; methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, mesitylenesulfonic acid and naphthalenesulfonic acid, etc. And salts thereof with sulfonic acid.
  • inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid
  • tartaric acid Salts with organic carboxylic acids such as formic acid, acetic acid, citric acid, fumaric acid, maleic acid, trichloroacetic acid and trifluor
  • 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.
  • Preferred embodiments of the compound of the present invention include the following compounds, but the compound of the present invention is not limited to these.
  • X 1 is selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, alkoxycarbonyl, alkylamino and dialkylamino.
  • Compound or salt thereof is selected from the group consisting of halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio, haloalkylthio, alkylamino and dialkylamino.
  • X 3 is selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, cyano, alkoxycarbonyl, alkylthio, haloalkylthio, alkylamino and dialkylamino; The compound or its salt as described in said (4).
  • X 7 is selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio Its salt.
  • X 8 is selected from the group consisting of hydrogen, fluorine, chlorine, iodine, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio.
  • A is a group represented by the following formula; the other symbols are as defined above; provided that when X 3 is halogen, X 2 is not hydrogen, and the formula (I) Or a salt thereof.
  • X 1 to X 8 are the same or different and are selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio.
  • X 3 is selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, cyano, alkoxycarbonyl, alkylthio and haloalkylthio Or a salt thereof.
  • X 7 is selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, nitro, cyano, alkoxycarbonyl, alkylthio, and haloalkylthio, according to (5 ′) above.
  • X 8 is selected from the group consisting of hydrogen, fluorine, chlorine, iodine, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio.
  • the compound of the present invention can be produced according to the following production method and ordinary salt production method, but is not limited to these methods.
  • the compound of the present invention can be produced by any of the following production methods [1] to [6].
  • the compounds of formula (II) to formula (XI) used in the production methods [1] to [6] commercially available compounds may be used, or those prepared from commercially available compounds by known methods may be used. it can.
  • L 1 is halogen (chlorine, bromine, iodine, etc.), and other symbols are as defined above.
  • the compound of formula (I) can be produced by reacting the compound of formula (II) with the compound of formula (III).
  • the compound of formula (II) may use an acid addition salt thereof (for example, hydrochloride, hydrobromide, methanesulfonate, trifluoroacetate, etc.).
  • 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 is not particularly limited as long as the reaction proceeds.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate
  • alkali metal hydrogen carbonates such as sodium hydrogen carbonate
  • organic amines such as triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine; and the like.
  • the base can be used in a proportion of 1 to 20 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (II).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • alcohols such as methanol, ethanol, propanol and butanol
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • diethyl ether, diisopropyl ether, dioxane Ethers such as butyl ether, tetrahydrofuran, dioxane and ethylene glycol dimethyl ether
  • nitriles such as acetonitrile and propionitrile
  • halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride and 1,2-dichloroethane
  • N Acid amides such as N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidinone
  • sulfoxides such as dimethyl sulfoxide
  • sulfones such as s
  • the reaction temperature is usually 0 to 200 ° C, preferably 70 to 120 ° C.
  • the reaction time is usually 1 to 48 hours.
  • L 2 is halogen (chlorine, bromine, iodine, etc.) or hydroxy
  • Zb ′ is a bond or carbonyl, and other symbols are as defined above.
  • a compound of formula (I ′) can be obtained by reacting a compound of formula (IV) with a compound of formula (V).
  • the compound of formula (IV) may use an acid addition salt thereof (for example, hydrochloride, hydrobromide, methanesulfonate, trifluoroacetate, etc.).
  • the compound of the formula (V) is used in a ratio of 1 to 50 equivalents, preferably 2 to 10 equivalents with respect to 1 equivalent of the compound of the formula (IV).
  • the reaction can usually be carried out in the presence of a base.
  • 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 hydrogen carbonates such as sodium hydrogen carbonate
  • organic amines such as triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine; and the like.
  • the base is used in a proportion of 1 to 20 equivalents, desirably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (IV).
  • the base is preferably used in a ratio of 2 to 6 equivalents per 1 equivalent of the acid addition salt.
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • aromatic hydrocarbons such as benzene, toluene, and xylene
  • ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, and ethylene glycol dimethyl ether.
  • Nitriles such as acetonitrile and propionitrile; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride and 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N- Acid amides such as methyl pyrrolidinone; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane; Phosphoric amides such as hexamethylphosphoramide; and a mixed solvent thereof. It is appropriately selected but, among them acid amides are preferred.
  • the reaction temperature is usually 0 to 200 ° C, preferably 70 to 120 ° C.
  • the reaction time is usually 1 to 48 hours.
  • this reaction can be usually carried out in the presence of a condensing agent and optionally in the presence of a base.
  • the condensing agent is not particularly limited as long as the reaction proceeds.
  • carbodiimides such as N, N′-dicyclohexylcarbodiimide; benzotriazol-1-yloxy-trisdimethylaminophosphonium salt, O- (benzotriazole-1 -Yl) -N, N, N ′, N′-tetramethyluronium BOP reagents such as tetrafluoroborate;
  • the condensing agent is used in a proportion of 1 to 20 equivalents, desirably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (IV).
  • 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 hydrogen carbonates such as sodium hydrogen carbonate
  • alkalis such as calcium carbonate And earth metal carbonates
  • organic amines such as triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine; and the like.
  • the base is used in a proportion of 1 to 20 equivalents, preferably 2 to 5 equivalents, relative to 1 equivalent of the compound of formula (IV).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • aromatic hydrocarbons such as benzene, toluene, and xylene
  • ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, and ethylene glycol dimethyl ether.
  • Nitriles such as acetonitrile and propionitrile; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; 1 type or 2 types or more are appropriately selected from the following: phosphoric acid amides such as hexamethylphosphoramide; and mixed solvents thereof, among which ethers and acid amides are preferable.
  • the reaction temperature is usually 0 to 200 ° C, preferably 70 to 120 ° C.
  • the reaction time is usually 1 to 48 hours.
  • L 3 is isocyanato or isothiocyanate
  • Zb ′′ is — (C ⁇ O) —NH— or — (C ⁇ S) —NH—, and other symbols are as defined above.
  • a compound of formula (I ′′) can be produced by reacting a compound of formula (IV) with a compound of formula (VI).
  • the compound of formula (IV) may use an acid addition salt thereof (for example, hydrochloride, hydrobromide, methanesulfonate, trifluoroacetate, etc.).
  • the compound of formula (VI) is used in a ratio of 1 to 50 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the compound of formula (IV).
  • this reaction can usually be carried out in the presence of a base.
  • 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 hydrogen carbonates such as sodium hydrogen carbonate
  • alkalis such as calcium carbonate And earth metal carbonates
  • organic amines such as triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine; and the like.
  • the base is used in a ratio of 1 to 20 equivalents, preferably 2 to 5 equivalents, relative to 1 equivalent of the acid addition salt of formula (IV).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • alcohols such as methanol, ethanol, propanol and butanol
  • ketones such as acetone and methyl ethyl ketone
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • Ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether
  • nitriles such as acetonitrile and propionitrile
  • halogens such as chloroform, dichloromethane, carbon tetrachloride and 1,2-dichloroethane Hydrocarbons
  • acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone
  • sulfoxides such as dimethyl
  • the reaction temperature is usually 0 to 200 ° C, preferably 70 to 120 ° C.
  • the reaction time is usually 1 to 48 hours.
  • R 1a is alkyl, cycloalkyl, haloalkyl, alkoxyalkyl, or alkoxycarbonyl, and other symbols are as defined above.
  • the compound of the formula (I ′′ ′′) can be produced by reacting the compound of the formula (I ′ ′′) with the compound of the formula (VII).
  • the compound of the formula (I ′ ′′) can be produced by any of the above production methods [1] to [3].
  • the compound of the formula (VII) is used in a ratio of 1 to 50 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of the formula (I ′ ′′).
  • 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 hydrogen carbonates such as sodium hydrogen carbonate
  • alkalis such as calcium carbonate And earth metal carbonates
  • organic amines such as triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine; and the like.
  • the base is used in a proportion of 1 to 20 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of (VII).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • alcohols such as methanol, ethanol, propanol and butanol
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • Ethers such as tetrahydrofuran, dioxane and ethylene glycol dimethyl ether
  • nitriles such as acetonitrile and propionitrile
  • halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride and 1,2-dichloroethane
  • N, N -Acid amides such as dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidinone
  • sulfoxides such as dimethyl sulfoxide
  • sulfones such as sulf
  • the reaction temperature is usually 0 to 200 ° C, preferably 70 to 120 ° C.
  • the reaction time is usually 1 to 48 hours.
  • L 4 is a leaving group (chlorine, bromine, iodine, trifluoromethanesulfonyloxy, etc.), R A is alkyl, and other symbols are as defined above.
  • the production method [5] can be carried out by reacting the compound of formula (VIII), carbon monoxide and the compound of formula (IX) in the presence of a base and a transition metal catalyst.
  • Carbon monoxide is usually used in an amount of 1 to 10 equivalents, preferably 1 to 4 equivalents, relative to 1 equivalent of the compound of formula (VIII).
  • the pressure is usually 0.1 to 10 MPa, preferably 0.5 to 5 MPa. However, depending on the reaction conditions, amounts and pressures outside these ranges can be used.
  • the compound of the formula (IX) can be used in an amount of 1 equivalent or more with respect to 1 equivalent of the compound of the formula (VIII), preferably 3 equivalents or more.
  • An excess amount of the compound of formula (IX) can also be used as a solvent. Usually, 1000 equivalent or less is preferable.
  • the base examples include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metals such as sodium carbonate and potassium carbonate. Carbonates; alkaline earth metal hydrogen carbonates such as calcium hydrogen carbonate and magnesium hydrogen carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; alkali metal carboxylates such as sodium acetate and potassium acetate Carboxylic acid alkaline earth metal salts such as calcium acetate and magnesium acetate; trimethylamine, triethylamine, diisopropylamine, triisopropylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, 2,6-dimethylpyri Gin, 4-pyrrolidinopyridine, N-methylmorpholine, N, N-dimethylaniline, N, N-diethylaniline, N-ethy
  • the base can be generally used in an amount of 1 to 10 equivalents, preferably 1 to 3 equivalents, relative to 1 equivalent of the compound of the formula (VIII). However, depending on the reaction conditions, an amount outside this range can 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 the carbonylation reaction of organic halides can be used, and a transition metal catalyst containing palladium is particularly useful for this reaction.
  • palladium-carbon palladium chloride, palladium acetate, dichlorobis (acetonitrile) palladium, dichlorobis (benzonitrile) palladium, bis (dibenzylideneacetone) palladium, bis (acetylacetonato) palladium, dichlorobis (triphenylphosphine) palladium, dichlorobis (Triisopropylphosphine) palladium, tetrakis (triphenylphosphine) palladium, dichloro (1,4-bis (diphenylphosphino) butane) palladium, dichlorobis (triphenylphosphite) palladium and the like.
  • 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 include 3-bis (diphenylphosphino) propane, 1,4-bis (diphenylphosphino) butane, 1,1′-bis (diphenylphosphino) ferrocene, and triphenylphosphite.
  • the transition metal catalyst is usually used in an amount of 0.001 to 0.5 equivalent, preferably 0.001 to 0.1 equivalent, relative to 1 equivalent of the compound of the formula (VIII).
  • the ligand can be used usually in an amount of 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 in the presence of a solvent, if necessary.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • Halogenated hydrocarbons such as chlorobenzene, dichloromethane and dichloroethane
  • ethers such as diethyl ether, butyl ethyl ether, methyl tert-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane
  • nitriles such as acetonitrile and propionitrile
  • N N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, acid amides such as 1,3-dimethyl-2-imidazolidin
  • Za ′ is alkylene
  • Za ′′ is alkylene having 1 fewer carbon atoms than Za ′, and each symbol is as defined above.
  • the production method [6] can be carried out by reacting the compound of formula (X) with formula (XI) in the presence of a reducing agent.
  • the reducing agent is usually used in an amount of 1 to 10 equivalents, preferably 1 to 4 equivalents, relative to 1 equivalent of the compound of the formula (X). However, depending on the reaction conditions, amounts outside these ranges can also be used.
  • the compound of the formula (XI) can be used usually in an amount of 1 to 10 equivalents, desirably 1 to 4 equivalents with respect to 1 equivalent of the compound of the formula (X).
  • Examples of the reducing agent include sodium cyanoborohydride, sodium triacetoxyborohydride, sodium borohydride and the like, and sodium triacetoxyborohydride is preferable.
  • This reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; aromatic hydrocarbons such as benzene, toluene and xylene; Halogenated hydrocarbons such as chlorobenzene, dichloromethane, dichloroethane; ethers such as diethyl ether, butyl ethyl ether, methyl tert-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane; N, N-dimethylformamide, N, N-dimethyl Acid amides such as acetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon
  • the compounds of the present invention include, for example, Mastigomycotina, Ascomycotina, Basidiomycotina, Deuteromycotina, Zygomycotina, etc. Can control plant pathogens belonging to.
  • plant pathogen More specific examples include the following.
  • Erysiphe genus such as wheat powdery mildew (Erysiphe graminis); Sphaerotheca genus Sphaerotheca humuli, genus Sphaerotheca humuli Genus Uncinula such as Uncinula necator; Podosphaera genus such as Podosphaera leucotricha; Mycosphaerella pinodes, Mycosphaerellanode ), Banana black sigatoka (Mycosphaerella musicola), oyster circle deciduous fungus (Mycosphaerella nawae), Mycosphaerella fragariae genus Mycosphaerella (Mycosphaerella) genus; Venturia genus such as Venturia nashicola); Pyrenophora teres, Pyrenophora graminea, such as Pyrenophora ;; Sclerotiniains
  • Genus Diaporthe sp. Genus Monilinia, such as Monilinia mali, Monilinia fructicola; A genus Glomerella such as Glomerella cingulata; a genus Magnaporthe such as Magnaporthe grisea; and the like.
  • Rhizoctonia genus such as rice rot fungus (Rhizoctonia solani); Ustilago genus such as wheat naked smut fungus (Ustilago nuda); Oat crown rust fungus (Puccinia coronata), Puccinia recondita, Puccinia striiformis genus Puccinia, and the like.
  • Septoria nodorum Septoria tritici genus Septoria tritici
  • Botrytis cinerea genus Botrytis ;
  • Cercospora genus such as sugar beet brown fungus (Cercospora beticola), oyster horn spot fungus (Cercospora kakivola);
  • Colletotrichum genus such as Colletotrichum orbiculare; apple pathotype), pear black spot fungus (Alternaria alternata Japanese pear pathotype), potato summer or tomato ring mold fungus (Alternaria solani), cabbage black spot fungus (Alternaria brassicae), Alternaria spp.
  • Pseudocercosporella (Pseudocercosporella herpotrichoides) Genus; genus Pseudocercospora such as Pseudocercospora vitis; genus Rhynchosporium such as Rhynchosporium secalis; genus Rhynchosporium; Cladosporium carpophilum Cladosporium genus; Phomopsis genus such as Pomoopsis sp .; Gloeosporium genus such as Gloeosporium kaki; Tomato leaf mold (Fulvia fulva) such as (Fulvia fulva); Corynespora ⁇ genus such as cucumber brown spot fungus (Corynespora cassiicola);
  • zygomycetes examples include the genus Rhizopus ⁇ ⁇ ⁇ stronifer and the genus Rhizopus such as Rhizopus nigricans.
  • the compound of the present invention is useful as an active ingredient of agricultural and horticultural fungicides, such as rice blast, sesame leaf blight, coat blight; wheat powdery mildew, red mold, rust, snow rot , Bare black spot disease, eye spot disease, leaf blight disease, blight disease; citrus black spot disease, common scab; apple monilia disease, powdery mildew, spotted leaf disease, black star disease, anthracnose disease, brown spot disease, Ring rot, soot spot, soot spot, sunspot disease; pear scab, black spot, powdery mildew, plague; pear ring rot, powdery mildew; Homopsis rot; grape black rot, late rot, powdery mildew, downy mildew, gray mold, brown spot, branch rot; oyster anthracnose, defoliation, powdery mildew, soot spot; Anthracnose of cucumber, powdery mildew, vine blight, downy mildew, plague
  • 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, It can be used in various forms such as liquids, pastes, aerosols, microdispersions, etc., but it can be made into any conventional form used in the art as long as it meets the purpose of the present invention. it can.
  • 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. Therefore, the content of the compound of the present invention in the agricultural and horticultural fungicide is 0.005 to 95% by weight, preferably 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 defined unconditionally, but in the case of foliage treatment, it is usually 0.1 to 10,000 ppm per active ingredient, Desirably, it is 1 to 2,000 ppm. In the case of soil treatment, it is usually 10 to 100,000 g / ha, preferably 200 to 20,000 g / ha. In the case of 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 is generally applied for application of its various preparations or dilutions thereof, that is, spraying (spraying, spraying, misting, atomizing, dusting, water surface application, etc.), soil application (Mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.) can be used. It can also be applied by the so-called ultra-low concentration 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 agricultural chemicals such as bactericides, insecticides, acaricides, nematicides, soil insecticides, antiviral agents, attractants, herbicides, plant growth preparations as necessary. It can be mixed and used together.
  • bactericide for example, anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil; Tria like 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; Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole, tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole
  • Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil; Tria like 5-chloro
  • 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, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiophos, prothiophos Fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate ), Sulprofos, thiometon, bamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl, pirimiphos-methyl Propapho
  • Microbial pesticides such as: avermectin, emamectin benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin ), Antibiotics such as emamectin, spinetoram and semi-synthetic antibiotics; natural products such as azadirachtin and rotenone; repellents such as deet; Mixed with , Can be used together.
  • Synthesis example 2 Synthesis process 1 of 2-phenyl-1- (4- (2- (quinazolin-4-ylamino) ethyl) piperidin-1-yl) ethanone (Compound No. 1-28) Synthesis of t-butyl 4- (2- (quinazolin-4-ylamino) ethyl) piperidine-1-carboxylate (Compound No. 1-18)
  • N- (2- (piperidin-4-yl) ethyl) quinazolin-4-amine hydrochloride (0.1 g), 2-chlorophenylacetic acid (0.06 g), diisopropylethylamine (0.13 g) and N, N-dimethylformamide (5 mL )
  • O- (benzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium tetrafluoroborate (TBTU) (0.16 g) was added at the same temperature. The mixture was stirred for 1 hour. Then, it heated up to room temperature and stirred for 17 hours.
  • Tables 1 to 3 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 represents methyl
  • Et represents ethyl
  • Pr represents propyl
  • iPr represents isopropyl
  • nBu represents butyl
  • iBu represents isobutyl
  • tBu represents t-butyl.
  • “ ⁇ ” in the Za column and the Zb column indicates a bond, and when the (R 3 ) n column is blank, n indicates 0.
  • “*” indicates binding at the relevant part.
  • Table 4 shows 1 H-NMR data [measured by 1 H-nuclear magnetic resonance spectroscopy (Varian NMR-300 MHz); ⁇ is a chemical shift value (ppm)] of some of the compounds of the present invention. .
  • 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 when reaching the leaf stage from 1.5 to 2.5, a mixed drug solution with each test compound adjusted to a predetermined concentration is applied to the spray gun. 10 ml per seedling was sprayed. After the drug solution was dried, it was inoculated with conidia spores of wheat powdery mildew (Erysiphe graminis) and kept in a constant temperature room at 20 ° C. The number of lesions was investigated 7 or 8 days after the inoculation, and the control index was determined according to the evaluation criteria.
  • Test example 2 (wheat blight prevention effect test) Wheat (variety: Norin 61) is cultivated in a plastic pot with a diameter of 6.0 cm, and when the 1.5 to 2.5 leaf stage is reached, the chemical solution in which the compound of the present invention is adjusted to a predetermined concentration is spray gun. A sufficient amount was sprayed. After the drug solution was dried, a conidial spore suspension of wheat wilt (Septoria nodorum) was spray-inoculated and kept in an inoculation box at 20 ° C. for about 1 day, and then kept in a constant temperature room at 20 ° C. The number of lesions was investigated 10 days or 11 days after the inoculation, and the control index was determined according to the above evaluation criteria. Compound No. When 1-1, 1-128, 1-133, 1-151, 1-205, 1-246, 2-8, and 3-7 were tested, the control index was 4 or more at 400 ppm.
  • Test example 3 (wheat red rust prevention effect test) Growing wheat (variety: Norin 61) in a plastic pot with a diameter of 6.0 cm, and when reaching the leaf stage from 1.5 to 2.5, a mixed drug solution with each test compound adjusted to a predetermined concentration is spray gun 10 ml per seedling was sprayed. After the drug solution was dried, the conidia of Puccinia recondita were sprinkled and inoculated, kept in an inoculation box at 20 ° C. for about 1 day, and then kept in a constant temperature room at 20 ° C. The number of lesions was investigated 7 to 9 days after the inoculation, and the control index was determined according to the above evaluation criteria.
  • Test Example 4 Cultivate tomato (variety: yellow pair, the world's best) in a 7.5cm diameter plastic pot, and when the 3 to 6 leaf stage is reached, use a spray gun to squeeze a sufficient amount of the drug solution adjusted to the prescribed concentration Scattered. After the chemical solution was dried, a zoosporangium suspension of Phytophthora infestans was spray-inoculated and kept in a constant temperature room at 20 ° C. The lesion area was investigated 3 or 4 days after the inoculation, and the control index was determined according to the above evaluation criteria.
  • Test Example 5 Cucumber downy mildew prevention effect test
  • a cucumber variety: Sagamihanjiro
  • a chemical solution in which the compound of the present invention is adjusted to a predetermined concentration is spray gun.
  • a sufficient amount was sprayed.
  • a zoosporangium suspension of cucumber downy mildew (Pseudoperonospora cubensis) was spray-inoculated, kept in an inoculation box at 20 ° C. for about 1 day, and kept in a constant temperature room at 20 ° C.
  • the lesion area was examined 7 or 8 days after the inoculation, and the control index was determined according to the above evaluation criteria.
  • Test Example 6 Cucumber powdery mildew prevention effect test
  • a cucumber cucumber (variety: Sagamihanjiro) is cultivated in a 7.5 cm diameter plastic pot, and when the 1.5 to 2.5 leaf stage is reached, a chemical solution in which the compound of the present invention is adjusted to a predetermined concentration is spray gun. A sufficient amount was sprayed. After the chemical solution was dried, a spore suspension of Sphaerotheca fuliginea 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.
  • Formulation Example 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 added to the mixed and crushed stock solution, and the mixture is uniformly mixed, granulated, and dried to obtain a granular 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) Compound of the present invention 2.5 parts by weight (2) N-methyl-2-pyrrolidone 2.5 parts by weight (3) Soybean oil 95.0 parts by weight The above is uniformly mixed, dissolved and sprayed in a trace amount This is an 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 pathogenic bacteria and also has high safety, it is useful as an agricultural and horticultural fungicide.
  • the entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2013-232450 filed on November 8, 2013 are incorporated herein as the disclosure of the specification of the present invention. Is.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

　La présente invention concerne un fongicide agricole et horticole manifestant un puissant effet de lutte contre un large éventail d'agents phytopathogènes. La présente invention concerne un composé représenté par la formule (I) ou un sel de celui-ci, un fongicide agricole et horticole contenant ce composé ou un sel de celui-ci comme principe actif, et un procédé de lutte contre des agents phytopathogènes et un procédé de lutte contre des maladies de plantes par l'application de ce composé ou d'un sel de celui-ci. [Chaque symbole est tel que défini dans la description.]
PCT/JP2014/079488 2013-11-08 2014-11-06 Composé hétérocyclique saturé contenant de l'azote WO2015068773A1 (fr)

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JP2013-232450 2013-11-08
JP2013232450A JP2017001954A (ja) 2013-11-08 2013-11-08 含窒素飽和複素環化合物

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IL259199A (en) * 2015-11-12 2018-07-31 Afasci Inc Inhibitors of ion channel, preparations containing them and their uses
CN110770222A (zh) * 2017-06-28 2020-02-07 葛兰素史克知识产权开发有限公司 吲哚胺2,3-双加氧酶的调节剂
CN112236427A (zh) * 2018-08-20 2021-01-15 住友化学株式会社 苯并噁唑化合物及其用途

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CN110759913B (zh) * 2018-07-26 2022-01-28 南开大学 吲哚酰腙衍生物及其制备方法和在防治植物病毒、杀菌、杀虫方面的应用

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Cited By (6)

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Publication number Priority date Publication date Assignee Title
IL259199A (en) * 2015-11-12 2018-07-31 Afasci Inc Inhibitors of ion channel, preparations containing them and their uses
EP3340988A4 (fr) * 2015-11-12 2019-05-15 Afasci, Inc. Composés inhibiteurs de canaux ioniques, formulations pharmaceutiques, et utilisations
US10562857B2 (en) 2015-11-12 2020-02-18 Afasci, Inc. Ion channel inhibitory compounds, pharmaceutical formulations, and uses
CN110770222A (zh) * 2017-06-28 2020-02-07 葛兰素史克知识产权开发有限公司 吲哚胺2,3-双加氧酶的调节剂
CN112236427A (zh) * 2018-08-20 2021-01-15 住友化学株式会社 苯并噁唑化合物及其用途
CN112236427B (zh) * 2018-08-20 2023-10-03 住友化学株式会社 苯并噁唑化合物及其用途

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