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WO2020050297A1 - Agent de lutte contre les maladies végétales - Google Patents

Agent de lutte contre les maladies végétales Download PDF

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Publication number
WO2020050297A1
WO2020050297A1 PCT/JP2019/034715 JP2019034715W WO2020050297A1 WO 2020050297 A1 WO2020050297 A1 WO 2020050297A1 JP 2019034715 W JP2019034715 W JP 2019034715W WO 2020050297 A1 WO2020050297 A1 WO 2020050297A1
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group
formula
substituted
groups selected
carbon atoms
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English (en)
Japanese (ja)
Inventor
憲太朗 山本
聡 畠山
賢司 梅村
大貴 永田
友紀子 瀧口
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Meiji Seika Kaisha Ltd
Meiji Seika Pharma Co Ltd
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Meiji Seika Kaisha Ltd
Meiji Seika Pharma Co Ltd
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Priority claimed from JP2018166473A external-priority patent/JP2021185128A/ja
Priority claimed from JP2018171046A external-priority patent/JP2021185129A/ja
Priority claimed from JP2019139210A external-priority patent/JP2021185130A/ja
Application filed by Meiji Seika Kaisha Ltd, Meiji Seika Pharma Co Ltd filed Critical Meiji Seika Kaisha Ltd
Publication of WO2020050297A1 publication Critical patent/WO2020050297A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A01N43/48—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
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N43/58—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
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/72—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
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • A01N43/86—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 six-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
    • 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
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring

Definitions

  • the present invention relates to a plant disease controlling agent. More specifically, the present invention relates to a plant disease control agent that protects plants from diseases caused by oomycetes and soil diseases.
  • the present application is filed in Japan with Japanese Patent Application No. 2018-166473 filed on Sep. 6, 2018, Japanese Patent Application No. 2018-171046 filed on Sep. 13, 2018, and on July 29, 2019. Priority is claimed based on Japanese Patent Application No. 2019-139210, the content of which is incorporated herein by reference.
  • the physical resistance mechanism is, for example, a coating material such as a cuticle layer made of wax or the like, or a cell wall, and serves as a barrier for the entrance of pathogenic bacteria.
  • the chemical resistance mechanism is a system that inhibits the growth of pathogenic bacteria, and includes, for example, resistance factors accumulated innately in plants and resistance factors inducibly biosynthesized and accumulated. Can be
  • TMV tobacco mosaic virus
  • oomycetes Diseases caused by oomycetes are one of the important diseases of crops, and control methods using fungicides are common.
  • the fungicide is a disease that is difficult to control because it has a large environmental load and the presence of drug-resistant bacteria is known, so that the usable drug and the number of times that it can be used are limited.
  • soil diseases are generally controlled by soil disinfection, but pesticides used in these methods have a large environmental load.
  • this control method requires a large amount of labor and involves dangerous work, so it is a disease that is difficult to control. Therefore, if a resistance inducer for these diseases that can be used in spraying treatment or irrigation treatment is put to practical use, its usefulness as a simple and safe method is high.
  • Patent Documents 1 to 9 It has been disclosed that isonicotinic acid derivatives have a plant controlling effect.
  • Patent Documents 1, 2, 7, 8, and 9 show effects on oomycetes, but it is known that plant disease control effect is sometimes weak.
  • Patent Document 10 an isonicotinic acid compound has an effect of killing a plant (Patent Document 10), and it is known that phytotoxicity occurs in controlling plant diseases.
  • Patent Document 10 there is no specific description about the effect on soil disease.
  • Acetylsalicylic acid induces resistance to tobacco mosaic virus in tobacco, Virology, 99, 410 (1979)
  • An object of the present invention is to provide a plant disease controlling agent.
  • the present inventor has studied the fluorine-substituted pyridine compound in detail, and has found a compound that exhibits a high control effect on plant diseases by exhibiting resistance-inducing activity without directly exhibiting antibacterial activity against pathogenic bacteria. Completed the invention.
  • a plant disease controlling agent comprising a compound represented by the following formula (1) as an active ingredient.
  • X 1 and X 4 may be the same or different and represent a hydrogen atom, a fluorine atom, a chlorine atom or a trifluoromethyl group, and any one of X 1 and X 4 Represents a fluorine atom or a trifluoromethyl group, and X 2 and X 3 may be the same or different and are a hydrogen atom, a fluorine atom, a chlorine atom or a methyl group, provided that X 1 , X 2 and When any one of X 4 represents a fluorine atom, any one of the other two does not represent a hydrogen atom; X a is a group represented by the following formula (2), (3), (4), (5) or (6);
  • J represents an oxygen atom or a sulfur atom
  • A is Carbon number which may be substituted by 1 to 3 groups selected from the group consisting of the following group C, thiol group, methoxycarbonyl group, ethoxycarbonyl group, methoxy group, and N-tert-butoxycarbonylamino group
  • An alkyl group of 1 to 12 An alkenyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C, An alkynyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C, An alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following group C, An alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C, An alkylsulfonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3
  • X 1 , X 2 , X 3 and X 4 are the same as defined in the formula (1),
  • Q is a divalent group represented by the formula: —O— (CH 2 ) n—O—
  • a formula: —NH— (CH 2 ) n— A divalent group represented by O—
  • a formula: —O—CH 2 —CH CH—CH 2 —O—
  • a divalent group represented by the formula: —NH—CH 2 —CH CH—CH 2 —O—
  • a divalent group represented by the formula: —NH—CH 2 —CH CH—CH 2 —NH— Divalent group, cyclohexane-1,4-diyldioxy group, cyclohexane-1,4-diyldiamino group, divalent group represented
  • Gb is an oxygen atom, a sulfur atom, or a divalent group represented by the formula: —SO 2 —
  • Q represents an oxygen atom, a sulfur atom, a divalent group represented by the formula: —NH—, or a formula: —N (CH 3 ) —
  • a divalent group
  • Aa represents a piperidin-1-yl group, a 1-methyl-1-H-pyrrol-2-yl group, a morpholin-4-yl group, an indoline-1-yl group, a benzoisothiazole-3 (2H) -one-1,1-dioxide-2-yl group, piperazin-1-yl group, azetidin-1-yl group, 2,5-dioxopyrrolidin-1-yl group, 3-oxoisothiazole- 2 (3H) -yl group, benzo [d] isothia
  • Xa is a group represented by the above formula (2), and in the above formula (2), Q is an oxygen atom, wherein (1) to (5)
  • Xa is a group represented by the above formula (2), and in the above formula (2), A is substituted by 1 to 3 groups selected from the group C group.
  • An alkylcarbonyl group having 1 to 8 carbon atoms which may be An alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the group C, A phenylcarbonyl group which may be substituted with 1 to 4 groups selected from the group consisting of the group D, a benzyl group, a phenyl group and a phenoxy group; A phenylsulfonyl group optionally substituted with 1 to 4 groups selected from the group D group, or 1 to 5 groups selected from the group consisting of the group D group, phenoxy group and benzyl group
  • the plant disease controlling agent according to any one of (1) to (7), which is a phenyl group which may be substituted.
  • X a is a group represented by the formula (6), wherein the formula (6), Ja and Jb is an oxygen atom, (1) -
  • the plant disease controlling agent according to any one of (4).
  • a method for controlling plant diseases which comprises contacting the plant disease controlling agent according to any one of (1) to (9) with a plant or a seed, or containing the agent in a cultivation bed.
  • a plant disease controlling agent and a plant disease controlling method can be provided.
  • the plant disease controlling agent of the present invention has excellent resistance-inducing activity, and is useful for controlling plant diseases (preferably, diseases caused by oomycetes or soil diseases).
  • the present invention provides a plant disease controlling agent comprising a compound represented by the following formula (1) as an active ingredient. More preferably, the present invention provides a soil disease controlling agent containing a compound represented by the following formula (1) as an active ingredient. In one embodiment, the present invention provides a compound represented by the following formula (1).
  • X 1 and X 4 may be the same or different and represent a hydrogen atom, a fluorine atom, a chlorine atom or a trifluoromethyl group, and any one of X 1 and X 4 Represents a fluorine atom or a trifluoromethyl group.
  • X 2 and X 3 may be the same or different and are a hydrogen atom, a fluorine atom, a chlorine atom or a methyl group. However, in formula (1), when any one of X 1 , X 2 and X 4 represents a fluorine atom, any one of the other two does not represent a hydrogen atom.
  • X 1 , X 2 , X 3 and X 4 are preferably a hydrogen atom or a fluorine atom. Further, X 1 and X 4 are preferably a fluorine atom. Further, it is preferable that X 2 and X 3 is a hydrogen atom or a fluorine atom, it is preferable that at least one of X 2 and X 3 are hydrogen atoms, more that X 2 and X 3 are both hydrogen atoms preferable.
  • Xa is a group represented by the following formula (2), (3), (4), (5) or (6).
  • J represents an oxygen atom or a sulfur atom, preferably an oxygen atom.
  • A represents 1 to 3 groups selected from the group consisting of the following group C, thiol group, methoxycarbonyl group, ethoxycarbonyl group, methoxy group, and N-tert-butoxycarbonylamino group
  • A is an alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following group C; 1 to 3 carbons selected from the following group C
  • a phenylcarbonyl group which may be substituted with 1 to 4 groups selected from the group consisting of the following group D, a benzyl group, a phenyl group and a phenoxy group; 1 to 4 phenylcarbonyl groups selected from the following group D
  • Q is an oxygen atom, a sulfur atom, a divalent group represented by the formula: —NH—, or a formula: —N (CH 3 )
  • a divalent group represented by- preferably, an oxygen atom or a divalent group represented by the formula: -NH-.
  • Aa represents a piperidin-1-yl group, a 1-methyl-1-H-pyrrol-2-yl group, a morpholin-4-yl group, an indoline-1-yl group, a benzoisothiazole-3 (2H) -one-1,1-dioxide-2-yl group, piperazin-1-yl group, azetidin-1-yl group, 2,5-dioxopyrrolidin-1-yl group, 3-oxoisothiazole- 2 (3H) -yl group, benzo [d] isothiazol-2 (3H) -yl group, 1,1-dioxo-3-oxobenzo [d] isothiazol-2 (3H) -yl group, 5,6- It represents a dihydro-4H-1,3-oxazin-2-yl group, a 1H-pyrrol-2-yl group or an isoindoline-2-yl group.
  • Aa is a piperidin-1-yl group, a 1-methyl-1-1H-pyrrol-2-yl group, a morpholin-4-yl group, an indoline-1-yl group, or a benzoisothiazole-3 It is preferably a (2H) -one-1,1-dioxide-2-yl group.
  • Qb represents an oxygen atom, a sulfur atom, a divalent group represented by the formula: —NH— or a divalent group represented by the formula: —N (CH 3 ) —, preferably oxygen Indicates an atom.
  • Ab is a hydrogen atom; a carbon atom which may be substituted with 1 to 3 groups selected from the group consisting of the following group C, a methoxycarbonyl group and an N-tert-butoxycarbonylamino group.
  • m represents an integer of 1 to 3, preferably 1 or 2, and more preferably 1.
  • Z represents a hydrogen atom, a halogen atom or a methyl group, preferably a hydrogen atom.
  • Ja and Jb may be the same or different and represent an oxygen atom or a sulfur atom.
  • G represents a carbon atom which may be substituted by 1 to 3 groups selected from the group consisting of a group C shown below, a thiol group, a methoxycarbonyl group and an N-tert-butoxycarbonylamino group.
  • Ad represents a carbon atom which may be substituted with 1 to 3 groups selected from the group consisting of the following group C groups, thiol groups, methoxycarbonyl groups and N-tert-butoxycarbonylamino groups.
  • Group C includes a halogen atom, a hydroxyl group, an amino group, a cyano group, a 5-methyl-1,3-dioxol-2-one-4-yl group, an isothiazol-5-yl group, a phenylcarbonyl group;
  • a pyridyl group optionally substituted with 1 to 3 groups selected from groups, and a phenyl group optionally substituted with 1 to 4 groups selected from the following group D Preferably, it is substituted with 1 to 3 groups selected from a halogen atom, a hydroxyl group, an amino group, a 5-methyl-1,3-dioxol-2-one-4-yl group, a phenylcarbonyl group and a group of the following group D.
  • Group D includes a halogen atom, a hydroxyl group, an amino group, a dimethylamino group, an acetylamino group, a methylthio group, a methylsulfonyl group, an alkyl group having 1 to 6 carbon atoms which may be substituted by 1 to 3 halogen atoms, An alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a methoxycarbonyl group, an ethoxycarbonyl group, a benzylaminocarbonyl group, an acetoxy group, A group consisting of a nitro group and a cyano group, preferably a halogen atom, a hydroxyl group, an amino group, a methylthio group, an alkyl group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms, An
  • Group E includes pyridyl, thiazolyl, pyrazinyl, pyridazinyl, isoxazolyl, pyrimidinyl, benzimidazolyl, thienyl, furanyl, benzoxanyl, 2,3-dihydrobenzo [b] [1,4] dioxin -6-yl group, dihydrothiazolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoisothiazol-3 (2H) -one-1,1-dioxydyl group, dibenzofuranyl group, isothiazolyl group, and triazolyl group It is a group consisting of
  • the alkyl group having 1 to 12 carbon atoms means a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms.
  • the alkyl group having 1 to 12 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-hexyl, n-hexyl, -Octyl group, n-dodecyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc., preferably, methyl group, ethyl group, n-propyl group, isopropyl group, isobutyl group, tert-butyl group , Cyclopropyl, cyclohexyl, n-hexyl,
  • the alkenyl group having 2 to 8 carbon atoms means a linear, branched or cyclic alkenyl group having one or more double bonds at any position of the alkyl group having 2 to 8 carbon atoms.
  • Examples of the alkenyl group having 2 to 8 carbon atoms include ethenyl, 1-propenyl, 2-propenyl, 2-butenyl, isopropenyl, 3-butenyl, 4-pentenyl, 5-hexenyl, Examples thereof include a 1-cyclohexenyl group, and a 2-propenyl group is preferable.
  • the alkynyl group having 2 to 8 carbon atoms means a linear, branched or cyclic alkynyl group having one or more triple bonds at any position of the alkyl group having 2 to 8 carbon atoms.
  • Examples of the alkynyl group having 2 to 8 carbon atoms include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 3-butynyl group, a cyclopropylethynyl group, and a 2-propynyl group is preferable.
  • the alkyloxy group having 1 to 4 carbon atoms means a group consisting of an oxygen atom substituted with a linear, branched or cyclic alkyl group having 1 to 4 carbon atoms.
  • Examples of the alkyloxy group having 1 to 4 carbon atoms include methoxy, ethoxy, n-propoxy, isopropyloxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, and cyclopropyloxy.
  • the alkyl group having 1 to 8 carbon atoms means a carbonyl group substituted with a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms.
  • Examples of the alkylcarbonyl group having 1 to 8 carbon atoms include a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an isopropylcarbonyl group, an n-butylcarbonyl group, a sec-butylcarbonyl group, an isobutylcarbonyl group, a tert- Examples include a butylcarbonyl group, an n-octylcarbonyl group, a cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group, a cyclohexylcarbonyl group, and the like.
  • the alkylsulfonyl group having 1 to 8 carbon atoms means a sulfonyl group substituted with a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms.
  • alkylsulfonyl group having 1 to 8 carbon atoms examples include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, sec-butylsulfonyl, isobutylsulfonyl, tert- Examples include a butylsulfonyl group, an n-octylsulfonyl group, a cyclopropylsulfonyl group, a cyclobutylsulfonyl group, a cyclopentylsulfonyl group, and a cyclohexylsulfonyl group.
  • Examples of the 5,6,7,8-tetrahydronaphthyl group include a 5,6,7,8-tetrahydronaphthalen-1-yl group and a 5,6,7,8-tetrahydronaphthalen-2-yl group. .
  • a halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the divalent group represented by the formula: -NH- (cyclohexane-1,4-diyl) -O- is a group represented by the formula: -NH- and an oxygen atom at the 1- and 4-positions of the cyclohexane ring, respectively. It is a linked divalent group.
  • the divalent group represented by the formula: -NH- (1,4-phenylene) -O- means that a group represented by the formula: -NH- and an oxygen atom are bonded to the 1- and 4-positions of a benzene ring, respectively. It is a divalent group.
  • Q is a divalent group represented by the formula: —O— (CH 2 ) n—O—, and divalent represented by the formula: —NH— (CH 2 ) n—O—
  • a divalent group represented by the formula: —NH— (CH 2 ) n —NH—; a divalent group represented by the formula: —O—CH 2 —CH CH—CH 2 —O—; :
  • the alkyl group having 1 to 6 carbon atoms which may be substituted by 1 to 3 halogen atoms includes, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec- -Butyl group, isobutyl group, tert-butyl group, n-hexyl group, trifluoromethyl group, chloromethyl group and the like.
  • the alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy Group, sec-butyloxy group, isobutyloxy group, tert-butyloxy group, trifluoromethyloxy group, chloromethyloxy group and the like.
  • A may be substituted with a halogen atom, a hydroxyl group, a 5-methyl-1,3-dioxol-2-one-4-yl group, a phenylcarbonyl group, or one or two halogen atoms.
  • a good pyridyl group a phenyl group optionally having 1 to 2 substituents (preferably, the substituent is a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 4 carbon atoms, One or two substituents selected from the group consisting of a methoxycarbonyl group and an acetoxy group), a cyano group, a thiol group, a methoxycarbonyl group, an ethoxycarbonyl group, a methoxy group, and an N-tert-butoxycarbonylamino group.
  • An alkyl group having 1 to 12 carbon atoms which may have a group; an alkenyl having 2 to 6 carbon atoms which may be substituted with a halogen atom or a phenyl group with 1 to 2 groups; A alkynyl group having 2 to 6 carbon atoms; an alkyloxy group having 1 to 4 carbon atoms; and a halogen atom and an alkyl group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms.
  • Phenylcarbonyl group optionally having 1 to 2 substituents selected; phenylsulfonyl group; halogen atom, hydroxyl group, amino group, dimethylamino group, acetylamino group, methylthio group, methylsulfonyl group, 1-3 Alkyl groups having 1 to 4 carbon atoms which may be substituted by one halogen atom, alkyloxy groups having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms, An alkylcarbonyl group, an ethoxycarbonyl group, a benzylaminocarbonyl group, a nitro group, a cyano group, a phenoxy group, and a substituent selected from the group consisting of a benzyl group; 5,6,7,8-tetrahydronaphthyl group; naphthyl group; an alkyl group having 1 to 4 carbon atoms, an alkyloxy group having 1 to
  • an alkyloxy group having 1 to 4 carbon atoms is preferably selected from the group consisting of an alkyloxy group having 1 to 4 carbon atoms; a halogen atom and an alkyl group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms.
  • a phenylcarbonyl group optionally having 1 to 2 substituents; a phenylsulfonyl group; a halogen atom, a hydroxyl group, an amino group, a dimethylamino group, an acetylamino group, a methylthio group, a methylsulfonyl group, and 1 to 3 halongens
  • An alkyl group having 1 to 4 carbon atoms which may be substituted by an atom, an alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms, an alkylcarbonyl group having 1 to 4 carbon atoms 1 to 5 substituents
  • a phenylcarbonyl group; or a halogen atom, a hydroxyl group, a dimethylamino group, an alkyl group having 1 to 4 carbon atoms which may be substituted with 1 to 3 halogen atoms It may have 1 to 2 substituents selected from the group consisting of an alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 halogen atoms, a nitro group, and a cyano group. More preferably, it is a phenyl group, or a phenyl group optionally having one substituent selected from the group consisting of an alkyl group having 1 to 4 carbon atoms and an alkyloxy group having 1 to 4 carbon atoms. Is more preferable, or a phenyl group substituted with a dimethylamino group is even more preferable.
  • A is an alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the group C; and 1 to 3 groups selected from the groups of the group C
  • Ad is an alkyl group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from the group C group; An alkenyl group having 2 to 3 carbon atoms which may be substituted by 1 to 3 groups; an alkynyl group having 2 to 3 carbon atoms which may be substituted by 1 to 3 groups selected from groups in Group C; An alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from groups in group C; and may be substituted with 1 to 3 groups selected from groups in group D A phenyl group; or a heterocyclic group which may be substituted with 1 to 4 groups selected from the group D groups, and an even more preferred embodiment is an alkyl group having 1 to 4 carbon atoms; An alkyloxy group; or an isothiazolyl group optionally substituted with one or two halogen atoms. .
  • G is more preferably a phenyl group, a phenyl group substituted with a halogen atom, a phenyl group substituted with an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom, A phenyl group substituted with an alkyloxy group having 1 to 4 carbon atoms, or a phenyl group substituted with a cyano group; more preferably, a phenyl group or a phenyl group substituted with an alkyl group having 1 to 4 carbon atoms; Group.
  • Ja and Jb is an oxygen atom.
  • the compound represented by the formula (1) may exist as a hydrate or any solvate, and these hydrates or solvates are also included in the present embodiment. Further, the compound represented by the formula (1) may have an asymmetric carbon, but the asymmetric carbon may have an arbitrary configuration. Pure stereoisomers such as optical isomers or diastereoisomers based on these asymmetric carbons, mixtures of arbitrary stereoisomers, and racemates are all included in the present embodiment. Further, the compound represented by the formula (1) may have one or more double bonds, and may also have a geometric isomer derived from a double bond or a ring structure. It goes without saying that any geometric isomer or a mixture of any geometric isomers in pure form is also encompassed in this embodiment.
  • the compound of this embodiment is produced, for example, according to the following methods A to O, but the production method of the compound of this embodiment is not limited thereto.
  • the compound represented by the formula (2 ′) is a compound of the formula (51) (in the formula (51), X 1 , X 2 , X 3 and X 4 are represented by the formula (1) )) and a compound of formula (52) (wherein A is the same as defined in formula (2), Q ′ is an oxygen atom, a sulfur atom, and the formula: —NH A divalent group represented by-or a divalent group represented by the formula: -N (CH 3 )-) in the presence or absence of a base in the presence of a condensing agent. Is done.
  • the compound represented by the formula (51) a commercially available reagent may be used, or a synthesized compound may be used.
  • Compounds represented by the formula (51) are described, for example, in JP-A-63-93766 and JP-A-1-283270, R. E. Banks, et al., Heterocyclic polyfluoro-compounds. Part XII. Synthesis and some Reactions of 2,3,5,6-tetrafluoro-4-iodopyridine, can be synthesized by a method described in J. Chem. Soc. (C), 2091-2095 (1967), and the like.
  • Solvents used in the reaction include, for example, dichloromethane, chloroform, acetonitrile, ethyl acetate, toluene, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like.
  • Examples of the condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide and the like.
  • Examples of the base used in the reaction include 4-dimethylaminopyridine.
  • the amount of the base used is in the range of 0.01 to 1.2 equivalents based on the carboxylic acid (51).
  • the amount of the condensing agent used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51).
  • the amount of the compound of the formula (52) to be used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51).
  • the reaction temperature is selected, for example, in the range of 0 to 60 ° C, preferably in the range of 10 to 40 ° C.
  • the reaction time ranges, for example, from 10 minutes to 24 hours, preferably from 30 minutes to 4 hours.
  • the compound represented by the formula (2 ′) is a compound of the formula (51) (in the formula (51), X 1 , X 2 , X 3 and X 4 are represented by the formula (1) ) Is the same as the definition in formula (53), via the compound of formula (53) (in formula (53), X 1 , X 2 , X 3 and X 4 are the same as in definition in formula (1)). It can also be manufactured by the following method.
  • the compound of the formula (53) is produced by chlorinating the compound of the formula (51).
  • reaction for example, tetrahydrofuran, toluene, ethyl acetate, dichloromethane, chloroform, acetonitrile and the like can be mentioned, but the reaction can be carried out without a solvent.
  • Examples of the chlorinating agent used in the reaction include thionyl chloride, oxalyl chloride and the like.
  • the amount of the chlorinating agent to be used is in the range of 1 to 5 equivalents based on the compound of the formula (51).
  • the reaction temperature is, for example, in the range of ⁇ 20 to 100 ° C., preferably in the range of 10 ° C. to 80 ° C.
  • Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 2 hours.
  • the compound represented by the formula (2 ') can be produced by reacting the compound of the formula (53) with the compound of the formula (52) in the presence of a base.
  • Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, and a mixed solvent thereof.
  • the base used for the reaction includes triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like.
  • the amount of the base used is in the range of 1 to 10 equivalents based on the carboxylic acid chloride (53).
  • the amount of the compound represented by the formula (52) is in the range of 1 to 2 equivalents based on the carboxylic acid chloride (53).
  • the reaction temperature is, for example, in the range of ⁇ 20 to 100 ° C., preferably in the range of 10 to 50 ° C.
  • Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.
  • the compound represented by the formula (2 ′) can be obtained by adding a compound represented by the formula (51) to a solvent, a chlorinating agent, a compound represented by the formula (52) in the same container without isolating the compound represented by the formula (53).
  • the compound represented by the formula (55) is a compound represented by the formula (51) (in the formula (51), X 1 , X 2 , X 3 and X 4 are represented by the formula (1) And a compound of the formula (54) (in the formula (54), A is the same as the definition in the formula (2) and X 5 represents a halogen atom) in the presence of a base. It can be produced by reacting.
  • the solvent used for the reaction includes, for example, tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like.
  • Examples of the base used in the reaction include sodium hydrogen carbonate, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide and the like.
  • the amount of the base used is in the range of 1.0 to 1.5 equivalents based on the carboxylic acid (51).
  • the amount of the compound represented by the formula (54) is in the range of 1 to 2 equivalents based on the carboxylic acid (51).
  • the reaction temperature is, for example, in the range of ⁇ 20 to 120 ° C., and preferably in the range of 10 to 80 ° C.
  • the reaction time ranges from 10 minutes to 8 hours, preferably from 30 minutes to 6 hours.
  • the compound represented by the formula (55) is a compound represented by the formula (51) (in the formula (51), X 1 , X 2 , X 3 and X 4 are represented by the formula ( By reacting a compound represented by the formula (56) (where A is the same as defined in the formula (2)) in the presence of an acid. Can also be manufactured.
  • Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, and the like, but the reaction can also be performed without a solvent. .
  • the amount of the compound represented by the formula (56) is in the range of 1 to 10 equivalents based on the carboxylic acid (51).
  • the acid used in the reaction includes sulfuric acid, hydrogen chloride and the like, and the amount of the acid used is in the range of 0.01 to 3 equivalents based on the carboxylic acid (51).
  • the reaction temperature is, for example, in the range of ⁇ 20 to 120 ° C., preferably in the range of 10 to 90 ° C.
  • the reaction time ranges from 10 minutes to 8 hours, preferably from 30 minutes to 6 hours.
  • Gb represents an oxygen atom, a sulfur atom or a divalent group represented by the formula: —SO 2 —)) in the presence or absence of a base. It can be produced by reacting in the presence of a condensing agent.
  • Solvents used in the reaction include, for example, dichloromethane, chloroform, acetonitrile, ethyl acetate, toluene, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like.
  • Examples of the condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide and the like.
  • Examples of the base used in the reaction include 4-dimethylaminopyridine.
  • the amount of the base used is in the range of 0.01 to 1.2 equivalents based on the carboxylic acid (51).
  • the amount of the condensing agent used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51).
  • the amount of the compound represented by the formula (57) is in the range of 0.5 to 0.6 equivalent based on the carboxylic acid (51).
  • the reaction temperature is, for example, in the range of 0 to 60 ° C, preferably in the range of 10 to 40 ° C. Reaction times range from 10 minutes to 24 hours, preferably from 30 minutes to 18 hours.
  • the compound represented by the formula (71) is a compound represented by the formula (53) (in the formula (53), X 1 , X 2 , X 3 and X 4 are represented by the formula ( Reaction of the compound of the formula (57) (wherein Q ′ and E are the same as the definition of the formula (57) in the above-mentioned Method E) in the presence of a base. It can also be manufactured by doing.
  • Solvents used in the reaction include, for example, tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and mixtures thereof.
  • the base used for the reaction includes, for example, triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like.
  • the amount of the base used is in the range of 1 to 10 equivalents based on the carboxylic acid chloride (53).
  • the amount of use represented by the formula (57) is in the range of 0.5 to 0.6 equivalent based on the carboxylic acid chloride (53).
  • the reaction temperature is, for example, in the range of ⁇ 20 to 100 ° C., preferably in the range of 10 to 50 ° C.
  • Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 4 hours.
  • the compound represented by the formula (59) is a compound represented by the formula (51) (in the formula (51), X 1 , X 2 , X 3 and X 4 are represented by the formula ( And the compound represented by the formula (58) (in the formula (58), X 5 represents a halogen atom, and E is the same as the definition of the formula (57) in the above-mentioned Method E). ) In the presence of a base.
  • the solvent used for the reaction includes, for example, tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like.
  • Examples of the base used in the reaction include sodium hydrogen carbonate, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide and the like.
  • the amount of the base used is in the range of 1.0 to 1.1 equivalent based on the carboxylic acid (51).
  • the amount of the compound represented by the formula (58) is in the range of 0.5 to 0.6 equivalent based on the carboxylic acid (51).
  • the reaction temperature ranges from -20 to 120 ° C, preferably from 10 to 80 ° C.
  • the reaction time ranges from 10 minutes to 8 hours, preferably from 30 minutes to 6 hours.
  • the compound represented by the formula (3 ′) is a compound represented by the formula (51) (in the formula (51), X 1 , X 2 , X 3 and X 4 are represented by the formula A compound represented by the formula (60) and a compound represented by the formula (60) (wherein Aa is the same as defined in the formula (3)) in the presence or absence of a base. It can be produced by reacting in the presence of a condensing agent.
  • the solvent used for the reaction includes, for example, dichloromethane, chloroform, acetonitrile, ethyl acetate, toluene, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like.
  • Examples of the condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide and the like.
  • Examples of the base used in the reaction include 4-dimethylaminopyridine.
  • the amount of the base used is in the range of 0.01 to 1.2 equivalents based on the carboxylic acid (51).
  • the amount of the condensing agent used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51).
  • the amount of the compound represented by the formula (60) is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51).
  • the reaction temperature ranges from 0 to 60 ° C, preferably from 10 to 40 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.
  • the compound represented by the formula (3 ′) is a compound represented by the formula (53) (in the formula (53), X 1 , X 2 , X 3 and X 4 are represented by the formula The same as defined in (1)) and a compound represented by the formula (60) (wherein Aa is the same as defined in the formula (3)) in the presence of a base. Can also be manufactured.
  • Solvents used for the reaction include, for example, tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and a mixed solvent thereof.
  • the base used for the reaction includes, for example, triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like.
  • the amount of the base used is in the range of 1 to 10 equivalents based on the carboxylic acid chloride (53).
  • the amount of the compound represented by the formula (60) is in the range of 1 to 2 equivalents based on the carboxylic acid chloride (53).
  • the reaction temperature ranges from -20 to 100 ° C, preferably from 10 to 50 ° C.
  • Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 4 hours.
  • the compound represented by the formula (4 ′) is a compound represented by the formula (51) (in the formula (51), X 1 , X 2 , X 3 and X 4 are represented by the formula From the definition in (1), the compound represented by the formula (61) (in the formula (61), X 1 , X 2 , X 3 and X 4 have the same definition as in the formula (1)). ) Can be produced by the following method.
  • the compound represented by the formula (61) can be produced by reducing the compound represented by the formula (51).
  • the solvent used for the reaction includes, for example, tetrahydrofuran, dimethoxyethane, 1,4-dioxane, dichloromethane, chloroform, toluene and the like.
  • reducing agent used in the reaction examples include a borane-tetrahydrofuran complex and a borane-dimethylsulfide complex.
  • the amount of the reducing agent to be used is in the range of 3 to 6 equivalents based on the compound represented by the formula (51).
  • the reaction temperature is in the range of -20 to 80 ° C, preferably in the range of 0 to 40 ° C.
  • the reaction time ranges from 10 minutes to 8 hours, preferably from 30 minutes to 6 hours.
  • the solvent used for the reaction includes, for example, tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and mixtures thereof.
  • the base used for the reaction includes triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like.
  • the amount of the base to be used is in the range of 1 to 10 equivalents based on the compound represented by the formula (61).
  • the amount of the compound represented by the formula (54) is in the range of 1 to 2 equivalents based on the compound represented by the formula (61).
  • the reaction temperature is in the range of ⁇ 20 to 100 ° C., preferably in the range of 10 to 60 ° C.
  • Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.
  • the compound represented by the formula (5 ′) is a compound represented by the formula (53) (in the formula (53), X 1 , X 2 , X 3 and X 4 are represented by the formula (Same as the definition in (1)) and a compound represented by the formula (62) (in the formula (62), X 5 represents a halogen atom, L represents a hydrogen atom or a methyl group, and n represents 1 to Is represented by an integer of 3) in the presence of a base.
  • the solvent used for the reaction includes, for example, tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and a mixed solvent thereof.
  • the base used for the reaction includes, for example, triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like.
  • the amount of the base used is in the range of 1 to 10 equivalents based on the carboxylic acid chloride (53).
  • the amount of the formula (62) is in the range of 1 to 2 equivalents based on the carboxylic acid chloride (53).
  • the reaction temperature ranges from -20 to 100 ° C, preferably from 10 to 90 ° C.
  • the reaction time ranges from 10 minutes to 10 hours, preferably from 30 minutes to 8 hours.
  • the compound represented by the formula (3 ′) is a compound represented by the formula (53) (in the formula (53), X 1 , X 2 , X 3 and X 4 are A compound represented by formula (1)) and a compound represented by formula (60) (in formula (60), Aa is the same as defined in formula (3)) in the presence or absence of an acid. It can also be produced by reacting in the presence.
  • the solvent used for the reaction includes, for example, toluene, dichloromethane, chloroform, dichloroethane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, nitromethane, nitrobenzene, and a mixed solvent thereof. it can.
  • Examples of the acid used in the reaction include aluminum trichloride, aluminum tribromide, lanthanoid triflate, zeolite, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid, hydrochloric acid, paratoluenesulfonic acid, iron trichloride, zinc dichloride, and polyphosphoric acid. Acids, titanium tetrachloride, titanium tetrabromide, tin chloride, zinc trifluoromethanesulfonate, and the like. The amount of the acid used is in the range of 0.01 to 10 equivalents based on the carboxylic acid chloride (53).
  • the amount of the compound represented by the formula (60) is in the range of 0.5 to 2 equivalents based on the carboxylic acid chloride (53).
  • the reaction temperature is in the range of -20 to 250 ° C, preferably in the range of 10 to 100 ° C.
  • Reaction times range from 10 minutes to 48 hours, preferably from 30 minutes to 16 hours.
  • the compound represented by the formula (6 ′) is a compound of the formula (51) (in the formula (51), X 1 , X 2 , X 3 and X 4 are represented by the formula (1) )) And a compound of the formula (63) (wherein G is the same as in the definition of the formula (6)).
  • 65) in formula (65), Ad is the same as defined in formula (6), and Jb represents an oxygen atom or a sulfur atom).
  • the compound of the formula (64) is produced by reacting the compound of the formula (51) with the compound of the formula (63) in the presence or absence of a base in the presence of a condensing agent.
  • Solvents used in the reaction include, for example, dichloromethane, chloroform, acetonitrile, ethyl acetate, toluene, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like.
  • Examples of the condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide and the like.
  • Examples of the base used in the reaction include 4-dimethylaminopyridine.
  • the amount of the base used is in the range of 0.01 to 1.2 equivalents based on the carboxylic acid (51).
  • the amount of the condensing agent used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51).
  • the amount of the compound represented by the formula (63) is in the range of 1 to 5 equivalents based on the compound represented by the formula (51).
  • the reaction temperature is selected, for example, in the range of 0 to 60 ° C, preferably in the range of 10 to 40 ° C.
  • the reaction time ranges, for example, from 10 minutes to 24 hours, preferably from 30 minutes to 4 hours.
  • the compound of the formula (6 ') can be produced by reacting the compound of the formula (64) with the compound of the formula (65) in the presence of a base.
  • solvent used in the reaction examples include tetrahydrofuran, 1,4-dioxane, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, 1,2-dichloroethane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like. Of mixed solvents.
  • the base used for the reaction includes sodium hydride, n-butyllithium, triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like.
  • the amount of the base to be used is in the range of 1 to 10 equivalents based on the compound of the formula (64).
  • the amount of the compound represented by the formula (65) is in the range of 1 to 5 equivalents based on the compound represented by the formula (64).
  • reaction temperature is, for example, in the range of -78 to 190 ° C, preferably in the range of 10 to 80 ° C.
  • Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.
  • the compound represented by the formula (6 ′) is a compound represented by the formula (64) and a compound represented by the formula (66) (In the formula (66), Ad is the definition in the formula (6)) And Jb represents an oxygen atom or a sulfur atom.).
  • the compound represented by the formula (6 ') can be produced by reacting the compound of the formula (64) with the compound of the formula (66) in the presence of a base.
  • solvent used in the reaction examples include tetrahydrofuran, 1,4-dioxane, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, 1,2-dichloroethane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like. Of mixed solvents.
  • the base used for the reaction includes sodium hydride, n-butyllithium, triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like.
  • the amount of the base to be used is in the range of 0.01 to 10 equivalents based on the compound of the formula (64).
  • the amount of the compound represented by the formula (66) is in the range of 1 to 5 equivalents based on the compound represented by the formula (64).
  • reaction temperature is, for example, in the range of -78 to 190 ° C, preferably in the range of -10 to 80 ° C.
  • Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.
  • the compound represented by the formula (6 ′) is a compound represented by the formula (53) (in the formula (53), X 1 , X 2 , X 3 and X 4 are represented by the formula (1) ))
  • a compound of the formula (67) in the formula (67), G and Ad have the same definitions as in the formula (6), and Jb represents an oxygen atom or a sulfur atom.
  • the compound represented by the formula (6 ') can be produced by reacting the compound of the formula (53) with the compound of the formula (67) in the presence of a base.
  • solvent used in the reaction examples include tetrahydrofuran, 1,4-dioxane, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, 1,2-dichloroethane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like. Of mixed solvents.
  • the base used for the reaction includes sodium hydride, n-butyllithium, triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like.
  • the amount of the base used is in the range of 1 to 10 equivalents based on the compound of the formula (67).
  • the amount of the compound represented by the formula (67) is in the range of 1 to 5 equivalents based on the compound represented by the formula (53).
  • reaction temperature is, for example, in the range of -78 to 190 ° C, preferably in the range of 10 to 80 ° C.
  • Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.
  • n Normal sec: Secondary tert: Tertiary
  • examples of the compound in which A is a group represented by the formula (2A) include X 1 , X 2 , X 3, and X 4 each having a substituent represented by the following Table 10.
  • Table 11 shows specific embodiments of the compound represented by formula (3') among the compounds represented by formula (1).
  • X 1 , X 2 , X 3 and X 4 are a combination of substituents shown in Table 11 below, and Aa is a piperidin-1-yl group, 1-methyl-1-1H-pyrrol-2-yl group, morpholin-4-yl group, indoline-1-yl, benzoisothiazol-3 (2H) -one-1,1-dioxide-2-yl, piperazine -1-yl group, azetidin-1-yl group, 2,5-dioxopyrrolidin-1-yl group, 3-oxoisothiazol-2 (3H) -yl group, benzo [d] isothiazol-2 (3H ) -Yl group, 1,1-dioxo-3-oxobenzo [d] isothiazol-2 (3H) -yl group, 5,6-dihydro-4H-1,3-oxazin-2-yl group, 1
  • X 1 , X 2 , X 3 and X 4 are a combination of substituents shown in Table 12 below, a substituent of Z and its substitution position, Compounds wherein m is a combination shown in Table 13 below.
  • X 1 , X 2 , X 3 , X 4 , Ja and Jb are combinations of the substituents shown in Tables 14 and 15 below
  • Ad is Compounds in which Tables 16 to 17 and G are combinations of the substituents shown in Tables 18 to 19 are included.
  • Plant pathogen The plant pathogen to be controlled by the plant disease controlling agent of the present embodiment is not particularly limited, and includes, for example, fungi, bacteria, actinomycetes, viruses, and the like, particularly in oomycetes and soil. Fungi that inhabit the sea.
  • phytopathogenic fungi examples include, for example, Pythium ⁇ ultimum, vegetable wilt fungus (Rhizoctonia solani), Chinese cabbage rot fungus (Rhizoctonia solani), cucumber vine rot fungus (Fusarium umyos) Fusarium oxysporum, lettuce root rot fungus (Fusarium oxysporum), cucurbit homopsis root rot fungus (Phomopsis scleroticoides), cruciferous vegetable root rot fungus (Plasmodiosapora spore spore spore spore spore spore spore spore spore spore fungus) Purple crested wilt fungus (Helicobasidum @ mompa), fruit tree white crested feather Fungus (Rosellinia necatrix), soybean wilt fungus (Sclerotium rollsii), tomato brown root rot (Pyrenochae
  • phytopathogenic fungi include potato blight fungus (Phytophthora infestans), cucumber downy mildew (Pseudoperonospora cubensis), grape downy mildew (Plasmopara viticola), cucumber gray blight fungus (Phycium phytoa phyto phytoa phytoa phyto phyto phyto phyto phyto phyto phyto phyto phytophyto) and a phytophytic phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyt
  • phytopathogenic fungi include, for example, Pythium ultimum, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, and Curcuma wilt fungus (Rhizoctonia solani).
  • phytopathogenic bacteria examples include, for example, Pseudomonas, Erwinia, Pectobacterium, Xanthomonas, Burkholderia, Streptomyces, Ralstonia, Clavibacter, Cirbacter, Chibibacil, Cirobacterium, and Genus Rhizomonas , Acidovorax, Arthrobacter, and Rhodococcus.
  • Preferred examples of the phytopathogenic bacteria include the genus Pseudomonas, the genus Agrobacterium, the genus Ralstonia, and the genus Erwinia.
  • the phytopathogenic actinomycetes include Streptomyces genus.
  • wheat-dwarf virus Soil-born @ heat @ mosaic @ virus
  • soybean mosaic virus Soybean @ mosaic @ virus
  • alfalfa mosaic virus Alfalfa @ mosaic @ virus
  • potato leaf curl virus Pautrovirus
  • Mosaic virus Cluster mosaic virus
  • tobacco mosaic virus Tobacco mosaic virus
  • the plant disease control agent of this embodiment contains the compound represented by the formula (1) as an active ingredient.
  • "containing the compound represented by the formula (1) as an active ingredient” means that the compound represented by the formula (1) is contained in such an amount that a plant disease controlling effect can be obtained.
  • the content of the compound represented by formula (1) is not particularly limited as long as it contains the compound represented by the formula (1) in the form of a free form, a hydrate, an optional solvate, a salt or the like as an active ingredient.
  • the above-mentioned compound may be used as it is, or may be used in accordance with a conventional method of agricultural and horticultural disease controlling agent.
  • Horticulturally acceptable carriers for example, solid carriers, liquid carriers, gaseous carriers, surfactants, mixed with dispersants, emulsions, solutions, suspensions, wettable powders, powders, granules, tablets, It may be used in the form of a composition (formulation) for controlling plant diseases in any dosage form such as oils, aerosols, flowables and the like.
  • the composition for controlling plant diseases may further contain other pharmaceutical auxiliaries.
  • ⁇ ⁇ Usable carriers include liquid carriers, solid carriers, gaseous carriers, surfactants, dispersants and the like.
  • examples of the auxiliary agent for formulation include those usually used in a composition for controlling plant diseases.
  • solid carrier examples include clays (carion clay, diatomaceous earth, bentonite, acid clay, etc.), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (selinite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc.) ) And synthetic polymers such as starch, lactose, vinyl chloride polymers, and polyurethane.
  • liquid carrier examples include alcohols (methanol, ethanol, isopropanol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, glycerin, etc.), ketones (acetone, methyl ethyl ketone, etc.), and aromatic hydrocarbons (benzyl, etc.).
  • alcohols methanol, ethanol, isopropanol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, glycerin, etc.
  • ketones acetone, methyl ethyl ketone, etc.
  • aromatic hydrocarbons benzyl, etc.
  • gaseous carrier LPG, air, nitrogen, carbon dioxide, dimethyl ether and the like can be mentioned.
  • surfactants and dispersants for emulsification, dispersion, spreading, and the like include alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, and lignin. Sulfonates and the like are used. Further, auxiliaries for improving the properties of the preparation include, for example, carboxymethylcellulose, gum arabic, polyethylene glycol, calcium stearate and the like.
  • the above carriers, surfactants, dispersants, and auxiliaries can be used alone or in combination as necessary.
  • the content of the plant disease controlling agent (the compound represented by the formula (1)) in the plant disease controlling composition is not particularly limited. 1 to 50% by mass, usually 1 to 50% by mass for wettable powders, usually 0.1 to 30% by mass for powders, usually 0.1 to 15% by mass for granules, and usually 0.1 to 10% by mass for oils For aerosols, the content is usually 0.1 to 10% by mass.
  • the plant disease controlling agent or the plant disease controlling composition of the present embodiment may be used as it is, or may be used after being diluted as necessary.
  • the plant disease controlling agent or the composition for controlling a plant disease can be used together with other pest controlling agents.
  • a resistance inducer and another pest controlling agent may be mixed and sprayed, or separately. May be sprayed at different times or simultaneously.
  • pesticides include, for example, insecticides, fungicides, acaricides, herbicides, plant growth regulators, fertilizers, and the like.
  • Pesticide Manual 17th edition "British Crop Protection” issued by Shibuya INDEX, 17th edition, 2014, SHIBYA INDEX RESEARCH issued by GROUP.
  • insecticide examples include acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, prophenofrosyl, prophenofrosyl, profenofosyl, profenofosyl, profenofosyl, and fenofosyl.
  • fungicide examples include azoxystrobin, kresoxim-methyl, trifloxystrobin, orysastrobin, picoxystrobin, and fluoxastrobin. ), Etc .; ananilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil, etc .; triadimefon, bitertanol, flitumisol, triflumethanol, triflumethanol, triflumethanol, triflumitolol michole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole, tecoconazole, tecoconazole, tebuconazole, tebuconazole, tebuconazole, tebuconazole Azole compounds such as (simeconazole); quinoxaline compounds such as quinomethionate; maneb, zineb, mancozeb, poly
  • Organotin compounds such as fludioxonil and fenpiclonil; others, fthalide, probenazole, acibenzolar S-methyl (cibenzollar-S-methyl), thiadinyl, thiadinil.
  • Examples of the acaricide include bromopropylate, tetradifon, propargite, amitraz, fenothiocarb, hexothiazoxen, hexithiazoxin, hexithiazoxin, hexithiazoxin, hexithiazoxin, and hexithiazoxin.
  • herbicides examples include phenoxy acid-based compounds such as cyhalofop-butyl and 2,4-D (2,4-dichlorophenoxyacetic acid); esprocarb, desmedifam; Carbamate compounds such as alachlor, metolachlor and the like; acid amide compounds such as diachlor and metolachlor; urea compounds such as diuron and tebuthiuron; halosulfuron-methyl, frazas Sulfonylurea-based compounds such as flurasulfuron; pyrimidyloxybenzoic acid-based compounds such as pyriminobac-methyl Compounds: Amino acid compounds such as glyphosate, bialaphos, glufosinate-ammonium and the like.
  • the plant growth regulator examples include an ethylene agent such as ethephon; an auxin agent such as indolebutyric acid, ethiclozate; a cytokinin agent; a gibberellin agent; an auxin antagonist; a dwarfant; And the like.
  • fertilizer examples include nitrogenous fertilizers such as urea, ammonium nitrate, ammonium nitrate, and ammonium chloride; phosphate fertilizers such as lime superphosphate, ammonium phosphate, magnesia perphosphoric acid, and magnesium phosphate; Potassium fertilizers such as potassium chloride, potassium bicarbonate, potassium nitrate, potassium nitrate and potassium sodium nitrate; manganese fertilizers such as manganese sulfate and manganese nitrate; boronaceous fertilizers such as boric acid and borate; Can be
  • the present invention provides a method for controlling a plant disease, which comprises bringing the above-mentioned plant disease controlling agent or the above-mentioned compound into contact with a plant or a seed or containing the compound in a cultivation bed.
  • the plant disease controlling agent may be used in the form of the plant disease controlling composition described above.
  • the above-mentioned plant disease controlling agent When the above-mentioned plant disease controlling agent is brought into contact with a plant, it may be brought into contact with the foliage, root, rhizome, tuber, bulb, germinated bud and the like of the plant.
  • the above-mentioned plant disease controlling agent may be brought into contact with plant seeds.
  • Examples of the cultivation floor include soil, paddy water for growing rice, carriers for growing plants, water for hydroponics, and the like. Hydroponic water may contain nutrients.
  • the method of contacting the above-mentioned plant disease controlling agent with a plant body or a seed, or the method of containing it in a cultivation bed is not particularly limited as long as it is an application method generally applied in agriculture and horticulture.
  • foliage application, water surface application, soil treatment, seedling box application, seed treatment, immersion treatment, fertilizer mixing, irrigation water mixing, and the like can be mentioned.
  • the application rate of the plant disease controlling agent of the present embodiment in addition to the application method, in consideration of the application mode such as aerial spraying and ultra-trace spraying, depending on the type and severity of the target disease, the type of the target crop and the target site. , Can be determined.
  • a solution prepared by diluting 1 to 1000 g of the formulation with 50 to 1000 L of water per 10 ares in the form of an emulsion, wettable powder or flowable agent is used.
  • wettable powder or flowable agent is used in the form of powder.
  • about 1 to 10 kg of the preparation can be used per 10 ares.
  • Example 1 2,3,6-Trifluoroisonicotinic acid (1.76 g) was dissolved in N, N-dimethylformamide (10 mL), and bromoethane (1.08 g) and potassium carbonate (1.38 g) were added to the solution. In addition, the mixture was stirred at 80 ° C. for 2 hours. Next, the reaction mixture was returned to room temperature, ethyl acetate was added, and the mixture was extracted with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography to obtain the compound of Example 1-117 (yield 1.44 g).
  • Example 2 2,3,6-Trifluoroisonicotinic acid (5.28 g) was dissolved in thionyl chloride (30 mL) and heated under reflux for 1 hour. After concentrating this reaction product, it was dissolved in acetonitrile (30 mL), 3-chloro-4-methylaniline (5.64 g) and pyridine (3.20 g) were added, and the mixture was heated under reflux for 1 hour. Next, the reaction mixture was returned to room temperature, ethyl acetate was added, and the mixture was washed with 1N hydrochloric acid and 1N sodium hydroxide in that order. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography to give the compound of Example 1-30 (yield 7.70 g).
  • Example 3 Dissolve 2,3,6-trifluoro-4-pyridinemethanol (106 mg) in dichloromethane (8 mL), add acetyl chloride (65 mg) to the solution, cool to 0 ° C., and add N, N-diisopropyl Ethylamine (130 mg) was added, and the mixture was stirred at room temperature overnight. Next, after the solvent was distilled off, the residue was dissolved in diethyl ether, washed sequentially with saturated sodium carbonate, 2% hydrochloric acid and saturated saline, and the organic layer was dried over anhydrous magnesium sulfate. After evaporating the solvent with an evaporator, the residue was purified by silica gel chromatography to obtain the compound of Example 3-1 (yield 63.2 mg).
  • Example 4 2,6-Difluoroisonicotinic acid (50 mg) was dissolved in chloroform (3.1 mL), and aniline (29 ⁇ L) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (65 mg) were added to the solution. ) And 4-dimethylaminopyridine (catalytic amount) were added, and the mixture was stirred at room temperature for 3 hours. Next, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated ammonium chloride and saturated sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography to give the compound of Example 1-143 (yield 66.3 mg).
  • Example 5 2,3,6-Trifluoroisonicotinic acid (30 mg) was dissolved in chloroform (3.1 mL), and ethylenediamine (6.0 ⁇ L) and 1-ethyl-3- (3-dimethylaminopropyl) were added to the solution.
  • Carbodiimide hydrochloride (38 mg), 1-hydroxybenzotriazole (27 mg), and triethylamine (30 ⁇ L) were added, and the mixture was stirred at room temperature overnight.
  • 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (38 mg) and 1-hydroxybenzotriazole (27 mg) were added, and the mixture was stirred at room temperature for 3 hours.
  • Example 6 2,3,6-Trifluoroisonicotinic acid (100 mg) was dissolved in N, N-dimethylformamide (5.6 mL), and 2-chloroethylamine hydrochloride (79 mg) and 1-ethyl-3- (3-dimethyl (Aminopropyl) carbodiimide hydrochloride (128 mg), 1-hydroxybenzotriazole (92 mg), and triethylamine (101 ⁇ L) were added, and the mixture was stirred at room temperature for 3 hours. Next, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated ammonium chloride and saturated sodium hydrogen carbonate.
  • Example 7 2,6-Difluoroisonicotinic acid (80 mg) is dissolved in acetonitrile (1 mL), and cyclohexyl alcohol (50 mg) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (96 mg) are dissolved in the solution. And 4-dimethylaminopyridine (61 mg) were added, and the mixture was stirred at room temperature for 24 hours. Next, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by Preparative TLC to give the compound of Example 1-205 (yield 42 mg).
  • Example 8 2,3,6-Trifluoroisonicotinic acid (177 mg, 1.0 mmol) was dissolved in dichloroethane, thionyl chloride (1 mL) was added to the solution, and the mixture was heated under reflux and stirred for 2 hours. After evaporating the solvent of the reaction product with an evaporator, nitromethane (3 mL), 1-methylpyrrole (54 mg, 0.67 mmol), and zinc (II) trifluoromethanesulfonate (24 mg, 0.066 mmol) were added, and the mixture was added at room temperature. Stirred overnight. After sodium hydrogen carbonate was added to the reaction mixture, water was added, and the mixture was extracted with chloroform.
  • Table 46 shows the compounds of Examples 2-1 to 2-5 represented by the formula (3 ').
  • Table 47 shows the compounds of Example 3-1 and Example 3-2 represented by the formula (4 '').
  • Table 48 shows compounds of Examples 4-1 to 4-4 represented by the formula (5 '').
  • Table 49 shows compounds of Examples 5-1 to 5-9 represented by the formula (6 '').
  • Example 9 Activity against cucumber downy mildew> Acetone solution of the following example compound prepared to be 0.4 mg / mL was diluted 10-fold with water and used for the test. To the root of the cucumber (variety: four leaves) at the first leaf stage cultivated in the pot, 5 mL of the diluted solution per pot was drenched in soil. Seven days after the treatment, a spore suspension of cucumber downy mildew (Pseudoperonospora cubensis: oomycetes) adjusted to 5 ⁇ 10 4 cells / mL was sprayed and inoculated, and the humid chamber (temperature 25 ° C., humidity 100%) was sprayed for 24 hours. It was left still.
  • the lesion area ratio of the second leaf was examined according to the following index.
  • the disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
  • the following example compounds exhibited a control value of 70 or more, and the control effect against cucumber downy mildew was confirmed.
  • Example 10 ⁇ Activity against cucumber downy mildew> An acetone solution of the following example compound prepared so as to have a concentration of 1 mg / mL was diluted 10-fold with water and subjected to a test. 1 mL of the diluent per pot was sprayed on each cucumber (variety: four leaves) at the first leaf stage cultivated in the pot. Seven days after spraying, a spore suspension of cucumber downy mildew (Pseudoperonospora cubensis: oomycetes) adjusted to 5 ⁇ 10 4 cells / mL was sprayed and inoculated, and the humid chamber (temperature 25 ° C., humidity 100%) was sprayed for 24 hours. It was left still.
  • Example 11 Activity against tomato blight> Acetone solutions prepared at 1 mg / mL for Example Compounds 1-135 and 1-168 were diluted 10-fold with water and used for the test.
  • the cells were cultivated in a greenhouse, and after 4 days from the inoculation, after spraying, the lesion area ratio of the developed leaves was examined according to the following index.
  • the disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
  • the following example compounds showed a control value of 50 or more, and the control effect against tomato late blight was confirmed. 1-135, 1-168
  • Example 12 ⁇ Activity against grape downy mildew>
  • a wettable powder was prepared according to Formulation Example 1, and then diluted 1000-fold with water to prepare a spray liquid.
  • the test was performed in a field where grape downy mildew occurs naturally.
  • the prepared spray liquid was sprayed twice at the flowering stage grape (variety: Koshu) at a liquid volume of 1 L / tree.
  • the prepared spray liquid was sprayed at a rate of 2 L / tree.
  • Leaf lesions were examined according to the following index. The disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
  • Example compounds 1-135 and 1-168 exhibited a control value of 65 or more, and the control effect against downy mildew was confirmed.
  • Example 13 ⁇ Activity against Makwauri vine disease> An acetone solution of the following example compound prepared to be 0.5 mg / mL was diluted 10-fold with water and used for the test. 3 mL per pot of soil was drenched at the root of the cotyledon-stage makuwauri (cultivar: golden mallow) cultivated in the pot. The day after the treatment, a suspension of yeast-like cells (bud cell) of Fusarium oxysporum f. Sp melonis adjusted to 5 ⁇ 10 7 cells / mL was instilled and inoculated. Then, it was cultivated in a greenhouse, and examined 28 days after inoculation according to the following index.
  • the disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
  • Exponent (0-2) 0: No lesion 1: Yellowing of true leaves or stem 2: Death Severity ((2 ⁇ number of individuals with index 2) + (1 ⁇ number of individuals with index 1)) / number of individuals surveyed / 2 ⁇ 100
  • Control value ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100
  • the following example compounds showed a control value of 60 or more, and the control effect against the scab disease of Makwauri was confirmed. 1-30, 1-41, 1-98, 1-126, 1-134, 1-135, 1-139, 1-143, 1-218, 3-1, 3-2, 4-2, 4- 4
  • Example 14 ⁇ Activity against Makwauri vine disease> An acetone solution of the following example compound prepared to be 0.25 mg / mL was diluted 10-fold with water and used for the test. 3 mL per pot of soil was drenched at the base of the 1-leaf stage makuwauri (cultivar: golden mushroom) cultivated in the pot. Seven days after the treatment, the plants were planted in a mixed soil (mass ratio 1: 9) of a culture of Fusarium oxysporum f.sp melonis and a cultivated soil. Thereafter, the plants were cultivated in a greenhouse, and examined 28 days after planting according to the following index.
  • the disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
  • Exponent (0-2) 0: No lesion 1: Yellowing of true leaves or stem 2: Death Severity ((2 ⁇ number of individuals with index 2) + (1 ⁇ number of individuals with index 1)) / number of individuals surveyed / 2 ⁇ 100
  • Control value ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100
  • the following example compounds showed a control value of 60 or more, and the control effect against the scab disease of Makwauri was confirmed.
  • Example 15 ⁇ Activity against Makwauri vine disease> An acetone solution of the following example compound prepared so as to have a concentration of 0.15 mg / mL was diluted 10-fold with water and subjected to a test. 0.5 mL was sprayed on the first true leaf of the 1-leaf stage makuwauri (cultivar: Golden Makowari) cultivated in a pot. Seven days after the treatment, the plants were planted in a mixed soil (mass ratio 1: 9) of a culture of Fusarium oxysporum f.sp melonis and a cultivated soil. Thereafter, the plants were cultivated in a greenhouse, and examined 28 days after planting according to the following index.
  • a mixed soil mass ratio 1: 9
  • the disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
  • Exponent (0-2) 0: No lesion 1: Yellowing of true leaves or stems 2: Withering Degree of disease ((2 ⁇ number of individuals with index 2) + (1 ⁇ number of individuals with index 1)) / number of individuals surveyed / 2 ⁇ 100
  • Control value ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100
  • Example 16 Activity against cucumber seedling blight> An acetone solution of the following example compound prepared to be 0.5 mg / mL was diluted 10-fold with water and used for the test. At the root of the cucumber (variety: four leaves) at the cotyledon stage cultivated in the pot, 3 mL per pot was subjected to soil irrigation. One day after the treatment, the plants were planted in a mixed soil (mass ratio 1: 9) of a culture of a cucumber seedling blight fungus (Pythium ultimum var. Ultimum) and a culture medium. After that, the plants were cultivated in a greenhouse, and 15 days after planting, they were examined according to the following index.
  • a mixed soil mass ratio 1: 9
  • the disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
  • Example 17 Activity against Chinese cabbage butt rot> An acetone solution of the following example compound prepared to be 0.5 mg / mL was diluted 10-fold with water and used for the test. 3 mL per pot of the Chinese cabbage (cultivar: Muso) was irrigated with soil at the base of the three-leaf Chinese cabbage cultivated in the pot. Seven days after the treatment, the plants were planted in a mixed soil (a mass ratio of 1: 9) of a culture of a Chinese cabbage rot fungus (Rhizoctonia solani) and a culture soil. After that, the plants were cultivated in a greenhouse, and 15 days after planting, they were examined according to the following index.
  • the disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
  • the following example compounds exhibited a control value of 50 or more, and the control effect on Chinese cabbage bottom rot was confirmed. 1-30, 1-41, 1-117, 1-189, 1-193, 1-197
  • Example 18 Activity against lettuce root rot> A wettable powder of Example Compound 1-199 was prepared according to Formulation Example 1. This wettable powder was diluted 5,000-fold with water, and 2 L of the lettuce (cultivar: Raptor) 20 days after sowing cultivated in a 220-well paper pot was irrigated and planted in a field where lettuce root rot was naturally occurring the next day. 44 days after planting, the plant was examined according to the following index to calculate the disease severity. The control value was calculated from the obtained degree of disease by the following formula. Exponent (0-3) 0: No browning 1: Partial vascular browning 2: Browning extends around crown 3: Heavy browning or cavitation of crown, or dead (due to death of entire strain).
  • Example compound 1-199 showed a control value of 50 or more, and its control effect on lettuce root rot was confirmed.
  • Example 19 Activity against cucumber homopsis root rot>
  • the potato sucrose liquid medium was inoculated with Phomopsis sclerotioides and cultured at 25 ° C. for 4 weeks.
  • the obtained bacterial flora was ground by Hiscotron (Nichion Medical Science Instrument Co., Ltd.) to obtain a ground liquid.
  • the obtained trituration liquid was mixed with soil, and this was used as homopsis-contaminated soil.
  • An acetone solution of Example Compound 1-199 was prepared to be 1 mg / mL. This was diluted 10-fold with water, and 1/5000 volume of neoesterin was added to obtain a spray solution.
  • the cucumber was transplanted to homopsis-contaminated soil, cultivated in a greenhouse for 4 weeks, and then measured for plant height.
  • the plant height of the cucumber cultivated without transplanting to the homopsis-contaminated soil was 100
  • the plant height of the untreated cucumber was 66.
  • the plant height of the cucumber treated with the example compound 1-199 was 97, indicating that the control effect of the example compound 1-199 against cucumber homopsis root rot was confirmed.
  • Example 20 The potato sucrose liquid medium was inoculated with Phomopsis sclerotioides and cultured at 25 ° C. for 4 weeks.
  • the obtained bacterial flora was ground by Hiscotron (Nichion Medical Science Instrument Co., Ltd.) to obtain a ground liquid.
  • the obtained trituration liquid was mixed with soil, and this was used as homopsis-contaminated soil.
  • An acetone solution of Example Compound 1-199 was prepared to be 1 mg / mL. This was diluted 50-fold with water to obtain an irrigation solution.
  • a cucumber (variety: four leaves) at the cotyledon stage one week after sowing cultivated in the pot was irrigated with 5 mL of an irrigation solution per pot into the soil.
  • Example Compound 1-199 was 94, thus confirming the controlling effect of Example Compound 1-199 on the root rot of cucumber homopsis.
  • Example 21 Provides ⁇ Proliferation inhibitory activity against pathogenic fungi of soil disease> The following example compounds were dissolved in DMSO to a concentration of 12.8 mg / mL. Cucumber seedling wilt fungus (Pythium ultimum), Chinese cabbage rot fungus (Rhizoctonia solani), Makwauri vine wilt fungus (Fusarium oxysporum), and homopsis root rot fungus (Phosmodios thrombosis sci.) (Kikki Seisakusho) and diluted 50 to 100 times with a potato sucrose medium to obtain a bacterial solution.
  • DMSO DMSO
  • Example 22 The following example compounds were dissolved in DMSO to a concentration of 12.8 mg / mL. Cucumber seedling wilt fungus (Pythium ultimum) cultured in a potato sucrose liquid medium was ground with a Hiscotron (Nichion Medical Science Instruments) and diluted 50 to 100 times with a potato sucrose medium to obtain a bacterial solution. 200 ⁇ L of the bacterial solution was added to 1 ⁇ L of the DMSO solution of the example compound, and the mixture was cultured at 25 ° C. for 3 days. Then, the presence or absence of inhibition of hyphal elongation was visually determined.
  • Cucumber seedling wilt fungus (Pythium ultimum) cultured in a potato sucrose liquid medium was ground with a Hiscotron (Nichion Medical Science Instruments) and diluted 50 to 100 times with a potato sucrose medium to obtain a bacterial solution. 200 ⁇ L of the bacterial solution was added to 1 ⁇ L of
  • Example 23 ⁇ Proliferation inhibitory activity against oomycetes>
  • the following example compounds were dissolved in DMSO to a concentration of 12.8 mg / mL.
  • Cucumber gray blight (Phytophthora capsici) cultured in a potato sucrose liquid medium was ground with a Hiscotron (Nichion Medical Science Instrument Co., Ltd.) and diluted 50 to 100 times with a potato sucrose medium to obtain a bacterial solution. 200 ⁇ L of the bacterial solution was added to 1 ⁇ L of the DMSO solution of the example compound, and the mixture was cultured at 25 ° C. for 3 days. Then, the presence or absence of inhibition of hyphal elongation was visually determined.
  • Formulation Example 1 10 parts by mass of the compound of the example, 2 parts by mass of lauryl sulfate, 2 parts by mass of polyoxyethylene alkyl ether, 3 parts by mass of ligninsulfonate, 4 parts by mass of white carbon, and 79 parts by mass of clay were mixed and pulverized to obtain a wettable powder. I got
  • the plant disease controlling agent of the present invention has excellent resistance inducing activity and is useful for controlling plant diseases (especially diseases caused by oomycetes and soil diseases).

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  • 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)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne un agent de lutte contre les maladies végétales et un procédé de lutte contre les maladies végatales, l'agent de lutte contre les maladies végétales contenant un composé représenté par la formule (1) en tant qu'ingrédient actif. (Dans la formule, X1 et X4 représentent chacun indépendamment un atome de fluor ou analogues, X2 et X3 représentent chacun indépendamment un atome d'hydrogène ou un atome de fluor, Xa est un groupe représenté par la formule (2), (3), (4), (5) ou (6), J représente un atome d'oxygène ou analogues, Q représente un atome d'oxygène ou analogues, A représente un groupe phényle ou analogues qui peut avoir un substituant, Aa représente un groupe pipéridin-1-yle ou analogues, Qb représente un atome d'oxygène ou analogues, Ab représente un atome d'hydrogène ou analogues, Z représente un atome d'hydrogène ou analogues, m représente un nombre entier d'1 à 3, Ja et Jb représentent chacun indépendamment un atome d'oxygène ou analogues, G représente un groupe phényle ou analogues, et Ad représente un groupe alkyle, un groupe alkyloxy, ou analogues.)
PCT/JP2019/034715 2018-09-06 2019-09-04 Agent de lutte contre les maladies végétales Ceased WO2020050297A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP2018166473A JP2021185128A (ja) 2018-09-06 2018-09-06 土壌病害防除剤
JP2018-166473 2018-09-06
JP2018-171046 2018-09-13
JP2018171046A JP2021185129A (ja) 2018-09-13 2018-09-13 植物保護剤
JP2019139210A JP2021185130A (ja) 2019-07-29 2019-07-29 土壌病害防除剤
JP2019-139210 2019-07-29

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115215795A (zh) * 2021-04-21 2022-10-21 帕潘纳(北京)科技有限公司 一种氟啶虫酰胺的合成方法
WO2023189782A1 (fr) * 2022-03-28 2023-10-05 株式会社Mmag Composition de lutte contre les maladies des plantes, préparation et procédé de lutte contre les maladies des plantes
US12156523B2 (en) * 2017-03-17 2024-12-03 Mmag Co., Ltd. Plant disease control agent

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JPH01283270A (ja) * 1988-03-25 1989-11-14 Ciba Geigy Ag 植物を病気から保護するための組成物
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WO2018169038A1 (fr) * 2017-03-17 2018-09-20 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Agent de lutte contre les maladies des plantes
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JPS6393766A (ja) * 1986-09-26 1988-04-25 チバーガイギー　アクチエンゲゼルシヤフト 病気から植物を保護する方法及び薬剤
JPH01272569A (ja) * 1988-03-09 1989-10-31 Ciba Geigy Ag 病気に対して植物を保護するための組成物
JPH01283270A (ja) * 1988-03-25 1989-11-14 Ciba Geigy Ag 植物を病気から保護するための組成物
JPH05286970A (ja) * 1992-04-07 1993-11-02 Ube Ind Ltd ２−アシルアミノ−２−チアゾリン化合物、その製法及び有害生物防除剤
JPH08176112A (ja) * 1994-12-22 1996-07-09 Mitsui Toatsu Chem Inc Ｎ，ｎ−ジ置換アニリン誘導体およびこれを有効成分とする農園芸用殺菌剤
JP2004519464A (ja) * 2001-01-25 2004-07-02 シンジエンタ パーテイスィペイシヨンズ アクチエンゲゼルシヤフト 農業における殺菌剤としてのカルボキサミド
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WO2009011305A1 (fr) * 2007-07-13 2009-01-22 Sumitomo Chemical Company, Limited Composé amide et procédé de lutte contre des maladies des plantes à l'aide de ce composé
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WO2014124988A1 (fr) * 2013-02-15 2014-08-21 Syngenta Limited Dérivés de pyridine et leur utilisation en tant qu'herbicides
WO2016066636A1 (fr) * 2014-10-29 2016-05-06 Bayer Cropscience Aktiengesellschaft N-(2-halogéno-2-phénéthyl)carboxamides en tant que fongicides
WO2018169038A1 (fr) * 2017-03-17 2018-09-20 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Agent de lutte contre les maladies des plantes
WO2019168112A1 (fr) * 2018-02-28 2019-09-06 北興化学工業株式会社 Dérivé imide et bactéricide le contenant en tant que principe actif

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12156523B2 (en) * 2017-03-17 2024-12-03 Mmag Co., Ltd. Plant disease control agent
CN115215795A (zh) * 2021-04-21 2022-10-21 帕潘纳(北京)科技有限公司 一种氟啶虫酰胺的合成方法
CN115215795B (zh) * 2021-04-21 2023-07-25 帕潘纳(北京)科技有限公司 一种氟啶虫酰胺的合成方法
WO2023189782A1 (fr) * 2022-03-28 2023-10-05 株式会社Mmag Composition de lutte contre les maladies des plantes, préparation et procédé de lutte contre les maladies des plantes

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