WO2018124088A1 - Composé amide substitué par l'alkylphényle et agent de lutte antiparasitaire - Google Patents

Composé amide substitué par l'alkylphényle et agent de lutte antiparasitaire Download PDF

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WO2018124088A1
WO2018124088A1 PCT/JP2017/046693 JP2017046693W WO2018124088A1 WO 2018124088 A1 WO2018124088 A1 WO 2018124088A1 JP 2017046693 W JP2017046693 W JP 2017046693W WO 2018124088 A1 WO2018124088 A1 WO 2018124088A1
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atom
alkyl
hydrogen atom
methyl
substituted
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PCT/JP2017/046693
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English (en)
Japanese (ja)
Inventor
三田　猛志
佑樹 田島
豊 吉永
基悦 岩佐
佑介 南條
美穂 旭
国光 中平
優樹 植村
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日産化学工業株式会社
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Priority claimed from JP2017134111A external-priority patent/JP2020029402A/ja
Application filed by 日産化学工業株式会社 filed Critical 日産化学工業株式会社
Publication of WO2018124088A1 publication Critical patent/WO2018124088A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
    • A—HUMAN NECESSITIES
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    • 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
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a novel alkynylphenyl-substituted amide compound and a salt thereof, and a pest control agent containing the compound as an active ingredient.
  • alkynylphenyl-substituted amide compounds for example, (E) -N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -2-methoxyimino-1-methylethyl] -2- ( (Trifluoromethyl) benzamide, (E) -N- [2- [2-chloro-4- (1-propynyl) phenyl] -2-methoxyimino-1-methylethyl] -3- (trifluoromethyl) pyridine- 2-carboxamide, (E) -N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -2-methoxyimino-1-methylethyl] -2- (difluoromethyl) nicotinamide, (E ) -N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -2
  • N- [2- [4- (4-ethoxyphenylethynyl) phenyl] -1-methylethyl] benzamide and the like have acetyl CoA carboxylase inhibitory activity (see Patent Document 6), (R) -3- [4- (cyclopropylethynyl) -3-fluorophenyl] -2- (2-fluoro-4-methylbenzamido) propionic acid or the like has a GLP-1 receptor modulating action (see Patent Document 7).
  • Patent Document 9 It has liptophan hydroxylase inhibitory activity (see Patent Document 9) and 1- [5- [2- (5-chloro-2-methoxybenzamido) ethyl] -2-ethynylbenzenesulfonyl] -3-methylthiourea, etc. Has a KATP channel blocker activity (see Non-Patent Document 1).
  • JP 2016-011286 A Japanese Patent Laying-Open No. 2015-214536 JP 2005-179234 A International Publication No. 2006-016708 JP 2007-210924 A International Publication No. 2012-028676 International Publication No. 2011-097300 International Publication No. 2007-141473 International Publication No. 2016-109501 International Publication No. 2005-107762 International Publication No. 2007-131864 International Publication No. 2016-145258
  • Infections and infestations of pests such as pathogens and parasites can occur when the host is a plant such as cereals, fruit trees, vegetables, ornamental plants, etc. Cause serious economic losses not only to producers but also to consumers. Therefore, effective control of these pests is a very important issue in order to achieve efficient and stable crop production.
  • the host is an animal such as a companion animal, pet animal, livestock, poultry, etc., for the purpose of maintaining the health of the target animal, and when the target animal is livestock, poultry, etc. Effective control of these pests is also an important issue for the purpose of stably producing safe food and high-quality living materials such as wool, feathers and leather.
  • the present inventors have found that the novel alkynylphenyl-substituted amide compound represented by the following formula (I) has excellent pest control activity, particularly antifungal / nematicidal
  • the present invention has been completed by finding an extremely useful compound that exhibits insect activity and has almost no adverse effect on non-target organisms such as plants, mammals, fish, useful insects and natural enemies. That is, the present invention relates to the following [1] to [76].
  • G 1 represents a structure represented by G 1 -1 ⁇ G 1 -9,
  • X 1 represents a halogen atom, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1- represents C 3 alkylsulfinyl, C 1 ⁇ C 3 alkylsulfonyl, C 1 ⁇ C 3 haloalkylthio or C 1 ⁇ C 3 haloalkylsulfonyl, X 2 represents a hydrogen atom or a halogen atom, Y 1 represents a hydrogen atom, a halogen atom, nitro, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy or C 1 -C 3 alkylthio, Y 2 represents a hydrogen atom, a halogen
  • R 3 represents a hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl
  • R 4 represents a hydrogen atom or C 1 -C 6 alkyl
  • R 3 and R 4 together form an ethylene chain to form a cyclopropyl ring with the carbon atom to which R 3 and R 4 are bonded
  • R 5 is a hydrogen atom, C 1 ⁇ C 4 alkyl, C 1 ⁇ C 4 haloalkyl, substituted by R 7 (C 1 ⁇ C 2 ) alkyl, C 3 ⁇ C 6 cycloalkyl, C 2 ⁇ C 4 alkenyl C 3 -C 4 alkynyl, —OH, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, —C (O) R 8 or C 1 -C 4 alkoxycarbonyl Represent
  • R 6 is a hydrogen atom
  • D-1 to D-53 each represent an aromatic heterocycle represented by the following structural formula
  • Z is a halogen atom, cyano, nitro, —SF 5 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyano (C 1 -C 4 ) alkyl, C 1 -C 4 alkoxy (C 1 -C 4 ) Alkyl, C 1 -C 4 haloalkoxy (C 1 -C 4 ) alkyl, C 1 -C 4 alkylthio (C 1 -C 4 ) alkyl, C 1 -C 4 alkylsulfinyl (C 1 -C 4 ) alkyl, C 1 -C 4 alkylsulfonyl (C 1 -C 4 ) alkyl, C 1 -C 4 haloalkylthio (C 1 -C 4 ) alkyl, C 1 -C 4 haloalkylsulfinyl (C 1 -C 4 ) alkyl, C 1 -C 4
  • the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, cyano, C 1.
  • a halogen atom cyano
  • C 1 -C 4 haloalkyl optionally substituted by -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 haloalkylthio,
  • D-54 to D-62 each represent an aromatic heterocycle represented by the following structural formula
  • Z a represents a halogen atom, cyano, C 1 -C 4 alkyl, C 1 -C 2 haloalkyl, C 3 -C 4 cycloalkyl, methoxy, methylthio, trifluoromethylthio or trifluoromethylsulfonyl, and n1 is 2 or more
  • Z a may be the same as or different from each other
  • Z b represents a halogen atom, methyl, trifluoromethyl or methoxy
  • each Z b may be the same as or different from each other
  • R 7 is cyano, C 3 -C 6 cycloalkyl, —OR 13 , C 1 -C 4 alkylthio, C 1 -C 4 alkoxycarbonyl, —C (O) NH 2 , —C (S) NH 2 , phenyl , (Z) represents phenyl substituted by m or D-23
  • R 8 represents C 1
  • E-1 and E-2 each represent a saturated heterocyclic ring represented by the following structural formula
  • R 15 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy (C 1 -C 2 ) alkyl, C 3 -C 4 alkenyl, C 3 -C 4 haloalkenyl, C 3 -C 4 alkynyl, C 3 -C 4 haloalkynyl, phenyl or phenyl substituted by (Z) m
  • R 16 and R 17 are each independently a hydrogen atom, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy (C 1 -C 2 ) alkyl, C 3 -C 4 alkenyl, Represents C 3 -C 4 alkynyl, phenyl or phenyl substituted by (Z) m
  • R 16 and R 17 may form
  • R 18 represents C 1 -C 4 alkyl, and when p represents 2, each R 18 may be the same as or different from each other; m represents 1, 2, 3, 4 or 5; n represents 0, 1, 2, 3 or 4; n1 represents 0, 1, 2, 3 or 4; n2 represents 0, 1, 2 or 3; p represents 0, 1 or 2; r represents 0, 1 or 2. ]
  • X 1 represents a halogen atom, nitro, methyl, difluoromethyl, trifluoromethyl, methylsulfonyl, difluoromethylsulfonyl or trifluoromethylsulfonyl
  • X 2 represents a hydrogen atom, a fluorine atom or a chlorine atom
  • Y 1 represents a halogen atom, methyl or methoxy
  • Y 2 represents a hydrogen atom, a fluorine atom, a chlorine atom or methyl
  • R 1 represents a hydrogen atom, a fluorine atom, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, benzyl, (Z) m- substituted phenylmethyl, cyclopropyl, C 1 -C 3 alkoxy, C 1- C 3 haloalkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, cyanomethoxy
  • Two Zs are —CH 2 CH 2 CH 2 —, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S (O) r —, —CH 2 CH 2.
  • Z a represents a halogen atom, methyl or trifluoromethyl
  • R 7 represents cyano, C 3 -C 6 cycloalkyl, —OR 13 , C 1 -C 4 alkylthio, —C (O) NH 2 or —C (S) NH 2
  • R 8 represents C 1 -C 4 alkyl or C 3 -C 4 cycloalkyl
  • R 9 represents —OR 14 or —S (O) r R 15
  • R 10 represents a hydrogen atom or methyl
  • R 11 represents methyl or ethyl
  • a 6-membered ring may be formed together with the atoms, in which case the hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted by a halogen atom, methyl, trifluoromethyl or methoxy, R 13 represents C 1 -C 4 alkyl or C 2 -C 4 haloalkyl, R 14 represents a hydrogen atom, methyl, ethyl or C 1 -C 2 haloalkyl, R 15 represents methyl, ethyl or C 1 -C 2 haloalkyl, n1 represents 0 or 1, n2 represents 0, [1] The alkynylphenyl-substituted amide compound or a salt thereof according to [1].
  • X 1 represents a halogen atom, methyl, difluoromethyl, trifluoromethyl or methylsulfonyl
  • X 2 represents a hydrogen atom or a fluorine atom
  • Y 1 represents a halogen atom or methyl
  • Y 2 represents a hydrogen atom, a fluorine atom or a chlorine atom
  • R 1 represents a hydrogen atom, a fluorine atom, methyl or methoxy
  • R 2 represents a hydrogen atom or a fluorine atom
  • R 1 and R 2 together form an ethylene chain, thereby forming a cyclopropyl ring with the carbon atom to which R 1 and R 2 are bonded
  • R 3 represents a hydrogen atom or methyl
  • R 4 represents a hydrogen atom
  • R 5 represents a hydrogen atom
  • R 6 is C 3 -C 6 cycloalkyl, phenyl substituted by (Z) m , D-1, D-2, D-6
  • R 12 represents a C 1 ⁇ C 4 alkyl
  • m represents 1, 2 or 3
  • n represents 0, 1 or 2
  • n1 represents 0, [2]
  • G 1 represents a structure represented by G 1 -1. [1] to [3] alkynylphenyl-substituted amide compound or a salt thereof.
  • X 1 represents a halogen atom, methyl or trifluoromethyl
  • X 2 represents a hydrogen atom or a fluorine atom
  • X 1 represents methyl or trifluoromethyl
  • X 2 represents a hydrogen atom
  • X 1 represents methyl or trifluoromethyl
  • X 2 represents a hydrogen atom
  • X 1 and X 2 represent a fluorine atom, [4] The alkynylphenyl-substituted amide compound or a salt thereof according to [4].
  • X 1 represents a halogen atom, nitro, difluoromethyl or methylsulfonyl
  • X 2 represents a hydrogen atom
  • X 1 represents a halogen atom or trifluoromethyl
  • X 2 represents a fluorine atom or a chlorine atom
  • X 1 represents a halogen atom or trifluoromethyl
  • X 2 represents a fluorine atom or a chlorine atom
  • X 1 represents a halogen atom or trifluoromethyl
  • X 2 represents a fluorine atom or a chlorine atom
  • G 1 represents a structure represented by G 1 -2 or G 1 -3, [1] to [3] alkynylphenyl-substituted amide compound or a salt thereof.
  • X 1 represents a halogen atom, difluoromethyl, trifluoromethyl or methylsulfonyl, [10] The alkynylphenyl-substituted amide compound or a salt thereof according to [10].
  • X 1 represents methyl, methylthio, trifluoromethylthio, methylsulfinyl, difluoromethylsulfonyl or trifluoromethylsulfonyl, [10] The alkynylphenyl-substituted amide compound or a salt thereof according to [10].
  • G 1 represents the structure represented by G 1 -4, [1] to [3] alkynylphenyl-substituted amide compound or a salt thereof.
  • X 1 represents a halogen atom or trifluoromethyl, [13] The alkynylphenyl-substituted amide compound or a salt thereof according to [13].
  • X 1 represents methyl or difluoromethyl, [13] The alkynylphenyl-substituted amide compound or a salt thereof according to [13].
  • G 1 represents a structure represented by G 1 -5 or G 1 -6
  • X 1 represents a halogen atom, [1] to [3] alkynylphenyl-substituted amide compound or a salt thereof.
  • X 1 represents a halogen atom, [16] The alkynylphenyl-substituted amide compound or a salt thereof according to [16].
  • X 1 represents methyl or difluoromethyl, [16] The alkynylphenyl-substituted amide compound or a salt thereof according to [16].
  • G 1 represents a structure represented by G 1 -7 or G 1 -8, [1] to [3] alkynylphenyl-substituted amide compound or a salt thereof.
  • X 1 represents a halogen atom or trifluoromethyl, [19] The alkynylphenyl-substituted amide compound or a salt thereof according to [19].
  • X 1 represents methyl or difluoromethyl, [19] The alkynylphenyl-substituted amide compound or a salt thereof according to [19].
  • G 1 represents a structure represented by G 1 -9, [1] to [3] alkynylphenyl-substituted amide compound or a salt thereof.
  • X 1 represents methyl or trifluoromethyl, r represents 0, 1 or 2; [22] The alkynylphenyl-substituted amide compound or a salt thereof according to [22].
  • X 1 represents trifluoromethyl, r represents 0, [23] The alkynylphenyl-substituted amide compound or a salt thereof according to [23].
  • Y 1 represents a halogen atom or methyl
  • Y 2 represents a hydrogen atom, [1] to [24], an alkynylphenyl-substituted amide compound or a salt thereof.
  • Y 1 represents a halogen atom
  • Y 2 represents a fluorine atom or a chlorine atom
  • Y 1 represents methoxy
  • Y 2 represents a hydrogen atom
  • Y 1 and Y 2 represent methyl, [1] to [24] an alkynylphenyl-substituted amide compound or a salt thereof.
  • R 1 represents C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, benzyl, phenylmethyl and cyclopropyl substituted by (Z) m
  • Z represents a halogen atom, cyano, nitro, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfonyl, trifluoromethylthio or trifluoromethylsulfonyl
  • m represents 1 or 2, and when m represents 2, each Z may be the same as or different from each other
  • R 2 represents a hydrogen atom
  • R 3 represents a hydrogen atom and methyl
  • R 4 represents a hydrogen atom, The alkynylphenyl-substituted amide compound or a salt thereof according to [1] to [28]. .
  • R 1 is C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, cyanomethoxy, benzyloxy, phenyl substituted by (Z) m
  • Z represents a halogen atom, cyano, nitro, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfonyl, trifluoromethylthio or trifluoromethylsulfonyl.
  • R 2 is a hydrogen atom
  • R 3 represents a hydrogen atom and methyl
  • R 4 represents a hydrogen atom
  • R 1 represents a fluorine atom or methoxy
  • R 2 represents a hydrogen atom or a fluorine atom
  • R 3 represents a hydrogen atom or methyl
  • R 4 represents a hydrogen atom, The alkynylphenyl-substituted amide compound or a salt thereof according to [1] to [28].
  • R 1 represents a hydrogen atom
  • R 2 represents a hydrogen atom
  • R 3 represents a hydrogen atom or methyl
  • R 4 represents a hydrogen atom
  • R 1 represents a fluorine atom
  • R 2 represents a fluorine atom
  • R 3 represents a hydrogen atom or methyl
  • R 4 represents a hydrogen atom
  • R 1 represents methoxy
  • R 2 represents a hydrogen atom
  • R 3 represents a hydrogen atom or methyl
  • R 4 represents a hydrogen atom
  • R 1 represents a fluorine atom, methyl, ethyl, ethoxy, trifluoroethoxy, allyloxy, propargyloxy, benzyloxy and methylthio;
  • R 2 represents a hydrogen atom,
  • R 3 represents a hydrogen atom or methyl,
  • R 4 represents a hydrogen atom,
  • R 1 represents a fluorine atom
  • R 2 represents a fluorine atom
  • R 3 represents ethyl
  • R 4 represents a hydrogen atom
  • R 1 represents a fluorine atom and methyl
  • R 2 represents methyl
  • R 3 represents a hydrogen atom and methyl
  • R 4 represents a hydrogen atom, The alkynylphenyl-substituted amide compound or a salt thereof according to [1] to [28].
  • R 1 and R 2 together form an ethylene chain to form a cyclopropyl ring with the carbon atom to which R 1 and R 2 are attached;
  • R 3 represents a hydrogen atom and methyl;
  • R 4 represents a hydrogen atom, The alkynylphenyl-substituted amide compound or a salt thereof according to [1] to [28].
  • R 1 represents a hydrogen atom
  • R 2 represents a hydrogen atom
  • R 3 represents C 1 -C 3 alkyl and C 1 -C 3 haloalkyl
  • R 4 represents a hydrogen atom and C 1 -C 3 alkyl, The alkynylphenyl-substituted amide compound or a salt thereof according to [1] to [28].
  • R 1 represents a hydrogen atom
  • R 2 represents a hydrogen atom
  • R 3 and R 4 together form an ethylene chain to form a cyclopropyl ring with the carbon atom to which R 3 and R 4 are attached.
  • R 1 represents a fluorine atom
  • R 2 represents a fluorine atom
  • R 3 represents methyl
  • R 4 represents methyl
  • R 1 represents C 1 -C 3 alkyl
  • R 2 represents a fluorine atom and methyl
  • R 3 represents a hydrogen atom and methyl
  • R 4 represents a hydrogen atom, The alkynylphenyl-substituted amide compound or a salt thereof according to [1] to [28].
  • R 5 represents a hydrogen atom, [1] to [42] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 5 represents C 1 -C 4 alkyl, [1] to [42] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 5 represents (C 1 -C 2 ) alkyl substituted by R 8 , R 8 represents cyano, C 3 -C 6 cycloalkyl or —OR 14 ;
  • R 14 represents C 1 -C 4 alkyl, the alkynylphenyl-substituted amide compound or a salt thereof according to [1] to [42].
  • R 5 represents C 3 -C 6 cycloalkyl, [1] to [42] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 5 represents cyclopropyl, [46] The alkynylphenyl-substituted amide compound or a salt thereof according to [46].
  • R 5 represents C 2 -C 4 alkenyl or C 3 -C 4 alkynyl, [1] to [42] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 5 represents C 1 -C 4 haloalkylthio, [1] to [42] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 5 represents —C (O) R 9 or C 1 -C 4 alkoxycarbonyl
  • R 9 represents C 1 -C 4 alkyl, [1] to [42] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 5 represents (C 1 -C 2 ) alkyl substituted by R 8
  • R 8 represents —OR 14 , C 1 -C 4 alkylthio, —C (O) NH 2 or —C (S) NH 2
  • R 14 represents C 2 -C 4 haloalkyl, [1] to [42] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 5 represents C 1 -C 4 alkoxy, [1] to [42] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 5 represents -C (O) R 9, R 9 represents C 3 -C 4 cycloalkyl, [1] to [42] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 6 represents C 3 -C 6 cycloalkyl, [1] to [53] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 6 represents C 3 -C 6 halocycloalkyl, [1] to [53] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 6 represents a hydrogen atom, a halogen atom, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, [1] to [53] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 6 is (C 1 -C 4 ) alkyl, hydroxy (C 3 -C 6 ) cycloalkyl, C 1 -C 2 alkoxy (C 3 -C 6 ) cycloalkyl, C 4 , optionally substituted with R 9 .
  • R 9 represents —OR 14 or —S (O) r R 15 ;
  • R 10 represents a hydrogen atom or methyl,
  • R 11 represents methyl or ethyl,
  • R 14 represents a hydrogen atom, methyl, ethyl or C 1 -C 2 haloalkyl,
  • R 15 represents methyl, ethyl or C 1 -C 2 haloalkyl, r represents 0, 1 or 2; [1] to [53] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 6 represents phenyl or phenyl substituted by (Z) m
  • Z is a halogen atom, cyano, nitro, —SF 5 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 ⁇ C 4 alkylsulfinyl, C 1 ⁇ C 4 alkylsulfonyl, C 1 ⁇ C 4 haloalkylthio, C 1 ⁇ C 4 haloalkylsulfinyl, C 1 ⁇ C 4 haloalkylsulfonyl, D-55 ⁇ D-59 or D-
  • each Z may be the same as or different from each other, and when two Zs are adjacent, Two adjacent Zs together form —CH 2 CH 2 CH 2 —, —CH 2 CH 2
  • a 5-membered ring or a 6-membered ring may be formed together with atoms, and at this time, each carbon atom forming the ring
  • the hydrogen atoms bonded to may optionally be substituted by a halogen atom, methyl or trifluoromethyl
  • Z a represents a halogen atom, methyl or trifluoromethyl
  • m represents 1, 2, 3, 4 or 5; [1] to [53] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 6 represents phenyl substituted by (Z) m , Z represents a halogen atom, and when m represents 2 or 3, each Z may be the same as or different from each other; m represents 1, 2 or 3; [58] The alkynylphenyl-substituted amide compound or a salt thereof according to [58]. [60] R 6 represents phenyl substituted by (Z) m , Z represents a halogen atom, m represents 1 or 2; [59] The alkynylphenyl-substituted amide compound or a salt thereof according to [59].
  • R 6 represents phenyl substituted by (Z) m , m represents 2, 3, 4 or 5; As for Z, at least two Z's are present at adjacent positions, and two adjacent Z's are taken together to form —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2.
  • R 12 represents C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 4 cycloalkylmethyl or C 3 -C 4 cycloalkyl, and when m represents 3, 4 or 5, the remaining Z Represents a halogen atom, cyano, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy, [1] to [53] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 6 represents phenyl substituted by (Z) m , m represents 2 or 3, At least two Z's are present at adjacent positions, and two adjacent Z's are taken together to form —CH 2 CH 2 O—, —OCH 2 O—, —OCH 2 CH 2 O—, —CH 2 CH 2.
  • N CH-, -N (R 12 )
  • a hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted by a halogen atom or methyl, and when m represents 3
  • the remaining Z represents methyl, R 12 represents C 1 -C 4 alkyl, [61] The alkynylphenyl-substituted amide compound or a salt thereof according to [61].
  • R 6 is D-1, D-2, D-6, D-8, D-9, D-17, D-19, D-23, D-24, D-25, D-26, D- 31, D-33, D-34, D-35, D-36, D-40, D-42, D-47, D-50, D-51 or D-52
  • Z represents a halogen atom, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 alkylsulfonyl, and n is 2, 3 or 4
  • Each Z may be the same as or different from each other, and when two Zs are adjacent, the two adjacent Zs are taken together to form —CH 2.
  • the hydrogen atom bonded to each carbon atom to be formed may be optionally substituted with a halogen atom, methyl, trifluoromethyl or methoxy, Z a represents a halogen atom, methyl or trifluoromethyl, n represents 0, 1, 2, 3 or 4; n1 represents 0 or 1, n2 represents 0, [1] to [53] alkynylphenyl-substituted amide compound or a salt thereof.
  • R 6 is D-1, D-2, D-6, D-8, D-9, D-23, D-25, D-26, D-31, D-33, D-40, D- Represents 47 or D-51, Z represents a halogen atom, methyl or trifluoromethyl, and when n represents 2, each Z may be the same as or different from each other, and two Zs are adjacent to each other In some cases, two adjacent Zs may be joined together to form —CH ⁇ CHCH ⁇ CH— to form a 6-membered ring with the carbon atom to which each Z is attached.
  • R 12 represents a C 1 ⁇ C 4 alkyl
  • n represents 0, 1 or 2
  • n1 and n2 represent 0, [63]
  • N CH-, -N (R 12 )
  • a hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted by a halogen atom or methyl, and when m represents 3
  • the remaining Z represents methyl, R 12 represents C 1 -C 4 alkyl; r represents 0, 1 or 2.
  • R 12 represents a C 1 ⁇ C 4 alkyl
  • a pest control composition comprising, as an active ingredient, at least one selected from the alkynylphenyl-substituted amide compounds or salts thereof according to [1] to [64].
  • a mammal or avian antifungal or parasite control composition comprising one or more selected from the alkynylphenyl-substituted amide compounds or salts thereof according to [1] to [64] as active ingredients.
  • An agricultural and horticultural fungicide or nematicide composition comprising, as an active ingredient, one or more selected from the alkynylphenyl-substituted amide compounds or salts thereof according to [1] to [64].
  • [73] The agricultural and horticultural fungicide or nematicide composition for treating soil on which plants grow.
  • the compound of the present invention represented by the formula (I) and a pest control agent containing the compound as an active ingredient are excellent control for pests in the fields of agriculture, horticulture and livestock / hygiene, especially fungi and linear animals. It exerts its effect and exerts a sufficient control effect against those pests that have acquired resistance to existing drugs. Furthermore, there is almost no adverse effect on non-target organisms such as plants, mammals, fish, useful insects and natural enemies, low persistence and light environmental impact. Therefore, the present invention can provide a useful novel pest control agent.
  • an optically active substance resulting from the presence of one or more asymmetric carbon atoms may be present depending on the substituent.
  • the present invention encompasses all optically active forms or racemates.
  • geometric isomers of E-form and Z-form may exist depending on the substituent, but the present invention is not limited to these E-form, Z-form or E-form. And a mixture containing the Z-form in an arbitrary ratio.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the notation “halo” also represents these halogen atoms.
  • n- is “normal”
  • i- is “iso”
  • sec- is “secondary”
  • tert- is “tarsha”.
  • Lee means each.
  • C a -C b alkyl represents a linear or branched hydrocarbon group having a carbon number of a to b, such as methyl, ethyl, n-propyl, i-propyl, n Specific examples include -butyl, i-butyl, sec-butyl, tert-butyl, pentyl, 1-ethylpropyl, 2,2-dimethylpropyl, hexyl, etc., each selected within the specified number of carbon atoms.
  • C a -C b haloalkyl is a linear or branched hydrocarbon group having a carbon number of a to b, wherein a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom In this case, when two or more halogen atoms are substituted, the halogen atoms may be the same as or different from each other.
  • C a -C b cycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms, and forms a monocyclic or complex ring structure having 3 to 10 members. I can do it.
  • Each ring may be optionally substituted with alkyl within the range of the specified number of carbon atoms. Specific examples include, for example, cyclopropyl, cyclobutyl, 1-methylcyclopropyl, 2-methylcyclopropyl, cyclopentyl, 2,2-dimethylcyclopropyl, 1-methylcyclobutyl, cyclohexyl and the like. The range is selected.
  • C a -C b halocycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom.
  • a monocyclic or complex ring structure from a member ring to a 10-member ring can be formed.
  • Each ring may be optionally substituted with alkyl within the range of the specified number of carbon atoms, and the substitution with a halogen atom may be a ring structure portion, a side chain portion, or both
  • the halogen atoms may be the same as or different from each other.
  • C a -C b alkenyl refers to an unsaturated carbonization which is linear or branched having 1 to 2 carbon atoms and has one or more double bonds in the molecule.
  • Represents a hydrogen group for example vinyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 2-methyl-2-
  • Specific examples include propenyl, 3-methyl-3-butenyl and the like, each selected within the range of the specified number of carbon atoms.
  • C a -C b haloalkenyl is a linear or branched chain having a carbon number of a to b in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and An unsaturated hydrocarbon group having one or more double bonds in the molecule.
  • these halogen atoms may be the same as or different from each other.
  • C a -C b cycloalkenyl represents an unsaturated hydrocarbon group having a cyclic structure of 1 to 2 carbon atoms and having one or more double bonds.
  • 10-membered monocyclic or complex ring structures can be formed.
  • Each ring may be optionally substituted with alkyl within the range of the specified number of carbon atoms, and the double bond may be either endo- or exo-.
  • Specific examples include 1-cyclopentenyl, 2-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl, bicyclo [2.2.1] -5-hepten-2-yl, and the like. It is selected in the range of the number of atoms.
  • C a -C b halocycloalkenyl is a cyclic group consisting of a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and one in the molecule or It represents an unsaturated hydrocarbon group having two or more double bonds, and can form a monocyclic or complex ring structure having 3 to 10 members.
  • Each ring may be optionally substituted with alkyl within the range of the specified number of carbon atoms, and the double bond may be either endo- or exo-. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other.
  • C a -C b alkynyl refers to an unsaturated hydrocarbon having a linear or branched chain composed of a to b carbon atoms and having one or more triple bonds in the molecule.
  • ethynyl 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 1-hexynyl, 3-hexynyl
  • 1-pentynyl 2-pentynyl
  • 2-hexynyl 1-hexynyl
  • 3-hexynyl 3-hexynyl
  • 3-hexynyl Specific examples include 3-methyl-1-pentynyl, 4-methyl-1-pentynyl, 3,3-dimethyl-1-butynyl, etc., each selected within the specified number of carbon atoms.
  • C a -C b haloalkynyl is a linear or branched chain having a carbon number of a to b in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and An unsaturated hydrocarbon group having one or more triple bonds in the molecule.
  • these halogen atoms may be the same as or different from each other.
  • C a -C b alkoxy denotes an alkyl-O— group as defined above consisting of a to b carbon atoms, eg methoxy, ethoxy, n-propyloxy, i-propyloxy, Specific examples include n-butyloxy, i-butyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, and the like, each selected within the range of the specified number of carbon atoms.
  • C a -C b haloalkoxy represents a haloalkyl-O— group with the above meanings consisting of a to b carbon atoms, for example difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoro Methoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2, -tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 1, , 1,2,3,3,3-hexafluoropropyloxy and the like are listed as specific examples, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkenyloxy represents an alkenyl-O— group having the above meaning consisting of a to b carbon atoms, such as 2-propenyloxy, 2-butenyloxy, 1-methyl- Specific examples include 2-propenyloxy, 2-methyl-2-propenyloxy, 3-methyl-2-butenyloxy, 1,1-dimethyl-2-propenyloxy, etc., within each specified number of carbon atoms. Selected.
  • C a -C b haloalkenyloxy represents a haloalkenyl-O— group with the above meaning consisting of a to b carbon atoms, for example 2-fluoro-2-propenyloxy, 2- Chloro-2-propenyloxy, 3-chloro-2-propenyloxy, 3,3-difluoro-2-propenyloxy, 2,3-dichloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 2, Specific examples include 1,3,3-trifluoro-2-propenyloxy and the like, each selected within the range of the designated number of carbon atoms.
  • C a -C b alkynyloxy represents an alkynyl-O— group as defined above consisting of a to b carbon atoms, for example 2-propynyloxy, 2-butynyloxy, 1-methyl- Specific examples include 2-propynyloxy, 1,1-dimethyl-2-propynyloxy, etc., and each is selected in the range of the designated number of carbon atoms.
  • C a -C b haloalkynyloxy represents a haloalkynyl-O— group with the above meaning consisting of a to b carbon atoms, for example 3-chloro-2-propynyloxy, 3- Specific examples include bromo-2-propynyloxy, 3-iodo-2-propynyloxy and the like, each selected within the specified number of carbon atoms.
  • C a -C b alkylthio represents an alkyl-S— group having the above-mentioned meanings consisting of a to b carbon atoms, for example methylthio, ethylthio, n-propylthio, i-propylthio, n- Specific examples include butylthio, i-butylthio, sec-butylthio, tert-butylthio and the like, each selected within the specified number of carbon atoms.
  • C a -C b alkylsulfinyl represents an alkyl-S (O) — group having the above meanings consisting of a to b carbon atoms, for example methylsulfinyl, ethylsulfinyl, n-propylsulfinyl. , I-propylsulfinyl and the like are listed as specific examples, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylsulfonyl represents an alkyl-SO 2 — group having the above-mentioned meanings consisting of a to b carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i Specific examples include -propylsulfonyl and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b haloalkylthio represents a haloalkyl-S— group having the above meanings consisting of a to b carbon atoms, such as difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, trichloromethylthio.
  • C a -C b haloalkylsulfinyl represents a haloalkyl-S (O) — group having the above-mentioned meanings consisting of a to b carbon atoms, such as difluoromethylsulfinyl, trifluoromethylsulfinyl and the like. Specific examples are given, each selected in the range of the specified number of carbon atoms.
  • C a -C b haloalkylsulfonyl represents a haloalkyl-SO 2 — group having the above-mentioned meaning consisting of a to b carbon atoms, such as difluoromethylsulfonyl, trifluoromethylsulfonyl and the like. Each selected within a range of each specified number of carbon atoms.
  • di (C a -C b alkyl) amino refers to an alkyl having the above meaning consisting of a to b carbon atoms, both of which may be the same or different from each other.
  • C a -C b alkoxyamino represents an alkyl-ONH— group as defined above consisting of a to b carbon atoms, eg methoxyamino, ethoxyamino, n-propyloxyamino, i Specific examples include -propyloxyamino, n-butyloxyamino, i-butyloxyamino, sec-butyloxyamino, tert-butyloxyamino and the like, each selected within the range of the designated number of carbon atoms.
  • tri (C a -C b alkyl) silyl refers to a silyl group substituted with an alkyl having the above-mentioned meaning consisting of a to b carbon atoms, which may be the same or different from each other.
  • Specific examples include trimethylsilyl, triethylsilyl, tri (n-propyl) silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl, tert-butyldimethylsilyl and the like. , Each selected range of carbon atoms.
  • C a -C b alkylcarbonyl represents an alkyl-C (O) — group having the above meaning consisting of a to b carbon atoms, for example acetyl, propionyl, butyryl, isobutyryl, valeryl, Specific examples include isovaleryl, 2-methylbutanoyl, pivaloyl and the like, and each is selected in the range of the designated number of carbon atoms.
  • C a -C b cycloalkylcarbonyl denotes a cycloalkyl-C (O) — group having the above meanings consisting of a to b carbon atoms, such as cyclopropylcarbonyl, cyclobutylcarbonyl, Specific examples include 1-methylcyclopropylcarbonyl, 2-methylcyclopropylcarbonyl, cyclopentylcarbonyl, 2,2-dimethylcyclopropylcarbonyl, cyclohexylcarbonyl, etc., and each is selected in the range of the designated number of carbon atoms.
  • C a -C b alkoxycarbonyl represents an alkyl-OC (O) — group having the above-mentioned meanings consisting of a to b carbon atoms, for example methoxycarbonyl, ethoxycarbonyl, n-propyloxy Specific examples include carbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, tert-butoxycarbonyl, etc., each selected within the range of the specified number of carbon atoms.
  • (C a -C b ) alkyl substituted by R 7 means that the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is substituted by any R 7 consists of a to b Each selected from a range of each specified number of carbon atoms.
  • the notation “(C a -C b ) alkyl optionally substituted with R 9 ” refers to the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with any R 9 from a to b
  • the above-mentioned meaning is an alkyl group, and each is selected within the range of the designated number of carbon atoms.
  • each R 9 may be the same as or different from each other.
  • “C a -C b cycloalkyl (C d -C e ) cycloalkyl, hydroxy (C d -C e ) cycloalkyl”, “C a -C b alkoxy (C d -C e ) cycloalkyl” or phenyl ( C d -C e ) cycloalkyl is represented by any C a -C b cycloalkyl, hydroxyl group, any C a -C b alkoxy, or phenyl, as defined above, to a carbon atom, respectively.
  • It represents a cycloalkyl group having the above-mentioned meaning consisting of d to e carbon atoms in which the bonded hydrogen atoms are substituted, and is selected in the range of each designated number of carbon atoms.
  • the expressions “cyano (C a -C b ) alkoxy”, “phenyl (C a -C b ) alkoxy” or “(Z) m- substituted phenyl (C a -C b ) alkoxy” are cyano
  • phenyl Or (Z) represents an alkoxy group having the above-mentioned meaning of the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is substituted by phenyl substituted by m , and each of the designated number of carbon atoms. The range is selected.
  • R 1 and R 2 together form a C 2 -C 9 alkylene chain to form a 3- to 6-membered ring with the carbon atom to which R 1 and R 2 are bonded, and this alkylene chain 1 to 2 carbon atoms may be substituted with an oxygen atom, a sulfur atom or a nitrogen atom, and as a specific example of the notation, for example, cyclopropane, oxirane, thiirane, aziridine, cyclobutane, oxetane, thietane, azetidine Cyclopentane, oxolane, thiolane, pyrrolidine, dioxolane, dithiolane, cyclohexane, tetrahydropyran, tetrahydrothiopyran, piperidine, 1,3-dioxane, 1,3-dithiane, etc.
  • R 16 and R 17 together form a C 2 -C 9 alkylene chain to form a 3- to 6-membered ring with the nitrogen atom to which R 16 and R 17 are bonded.
  • one carbon atom of the alkylene chain may be substituted with an oxygen atom or a sulfur atom.
  • Specific examples of the notation include, for example, aziridine, azetidine, pyrrolidine, oxazolidine, thiazolidine, piperidine, 2H-3, 4,5,6-tetrahydro-1,3-oxazine, morpholine, 2H-3,4,5,6-tetrahydro-1,3-thiazine, thiomorpholine, etc. Selected.
  • examples of the preferred range of the substituent represented by G 1 include the following groups. That is, G 1 -I: G 1 -1 [where X 1 represents methyl or trifluoromethyl, and X 2 represents a hydrogen atom. ]. G 1 -II: G 1 -1 [where X 1 and X 2 represent a fluorine atom. ]. G 1 -III: G 1 -2 and G 1 -3 [wherein X 1 represents a halogen atom, difluoromethyl, trifluoromethyl or methylsulfonyl. ]. G 1 -IV: G 1 -4 [where X 1 represents a halogen atom or trifluoromethyl. ].
  • G 1 -V G 1 -5 and G 1 -6 [where X 1 represents a halogen atom. ].
  • G 1 -VI G 1 -7 and G 1 -8 [wherein X 1 represents a halogen atom or trifluoromethyl. ].
  • G 1 -VII G 1 -9 [wherein X 1 represents trifluoromethyl and r represents 0. ].
  • G 1 -VIII G 1 -1 [wherein X 1 represents a halogen atom, nitro, difluoromethyl or methylsulfonyl, and X 2 represents a hydrogen atom. ].
  • G 1 -IX G 1 -1 [where X 1 represents a halogen atom or trifluoromethyl, and X 2 represents a fluorine atom or a chlorine atom. ].
  • G 1 -X G 1 -2 and G 1 -3 [wherein X 1 represents methyl, methylthio, trifluoromethylthio, methylsulfinyl, difluoromethylsulfonyl or trifluoromethylsulfonyl. ].
  • G 1 -XI G 1 -4 [where X 1 represents methyl or difluoromethyl. ].
  • G 1 -XII G 1 -5 and G 1 -6 [wherein X 1 represents methyl or trifluoromethyl. ].
  • G 1 -XIII G 1 -7 and G 1 -8 [wherein X 1 represents methyl or difluoromethyl. ].
  • G 1 -XIV G 1 -9 [wherein X 1 represents methyl or trifluoromethyl, and r represents 0, 1 or 2. ].
  • examples of combinations of preferable ranges of the substituents represented by Y 1 and Y 2 include the following groups YI to Y-IV. That is, YI: Y 1 is a halogen atom or methyl, and Y 2 is a hydrogen atom. Y-II: Y 1 is a halogen atom, and Y 2 is a fluorine atom or a chlorine atom. Y-III: Y 1 is methoxy and Y 2 is a hydrogen atom. Y-IV: Y 1 and Y 2 are methyl at the same time. Among these, YI and Y-II are more preferable as a combination of substituents represented by Y 1 and Y 2 , and YI is particularly preferable.
  • examples of combinations of preferred ranges of the substituents represented by R 1 , R 2 , R 3 and R 4 include the following groups of RI to R-XIII. That is, RI: R 1 and R 2 are hydrogen atoms, R 3 is a hydrogen atom and methyl, and R 4 is a hydrogen atom. R-II: R 1 and R 2 are fluorine atoms, R 3 is a hydrogen atom and methyl, and R 4 is a hydrogen atom. R-III: R 1 is methoxy, R 2 is a hydrogen atom, R 3 is a hydrogen atom and methyl, and R 4 is a hydrogen atom.
  • R-IV R 1 is a fluorine atom, methyl, ethyl, ethoxy, trifluoroethoxy, allyloxy, propargyloxy, benzyloxy and methylthio, R 2 is a hydrogen atom, R 3 is a hydrogen atom and methyl, and R 4 is a hydrogen atom .
  • RV R 1 and R 2 are fluorine atoms, R 3 is ethyl, and R 4 is a hydrogen atom.
  • R-VI R 1 is a fluorine atom and methyl, R 2 is methyl, R 3 is a hydrogen atom and methyl, and R 4 is a hydrogen atom.
  • R-VII R 1 and R 2 together form an ethylene chain to form a cyclopropyl ring with the carbon atom to which R 1 and R 2 are bonded, R 3 is a hydrogen atom and methyl, and R 4 is a hydrogen atom.
  • R-VIII R 1 and R 2 are hydrogen atoms, R 3 is C 1 -C 3 alkyl and C 1 -C 3 haloalkyl, and R 4 is hydrogen atom and C 1 -C 3 alkyl.
  • R-IX R 1 and R 2 are hydrogen atoms, and R 3 and R 4 together form an ethylene chain, thereby forming a cyclopropyl ring with the carbon atom to which R 3 and R 4 are bonded.
  • RX is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, benzyl, phenylmethyl substituted by (Z) m [where Z is a halogen atom, cyano, nitro, methyl, trifluoromethyl, Methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfonyl, trifluoromethylthio or trifluoromethylsulfonyl, m represents 1 or 2, and m represents 2 Each Z may be the same as or different from each other.
  • R 2 is a hydrogen atom
  • R 3 is a hydrogen atom and methyl
  • R 4 is a hydrogen atom.
  • R-XI R 1 is replaced by C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, cyanomethoxy, benzyloxy, (Z) m [Wherein Z is a halogen atom, cyano, nitro, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfonyl, trifluoromethylthio] Alternatively, it represents trifluoromethylsulfonyl, m represents 1 or 2, and when m represents 2, each Z may be the same as or different from each other
  • R 2 is a hydrogen atom
  • R 3 is a hydrogen atom and methyl
  • R 4 is a hydrogen atom
  • R-XII R 1 and R 2 are fluorine atoms
  • R 3 and R 4 are methyl
  • R-XIII R 1 is C 1 -C 3 alkyl, R 2 is a fluorine atom and methyl, R 3 is a hydrogen atom and methyl, and R 4 is a hydrogen atom.
  • RI-R-VII and R-XII are more preferred as combinations of the ranges of substituents represented by R 1 , R 2 , R 3 and R 4 , and further, RI-R-III and R -VII is particularly preferred.
  • examples of the preferred range of the substituent represented by R 5 include the following groups. That is, R 5 -I: a hydrogen atom. R 5 -II: C 1 -C 4 alkyl. R 5 -III: (C 1 -C 2 ) alkyl substituted by R 8 [wherein R 8 represents cyano, C 3 -C 6 cycloalkyl or —OR 14 and R 14 represents C 1 -C 4 Represents alkyl. ].
  • R 5 -IV cyclopropyl.
  • R 5 -V C 2 -C 4 alkenyl and C 3 -C 4 alkynyl.
  • R 5 -VI C 1 -C 4 haloalkylthio.
  • R 5 -VII —C (O) R 9 [wherein R 9 represents C 1 -C 4 alkyl. And C 1 -C 4 alkoxycarbonyl.
  • R 5 -VIII (C 1 -C 2 ) alkyl substituted by R 8 [where R 8 is —OR 14 , C 1 -C 4 alkylthio, —C (O) NH 2 or —C (S) NH 2 represents R 14 represents C 2 -C 4 haloalkyl. ].
  • R 5 -IX C 3 -C 6 cycloalkyl.
  • R 5 -X C 1 -C 4 alkoxy.
  • R 5 -XI —C (O) R 9 wherein R 9 represents C 3 -C 4 cycloalkyl.
  • R 5 -I ⁇ R 5 -VIII and R 5 -XI as range of the substituent of R 5, further, R 5 -I ⁇ R 5 -III and R 5 -V ⁇ R 5 -VII is particularly preferred.
  • examples of the preferred range of the substituent represented by R 6 include the following groups. That is, R 6 -I: C 3 -C 6 cycloalkyl. R 6 -II: (Z) phenyl substituted by m [wherein Z represents a halogen atom, and when m represents 2 or 3, each Z may be the same as or different from each other] And m represents 1, 2 or 3. ].
  • R 6 -IV D-1, D-2, D-6, D-8, D-9, D-23, D-25, D-26, D-31, D-33, D-40, D -47 and D-51 [wherein Z represents a halogen atom, methyl or trifluoromethyl, and when n represents 2, each Z may be the same as or different from each other. Furthermore, when two Zs are adjacent to each other, the two adjacent Zs together form —CH ⁇ CHCH ⁇ CH— to form a 6-membered ring with the carbon atom to which each Z is bonded.
  • the hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted with a halogen atom
  • R 12 represents C 1 -C 4 alkyl
  • Z is When R 12 is adjacent to R 12 , R 12 together with Z forms —CH ⁇ CHCH ⁇ CH— to form a 6-membered ring with the atoms to which R 12 and Z are bonded.
  • N may be 0, 1 or Represents 2, and n1 and n2 represent 0. ].
  • R 6 -V hydrogen atom, halogen atom, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl.
  • R 6 -VII C 3 ⁇ C 6 halocycloalkyl.
  • R 6 -VIII phenyl and phenyl substituted by (Z) m [where Z is a halogen atom, cyano, nitro, —SF 5 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1- C 4 alkoxy, C 1 ⁇ C 4 haloalkoxy, C 1 ⁇ C 4 alkylthio, C 1 ⁇ C 4 alkylsulfinyl, C 1 ⁇ C 4 alkylsulfonyl, C 1 ⁇ C 4 haloalkylthio, C 1 ⁇ C 4 haloalkylsulfinyl , C 1 -C 4 haloalkylsulfonyl, D-55 to D-59 or D-61, and when m represents 2, 3, 4 or 5, each Z may be the same as each other or In addition, when two Zs are
  • the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom.
  • Cyano, methyl, diph Oromechiru may be optionally substituted by trifluoromethyl or methoxy
  • R 12 is C 1 ⁇ C 4 alkyl, C 1 ⁇ C 4 haloalkyl, C 3 ⁇ C 4 cycloalkylmethyl or C 3 ⁇ C 4 cycloalkyl
  • m represents 3, 4 or 5
  • the remaining Z represents a halogen atom, cyano, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy
  • r represents 0, 1 or 2 .
  • R 6 -X D-1, D-2, D-6, D-8, D-9, D-17, D-19, D-23, D-24, D-25, D-26, D -31, D-33, D-34, D-35, D-36, D-40, D-42, D-47, D-50, D-51 and D-52 [where Z is a halogen atom , Cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 alkylsulfonyl, and when n is 2, 3 or 4, Z may be the same as or different from each other.
  • the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, methyl, trifluoromethyl or the like. or may be optionally substituted by methoxy
  • the hydrogen atoms bonded to each carbon atom forming the ring is a halogen atom, methyl, may be optionally substituted by trifluoromethyl or methoxy
  • Z a is a halogen atom, methyl
  • n represents 0, 1, 2, 3 or 4 represents
  • n1 represents 0 or 1
  • n2 represents 0, r represents 0, 1 or 2.
  • R 6 -I ⁇ R 6 -IV, R 6 -VI and R 6 -VIII ⁇ R 6 -X is as range of the substituent of R 6, further, R 6 -III R 6 -IV, R 6 -IX and R 6 -X are particularly preferred.
  • Each group which shows the preferable range of each substituent in these compounds included in this invention can be combined arbitrarily, respectively, Each represents the preferable range of this invention compound.
  • Examples of preferred ranges of combinations of G 1 , R 1 to R 4 (indicated by RI to R-XIII) and R 6 of the compound represented by the formula (I) include the combinations shown in the following Table 1. Is mentioned. However, the combinations in Table 1 are for illustration, and the compounds of the present invention represented by the formula (I) are not limited to these.
  • those that can be converted into acid addition salts according to a conventional method are, for example, hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydrogen iodide.
  • Hydrohalic acid salts such as acids, inorganic acid salts such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfone Salts of sulfonic acids such as acids, formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid A salt of a carb
  • those that can be converted into a metal salt according to a conventional method are, for example, alkali metal salts such as lithium, sodium, and potassium, calcium, and barium.
  • alkali metal salts such as lithium, sodium, and potassium, calcium, and barium.
  • An alkaline earth metal salt such as magnesium, or an aluminum salt.
  • the term “pest control agent” means a fungicide and a parasite control agent that are intended to control harmful pathogens and parasites that infect or infest plants or animals. It means fungicides and nematicides in the field of horticulture, or animal antifungal agents and endoparasite control agents.
  • the term “pathogenic bacteria” means microorganisms that cause plant diseases and animal infectious diseases. Specific examples include the following microorganisms, but specific examples of microorganisms are not limited to these. It is not something. Taphrina spp. (Eg Taphrina deformans, T. pruni etc.), Pneumocystis spp., Geotrichum spp., Candida spp. (Eg Candida albicans, C. sorbosa etc.), Pichia spp. (Eg Pichia kluyveri etc.), Capnodium spp. Fumago spp., Hypocapnodium spp., Cercospora spp.
  • Taphrina spp. Eg Taphrina deformans, T. pruni etc.
  • Pneumocystis spp. Geotrichum spp.
  • Candida spp. Eg Candida albicans, C. sorbosa
  • Cercospora apii C. asparagi, C. beticola, C. capsici, C. carotae, C. kaki, C. kikuchii, C. zonata, etc.
  • Cercosporidium spp. Cladosporium spp.
  • Cladosporium colocasiae C. cucumerinum, C. variabile etc.
  • Davidiella spp. Didymosporium spp.
  • Heterosporium spp. Eg Heterosporium allii etc.
  • Mycosphaerella spr. cerasella M. fijiensis, M. fragariae, M. graminicola, M.
  • Sphaceloma spp. eg Sphaceloma caricae etc.
  • Ascochyta spp. eg Ascochyta pisi etc.
  • Corynespora spp. eg Corynespora cassiicola et al.
  • Leptosphaeria spp. eg Leptosphaeria coniothyrium, L. ., Phaeosphaeria spp., Ophiosphaerella spp., Setophoma spp., Helminthosporium spp., Alternaria spp. (E.g. Alternaria alternata, A. brassicae, A.
  • brassicicola A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A mali, A. panax, A. porri, A. radicina, A. solani etc.
  • Bipolaris spp. eg Bipolaris sorghicola etc.
  • Cochliobolus spp. eg Cochliobolus heterostrophus, C. lunatus, C. miyabeanus etc.
  • Curvularia spp. eg Curvularia geniculata, C. verruculosa etc.
  • Drechslera spp. Pleospora spp.
  • Dothiorella spp. Fusicoccum spp., Guignardia spp., Lasiodiplodia spp. (eg Lasiodiplodia theobromae, etc.), Macrophoma spp. spp., Phyllosticta spp. (eg, Phyllosticta zingiberis), Schizothyrium spp. (eg, Schizothyrium pomi), Acrospermum spp., Leptosphaerulina spp., Aspergillus spp., Penicillium spp. (eg, Penicillium digitum, P. italicumigen, P.
  • Phyllosticta spp. eg, Phyllosticta zingiberis
  • Schizothyrium spp. eg, Schizothyrium pomi
  • Acrospermum spp. Leptosphaerulin
  • Leveillula spp. (Eg, Leveillula taurica, etc.) Microsphaera spp., Oidium spp. (E.g. Oidium Neolycopersici etc.), Phyllactinia spp. (E.g. Phyllactinia kakicola, P. Mali, P. Moricola etc.),
  • Podosphaera spp. (Eg Podosphaera fusca, P. leucotricha, P. pannosa, P. tridactyla var. Tridactyla, P. xanthii etc.), Sphaerotheca spp. (Eg Sphaerotheca aphanis var. Aphanis, S. fulcinnea etc.)
  • Uncinula necator, U. n. Var. Necator, etc. Uncinuliella spp.
  • Uncinuliella simulans var. Simulans, U. s. Var. Tandae, etc. Blumeriella spp.
  • Cylindrosporium spp. spp. eg, Diplocarpon mali, D. mespili, D. rosae, etc.
  • Gloeosporium spp. eg, Gloeosporium minus, etc.
  • Marssonina spp. Tapesia spp. (eg, Tapesia acuformis, T. ⁇ yallundae, etc.), Sachnum spp. spp.
  • Botryotinia spp. eg Botryotinia fuckeliana
  • Botrytis spp. eg Botrytis allii, B.
  • Gnomonia spp. Coniella spp., Coryneum spp., Greeneria spp., Melanconis spp., Cytospora spp., Leucostoma spp., Valsa spp. (eg Valsa ceratosperma etc.), Tubakia spp. cus spp., Clasterosporium spp., Gaeumannomyces spp. (eg Gaeumannomyces graminis etc.), Magnaportheorspp. (eg Magnaporthe grisea etc.), PyriculariaPspp. (eg Pyricularia zingiberis etc.),
  • Septobasidium spp. Eg, Septobasidium bogoriense, S. tanakae, etc.
  • Helicobasidium spp. Eg, Helicobasidium longisporum, etc.
  • Coleosporium spp. P. pachyrhizi etc. Physopella spp.
  • Physopella psi ampelopsidis etc. Physopella psi ampelopsidis etc.
  • Kuehneola spp. Eg Kuehneola japonica etc.
  • Phragmidium spp. For example, Gymnosporangium asiaticum, G. yamadae, etc.), Puccinia spp. (Eg Puccinia allii, P.
  • Armillaria spp. Hellotium spp., Lepista spp. (eg Lepista subnuda etc.), Sclerotium spp. (eg Sclerotium cepivorum etc.), Typhula spp. (eg Typhula incarnata, T. ishikariensis var. ishikariensis etc.) spp. (eg Athelia rolfsii), Ceratobasidium spp. (eg Ceratobasidium cornigerum etc.), Ceratorhiza spp., Rhizoctonia spp. (eg Rhizoctonia solani etc.), Thanatephorus spp. Basidiomycota fungi such as Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, Phanerochaete spp.
  • Basidiomycota fungi such as Fomitiporia spp
  • Chipidiomycota fungi such as Olpidium spp.
  • Blastocladiomycota fungi such as Physoderma spp. Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (Eg Mucor fragilis), Rhizopus spp. (Eg Rhizopus arrhizus, R. chinensis, R. oryzae, R. stolonifer var. Stolonifer), etc. .
  • Cercozoa protists such as Plasmodiophora spp. (For example, Plasmodiophora brassicae), Spongospora subterranea f. Sp. Subterranea, etc.
  • Aphanomyces spp. (Eg Aphanomyces cochlioides, A. raphani etc.), Albugo spp. (Eg Albugo macrospora, A. wasabiae etc.), Bremia spp. (Eg Bremia lactucae etc.), Hyaloperonospora spp., Peronosclerospora spp., Peronospora spp.
  • Peronospora alliariae-wasabi P. chrysanthemi-coronarii, P. destructor, P. farinosa f. Sp. Spinaciae, P. manshurica, P. parasitica, P.
  • Pseudoperonospora spp. Eg, Pseudoperonospora cubensis, etc.
  • Sclerophthora spp. Phytophthora spp. infestans, P. melonis, P. nicotianae, P. palmivora, P. porri, P. sojae, P. syringae, P. vignae f. sp. adzukicola, etc.
  • Pythium spp. eg Pythium afertile, P. aphanidermatum, P.
  • Actinobacter gram-positive bacteria such as Clavibacter spp. (Eg Clavibacter michiganensis subsp. Michiganensis), Curtobacterium spp., Leifsonia spp. (Eg Leifsonia xyli subsp. Xyli etc.), Streptomyces spp. (Eg Streptomyces ipomoeae etc.) .
  • Firmicutes gram-positive fungi such as Clostridium sp.
  • Tenericutes gram-positive fungi such as Phytoplasma. Rhizobium spp. (Eg Rhizobium radiobacter), Acetobacter spp., Burkholderia spp. (Eg Burkholderia andropogonis, B. cepacia, B. gladioli, B. glumae, B. plantarii etc.), Acidovorax avenae subsp. Subsp. Citrulli, A. konjaci, etc.), Herbaspirillum spp., Ralstonia spp.
  • Xanthomonas spp. Eg, Ralstonia solanacearum
  • Xanthomonas spp. Eg, Xanthomonas albilineans, X. arboricola pv. Pruni, X. axonopodis pv. Vitians
  • X. campestris pv. Campestris X. c. Pv. Cucurbitae
  • X. c. Pv. Glycines X. c. Pv. Mangiferaeindicae
  • X. c. Pv. Nigromaculans X. c. Pv. Vesicatoria
  • Pseudomonas spp. eg Pseudomonas cichorii, P. fluorescens, P. marginalis, P. m. pv. marginalis, P. savastanoi pv. glycinea, P. syringae, P s.pv.actinidiae, P.s.pv.eriobotryae, P.s.pv.helianthi, P.s.pv.lachrymans, P.s.pv.maculicola, P.s.pv.mori, P.s pv. morsprunorum, P. p. spinaciae, P. s.
  • Pseudomonas spp. eg Pseudomonas cichorii, P. fluorescens, P. marginalis, P. m. pv. marginalis, P. savastanoi pv. glycinea, P
  • Rhizobacter spp. Rhizobacter spp.
  • Brenneria spp. eg, Brenneria nigrifluens etc.
  • Dickeya spp. eg, Dickeya dianthicola, D. zeae etc.
  • Erwinia spp. Eg Erwinia amylovora, E. rhapontici etc.
  • Pantoea spp. Pectobacterium spp. (Eg Pectobacterium atrosepticum, P. carotovorum, P. wasabiae etc.) gram of Proteobacteria gram Negative fungi.
  • plant diseases and animal infections caused by infection and growth of these pathogenic bacteria include the following plant diseases and animal infections, but specific examples of plant diseases and animal infections are limited to these. Is not to be done.
  • Plant diseases Leaf curl (Taphrina deformans), Plum pockets (Taphrina pruni), Asparagus brown spot Leaf spot (Cercospora asparagi), sugar beet brown spot Cercospora leaf spot (Cercospora beticola), pepper spot Frogeye leaf spot (Cercospora capsici), oyster horn spot leaf disease Angular leaf spot (Cercospora kaki), soybean purpura purple stain (Cercospora kikuchii), groundnut brown leaf spot (Mycosphaerella arachidis), sweet cherry brown spot disease (Cylindrosporium leaf spot) Mycosphaerella cerasella, Blumeriella jaapii), wheat leaf blight, Speckled leaf blotch (Mycosphaerella graminicola), oyster lobster circular leaf spot (Mycosphaerella nawae), pea brown spot Mycosphaerella blight (Mycosphaerella pinodes), myaf spot Mycos
  • Corn sesame leaf blight Southern leaf blight (Cochliobolus heterostrophus), rice sesame leaf blight Brown spot (Cochliobolus miyabeanus), garlic leaf blight Tip blight (Pleospora herbarum), barley leaf spot Stripe (Pyrenophora graminea) Net blotch (Pyrenophora teres), sorghum soot disease Leaf blight (Setosphaeria turcica), maize soot disease Northern leaf blight (Setosphaeria turcica), asparagus spotted disease Leaf spot (Stemphylium botryosum), black rot Saba (Venturia carpophila), apple black scab Scab (Venturia Inaequalis), pear scab Scab (Venturia nashicola), cucurbit vine blight Gummy stem blight (Didymella bryoniae), burdock black spot Leaf exigua.
  • Apple brown spot disease Blotch (Diplocarpon mali), rose black spot disease Black spot (Diplocarpon rosae), onion gray rot Gray mold neck rot (Botrytis allii), gray fungus Gray mold, Botrytis blight (Botrytis cinerea), leek white spotted leaf Disease Leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), broad bean red spot disease Chocolate spot (Botrytis cinerea, B. elliptica, B. fabae), Rosaceae's brown rot (Monilinia fructicfr, tigMena enaM. , M.
  • Adzukicola rakkyo dry rot Fusarium basal rot (Fusarium oxysporum allii, F. solani f. sp. radicicola), Stem rot (Fusarium oxysporum f. sp. batatas, F. solani), dry rot of dry potato Dry rot (Fusarium oxysporum f. sp. colocasiae), cabbage Yellow wilt of Komatsuna Yellows (Fusarium oxysporum f. Sp. Conglutinans), Panama disease (Fusarium ⁇ ⁇ ⁇ oxysporum f. Sp. Cubense), Fusarium ⁇ wilt (Fusarium oxysporum f. Sp.
  • Fragaria) rot (Fusari um oxysporum f. sp. lactucae), watermelon vine split disease Fusarium wilt (Fusarium oxysporum f. sp. lagenariae, F. o. f. sp. niveum), tomato wilt Fusarium wilt (Fusarium oxysporum f.cospoilcoly) Melon vine split disease Fusarium wilt (Fusarium oxysporum f. Sp. Melonis), Japanese radish yellow yellow (Fusarium oxysporum f. Sp. Raphani), spinach wilt Fusarium wilt (Fusarium oxysporum f. Spina)
  • Rice banana seedling disease “Bakanae” disease (Gibberella fujikuroi), Japanese vertebrate black spot disease Verticilliumpotblack spot (Verticillium albo-atrum, V. dahliae), tomato, eggplant, Japanese cypress Verticillium wilt (Verticillium dahliae) Strains of Blight Ceratocystis canker (Ceratocystis ficicola), Black potato black spot rot (Ceratocystis fimbriata), Spotted ring blight Gray blight (Pestalotiopsis longiseta, P.
  • Chestnut blight Endothia canker (Cryphonectria parasitica Melanose (Diaporthe citri), Asparagus stem blight Stem blight (Phomopsis asparagi), pear blight Phomopsis canker (Phomopsis fukushii), eggplant brown rot, Brown spot (Phomopsis vexans), tea anthracnose Anthracnose (Discula theae-sin , Apple rot Valsa canker (Valsa ceratosperma), rice blast Blast (Magnaporthe grisea), strawberry anthracnose CrownCrrot (Colletotric hum acutatum, C.
  • Fig rust Rust (Phakopsora nishidana), soybean rust Rust (Phakopsorachypachyrhizi), rose rust Rust (Kuehneolanejaponica, hPhragmidiumragfusiforme, P. mucronatum, cronP.
  • Rosae-multiflorae Rosae-multiflorae
  • pear Red Star Rust Gamnosporangiumdayamadae
  • Rust of Rubiaceae Rust Puccinia allii
  • Chrysanthemum Rust Puccinia horiana
  • Wheat Red Rust BrownBrrust Puccinia recondita
  • Chrysanthemum Rust Puccinia tanaceti var.tanaceti
  • Broad bean rust Rust Uromyces viciae-fabae var.
  • Rhizopus rot Rhizopus stolonifer var. Stolonifer
  • Clubroot Pierroot
  • Sugar beet root disease Aphanomyces root rot (Aphanomyces cochlioides), white rust (Albugo macrospora) of Brassicaceae, lettuce downy mildew (Bremia lactucae), downy mildew (Peronospora chrysanthemi-coronarii), onion, Downy mildew (Peronospora destructor), spinach downy mildew (Peronospora farinosa f. Sp.
  • Tomato Scab Bacterial canker (Clavibacter michiganensis subsp. Michiganensis), Potato Scab Scab (Streptomyces spp.), Crown gall (Rhizobium radiobacter), sorghum streak bacterial disease Bacterial stripe (Burkholderia andropogonis), onion rot Soft rot (Burkholderia cepacia, Pseudomonas marginalis pv. Marginalis, Erwinia rhapontici), rice blast Bacterial grain rot (Burkholderia gladioli, B. glumae), Bacterial fruit blotch (Acidovorax avenae subsp.
  • Bacterial leaf blight (Acidovorax konjaci), Bacterial wilt (Ralrumonia soace) , Bacterial shot hole (Xanthomonas arboricola pv. Pruni, Pseudomonas syringae pv. Syringae, Brenneria nigrifluens), peach black spot Bacterial leaf spot (Xanthomonas arboricola pv. Pruni) vitians), cruciferous black rot (Xanthomonas campestris pv. campestris), soybean leaf burning Bacterial pustule (Xanthomonas ca mpestris pv.
  • Bacterial canker Pseudomonas syringae pv. actinidiae
  • loquat cancer canker Pseudomonas syringae pv. eriobotryae
  • Bacterial spot Pseudomonas syringae pv.
  • leek soft rot Bacterial soft rot (Dickeya sp., Pectobacterium carotovorum), Rosaceae Fire blight (Erwinia amylovora), konjac rot Soft rot (Pectobacterium carotovorum), soft rot Bacterial soft rot (Pectobacterium carotovorum).
  • Animal infections Pneumocystis pneumonia (Pneumocystis jirovecii), Candidiasis (Candida albicans), Aspergillosis (Aspergillus fumigatus), Trichophytosis (Microsporum canis, M. gypseum, T. phytorum. verrucosum), Histoplasmosis (Histoplasma capsulatum), Cryptococcosis (Cryptococcus neoformans).
  • parasite means a plant parasitic linear animal parasitic on a plant, an animal parasitic linear animal parasitic on an animal, a bald animal, a flat animal, a protozoan, and the like.
  • the following parasites can be mentioned, but specific examples of the parasites are not limited to these.
  • Giant kidney worm (Dioctophyma renale), ringed capillary worm Thread worms (Capillaria annulata), torsion capillary nematode Cropworm (Capillaria contorta), liver capillary nematode Capillary liver worm (Capillaria hepatica), penetrating capillary nematode (Capillaria) perforans), Philippine Capillaria philippinensis, Capillaria suis, Caterpillar Whipworm (Trichuris discolor), Whipworm Whipworm (Trichuris ovis), Pig whipworm Pig Whipworm (Trichuris suis), human Enoplida nematodes such as the whipworm Human whipworm (Trichuris trichiura), the dog whipworm Dog whipworm (Trichuris vulpis), and the Trichinella pork worm (Trichinella spiralis).
  • Nipple worm Nematode Intestinal threadworm (Strongyloides papillosus), Cat feline worm (Strongyloides planiceps), Pig worm nematode Pig threadworm (Strongyloides ransomi), Human dung beetle Threadworm (Strongyloides stercoralis), Micronema spp. Rhabditida nematode.
  • Rice white nematode (Aphelenchoides besseyi), strawberry nematode, Strawberry foliar nematode (Aphelenchoides fragariae), chrysanthemum foliar nematode (Aphelenchoides ritzemabosi), pine wood nematode (Bineurus) Aphelenchida) Nematode.
  • Potato cyst nematode (Globodera pallida), Potato cyst nematode (Globodera rostochiensis), Wheat cyst nematode (Heterodera avenae), Soybean cyst nematode cyst nematode (Heterodera schachtii), clover cyst nematode Clover cyst nematode (Heterodera trifolii), arenaria root nematode Peanut root-knot nematode (Meloidogyne arenaria), red root nematode Northern root-knot nematode (Meloidogyne incognita), Java root-knot nematode (Meloidogyne javanica), Apple root-knot nematode (Meloidogyne mali), Southern nematode sale nematode Cof fee root-lesion nematode (Pratylenchus coffeae), sawt
  • Oxyurida nematodes such as human worm Pinworm (Enterobius vermicularis), horse worm Equine pinworm (Oxyuris equi), rabbit worm Rabbit pinworm (Passalurus ambiguus), Pig roundworm (Ascaris suum), Horse roundworm Horse roundworm (Parascaris equorum), Dog roundworm Dog roundworm (Toxascaris leonina), Dog roundworm Dog intestinal roundworm (Toxocara canis), Cat roundworm Feline roundworm (Toxocara cati), Cattle roundworm Large cattle roundworm (Toxocara vitulorum), Anisakis spp., Pseudoterranova spp., chicken caecal caecal worm (Heterakis gallinarum), chicken roundworm (Ascaridia galli) and other roundworms (Ascaridida) Nematode.
  • human worm Pinworm Enterobius vermicularis
  • Horse worm Equine pinworm Oxyuris
  • Medinaworm Guinea worm (Dracunculus medinensis), Dolores jaw-and-mouth beetle (Gnathostoma doloresi), Ganthostoma hispidum, Japanese jaw-and-mouth beetle (Gnathostoma nipponicum), Reddish-coloured worm (Gnathostoma spinigerum) Dog stomach worm (Physaloptera canis), cat stomach worm (Physaloptera felidis, P.
  • Craniopods such as Moniliformis moniliformis and Giant thorny-headed worm (Macracanthorhynchus hirudinaceus). Artificial leaves such as Fish tapeworm (Diphyllobothrium latum), Diphyllobothrium nihonkaiense, Manson tapeworm (Spirometra erinaceieuropaei), Diplogonoporus grandis Eye (Pseudophyllidea) tapeworm.
  • Wire worms (Mesocestoides lineatus), striped worms Chicken tapeworm (Raillietina cesticillus), spiny cleft worm Fowl tapeworm (Raillietina echinobothrida), square tapeworm Chicken tapeworm (Raillietina tetragona), canine tapeworm (Taenia hydatigena), Canine tapeworm (Taenia multiceps), sheep worm Sheep measles (Taenia ovis), beetle tapeworm Dog tapeworm (Taenia pisiformis), striped beetle Beef tapeworm (Taenia saginata), striped worm Tapeworm (Taenia serialis) ), Rodentworm Pork tapeworm (Taenia solium), caterpillar Feline tapeworm (Taenia taeniaeformis), single tapeworm Hydatid tapeworm (Echinococcus granulosus), multi-budworm, small fox tape
  • Stripeidida such as Pharyngostomum cordatum, Blood fluke (Schistosoma haematobium), Blood fluke (Schistosoma japonicum), and Schistosoma mansoni.
  • Echinostoma cinetorchis Echinostoma hortense, Giant liver fluke (Fasciola gigantica), Liver common liver fluke (Fasciola hepatica), Fasciolopsis buski, Flat belly twin Echinostomida flukes such as Homalogaster paloniae.
  • Amphimerus spp. Liver fluke Chinese liver fluke (Clonorchis sinensis), Cat liver fluke Cat liver fluke (Opisthorchis felineus), Thai liver fluke Southeast Aasian liver fluke (Opisthorchis viverrini), Pseudamphistom spp .), Metrochis spp., Parametorchis spp., Malformed fluke (Heterophyes heterophyes), Metagonimus yokokawai, foregut fluke (Pygidiopsis summa), etc. Opisthorchiida). Amoeba such as Entamoeba histolytica (E. invadens).
  • Futago Babesia (Babesia bigemina), Cattle Babesia bovis, Big Horse Babesia caballi, Dog Babesia canis, Cat Babesia felis, Gibson dog Babesia gibsoni, Large Piroplasma (Babesia ovata) ), Cytauxzoon felis, tropical piroplasmosis Tyleria (Theileria annulata), pseudocoastal fever Tyreria (Theileria mutans), small piroplasma (Theileria orientalis), east coast fever Tyrelia (Theileria parva), etc. Piroplasmida sporozoites.
  • Haemoproteus mansoni chicken leucocytozone (Leucocytozoon caulleryi), Plasmodium falciparum, Plasmodium malariae, Plasmodium ovale, Plasmodium ovale Haemosporida spores such as protozoa (Plasmodium vivax).
  • cidiorida Vestibuliferida ciliates such as large colonic barantidium coli.
  • Trichomonadida flagellates such as Histomonas meleagridis, Pentatrichomonas hominis, Trichomonas tenax.
  • Vaccinonadida flagellates such as Giardia intestinalis, Giardia muris, turkey hexamita (Hexamita meleagridis), Hexamita parva.
  • Leishmania donovani Leishmania infantum, Leishmania major, Leishmania tropica
  • Trypanosoma brucei gambiense Trypanosoma brucei cruise
  • Trypanosoma brucei rhodesi Kinetoplastid flagellates such as Trypanosoma cruzi, Trypanosoma equiperdum, and Trypanosoma evansi.
  • Plant in this specification refers to cereals and fruit trees / vegetables cultivated as human food, feed crops such as livestock and poultry, appreciation plants that love their form and shape, or planting in parks, streets, etc. It means a vascular plant (Tracheophyta), and specific examples include the following plants, but specific examples of plants are not limited to these.
  • Pinaceae plants belonging to Pinaceae such as Japanese red pine (Pinus densiflora), European red pine Scots Pine (Pinus sylvestris), Japanese black pine (Pinus thunbergii).
  • Pepper (Piper nigrum) such as Pepperaceae (Piperaceae), Avocado Avocado (Persea americana) and other magnoliaceae (Lauraceae) etc., magnoliids, Konjac (Amorphophallus konjac), taro edode (Colocasia esculenta) and other taro (Araceae), Chinese yam (Dioscorea batatas), yam Japanese yam (Dioscorea japonica) and other yam (Dioscoreacesum var) porrum), Onion Onion (Allium cepa), Rakkyo Rakkyo (Allium chinense), Leek Welsh onion (Allium fistulosum), Garlic Garlic (Allium sativum), Chives Chives (Allium schoenoprasum), Asatsuchi Chive (Allium schoenofosum var) Japanese leek Oriental garlic (Allium tuberosum), Allium
  • Lotus root such as Lotus root (Nelumbo nucifera) (Nelumbonaceae), groundnut Peanut (Arachis hypogaea), chickpea Chickpea (Cicer arietinum), lentil Lentil (Lens culinaris), pea Pea (Pisum sativum) , Soybean Soybean (Glycine max), common bean Common bean (Phaseolus vulgaris), adzuki bean (Vigna angularis) adzuki bean, cowpea (Vigna unguiculata), legaceae (Fabaceae), aceae such as Hop Hop (Humulus lupulus) ), Fig Fig Tree (Ficus carica), Mulberry (Moraceae) such as Mulberry (Morus spp.), Mameaceae (Rhamnaceae) such as jujuba (Rhamnaceae), Strawberry Strawberry (Fragaria), Rose Rose (Rosa) s
  • Chestnuts such as Japanese Chestnut (Castanea crenata), Beechaceae (Fagaceae), Walnut Walnut (Juglans spp.) And other walnuts (Juglandaceae), Cashew nut Cashew (Anacardium occidentale), Mango Mango (Mangifera indica), Pistachio Pistachia (Pistachia) Urushiaceae (Anacardiaceae), salamander Japanese pepper (Zanthoxylum piperitum), etc.
  • Brassica rapeseed Brassica napus
  • Cauliflower Cauliflower Brassica oleracea var. Botrytis
  • Cabbage Cabbage Brassica oleracea var. , Chingen rhino Green pak choi (Brassica rapa var. Chinensis), Nozawana (Brassica rapa var. Hakabura)
  • Brassica Napa cabbage Brassica rapa var. Nippo-oleifera
  • Mizuna Potherb Mustard Varassica nipa (Brassica rapa var. Pekinensis)
  • Papaya (Carica papaya) and other papayas (Caricaceae), okra Okra (Abelmoschus esculentus), cotton Cotton plant (Gossypium spp.), Cacao Cacao (Theobroma cacao) and other mallows (Malvaceae), grapes Grape (Vitis spp. Vitaceae, etc.
  • Sugar beet Sugar beet (Beta vulgaris ssp. Vulgaris var. Altissima), table beet Table beet (Beta vulgaris ssp. Vulgaris var. Vulgaris), spinach Spinach (Spinacia oleracea), etc.
  • Polygonaceae oyster Kaki Persimmon (Diospyros kaki) and other oysters (Ebenaceae), tea Teaenplant (Camellia sinensis) and other camellia (Theaceae), kiwifruit Kiwifruit (Actinidia deliciosa, A.
  • chinensis Actinidiaceae, Blueberry (Vaccinium spp.), Cranberry Cranberry (Vaccinium spp.) And other azaleas (Ericaceae), Coffee tree Coffee ⁇ plants (Coffea spp.) And other Akaneidae (Rubiaceae), Lemon balm Lemon balm (Melissa officinalis), Mint Mint (Mentha spp.), Basil Basil (Ocimum basilicum), Perilla Shiso (Perilla frutescens var. crispa) ), Sesame (Perilla frutescens var.
  • Frutescens Sage Common Sage (Salvia officinalis), Thyme (Thymus spp.), Lamiaceae, Sesame Sesame (Sesamum indicum), etc.
  • Oleaceae such as (Olea europaea), convolvulaceae such as Sweet potato (Ipomoea batatas), Tomato (Solanum lycopersicum), eggplant Eggplant (Solanum melongena), Potato Potato (Silinum tuberos) pepper (Capsicum annuum), bell pepper Bell pepper (Capsicum annuum var.
  • animal in the present specification means humans, companion animals, pets, livestock, poultry, and vertebrates such as research and laboratory animals. Specific examples include the following animals: However, specific examples of animals are not limited to these.
  • Capuchin such as Tufted capuchin (Cebus apella), Crab-eating macaque (Macaca fascicularis), Rhesus macaque (Macaca mulatta), etc.
  • Homo sapiens such as Hominidae, European rabbit (Oryctolagus cuniculus) such as Rabidae (Leporidae), Chinchilla Long-tailed chinchilla (Chinchilla lanigera), Chinchillaidae, Guinea pig Guinea pig (Cavia porcellus) ) Guinea pigs (Caviidae), Golden hamster (Mesocricetus auratus), Dungarian hamster (Phodopus sungorus), Mongolian rat The house mouse ouse (Mus musculus), black rats (Rattus rattus) and other murines (Muridae), chipmunk (Samiuridae) such as Chipmunk (Tamias sibiricus), Dromedary (Camelus dromedarius), Bactrian actl (Camelus) Alpaca (Vicugna pacos), Camelidae such as Llama (L
  • Cats such as Cat (Felis silvestris catus) (Felidae), Dogs (Canis lupus familiaris), Dogs such as Red Fox (Vulpes vulpes), Canidae, -European mink (Mustela lutreola), American mink (Mustela vison), Ferret (Mustela putorius furo) etc.
  • Weasel (Mustelidae), Donkey (Equus asinus), Horse Horse (Equus caballus), etc. Equidae), mammals belonging to the kangaroo family (Macropodidae) such as red kangaroo (Macropus rufus).
  • Veiled chameleon (Chamaeleo calyptratus), etc.
  • Chameleonidae (Chamaeleonidae), Green iguana Green iguana (Iguana iguana), Green anole Carolinaa anole (Anolis carolinensis), etc.
  • Iguanidae Nile monitor Lizards such as the Lizard Lizard Water ⁇ monitor (Varanus salvator), etc.
  • Constrictor (Boa constrictor), etc.
  • Boidae (Boidae), Indian python Indian python (Python molurus), Japanese snake Reticulated python (Python reticulatus), etc.
  • Carp (Cyprinus carpio), Goldfish (Carassius auratus auratus), Zebrafish Zebrafish (Danio rerio), etc.
  • piranha Pieris Archasus tshawytscha
  • Atlantic salmon Atlantic Salmon (Salmo) salar)
  • Brown trout Brown trout (Salmo trutta) salmonid (Salmonidae)
  • Pseudanthias squamipinnis Que Longtooth grouper (Epinephelus bruneus), Mahata ConvictCongrouper (Epinephelus septemfasciatus), etc.
  • Greater amberjack (Seriola dumerili), Yellowtail amberjack (Seriola quinqueradiata), etc. Carangidae, Red sea bream (Pagrus major), etc., Thai family (Sparidae), Nile tilapia Nile tilapia (Oreochromis niloticus), Scalare Cichlidae (Cichlidae) such as Angelfish (Pterophyllum ⁇ scalare), Sababridae (Scombridae) such as Pacific Bluefin unatuna (Thunnus orientalis), Bonefish (Tetraodontidae) such as Japanese pufferfish (Takifugu rubripes) Actinopterygii).
  • useful insects in the present specification means insects that are useful for human life by using their products, or for improving the efficiency of agricultural work such as use for pollination of fruit trees and vegetables.
  • Japanese bee Japanese honeybee (Apis cerana japonica), Western bee Western honey bee (Apis mellifera), Bumblebee Bumblebee (Bombus consobrinus wittenburgi, B. diversus diversus, B. hypocrita terporis, B. hypocrita (Osmia cornifrons), silkworm Silkworm (Bombyx ⁇ mori), and the like, but specific examples of useful insects are not limited thereto.
  • natural enemy means an organism that kills or suppresses the growth of a specific species of organisms, particularly a specific species that harms agricultural crops, by predation or parasitism. The following organisms are listed, but specific examples of natural enemies are not limited to these.
  • the compound of the present invention represented by the formula (I) can be produced, for example, by the following method. Manufacturing method A Formula (II) [wherein Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent the same meaning as described above. Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate, etc.) and formula (III) [wherein G 1 has the same meaning as described above.
  • J 1 is a chlorine atom, bromine atom, C 1 -C 4 alkylcarbonyloxy (eg pivaloyloxy), C 1 -C 4 alkoxycarbonyloxy (eg isobutyloxycarbonyloxy) or azolyl (eg imidazol-1- Il).
  • J 2 represents chlorine atom, bromine atom, iodine atom, C 1 -C 4 alkylcarbonyloxy (eg, pivaloyloxy), C 1 -C 4 alkyl sulfonate (eg, methanesulfonyloxy), C Good elimination of 1 to C 4 haloalkyl sulfonates (eg trifluoromethanesulfonyloxy etc.), aryl sulfonates (eg benzenesulfonyloxy, p-toluenesulfonyloxy etc.) or azolyls (eg imidazol-1-yl etc.) Represents a group.
  • the compound represented by formula (Ia) is used if necessary using a polar solvent such as tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile or N, N-dimethylformamide.
  • a polar solvent such as tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile or N, N-dimethylformamide.
  • a base such as 1 to 3 equivalents of sodium hydride, potassium tert-butoxide, potassium hydroxide, potassium carbonate, triethylamine or pyridine, 10 to 24 minutes in a temperature range of 0 to 90 ° C.
  • This invention compound represented by this can be obtained.
  • Some of the compounds represented by the formula (V) used here are, for example, International Patent Application Publication (WO 2014/177582 Publication), International Patent Application Publication (WO 2015/003951 Publication), International Patent Application Publication ( WO 2015/004091 Publication), International Patent Application Publication (WO 2015/007626 Publication), International Patent Application Publication (WO 2015/078800 Publication) and the like, and other compounds are also known compounds It can be synthesized in the same manner.
  • Some of the compounds represented by the formulas (VIa) and (VIb) are known compounds, and some of them are available as commercial products.
  • other compounds can be synthesized according to a general synthesis method described in literatures concerning known compounds.
  • reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, concentrated after washing with water, or poured into ice water, followed by normal post-treatment such as extraction after organic solvent extraction. Can be obtained. Moreover, when the necessity for purification arises, it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatographic fractionation and the like.
  • the compound represented by the formula (II) used in the production method A can be synthesized, for example, as shown in the reaction formulas 1 and 2.
  • Reaction formula 1 Formula (VII) [wherein Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 , R 5 and J 3 represent the same meaning as described above.
  • the compound represented by the formula (VIa) [wherein R 6 represents the same meaning as described above, using the same reaction conditions as in Production Method C.
  • Reaction formula 2 In the production intermediate represented by the formula (VIII) of the reaction formula 1, the formula (VIIIa) wherein R 6 is trimethylsilyl [wherein Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 and R 5 represents the same meaning as described above. ],
  • fluoride such as tetrabutylammonium fluoride according to the method described in Bioorganic and Medicinal Chemistry [Bioorg. Med. Chem.] 2004, Vol. 12, p.
  • a base such as potassium carbonate
  • Formula (VIIIb) [wherein Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 and R 5 represent the same meaning as described above. ]
  • the compound represented by the formula (VIIIb) is prepared by a general Sonogashira coupling described in, for example, Journal of Organometallic Chemistry [J. Organomet. Chem.] 2006, Vol. Using reaction conditions, formula (IX) [wherein R 6 represents phenyl substituted by (Z) m and an aromatic heterocycle represented by D-1 to D-53, and J 3 is the same as defined above. Represents meaning. And a compound represented by formula (VIII) [wherein Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 represent the same meaning as described above]. . ] Can be synthesized.
  • compounds represented by the formula (VIIIa) may be synthesized by, for example, ACS Med. Chem. Lett. 2012, Vol. 3, 544, Organic and Biomolecular Chemistry [Org Biomol. Chem.] According to the method described in 2015, Vol. 13, page 10852, etc., for example, in the presence of tetrabutylammonium fluoride, etc.
  • the compound represented by the formula (VIII) can also be directly synthesized by reacting with the compound.
  • the compound represented by Formula (VII) used in Reaction Formula 1 can be synthesized, for example, as shown in Reaction Formula 3 to Reaction Formula 15.
  • Reaction formula 3 Formula (X) [wherein Y 1 , Y 2 and J 3 represent the same meaning as described above.
  • a compound represented by formula (XI) [wherein R 3 represents the same meaning as described above.
  • Formula (XII) [wherein Y 1 , Y 2 , R 3 and J 3 represent the same meaning as described above. ] Can be synthesized.
  • the compound represented by the formula (XII) is converted into borohydride according to the method described in, for example, The Journal of Organic Chemistry [J. Org. Chem.] 1985, 50, 133.
  • the compound represented by the formula (XIV) can also be directly synthesized by performing borane reduction in the presence of sodium.
  • the compound represented by the formula (XIV) thus obtained is described in, for example, Bioorganic and Medicinal Chemistry Letters [Bioorg. Med. Chem. Lett.] 2010, 20, 5822
  • R 1 , R 2 , R 4 and R 5 are hydrogen atoms in the formula (VIIa) [wherein Y 1 , Y 2 , R 3 and J 3 represent the same meaning as described above.
  • the compound represented by this can be obtained.
  • Some of the compounds represented by the formula (X) used here are known compounds, and some of them are available as commercial products.
  • other compounds can be synthesized according to a general synthesis method described in literatures concerning known compounds.
  • Reaction formula 4 Formula (XII) of Reaction Formula 3 [wherein Y 1 , Y 2 , R 3 and J 3 represent the same meaning as described above. ] Is subjected to iron reduction in accordance with, for example, the method described in International Patent Application Publication (WO 2008/052733) and the like, thereby obtaining a compound of formula (XV) [wherein Y 1 , Y 2 , R 3 and J 3 represent the same meaning as above. ] Can be synthesized.
  • Reaction formula 5 Formula (XV) of Reaction Formula 4 [wherein Y 1 , Y 2 , R 3 and J 3 represent the same meaning as described above. Embedded image wherein R 1 is substituted by C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, phenyl (C 1 -C 4 ) alkyl, (Z) m Represented by phenyl (C 1 -C 4 ) alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl and the like.
  • the compound represented by the formula (XIX) [wherein Y 1 is represented by the formula (XIX) [wherein Y 1 , Y 2 , R 1 , R 3 and J 3 represent the same meaning as described above. ] Can be synthesized.
  • the compound represented by the formula (XIX) is converted into a compound such as sodium cyanoborohydride in the presence of an amine source such as ammonium acetate in accordance with the method described in, for example, International Patent Application Publication (WO 2011/124093).
  • a reducing agent of formula (XX) [wherein Y 1 , Y 2 , R 1 , R 3 and J 3 represent the same meaning as described above. ] Can be synthesized.
  • Reaction formula 6 Formula (XII) of Reaction Formula 3 [wherein Y 1 , Y 2 , R 3 and J 3 represent the same meaning as described above. And a synthetic intermediate represented by the formula (XXI) [wherein W represents an oxygen atom, a sulfur atom or —NHO—, and R a represents C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, (Z) m substituted with phenyl (C 1 -C 4 ) alkyl and the like.
  • W represents an oxygen atom, a sulfur atom or —NHO—
  • R a represents C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, (Z) m substituted with phenyl (C 1 -C 4 ) alkyl and the
  • Reaction formula 7 Formula (XXIV) [wherein Y 1 , Y 2 , R 3 and J 3 represent the same meaning as described above. ], For example, the method of reacting with chlorine according to the method described in The Journal of Organic Chemistry [J. Org. Chem.] 1982, 47, 2795, etc. Hemi International Edition [Angew. Chem. Int. Ed.] 2009, 48, 154, etc., by halogenation using a method of reacting with bromine according to the method, etc.
  • XXV) [wherein Y 1 , Y 2 , R 3 and J 3 represent the same meaning as described above, and J 4 represents a chlorine atom, a bromine atom or the like.
  • the compound represented by this can be obtained.
  • Some of the compounds represented by the formula (XXIV) used here are known compounds, and some of them are available as commercial products.
  • other compounds can be synthesized according to a general synthesis method described in literatures concerning known compounds.
  • Reaction formula 8 Formula (XXVII) of Reaction Formula 7 [wherein Y 1 , Y 2 , R 3 and J 3 represent the same meaning as described above. ],
  • R 1 and R 2 represent a fluorine atom
  • R 4 and R 5 are hydrogen atoms.
  • Y 1 , Y 2 , R 3 and J 3 represent the same meaning as described above. The compound represented by this can be obtained.
  • Reaction formula 9 Formula (XXVII) of Reaction Formula 7 [wherein Y 1 , Y 2 , R 3 and J 3 represent the same meaning as described above. ],
  • R 1 represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, etc.
  • J 5 represents a chlorine atom, bromine atom or iodine atom.
  • the compound represented by the formula (XXXII) is converted into the formula (XXXIII) [wherein R 3 represents a compound according to the method described in, for example, Tetrahedron Lett. 1989, Vol. 30, page 3561. C 1 -C 6 alkyl and the like, and J 5 represents the same meaning as described above. Or a formula (XXXIV) [formula according to the method described in Helv. Chim. Acta 2002, Vol. 85, page 1850, etc. In the formula, R 3 represents C 1 -C 6 alkyl or the like.
  • R 4 and R 5 are hydrogen atoms in the formula (VII) [wherein Y 1 , Y 2 , R 1 , R 2 , R 3 and J 3 have the same meaning as above] Represents.
  • the compound represented by this can be obtained.
  • Some of the compounds represented by the formula (XXXI) used here are known compounds, and some of them are available as commercial products.
  • other compounds can be synthesized according to a general synthesis method described in literatures concerning known compounds.
  • Reaction formula 11 Formula (XXXI) [wherein Y 1 , Y 2 and J 3 represent the same meaning as described above, and R 1 and R 2 represent a fluorine atom, or R 1 and R 2 together form ethylene It represents forming a cyclopropyl ring with the carbon atom to which R 1 and R 2 are bonded by forming a chain.
  • R 1 and R 2 represent a fluorine atom, or R 1 and R 2 together form ethylene It represents forming a cyclopropyl ring with the carbon atom to which R 1 and R 2 are bonded by forming a chain.
  • the compound of formula (XXXIII) [wherein R 3 and J 5 represent the same meaning as described above.
  • Reaction formula 12 Formula (XXXIX) [wherein Y 1 , Y 2 and J 3 represent the same meaning as described above, and R b represents C 1 -C 6 alkyl. ],
  • J 5 represents the same meaning as described above.
  • a known Grignard reactant represented by the formula (XLI) [wherein Y 1 , Y 2 and J 3 represent the same meaning as described above. ]
  • XLI a known Grignard reactant represented by the formula (XLI) [wherein Y 1 , Y 2 and J 3 represent the same meaning as described above. ]
  • the compound represented by the formula (XLI) is synthesized with, for example, Bioorganic and Medicinal Chemistry Letters [Bioorg. Med. Chem.
  • Reaction formula 13 Formula (XLV) [wherein Y 1 , Y 2 and J 3 represent the same meaning as described above.
  • titanium (IV) tetraisopropoxide according to the method described in, for example, Chemical Communications [Chem. Commun.] 2001, page 1792, Synthesis 2007, page 131, etc.
  • formula (XLVI) [wherein Y 1 , Y 2 and J 3 represent the same meaning as described above. ] Can be synthesized.
  • the compound represented by the formula (XLVI) thus obtained is reacted with di-tert-butyl dicarbonate according to the method described in, for example, International Patent Application Publication (WO 2003/099276).
  • R 1 , R 2 and R 5 are hydrogen atoms, and together with the carbon atom to which R 3 and R 4 are bonded, a cyclopropyl ring is formed (VIIj) [wherein , Y 1 , Y 2 and J 3 represent the same meaning as described above.
  • the compound represented by this can be obtained.
  • Some of the compounds represented by the formula (XLV) used here are known compounds, and some of them are available as commercial products.
  • other compounds can be synthesized according to a general synthesis method described in literatures concerning known compounds.
  • Reaction formula 14 Formula (XXXI) [wherein Y 1 , Y 2 and J 3 represent the same meaning as described above, R 1 represents a fluorine atom, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, etc., and R 2 represents Represents a hydrogen atom, a fluorine atom, C 1 -C 6 alkyl, or the like, or R 1 and R 2 together form an ethylene chain to form a cyclohexane together with the carbon atom to which R 1 and R 2 are bonded. It represents forming a propyl ring. ], For example, Journal of Medicinal Chemistry [J. Med. Chem.] 2009, 52, 4613, Synth. Commun.
  • Reaction formula 15 Formula (XLVIII) [wherein Y 1 , Y 2 and J 3 represent the same meaning as described above.
  • the compound represented by formula (VII) is reduced using a borane-tetrahydrofuran complex, borane-dimethylsulfide complex or the like in the same manner as in reaction formula 14 and then reacted with di-tert-butyl dicarbonate.
  • R 1 and R 2 are fluorine atoms
  • R 3 , R 4 and R 5 are hydrogen atoms (wherein Y 1 , Y 2 and J 3 represent the same meanings as described above).
  • the compound represented by this can be obtained.
  • the compound represented by the formula (XLVIII) used here can be synthesized, for example, as follows.
  • Reaction formula 16 That is, the known formula (L) [wherein Y 1 and Y 2 represent the same meaning as described above. And a known formula (LI) [wherein R b represents the same meaning as described above, and J 6 represents a bromine atom, an iodine atom, trimethylsilyl, or the like.
  • Formula (LII) [wherein Y 1 , Y 2 and R b represent the same meaning as described above. ] Can be synthesized.
  • the compound represented by the formula (LII) thus obtained was applied to the method described in, for example, The Journal of Organic Chemistry [J. Org. Chem.] 1980, 45, 2883. Accordingly, by reacting with ammonia in a solvent such as methanol or ethanol, in formula (XLVIII), R 1 and R 2 are fluorine atoms, and J 3 is a bromine atom [wherein Y 1 And Y 2 represent the same meaning as described above. The compound represented by this can be obtained.
  • the compound represented by the formula (XLVIIIa) is obtained by, for example, trifluoroacetic anhydride in the presence of a base such as pyridine and triethylamine according to the method described in International Patent Application Publication (WO 2006/017409) and the like.
  • a base such as pyridine and triethylamine
  • each of the production intermediates that will be the raw material compounds of production method A to production method C can be obtained by carrying out ordinary post-treatment.
  • each production intermediate produced by these methods can be used as it is in the subsequent step without isolation and purification.
  • Specific examples of the alkynylphenyl-substituted amide compound represented by the formula (I) included in the present invention that can be produced by using these methods include the following structural formulas [I] -1 to [I] -40. The compound represented by these is mentioned. However, the compounds represented by the structural formulas [I] -1 to [I] -40 are for illustrative purposes, and the alkynylphenyl-substituted amide compounds included in the present invention are limited to these. is not.
  • substituents represented by Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 and R 6 in the structural formulas [I] -1 to [I] -40 are shown.
  • Examples of combinations include the combinations shown in Table 2.
  • the combinations in Table 2 are for illustrative purposes and are Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 and R 6 of the alkynylphenyl-substituted amide compounds included in the present invention.
  • Specific combinations of the substituents represented are not limited to these.
  • Et represents ethyl
  • n-Pr is normal propyl
  • i-Pr and Pr-i are isopropyl
  • c-Pr is cyclopropyl
  • Bu-s is sec- Butyl
  • c-Bu represents cyclobutyl
  • t-Bu and Bu-t represent tert-butyl
  • c-Pen represents cyclopentyl
  • c-Hex represents cyclohexyl
  • Ph represents phenyl
  • T-1 to T-81 each represent the following structure.
  • the compounds of the present invention include plant diseases and mammals (Mammalia) that occur in vascular plants (Tracheophyta) such as pine (Pinales), magnolias, monocots, monocots (eudicots), etc.
  • Pathogens of vertebrate (Vertebrata) infections such as birds (Aves), reptiles (Reptilia), and teleosts (Actinopterygii), plant parasitic or animal parasitic linear animals, bald animals, flat animals, protozoa, etc. Can remove the pests.
  • Plant pests include Ascomycota fungi, Basidiomycota fungi, Chitridiomycota fungi, Blastocladiomycota fungi, Mucoromycotina fungi, Cercozoa fungi Cercozoa Protists, Heteromonyphyta Oomycetes, Actinobacteria gram-positive fungi, Tenericutes gram-positive fungi, Proteobacteria gram-negative fungi and leaf lines Aphelenchida nematodes, Tylenchida nematodes, etc., among which the compounds of the present invention are phytopathogenic fungi belonging to the Ascomycota and Basidiomycota, leaf nematodes It exhibits excellent control effects at low concentrations against plant parasitic nematodes belonging to the order of the nematode.
  • Animal pests include Ascomycota fungi, Basidiomycota fungi, Actinobacteria gram-positive fungi, Firmicutes gram-positive fungi, Tenericutes gram-positive fungi , Proteobacteria gram-negative fungi and Enoplida nematodes, Rhabditida nematodes, Strongylida nematodes, Ascaridida nematodes, rotate nematodes Spirurida nematodes, bald worms, Pseudophyllidea tapeworms, Cyclophyllidea tapeworms, Strigeidida fluke, Echinostomida flute Plasmodium (Plagiorchiida), Opisthorchiida, Amoeba, Piroplasmida, Haemosporida, Eucoccidiorida, Eucoccidiorida , Vestibuliferida ciliates, Tri
  • the compounds of the present invention are also effective against pests that have developed resistance to existing fungicides and nematicides, and further the compounds of the present invention are mammals, fish, crustaceans, natural enemies. It has extremely useful features that have almost no adverse effects on non-target organisms such as species and useful insects.
  • the compound of the present invention When using the compound of the present invention, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, penetrant, spreading agent, thickener, antifreezing agent, binder, anti-caking agent. , Disintegrating agents, antifoaming agents, preservatives and anti-decomposition agents, etc., adding liquid (soluble concentrate), emulsion (emulsifiable concentrate), wettable powder (wettable powder), water solvent (water soluble powder), granulated water Water dispersible granule, water soluble granule, suspension ⁇ concentrate, emulsion ⁇ concentrated ⁇ suspoemulsion, microemulsion, microemulsion, dustable powder ), Granules, tablets, and emulsifiable gels, and can be put to practical use. Further, from the viewpoint of labor saving and safety improvement, the preparations of any of the above dosage forms can be provided by being enclosed in a water-soluble package such as a water-soluble
  • solid carrier examples include quartz, calcite, gypsum, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, glazed clay, porcelain stone, nostirite, and allophane.
  • Natural minerals such as shirasu, kira, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite and diatomaceous earth, for example, calcined clay, perlite, shirasu balloon, vermiculite, attapulgus clay and calcined diatomaceous earth
  • Baked products such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium bicarbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium chloride, such as glucose, fructose , And Sugars such as sugar and lactose, polysaccharides such as starch, powdered cellulose and dextrin, organic materials such as urea, urea derivatives, benzoic acid and benzoic acid salts, such as wood flour, cork flour, corn cobs, walnut shells and Examples include plants such
  • liquid carrier such as xylene, alkyl (C 9 or C 10, etc.) benzene, phenylxylylethane and alkyl (C 1 or C 3, etc.) aromatic hydrocarbons such as naphthalene, machine oil, normal paraffin, isoparaffin and Aliphatic hydrocarbons such as naphthene, mixtures of aromatic and aliphatic hydrocarbons such as kerosene, alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol and benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol Polyhydric alcohols such as polyethylene glycol and polypropylene glycol, propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, Ethers such as pyrene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glyco
  • surfactant examples include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene Ethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol and alkyl
  • Nonionic surfactants such as glycosides, alkyl sulfate esters, alkylbenzene sulfonates, lignin sulfonates, Killsulfosuccinate, naphthalenesulfonate, alkylnaphthalenesulfon
  • the application amount of the compound of the present invention varies depending on the application scene, the application time, the application method, the cultivated crop, etc., but in general, the amount of the active ingredient is suitably about 0.005 to 50 kg per hectare (ha).
  • an effective amount of the compound of the present invention is administered orally together with an additive for formulation (intramuscular, Parenteral administration such as subcutaneous, intravenous, intraperitoneal; transdermal administration such as immersion, spraying, bathing, washing, pouring-on and spotting-on and dusting; nasal administration Can be administered.
  • the compounds of the present invention can also be administered by molded products using strips, plates, bands, collars, ear marks, limb bands, labeling devices and the like. In administration, the compound of the present invention can be in any dosage form suitable for the administration route.
  • Arbitrary forms to be prepared include solid preparations such as powders, granules, wettable powders, pellets, tablets, large pills, capsules, molded products containing active compounds; injection solutions, oral solutions, skin Liquid preparations used above or in body cavities; solution preparations such as pour-on, spot-on, flowable, and emulsion; semi-solid preparations such as ointments and gels.
  • the solid preparation can be used mainly for oral administration or diluted with water for transdermal administration or environmental treatment.
  • Solid preparations can be prepared by adding the active compound, if necessary, with adjuncts, mixing with appropriate excipients, and converting to the desired shape.
  • Suitable excipients include, for example, inorganic substances such as carbonates, bicarbonates, phosphates, aluminum oxides, silicas, clays, and organic substances such as sugars, cellulose, crushed grains, and starches.
  • Injection solutions can be administered intravenously, intramuscularly and subcutaneously. Injection solutions dissolve the active compound in a suitable solvent and, if necessary, solubilizers, acids, bases, buffer salts, antioxidants. And can be prepared by adding additives such as protective agents.
  • Suitable solvents include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils, synthetic oils suitable for injection, and the like.
  • solubilizers include polyvinylpyrrolidone, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.
  • Protecting agents include benzyl alcohol, trichlorobutanol, p-hydroxybenzoate and n-butanol.
  • Oral solutions can be administered directly or diluted. It can be prepared in the same manner as an injectable solution. Flowables, emulsions, etc. can be administered directly or diluted transdermally or by environmental treatment. Solutions for use on the skin can be administered by dripping, spreading, rubbing, spraying, spraying or applying by dipping (dipping, bathing or washing). These solutions can be prepared in the same manner as injection solutions.
  • Drops and drop preparations can be prepared by dissolving, suspending or emulsifying the active ingredient in suitable skin-compatible solvents or solvent mixtures. If necessary, auxiliary agents such as surfactants, colorants, absorption promoting substances, antioxidants, light stabilizers and adhesives may be added.
  • Suitable solvents include water, alkanol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, Methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oil, DMF, liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxy-methylene-1, 3-dioxolane is mentioned.
  • Absorption enhancers include DMSO, isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic esters, triglycerides and fatty alcohols.
  • Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherol.
  • the emulsion can be administered orally, transdermally or as an injection.
  • the active ingredient is dissolved in a hydrophobic phase or a hydrophilic phase, and this is added with a suitable emulsifier, and if necessary, a colorant, an absorption promoting substance, a protective agent, an antioxidant, a light-shielding agent, a thickening substance, etc.
  • a suitable emulsifier and if necessary, a colorant, an absorption promoting substance, a protective agent, an antioxidant, a light-shielding agent, a thickening substance, etc.
  • hydrophobic phase paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, branched chain -Like short chain fatty acid and a saturated fatty acid having a chain length of C 16 to C 18 , isopropyl myristate, isopropyl palmitate, caprylic / capric acid ester of a saturated fatty alcohol having a chain length of C 12 to C 18 , isopropyl stearate Oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cety
  • hydrophilic phase examples include water, propylene glycol, glycerin, and sorbitol.
  • Emulsifiers include nonionic interfaces such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefin acid, sorbitan monostearate, glyceryl monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether, etc.
  • amphoteric surfactants such as disodium N-lauryl- ⁇ -iminodipropionate and lecithin
  • anions such as sodium lauryl sulfate, fatty alcohol sulfate ether, monoethanolamine salt of mono / dialkyl polyglycol orthophosphate
  • cationic surfactants such as cetyltrimethylammonium chloride.
  • adjuvants include carboxymethyl cellulose, methyl cellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, methyl vinyl ether, a copolymer of maleic anhydride, polyethylene glycol, wax, colloidal silica.
  • Semi-solid preparations can be administered by application on the skin or spreading or introduction into body cavities. Gels can be prepared by adding sufficient thickener to a solution prepared as described above for an injectable solution to produce a clear material having an ointment-like consistency.
  • Carplex # 80D 10 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name) After uniformly mixing and pulverizing the above, a small amount of water is added and stirred and mixed, granulated with an extrusion granulator, and dried to obtain a granulated wettable powder.
  • wettable powder preparation Compound No. 1-005 of the present invention 25 parts sodium diisobutylnaphthalenesulfonate 1 part calcium n-dodecylbenzenesulfonate 10 parts alkylaryl polyglycol ether 12 parts naphthalenesulfonic acid formalin condensate Sodium salt 3 parts Emulsion type silicone 1 part Silicon dioxide 3 parts Kaolin 45 parts Formulation Example 10 Preparation of water-soluble thickener Compound No. 1-023 20 parts Polyoxyethylene lauryl ether 3 parts Sodium dioctyl sulfosuccinate 3. 5 parts dimethyl sulfoxide 37 parts 2-propanol 36.5 parts
  • an effective amount of the compound of the present invention can be used alone as an active ingredient. It may be mixed with seed nematicides, insecticides, acaricides, plant growth regulators, herbicides, synergists, fertilizers, soil conditioners, etc. at the time of formulation or spraying.
  • an effective amount of the compound of the present invention can be administered alone as an active ingredient, but other antibacterial agents, It can also be mixed with an anthelmintic agent at the time of preparation or administration.
  • the control spectrum can be expanded by the additive / synergistic action of the mixed agents, Effects such as improvement of pest control effect, reduction of control cost by reducing the amount of applied medicine, and sustained control effect over a longer period can be expected.
  • mixing with other types of fungicides, nematicides, antibacterial agents and anthelmintic agents with different mechanisms of action is an extremely effective control method from the viewpoint of preventing the acquisition of drug resistance by pests. .
  • a combination of a plurality of known fungicides, known nematodes, known insecticides, known acaricides, known antibacterial agents or known anthelmintic agents is also possible.
  • fungicides As the types of fungicides, nematicides, insecticides, acaricides, anthelmintic agents or antibacterial agents used in combination with the compounds of the present invention, for example, The Pesticide Manual 16th edition, 2012, etc. Examples include the compounds described. Specific examples of common names are as follows, but the general names are not necessarily limited to these.
  • Fungicide A: Nucleic acid biosynthesis inhibitors benalaxyl, benalaxyl-M (benalaxyl-M), furaxyl (furalaxyl), metalaxyl, metalaxyl-M, ofurace, oxadixyl, Bupirimate, ethirimol, Hymexazol, B: Mitotic and mitotic inhibitors benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl, Dietofencarb, Ethaboxam, zoxamide, Pencicuron (pencycuron), Fluopicolide, Pyridachlometyl,
  • G sterol biosynthesis inhibitor azaconazole, abitertanol, bromuconazole, cyproconazole, difenoconazole, dinicoazole, dinicoazole-M (diniconazole-M), Epoxiconazole, etaconazole, fenarimol, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, Imazalil, imibenconazole, ipconazole, ipfentrifluconazole, mefentrifluconazole, metconazole (metconazole) azole), microbutanil, nuarimol, oxpoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole (Prothioconazole), pyrifenox, pyrisoxazole, simeconazole, tebucon
  • H cell wall synthesis inhibitor validamycin, Polyoxins, polyoxins-D (polyoxorim), Benthiavalicarb-isopropyl, dimethomorph, flumorph, iprovalicarb, mandipropamid, pyrimorph, valifenalate,
  • I Melanin synthesis inhibitor phthalide, pyroquilon, tricyclazole, Carpropamid, diclocymet, fenoxanil, Tolprocarb,
  • P plant resistance inducer acibenzolar-S-methyl, Diclobentiazox, probenazole, Isotianil, tiadinil, Laminarin,
  • M drugs with multiple action points Bordeaux mixture, cheshunt mixture, basic carbonate, copper carbonate, copper hydroxide, copper naphthenate , Copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, oxine copper, lime sulfur polysulfide, sulfur, amobam, ferbam, mancozeb, maneb, maneb, metiram, polycarbamate, propineb, thiram, ziram (Ziram), captan, folpet, chlorothalonil, dichlofluanid, torruf Enid (tolylfluanid), guazatine (guazatine), iminoctadine - Arubeshiru salt (iminoctadine-albesilate), iminoctadine acetate (iminoctadine-triacetate), Anirajin (anilazine), dithianon (dithianon), Kinomechioneto (chinomethionat), Furu
  • Insecticides and acaricides A: Acetylcholinesterase (AChE) inhibitor Alanicarb, aldicarb, bendiocarb, benfuracarb, butofcarboxim, carbaryl, carbofuran, carbofuran Fan (carbosulfan), ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, pirimicarb, thiodicarb Thiofanox, triazamate, Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos ( chlorpyrifos, chlorpyrifos-methyl, cyanophos, diazinon, dichlorvos, dimethoate, dimethylvinphos, disulfoton, EPN, fenitro
  • GABAergic chloride channel antagonist GABAergic chloride channel antagonist, endosulfan, alpha-endosulfan, Ethiprole, fipronil, flufiprole, pyriprole, Afoxolaner, fluralaner, fluxametamide, lotilaner, sarolaner, tigolaner,
  • C Sodium channel modulators acrinathrin, allethrin, benfluthrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, chloropralethrin ), Cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin ), Alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin Empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucytrinate, flumethrin, fluvalinate, Tau-fluvalinate, halfenprox, heptaflu
  • D Nicotinic acetylcholine receptor (nAChR) agonists acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, thiamethoxam Sulfoxaflor, Flupyradifurone, Fluprimin, Dicloromezotiaz, triflumezopyrim, E; nicotinic acetylcholine receptor (nAChR) allosteric modulators spinetoram, spinosad, F: glutamatergic chloride channel activator abamectin, emamectin-benzoate, lepimectin, milbemectin, G; juvenile hormone analog mesoprene, Phenoxycarb, Pyriproxyfen,
  • H Hemiptera selective feeding inhibitor pymetrozine, Flonicamid, I: mite growth inhibitor clofentezine, hexythiazox, Etoxazole, J: Microbial-derived insect midgut mesentery bacillus thuringiensis (bacillus thuringiensis, subsp.israelensis, subsp.aizawai, subsp.kurstaki, subsp.tenebrionis, etc.) K; mitochondrial ATP synthase inhibitor diafenthiuron, Azocyclotin, fenbutatin oxide, Propargite, L: oxidative phosphorylation uncoupler, chlorfenapyr, M; nicotinic acetylcholine receptor (nAChR) channel blocker bensultap, cartap, thiocyclam,
  • nAChR nicotinic acetylcholine receptor
  • N chitin biosynthesis inhibitor (type 0) Bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron ), Nobifluuron, teflubenzuron, triflumuron,
  • O Chitin biosynthesis inhibitor (type 1) Buprofezin, P: molting inhibitor (fly insect) Cyromazine, Q: molting hormone (ecdysone) receptor agonist chromafenozide, halofenozide, methoxyfenozide, tebufenozide, R; octopamine receptor agonist amitraz,
  • W Mitochondrial electron transport system complex II inhibitor cyenopyrafen, cyflumetofen, Piflubumide
  • X Ryanodine receptor modulator chlorantraniliprole, cyantraniliprole, cyclaniliprole, cyhalodiamide, flubendiamide, tetraniliprole, UN: unknown mechanism of action and other drugs azadirachtin, benzoximate, bifenazate, bromopropylate, dicohol, pyridalyl, pyrifluquinazon, Acynonapyr, afidopyropen, benzpyrimoxan, broflanilide, flometoquin, fluhexafon, oxazosulfyl, ticazopyrazol and tyclopyrazoflor (Exam name).
  • Nematicides A: Acetylcholinesterase (AChE) inhibitor Oxamyl, Cadusafos, dichlofenthion, ethoprophos, fenamiphos, fosthiazate, fosthietan, imcyafos, isamifos, isazofos, isazofos And UN; unknown mechanism of action and other drugs fluazaindolizine, fluensulfone, methyl bromide, methyl isothiocyanate, sodium azide and thioxazaphene (Tioxazafen) etc.
  • AChE Acetylcholinesterase
  • Anthelmintic A: Acetylcholinesterase (AChE) inhibitor propoxur, Coumaphos, propetamphos, B; nicotinic acetylcholine receptor (nAChR) antagonist monepantel, C: GABAergic chloride channel agonist piperazine adipate, piperazine citrate, piperazine phosphate, D: glutamatergic chloride channel activator doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin,
  • E Latrophylline receptor agonist emodepside
  • F Depolarizing neuromuscular blocking agent Morantel tartrate, oxantel pamoate, oxantel tartrate, pyrantel pamoate
  • G oxidative phosphorylation uncoupler bromofenofos, closantel
  • H a reduction of fumaric acid and an oxidation inhibitor of succinic acid, levamisole
  • I Nucleic acid biosynthesis inhibitor sulfadimethoxine, sulfadoxine, sulfamerazine, sulfamonomethoxine, sulfamoildapsone, Pyrimethamine, Furazolidone, Metronidazole, tinidazole,
  • J Mitotic and cell division inhibitors albendazole, cambendazole, febantel, fenbendazole, flubendazole, mebendazole, oxfendazolee ), Oxibendazole, parbendazole, thiabendazole, triclabendazole, And UN; mechanism of action unknown and other drugs bithionol, carnidazole, thiacetalsamide, chloroquine, clazuril, clorsulon, cimiazol, dichlorophen ), Diethylcarbamazine, diminazene, disophenol, dithiazanine iodide, glycalpyramide, imidocarb, mefloquine, melarsomine dihydrochloride ( melarsamine hydrochloride, metyridine, nicarbazin, niclosamide, nitroscanate, nitroxynil, omphalotin, oxyclozide anide,
  • Antifungal agents A: Respiratory inhibitor atovaguone, B: Sterol biosynthesis inhibitor climbazole, clotrimazole, econazole nitrate, itraconazole, ketoconazole, miconazole nitrate, sulconazole nitrate, Tolnaftate, C: oxidative phosphorylation uncoupler pyrrolnitrin, D: Nucleic acid biosynthesis inhibitor flucytosine, E: Cell membrane disrupting agent amphotericin B (amphotericin B), tricomycin (trichomycin), F: Mitosis and cell division inhibitor, griseofulvin, And UN; mechanism of action unknown and other drugs acriflavine, etc.
  • Antibacterial agent A: DNA / RNA synthesis inhibitor octhilinone, B: DNA topoisomerase type II inhibitor miloxacin, oxolinic acid, Danofloxacin, difloxacin, enrofloxacin, lomefloxacin, marbofloxacin, nadifloxacin, norfloxacin, ofloxacin, orloxacin (Orbifloxacin), C: dihydrofolate reductase inhibitor olmethoprim (ormethoprim), trimethoprim (trimethoprim), D: protein synthesis inhibitor chloramphenicol (chloramphenicol), florfenicol (florfenicol), thiamphenicol (thiamphenicol), Erythromycin, Azithromycin, tulathromycin, Josamycin, midcamycin, miramycin, tilmicosin phosphate, acetylisovaleryltylosin acetate, t
  • E Cell wall synthesis inhibitor vancomycin, Fosfomycin (fosfomycyn), Aminopenicillin, amoxicillin, ampicillin, benzylpenicillin, penicillin, piperacillin, Cefaclor, cefalexin, cefalothin, cefapirin, cefazolin, cefdinir, cefdinir, cefixime, cefoperazone, cefquin, cefquin, cefquinome Ceftiofur, Cefmetazole, Flomoxef, latamoxef, Aztreonam, F; ⁇ -lactamase inhibitor clavulanic acid, sulbactam, G: Cell membrane disrupting agent, colistin, H: Nitrification inhibitor nitrapyrin, And UN; unknown mechanism of action and other drugs: bethoxazin, bronopol, dinitrmide, calcined shell calcium (calcium oxide), Talalomyces spp., Tri
  • Step 2 Preparation of 4-bromo-2-chloro-1- (1-methoxy-2-nitropropyl) benzene 4.37 g of 4-bromo-2-chloro-1- (2-nitro-1-propenyl) benzene To a 60 ml solution of toluene, 14.98 g of 28% by mass sodium methoxide methanol solution was added dropwise with stirring under ice-cooling. After completion of the reaction, 20 ml of acetic acid and 80 ml of water were added to the reaction mixture, and the mixture was extracted with ethyl acetate (200 ml ⁇ 1). The solvent was distilled off under.
  • Step 3 Preparation of 2- (4-bromo-2-chlorophenyl) -2-methoxy-1-methylethylamine 5.28 g of 4-bromo-2-chloro-1- (1-methoxy-2-nitropropyl) benzene After dissolving in 20 ml of a methanol-water (1: 1) mixed solvent, 5.50 g of ammonium chloride and 2.87 g of reduced iron were added, and the mixture was stirred at 70 ° C. for 6 hours. After completion of the reaction, the mixture was allowed to cool to room temperature, insoluble materials were removed by Celite filtration, and the solvent was distilled off under reduced pressure.
  • Step 4 Preparation of N- [2- (4-Bromo-2-chlorophenyl) -2-methoxy-1-methylethyl] carbamic acid-tert-butyl 2- (4-Bromo-2-chlorophenyl) -2-methoxy 1-Methylethylamine 4.45 g of ethyl acetate in 12 ml and potassium carbonate in 3.39 g of water in 12 ml were mixed, and at room temperature, 5.23 g of di-tert-butyl dicarbonate was added dropwise. Stirring was continued for another 2 hours at the same temperature.
  • Step 5 Preparation of N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -2-methoxy-1-methylethyl] carbamic acid-tert-butyl N- [2- (4-Bromo- 2-chlorophenyl) -2-methoxy-1-methylethyl] carbamic acid-tert-butyl in 2 ml of N, N-dimethylformamide solution in 4 ml of triethylamine, 873 mg of cyclopropylacetylene, 201 mg of copper (I) iodide and tetrakis 915 mg of (triphenylphosphine) palladium (0) was added, and the mixture was stirred at 90 ° C.
  • Step 6 Preparation of 2- [2-chloro-4- (cyclopropylethynyl) phenyl] -2-methoxy-1-methylethylamine N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl]-
  • 2-methoxy-1-methylethyl] carbamic acid-tert-butyl 840 mg in dichloromethane 3 ml with ice-cooling stirring was added 1 ml of trifluoroacetic acid, and the mixture was stirred at room temperature for 1 hour.
  • Step 7 Preparation of N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -2-methoxy-1-methylethyl] -2- (trifluoromethyl) nicotinamide 2- (Trifluoromethyl ) 145 mg of oxalyl chloride and 10 mg of N, N-dimethylformamide were added to a solution of 94 mg of nicotinic acid in 1 ml of dichloromethane and stirred at room temperature for 1 hour.
  • Step 2 Preparation of N- [2- (4-bromo-2-chlorophenyl) -1-methylethyl] carbamic acid-tert-butyl 2- (4-bromo-2-chlorophenyl) -1-methylethylamine 1.6 g 1.9 g of di-tert-butyl dicarbonate and 874 mg of triethylamine were added to 10 ml of dichloromethane and stirred at room temperature for 16 hours. After completion of the reaction, 20 ml of water was added to the reaction mixture, the organic layer was separated, and the aqueous layer was extracted with chloroform (10 ml ⁇ 1).
  • Step 3 Preparation of N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -1-methylethyl] carbamic acid-tert-butyl N- [2- (4-bromo-2-chlorophenyl) -1-methylethyl] carbamic acid-tert-butyl 1.5 g of N, N-dimethylformamide 3 ml solution, triethylamine 4 ml, cyclopropylacetylene 1.4 g, copper (I) iodide 328 mg and tetrakis (triphenylphosphine) palladium (0) 1.5 g was added and stirred at 100 ° C.
  • Step 4 Preparation of 2- [3-chloro-4- (cyclopropylethynyl) phenyl] -1-methylethylamine N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -1-methylethyl ]
  • carbamate-tert-butyl 410 mg in dichloromethane 5 ml was added 3 ml of trifluoroacetic acid and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was added 10 ml of 10% by weight aqueous potassium carbonate solution, and the mixture was extracted with ethyl acetate (10 ml ⁇ 2).
  • Step 5 Preparation of N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -1-methylethyl] -2- (difluoromethyl) nicotinamide 2- (difluoromethyl) nicotinic acid 55 mg dichloromethane To 1 ml solution, 57 mg of oxalyl chloride and 10 mg of N, N-dimethylformamide were added and stirred at room temperature for 1 hour.
  • reaction mixture was allowed to cool to room temperature, 10 ml of saturated aqueous ammonium chloride solution and 10 ml of ethyl acetate were added, and the mixture was filtered through celite. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (10 ml ⁇ 1). The organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • Step 2 Preparation of 2- [3-chloro-4- (3-furylethynyl) phenyl] -1-methylethylamine N- [2- [2-chloro-4- (3-furylethynyl) phenyl] -1- 1 ml of trifluoroacetic acid was added to 2 ml of a dichloromethane solution of 460 mg of methylethyl] carbamic acid-tert-butyl and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was added 10 ml of 10% by weight aqueous potassium carbonate solution, and the mixture was extracted with ethyl acetate (10 ml ⁇ 2).
  • Step 3 Preparation of 2-chloro-N- [2- [2-chloro-4- (3-furylethynyl) phenyl] -1-methylethyl] nicotinamide 2- [3-chloro-4- (3-furyl) Ethynyl) phenyl] -1-methylethylamine in a solution of 70 mg of N, N-dimethylformamide in 47 ml of 2-chloronicotinic acid, 0.5 ml of triethylamine, 5 mg of N, N-dimethyl-4-aminopyridine and O- (1-benzo Triazolyl) -N, N, N ′, N ′,-tetramethyluronium tetrafluoroborate (112 mg) was added, and the mixture was stirred at room temperature for 16 hours.
  • Step 1 Preparation of N- [2- [2-chloro-4- (trimethylsilylethynyl) phenyl] -1-methylethyl] carbamic acid-tert-butyl N- [2--prepared in Step 2 of Synthesis Example 2 (4-Bromo-2-chlorophenyl) -1-methylethyl] carbamic acid-tert-butyl in a solution of 1.0 g of N, N-dimethylformamide in 3 ml of triethylamine 435 mg, trimethylsilylacetylene 422 mg, copper (I) iodide 109 mg and dichlorobis (Triphenylphosphine) palladium (II) (201 mg) was added, and the mixture was stirred at 100 ° C.
  • Step 2 Preparation of N- [2- [2-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -1-methylethyl] carbamic acid-tert-butyl N- [2- [ 2-Chloro-4- (trimethylsilylethynyl) phenyl] -1-methylethyl] carbamic acid-tert-butyl 450 mg of N, N-dimethylformamide in 2 ml solution of triethylamine 373 mg, 2-fluoro-5-iodopyridine 328 mg, iodide Copper (I) 47 mg, tetrakis (triphenylphosphine) palladium (0) 71 mg and tetrabutylammonium fluoride 1.47 ml were added, and the mixture was stirred at 80 ° C.
  • Step 3 Preparation of 2- [3-Chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -1-methylethylamine N- [2- [2-Chloro-4-[(6- 1 ml of trifluoroacetic acid was added to a solution of 452 mg of fluoropyridin-3-yl) ethynyl] phenyl] -1-methylethyl] carbamic acid-tert-butyl in 2 ml of dichloromethane and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure.
  • Step 4 Preparation of 3-chloro-N- [2- [2-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -1-methylethyl] -2-pyridinecarboxamide 2- [ 3-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -1-methylethylamine in a solution of 100 mg of N, N-dimethylformamide in 1 ml of 44 mg of 3-chloro-2-pyridinecarboxylic acid and 1 ml of triethylamine N, N-dimethyl-4-aminopyridine 5 mg and O- (1-benzotriazolyl) -N, N, N ′, N ′,-tetramethyluronium tetrafluoroborate 107 mg And stirred for 16 hours.
  • Step 1 Preparation of ethyl 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetate 3.20 g of 4-bromo-2-chloro-1-iodobenzene and ethyl bromodifluoroacetate under a nitrogen atmosphere To a 20 g solution of 25 g of dimethyl sulfoxide, 4.40 g of copper was added and stirred at 60 ° C. for 2 hours and then at room temperature for 16 hours. After completion of the reaction, 30 ml of a saturated aqueous ammonium chloride solution was added to the reaction mixture, filtered through Celite, and the filtrate was extracted with 20 ml of diethyl ether.
  • Step 2 Production of 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetamide 4% by mass of 2.4 g of ethyl 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetate It was dissolved in 20 ml of ammonia methanol solution and stirred at room temperature for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 2.1 g of the objective product as white crystals.
  • Step 3 Preparation of 2- (4-bromo-2-chlorophenyl) -2,2-difluoroethylamine
  • 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetamide To a solution of 2.0 g of 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetamide in 5 ml of tetrahydrofuran Under ice-cooling, 40 ml of an 8.5 mol% tetrahydrofuran solution of borane-tetrahydrofuran complex was added dropwise. After completion of the dropwise addition, stirring was continued at the same temperature for 30 minutes and then at 70 ° C. for 2 hours.
  • Step 4 Preparation of N- [2- (4-Bromo-2-chlorophenyl) -2,2-difluoroethyl] carbamic acid-tert-butyl 2- (4-Bromo-2-chlorophenyl) -2,2-difluoro
  • ethylamine (1.50 g) in dichloromethane (5 ml) were added di-tert-butyl dicarbonate (1.50 g) and triethylamine (0.85 g), and the mixture was stirred at room temperature for 16 hours.
  • Step 5 Preparation of N- [2- [2-Chloro-4- (trimethylsilylethynyl) phenyl] -2,2-difluoroethyl] carbamic acid-tert-butyl N- [2- (4-Bromo-2-chlorophenyl] ) -2,2-difluoroethyl] carbamic acid-tert-butyl in a solution of 820 mg of N, N-dimethylformamide in 0.4 ml of triethylamine, 327 mg of trimethylsilylacetylene, 85 mg of copper (I) iodide and dichlorobis (triphenylphosphine) palladium (II) 78 mg was added, and the mixture was stirred at 60 ° C.
  • Step 6 Preparation of N- [2- [2-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -2,2-difluoroethyl] carbamic acid-tert-butyl N- [2 -[2-Chloro-4- (trimethylsilylethynyl) phenyl] -2,2-difluoroethyl] carbamic acid-tert-butyl 500 mg of toluene in 2 ml solution of triethylamine 0.4 ml, 2-fluoro-5-iodopyridine 346 mg, iodine 49 mg of copper (I) chloride, 45 mg of dichlorobis (triphenylphosphine) palladium (II) and 1.5 ml of a 1M tetrahydrofuran solution of tetrabutylammonium fluoride were added, and the mixture was stirred at room temperature for 2
  • Step 7 Preparation of 2- [3-Chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -2,2-difluoroethylamine N- [2- [2-Chloro-4-[( 6-Fluoropyridin-3-yl) ethynyl] phenyl] -2,2-difluoroethyl] carbamic acid-tert-butyl To a solution of 330 mg of dichloromethane was added 1 ml of trifluoroacetic acid, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure.
  • Step 8 N- [2- [2-Chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -2,2-difluoroethyl] -3-trifluoromethyl-2-pyridinecarboxamide
  • Step 1 Preparation of 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetonitrile 2- (4-Bromo-2-chlorophenyl) -2,2-difluoro prepared in Step 2 of Synthesis Example 5
  • 5.63 g of trifluoroacetic anhydride was added dropwise with stirring under ice cooling, followed by stirring at the same temperature for 1 hour. After completion of the reaction, 20 ml of water was added to the reaction mixture and extracted with 20 ml of ethyl acetate.
  • Step 2 Preparation of 2- (4-bromo-2-chlorophenyl) -2,2-difluoro-1-methylethylamine
  • 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetonitrile 1.8 g of diethyl
  • 5 ml of a 35 mol% diethyl ether solution of methylmagnesium bromide was added dropwise with stirring under ice cooling, followed by stirring at the same temperature for 1 hour.
  • 10 ml of methanol was added dropwise to the reaction mixture with stirring under ice cooling, and the mixture was stirred for 30 minutes.
  • Step 3 Preparation of N- [2- (4-Bromo-2-chlorophenyl) -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl 2- (4-Bromo-2-chlorophenyl) -2 , 2-Difluoro-1-methylethylamine 1.30 g of di-tert-butyl dicarbonate and 1.60 g of triethylamine were added to 5 ml of dichloromethane in 1.50 g and stirred at room temperature for 16 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml ⁇ 1).
  • Step 4 Preparation of N- [2- [2-chloro-4- (trimethylsilylethynyl) phenyl] -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl N- [2- (4-bromo -2-chlorophenyl) -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl 900 mg of N, N-dimethylformamide in 2 ml of solution, 0.4 ml of triethylamine, 346 mg of trimethylsilylacetylene, 90 mg of copper (I) iodide Then, 82 mg of dichlorobis (triphenylphosphine) palladium (II) was added, and the mixture was stirred at 60 ° C.
  • Step 6 Preparation of 2- [2-chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] -2,2-difluoro-1-methylethylamine N- [2- [ 2-Chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl 1 ml of fluoroacetic acid was added and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure.
  • Step 1 Production of N- [2- [2-chloro-4- (ethynyl) phenyl] -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl Prepared in Step 4 of Synthesis Example 6 To a solution of 817 mg of tert-butyl N- [2- [2-chloro-4- (trimethylsilylethynyl) phenyl] -2,2-difluoro-1-methylethyl] carbamic acid in 4 ml of tetrahydrofuran was added tetrabutyl.
  • Step 2 Preparation of N- [2- [2-chloro-4-[(1-methylpyrazol-4-yl) ethynyl] phenyl] -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl N- [2- [2-Chloro-4- (ethynyl) phenyl] -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl 647 mg and 4-iodo-1-methylpyrazole 529 mg N, N -To a solution of 6-dimethylformamide was added 1.27 g of cesium carbonate, 37 mg of copper (I) iodide, 113 mg of 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene and 44 mg of palladium (II) acetate, The mixture was stirred at 70 ° C.
  • reaction mixture was allowed to cool to room temperature, 5 ml of ethyl acetate and 5 ml of water were added, the organic layer was separated, and the aqueous layer was extracted with 5 ml of ethyl acetate.
  • the organic layers were combined and washed with 10 ml of a saturated aqueous ammonium chloride solution, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • Step 3 Preparation of 2- [2-chloro-4-[(1-methylpyrazol-4-yl) ethynyl] phenyl] -2,2-difluoro-1-methylethylamine N- [2- [2-chloro- 4-[(1-Methylpyrazol-4-yl) ethynyl] phenyl] -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl trifluoroacetic acid was stirred in ice-cooled 6 ml solution of 590 mg in dichloromethane. 2 ml was added and stirred at the same temperature for 4 hours.
  • Step 4 N- [2- [2-Chloro-4-[(1-methylpyrazol-4-yl) ethynyl] phenyl] -2,2-difluoro-1-methylethyl] -2- (trifluoromethyl)
  • benzamide 2- [2-chloro-4-[(1-methylpyrazol-4-yl) ethynyl] phenyl] -2,2-difluoro-1-methylethylamine 103 mg in 2 ml of N, N-dimethylformamide in 2 ml -(Trifluoromethyl) benzoic acid 76 mg, triethylamine 100 mg, N, N-dimethyl-4-aminopyridine 5 mg and O- (1-benzotriazolyl) -N, N, N ′, N ′,-tetramethyluro 128 mg of nitrotetrafluoroborate was added and stirred at room temperature for 16 hours.
  • Step 1 N- [2- [2-Chloro-4-[(benzo [b] furan-5-yl) ethynyl] phenyl] -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl Production N- [2- (4-Bromo-2-chlorophenyl) -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl 786 mg and 5- (trimethylsilylethynyl) produced in Step 3 of Synthesis Example 6 ) In a solution of 569 mg of benzo [b] furan in 4 ml of N, N-dimethylformamide, 620 mg of triethylamine, 39 mg of copper (I) iodide, 118 mg of 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene, palladium acetate 46 mg of (II) and 2.7 ml of a 1M
  • reaction mixture was allowed to cool to room temperature, 5 ml of ethyl acetate and 5 ml of water were added, the organic layer was separated, and the aqueous layer was extracted with 5 ml of ethyl acetate.
  • the organic layers were combined and washed with 10 ml of 10% by mass aqueous ammonia, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • Step 2 Preparation of 2- [2-chloro-4-[[(benzo [b] furan-5-yl) ethynyl] phenyl] -2,2-difluoro-1-methylethylamine N- [2- [2- Chloro-4-[(benzo [b] furan-5-yl) ethynyl] phenyl] -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl 720 mg in dichloromethane 6 ml solution under ice-cooling and stirring 2 ml of trifluoroacetic acid was added and stirred at the same temperature for 3 hours.
  • Step 2 Preparation of 2- (4-bromo-2-chlorophenyl) propylamine
  • 2- (4-bromo-2-chlorophenyl) propanenitrile 1.65 g of dichloromethane in 20 ml of dichloromethane was stirred at ⁇ 78 ° C. with diisobutylaluminum. 20 ml of a 1.0M hexane solution of hydride was added dropwise and stirred at room temperature for 16 hours, and then the solvent was distilled off under reduced pressure.
  • Step 3 Preparation of N- [2- (4-Bromo-2-chlorophenyl) propyl] carbamic acid-tert-butyl 2- (4-Bromo-2-chlorophenyl) propylamine Triethylamine 1 in a solution of 1.90 g of dichloromethane in 10 ml of dichloromethane 0.02 g and 1.62 g of di-tert-butyl dicarbonate were added and stirring was continued at room temperature for 16 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, followed by extraction with dichloromethane (20 ml ⁇ 1).
  • the organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient from 0:10 to 2: 8) to obtain 1.50 g of the desired product as a colorless resinous substance.
  • Step 4 Preparation of N- [2- [2-chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] propyl] carbamic acid-tert-butyl N- [2- ( 4-bromo-2-chlorophenyl) propyl] carbamic acid-tert-butyl 760 mg and 2- (trifluoromethyl) -5- (trimethylsilylethynyl) pyridine 636 mg in N, N-dimethylformamide 3 ml solution 662 mg triethylamine, copper iodide (I) 83 mg, 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene 252 mg, palladium (II) 98 mg and tetrabutylammonium fluoride 2.6 ml in 1M tetrahydrofuran were added, , And stirred at 70 ° C.
  • reaction mixture was allowed to cool to room temperature, 5 ml of ethyl acetate and 5 ml of water were added, the organic layer was separated, and the aqueous layer was extracted with 5 ml of ethyl acetate.
  • the organic layers were combined and washed with 10 ml of 10% by mass aqueous ammonia, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • Step 5 Preparation of 2- [2-chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] propylamine N- [2- [2-chloro-4-[[6 -(Trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] propyl] carbamic acid-tert-butyl
  • dichloromethane a solution of 365 mg of dichloromethane in 6 ml of dichloromethane was added 2 ml of trifluoroacetic acid with stirring under ice cooling, and the same temperature was maintained for 1 hour. Stir.
  • Step 6 Preparation of N- [2- [2-chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] propyl] -2- (trifluoromethyl) benzamide 2- [ 2-Chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] propylamine in a solution of 103 mg of triethylamine and 92 mg of triethylamine in 2 ml of dichloromethane was stirred under ice-cooling and 2- (trifluoromethyl) benzoyl. 76 mg of chloride was added and stirred at room temperature for 16 hours.
  • Step 1 Preparation of 1- (4-bromo-2-chlorophenyl) cyclopropanecarbonitrile 2.12 g of (4-bromo-2-chlorophenyl) acetonitrile, tetra-n-butyl in a solution of 4.13 g of potassium hydroxide in 10 ml of water 297 mg of ammonium bromide and 3.46 g of 1,2-dibromoethane were added and stirred at 50 ° C. for 3 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of water was added, and the mixture was extracted with diethyl ether (20 ml ⁇ 1).
  • the organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient from 0:10 to 2: 8) to obtain 2.26 g of the desired product as pale yellow crystals.
  • Step 3 Preparation of N-[[1- (4-Bromo-2-chlorophenyl) cyclopropyl] methyl] carbamic acid-tert-butyl [1- (4-Bromo-2-chlorophenyl) cyclopropyl] methylamine 1.
  • dichloromethane a solution of 50 g of dichloromethane in 10 ml of triethylamine were added 874 mg and di-tert-butyl dicarbonate 1.38 g, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, followed by extraction with dichloromethane (20 ml ⁇ 1).
  • the organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (5: 95-20: 80 gradient) to obtain 1.50 g of the objective product as brown crystals.
  • Step 4 Preparation of N-[[1- [2-Chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] cyclopropyl] methyl] carbamic acid-tert-butyl N- [ [[1- (4-Bromo-2-chlorophenyl) cyclopropyl] methyl] carbamic acid-tert-butyl 780 mg and 2- (trifluoromethyl) -5- (trimethylsilylethynyl) pyridine 631 mg N, N-dimethylformamide 5 ml In the solution, 754 mg of N, N, N ′, N′-tetramethylethylenediamine, 41 mg of copper (I) iodide, 125 mg of 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene, 48 mg of palladium (II) acetate Then, 2.6 ml
  • reaction mixture was allowed to cool to room temperature, 5 ml of ethyl acetate and 5 ml of water were added, the organic layer was separated, and the aqueous layer was extracted with 5 ml of ethyl acetate.
  • the organic layers were combined and washed with 10 ml of a saturated aqueous ammonium chloride solution, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • Step 5 Preparation of [1- [2-Chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] cyclopropyl] methylamine N-[[1- [2-Chloro- 4-[[6- (Trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] cyclopropyl] methyl] carbamic acid-tert-butyl To 200 ml of dichloromethane was added 1 ml of trifluoroacetic acid with stirring under ice-cooling. And stirred at the same temperature for 1.5 hours.
  • Step 6 N-[[1- [2-Chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] cyclopropyl] methyl] -2- (trifluoromethyl) benzamide
  • Preparation [1- [2-Chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] cyclopropyl] methylamine (140 mg) and triethylamine (81 mg) in dichloromethane (2 ml) were stirred under ice-cooling.
  • This invention compound can be manufactured according to the said manufacturing method and an Example.
  • Examples of alkynylphenyl-substituted amide compounds included in the present invention produced in the same manner as in Synthesis Examples 1 to 10 are shown in Tables 3 to 12, and examples of production intermediates thereof are shown in Tables 13 and 12.
  • the alkynylphenyl-substituted amide compounds and their production intermediates included in the present invention are not limited to these.
  • c-Pr represents cyclopropyl
  • Ph represents phenyl
  • the aromatic heterocycles represented by D-1-1b to D-51-2a each represent the following structure,
  • the number representing the substitution position of the substituent (Z) n corresponds to the position of the number described in the above structural formula.
  • the description "F” represents "6-fluoropyridin-3-yl”
  • T-17 to T-81 each represent the following structure.
  • “* 1” in the melting point column means that the property of the compound was oily or resinous.
  • Solpol registered trademark
  • N-methylpyrrolidone Solvesso (registered trademark) 200 (manufactured by ExxonMobil)
  • test drug solution B The compound of the present invention was dissolved in dimethyl sulfoxide to prepare a 1% strength solution. This chemical solution was diluted to a predetermined concentration and used in Test Examples 9 to 13 below.
  • Test Example 1 Cucumber powdery mildew prevention effect test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm 3 plastic pot, and the test drug solution A of the present compound was diluted to a concentration of 500 ppm by adding distilled water at the cotyledon stage. 5 ml sprayed per pot. After air drying, the cucumber was placed in an air-conditioned greenhouse (20 ° C.) and sprayed with a conidial spore suspension of cucumber powdery mildew (Erysiphe polygoni, Synonym; Erysiphe betae). After 9 days at the same temperature, the proportion of the lesions formed in the inoculated leaves was measured, and the control value was calculated according to the following formula.
  • Control value [1- (Sickness area ratio of treated area / Uncovered lesion area ratio)] ⁇ 100
  • the following compounds showed a control value of 70% or more.
  • Compound of the present invention No.1-002,1-003,1-004,1-013,1-027,2-001,2-007,2-012,2-017,2-020,2-021, 2-024,2-026,3-001,3-002,3-003,3-007,3-011,3-015,3-016,3-017,3-018,3-019,3- 022,3-038,4-001,4-002 * , 4-007,4-012,4-013,4-014,9-002,9-005.
  • the said * mark represents having implemented the test using a 100 ppm concentration chemical
  • Test example 2 Cucumber gray mold prevention effect test (spore inoculation) Cucumber (variety: Sagamihanjiro) was planted in a 90 cm 3 plastic pot, and at the cotyledon stage, the test drug solution A of the compound of the present invention was diluted with distilled water to a concentration of 500 ppm and sprayed with 5 ml per pot. After air drying, the treated leaves were cut out and placed in a plastic container. A conidial spore suspension of cucumber gray mold fungus (Botrytis cinerea) and a dissolved PDA medium were mixed at a ratio of 1: 1, and 30 ⁇ l of the treated leaves were inoculated dropwise. After inoculation, after placing it at 20 ° C.
  • the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
  • the test was performed by 2 continuous systems. As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
  • the present compound No.1-001,1-002,1-003,1-004,1-006,1-007,1-008,1-009,1-011,1-012,1-014, 1-015,1-016,1-017,1-018,1-019,1-020,1-025,1-026 * , 1-027,1-028,1-029,1-033,1 -035,1-036,1-039,1-040,2-001,2-002,2-003,2-004,2-005,2-007,2-010,2-011,2-012 , 2-013,2-014,2-015,2-016,2-017,2-018,2-019,2-020,2-021,2-022,2-023,2-024,2 -026,2-027,2-028,2-029,2-030,2-031,3-001,3-002,3-003,3-005,3-006,3-007,3-009 , 3-010,3-011,3-012,3-013,3-014,3-015,3-016,3-017,3-018,3-019,3-020,3-021,2-022,2-023,2-024,2 -026,2-027,2-0
  • Test example 3 Cucumber gray mold prevention effect test (mycelia inoculation) Cucumber (variety: Sagamihanjiro) was planted in a 90 cm 3 plastic pot, and at the cotyledon stage, the test drug solution A of the compound of the present invention was diluted with distilled water to a concentration of 500 ppm and sprayed with 5 ml per pot. One day later, the pot was placed in a plastic container and inoculated into a cucumber cotyledon treated with a drug with a bacterial agar piece (diameter 5 mm) of cucumber gray mold (Botrytis cinerea) previously cultured in PDA medium.
  • the plastic container After inoculation, the plastic container is covered with plastic, humidified, and left at 20 ° C for 2 days. Then, the proportion of the lesions formed in the inoculated leaves is measured, and the control value is calculated from the same formula as in Test Example 1. did. In addition, the test was performed by 2 continuous systems. As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
  • Test Example 4 Cucumber Nucleus Disease Prevention Effect Test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm 3 plastic pot, and the test drug solution A of the compound of the present invention was diluted to a concentration of 500 ppm by adding distilled water at the cotyledon stage. 5 ml sprayed per pot. After air-drying, the pot was placed in a plastic container and inoculated into a cucumber cotyledon treated with a drug, a garnish containing agar (Sclerotinia sclerotiorum) -containing agar pieces (diameter 5 mm) previously cultured in a PDA medium.
  • agar Sterotinia sclerotiorum
  • the plastic container After inoculation, the plastic container is covered with plastic, humidified, and left at 20 ° C for 2 days. Then, the proportion of the lesions formed in the inoculated leaves is measured, and the control value is calculated from the same formula as in Test Example 1. did. In addition, the test was performed by 2 continuous systems. As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
  • Test Example 5 Cucumber Anthrax Preventive Effect Test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm 3 plastic pot, and test chemical solution A of the compound of the present invention was diluted to a concentration of 500 ppm by adding distilled water at the cotyledon stage. 5 ml spraying treatment was performed. One day later, a conidial spore suspension of cucumber anthracnose fungus (Colletotrichum lagenarium, Synonym; Colletotrichum orbiculare) was spray-inoculated and placed in an inoculation box at a temperature of 25 ° C. and a humidity of 100% for 2 days.
  • Test Example 6 Wheat powdery mildew prevention effect test 1.3 Test chemical solution A of the compound of the present invention was added to distilled water in a 90 cm 3 plastic pot planted with 1.3 leaves of wheat (variety: Norin 61), and the concentration was 500 ppm. And 5 ml sprayed per pot. One day after spraying, the pot was placed in an air-conditioned greenhouse (20 ° C.), and wheat was inoculated with conidia of wheat powdery mildew (Blumeria graminis f. Sp. Tritici). Thereafter, it was held for 7 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.
  • Test Example 7 Wheat Blight Prevention Effect Test 1.3 Distilled water was added to test chemical solution A of the present invention in a 90 cm 3 plastic pot planted with 3 leaf stage wheat (variety: Haruyutaka) to a concentration of 500 ppm. Then, 5 ml per pot was sprayed. One day after spraying, a conidial spore suspension of wheat blight fungus (Phaeosphaeria nodorum, Synonym; Septoria nodorum) was spray-inoculated on wheat and placed in an inoculation box at a temperature of 20 ° C. and a humidity of 100% for 2 days. Thereafter, it was placed in an air-conditioned greenhouse (20 ° C.) and held for 6 days.
  • a conidial spore suspension of wheat blight fungus (Phaeosphaeria nodorum, Synonym; Septoria nodorum) was spray-inoculated on wheat and placed in an inoculation box at a temperature of 20 ° C
  • the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same calculation formula as in Test Example 1.
  • the test was performed by 2 continuous systems. As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
  • Test Example 8 Wheat Red Rust Prevention Effect Test 1.3 Into a 90 cm 3 plastic pot planted with 3 leaf stage wheat (variety: Norin 61), distilled water was added to the test chemical solution A of the present invention to a concentration of 500 ppm. Diluted and sprayed 5 ml per pot. One day after spraying, the spore suspension of wheat rust (Puccinia recondita) was spray-inoculated on wheat and placed in an inoculation box at a temperature of 20 ° C. and a humidity of 100% for 1 day. Thereafter, it was placed in an air-conditioned greenhouse (20 ° C.) and held for 8 days.
  • the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same calculation formula as in Test Example 1.
  • the test was performed by 2 continuous systems. As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
  • the compound of the present invention No. 3-022,4-002 * .
  • the said * mark represents having implemented the test using a 100 ppm concentration chemical
  • Test Example 9 Antibacterial activity test against Aspergillus oryzae After dispensing 60 ⁇ l of potato dextrose 1% agar to a 96-well plate, sterile water containing 10 Aspergillus niger spores (10 spores / 3 ⁇ l) was added. 30 ⁇ l was added per well. From this, the test chemical solution B of the compound of the present invention was diluted with distilled water to a concentration of 100 ppm, added 10 ⁇ l per well, and allowed to stand at 25 ° C. under dark conditions. The bacterial flora area ratio (%) 2 days after the addition of the drug was determined, and the efficiency (%) for the untreated area was calculated by the following formula.
  • Efficacy (%) [1 ⁇ (area ratio of treated flora / area area of untreated flora)] ⁇ 100
  • Compound of the present invention No.1-001,1-002,1-003,1-004,1-007,1-008,1-009,1-012,1-014,1-016,1-017, 1-018,1-019,1-025,1-026,1-027,1-028,1-029,1-033,1-036,1-043,2-001,2-002,2- 003,2-004,2-005,2-006,2-007,2-012,2-013,2-014,2-015,2-016,2-017,2-018,2-019, 2-020,2-021,2-022,2-023,2-024,2-025,2-026,2-027,2-028,2-029,3-001,3-002,3- 003,3-004,3-005,3-006,3-007,3-008,3-009,3-010,3-011,3-012,3-013,3-015,3-016,
  • Test Example 10 Insecticidal test against sweet potato nematode After dispensing 60 ⁇ l of potato dextrose 1% agar medium into a 96-well plate, each well was given sterile water (10 eggs / 3 ⁇ l) containing eggs of sweet potato nematode (Meloidogyne incognita). 30 ⁇ l per dose was added. From this, the test chemical solution B of the compound of the present invention was diluted to 100 ppm with distilled water, diluted to 10 ppm with distilled water, added 10 ⁇ l per well, and kept at 25 ° C. under dark conditions. And left to stand.
  • Efficacy (%) [(number of untreated eggs treated + number of inactive larvae) / number of untreated group active larvae] x 100 As a result, among the tested compounds, the following compounds showed an efficiency (%) of 50% or more.
  • Test Example 11 Control Effect Test on Sweet Potato Nematode Cellulose-planted spinach seedlings (about 2 weeks after germination) filled with 10 g of soil per cell were added 100 ppm of test chemical solution B of the compound of the present invention with distilled water. Dilute to concentration and treat 1 ml per strain. One hour after the treatment, water containing 2 L larvae of Meloidogyne incognita (2 L larvae: 100/1 ml) was inoculated to the strain, 1 ml per cell. It was kept in a greenhouse for 3 weeks, and the degree of root nodules formed at the root was determined according to the following disease index and disease severity, and the efficiency (%) for the untreated area was calculated by the following equation.
  • Test Example 12 Insecticidal test for torsion stomachworms After dispensing 60 ⁇ l of potato dextrose 1% agar medium to a 96-well plate, sterile water (10 eggs / 3 ⁇ l) containing eggs of torsion stomachworms (Haemonchus contortus), 30 ⁇ l was added per well. From this, the test chemical solution B of the compound of the present invention was diluted with distilled water to a concentration of 100 ppm, added 10 ⁇ l per well, and allowed to stand at 25 ° C. under dark conditions. The number of unhatched eggs and the number of inactive larvae 4 days after the addition of the drug were measured, and the efficiency (%) for the untreated group was calculated from the same calculation formula as in Test Example 10.
  • Test Example 13 Insecticidal test for soybean cyst nematode Sterile water (10 larvae / larvae) containing 2 L larvae of callus-cultured soybean cyst nematode (Heterodera glycines) after dispensing 60 ⁇ l of 1% agar medium with potato dextrose into a 96-well plate 3 ⁇ l) was added in an amount of 30 ⁇ l per well. From this, the test chemical solution B of the compound of the present invention was diluted with distilled water to a concentration of 100 ppm, added 10 ⁇ l per well, and allowed to stand at 25 ° C. under dark conditions.
  • efficacy (%) (Number of inactive larvae in treated area / number of active larvae in untreated area) ⁇ 100 As a result, among the tested compounds, the following compounds showed an efficiency (%) of 50% or more.
  • Test Example 14 Insecticidal test against torsion stomachworm (comparison test) After dispensing 60 ⁇ l of potato dextrose 1% agar medium to a 96-well plate, sterile water (10 eggs / 3 ⁇ l) containing eggs of Haemonchus contortus was added in an amount of 30 ⁇ l per well. From this, the test drug solution B of the compound of the present invention and the comparative compound was diluted to each predetermined concentration by adding distilled water, added 10 ⁇ l per well, and allowed to stand at 25 ° C. under dark conditions.
  • Comparative compound A WO 2012-028676, compound 4.19
  • Comparative compound B WO 2012-028676, compound 4.59
  • the alkynylphenyl-substituted amide compound according to the present invention exhibits excellent pest control activity, particularly bactericidal / nematicidal activity, and has almost no adverse effect on non-target organisms such as mammals, fish and useful insects. Is a very useful compound. It should be noted that all of the specifications, claims and abstract of Japanese Patent Application No. 2016-251125 filed on Dec. 26, 2016 and Japanese Patent Application No. 2017-134111 filed on Jul. 07, 2017. The contents of which are hereby incorporated herein by reference.

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  • Health & Medical Sciences (AREA)
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Abstract

L'invention concerne de nouveaux agents de lutte contre les nuisibles, en particulier, un bactéricide et un nématicide. L'invention concerne un composé amide substitué par un alkylphényle représenté par la formule (I) [dans laquelle : G1 désigne une structure représentée par G1-2, G1-3, G1-4, etc. ; X1 représente un atome d'halogène, difluorométhyle, trifluorométhyle, etc. ; Y1 représente un atome d'halogène, etc. ; Y2 représente un atome d'hydrogène, etc. ; R1 représente un atome d'hydrogène, un atome d'halogène, un méthoxy, etc. ; R2 représente un atome d'hydrogène, un atome d'halogène, etc. ; R3 représente un atome d'hydrogène, un méthyle, etc. ; R4 représente un atome d'hydrogène, etc. ; R5 représente un atome d'hydrogène, etc. ; R6 représente un phényle (Z)m substitué, D-1, D-2, D-6, D-8, D-23, D-31, etc. ; Z représente un atome d'halogène, un méthyle trifluorométhyle, -OCH=CH-, -N(R12)N=CH-, -CH=CHCH=CH-, etc. ; R12 représente un méthyle, etc. ; m représente 1, 2, 3, etc. ; n représente 0, 1, 2, etc. ; et n1 représente 0, etc.] ou un sel de celui-ci, et un agent de lutte contre les nuisibles le comprenant.
PCT/JP2017/046693 2016-12-26 2017-12-26 Composé amide substitué par l'alkylphényle et agent de lutte antiparasitaire WO2018124088A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2016251125 2016-12-26
JP2016-251125 2016-12-26
JP2017134111A JP2020029402A (ja) 2016-12-26 2017-07-07 アルキニルフェニル置換アミド化合物及び有害生物防除剤
JP2017-134111 2017-07-07

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WO2018124088A1 true WO2018124088A1 (fr) 2018-07-05

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108949771A (zh) * 2018-08-02 2018-12-07 南京农业大学 拟环纹豹蛛c家族杀虫基因及其编码的成熟肽与应用
WO2020002593A1 (fr) * 2018-06-29 2020-01-02 Intervet International B.V. Composé destiné à être utilisé contre une infection helminthique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009539791A (ja) * 2006-06-08 2009-11-19 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト Ｎ−（１−アルキル−２−フェニルエチル）−カルボキサミド誘導体と、それを殺真菌剤として利用する方法
JP2010529062A (ja) * 2007-06-08 2010-08-26 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 殺菌剤として有用なピラゾールカルボン酸アミド類
JP2010529971A (ja) * 2007-06-15 2010-09-02 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 新規殺微生物剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009539791A (ja) * 2006-06-08 2009-11-19 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト Ｎ−（１−アルキル−２−フェニルエチル）−カルボキサミド誘導体と、それを殺真菌剤として利用する方法
JP2010529062A (ja) * 2007-06-08 2010-08-26 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 殺菌剤として有用なピラゾールカルボン酸アミド類
JP2010529971A (ja) * 2007-06-15 2010-09-02 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 新規殺微生物剤

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020002593A1 (fr) * 2018-06-29 2020-01-02 Intervet International B.V. Composé destiné à être utilisé contre une infection helminthique
CN108949771A (zh) * 2018-08-02 2018-12-07 南京农业大学 拟环纹豹蛛c家族杀虫基因及其编码的成熟肽与应用
CN108949771B (zh) * 2018-08-02 2021-10-19 南京农业大学 拟环纹豹蛛c家族杀虫基因及其编码的成熟肽与应用

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