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WO2013141362A1 - Dérivé de carboxamide de thiazole et procédé d'utilisation de celui-ci - Google Patents

Dérivé de carboxamide de thiazole et procédé d'utilisation de celui-ci Download PDF

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Publication number
WO2013141362A1
WO2013141362A1 PCT/JP2013/058305 JP2013058305W WO2013141362A1 WO 2013141362 A1 WO2013141362 A1 WO 2013141362A1 JP 2013058305 W JP2013058305 W JP 2013058305W WO 2013141362 A1 WO2013141362 A1 WO 2013141362A1
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group
alkyl group
alkoxy
halo
groups
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Japanese (ja)
Inventor
田中　浩二
弘和 藤原
長谷部　元宏
岡田　敦
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Nihon Nohyaku Co Ltd
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Nihon Nohyaku Co Ltd
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Priority to CN201380026771.1A priority Critical patent/CN104302644A/zh
Priority to KR20147028729A priority patent/KR20140138931A/ko
Publication of WO2013141362A1 publication Critical patent/WO2013141362A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the present invention relates to a novel thiazolecarboxamide derivative or a salt thereof, a plant disease control agent containing the compound as an active ingredient, and a method for using the same.
  • the present invention provides a thiazole carboxamide derivative useful as a plant disease control agent in order to satisfy these demands.
  • R 1 is (1a) a halogen atom; (2a) a (C 1 -C 6 ) alkyl group; (3a) a halo (C 1 -C 6 ) alkyl group; (4a) a (C 1 -C 6 ) alkoxy group; or (5a) a halo (C 1 -C 6 ) alkoxy group; (6a) represents a (C 3 -C 6 ) cycloalkyl group, Y represents O, S, SO, SO 2 , —N (R 3 ) —, or —N ⁇ C (R 3 ) —.
  • R 3 is (1b) a hydrogen atom; (2b) a (C 1 -C 6 ) alkyl group; (3b) a (C 2 -C 6 ) alkenyl group; (4b) a (C 2 -C 6 ) alkynyl group; (5b) a halo (C 1 -C 6 ) alkyl group; (6b) a halo (C 2 -C 6 ) alkenyl group; (7b) a halo (C 2 -C 6 ) alkynyl group; (8b) formyl group; (9b) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (10b) a halo (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (11b) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group; (12b)
  • R 2 is (1c) an amino (C 1 -C 6 ) alkyl group; (2c) a mono (C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group; (3c) di (C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group (the alkyl groups of di (C 1 -C 6 ) alkylamino may be the same or different); (4c) a (C 1 -C 6 ) alkylcarbonylamino (C 1 -C 6 ) alkyl group; (5c) a (C 1 -C 6 ) alkoxycarbonylamino (C 1 -C 6 ) alkyl group; (6c) a (C 1 -C 6 ) alkylsulfonylamino (C 1 -
  • R 8 is (1f) a hydrogen atom; (2f) a (C 1 -C 6 ) alkyl group; (3f) a (C 1 -C 6 ) alkoxy group; (4f) a (C 3 -C 6 ) cycloalkyl group; (5f) a (C 1 -C 6 ) alkylcarbonyl group; (6f) (C 3 -C 6 ) cycloalkylcarbonyl group; (7f) (C 1 -C 6 ) alkoxycarbonyl group; (8f) a (C 3 -C 6 ) cycloalkoxycarbonyl group; or (9f) represents a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, X 1 , X 2 and X 3 may be the same or different; (1g) hydrogen atom; (2g) a halogen atom; (3g) formyl group; (4g) cyano group; (5g) hydroxy
  • R 1 is (1a) a halogen atom; (2a) a (C 1 -C 6 ) alkyl group; (3a) a halo (C 1 -C 6 ) alkyl group; (4a) a (C 1 -C 6 ) alkoxy group; or (6a) represents a (C 3 -C 6 ) cycloalkyl group, Y is O, S, —N (R 3 ) —, or —N ⁇ C (R 3 ) —.
  • R 3 is (1b) a hydrogen atom; (2b) a (C 1 -C 6 ) alkyl group; (8b) formyl group; (9b) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (11b) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group; (12b) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group; (13b) a (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group; (14b) a (C 1 -C 6 ) alkoxycarbonyl group; (15b) (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkylcarbonyl groups; (16b) a (C 1 -C 6 ) alkylcarbonyl
  • R 2 is (1c) an amino (C 1 -C 6 ) alkyl group; (2c) a mono (C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group; (3c) di (C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group (the alkyl groups of di (C 1 -C 6 ) alkylamino may be the same or different); (4c) a (C 1 -C 6 ) alkylcarbonylamino (C 1 -C 6 ) alkyl group; (5c) a (C 1 -C 6 ) alkoxycarbonylamino (C 1 -C 6 ) alkyl group; (6c) a (C 1 -C 6 ) alkylsulfonylamino (C 1 -C 6 ) alkyl
  • R 8 is (1f) a hydrogen atom; (3f) a (C 1 -C 6 ) alkoxy group; (4f) a (C 3 -C 6 ) cycloalkyl group; (5f) a (C 1 -C 6 ) alkylcarbonyl group; or (7f) represents a (C 1 -C 6 ) alkoxycarbonyl group, X 1 , X 2 and X 3 may be the same or different, (1g) hydrogen atom; (2g) a halogen atom; (4g) cyano group; (6g) a (C 1 -C 6 ) alkoxyimino (C 1 -C 6 ) alkyl group; (7g) a (C 1 -C 6 ) alkyl group; (8g) a halo (C 1 -C 6 ) alkyl group; (9g) (C 1 -C 6 ) alkoxy group; (16g) (C 1 -C 6 ) alkoxy
  • R 1 is (1a) a halogen atom; (2a) a (C 1 -C 6 ) alkyl group; (3a) a halo (C 1 -C 6 ) alkyl group; or (6a) represents a (C 3 -C 6 ) cycloalkyl group, Y is O, —N (R 3 ) —, or —N ⁇ C (R 3 ) —.
  • R 3 is (1b) a hydrogen atom; (2b) a (C 1 -C 6 ) alkyl group; (8b) formyl group; (9b) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (11b) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group; (12b) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group; (13b) a (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group; (14b) a (C 1 -C 6 ) alkoxycarbonyl group; (15b) (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkylcarbonyl groups; (16b) a (C 1 -C 6 ) alkylcarbonyl
  • R 2 is (1c) an amino (C 1 -C 6 ) alkyl group; (2c) a mono (C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group; (3c) di (C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group (the alkyl groups of di (C 1 -C 6 ) alkylamino may be the same or different); (5c) a (C 1 -C 6 ) alkoxycarbonylamino (C 1 -C 6 ) alkyl group; (6c) a (C 1 -C 6 ) alkylsulfonylamino (C 1 -C 6 ) alkyl group; (7c) mono (C 1 -C 6 ) alkylaminocarbonyl group; (9c) mono (C 1 -C 6 ) alkylaminocarbonyl group; (9c) mono (C 1 -C 6 ) alkylamin
  • R 4 represents a (C 1 -C 6 ) alkyl group or a halo (C 1 -C 6 ) alkyl group, The thiazolecarboxamide derivative or a salt thereof according to any one of the above [1] to [3], wherein R 5 , R 6 and R 7 each represent a hydrogen atom; [5] A plant disease control agent comprising the thiazolecarboxamide derivative or a salt thereof according to any one of the above [1] to [4] as an active ingredient; [6] Control of plant diseases characterized by treating the target crop and / or seeds of the target crop with an effective amount of the thiazolecarboxamide derivative or salt thereof according to any one of [1] to [4] above Method; [7] Use of the thiazolecarboxamide derivative according to any one of [1] to [4] above or a salt thereof as a plant disease control agent or the like.
  • the present invention provides a compound useful as a plant disease control agent having superior performance as compared with the prior art, particularly as a rice blast control agent by water surface application or box treatment.
  • Halogen atom and “halo” indicate a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • (C 1 -C 6 ) alkyl group means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, neopentyl group A straight-chain or branched alkyl group having 1 to 6 carbon atoms such as a normal group or a normal hexyl group;
  • (C 2 -C 6 ) alkenyl group means, for example, a linear or branched carbon atom having 2 to 6 carbon atoms such as vinyl group, allyl group, normal butenyl group, normal pentenyl group, normal hexenyl group, etc.
  • (C 2 -C 6 ) alkynyl means, for example, ethynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 1-butynyl, -Butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 1,1 -Linear or branched carbon atoms such as dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, etc. Six alkynyl groups are shown.
  • Halo (C 1 -C 6 ) alkyl group refers to a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, For example, trifluoromethyl group, difluoromethyl group, fluoromethyl group, perfluoroethyl group, 2,2,2-trifluoroethyl group, perfluoroisopropyl group, chloromethyl group, bromomethyl group, 1-bromoethyl group, 2, Examples include 3-dibromopropyl group.
  • halo (C 2 -C 6 ) alkenyl group refers to a linear or branched alkenyl group having 2 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, For example, 2,2-dichlorovinyl group, 2,2-dibromovinyl group, 3-chloroallyl group, 3,3-difluoroallyl group, 3,3-dichloroallyl group, 4-chloro-2-butenyl group, 4, Examples include 4,4-trifluoro-2-butenyl group, 4,4,4-trichloro-2-butenyl group, 5-chloro-3-pentenyl group, 6-fluoro-2-hexenyl group and the like.
  • halo (C 2 -C 6 ) alkynyl group refers to a linear or branched alkynyl group having 2 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, For example, 2-fluoroethynyl group, 2-bromoethynyl group, 2-chloroethynyl group, 2-iodoethynyl group, 3-chloro-1-propynyl group, 1-chloro-2-propynyl group, 3-chloro-1- Methyl-2-propynyl group, 4-chloro-1-butynyl group, 4-chloro-2-butynyl group, 4-chloro-3-butynyl group, 3-chloro-1-pentynyl group, 5,5,5-tri Fluoro-3-pentynyl group, 1-chloro-2-butynyl group, 4-chloro-1-methyl-2-but
  • Examples of the “(C 3 -C 6 ) cycloalkyl group” include cycloalkyl groups having 3 to 6 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like.
  • (C 1 -C 6 ) alkoxy group means, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyl A linear or branched alkoxy group having 1 to 6 carbon atoms, such as an oxy group, a neopentyloxy group, and a normal hexyloxy group.
  • halo (C 1 -C 6 ) alkoxy group refers to a linear or branched alkoxy group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, For example, trifluoromethoxy group, difluoromethoxy group, perfluoroethoxy group, 2,2,2-trifluoroethoxy group, perfluoroisopropoxy group, chloromethoxy group, bromomethoxy group, 1-bromoethoxy group, 2,3- A dibromopropoxy group etc. are mentioned.
  • (C 1 -C 6 ) alkylthio group means, for example, methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, normal pentylthio group
  • (C 1 -C 6 ) alkylsulfinyl group means, for example, methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, A linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a normal pentylsulfinyl group, an isopentylsulfinyl group, and a normal hexylsulfinyl group.
  • (C 1 -C 6 ) alkylsulfonyl group means, for example, methylsulfonyl group, ethylsulfonyl group, normalpropylsulfonyl group, isopropylsulfonyl group, normalbutylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, A linear or branched alkylsulfonyl group having 1 to 6 carbon atoms such as a normal pentylsulfonyl group, an isopentylsulfonyl group, and a normal hexylsulfonyl group.
  • Halo (C 1 -C 6 ) alkylthio group refers to a linear or branched alkylthio group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, For example, trifluoromethylthio group, difluoromethylthio group, perfluoroethylthio group, 2,2,2-trifluoroethylthio group, perfluoroisopropylthio group, chloromethylthio group, bromomethylthio group, 1-bromoethylthio group, Examples include 2,3-dibromopropylthio group.
  • halo (C 1 -C 6 ) alkylsulfinyl group refers to a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
  • trifluoromethylsulfinyl group difluoromethylsulfinyl group, perfluoroethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, perfluoroisopropylsulfinyl group, chloromethylsulfinyl group, bromomethylsulfinyl group, 1 -Bromoethylsulfinyl group, 2,3-dibromopropylsulfinyl group and the like.
  • halo (C 1 -C 6 ) alkylsulfonyl group is a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
  • trifluoromethylsulfonyl group difluoromethylsulfonyl group, perfluoroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, perfluoroisopropylsulfonyl group, chloromethylsulfonyl group, bromomethylsulfonyl group, 1 -Bromoethylsulfonyl group, 2,3-dibromopropylsulfonyl group and the like.
  • (C 1 -C 6 ) alkylcarbonyl group means, for example, methylcarbonyl group (acetyl group), ethylcarbonyl group, normal propylcarbonyl group, isopropylcarbonyl group, normal butylcarbonyl group, tertiary butylcarbonyl group, etc.
  • a linear or branched alkyl-carbonyl group having 1 to 6 carbon atoms is shown.
  • halo (C 1 -C 6 ) alkylcarbonyl group means, for example, a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
  • Carbonyl group for example, trifluoroacetyl group, difluoroacetyl group, perfluoroethylcarbonyl group, perfluoroisopropylcarbonyl group, 2,2,2-trifluoroethylcarbonyl group, chloroacetyl group, bromoacetyl group, 1- Examples thereof include a bromoethylcarbonyl group and a 2,3-dibromopropylcarbonyl group.
  • Examples of the “(C 3 -C 6 ) cycloalkylcarbonyl group” include cycloalkyl-carbonyl groups having 3 to 6 carbon atoms such as cyclopropylcarbonyl group, cyclobutylcarbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group and the like. Indicates.
  • the “(C 1 -C 6 ) alkoxycarbonyl group” means, for example, a straight chain such as a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, a tertiary butoxycarbonyl group or the like.
  • a branched alkoxy-carbonyl group having 1 to 6 carbon atoms is shown.
  • Examples of the “(C 3 -C 6 ) cycloalkoxycarbonyl group” include, for example, cycloalkoxy-having 3 to 6 carbon atoms such as cyclopropoxycarbonyl group, cyclobutoxycarbonyl group, cyclopentyloxycarbonyl group, cyclohexyloxycarbonyl group and the like. A carbonyl group is shown.
  • “Mono (C 1 -C 6 ) alkylamino group” means, for example, N-methylamino group, N-ethylamino group, N-normalpropylamino group, N-isopropylamino group, N-normalbutylamino group, Linear or branched chain such as N-isobutylamino group, N-secondary butylamino group, N-tertiary butylamino group, N-normal pentylamino group, N-neopentylamino group, N-normal hexylamino group, etc.
  • a monoalkylamino group having 1 to 6 carbon atoms is shown.
  • “Di (C 1 -C 6 ) alkylamino group (the alkyl group of di (C 1 -C 6 ) alkylamino may be the same or different)” means, for example, an N, N-dimethylamino group N, N-diethylamino group, N, N-dinormalpropylamino group, N, N-diisopropylamino group, N, N-dinormalbutylamino group, N, N-diisobutylamino group, N, N-disecondary Butylamino group, N, N-ditertiary butylamino group, N, N-dinormalpentylamino group, N, N-dineopentylamino group, N, N-dinormalhexylamino group, N-methyl-N- Ethylamino group, N-methyl-N-normal propylamino group, N-methyl-N-isopropylamino group, N
  • “Mono (C 1 -C 6 ) alkylaminocarbonyl group” means, for example, N-methylaminocarbonyl group, N-ethylaminocarbonyl group, N-normalpropylaminocarbonyl group, N-isopropylaminocarbonyl group, N- N-butylaminocarbonyl group, N-isobutylaminocarbonyl group, N-secondary butylaminocarbonyl group, N-tertiarybutylaminocarbonyl group, N-normalpentylaminocarbonyl group, N-neopentylaminocarbonyl group, N-normalhexyl
  • a linear or branched monoalkylamino-carbonyl group having 1 to 6 carbon atoms such as an aminocarbonyl group is shown.
  • “Di (C 1 -C 6 ) alkylaminocarbonyl group (the alkyl group of di (C 1 -C 6 ) alkylamino may be the same or different)” means, for example, N, N-dimethylamino Carbonyl group, N, N-diethylaminocarbonyl group, N, N-dinormalpropylaminocarbonyl group, N, N-diisopropylaminocarbonyl group, N, N-dinormalbutylaminocarbonyl group, N, N-diisobutylaminocarbonyl group N, N-disecondary butylaminocarbonyl group, N, N-ditertiary butylaminocarbonyl group, N, N-dinormalpentylaminocarbonyl group, N, N-dineopentylaminocarbonyl group, N, N-di Normal hexylaminocarbonyl group, N-methyl-N-eth
  • “Mono (C 1 -C 6 ) alkylaminothiocarbonyl group” means, for example, N-methylaminothiocarbonyl group, N-ethylaminothiocarbonyl group, N-normalpropylaminothiocarbonyl group, N-isopropylaminothio Carbonyl group, N-normal butylaminothiocarbonyl group, N-isobutylaminothiocarbonyl group, N-secondary butylaminothiocarbonyl group, N-tertiary butylaminothiocarbonyl group, N-normalpentylaminothiocarbonyl group, N- A linear or branched monoalkylamino-thiocarbonyl group having 1 to 6 carbon atoms, such as a neopentylaminothiocarbonyl group and an N-normal hexylaminothiocarbonyl group.
  • “Di (C 1 -C 6 ) alkylaminothiocarbonyl group (the alkyl group of di (C 1 -C 6 ) alkylamino may be the same or different)” means, for example, N, N-dimethyl Aminothiocarbonyl group, N, N-diethylaminothiocarbonyl group, N, N-dinormalpropylaminothiocarbonyl group, N, N-diisopropylaminothiocarbonyl group, N, N-dinormalbutylaminothiocarbonyl group, N, N-diisobutylaminothiocarbonyl group, N, N-disecondary butylaminothiocarbonyl group, N, N-ditertiary butylaminothiocarbonyl group, N, N-dinormalpentylaminothiocarbonyl group, N, N-dineo A pentylaminothiocarbonyl group, an N
  • the “(C 1 -C 6 ) alkoxyimino (C 1 -C 6 ) alkyl group” is a linear or branched alkoxyimino group having 1 to 6 carbon atoms in the form of (C 1 -C 6 ) alkyl.
  • a methoxyiminomethyl group, an ethoxyiminomethyl group, a normal propoxyiminomethyl group, an isopropoxyiminomethyl group, a 1- (methoxyimino) ethyl group, a 1- (ethoxyimino) ethyl group, 1- (normal propoxyimino) methyl group, 1- (isopropoxyimino) ethyl group, 2- (methoxyimino) ethyl group, 2- (ethoxyimino) ethyl group, 2- (normalpropoxyimino) methyl group, 2- (Isopropoxyimino) ethyl group and the like can be mentioned.
  • “Hydroxyimino (C 1 -C 6 ) alkyl group” refers to a group in which a hydroxyimino group is bonded to a (C 1 -C 6 ) alkyl group, for example, a hydroxyiminomethyl group, 1- (hydroxyimino) ethyl Group, 2- (hydroxyimino) ethyl group and the like.
  • “Hydroxy (C 1 -C 6 ) alkyl group” refers to a group in which a hydroxy group is bonded to a (C 1 -C 6 ) alkyl group, such as a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group. Group, 3-hydroxypropyl group, 4-hydroxybutyl group and the like.
  • (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group means a group in which a (C 1 -C 6 ) alkoxy group is bonded to a (C 1 -C 6 ) alkyl group, Methoxymethyl group, ethoxymethyl group, normal propoxymethyl group, isopropoxymethyl group, normal butoxymethyl group, secondary butoxymethyl group, tertiary butoxymethyl group, normal pentyloxymethyl group, isopentyloxymethyl group, neopentyloxymethyl group Group, normal hexyloxymethyl group, 1-methoxyethyl group, 1-ethoxyethyl group, 1-normalpropoxyethyl group, 1-isopropoxyethyl group, 1-normalbutoxyethyl group, 1-secondary butoxyethyl group, 1- Tertiary butoxyethyl group, 1-normal pentylo Xylethyl group, 1-isopentyloxye
  • Halo (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl refers to a group in which a halo (C 1 -C 6 ) alkoxy group is bonded to a (C 1 -C 6 ) alkyl group;
  • trifluoromethoxymethyl group, difluoromethoxymethyl group, perfluoroethoxymethyl group, 2,2,2-trifluoroethoxymethyl group, perfluoroisopropoxymethyl group chloromethoxymethyl group, bromomethoxymethyl group, 1- Bromoethoxymethyl group, 2,3-dibromopropoxymethyl group, 1-trifluoromethoxyethyl group, 1-difluoromethoxyethyl group, 1-perfluoroethoxyethyl group, 1- (2,2,2-trifluoroethoxy) Ethyl group, 1-perfluoroisopropoxyethyl group, 1-chloromethoxyethyl group, 1-bro
  • (C 2 -C 6 ) alkenyloxy (C 1 -C 6 ) alkyl group means a group in which a (C 2 -C 6 ) alkenyloxy group is bonded to a (C 1 -C 6 ) alkyl group,
  • (C 2 -C 6 ) alkynyloxy (C 1 -C 6 ) alkyl group means a group in which a (C 2 -C 6 ) alkynyloxy group is bonded to a (C 1 -C 6 ) alkyl group, For example, ethynyloxymethyl group, 2-propynyloxymethyl group, (1-methyl-2-propynyloxy) methyl group, (1,1-dimethyl-2-propynyloxy) methyl group, 1-butynyloxymethyl group, 2-butynyloxymethyl group, 3-butynyloxymethyl group, 1-pentynyloxymethyl group, 2-pentynyloxymethyl group, 3-pentynyloxymethyl group, 4-pentynyloxymethyl group, (1 -Methyl-2-butynyloxy) methyl group, (1-methyl-3-butynyloxy) methyl group, (1,1-dimethyl-2-butyl
  • (C 3 -C 6 ) cycloalkoxy (C 1 -C 6 ) alkyl group means a group in which a (C 3 -C 6 ) cycloalkoxy group is bonded to a (C 1 -C 6 ) alkyl group,
  • (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group means that (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy group is (C 1- C 6 ) represents a group bonded to an alkyl group, for example, 2- (methoxy) ethoxymethyl group, 2- (ethoxy) ethoxymethyl group, 2- (normalpropoxy) ethoxymethyl group, 2- (isopropoxy) Ethoxymethyl group, 2- (normal butoxy) ethoxymethyl group, 2- (secondary butoxy) ethoxymethyl group, 2- (tertiarybutoxy) ethoxymethyl group, 2- (normalpentyloxy) ethoxymethyl group, 2- (iso Pentyloxy) ethoxymethyl group, 2- (neopentyloxy) ethoxymethyl group, 2- (normal hexyloxy) ethoxymethyl 1- (methoxy
  • (C 1 -C 6 ) alkylcarbonyloxy (C 1 -C 6 ) alkyl group means a linear or branched alkyl-carbonyloxy group having 1 to 6 carbon atoms (C 1 -C 6 ) A group bonded to an alkyl group, for example, acetyloxymethyl group, ethylcarbonyloxymethyl group, normal propylcarbonyloxymethyl group, isopropylcarbonyloxymethyl group, normal butylcarbonyloxymethyl group, tertiary butylcarbonyloxymethyl group Group, 1-acetyloxyethyl group, 1-ethylcarbonyloxyethyl group, 1-normalpropylcarbonyloxyethyl group, 1-isopropylcarbonyloxyethyl group, 1-normalbutylcarbonyloxyethyl group, 1-tertiarybutylcarbonyloxy Ethyl group, 2 Acetyloxyethyl group, 2-
  • Phenyl (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl refers to a group in which a phenyl group is bonded to the above (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group.
  • phenylmethoxymethyl group 1-phenylethoxymethyl group, 2-phenylethoxymethyl group, 3-phenylpropoxymethyl group, 4-phenylbutoxymethyl group, 5-phenylpentyloxymethyl group, 6-phenylhexyloxymethyl 1- (phenylmethoxy) ethyl group, 1- (1-phenylethoxy) ethyl group, 1- (2-phenylethoxy) ethyl group, 1- (3-phenylpropoxy) ethyl group, 1- (4-phenyl) Butoxy) ethyl, 1- (5-phenylpentyloxy) ethyl, 1- (6-phenylhexyloxy) ethyl, 2 -(Phenylmethoxy) ethyl group, 2- (1-phenylethoxy) ethyl group, 2- (2-phenylethoxy) ethyl group, 2- (3-phenylpropoxy) ethyl group, 2-
  • Phenyl (C 1 -C 6 ) alkyl group means a group in which a phenyl group is bonded to the above (C 1 -C 6 ) alkyl group.
  • a phenylmethyl group benzyl group
  • 1-phenylethyl group 2-phenylethyl group
  • 3-phenylpropyl group 4-phenylbutyl group and the like.
  • (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group means a group in which a (C 1 -C 6 ) alkylthio group is bonded to a (C 1 -C 6 ) alkyl group, Methylthiomethyl group, ethylthiomethyl group, normal propylthiomethyl group, isopropylthiomethyl group, normal butylthiomethyl group, secondary butylthiomethyl group, tertiary butylthiomethyl group, normal pentylthiomethyl group, isopentylthiomethyl group Normal hexylthiomethyl group, 1-methylthioethyl group, 1-ethylthioethyl group, 1-normalpropylthioethyl group, 1-isopropylthioethyl group, 1-normalbutylthioethyl group, 1-secondary butylthioethyl group 1-tertiarybutyl
  • (C 1 -C 6) alkylsulfinyl (C 1 -C 6) alkyl group refers to (C 1 -C 6) alkylsulfinyl group is (C 1 -C 6) groups bound to an alkyl group, For example, methylsulfinylmethyl group, ethylsulfinylmethyl group, normal propylsulfinylmethyl group, isopropylsulfinylmethyl group, normal butylsulfinylmethyl group, secondary butylsulfinylmethyl group, tertiary butylsulfinylmethyl group, normalpentylsulfinylmethyl group, isopentyl Sulfinylmethyl group, normal hexylsulfinylmethyl group, 1-methylsulfinylethyl group, 1-ethylsulfinylethyl group, 1-normalpropylsulfinylethyl
  • (C 1 -C 6) alkylsulfonyl (C 1 -C 6) alkyl group refers to (C 1 -C 6) alkylsulfonyl group is (C 1 -C 6) groups bound to an alkyl group, For example, methylsulfonylmethyl group, ethylsulfonylmethyl group, normal propylsulfonylmethyl group, isopropylsulfonylmethyl group, normal butylsulfonylmethyl group, secondary butylsulfonylmethyl group, tertiary butylsulfonylmethyl group, normal pentylsulfonylmethyl group, isopentyl Sulfonylmethyl group, normal hexylsulfonylmethyl group, 1-methylsulfonylethyl group, 1-ethylsulfonylethyl group, 1-normalpropylsulfonylethyl
  • (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkylcarbonyl group means a group in which the above (C 1 -C 6 ) alkoxy group is bonded to (C 1 -C 6 ) alkylcarbonyl group.
  • (C 1 -C 6) alkoxycarbonyl (C 1 -C 6) alkyl group refers to (C 1 -C 6) alkoxycarbonyl group (C 1 -C 6) groups bound to an alkyl group, For example, methoxycarbonylmethyl group, ethoxycarbonylmethyl group, normal propoxycarbonylmethyl group, isopropoxycarbonylmethyl group, normal butoxycarbonylmethyl group, tertiary butoxycarbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group 1-normalpropoxycarbonylethyl group, 1-isopropoxycarbonylethyl group, 1-normalbutoxycarbonylethyl group, 1-tertiarybutoxycarbonylethyl group, 2-methoxycarbonylethyl group, 2-ethoxycarbonylethyl group, 2 -Normal propoxycarbonylethyl group, 2-isopropoxycarbonylethyl group, 2-
  • Amino (C 1 -C 6 ) alkyl group refers to a group in which an amino group is bonded to a (C 1 -C 6 ) alkyl group. For example, an aminomethyl group, 1-aminoethyl group, 2-aminoethyl Group, 3-aminopropyl group, 4-aminobutyl group and the like.
  • “Mono (C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group” means a group in which a mono (C 1 -C 6 ) alkylamino group is bonded to a (C 1 -C 6 ) alkyl group.
  • “Di (C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group (the alkyl groups of di (C 1 -C 6 ) alkylamino may be the same or different.”)
  • a group in which (C 1 -C 6 ) alkylamino group (the alkyl group of di (C 1 -C 6 ) alkylamino may be the same or different) is bonded to (C 1 -C 6 ) alkyl group
  • (C 1 -C 6 ) alkylcarbonylamino (C 1 -C 6 ) alkyl group means a linear or branched alkyl-carbonylamino group having 1 to 6 carbon atoms (C 1 -C 6 ) A group bonded to an alkyl group, for example, acetylaminomethyl group, ethylcarbonylaminomethyl group, normal propylcarbonylaminomethyl group, isopropylcarbonylaminomethyl group, normal butylcarbonylaminomethyl group, tertiary butylcarbonylaminomethyl group Group, 1-acetylaminoethyl group, 1-ethylcarbonylaminoethyl group, 1-normalpropylcarbonylaminoethyl group, 1-isopropylcarbonylaminoethyl group, 1-normalbutylcarbonylaminoethyl group, 1-tertiarybutylcarbonylamino Ethyl group
  • (C 1 -C 6 ) alkoxycarbonylamino (C 1 -C 6 ) alkyl group means a linear or branched alkoxy-carbonylamino group having 1 to 6 carbon atoms (C 1 -C 6 ) A group bonded to an alkyl group, such as methoxycarbonylaminomethyl group, ethoxycarbonylaminomethyl group, normal propoxycarbonylaminomethyl group, isopropoxycarbonylaminomethyl group, normal butoxycarbonylaminomethyl group, tertiary butoxycarbonyl Aminomethyl group, 1-methoxycarbonylaminoethyl group, 1-ethoxycarbonylaminoethyl group, 1-normalpropoxycarbonylaminoethyl group, 1-isopropoxycarbonylaminoethyl group, 1-normalbutoxycarbonylaminoethyl group, 1-ter Arylbutoxycarbonylaminoethyl group, 2-methoxycarbonylamin
  • (C 1 -C 6 ) alkylsulfonylamino (C 1 -C 6 ) alkyl group means a linear or branched alkyl-sulfonylamino group having 1 to 6 carbon atoms (C 1 -C 6 ) A group bonded to an alkyl group, for example, methylsulfonylaminomethyl group, ethylsulfonylaminomethyl group, normalpropylsulfonylaminomethyl group, isopropylsulfonylaminomethyl group, normal butylsulfonylaminomethyl group, secondary butylsulfonylaminomethyl group Group, tertiary butylsulfonylaminomethyl group, normal pentylsulfonylaminomethyl group, isopentylsulfonylaminomethyl group, normal hexylsulfonylaminomethyl group, 1-methylsulfonyla
  • “Mono (C 1 -C 6 ) alkylaminocarbonyloxy (C 1 -C 6 ) alkyl group” means that a mono (C 1 -C 6 ) alkylaminocarbonyloxy group is replaced with a (C 1 -C 6 ) alkyl group.
  • a bonded group for example, N-methylaminocarbonyloxymethyl group, N-ethylaminocarbonyloxymethyl group, N-normalpropylaminocarbonyloxymethyl group, N-isopropylaminocarbonyloxymethyl group, N-normalbutylamino Carbonyloxymethyl group, N-isobutylaminocarbonyloxymethyl group, N-secondary butylaminocarbonyloxymethyl group, N-tertiarybutylaminocarbonyloxymethyl group, N-normalpentylaminocarbonyloxymethyl group, N-neopentylamino Carboni Ruoxymethyl group, N-normal hexylaminocarbonyloxymethyl group, 1- (N-methylaminocarbonyloxy) ethyl group, 1- (N-ethylaminocarbonyloxy) ethyl group, 1- (N-normalpropylaminocarbonyloxy) Ethyl group, 1- (N-isopropylamin
  • a di (C 1 -C 6 ) alkylcarbonyloxyamino group (the alkyl group of di (C 1 -C 6 ) alkylamino may be the same or different) is a (C 1 -C 6 ) alkyl group A bonded group, for example, N, N-dimethylaminocarbonyloxymethyl group, N, N-diethylaminocarbonyloxymethyl group, N, N-dinormalpropylaminocarbonyloxymethyl group, N, N-diisopropylaminocarbonyloxy Methyl group, N, N-dinormalbutylaminocarbonyloxymethyl group, N, N-diisobutylaminocarbonyloxymethyl N
  • N- (C 1 -C 6 ) alkyl-N-formylamino (C 1 -C 6 ) alkyl group means that N— (C 1 -C 6 ) alkyl-N-formylamino group is (C 1 — C 6 ) represents a group bonded to an alkyl group, such as N-methyl-N-formylaminomethyl group, N-ethyl-N-formylaminomethyl group, N-normalpropyl-N-formylaminomethyl group, N- Isopropyl-N-formylaminomethyl group, N-normalbutyl-N-formylaminomethyl group, N-isobutyl-N-formylaminomethyl group, N-secondarybutyl-N-formylaminomethyl group, N-tertiarybutyl- N-formylaminomethyl group, N-normalpentyl-N-formylaminomethyl group, N-neopentyl-N
  • N- (C 1 -C 6 ) alkyl-N- (C 1 -C 6 ) alkoxycarbonylamino (C 1 -C 6 ) alkyl group means N- (C 1 -C 6 ) alkyl-N- (C 1 -C 6) alkoxycarbonylamino group represents a (C 1 -C 6) groups bound to an alkyl group, for example, N- methyl -N- methoxycarbonylaminomethyl group, N- methyl -N- ethoxycarbonyl Aminomethyl group, N-methyl-N-normalpropoxycarbonylaminomethyl group, N-methyl-N-isopropoxycarbonylaminomethyl group, N-methyl-N-normalbutoxycarbonylaminomethyl group, N-methyl-N-tarsha Libutoxycarbonylaminomethyl group, 1- (N-methyl-N-methoxycarbonylamino) ethyl group, 1- (N-methyl-N- Toxicarbony
  • the “formyloxy (C 1 -C 6 ) alkyl group” refers to a group in which a formyloxy group is bonded to a (C 1 -C 6 ) alkyl group, such as a formyloxymethyl group, a 1-formyloxyethyl group, Examples include 2-formyloxyethyl group and 3-formyloxypropyl group.
  • “Diformyloxy (C 1 -C 6 ) alkyl group” means a group in which two formyloxy groups are bonded to a (C 1 -C 6 ) alkyl group, and the two formyloxy groups are the same or different carbon atoms. May be substituted. Examples thereof include a diformyloxymethyl group, 1,1-diformyloxyethyl group, 2,2-diformyloxyethyl group, 1,2-diformyloxypropyl group, and the like.
  • the “(C 1 -C 6 ) alkylsulfonyloxy (C 1 -C 6 ) alkyl group” is a linear or branched alkylsulfonyloxy group having 1 to 6 carbon atoms that is linear or branched.
  • alkyl having 1 to 6 carbon atoms such as methylsulfonyloxymethyl group, 1-methylsulfonyloxyethyl group, 2-methylsulfonyloxyethyl group, 1-ethylsulfonyloxyethyl group, 1 -Ethylsulfonyloxyethyl group, 1-isopropylsulfonyloxyethyl group, 2-isopropylsulfonyloxyethyl group, 3-methylsulfonyloxypropyl group and the like.
  • (C 1 -C 6 ) alkoxycarbonyloxy (C 1 -C 6 ) alkyl group means a linear or branched alkyl-carbonyloxy group having 1 to 6 carbon atoms that is linear or branched. And bonded to alkyl having 1 to 6 carbon atoms, such as methoxycarbonyloxymethyl group, 1-methoxycarbonyloxyethyl group, 2-methoxycarbonyloxyethyl group, 3-methoxycarbonyloxypropyl group, etc. Is mentioned.
  • (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl refers to the above (C 1 -C 6 ) alkoxy (C 1 —C 6 ) alkoxy (C 1 -C 6 ) represents a group in which an alkoxy group is bonded to a (C 1 -C 6 ) alkyl group, such as 2- (2- (2-methoxyethoxy) ethoxy) ethyl group Can be mentioned.
  • Carboxyl (C 1 -C 6 ) alkyl refers to a group in which a carboxyl group is bonded to a linear or branched alkyl having 1 to 6 carbon atoms, such as a carboxylmethyl group, 1-carboxyl Examples thereof include an ethyl group and a 2-carboxylethyl group.
  • aromatic heterocyclic group refers to a 5- or 6-membered aromatic heterocyclic group having one or more heteroatoms selected from an oxygen atom, a sulfur atom and a nitrogen atom, and examples thereof include furyl, thienyl, pyridyl, Monocyclic aromatic heterocyclic groups such as pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, triazinyl; quinolyl, isoquinolyl, quinazolyl, quinoxalyl, quinoxalyl, Benzothienyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzimidazolyl, benzotri
  • “Aromatic heterocycle (C 1 -C 6 ) alkyl group” means a group in which the above aromatic heterocycle group is bonded to a (C 1 -C 6 ) alkyl group.
  • “Aromatic heterocyclic (C 1 -C 6 ) oxy” refers to a group in which the aromatic heterocyclic group is bonded to an oxygen atom.
  • non-aromatic heterocyclic group refers to a 5- or 6-membered non-aromatic heterocyclic group having one or more hetero atoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom.
  • Non-aromatic heterocyclic (C 1 -C 6 ) alkyl refers to a group in which the non-aromatic heterocyclic group is bonded to a (C 1 -C 6 ) alkyl group.
  • Non-aromatic heterocyclic oxy (C 1 -C 6 ) alkyl refers to a group in which the non-aromatic heterocyclic oxy group is bonded to a (C 1 -C 6 ) alkyl group, Oxy-methyl group, 1-nonaromatic heterocyclic oxy-ethyl group, 2-nonaromatic heterocyclic oxy-ethyl group, 3-nonaromatic heterocyclic oxy-propyl group, 4-nonaromatic heterocyclic oxy- A butyl group etc. are mentioned.
  • Nonrogen-containing aliphatic heterocyclic ring refers to a 5- or 6-membered aliphatic heterocyclic group containing 0 to 1 oxygen atom, 0 to 1 sulfur atom, and 1 to 2 nitrogen atoms
  • Examples include oxazolidine, thiazolidine, isoxazolidine, isothiazolidine, morpholine, thiomorpholine, piperazine, pyrrolidine, piperidine, tetrahydro-1,2-oxazine, tetrahydro-1,3-oxazine and the like.
  • Examples of the “3- to 6-membered aliphatic ring” include cycloalkanes having 3 to 6 carbon atoms such as cyclopropane, cyclobutane, cyclopentane, and cyclohexane.
  • expressions such as “(C 1 -C 6 )”, “(C 2 -C 6 )”, and “(C 3 -C 6 )” indicate the range of the number of carbon atoms of various substituents.
  • Examples of the salt of the thiazole carboxamide derivative represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, fumarate, maleate and oxalic acid.
  • examples include salts, organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium. .
  • the thiazolecarboxamide derivative represented by the general formula (I) of the present invention may contain one or more asymmetric centers in the structural formula, and there are two or more optical isomers and diastereomers.
  • the present invention includes all the optical isomers and a mixture in which they are contained in an arbitrary ratio.
  • the thiazole carboxamide derivative represented by the general formula (I) of the present invention may have two kinds of geometric isomers derived from a carbon-carbon double bond in the structural formula. All geometric isomers and mixtures containing them in an arbitrary ratio are also included.
  • a halogen atom As R 1 , (1a) a halogen atom; (2a) a (C 1 -C 6 ) alkyl group; (3a) a halo (C 1 -C 6 ) alkyl group; (4a) a (C 1 -C 6 ) alkoxy group; or (6a) (C 3 -C 6 ) cycloalkyl groups are preferred, (1a) a halogen atom; (2a) a (C 1 -C 6 ) alkyl group; (3a) a halo (C 1 -C 6 ) alkyl group; or (6a) (C 3 -C 6 ) cycloalkyl groups are more preferred.
  • O, S, —N (R 3 ) —, or —N ⁇ C (R 3 ) — is preferred, O, —N (R 3 ) —, or —N ⁇ C (R 3 ) — is more preferable.
  • R 2 When Y represents O, S or —N (R 3 ) — (1c) an amino (C 1 -C 6 ) alkyl group; (2c) a mono (C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group; (3c) di (C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group (the alkyl groups of di (C 1 -C 6 ) alkylamino may be the same or different); (4c) a (C 1 -C 6 ) alkylcarbonylamino (C 1 -C 6 ) alkyl group; (5c) a (C 1 -C 6 ) alkoxycarbonylamino (C 1 -C 6 ) alkyl group; (6c) a (C 1 -C 6 ) alkylsulfonylamino (C 1 -C 6 ) alkyl group; (7c)
  • R 2 When Y represents O or —N (R 3 ) — (1c) an amino (C 1 -C 6 ) alkyl group; (2c) a mono (C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group; (3c) di (C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group (the alkyl groups of di (C 1 -C 6 ) alkylamino may be the same or different); (5c) a (C 1 -C 6 ) alkoxycarbonylamino (C 1 -C 6 ) alkyl group; (6c) a (C 1 -C 6 ) alkylsulfonylamino (C 1 -C 6 ) alkyl group; (7c) mono (C 1 -C 6 ) alkylaminocarbonyl group; (9c) mono (C 1 -C 6 ) alkylaminothi
  • R 4 , R 5 , R 6 , and R 7 may be the same or different, (1e) a hydrogen atom; (2e) a (C 1 -C 6 ) alkyl group; (3e) a halo (C 1 -C 6 ) alkyl group; (7e) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; or (8e) R 4 and R 5 , R 6 and R 7 , R 4 and R 6 or R 4 and R 7 are bonded to form a 3- to 6-membered aliphatic ring together with the carbon atom to which they are bonded.
  • Embodiment is preferred, (1e) a hydrogen atom; (2e) a (C 1 -C 6 ) alkyl group; or (3e) A halo (C 1 -C 6 ) alkyl group is more preferred.
  • R 4 , R 5 , R 6 , and R 7 A compound in which R 4 is a (C 1 -C 6 ) alkyl group or a halo (C 1 -C 6 ) alkyl group, and R 5 , R 6 , and R 7 are hydrogen atoms.
  • X 1 , X 2 and X 3 may be the same or different, (1g) hydrogen atom; (2g) a halogen atom; (4g) cyano group; (6g) a (C 1 -C 6 ) alkoxyimino (C 1 -C 6 ) alkyl group; (7g) a (C 1 -C 6 ) alkyl group; (8g) a halo (C 1 -C 6 ) alkyl group; (9g) (C 1 -C 6 ) alkoxy group; (16g) (C 1 -C 6 ) alkoxycarbonyl group; (17g) phenyl group; (18g) may be the same or different and (i) a halogen atom, (ii) a cyano group, (iii) a (C 1 -C 6 ) alkyl group, (iv) a halo (C 1 -C 6 ) alkyl group, ( v) a substituted phenyl
  • the thiazolecarboxamide derivative represented by the general formula (I) of the present invention can be produced, for example, according to the method described in International Publication No. 2008/062878, or is produced according to the following production method. However, it is not limited to these. Manufacturing method 1
  • Examples of the condensing agent used in this reaction include diethyl cyanophosphate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), chlorocarbonates, 2-chloro-1-methyl iodide.
  • DEPC diethyl cyanophosphate
  • CDI carbonyldiimidazole
  • DCC 1,3-dicyclohexylcarbodiimide
  • chlorocarbonates 2-chloro-1-methyl iodide.
  • Pyridinium and the like can be exemplified, and the amount used can be appropriately selected from the range of 0.8 to 1.5 moles relative to the thiazolecarboxylic acid represented by the general formula (II). .
  • the base examples include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; acetates such as sodium acetate and potassium acetate; potassium-t-butoxide, sodium Alkali metal alkoxides such as methoxide and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine and 1,8-diazabicyclo [5.4.0] undec-7-ene; pyridine, dimethylaminopyridine and the like Nitrogen-containing aromatic compounds and the like can be mentioned, and the amount used is usually in the range of 0.5 to 10 moles relative to the thiazolecarboxylic acid represented by the general formula (II).
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate
  • acetates such as sodium acetate and potassium acetate
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; halogens such as methylene chloride, chloroform and carbon tetrachloride Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran; Esters such as ethyl acetate; Dimethylformamide and dimethyl Amides such as acetamide; ketones such as acetone and methyl ethyl ketone; and inert solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, and these inert solvents may be used alone or as 2 A mixture of more than one species can be used.
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
  • the reaction temperature can be from room temperature to the boiling range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out in the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Manufacturing method 2
  • Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; acetates such as sodium acetate and potassium acetate; potassium alkali metal alkoxides such as t-butoxide, sodium methoxide, sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene; pyridine, Nitrogen-containing aromatic compounds such as dimethylaminopyridine and the like can be mentioned, and the amount used is usually 0.5 mol to 10 mol per mol of the thiazolecarboxylic acid halide represented by the general formula (II-1). Used in the range of
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; halogens such as methylene chloride, chloroform and carbon tetrachloride Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran; Esters such as ethyl acetate; Dimethylformamide and dimethyl Amides such as acetamide; ketones such as acetone and methyl ethyl ketone; dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, etc., or an inert solvent of water can be exemplified, and these inert solvents are used alone.
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
  • the reaction temperature can be from room temperature to the boiling range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out in the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • the 2- (substituted pyrazolyl) ethylamine derivative represented by the general formula (III), which is a raw material for production methods 1 and 2, can be produced according to the method described in International Publication No. 2008/062878. .
  • the thiazole carboxylic acid represented by the general formula (II) as the raw material of the production method 1 and the thiazole carboxylic acid halide represented by the general formula (II-1) as the raw material of the production method 2 are produced by the following methods. be able to.
  • Examples of the nitrite compound used in this reaction include alkali metal nitrites such as sodium nitrite and potassium nitrite; alkyls having 1 to 6 carbon atoms such as ethyl nitrite, tert-butyl nitrite, and amyl nitrite.
  • alkyl nitrite having a group can be used, and the amount used is usually 0.8 times mol to 1 with respect to 2-aminothiazole-5-carboxylic acid ethyl ester represented by the general formula (IV). Used in a 5-fold molar range.
  • halogen compound used in this reaction examples include monovalent copper halides such as copper (I) chloride, copper (I) bromide, copper (I) iodide; copper (II) chloride, copper bromide ( II), divalent copper halides such as copper (II) iodide; alkali metal halides such as sodium iodide, potassium bromide and potassium iodide; halogenations such as hydrogen chloride, hydrogen bromide and hydrogen iodide Examples include hydrogen. Each of these halogen compounds is used alone or in combination of two or more. The amount used is in a range of 0.5 to 10 moles in total with respect to 2-aminothiazole-5-carboxylic acid ethyl ester represented by the general formula (IV).
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; halogens such as methylene chloride, chloroform and carbon tetrachloride Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran; Esters such as ethyl acetate; Dimethylformamide and dimethyl Examples include amides such as acetamide; ketones such as acetone and methyl ethyl ketone; nitriles such as acetonitrile; dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and the like, and water inert solvents.
  • Inert solvent alone or 2 It can be used as a mixture or more. Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
  • the reaction temperature can be from room temperature to the boiling range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out in the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • Production method of general formula (V) ⁇ general formula (II-2) 2-halothiazole-5-carboxylic acid ethyl ester represented by general formula (V) and the compound represented by general formula (VI) And thiazole-5-carboxylic acid ethyl ester represented by the general formula (II-2) can be produced by reaction in the presence of an inert solvent.
  • the compound represented by the general formula (VI) may be a commercially available product or can be produced by a method known per se.
  • Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; acetates such as sodium acetate and potassium acetate; potassium alkali metal alkoxides such as t-butoxide, sodium methoxide, sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene; pyridine, Nitrogen-containing aromatic compounds such as dimethylaminopyridine and the like can be mentioned, and the amount used is usually 0.5-fold mol with respect to 2-halothiazole-5-carboxylic acid ethyl ester represented by the general formula (V). It is used in the range of ⁇ 10 times mole.
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • halogens such as methylene chloride, chloroform and carbon tetrachloride.
  • Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran; Esters such as ethyl acetate; Dimethylformamide and dimethyl Examples include amides such as acetamide; ketones such as acetone and methyl ethyl ketone; nitriles such as acetonitrile; dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and the like, and water inert solvents. Inert solvent alone or 2 It can be used as a mixture or more.
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
  • the reaction temperature can be from room temperature to the boiling range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out in the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • General formula (II-2) Production method of general formula (II)
  • the thiazolecarboxylic acid represented by general formula (II) is obtained from thiazole-5-carboxylic acid ethyl ester represented by general formula (II-2). It can be produced by subjecting it to a hydrolysis reaction. Specifically, thiazole-5-carboxylic acid ethyl ester represented by the general formula (II-2) is reacted with a base or an acid in the presence of an inert solvent to represent the general formula (II). Thiazole carboxylic acid can be produced.
  • Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; potassium tert-butoxide, sodium methoxide, sodium ethoxy Alkali metal alkoxides such as thiols and the like can be mentioned, and the amount used is usually 0.5 to 10 times the mol of thiazole-5-carboxylic acid ethyl ester represented by the general formula (II-2).
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • examples thereof include alcohols such as methanol, ethanol and isopropanol; diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran and the like. Chain or cyclic ethers; Amides such as dimethylformamide and dimethylacetamide; Ketones such as acetone and methylethylketone; Nitriles such as acetonitrile; Dimethylsulfoxide, 1,3-dimethyl-2-imidazolidinone and the like An active solvent can be illustrated, and these inert solvents can be used individually or in mixture of 2 or more types.
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
  • the reaction temperature can be from room temperature to the boiling range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out in the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • General formula (II) ⁇ Production method of general formula (II-1) The thiazolecarboxylic acid represented by general formula (II) is reacted in the presence of a halogenating agent and an inert solvent to give a general formula (II- The thiazole carboxylic acid halide represented by 1) can be produced.
  • halogenating agent used in this reaction for example, thionyl chloride, oxalyl chloride, phosphoryl chloride and the like can be mentioned, and the amount used is usually 0. 0 with respect to the thiazolecarboxylic acid represented by the general formula (II). It is used in the range of 5 to 10 moles.
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; halogens such as methylene chloride, chloroform and carbon tetrachloride Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran; Esters such as ethyl acetate; Dimethylformamide and dimethyl Amides such as acetamide; ketones such as acetone and methyl ethyl ketone; dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, etc., or an inert solvent of water can be exemplified, and these inert solvents are used alone.
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
  • the reaction temperature can be from room temperature to the boiling range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out in the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • thiazolecarboxamide derivative derivatives represented by the general formula (I) of the present invention are shown in Tables 1 to 7 and Table 9 below, but the present invention is not limited to these. Absent.
  • “Me” represents a methyl group
  • “Et” represents an ethyl group
  • “Pr” represents a propyl group
  • “Bu” represents a butyl group
  • “Ph” represents a phenyl group
  • n-” represents normal.
  • I- represents iso
  • c- represents an alicyclic hydrocarbon group.
  • the physical properties indicate melting point (° C.) or refractive index n D (measurement temperature; ° C.).
  • Table 8 shows the NMR data.
  • the plant disease control agent containing the thiazolecarboxamide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is various agricultural and forestry, horticulture, and grain storage that harms rice, fruit trees, vegetables, other crops, and flowers. Suitable for disease control such as diseases or sanitary diseases.
  • the plant disease control agent of the present invention has a wide variety of filamentous fungi such as Oomycetes, Ascomycetes, Deuteromycetes, and Basidiomycetes. Not only has an excellent bactericidal effect on bacteria belonging to), but also has an excellent effect on phytopathogenic bacteria and plant viruses.
  • rice diseases include, for example, yellow dwarf disease (S. macrospora), seedling blight (R. chinensis, T. viride), idiot seedling disease (G. fujikuroi), rice blast disease (M. grisea, P oryzae), sheath blight (R. solani), sesame leaf blight (C. miyabeanus), brown panicle (A. padwiki), red rice (E. nigrum), rice koji (C. virens), straw Bacterial blight (P. glumae), leaf sheath browning (P. fuscovaginae), brown streak (P. avenae), seedling blight (P. plantarii), white blight (X.
  • S. macrospora seedling blight
  • R. chinensis T. viride
  • idiot seedling disease G. fujikuroi
  • rice blast disease M. grisea, P oryzae
  • sheath blight R. sol
  • Examples of maize diseases include sesame leaf blight (B. maydis, C. heter ostrophus), soot rot (E. turcicum), spot disease (P. maydis), smut (U. maydis), etc .;
  • Examples of tobacco diseases include plague (P. nicotianae / parasitica), downy mildew (P. tabacina), powdery mildew (E. cichoracearum), anthrax (C. tabacum), and red star disease (A. longipes, A alternata), soot disease (C. salicinum), yellow disease (O. brassicae), etc .
  • Examples of tea diseases include erythema carcinoma (N.
  • Brassicaceae diseases include, for example, Brassicae clubroot (P. brassicae), Brassicaceae white rust (A. macrospora), Brassicaceae downy mildew (P. brassicae), Brassicaceae mycosis (S. sclerotiorum) Cabbage root rot (P. lingam), cabbage strain rot (T. cucumeris), rape white spot (C. brassicicola), cabbage white spot (C. brassicicola), cruciferous black spot (A. brassicae), Cabbage black rot (X. campestris pv. Campestris) etc .; Strawberry diseases include, for example, plague (P. cactorum, P. nicotianae), powdery mildew (S.
  • Tomato diseases include, for example, plague (P. infestans), anthrax (C. phomoides), leaf mold (C. fulvum), spot disease (S. lycopersici), ring rot (A. solani), ulcer disease (C. michiganensis) etc .;
  • solanaceous diseases include S. sclerotiorum, powdery mildew (S. furiginea), brown spot (P. vexans), subtilis (M. nattrassii), and pepper spot (S. sclerotiorum).
  • Cucurbitaceae diseases include cucumber pesticidal disease (P. melonis), cucumber downy mildew (P. cubensis), cucumber powdery mildew (S. furiginea), cucumber vine blight (M. melonis, D. bryoniae) , Watermelon vine blight (M. melonis, D. bryoniae), cucumber sclerotia (S. sclerotiorum), cucumber anthrax (C.
  • cucumber pesticidal disease P. melonis
  • cucumber downy mildew P. cubensis
  • cucumber powdery mildew S. furiginea
  • cucumber vine blight M. melonis, D. bryoniae
  • Watermelon vine blight M. melonis, D. bryoniae
  • cucumber sclerotia S. sclerotiorum
  • cucumber anthrax C.
  • onion and onion diseases include leek downy mildew (P. destructor), onion leaf blight (P. herbarum), onion sclerotia (S. sclerotiorum), onion gray rot (B. alli), onion White spotted leaf blight (B. byssoidea, B. squamosa), black onion black spot (A. porri), onion dry rot (F. oxysporum f. Sp. Cepae), leek rust (P. allii), etc .;
  • root vegetables diseases include carrot black leaf blight (A. dauci), radish black spot (A. brassicicola), etc .
  • flower diseases include rose blight (P.
  • wheat diseases include snow rot (Pythium sp., M. nivalis, S. borealis, F. nivale), snow rot (T. ishikariensis, T. incarnata), and red mold (G. zeae, F avenaceum, F. graminearum, F. culmorum, M. nivale), ergot disease (C. purpurea), blight (G. graminis), strain rot (C. gramineum), sharp eyespot (C. cereale), Powdery mildew (B. graminis f. Sp. Tritici), blight (L. nodorum, S. nodorum), red rust (P.
  • Potato diseases include, for example, powdery scab (S. subterranea), scab (S. scabies), plague (P. infestans), summer plague (A. solani), black bruise (R. solani) , Ring rot (C. michiganensis), ring lot disease (C. michiganensis), etc .;
  • sugar beet diseases include black root disease (A. sochlioides), leaf rot (T. cucumeris), root rot (T. cucumeris), snake eye disease (P. betae), brown spot disease (C. beticora), Spot disease (R. beticora), rust fungus (U. betae), etc .
  • Examples of legume diseases include S.
  • soybean sclerotiorum soybean rust (P. pachyrhizi), soybean downy mildew (P. manshurica), soybean purple spot (C. kikuchii), and soybean black spot (D. phaseolorum var. sojae), soybean black rot (E. glycines), soybean charcoal (M. phaseolina), soybean black root rot (C. crotalariae), groundnut black root rot (C. crotalariae), groundnut black astringent Disease (M. personatum), groundnut scab (S. arachidis), groundnut black mold (A. niger), groundnut brown spot (C. arachidicola), kidney bean disease (C. arachidicola), bean anthracnose (C.
  • kidney bean root rot F. solani f. Sp. Phaseoli
  • bean wilt bacterial disease C. flaccumfasiens
  • azuki bean disease P. griseola
  • pea downy mildew P. pisi
  • Pea powdery mildew E. pisi
  • broad bean plague P. nicotianae
  • broad bean mildew P. viciae
  • Ramame brown spot disease A. fabae
  • apple diseases include powdery mildew (P. leucotricha), rot (V. ceratosperma), white coat (R. necatrix), purple coat (H. mompa), and black spot (V. inaequaris). ), Spotted leaf disease (A. mali), moniliosis (M. mali), anthrax (G. cingulata), ring rot (Botryosphaeria sp.), Blacklot disease (B. obtuse, X. campestris pv. Campestris ), Sunspot disease (M. pomi), brown spot disease (D. mali), red star disease (G. yamadae), cedar-apple rust (G.
  • Juniperi-virginianae Suehirotake disease (S. commune), silver leaf Disease (C. purpurreum), root cancer disease (A. tumefaciens), burn disease (E. amylovora), etc .
  • Pear diseases include, for example, white coat (R. necatrix), black spot (V. nashicola), black spot (A. kikuchiana), red spot (G. asiaticum), powdery mildew (P. pyri) Ring rot (P. piricora), blight (P. fukushii), heart rot (L. sulphureus), root cancer (A. tumefaciens), burn (E.
  • Grape diseases include, for example, white coat (R. necatrix), gray mold (B. cinerea), downy mildew (P. viticola), powdery mildew (U. necator), late rot (G. cingulata), black spot disease (E. ampelina), brown spot disease (P. vitis), rust disease (P. ampelopsidis), black lot disease (G. bidwellii, X. campestris pv. campestris)), Pestalothia vulgaris (P. menezesiana), California disease (X. fastidiosa), root cancer disease (A. vitis), etc .; Peach diseases include, for example, T. deformans, M.
  • Citrus diseases include, for example, white coat (R. necatrix), gray mold (B. cinerea), sunspot (D. citri), scab (E. fawcettii), black spot (G. citricarpa) ), Round blight (P. beltranii), anthrax (C. gloeosporioides), green mold (P. digitatum), blue mold (P.
  • Examples of tree / flower diseases include Akebono powdery mildew (M. akebiae), alder powdery mildew (M. penicillata), elm Dutch elm disease (O. ulmi), chestnut blight (E. parasitica) , Apricot blight (L. persoonii), elm round spot (G. ulmi), cherry black knot (A. morbosa), pine leaf sifter (L. pinastri), needle cast (R. , Needle blight (R. kalkhoffii), pine dipslodia blight (S. sapinea), cherry rust (T.
  • Akebono powdery mildew M. akebiae
  • alder powdery mildew M. penicillata
  • elm Dutch elm disease O. ulmi
  • chestnut blight E. parasitica
  • Apricot blight L. persoonii
  • turf / grass disease examples include turf red blight (P. apahanidermatum), turf summer patch (M. poae), turf hermint sporium leaf blight (D. poae), turf dollar spot (S. homoeocarpa) , Lawn anthracnose (C. graminicora), carraria leaf blight (C. geniculata), lawn large (R. solani), brown patch (R. solani), snow rot (Pythium sp., S. borealis, M.) nivalis, F. nivale, T. ishikariensis, T. incarnata), pasture black sesame disease (P. graminis), alfalfa leaf spot (P.
  • polycytic diseases include various seedling blight (P. ultimum, P. apahanidermatum), various root rots (P. cinnamomi), white coat rot (R. necatrix), rot (V. ceratosperma) ), Half body wilt (V. dahlia, V. albo-atrum), gray mold (B. cinerea), mycorrhizal disease (S. sclerotiorum), white silkworm (S. rolfsii), vegetable blight ( R. solani), purple crest (H. mompa), soft rot (E. carotovora, E. aroideae), root cancer (A.
  • plant pathogenic bacterial diseases include cucumber spotted bacterial disease (P. syringae pv. Lachrymans), rice brown stripe disease (P. avenae), rice seedling bacterial disease (P. plantarii), and rice wilt bacterial disease (P glumae), rice leaf sheath browning disease (P. fuscovaginae), solanaceae bacterial wilt (P. solanacearum), tea scab (P. syringae pv. theae), citrus ulcer disease (X. campestris pv. citri), Cabbage black rot (X. campestris pv.
  • Campestris peach perforated bacterial disease (X. campestris pv. Pruni), rice leaf blight (X. oryzae), grape black lot disease (X. campestris pv. Campestris), apple Blacklot disease (X. campestris pv. Campestris), apple burn disease (E. amylovora), pear burn disease (E. amylovora), soft rot disease (E. aroideae, E. carotovora), kidney bean wilt disease (C. flaccumfasiens) ), Head cancer (A. tumefaciens), grape head cancer (A. vitis), potato scab (S. scabies) Citrus static bone disease (S.
  • tomato canker C. michiganensis
  • potato wheel rot C. michiganensis
  • ring rot C. michiganensis
  • diseases caused by plant viruses include tomato mosaic disease (tobacco mosaic virus), cucumber green spot mosaic disease (cucumber green spot mosaic virus), tobacco stem rot (tobacco stem virus), and wheat atrophy.
  • the plant disease control agent of the present invention has an excellent bactericidal effect against resistant bacteria.
  • the resistant bacteria include gray mold fungus (Botrytis cinerea), sugar beet brown fungus (Cercosporabeticola), apple black rot fungus (Venturia inaequalis), pear black rot fungus (Venturia inaequalis), Venturia nashicola); gray mold fungus (Botrytis cinerea) resistant to dicarboximide fungicides (for example, vinclozolin, procymidone, iprodione) and the like.
  • dicarboximide fungicides for example, vinclozolin, procymidone, iprodione
  • the plant disease control agent comprising the thiazolecarboxamide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient damages paddy field crops, field crops, fruit trees, vegetables, other crops, flowers, etc. Since it has a remarkable control effect on diseases, it is necessary to raise seedling facilities, paddy fields, fields, fruit trees, vegetables, and other crops before the occurrence of the disease or at the time when the occurrence of the disease is confirmed, according to the time when the occurrence of the disease is predicted.
  • the desired effect of the plant disease control agent of the present invention can be achieved by treating the seeds such as flower buds, paddy water, stalks and leaves, or a cultivation carrier such as soil.
  • planting soil such as crops, flower buds, planting hole soil at the time of transplanting, plant origin, irrigation water, paddy processing for paddy rice, cultivation water in hydroponics, etc., and through roots with or without soil
  • irrigation water such as crops, flower buds, planting hole soil at the time of transplanting, plant origin, irrigation water, paddy processing for paddy rice, cultivation water in hydroponics, etc.
  • irrigation water such as crops, flower buds, planting hole soil at the time of transplanting, plant origin, irrigation water, paddy processing for paddy rice, cultivation water in hydroponics, etc.
  • the useful plant which can use the plant disease control agent of this invention is not specifically limited, For example, grains (for example, rice, barley, wheat, rye, oats, corn etc.), beans (soybean, red beans) , Broad beans, green beans, green beans, peanuts, etc.), fruit trees and fruits (apples, citrus, pears, strawberries, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables (cabbage, tomatoes) , Spinach, broccoli, lettuce, onion, green onion, bell pepper, eggplant, strawberry, pepper, pork etc., root vegetables (carrots, potatoes, sweet potatoes, sweet potatoes, sweet potatoes, turnips, lotus roots, burdock, garlic etc.) Salmon, hemp, beet, hop, sugar cane, sugar beet, olive, rubber, coffee, tobacco, tea, etc., cucumbers (pumpkin, cucumber, watermelon, (Wow, melon, etc.), pastures (orchard grass, s
  • the “plant” includes HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, cetoxydim and the like. Also included are plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to herbicides such as acetyl CoA carboxylase inhibitors, bromoxynil, dicamba, 2,4-D.
  • plants that have been given resistance by classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone ALS-inhibiting herbicides such as imazetapil. Already sold under the brand name. Similarly, there are soybeans that are resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron methyl by the classic breeding method, and are already sold under the trade name “STS soybeans”. Similarly, SR corn and the like are examples of plants to which tolerance has been imparted to acetyl CoA carboxylase inhibitors such as trione oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods.
  • Plants to which tolerance to an acetyl CoA carboxylase inhibitor has been imparted are Procedures of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA) 87, 7175-7179 (1990).
  • a mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005).
  • Introducing a plant resistant to an acetyl-CoA carboxylase inhibitor by introducing a mutation associated with imparting resistance to a plant or introducing a mutation associated with imparting resistance into a plant acetyl-CoA carboxylase, and further, chimeric plastic technology (Gura T. et al. 1999.
  • toxins expressed in transgenic plants insecticidal proteins derived from Bacillus cereus and Bacillus popirie; ⁇ - such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis Endotoxins, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematicidal insecticidal proteins; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; lysine, corn-RIP, abrin, ruffin, saporin, bryodin, etc.
  • ⁇ - such as Cry1Ab, Cry1Ac, Cry1F,
  • Bosome inactivating protein RI
  • steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.
  • toxins expressed in such genetically modified plants Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab and other ⁇ -endotoxin proteins, VIP1, VIP2, VIP3A, etc.
  • insecticidal protein hybrid toxins partially defective toxins, and modified toxins.
  • Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques.
  • Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
  • the modified toxin one or more amino acids of the natural toxin are substituted.
  • Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427529, EP-A-451 878, It is described in WO 03/052073 and the like.
  • the plant disease control agent of the present invention is used as it is to control various diseases as it is, or appropriately diluted with water or the like, or used in a plant in which the occurrence of the disease is predicted in an amount effective for disease control in a suspended form.
  • seed treatment such as immersion in seeds, seed dressing, calper treatment, etc.
  • soil, etc. after being applied to the soil, such as crop application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface application, etc.
  • it can be used for nutrient solution in nutrient solution (hydroponics) cultivation, smoke, or trunk injection.
  • Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted and the seed is immersed in a liquid state to infiltrate the drug, a solid preparation or liquid preparation is mixed with the seed, Examples thereof include a method of treating and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting.
  • the “seed” for performing the seed treatment means a plant body at an early stage of cultivation used for plant propagation. For example, in addition to seeds, bulbs, tubers, seed buds, stock buds, baskets, bulbs, or cuttings Mention may be made of plants for vegetative propagation.
  • the “soil” or “cultivation carrier” of the plant when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that can grow plants may be used, and so-called soil, seedling mats, water, etc. may be used. It may be a molecular substance, rock wool, glass wool, wood chip, bark or the like.
  • a liquid formulation such as an emulsion, a flowable agent, or a solid formulation such as a wettable powder or a granular wettable powder is appropriately diluted with water and sprayed, or a powdered powder is sprayed.
  • the application method to the soil include, for example, a method in which a liquid preparation is diluted or not diluted with water and applied to a plant stock or a seedling nursery, etc.
  • a method of spraying to a nursery, etc. a method of spraying powder, wettable powder, granule wettable powder, granule, etc. before sowing or transplanting and mixing with the whole soil, a planting hole, making before planting or planting a plant body
  • Examples thereof include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.
  • the dosage form may vary depending on the time of application such as application at seeding, application at greening period, application at transplanting, etc. Apply by mold. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with ground soil, mixed with soil covering, mixed with the entire soil. Simply, the soil and various preparations may be applied alternately in layers.
  • solid preparations such as jumbo agents, packs, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields.
  • an appropriate preparation can be sprayed and injected into the soil as it is or mixed with fertilizer.
  • a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water mouth or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.
  • a field crop In a field crop, it can be processed to a seed or a cultivation carrier close to a plant body from sowing to raising seedling.
  • treatment on a plant source of a plant being cultivated is suitable. It is possible to perform spraying treatment using a granule or irrigation treatment in a liquid of a drug diluted or not diluted in water. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.
  • the irrigation treatment of the liquid drug or the spraying treatment of the granule to the seedling nursery is preferable.
  • the plant disease control agent of the present invention is generally used in a form convenient for use according to a conventional method on an agrochemical formulation.
  • the thiazolecarboxamide derivative represented by the general formula (I) of the present invention or a salt thereof is dissolved and separated by blending them in a suitable inert carrier or, if necessary, with an auxiliary agent in a suitable ratio. , Suspended, mixed, impregnated, adsorbed or adhered, and formulated into appropriate dosage forms such as suspensions, emulsions, solutions, wettable powders, wettable granules, granules, powders, tablets, packs, etc. Use it.
  • the composition of the present invention can contain, in addition to the active ingredient, additive components usually used for agricultural chemical formulations as necessary.
  • additive components usually used for agricultural chemical formulations as necessary.
  • the additive component include a carrier such as a solid carrier and a liquid carrier, a surfactant, a dispersant, a wetting agent, a binder, a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, and an antifreezing agent. , Anti-caking agents, disintegrants, decomposition inhibitors and the like. In addition, you may use a preservative, a plant piece, etc. for an additional component as needed.
  • These additive components may be used alone or in combination of two or more.
  • the solid carrier examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride.
  • liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • Alcohols such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
  • Ethers normal paraffins, naphthenes, isoparaffins, kerosene, mineral oils and other aliphatic hydrocarbons
  • Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, etc.
  • Esters lactones such as ⁇ -butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, soybean oil, rapeseed oil, Examples thereof include vegetable oils such as cottonseed oil and castor oil, and water. These may be used alone or in combination of two or more.
  • surfactants used as dispersants and wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxye Lenalkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene dio
  • binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000.
  • Polyethylene glycol polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipid (for example, cephalin, lecithin, etc.) cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, cross-linked polyvinylpyrrolidone, maleic acid and styrenes Polymers, (meth) acrylic acid copolymers, half-esters of polycarboxylic alcohol polymers and dicarboxylic acid anhydrides, water soluble salts of polystyrene sulfonic acid, para Fin, terpene, polyamide resins, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, synthetic resin emulsions, and the like.
  • phospholipid for example, cephalin, lecithin, etc.
  • cellulose powder dextrin
  • polyaminocarboxylic acid chelate compound cross-linked polyviny
  • thickener examples include xanthan gum, guar gum, diyutane gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch derivative, water-soluble polymer such as polysaccharide, high-purity bentonite, fumed silica ( Inorganic fine powders such as fumed silica (white carbon).
  • the colorant examples include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.
  • antifreezing agent examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • Adjuvants for preventing caking and promoting disintegration include, for example, polysaccharides such as starch, alginic acid, mannose, galactose, polyvinylpyrrolidone, fumed silica (fumed silica), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride copolymer, starch / polyacrylonitrile graft copolymer A polymer etc. are mentioned.
  • the decomposition inhibitor examples include desiccants such as zeolite, quicklime and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • desiccants such as zeolite, quicklime and magnesium oxide
  • antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds
  • ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • preservative examples include potassium sorbate, 1,2-benzothiazolin-3-one, and the like.
  • functional aids such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, UV absorbers and other supplements as necessary Agents can also be used.
  • the blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the plant disease control agent of the present invention.
  • 0.01 to 50 parts by weight 0.01 to 50% by weight with respect to the total weight of the plant disease control agent
  • the amount of the plant disease control agent of the present invention varies depending on various factors, such as purpose, target disease, crop growth, disease occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc.
  • the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 ares depending on the purpose.
  • the plant disease control agent of the present invention is further used for other agricultural and horticultural insecticides, acaricides, nematicides, agricultural and horticultural purposes for the purpose of controlling diseases to be controlled, the appropriate period of control, or reducing the dose. It can also be used by mixing with bactericides, biopesticides and the like, and can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc., depending on the situation of use.
  • Examples of agricultural and horticultural fungicides used for the same purpose include aureofungin, azaconazole, azithiram, acipetacs, acibenzolar, acibenzolar-S-methyl (acibenzolar-S). -methyl), azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam , Isothianil, isovaledione, isopyrazam, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenfos, imalilil , Iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, mezoleoleech ), Edifenphos, etaconazole, etha
  • herbicides for example, 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2, 4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, acronifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, aslam, acetochlor, Atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone one), amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, amethrin ), Alachlor, ally
  • biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect pox virus (Entomopoxivirus, EPV) ) And other virus preparations, Monocrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasturia ⁇ pene insecticides, and Pasturia pene insecticides Microbial pesticides used as agents, bactericides such as Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis Microbial pesticide to be used in, by using mixed such as biological pesticides utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.
  • NPV nuclear polyhedrosis virus
  • GV granulosis virus
  • CPV
  • examples of biological pesticides include Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusahysrica persimilis), natural enemies such as Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl acetate, (E, Z) ) -4,10-tetradecadinyl acetate, (Z) -8-dodecenyl acetate, (Z) -11-tetradecenyl acetate, (Z) -13-icosen-10-one, 14-methyl-1 - May also be used in combination with pheromone agents such as octadecene It is a function.
  • pheromone agents such as octadecene It is a function.
  • Formulation Example 1 Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above components are uniformly mixed and dissolved to prepare an emulsion.
  • Formulation Example 2 Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is mixed and ground uniformly to form a powder.
  • Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules.
  • Formulation Example 4 Compound of the present invention 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above is uniformly mixed and ground to obtain a wettable powder.
  • test examples of the plant disease control effect of the compound of the present invention will be shown, but the present invention is not limited to the test examples.
  • Test Example 1 Rice blast control effect test (water surface treatment) An emulsion prepared by compounding the compound of the present invention in the same manner as in Formulation Example 1 was irrigated by diluting a predetermined amount of water with rice (cultivar: Kinnanfu) grown in a pot in the same manner as in Formulation Example 1. Six days after the treatment, a spore suspension of rice blast fungus (Magnaporthe grisea) obtained by culturing in a V8 medium was spray-inoculated and maintained under humid conditions at 20 ° C. Seven days after inoculation, the control effect was determined according to the criteria of Test Example 1.
  • the compound of the present invention showed an excellent control effect at a treatment dose of 200 gai / 10a. 1-5, 3-1, 3-7, 3-11, 3-12, 3-13, 3-14, 3-15, 3-16, 3-17, 3-18, 3-19, 3- 23, 3-24, 3-28, 3-29, 3-32, 3-33, 3-34, 3-40, 3-41, 3-42, 3-43, 3-44, 3-45, 3-58, 3-59, 3-60, 3-62, 3-64, 3-66, 3-68, 3-70, 3-72, 3-74, 3-75, 3-76, 3- 77, 3-79, 3-81, 3-83, 3-85, 3-87, 3-89, 3-93, 3-97, 3-101, 3-102, 3-104, 3-105, 3-115, 3-119, 3-121, 3-123, 3-125, 3-127, 3-129, 3-137, 3-151, 3-163, 3-165, 3-167, 3- 169, 3-17 3-171, 3-172, 3-173, 3-174, 3-176, 3-179, 3-180, 3-181, 3-182, 3-188
  • the thiazole carboxamide derivative of the present invention or a salt thereof is a compound that is superior in performance as compared with the prior art, particularly useful as a rice blast control agent by water surface application or box treatment.
  • This application is based on Japanese Patent Application No. 2012-068171 filed in Japan, the contents of which are incorporated in full herein.

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

Abstract

Le but de l'invention est de fournir un agent de lutte contre les maladies des végétaux ayant des performances supérieures à l'état de la technique et en particulier un composé utile tel qu'un agent de contrôle de la piriculariose du riz. L'invention concerne un agent de lutte contre les maladies des végétaux contenant un dérivé de carboxamide de thiazole représenté par la formule générale (I) (dans la formule, R1 représente un atome d'hydrogène, un atome d'halogène, un groupe alkyle, ou un groupe haloalkyle ; Y représente O, S, SO, SO2, -N(R3)-, ou -N=C(R3)- (R3 représente un atome d'hydrogène, un groupe alkyle ou analogue) ; lorsque Y représente O, S, SO, SO2, ou -N(R3)-, R2 représente un groupe aminoalkyle, un groupe alcoxyalkyle, un groupe alcoxyalcoxyalkyle, ou analogue ; lorsque Y représente -N=C(R3)-, R2 représente un groupe alkyle, un groupe alcoxy, ou analogue ; R4, R5, R6, R7 et R8 peuvent être identiques ou différents et représentent un atome d'hydrogène, un groupe alkyle ou analogue ; X1, X2, et X3 peuvent être identiques ou différents et représentent un atome d'hydrogène, un atome d'halogène, un groupe alkyle ou analogue).
PCT/JP2013/058305 2012-03-23 2013-03-22 Dérivé de carboxamide de thiazole et procédé d'utilisation de celui-ci Ceased WO2013141362A1 (fr)

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KR20147028729A KR20140138931A (ko) 2012-03-23 2013-03-22 티아졸카르복사미드 유도체 및 그 사용 방법

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JP2018515548A (ja) * 2015-05-19 2018-06-14 バイエル・クロップサイエンス・アクチェンゲゼルシャフト コーヒーさび病、カンキツ類黒星病、カンキツ類瘡痂病およびバナナブラックシガトカ病の治療方法
US11034669B2 (en) 2018-11-30 2021-06-15 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof

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CN111763663B (zh) * 2020-07-09 2022-04-15 昆明理工大学 一种天麻葡糖基转移酶基因及应用

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WO2011051540A1 (fr) * 2009-10-27 2011-05-05 Orion Corporation Composés modulateurs de récepteurs des androgènes
JP2012092033A (ja) * 2010-10-26 2012-05-17 Nippon Nohyaku Co Ltd ２−アミノチアゾールカルボキサミド誘導体及びその使用方法

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WO2011051540A1 (fr) * 2009-10-27 2011-05-05 Orion Corporation Composés modulateurs de récepteurs des androgènes
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JP2018515548A (ja) * 2015-05-19 2018-06-14 バイエル・クロップサイエンス・アクチェンゲゼルシャフト コーヒーさび病、カンキツ類黒星病、カンキツ類瘡痂病およびバナナブラックシガトカ病の治療方法
US11034669B2 (en) 2018-11-30 2021-06-15 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof

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KR20140138931A (ko) 2014-12-04
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CO7101252A2 (es) 2014-10-31

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