WO2015119099A1 - Composé de pyridine et son application - Google Patents

Composé de pyridine et son application Download PDF

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WO2015119099A1
WO2015119099A1 PCT/JP2015/052938 JP2015052938W WO2015119099A1 WO 2015119099 A1 WO2015119099 A1 WO 2015119099A1 JP 2015052938 W JP2015052938 W JP 2015052938W WO 2015119099 A1 WO2015119099 A1 WO 2015119099A1
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unsubstituted
substituted
alkyl
aryl
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PCT/JP2015/052938
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岩田　淳
藤井　聡
陽平 宗井
朝巳 小林
伸哉 幸堀
元亮 佐藤
英樹 加藤
博生 井上
陽子 大沢
茂樹 西野
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日本曹達株式会社
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Priority to JP2015560979A priority Critical patent/JP6221189B2/ja
Publication of WO2015119099A1 publication Critical patent/WO2015119099A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/68—One oxygen atom attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/08—Bridged systems

Definitions

  • the present invention relates to pyridine compounds and uses such as agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides.
  • This application is Japanese Patent Application No. 2014-020833 filed in Japan on February 5, 2014. Claim the priority based on, the contents of which are incorporated herein.
  • Patent Document 1 discloses a pyridine compound represented by the formula (A) or the formula (B). According to Patent Document 1, this pyridine compound seems to be useful as a complex II inhibitor of an electron transport system.
  • An object of the present invention is to provide a novel pyridine compound, an agricultural and horticultural fungicide, a pest control agent, and an insecticide or acaricide.
  • R 1 represents a hydrogen atom, an unsubstituted or C 1-6 alkyl group substituted with G 1 , or a halogeno group.
  • R 2 and R 3 are each independently an unsubstituted or G 1 -substituted C 1-6 alkyl group, an unsubstituted or G 1 -substituted C 3-8 cycloalkyl group, an unsubstituted or G 2 A C6-10 aryl group substituted with or a halogeno group.
  • R 4 is a hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C2 ⁇ 6 alkenyl group substituted with G 1, which is substituted by unsubstituted or G 1 C2 substituted 1-6 alkynyl group, an unsubstituted or C3 ⁇ 8 cycloalkyl group substituted with G 1, unsubstituted or C6 ⁇ 10 aryl C1 to 6 alkyl group substituted with G 2, unsubstituted or with G 2 3- to 10-membered heterocyclyl group C1-6 alkyl group, formyl group, C1-6 alkylcarbonyl group which is unsubstituted or substituted with G 1 , C6-10 arylcarbonyl group which is unsubstituted or substituted with G 2 , unsubstituted or C1 ⁇ 6 alkoxycarbonyl group substituted with G 1, unsubstituted or C2 ⁇ 6 al
  • G a independently represents a hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C2 ⁇ 6 alkenyl group substituted with G 1, unsubstituted or with G 1 substituted C2 ⁇ 6 alkynyl group, a unsubstituted or C3 ⁇ 8 cycloalkyl group substituted by G 1 or unsubstituted or C6 ⁇ 10 aryl group substituted by G 2,.
  • G b represents a hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C2 ⁇ 6 alkenyl group substituted with G 1, which is substituted by unsubstituted or G 1 C2 2-6 alkynyl group, an unsubstituted or C3 ⁇ 8 cycloalkyl group substituted with G 1, unsubstituted or C6 ⁇ 10 aryl group substituted by G 2 3 or substituted with unsubstituted or G 2,
  • T is an oxygen atom, oxycarbonyl group, carbonyloxy group, oxycarbonyloxy group, sulfur atom, (thio) carbonyl group, carbonyl (thio) group, (thio) carbonyloxy group, oxycarbonyl (thio) group, or-
  • a divalent group represented by O—C ( ⁇ O) —N (G b ) — is shown.
  • G 1 is a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 alkoxy group, a C1-6 alkoxycarbonyl group, a formyloxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy A group, a cyano group, or a halogeno group.
  • G 2 is a C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C3-8 cycloalkyl group, C1-6 haloalkyl group, C1-6 alkoxy C1-6 alkyl group, tri C1-6 alkyl Silyl C1-6 alkyl group, Tri C1-6 alkylsilyl C2-6 alkynyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group , C1-6 haloalkoxy group, C2-6 alkenyloxy group, C2-6 alkynyloxy group, formyl group, C1-6 alkylcarbonyl group, C1-6 alkoxycarbonyl group, formyloxy group, C1-6 alkylcarbonyloxy group C1-6 alkoxycarbonyloxy group, C1-6 alkoxycarbonylamino group, The or C6 ⁇ 10 aryl
  • G 21 represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a cyano group, a nitro group, or a halogeno group.
  • Q represents any one of the organic groups represented by the formulas (II) to (IV).
  • Ar 1 represents an unsubstituted or C6 ⁇ 10 aryl group substituted by G 2 or unsubstituted or 3-10 membered heterocyclyl group which is substituted by G 2,.
  • Ar 2 is unsubstituted or C6 ⁇ 10 aryl group substituted by G 2, unsubstituted or C6 ⁇ 10 aryloxy group which is substituted by G 2, C6 ⁇ 10 substituted with unsubstituted or G 2 aryl C1 ⁇ 6 alkoxy group, an unsubstituted or 3-10 membered heterocyclyl group which is substituted by G 2, unsubstituted or 3-10 membered heterocyclyloxy group substituted with G 2 or unsubstituted or G 2, A substituted 3- to 10-membered heterocyclylthio group is shown.
  • R a represents a hydrogen atom, an amino group, an unsubstituted or substituted C 1-6 alkyl group with G 1 , or an unsubstituted or substituted C 2-10 aryl group with G 2 .
  • A is unsubstituted or C1 ⁇ C6 alkylene group substituted with G 3, unsubstituted or C2 ⁇ C6 alkenylene group substituted with G 3, unsubstituted or C2 ⁇ C6 alkynylene group substituted with G 3 shows the unsubstituted or C1 ⁇ C6 alkylene group which is substituted by G 3, unsubstituted or is oxy C1 ⁇ C6 alkylene group substituted with G 3, unsubstituted C3 ⁇ C6 cycloalkylene group or a carbonyl group, .
  • G 3 is a C1-6 alkyl group, a C1-6 alkoxy group, a formyl group, a C1-6 alkylcarbonyl group, a formyloxy group, a C1-6 alkylcarbonyloxy group, a halogeno group, a C1-6 alkylene group, Or represents an oxo group.
  • B a is unsubstituted or C1 ⁇ C6 alkylene group substituted with G 4, unsubstituted or C2 ⁇ C6 alkenylene group substituted with G 4, unsubstituted or C2 ⁇ C6 alkynylene substituted with G 4 group, an unsubstituted or C3 ⁇ C6 cycloalkylene group substituted by G 4, unsubstituted or C4 ⁇ C6 cycloalkenylene group substituted with G 4 3 ⁇ 6 or of unsubstituted or substituted by G 4,
  • the group represented by a membered heterocyclylene group is shown.
  • G 4 is a C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 alkoxy C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1— 6 alkoxy group, C1 ⁇ 6 haloalkoxy group, C2 ⁇ 6 alkenyloxy group, an unsubstituted or C6 ⁇ 10 aryl group substituted by G 21, unsubstituted or 3-10 membered heterocyclyl group which is substituted by G 21 , a cyano group, a halogeno group, C1 ⁇ 6 alkylene group, C1 ⁇ 6 alkylenedioxy group, an oxo group, C3 ⁇ 8 cycloalkyl C1 ⁇ 6 alkyl group, unsubstituted or substituted with G 21 C6 ⁇ 10 aryl C1 1-6 alkyl group, an unsubstituted or C6 ⁇ 10 ⁇
  • T 1 represents (unsubstituted or G 2 -substituted C 6-10 aryl C 1-6 alkoxyimino) -C 1-6 alkyl group or ferrocenyl-C 1-6 alkyl group. * Indicates the bonding position of the organic group represented by formula (II) to formula (IV).
  • the pyridine compound according to the present invention is a novel compound that has effects such as pest control, bactericidal, acaricidal, insecticidal, etc., does not cause phytotoxicity to plants, and has little toxicity to human fish and environmental impact. . In particular, it exhibits an excellent control effect against wheat diseases.
  • the pyridine compound according to the present invention is useful as an active ingredient of agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides.
  • the pyridine compound according to the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) and a salt thereof.
  • R 1 represents a hydrogen atom, an unsubstituted or C 1-6 alkyl group substituted with G 1 , or a halogeno group.
  • the C1-6 alkyl group may be linear or branched if it has 3 or more carbon atoms.
  • Examples of the C1-6 alkyl group include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n -Hexyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.
  • Examples of the halogeno group include a fluoro group, a chloro group, a bromo group, and an iodo group.
  • the substituent G 1 is a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 alkoxy group, a C1-6 alkoxycarbonyl group, a formyloxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group. , A cyano group, or a halogeno group.
  • C1-6 alkoxy groups include methoxy, ethoxy, n-propoxy, n-butoxy, n-pentyloxy, n-hexyloxy, i-propoxy, i-butoxy, s-butoxy , T-butoxy group, i-hexyloxy group and the like.
  • Examples of the C1-6 alkoxy group include a methoxymethoxy group and a methoxyethoxy group.
  • Examples of the C1-6 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and a t-butoxycarbonyl group.
  • Examples of the C1-6 alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, and a butyryloxy group.
  • Examples of the C1-6 alkoxycarbonyloxy group include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group, and a t-butoxycarbonyloxy group. be able to.
  • the halogeno group in the substituent G 1 is as described above.
  • R 1 is preferably an unsubstituted or substituted C 1-6 alkyl group substituted with G 1 , or a halogeno group, more preferably an unsubstituted C 1-6 alkyl group or halogeno group.
  • R 2 and R 3 are each independently an unsubstituted or G 1 -substituted C 1-6 alkyl group, an unsubstituted or G 1 -substituted C 3-8 cycloalkyl group, an unsubstituted or G 2 A C6-10 aryl group substituted with or a halogeno group.
  • the C1-6 alkyl group, halogeno group, and substituent G 1 in R 2 and R 3 are as described above.
  • Examples of the C3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a 2-adamantyl group.
  • Examples of the C6-10 aryl group include a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, and a tetralinyl group.
  • Substituent G 2 is a C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C3-8 cycloalkyl group, C1-6 haloalkyl group, C1-6 alkoxy C1-6 alkyl group, tri C1-6 6 alkylsilyl C1-6 alkyl group, tri C1-6 alkylsilyl C2-6 alkynyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 Alkoxy group, C1-6 haloalkoxy group, C2-6 alkenyloxy group, C2-6 alkynyloxy group, formyl group, C1-6 alkylcarbonyl group, C1-6 alkoxycarbonyl group, formyloxy group, C1-6 alkylcarbonyl Oxy group, C1-6 alkoxycarbonyloxy group, C1-6 alkoxycarbonylamino group Unsubstit
  • C2-6 alkenyl groups include vinyl, 1-propenyl, 2-propenyl (allyl), 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, -Methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
  • Examples of the C2-6 alkynyl group include ethynyl group, 1-propynyl group (propargyl group), 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2 -Methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group 1,1-dimethyl-2-butynyl group and the like.
  • the C1-6 alkoxy C1-6 alkyl group is the above-described C1-6 alkoxy group substituted for the C1-6 alkyl group already described.
  • C1-6 alkoxy C1-6 alkyl group includes methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, ethoxymethyl group, ethoxyethyl group, n-propoxymethyl group, i -Propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group and the like can be mentioned.
  • the tri C1-6 alkylsilyl group is a C1-6 alkyl group in which a triC1-6 alkylsilyl group is substituted for the C1-6 alkyl group already described.
  • Examples of the tri C1-6 alkylsilyl C1-6 alkyl group include 2- (trimethylsilyl) ethyl group.
  • the tri C1-6 alkylsilyl C2-6 alkynyl group is obtained by substituting the C2-6 alkynyl group already described with a tri C1-6 alkylsilyl group.
  • Examples of the tri-C1-6 alkylsilyl C1-6 alkynyl group include 2- (trimethylsilyl) ethynyl group.
  • the C2-6 alkenyloxy group is a hydroxyl group substituted with a C2-6 alkenyl group.
  • Examples of the C2-6 alkenyloxy group include a vinyloxy group, a 1-propenyloxy group, and a 2-propenyloxy group (allyloxy group).
  • the C2-6 alkynyloxy group is a hydroxyl group substituted with a C2-6 alkynyl group.
  • Examples of the C2-6 alkynyloxy group include an ethynyloxy group and a 1-propynyloxy group (propargyloxy group).
  • the C1-6 alkylcarbonyl group is a group in which the above C1-6 alkyl group is bonded to a carbonyl group.
  • Examples of the C1-6 alkylcarbonyl group include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, and a pivaloyl group.
  • the C1-6 alkoxycarbonylamino group is a group in which the above-described C1-6 alkoxycarbonyl group is substituted on the amino group.
  • Examples of the C1-6 alkoxycarbonylamino group include a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group, an i-propoxycarbonylamino group, an n-butoxycarbonylamino group, and a t-butoxycarbonylamino group. be able to.
  • the C6-10 aryl C1-6 alkyl group is a C1-6 alkyl group substituted with a C6-10 aryl group.
  • Examples of the C6-10 aryl C1-6 alkyl group include a benzyl group and a phenethyl group.
  • the C6-10 aryloxy group is a group in which the above-described C6-10 aryl group is substituted on the hydroxyl group.
  • Examples of the C6-10 aryloxy group include a phenoxy group and a naphthoxy group.
  • the C6-10 aryl C1-6 alkoxy group is a group in which the above-described C6-10 aryl C1-6 alkyl group is substituted on the hydroxyl group.
  • Examples of the C6-10 aryl C1-6 alkoxy group include a benzyloxy group and a phenethyloxy group.
  • the 3- to 10-membered heterocyclyl group is a cyclic group containing 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring.
  • the heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, when at least one ring is heterocyclyl, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring.
  • Examples of the 3- to 10-membered heterocyclyl group include a 3- to 10-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.
  • a 3-membered saturated heterocyclyl group such as an aziridinyl group or an oxiranyl group;
  • a 4-membered saturated heterocyclyl group such as an azetidinyl group or an oxetanyl group;
  • 5-membered saturated heterocyclyl group such as pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, imidazolidinyl group, pyrazolidinyl group, dioxolanyl group;
  • 6-membered saturated heterocyclyl groups such as piperidyl group, piperazinyl group, morpholinyl group, tetrahydropyranyl group, dioxolanyl group, dioxanyl group; Etc.
  • 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridanidyl group, triazinyl group; 9-membered heteroaryl groups such as indolyl group, isoindolyl group, benzofuranyl group, indazolyl group, benzoxazolyl group, benzoisoxazolyl group, benzothiazolyl group, benzisothiazolyl group; 10-membered heteroaryl groups such as quinolinyl group, isoquinol
  • 5-membered partially unsaturated heterocyclyl group such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group; 6-membered partially unsaturated heterocyclyl group such as isoxazolinyl group and dihydropyranyl group; Etc.
  • the 3- to 10-membered heterocyclyl group for G 2 is preferably a 5- to 6-membered saturated heterocyclyl group or a 5- to 6-membered heteroaryl group.
  • the 3- to 10-membered heterocyclyl C1-6 alkyl group is a C1-6 alkyl group substituted with a 3- to 10-membered heterocyclyl group.
  • the 3- to 10-membered heterocyclyl C1-6 alkyl group is preferably a 5- to 6-membered saturated heterocyclyl C1-6 alkyl such as tetrahydrofuranylmethyl group, tetrahydropyranylmethyl group, dioxolanylmethyl group, dioxanylmethyl group, etc.
  • Groups; 5- to 6-membered heteroaryl C1-6 alkyl groups such as a pyrazolylmethyl group and a pyridylmethyl group.
  • the 3- to 10-membered heterocyclyloxy group is a hydroxyl group substituted with a 3- to 10-membered heterocyclyl group.
  • Examples of the 3- to 10-membered heterocyclyloxy group include a pyrazolyloxy group and a pyridyloxy group.
  • the 3- to 10-membered heterocyclyloxy group is preferably a 5- to 6-membered saturated heterocyclyloxy group or a 5- to 6-membered heteroaryloxy group.
  • the C1-6 alkylthio group is obtained by substituting a C1-6 alkyl group for an SH group.
  • Examples of the C1-6 alkylthio group include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group, i-butylthio group and the like.
  • the C1-6 alkylsulfinyl group is a C1-6 alkyl group bonded to a sulfinyl group.
  • Examples of the C1-6 alkylsulfinyl group include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group.
  • the C1-6 alkylsulfonyl group is a sulfonyl group having a C1-6 alkyl group bonded thereto.
  • Examples of the C1-6 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.
  • the C1-6 alkylene group is a divalent group formed by removing two hydrogen atoms from the C1-6 alkane.
  • Examples of the C1-6 alkylene group include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, and a propane-1,2-diyl group (that is, a propylene group).
  • the C1-6 alkylenedioxy group is a divalent group formed by replacing two hydrogen atoms in a C1-6 alkane with an oxy group.
  • Examples of the C1-6 alkylenedioxy group include a methylenedioxy group (—OCH 2 O—), an ethylenedioxy group (—OCH 2 CH 2 O—), and a trimethylenedioxy group.
  • Examples of the C6-10 aryl group substituted with a C1-6 alkylenedioxy group as G 2 include a 2,3-dihydro-benzo [1,4] dioxyl group, a benzo [1,3] dioxolyl group, and the like. Can do.
  • C1-6 haloalkyl group C2-6 haloalkenyl group, C2-6 haloalkynyl group, C1-6 haloalkoxy group, C1-6 haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, and C1
  • the -6 haloalkylenedioxy group includes the already described C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C1-6 alkoxy group, C1-6 alkylthio group, C1-6 alkylsulfinyl group, A halogeno group is substituted on the C1-6 alkylsulfonyl group and the C1-6 alkylenedioxy group.
  • C1-6 haloalkyl groups include fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2, Examples include 2,2-trifluoro-1-trifluoromethylethyl group, perfluorohexyl group, perchlorohexyl group, 2,4,6-trichlorohexyl group and the like.
  • Examples of the C2-6 haloalkenyl group include a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group.
  • Examples of the C2-6 haloalkynyl group include a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group.
  • C1-6 haloalkoxy groups include chloromethoxy, dichloromethoxy, difluoromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluoroethoxy, 2,2,2- Examples thereof include a trifluoroethoxy group, a pentafluoroethoxy group, and a 2,2,3,4,4,4-hexafluoro-butoxy group.
  • C1-6 haloalkylthio group, trifluoromethylthio group, 2,2,2-trifluoroethylthio group and the like can be mentioned.
  • Examples of the C1-6 haloalkylsulfinyl group include a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group.
  • Examples of the C1-6 haloalkylsulfonyl group include a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group.
  • Examples of the C1-6 haloalkylenedioxy group include a difluoromethylenedioxy group (—OCF 2 O—) and a tetrafluoroethylenedioxy group (—OCF 2 CF 2 O—).
  • Examples of the C6-10 aryl group substituted by the C1-6 haloalkylenedioxy group as G 2 include a 2,2,3,3-tetrafluoro-2,3-dihydro-benzo [1,4] dioxyl group, A 2,2-difluoro-benzo [1,3] dioxolyl group and the like can be mentioned.
  • the substituent G 21 represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a cyano group, a nitro group, or a halogeno group. These are as already described.
  • R 2 preferably C1 ⁇ 6 alkyl group substituted with unsubstituted or G 1, unsubstituted C1 ⁇ 6 alkyl group is more preferable.
  • R 3 is an unsubstituted or C 1-6 alkyl group substituted with G 1 (preferably a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group, or a halogeno group).
  • An unsubstituted C3-8 cycloalkyl group (preferably a C3-4 cycloalkyl group), an unsubstituted C6-10 aryl group (preferably a phenyl group), or a halogeno group, preferably unsubstituted or substituted with G 1 More preferred is a C1-6 alkyl group or a halogeno group.
  • R 4 is a hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C2 ⁇ 6 alkenyl group substituted with G 1, which is substituted by unsubstituted or G 1 C2 substituted 1-6 alkynyl group, an unsubstituted or C3 ⁇ 8 cycloalkyl group substituted with G 1, unsubstituted or C6 ⁇ 10 aryl C1 to 6 alkyl group substituted with G 2, unsubstituted or with G 2 3 to 10-membered heterocyclyl C1-6 alkyl group, formyl group, C1-6 alkylcarbonyl group which is unsubstituted or substituted with G 1 , C6-10 arylcarbonyl group which is unsubstituted or substituted with G 2 , unsubstituted or C1 ⁇ 6 alkoxycarbonyl group substituted with G 1, unsubstituted or C2
  • G a independently represents a hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C2 ⁇ 6 alkenyl group substituted with G 1, unsubstituted or with G 1 substituted C2 ⁇ 6 alkynyl group, a unsubstituted or C3 ⁇ 8 cycloalkyl group substituted by G 1 or unsubstituted or C6 ⁇ 10 aryl group substituted by G 2,.
  • G b represents a hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C2 ⁇ 6 alkenyl group substituted with G 1, which is substituted by unsubstituted or G 1 C2 2-6 alkynyl group, an unsubstituted or C3 ⁇ 8 cycloalkyl group substituted with G 1, unsubstituted or C6 ⁇ 10 aryl group substituted by G 2 3 or substituted with unsubstituted or G 2,
  • T is an oxygen atom, oxycarbonyl group, carbonyloxy group, oxycarbonyloxy group, sulfur atom, (thio) carbonyl group, carbonyl (thio) group, (thio) carbonyloxy group, oxycarbonyl (thio) group, or-
  • a divalent group represented by O—C ( ⁇ O) —N (G b ) — is shown.
  • R 4 a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C3-8 cycloalkyl group, a C1-6 alkylcarbonyl group, a C1-6 alkoxycarbonyl group, a C1-6 alkylsulfonyl group,
  • the substituent G 1 and the substituent G 2 are as described above.
  • the C6-10 aryl C1-6 alkyl group is a C1-6 alkyl group substituted with a C6-10 aryl group.
  • Examples of the C6-10 aryl C1-6 alkyl group include a benzyl group and a phenethyl group.
  • the 3- to 10-membered heterocyclyl C1-6 alkyl group is a C1-6 alkyl group substituted with a 3- to 10-membered heterocyclyl group.
  • the 3- to 10-membered heterocyclyl C1-6 alkyl group is preferably a 5- to 6-membered saturated heterocyclyl C1-6 alkyl such as tetrahydrofuranylmethyl group, tetrahydropyranylmethyl group, dioxolanylmethyl group, dioxanylmethyl group, etc. Groups; 5- to 6-membered heteroaryl C1-6 alkyl groups such as a pyrazolylmethyl group and a pyridylmethyl group.
  • the C6-10 arylcarbonyl group is a group in which a C6-10 aryl group is bonded to a carbonyl group. Examples of the C6-10 arylcarbonyl group include a benzoyl group.
  • Examples of the C2-6 alkenyloxycarbonyl group include a vinyloxycarbonyl group, a 1-propenyloxycarbonyl group, and a 2-propenyloxycarbonyl group (allyloxycarbonyl group).
  • Examples of the C1-6 alkylaminocarbonyl group include a methylaminocarbonyl group and a dimethylaminocarbonyl group.
  • Examples of the (C1-6 alkylthio) carbonyl group include (methylthio) carbonyl group and (ethylthio) carbonyl group.
  • Examples of the C1-6 alkylamino (thiocarbonyl) group include a methylamino (thiocarbonyl) group and a dimethylamino (thiocarbonyl) group.
  • the 3- to 10-membered heterocyclyl group for G b is preferably a 5- to 6-membered saturated heterocyclyl group or a 5- to 6-membered heteroaryl group.
  • Examples of the group represented by the formula (V) include the following.
  • R 4 represents a hydrogen atom, a C 1-6 alkyl group which is unsubstituted or substituted with G 1 (preferably a C 1-6 alkoxycarbonyl group, C 1-6 alkoxycarbonyloxy group), A C2-6 alkenyl group substituted or substituted with G 1 , an unsubstituted or C6-10 aryl C1-6 substituted with G 2 (preferably a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group) alkyl group, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1 (more preferably unsubstituted), unsubstituted or G 1 (preferably C1 ⁇ 6 alkoxy group, a halogeno group) substituted with C1 -6 alkoxycarbonyl group, C2-6 alkenyloxycarbonyl group unsubstituted or substituted with G 1 (more preferably unsubstituted), unsubstituted Or a C
  • [Q] Q represents any one of the organic groups represented by the formulas (II) to (IV). Note that * indicates the bonding position of the organic group represented by the formulas (II) to (IV).
  • R a is a hydrogen atom, an amino group, a C1-6 alkyl group which is unsubstituted or substituted with G 1 , or a C6-10 aryl which is unsubstituted or substituted with G 2 (preferably a C1-6 haloalkyl group) Indicates a group.
  • the C1-6 alkyl group, the C6-10 aryl group, the substituent G 1 and the substituent G 2 in R a are as described above.
  • R a is preferably a hydrogen atom or an unsubstituted or C 1-6 alkyl group substituted with G 1 .
  • the C1-6 alkyl group in R a is preferably unsubstituted.
  • A is unsubstituted or C1 ⁇ C6 alkylene group substituted with G 3, unsubstituted or C2 ⁇ C6 alkenylene group substituted with G 3, unsubstituted or C2 ⁇ C6 alkynylene group substituted with G 3 shows the unsubstituted or C1 ⁇ C6 alkylene group which is substituted by G 3, unsubstituted or is oxy C1 ⁇ C6 alkylene group substituted with G 3, unsubstituted C3 ⁇ C6 cycloalkylene group or a carbonyl group, .
  • the C1-C6 alkylene group for A is as described above.
  • the C2-C6 alkenylene group is a divalent group formed by removing two hydrogen atoms from the C2-C6 alkene.
  • Examples of the C2 to C6 alkenylene group include an ethenylene group, a propenylene group, and a butenylene group.
  • the C2-C6 alkynylene group is a divalent group formed by removing two hydrogen atoms from the C2-C6 alkyne.
  • Examples of the C2 to C6 alkynylene group include an ethynylene group, a propynylene group, a butynylene group, and the like.
  • Examples of the C1-C6 alkyleneoxy group include a methyleneoxy group (—CH 2 O—) and an ethyleneoxy group (—CH 2 CH 2 O—).
  • Examples of the oxy C1-C6 alkylene group include an oxymethylene group (—OCH 2 —) and an oxyethylene group (—OCH 2 CH 2 —).
  • the C3-C6 cycloalkylene group is a divalent group formed by removing two hydrogen atoms from a C3-C6 cycloalkane.
  • the C3-C6 cycloalkylene group includes a cyclopropylene group (1,2-cyclopropylene group), a cyclobutylene group (1,2-cyclobutylene group, or 1,3-cyclobutylene group), a cyclopentylene group (1 , 2-cyclopentylene group, or 1,3-cyclopentylene group), cyclohexylene group (1,2-cyclohexylene group, 1,3-cyclohexylene group, or 1,4-cyclohexylene group), etc.
  • it is a cyclopropylene group.
  • G 3 is a C1-6 alkyl group, C1-6 alkoxy group, formyl group, C1-6 alkylcarbonyl group, formyloxy group, C1-6 alkylcarbonyloxy group, halogeno group, C1-6 alkylene group, or oxo group Indicates.
  • the C1-6 alkyl group, C1-6 alkoxy group, C1-6 alkylcarbonyl group, C1-6 alkylcarbonyloxy group, halogeno group, and C1-6 alkylene group are as described above.
  • A is been C1 ⁇ C6 alkylene group (more preferably an unsubstituted) substituted with unsubstituted or G 3, unsubstituted or C2 ⁇ C6 alkenylene group substituted with G 3 (more preferably nothingness Substituted), unsubstituted or substituted C1-C6 alkyleneoxy groups with G 3 (more preferably unsubstituted), or unsubstituted C3-C6 cycloalkylene groups (more preferably unsubstituted).
  • it is more preferably a C1-C6 alkylene group (more preferably unsubstituted) substituted with G 3 .
  • Ar 1 represents an unsubstituted or C6 ⁇ 10 aryl group substituted by G 2 or unsubstituted or 3-10 membered heterocyclyl group which is substituted by G 2,.
  • the C6-10 aryl group, 3- to 10-membered heterocyclyl group, and substituent G 2 in Ar 1 are as described above.
  • Preferred examples of the 3- to 10-membered heterocyclyl group for Ar 1 include 5- to 10-membered heteroaryl groups such as a pyrazolyl group, a pyridyl group, a pyrimidinyl group, and a quinolinyl group.
  • Ar 1 is preferably an unsubstituted or C6 ⁇ 10 aryl group substituted by G 2 or unsubstituted or 5-6 membered heteroaryl group substituted with G 2, unsubstituted or more preferably a pyridyl group substituted with phenyl group or an unsubstituted or G 2 substituted with G 2.
  • G 2 in Ar 1 is more preferably a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, a C6-10 aryl group (preferably a phenyl group), and / or a halogeno group.
  • Ar 2 is unsubstituted or C6 ⁇ 10 aryl group substituted by G 2, unsubstituted or C6 ⁇ 10 aryloxy group which is substituted by G 2, C6 ⁇ 10 substituted with unsubstituted or G 2 aryl C1 ⁇ 6 alkoxy group, an unsubstituted or 3-10 membered heterocyclyl group which is substituted by G 2, unsubstituted or 3-10 membered heterocyclyloxy group substituted with G 2 or unsubstituted or G 2, A substituted 3- to 10-membered heterocyclylthio group is shown.
  • the C6-10 aryl group in Ar 2 is as described above, and is preferably a phenyl group.
  • the C6-10 aryloxy group in Ar 2 is as described above, and is preferably a phenoxy group.
  • the 3- to 10-membered heterocyclyl group in Ar 2 is as described above, preferably a 5- to 6-membered heteroaryl group, more preferably a thienyl group, a pyrazolyl group, a pyridyl group, or a pyrazinyl group. .
  • the 3- to 10-membered heterocyclyloxy group in Ar 2 is as described above, preferably a 5- to 6-membered heteroaryloxy group, more preferably a pyrazolyloxy group, a pyridyloxy group, a pyrazinyloxy group, a pyrimidinyloxy group. More preferably a pyridyloxy group, a pyrazinyloxy group, or a pyrimidinyloxy group.
  • the C6-10 aryl C1-6 alkoxy group in Ar 2 is as described above, and is preferably a phenyl C1-6 alkoxy group.
  • the 3- to 10-membered heterocyclylthio group in Ar 2 is obtained by substituting a 3- to 10-membered heterocyclyl group for the SH group.
  • the 3- to 10-membered heterocyclylthio group is preferably a 5- to 6-membered heteroarylthio group such as a pyrazolylthio group or a pyridylthio group, and more preferably a pyridylthio group.
  • Substituent G 2 is as described above, and preferably C 1-6 haloalkyl group, C 1-6 alkoxy group, C 1-6 alkoxy C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 2-6 alkynyl.
  • Ar 2 is preferably unsubstituted or C6 ⁇ 10 aryl group substituted by G 2, unsubstituted or C6 ⁇ 10 aryloxy group which is substituted by G 2, unsubstituted or G 2 (preferably halogeno group) C6 ⁇ 10 aryl C1 ⁇ 6 alkoxy group substituted by, unsubstituted or 3-10 membered heterocyclyl group which is substituted by G 2, 3-10 substituted with unsubstituted or G 2 A membered heterocyclyloxy group, or a 3 to 10 membered heterocyclylthio group (preferably a 5 to 6 membered heteroarylthio group) which is unsubstituted or substituted with G 2 (preferably a halogeno group and / or a C1-6 haloalkyl group) , More preferably a pyridylthio group).
  • B a is unsubstituted or C1 ⁇ C6 alkylene group substituted with G 4, unsubstituted or C2 ⁇ C6 alkenylene group substituted with G 4, unsubstituted or C2 ⁇ C6 alkynylene substituted with G 4 group, an unsubstituted or C3 ⁇ C6 cycloalkylene group substituted by G 4, unsubstituted or C4 ⁇ C6 cycloalkenylene group substituted with G 4 3 ⁇ 6 or of unsubstituted or substituted by G 4,
  • the group represented by a membered heterocyclylene group is shown.
  • C1 ⁇ C6 alkylene group, C2 ⁇ C6 alkenylene group, and C2 ⁇ C6 alkynylene radicals are those as already mentioned.
  • the C3-C6 cycloalkylene group is a divalent group formed by removing two hydrogen atoms from a C3-C6 cycloalkane.
  • the C3-C6 cycloalkylene group includes a cyclopropylene group (1,2-cyclopropylene group), a cyclobutylene group (1,2-cyclobutylene group, or 1,3-cyclobutylene group), a cyclopentylene group (1 , 2-cyclopentylene group, or 1,3-cyclopentylene group), cyclohexylene group (1,2-cyclohexylene group, 1,3-cyclohexylene group, or 1,4-cyclohexylene group), etc.
  • it is a cyclopentylene group or a cyclohexylene group.
  • the C4-C6 cycloalkenylene group is a divalent group formed by removing two hydrogen atoms from a C3-C6 cycloalkene.
  • the C4 to C6 cycloalkenylene group includes a cyclobutenylene group (1,2-cyclobutenylene group, 1,3-cyclobutenylene group, 1,3-cyclobutenylene group, or 3,4-cyclobutenylene group), cyclopentenylene group (1, 2-cyclopentenylene group, 1,3-cyclopentenylene group, 1,4-cyclopentenylene group or 1,5-cyclopentenylene group), cyclohexenylene group (1,2-cyclohexenylene group) A selenylene group, a 1,3-cyclohexenylene group, a 1,4-cyclohexenylene group, and the like. Among these, a cyclopentenylene group or a cyclohexenylene group is preferable.
  • a 3- to 6-membered heterocyclylene group is a divalent group formed by removing two hydrogen atoms from a heteroalicyclic compound.
  • the heteroalicyclic compound is a non-aromatic compound containing 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as constituent atoms of the ring.
  • Examples of the 3- to 6-membered heterocyclylene group include a 3- to 6-membered saturated heterocyclylene group or a 5- to 6-membered partially unsaturated heterocyclylene group.
  • Examples of the 3- to 6-membered heterocyclylene group include dioxolanylene group, dihydrofuranylene group, tetrahydrofuranylene group, pyrrolylene group, pyrrolidinylene group, pyrazolylene group, pyrazolidinylene group, imidazolylene group, imidazolidinylene group, oxazolidylene group, oxazolidinylene group Group, thiazolinylene group, thiazolidinylene group, isoxazolidinylene group, isothiazolidinylene group, dihydropyranylene group, tetrahydropyranylene group, piperidinylene group, piperazinylene group, morpholinylene group and the like.
  • the 3- to 6-membered heterocyclylene group a 5- to 6-membered saturated heterocyclylene group is preferable, and a dioxolanylene group, a tetrahydrofuranylene group, and a piperidinylene group are more preferable.
  • the 3-6 membered heterocyclylene group (preferably a 5-6 membered saturated heterocyclylene group, more preferably a piperidinylene group) may be a C1-6 alkylene group and may be bridged.
  • B a is preferably unsubstituted or C1 ⁇ C6 alkylene group substituted with G 4, unsubstituted or C2 ⁇ C6 alkenylene group substituted with G 4, unsubstituted or with G 4 substituted C3 ⁇ C6 cycloalkylene group, a unsubstituted or C4 ⁇ C6 cycloalkenylene group substituted with G 4 or unsubstituted or 3-6 membered heterocyclylene group substituted by G 4,, more preferably, unsubstituted or C1 ⁇ C6 alkylene group substituted by G 4, or shows a unsubstituted or C3 ⁇ C6 cycloalkylene group substituted with G 4.
  • G 4 is a C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 alkoxy C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group , C1 ⁇ 6 haloalkoxy group, C2 ⁇ 6 alkenyloxy group, an unsubstituted or C6 ⁇ 10 aryl group substituted by G 21, unsubstituted or 3-10 membered heterocyclyl group which is substituted by G 21, a cyano group , Halogeno group, C1-6 alkylene group, C1-6 alkylenedioxy group, oxo group, C3-8 cycloalkyl C1-6 alkyl group, unsubstituted or substituted with G 21 C6-10 aryl C1-6 alkyl group, an unsubstituted or C6 ⁇ 10 aryl C1 ⁇ 6 alkoxy group substituted by G 21, 3 ⁇ 10 membere
  • G 4 is C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 alkoxy C1-6 alkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group, C1 1-6 haloalkoxy group, C2 ⁇ 6 alkenyloxy group, an unsubstituted or C6 ⁇ 10 aryl group substituted by G 21, unsubstituted or 3-10 membered heterocyclyl group which is substituted by G 21, unsubstituted or 3-10 membered heterocyclyl C1 ⁇ 6 alkyl group substituted with G 21, C3 ⁇ 8 cycloalkyloxy C1 ⁇ 6 alkyl group, unsubstituted or C6 ⁇ 10 aryloxy C1 ⁇ 6 alkyl group substituted with G 21, Or an unsubstituted or G 21 -substituted 3- to 10-membered heterocyclyloxy C 1-6 alkyl group.
  • G 4 C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 alkoxy C1-6 alkyl group, C1-6 haloalkyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C1-6 alkoxy C1-6 alkoxy group, C1-6 alkylenedioxy group, C6-10 aryl group, C6-10 aryl C1-6 alkoxy group, 3-10 membered heterocyclyl group, halogeno group, C1-6 alkylene group, substituent G 2 , And the substituent G 21 is as described above.
  • the C6-10 aryl group in G 4 is preferably a phenyl group.
  • the 3- to 10-membered heterocyclyl group in G 4 is preferably a 5- to 6-membered heterocyclyl group, more preferably a tetrahydropyranyl group or a pyridyl group.
  • the substituent G 21 in G 4 preferably represents a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a halogeno group.
  • the C2-6 alkenyloxy group is a hydroxyl group substituted with a C2-6 alkenyl group.
  • Examples of the C2-6 alkenyloxy group include a vinyloxy group, a 1-propenyloxy group, and a 2-propenyloxy group (allyloxy group).
  • Examples of the C3-8 cycloalkyl C1-6 alkyl group include a cyclopropylmethyl group and a cyclopentylmethyl group, and a cyclopropyl C1-6 alkyl group and a cyclopentyl C1-6 alkyl group are preferable.
  • Examples of the C6-10 aryl C1-6 alkyl group include a benzyl group and a phenethyl group.
  • the 3- to 10-membered heterocyclyl C1-6 alkyl group is preferably a 5- to 6-membered saturated heterocyclyl C1-6 alkyl such as tetrahydrofuranylmethyl group, tetrahydropyranylmethyl group, dioxolanylmethyl group, dioxanylmethyl group, etc.
  • 5- to 6-membered heteroaryl C1-6 alkyl groups such as a pyrazolylmethyl group and a pyridylmethyl group.
  • a pyridyl C1-6 alkyl group, a tetrahydropyranyl C1-6 alkyl group, and a pyrazolyl C1-6 alkyl group are preferable.
  • Examples of the C3-8 cycloalkyloxy C1-6 alkyl group include a cyclopropyloxymethyl group and a cyclohexyloxymethyl group. Preferred are a cyclopropyloxy C1-6 alkyl group and a cyclohexyloxy C1-6 alkyl group.
  • Examples of the C6-10 aryloxy C1-6 alkyl group include a phenoxymethyl group and a naphthyloxymethyl group, and a phenoxy C1-6 alkyl group is preferable.
  • the 3- to 10-membered heterocyclyloxy C1-6 alkyl group is preferably a 5- to 6-membered heteroarylmethyl group such as a pyrazolyloxymethyl group and a pyridyloxymethyl group.
  • a pyridyloxy C1-6 alkyl group and a pyrazolyloxy C1-6 alkyl group are preferable.
  • a part of the substituent G 4 on B a may be bonded to a carbon atom on Ar 2 to form an unsubstituted or G 4 -substituted 5- to 6-membered ring.
  • the 5- to 6-membered ring include a cyclopentene ring, a cyclohexene ring, a tetrahydrofuran ring, a 1,3-dioxolane ring, a tetrahydropyran ring, and the like, preferably a cyclopentene ring, a tetrahydrofuran ring, and a tetrahydropyran ring.
  • T 1 represents an unsubstituted or G 2 -substituted C 6-10 aryl C 1-6 alkoxyimino-C 1-6 alkyl group, or a ferrocenyl-C 1-6 alkyl group.
  • An unsubstituted or G 2 substituted C6-10 aryl C1-6 alkoxyimino-C1-6 alkyl group is a C1-6 alkyl group that is unsubstituted or substituted with G 2 C6-10 aryl C1— A 6-alkoxyimino group is substituted.
  • the C6-10 aryl C1-6 alkoxyimino group is as described above.
  • C6-10 aryl C1-6 alkoxyimino-C1-6 alkyl group includes benzyloxyimino-methyl group, 1- (benzyloxyimino) -ethyl group, 2- (benzyloxyimino) -1-methylpropyl group, And 2-phenyl-1-methylpropoxyimino) -1-methylpropyl group.
  • the substituent G 2 in T 1 is as described above, and is preferably a C1-6 haloalkyl group or a C1-6 haloalkoxy group.
  • Examples of the ferrocenyl-C1-6 alkyl group include a ferrocenylmethyl group.
  • Q is preferably an organic group represented by formula (II) or formula (III).
  • R 1 , R 2 , R 3 , R 4 , A, R a , G 4 , and Ar 2 have the same meaning as in formula (I).
  • n represents an integer of 0 to 1.
  • R 1 in the formula (VI) is preferably an unsubstituted C1-6 alkyl group.
  • R 2 in the formula (VI) is preferably an unsubstituted C1-6 alkyl group.
  • R 3 in formula (VI) preferably represents an unsubstituted or G 1 -substituted C 1-6 alkyl group, an unsubstituted C 3-8 cycloalkyl group, or an unsubstituted C 6-10 aryl group.
  • G 1 in R 3 of the formula (VI) is as described above, and preferably represents a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group, or a halogeno group.
  • R 4 in formula (VI) is a hydrogen atom, a C1-6 alkyl group substituted with G 1 , an unsubstituted C1-6 alkylcarbonyl group, a C6-10 aryl C1-6 alkyl group substituted with G 2 , Or it is preferably an unsubstituted C1-6 alkoxycarbonyl group.
  • G 1 in R 4 of the formula (VI) is as described above, and preferably represents a C1-6 alkoxycarbonyl group, and G 2 represents a C1-6 alkoxy group.
  • R a in formula (VI) is preferably a hydrogen atom.
  • G 4 in the formula (VI) is preferably a C1-6 alkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 alkoxy group, or a C2-6 alkenyloxy group.
  • Ar 2 in formula (VI) is preferably a substituted or substituted C 6-10 aryl group substituted with G 2 (more preferably a phenyl group), an unsubstituted or substituted C 2-10 aryloxy group substituted with G 2 (More preferably a phenoxy group), an unsubstituted or G 2 -substituted 3- to 10-membered heterocyclyl group (more preferably a 5- to 6-membered heteroaryl group, even more preferably a pyridyl group or a pyrazolyl group), or A 3- to 10-membered heterocyclyloxy group (more preferably a 5- to 6-membered heteroaryloxy group, still more preferably a pyridyloxy group) which is unsubstituted or substituted with G 2 .
  • G 2 in Ar 2 of formula (VI) is as defined above, preferably, C1 ⁇ 6 haloalkyl group, a tri C1 ⁇ 6 alkyl silyl ethynyl group, C1 ⁇ 6 alkoxy group, C1 ⁇ 6 alkoxy C1 ⁇ 6 An alkoxy group, a C1-6 haloalkoxy group, or a halogeno group;
  • the pyridine compound according to the present invention includes hydrates, various solvates and crystal polymorphs. Furthermore, the pyridine compound according to the present invention includes stereoisomers based on asymmetric carbon atoms, double bonds and the like, mixtures thereof, and tautomeric organisms.
  • stereoisomer In the present invention, compounds represented by the same structural formula, but compounds having different spatial arrangements of atoms or substituents in the structure, for example, optical isomers, diastereoisomers, geometric isomers, etc. These stereoisomers are also included in the present invention.
  • the stereoisomer may be a single substance or a mixture.
  • the salt of the compound (I) according to the present invention is not particularly limited as long as it is an agro-horticulturally acceptable salt.
  • salts of inorganic acids such as hydrochloric acid and sulfuric acid
  • salts of organic acids such as acetic acid and lactic acid
  • salts of alkali metals such as lithium, sodium and potassium
  • salts of alkaline earth metals such as calcium and magnesium
  • iron and copper And salts of organic metals such as ammonia, triethylamine, tributylamine, pyridine, hydrazine, and the like.
  • the salt of compound (I) can be obtained from compound (I) by a known method.
  • the pyridine compound according to the present invention is not particularly limited by its production method.
  • the pyridine compound according to the present invention can be synthesized by combining known reaction steps. For example, it can be obtained by a production method including the following reaction steps.
  • a compound represented by formula (a) (hereinafter sometimes referred to as “compound (a)”) and a compound represented by formula (b) (hereinafter sometimes referred to as “compound (b)”).
  • compound (c) a compound represented by the formula (c)
  • R 1 to R 3 have the same meaning as in formula (I)
  • R 7 and R 8 each independently represents an alkyl group or the like.
  • the amount of compound (b) to be used is generally 0.5 to 2 mol, preferably 0.7 to 1.5 mol, per 1 mol of compound (a).
  • the synthesis reaction of compound (c) may be performed without a solvent or in a solvent.
  • the solvent used in this reaction is not particularly limited as long as it is inert to the reaction.
  • ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran
  • aromatic hydrocarbon solvents such as toluene, benzene and xylene
  • aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvent
  • Halogenated hydrocarbon solvent such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane
  • Amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone
  • examples thereof include nitrile solvents such as acetonitrile and benzonitrile; alcohol solvents such as methanol, ethanol and n-prop
  • compound (d) and the compound represented by the formula (d) (hereinafter sometimes referred to as “compound (d)”) or the compound represented by the formula (d ′) (hereinafter referred to as “compound ( d ′) ”may be reacted to produce a compound represented by the formula (e) (hereinafter also referred to as“ compound (e) ”).
  • R 1 to R 3 and R 7 have the same meaning as described above.
  • R 4 has the same meaning as in formula (I)
  • L represents a leaving group such as a halogen atom.
  • R a and A have the same meaning as in formula (II), (III) or (IV).
  • the amount of compound (d) or compound (d ′) to be used is generally 0.5 to 2 mol, preferably 0.7 to 1.5 mol, per 1 mol of compound (c).
  • This reaction can be carried out in a solvent.
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran
  • aromatic hydrocarbon solvents such as toluene, benzene and xylene
  • aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvent
  • Halogenated hydrocarbon solvent such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane
  • Amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone
  • nitrile solvents such as acetonitrile and benzonitrile
  • alcohol solvents such as methanol, ethanol and n-propanol
  • the amount of the solvent to be used is not particularly limited, but is usually 1 to 100 ml with respect to 1 g of compound (c).
  • Base catalysts include triethylamine, diisopropylethylamine, pyridine, 1,2-diazabicyclo [2,2,2] octane (DABCO), 4-dimethylaminopyridine (DMAP), 1,2-diazabiniclo [5,4,0].
  • Organic bases such as unde-7-ene (DBU) can be used.
  • the amount of the base catalyst to be used is generally 0.1 to 10 mol per 1 mol of compound (c).
  • the reaction temperature is a temperature range from room temperature to the boiling point of the solvent used.
  • the reaction time is usually several minutes to several tens of hours depending on the reaction scale.
  • compound (f) a compound represented by the formula (f) (hereinafter sometimes referred to as “compound (f)”).
  • the reducing agent lithium aluminum hydride, sodium borohydride, diisobutylaluminum hydride and the like can be used. This reduction reaction can be carried out in a solvent.
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran
  • aromatic hydrocarbon solvents such as toluene, benzene and xylene
  • aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvent
  • Halogenated hydrocarbon solvent such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane
  • Amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone
  • nitrile solvents such as acetonitrile and benzonitrile
  • alcohol solvents such as methanol, ethanol and n-propanol
  • the amount of the solvent to be used is not particularly limited, but is usually 1 to 100 ml with respect to 1 g of compound (e).
  • the temperature of the reduction reaction is in the temperature range from ⁇ 78 ° C. to the boiling point of the solvent used.
  • the reaction time is usually several minutes to several tens of hours depending on the reaction scale.
  • the compound (f) is oxidized to obtain a compound represented by the formula (g) (hereinafter sometimes referred to as “compound (g)”).
  • the oxidizing agent chromium oxide, dichromic acid, chromate ester, pyridinium chlorochromate, manganese dioxide, or the like can be used. This oxidation reaction can be carried out in a solvent.
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran
  • aromatic hydrocarbon solvents such as toluene, benzene and xylene
  • aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvent
  • Halogenated hydrocarbon solvent such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane
  • Amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone
  • nitrile solvents such as acetonitrile and benzonitrile
  • the amount of the solvent to be used is not particularly limited, but is usually 1 to 100 ml with respect to 1 g of compound (f).
  • the temperature of the oxidation reaction is a temperature range from room temperature to the boiling point of the solvent used.
  • the reaction time is usually several minutes to several tens of hours depending on the reaction scale.
  • compound (2) a compound represented by the formula (2) (hereinafter sometimes referred to as “compound (2)”).
  • the compound represented by the formula (2) is useful as a production intermediate for producing the compound represented by the formula (I) and its N-oxide or a salt thereof.
  • Carbon increase reactions include (methoxymethyl) triphenylphosphonium chloride, (methoxymethyl) triphenylphosphonium bromide, O, O-diethyl (cyanomethyl) phosphonate, O, O-diethylphosphonoacetic acid methyl ester, (2,2-dimethoxy) Ethyl) -phosphoric acid diethyl ester, diethyl phosphonoacetic acid ethyl ester, diethyl (2,2-diethoxyethyl) phosphonate, (1,3-dioxolan-2-ylmethyl) -phosphoric acid diethyl ester, diethoxy methoxymethyl phosphonate, etc.
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran
  • aromatic hydrocarbon solvents such as toluene, benzene and xylene
  • aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvents
  • Amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone; and mixed solvents composed of two or more of these solvents.
  • the amount of the solvent to be used is not particularly limited, but is usually 1 to 100 ml with respect to 1 g of compound (g).
  • This carbon increase reaction is preferably performed in the presence of a base.
  • a base an alkali metal base such as sodium hydride, sodium methoxide, sodium ethoxide, potassium t-butoxide and the like can be used.
  • the amount of the base to be used is generally 1 to 10 mol per 1 mol of compound (g).
  • the reaction temperature is in the temperature range from ⁇ 78 ° C. to the boiling point of the solvent used.
  • the reaction time is usually several minutes to several tens of hours depending on the reaction scale.
  • compound (h) the compound represented by the formula (1)
  • compound (h) is reacted with the compound represented by the formula (1) (hereinafter referred to as “compound (h)”).
  • compound (1) is reacted with the compound represented by the formula (1) (hereinafter referred to as “compound (1)”).
  • R 1 to R 4 , R a and A have the same meaning as described above.
  • R 6 has the same meaning as Ar 1 , Ar 2 -B a , or T 1 in formula (II), (III), or (IV).
  • the amount of compound (h) to be used is generally 0.5 to 2 mol, preferably 0.7 to 1.5 mol, per 1 mol of compound (2).
  • the synthesis reaction of the compound (1) can be carried out in the absence of a catalyst, but is preferably carried out in the presence of an acid catalyst or a base catalyst, more preferably in the presence of an acid catalyst.
  • the acid catalyst include trifluoroacetic acid, benzenesulfonic acid, p-toluenesulfonic acid, p-toluenesulfonic acid monohydrate, methanesulfonic acid, pyridinium p-toluenesulfonate, hydrochloric acid, sulfuric acid, and the like.
  • the base catalyst include pyridine, triethylamine, potassium hydroxide and the like.
  • the amount of the catalyst to be used is generally 0.0001-1 mol per 1 mol of compound (2).
  • a dehydrating agent such as anhydrous sodium sulfate or molecular sieve may be added to the reaction system.
  • the synthesis reaction of the compound (1) can be performed in a solvent.
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran
  • aromatic hydrocarbon solvents such as toluene, benzene and xylene
  • aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvent
  • Halogenated hydrocarbon solvent such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane
  • Amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone
  • examples thereof include nitrile solvents such as acetonitrile and benzonitrile; alcohol solvents such as methanol, ethanol and n-propanol; and mixed solvents composed of
  • the amount of the solvent to be used is not particularly limited, but is usually 1 to 100 ml with respect to 1 g of compound (2).
  • the reaction temperature is a temperature range from room temperature to the boiling point of the solvent used.
  • the reaction time is usually several minutes to several tens of hours depending on the reaction scale.
  • the salt of the compound (I) according to the present invention can be obtained from the compound represented by the formula (I) by a known method.
  • the product can be purified after completion of the reaction.
  • purification means include distillation, recrystallization, and column chromatography.
  • the structure of the target product can be identified and confirmed by 1 H-NMR spectrum, IR spectrum, mass spectrum, elemental analysis and the like.
  • Some intermediates produced in the production process of the compound of the present invention exhibit bactericidal activity.
  • the pyridine compound according to the present invention has effects such as pest control, sterilization, acaricide, and insecticide, it is useful as an agricultural and horticultural fungicide, a pest control agent, and an insecticide or acaricide active ingredient. It is a highly safe compound because it has little phytotoxicity and low toxicity to fish and warm-blooded animals.
  • the agricultural and horticultural fungicide, pesticide, and insecticide or acaricide of the present invention are effective at least one selected from the compound (I) or a salt thereof (hereinafter sometimes referred to as “the present compound”). It is contained as a component.
  • the agricultural and horticultural fungicides of the present invention belong to a wide variety of filamentous fungi, for example, algae (Oomycetes), Ascomycetes, Deuteromycetes, and Basidiomycetes Has excellent bactericidal power against bacteria.
  • algae Olemycetes
  • Ascomycetes Ascomycetes
  • Deuteromycetes Deuteromycetes
  • Basidiomycetes Has excellent bactericidal power against bacteria.
  • Cucumber powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine split disease (Fusarium oxysporum), mycotic disease (Sclerotinia sclerotiorum), gray mold disease (Botrytiscine , Anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassicola), seedling blight (Pythium debaryanam, Rhizoctonia solani Kuhn), spot bacterial disease (Pseudomonas syringae pv.
  • Gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans), half body wilt (Verticillium albo-atrum), etc.
  • Eggplant Gray Mold disease (Botrytis cinerea), black blight disease (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), subtilis disease (Mycovellosiella nattrassii), mycorrhizal disease (Sclerotinia sclerotiorum), etc.
  • Apples powdery mildew (Podosphaera leucotricha), black spot disease (Venturia inaequalis), monilinia disease (Monilinia mali), black spot disease (Mycosphaerella pomi), rot disease (Valsa mali), spotted leaf disease (Alternaria mali), red star disease (Gymnosporang) yamadae), ring rot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), soot spot (Zygophiala jamaicensis), soot spot (Gloeodes pomigena), purple coat rot (Helicobasidium mompa), etc.
  • Oysters powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), keratodeciduous leaf disease (Cercospora kaki), etc.
  • Peach Monilinia fructicola, black scab (Cladosporium carpophilum), homoposis Rot disease (Phomopsis sp.), Perforated bacterial disease (Xanthomonas campestris pv. Pruni), etc.
  • Auto Monilinia fructicola, anthracnose (Colletotrichum acutatum), etc.
  • Grapes Gray mold Diseases (Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black scab (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black Rot (Guignardia bidwellii), etc.
  • Pear Venturia nashicola, Red rot (Gymnosporangium asiaticum), Black spot (Alternaria kikuchiana), Ring rot (Botryosphaeria berengeriana), Powdery mildew (Phyllactinia mali), Body blight (Phomopsis fukushii), brown spot disease (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Cha: ring spot disease (Pestalotia theae), anthracnose (Colletotrichum theae-sinensis), etc.
  • Blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), sunspot (Diaporthe citri), scab (Xanthomonas campestris pv.Citri), etc.
  • Rice blast (Pyricularia oryzae) Disease (Rhizoctonia solani), idiot seedling disease (Gibberella fujikuroi), sesame leaf blight (Cochliobolus miyabeanus), seedling blight (Pythium graminicolum), white leaf blight (Xanthomonas oryzae), seedling blight (Burkholderia plantarii), Brown stripe disease (Acidovorax avenae), bacterial blast blight (Burkholderia glumae), leaf blight (Cercospora oryzae), rice rot (Ustilaginoidea virens), brown rice (Alternaria alternata, Curvularia intermedia), black rice (Alternaria padwickii), red rice ( Epicoccam purpurascenns, etc.
  • Tobacco Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), etc.
  • Tulip Gray mold, Botrytis cinerea, etc.
  • Dollar spot Sclerotinia homoeocarpa
  • blast Pyricularia sp.
  • Red fire Pythium aphanidermatum
  • anthracnose Colletotrichum graminicola
  • Orchardgrass powdery mildew (Erysiphe graminis), etc.
  • Soybean Purple spot (Cercospora) kikuchii), downy mildew (Peronospora Manshurica), stem blight (Phytophthora sojae), rust (Phakopsora pachyrhizi), mycorrhizal disease (Sc) lerotinia sclerotiorum, anthracnose (Colletotrichum truncatum), etc.
  • Potato Phytophthora infestans, etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola), etc. Decay disease (Phoma lingam), black spot disease (Alternaria brassicae), etc.
  • the insecticide or acaricide of the present invention is excellent in the effect of controlling various pests such as various agricultural pests and mites that affect plant growth.
  • the insecticide or acaricide of the present invention is effective not only for susceptible strains but also for pests of strains that have developed resistance to conventional agents such as organophosphorus agents and carbamate agents.
  • Representative examples of pests of resistant strains include goldfish, planthopper, leafhopper, aphid and the like.
  • the pest control agent of the present invention is effective for controlling pests other than agricultural pests and mites.
  • pests include ectoparasites and sanitary pests.
  • Plants that can be targeted by the agricultural and horticultural fungicides, pesticides, and insecticides or acaricides of the present invention include cereals, vegetables, root vegetables, potatoes, trees, grasses, grasses, etc. Is mentioned.
  • the agricultural and horticultural fungicides, pesticides, and insecticides or acaricides of the present invention are plant parts such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprout, roots, tubers, It can be applied to tuberous roots, shoots and cuttings.
  • improved varieties and varieties of these plants, cultivated varieties, and mutants, hybrids, and genetically modified organisms (GMO) can also be targeted.
  • the agricultural and horticultural fungicide of the present invention should be used for seed treatment, foliage application, soil application, water surface application, etc. for controlling various diseases occurring in agricultural and horticultural crops including flower buds, turf, and grass. Can do.
  • Agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides of the present invention are agricultural and horticultural fungicides that have other effects such as bactericidal, insecticidal / miticidal, nematicidal, soil-killing pests, etc.
  • Agricultural and horticultural agents; plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. may be used in combination or in combination. An example is shown below.
  • Fungicide (1) Nucleic acid biosynthesis inhibitors: (A) RNA polymerase I inhibitor: benalaxyl, benalaxyl-M, furaxyl, metalaxyl, metalaxyl-M; oxadixil; cloziracone, off-race; (B) Adenosine deamylase inhibitor: bupilimate, dimethylylmol, ethylimol; (C) DNA / RNA synthesis inhibitors: Himexazole, octirinone; (D) DNA topoisomerase II inhibitor: oxophosphate; (2) Mitotic fission inhibitor and cell division inhibitor: (A) ⁇ -tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; dietofencarb; zoxamide; ethaboxam; (B) Cell division inhibitor:
  • Cell membrane sterol biosynthesis inhibitors (A) Demethylation inhibitor at the C14 position in sterol biosynthesis: Trifolin; Triflumizole, biniconazole; Azaconazole, viteltanol, bromconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriazole), fluconazole, fluconazole- Cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, quinconazole, cimeconazole, tebuconazole, tetraconazole, triadimethone, triadimenol, triticonazole; prothio
  • Agents with unknown activity Simoxanyl, fosetylaluminum, phosphoric acid (phosphate), teclophthalam, triazoxide, fursulfamide, dichromedin, metasulfocarb, cyflufenamide, metolaphenone, pyriophenone, dodin, dodin free base, fluthianyl; (12) Agents with multiple action points: copper (copper salt), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; farbum, mancozeb, maneb) , Mancopper, methylam, polycarbamate, propineb, thiram, dineb, ziram; captan, captahol, phorpet; chlorothalonil; dicloflurane, tolylfluanid; Quinomethionate; fluorimide; (13) Other agents: DBEDC, fluorophorpet,
  • Acetylcholinesterase inhibitor (A) Carbamate series: alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxym, butoxycarboxym, carbaryl, carbofuran, carbosulfan, etiophencarb, fenobucarb, formethanate, furthiocarb, isoprocarb, methiocarb, mesomil, oxamyl, pirimicarb, propoxycarb Thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb; phenothiocarb, MIPC, MPMC, MTMC, aldoxicarb, alixicarb, aminocarb, bufencarb, cloetocarb, metam sodium, promecarb; (B) Organophosphorus: Ace
  • GABA-agonist chloride channel antagonists chlordane, endosulfan, etiprole, fipronil, pyrafluprole, pyriprole; camfechlor, heptachlor; (3) Sodium channel modulators: Acrinatrin, d-cis-trans allethrin, d-transarethrin, bifenthrin, bioaresulin, bioareslin isomers, violesmethrin, cycloprotorin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- Cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, ciphenothrin [(1R) -trans isomer], delta
  • Juvenile hormone-like substances hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; geofenolan, epofenonane, triprene; (8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar; (9) Homoptera selective feeding inhibitor: flonicamid, pymetrozine; (10) Mite growth inhibitor: clofentezin, diflovidazine, hexythiazox, etoxazole; (11) Microbial-derived insect midgut mesentery: Bacillus thuringiensis subsp.
  • Chitin synthesis inhibitor bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, nobarulone, nobiflumuron, teflubenzuron, triflumuron, buprofezin;
  • Diptera molting disruptors cyromazine;
  • Molting hormone receptor agonists Chromafenozide, halofenozide, methoxyphenozide, tebufenozide;
  • Octopamine receptor agonist Amitraz;
  • Mitochondrial electron transport system complex III inhibitor acequinosyl, fluacrylpyrim, hydramethylnon;
  • Mitochondrial electron transport system complex I inhibitor phenazaquin, fenproxymate, pyrimidifen, pyridaben, tebufenpyrad, tol
  • the agricultural and horticultural fungicide, pest control agent, and insecticide or acaricide of the present invention are not particularly limited depending on the dosage form.
  • Examples include dosage forms such as wettable powders, emulsions, aqueous solvents, granular wettable powders, powders, and tablets.
  • the preparation method to a formulation is not specifically limited, A well-known preparation method can be employ
  • the pharmaceutical formulation is shown slightly, but the additives and addition ratios are not limited to these examples, and can be varied in a wide range.
  • the part in a formulation prescription shows a mass part.
  • Formulation 1 wettable powder
  • Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate 4 parts Alkyl naphthalene sulfonate 3 parts The above components were mixed uniformly and finely pulverized to obtain a wettable powder of 40% active ingredient.
  • Formulation 3 Granules
  • Compound of the present invention 5 parts Talc 40 parts Clay 38 parts Bentonite 10 parts Sodium alkyl sulfate 7 parts
  • the above ingredients are uniformly mixed and finely pulverized, then granulated into granules having a diameter of 0.5 to 1.0 mm, and the active ingredient is 5%. Get the granules.
  • Formulation 4 Granules
  • Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctylsulfosuccinate sodium salt 1 part Potassium phosphate 1 part
  • the above components are pulverized and mixed well, water is added and kneaded, granulated and dried, and then 5% active ingredient. Get the granules.
  • the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.70 g of the target compound. Yield 90%.
  • the mixture was extracted with dichloromethane, washed with an aqueous sodium thiosulfate solution and saturated brine, and the organic layer was dried over anhydrous magnesium sulfate.
  • the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 11.1 g of the objective compound. Yield 99%.
  • the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.25 g of the target compound. Yield 49%.
  • Tables 1 to 8 and Table 10 Compounds prepared by the same method as in the above examples are shown in Tables 1 to 8 and Table 10.
  • the physical property data of the compounds are described in the “Physical Properties” column.
  • melting point (° C.), refractive index (nD), or properties thereof are described.
  • Table 1 shows compounds represented by formula (I) in which Q is an organic group represented by formula (II) (compound represented by formula (I-1) shown below).
  • the compounds described in Table 1 are compounds in which R 1 , R 2 , and R 3 are methyl groups.
  • “E” shown in “stereoconfiguration” indicates that the double bond of imine in the compound is E configuration.
  • “Z” indicates a Z configuration.
  • EZ indicates that the compound is a mixture of compounds in both configurations (the same meaning is given in the following tables).
  • Ph represents a phenyl group.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Ac represents an acetyl group (the same meaning is shown in the following tables).
  • Tables 2 to 8 are compounds represented by formula (I), wherein Q is an organic group represented by formula (III) (shown by formula (I-2) shown below) Compound).
  • the compounds listed in Table 2 are compounds in which R 1 , R 2 , and R 3 are methyl groups.
  • the carbon marked with * in the structural formula in “B a ” represents carbon bonded to oxygen of the oxime (the same meaning is shown in the following tables).
  • the carbon marked with ** in the structural formula of “B a ” of the compound 2-186 and the compound 2-187 represents a carbon bonded to “Ar 2 ”.
  • “Trans” shown in “stereoconfiguration” indicates that the 1,4-cyclohexylene group in the compound is in the trans configuration.
  • n Pr represents an n-propyl group
  • i Pr represents an isopropyl group
  • c Pr represents a cyclopropyl group
  • c Pen represents a cyclopentyl group
  • c Hex represents a cyclohexyl group (hereinafter referred to as a cyclohexyl group). The same meaning is also shown in the table).
  • the compounds listed in Table 3 are compounds in which R 1 , R 2 , and R 3 are methyl groups.
  • N Bu in the table represents an n-butyl group (the same meaning is given in the following tables).
  • the compounds listed in Table 4 are compounds in which R 1 , R 2 , and R 3 are methyl groups.
  • the oxygen marked with * in the structural formula in “A” indicates that it binds to the pyridine ring (the same meaning is shown in the following tables).
  • “E, EZ” shown in “stereoconfiguration” indicates that the compound is a mixture of a compound in which the ethynylene group in “A” is in the E configuration and the imine double bond is in the E configuration and a compound in the Z configuration. .
  • the carbons marked with ** in the structural formulas of “B a ” of Compound 5-19 and Compound 5-48 represent carbons bonded to “Ar 2 ”.
  • “Trans” shown in “stereoconfiguration” indicates that the 1,3-cyclopentylene group, 1,3-cyclohexylene group or 1,4-cyclohexylene group in the compound is in the trans configuration.
  • “Cis” indicates that a 1,3-cyclopentylene group, a 1,3-cyclohexylene group or a 1,4-cyclohexylene group is in a cis configuration (the same meaning is given in the following tables). .
  • Table 10 shows compounds represented by formula (I) in which Q is an organic group represented by formula (IV) (compound represented by formula (I-3) shown below). Disclose.
  • the compounds listed in Table 10 are compounds in which R 1 , R 2 , and R 3 are methyl groups.
  • Table 11 shows 1 H-NMR data for some of the compounds described in Tables 1 to 8 and 10 above.
  • Test Example 1 Wheat powdery mildew control test First, 95 parts by mass of dimethylformamide containing 1.5% by mass of polyoxyethylene sorbitan monolaurate and 5 parts by mass of the compound of the present invention were mixed and dissolved to obtain an active ingredient. A 5% emulsion was prepared. The above-mentioned emulsion was diluted with water containing 0.02% by mass of polyoxyethylene sorbitan monolaurate so that the compound concentration was 100 ppm to prepare a test drug solution.
  • the test chemical solution was sprayed on wheat seedlings (variety “Chihoku”, 1.0-1.2 leaf stage) cultivated in an unglazed pot.
  • wheat seedlings variety “Chihoku”, 1.0-1.2 leaf stage
  • conidia of wheat powdery mildew Erysiphe graminis f. Sp. Tritici
  • the seedlings of wheat powdery mildew fungus were shaken off and inoculated on the leaves of wheat seedlings (variety “Chihoku”, 1.0-1.2 leaf stage) grown in an unglazed pot without spraying the test chemical solution.
  • Test Example 2 Wheat red rust control test The emulsion described in Test Example 1 was diluted with water containing 0.02% by mass of polyoxyethylene sorbitan monolaurate so that the compound concentration was 100 ppm, and the test was performed. A drug solution was prepared. Subsequently, the test chemical solution was sprayed on wheat seedlings (variety “Noribayashi No. 61”, 1.0 to 1.2 leaf stage) cultivated in an unglazed pot. After air-drying the leaves, summer spores of wheat red rust fungus (Puccinia recondita) were shaken off and inoculated in a greenhouse at 22-25 ° C. for 10 days. In the same manner as in Test Example 1, the lesion appearance state on the leaves was compared with no treatment to determine the control effect. As a result, the compounds shown in Table 13 below exhibited an excellent control value of 75% or more.
  • Test Example 3 Efficacy Confirmation Test for Lotus Spodoptera
  • 5 parts by mass of the compound of the present invention, 93.6 parts by mass of dimethylformamide, and 1.4 parts by mass of polyoxyethylene alkylaryl ether were mixed and dissolved, and the active ingredient was 5%.
  • An emulsion was prepared. The emulsion was diluted with water to a compound concentration of 125 ppm. Cabbage leaves were dipped in the chemical solution for 30 seconds, air-dried, placed in a petri dish with filter paper, and 5 second-instar larvae of Spodoptera litura were inoculated.
  • the glass lid was put on and placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. After 5 days, the survival was examined and the insecticidal rate was determined. The test is duplicated. As a result, the compounds shown in Table 14 below showed an insecticidal rate of 100%.
  • Test Example 6 Efficacy test against Acacia toyo 0.2 ml of commercially available artificial feed (Insector LFS, manufactured by Nippon Nosan Kogyo Co., Ltd.) was packed in a plastic test tube (1.4 ml volume) to prepare test materials.
  • the emulsion described in (Test Example 3) was diluted with water so that the compound concentration was 125 ppm, and the chemical solution was dropped onto the feed surface in an amount equivalent to 10 ⁇ g of the compound.
  • Two instar larvae were inoculated per test tube and sealed with a plastic lid. The specimen was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. As a result, the compounds shown in Table 17 below showed an insecticidal rate of 100%.
  • Test Example 7 Efficacy test against bean aphids
  • Adult bean aphids were released on large square beans that had been sown in 3-inch pots and 10 days after germination. After 1 day, the 1st instar nymphs that were born were left and the adults were removed.
  • the emulsion described in (Test Example 3) was diluted with water so that the compound concentration was 125 ppm, and the chemical solution was sprayed onto the large square beans. Thereafter, the large angle beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%, and the survival of the bean aphid was examined after 5 days to determine the insecticidal rate. As a result, the compounds shown in Table 18 below showed an insecticidal rate of 80% or more.
  • Test Example 8 Efficacy test against Kanzawa spider mite Five adult female Kanzawa spider mites were released on the primary leaves 7 to 10 days after germination of mung beans seeded in a 3-inch pot. The emulsion described in Test Example 3 was diluted with water so that the compound concentration was 125 ppm, and the chemical solution was sprayed on the mung beans. Thereafter, the mung beans were placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. As a result, the compounds shown in Table 19 below showed an insecticidal rate of 80% or more.
  • the pyridine compound according to the present invention is a novel compound that has effects such as pest control, bactericidal, acaricidal, insecticidal and the like, does not cause phytotoxicity on plants, and has little toxicity to human fish and environmental impacts. . In particular, it exhibits an excellent control effect against wheat diseases.
  • the pyridine compound according to the present invention is useful as an active ingredient of agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides.

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

Abstract

La présente invention permet d'obtenir un composé représenté par la formule (I) ou un sel correspondant. La présente invention permet également d'obtenir un fongicide agricole et horticole, un agent de lutte contre les organismes nuisibles ou un pesticide ou un acaricide, qui contient en tant que constituant efficace correspondant au moins un composé choisi dans un groupe comprenant ledit composé et un sel correspondant. Dans la formule (I), R1 représente un atome d'hydrogène, R2 et R3 représentent chacun indépendamment un groupe alkyle, etc., R4 représente un atome d'hydrogène, etc. et Q représente un des groupes organiques représentés par les formules (II-IV). Dans les formules (II-IV), Ar1 et Ar2 représentent un groupe aryle, etc., Ra représente un atome d'hydrogène, etc., A représente un groupe alkylène, etc., Ba représente un groupe alkylène, etc., T1 représente un groupe arylalcoxyiminoalkyle non substitué ou substitué par G2 et * représente la position de liaison pour le groupe organique indiqué par les formules (II-IV).
PCT/JP2015/052938 2014-02-05 2015-02-03 Composé de pyridine et son application WO2015119099A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019083007A1 (fr) * 2017-10-27 2019-05-02 住友化学株式会社 Composé pyridine, et agent de lutte contre les arthropodes nuisibles comprenant celui-ci
WO2019083008A1 (fr) * 2017-10-27 2019-05-02 住友化学株式会社 Composé pyridine, et composition de lutte contre des organismes nuisibles comprenant celui-ci

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JPH11315057A (ja) * 1998-02-10 1999-11-16 Rohm & Haas Co 不飽和オキシムエ―テル
JP2000247962A (ja) * 1999-02-26 2000-09-12 Sumitomo Chem Co Ltd イソキサゾロン誘導体およびその用途
JP2001506984A (ja) * 1996-11-26 2001-05-29 イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー メチル置換された殺菌・殺カビ剤および殺節足動物剤
WO2006125637A1 (fr) * 2005-05-25 2006-11-30 Basf Aktiengesellschaft Composes de type ether d'oxime o-(phenyl/heterocyclyl)methylique servant a lutter contre les animaux nuisibles
CN1927817A (zh) * 2005-09-08 2007-03-14 沈阳化工研究院 一种1－(多取代)苯基环丙烷类化合物及其应用
WO2010137302A1 (fr) * 2009-05-27 2010-12-02 日本曹達株式会社 Dérivés hétéroaryles contenant de l'azote et fongicides pour utilisation agricole et horticole

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Publication number Priority date Publication date Assignee Title
JP2001506984A (ja) * 1996-11-26 2001-05-29 イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー メチル置換された殺菌・殺カビ剤および殺節足動物剤
JPH11315057A (ja) * 1998-02-10 1999-11-16 Rohm & Haas Co 不飽和オキシムエ―テル
JP2000247962A (ja) * 1999-02-26 2000-09-12 Sumitomo Chem Co Ltd イソキサゾロン誘導体およびその用途
WO2006125637A1 (fr) * 2005-05-25 2006-11-30 Basf Aktiengesellschaft Composes de type ether d'oxime o-(phenyl/heterocyclyl)methylique servant a lutter contre les animaux nuisibles
CN1927817A (zh) * 2005-09-08 2007-03-14 沈阳化工研究院 一种1－(多取代)苯基环丙烷类化合物及其应用
WO2010137302A1 (fr) * 2009-05-27 2010-12-02 日本曹達株式会社 Dérivés hétéroaryles contenant de l'azote et fongicides pour utilisation agricole et horticole

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019083007A1 (fr) * 2017-10-27 2019-05-02 住友化学株式会社 Composé pyridine, et agent de lutte contre les arthropodes nuisibles comprenant celui-ci
WO2019083008A1 (fr) * 2017-10-27 2019-05-02 住友化学株式会社 Composé pyridine, et composition de lutte contre des organismes nuisibles comprenant celui-ci

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