WO2015199065A1 - Compose pyridine et son utilisation - Google Patents

Compose pyridine et son utilisation Download PDF

Info

Publication number
WO2015199065A1
WO2015199065A1 PCT/JP2015/068009 JP2015068009W WO2015199065A1 WO 2015199065 A1 WO2015199065 A1 WO 2015199065A1 JP 2015068009 W JP2015068009 W JP 2015068009W WO 2015199065 A1 WO2015199065 A1 WO 2015199065A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
unsubstituted
substituted
alkyl
alkoxy
Prior art date
Application number
PCT/JP2015/068009
Other languages
English (en)
Japanese (ja)
Inventor
岩田　淳
一成 加登
元亮 佐藤
信也 植薄
藤井　聡
朝巳 小林
伸哉 幸堀
貴昭 寺西
Original Assignee
日本曹達株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 日本曹達株式会社 filed Critical 日本曹達株式会社
Priority to JP2016529594A priority Critical patent/JP6508540B2/ja
Publication of WO2015199065A1 publication Critical patent/WO2015199065A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—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
    • A01N47/06—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 containing —O—CO—O— groups; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4409—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 4, e.g. isoniazid, iproniazid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/502—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with carbocyclic ring systems, e.g. cinnoline, phthalazine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring

Definitions

  • the present invention relates to pyridine compounds and uses such as agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides.
  • 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 is hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C1 ⁇ 6 alkoxy group substituted with G 1, which is substituted by unsubstituted or G 2 C6 ⁇ 10 aryl group, unsubstituted or G 2 -substituted 3- to 6-membered heterocyclyl group, cyano group or halogeno group.
  • R 2 and R 3 are each independently a hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C3 ⁇ 8 cycloalkyl group substituted by G 1, the unsubstituted or C1 ⁇ 6 alkoxy group substituted by G 1, a formyl group, a formyloxy group, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, C1 is substituted by unsubstituted or G 1 ⁇ 6 alkylcarbonyloxy group, an unsubstituted or C6 ⁇ 10 aryl group substituted by G 2, (unsubstituted or C1 ⁇ 6 alkoxyimino substituted with G 1) -C1 ⁇ 6 alkyl group, a cyano group or a halogeno, Indicates a group.
  • R 1 and R 2 may together form a 5- to 6-membered ring with the carbon atom to which each of R 1 and R 2 is bonded.
  • 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 6-membered heterocyclyl group, unsubstituted or G 2 -substituted 3 to 6-membered heterocyclyl group C 1 to 6 alkyl group, formyl group, unsubstituted or G 1 -substituted C 1-6 al
  • G a are independently a hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C2 ⁇ 6 alkenyl group substituted with G 1, no showing a substituted by a substituted or G 1 a C2 ⁇ 6 alkynyl, 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, unsubstituted or G C2 ⁇ 6 alkynyl group substituted by one, unsubstituted or C3 ⁇ 8 cycloalkyl group substituted with G 1, unsubstituted or C6 ⁇ 10 aryl group substituted by G 2 or unsubstituted or G, 3 to 6-membered heterocyclyl group substituted by 2 .
  • T represents an oxygen atom, an oxycarbonyl group, a carbonyloxy group, an oxycarbonyloxy group, a sulfur atom, a (thio) carbonyl group, a carbonyl (thio) group, a (thio) carbonyloxy group, an oxycarbonyl ( (Thio) group or a divalent group represented by —O—C ( ⁇ O) —N (G b ) —.
  • * Indicates the bonding position of the group represented by the formula (IV).
  • Q represents either an organic group represented by formula (II) or formula (III).
  • 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 arylthio group, an unsubstituted or C6 ⁇ 10 aryl sulfinyl group substituted by G 2, unsubstituted or C6 ⁇ 10 arylsulfonyl group substituted with G 2, have been 3-10 substituted with unsubstituted or G 2 membered heterocyclyl group, an unsubstituted or 3-10 membered heterocyclyloxy group which is substituted by G 2, unsubstituted or 3-10 membered heterocyclyloxy group which is substituted
  • R a is a hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C3 ⁇ 8 cycloalkyl group substituted with G 1, amino group, C1 ⁇ 6 alkylcarbonylamino group Or an unsubstituted or G 2 -substituted C6-10 aryl 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 C1 ⁇ C6 alkyleneoxy C1 ⁇ 6 alkylene group substituted with G 4, unsubstituted or C3 ⁇ C6 cycloalkylene group substituted by G 4, which is substituted unsubstituted or at G 4 C1 ⁇ C6 alkylene C3 ⁇ 6 cycloalkylene group, an unsubstituted or substituted by G 4 a C1 ⁇ C6 alkyleneoxy C3 ⁇ 6 cycloalkylene group, an unsubstituted or C4 ⁇ C6 cycloalkenylene group substituted with G 4, Or a 3- to 6-membered heterocyclylene group which is unsubstituted
  • a carbon atom of B a or a part of the substituent G 4 on B a may be bonded to a carbon atom on Ar 2 to form a 5- to 6-membered ring.
  • G 1 is a hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group, C1-6 alkoxycarbonyl group, formyloxy group, C1-6 alkylcarbonyloxy group, C1-6 alkoxycarbonyloxy group, cyano A group or a halogeno group.
  • R 1, R 2, R 3, when two or more of R 4 or R a is the radical which is substituted by G 1, G 1 according may be the same or different from each other .
  • G 2 is C1-6 alkyl group, hydroxy 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, C1-6 alkoxy C1-6 haloalkyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, hydroxyl group, C1-6 alkoxy group, C3-8 cycloalkyl C1-6 alkoxy group, C1-6 alkoxyC1 -6 alkoxy group, C1-6 haloalkoxy group, C1-6 haloalkoxy C1-6 haloalkoxy group, formyl group, C1-6 alkylcarbonyl group, C1-6 alkoxycarbonyl group, formyloxy group, C1-6 alkylcarbonyl Oxy group, C1-6 alkoxycarbonyloxy group, C1-6 alkoxycarbonyl Amino group, an unsubstitute
  • G 21 represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, or a halogeno group. If more than one of G 2 or G 4 is a said group substituted with G 21, G 21 according may be the same or different from each other.
  • G 4 is a C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 haloalkyl group, C1-6 alkoxy C1-6 alkyl group, C2-6 alkenyloxy C1-6 alkyl group, hydroxyl group, C1-6 alkoxy group, C1 ⁇ 6 alkoxy C1 ⁇ 6 alkoxy group, substituted with C2 ⁇ 6 alkenyloxy group, C1 ⁇ 6 alkoxycarbonyl group, an unsubstituted or C6 ⁇ 10 aryl group substituted by G 21, unsubstituted or G 21 3-6 membered heterocyclyl group, cyano group, halogeno group, C1-6 alkylene group, C1-6 alkylenedioxy group, oxo group, C3-8 cycloalkyl C1-6 alkyl group, unsubstituted or at G 21 substituted C6 ⁇ 10 aryl C1 ⁇ 6 alkyl group, 3- to 6-membered heterocyclyl C1 ⁇
  • 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.
  • 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 is hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C1 ⁇ 6 alkoxy group substituted with G 1, which is substituted by unsubstituted or G 2 C6 A -10 aryl group, a 3-6 membered heterocyclyl group, a cyano group 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.
  • 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 C6-10 aryl group include a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, and a tetralinyl group.
  • the 3- to 6-membered heterocyclyl group contains 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as ring constituent atoms.
  • 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 6-membered heterocyclyl group include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.
  • Examples of the 3- to 6-membered saturated heterocyclyl group include aziridinyl group, oxiranyl group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, tetrahydropyranyl group, dioxolanyl group, dioxanyl Examples include groups.
  • Examples of 5-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, etc. Can do.
  • Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridanidyl group, and a triazinyl group.
  • 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. In the case two or more of R 1, R 2, R 3 , R 4 or R a is been substituted with G 1, according G 1 may be the same or different from each other .
  • the C1-6 alkoxy group and the halogeno group in the substituent G 1 are as described above.
  • 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 substituent G 2 is a C1-6 alkyl group, a hydroxy C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C3-8 cycloalkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy C1— 6 alkyl group, C1-6 alkoxy C1-6 haloalkyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, hydroxyl group, C1-6 alkoxy group, C3-8 cycloalkyl C1-6 alkoxy group, C1-6 Alkoxy C1-6 alkoxy group, C1-6 haloalkoxy group, C1-6 haloalkoxy C1-6 haloalkoxy group, formyl group, C1-6 alkylcarbonyl group, C1-6 alkoxycarbonyl group, formyloxy group, C1-6 Alkylcarbonyloxy group, C1-6 alkoxycarbonyloxy group, C1-6 al
  • C1-6 alkyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group, C1-6 alkoxycarbonyl group, C1-6 alkylcarbonyloxy group, C1-6 alkoxycarbonyloxy group in the substituent G 2 , C6-10 aryl group, 3-6 membered heterocyclyl group and halogeno group are as described above.
  • Examples of the hydroxy C1-C6 alkyl group include a hydroxymethyl group, a hydroxyethyl group, and a hydroxypropyl group.
  • 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, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3 -Butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 2-methyl-3-pentynyl, 1-hexynyl, 1,1 And -dimethyl-2-butynyl group.
  • 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.
  • the C1-6 alkoxy C1-6 alkyl group is the above-described C1-6 alkoxy group substituted on 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 C3-8 cycloalkyl C1-6 alkoxy group is the above-described C3-6 cycloalkyl group substituted on the C1-6 alkoxy group already described.
  • Examples of the C3-8 cycloalkyl C1-6 alkoxy group include a cyclopropylmethoxy group, a cyclobutylmethoxy group, a cyclopentylmethoxy group, a cyclohexylmethoxy group, and a 2- (cyclopropyl) -ethoxy 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 obtained by substituting the above-mentioned C6-10 aryl group for the C1-6 alkyl group already described. 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 3- to 6-membered heterocyclyloxy group is a hydroxyl group substituted with a 3- to 6-membered heterocyclyl group.
  • Examples of the 3- to 6-membered heterocyclyloxy group include a pyrazolyloxy group and a pyridyloxy group.
  • the 3- to 6-membered heterocyclyloxy group is preferably a 5- to 6-membered heterocyclyloxy 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 C6-10 arylthio group is a group in which a C6-10 aryl group is substituted on the SH group. Examples of the C6-10 arylthio group include a phenylthio group and a naphthylthio group.
  • the C6-10 arylthio group is a sulfanyl group substituted with a C6-10 aryl group.
  • Examples of the C6-10 arylthio group include a phenylthio group and a naphthylthio group.
  • the C6-10 arylsulfinyl group is a sulfinyl group substituted with a C6-10 aryl group.
  • Examples of the C6-10 arylsulfinyl group include a phenylsulfinyl group and a naphthylsulfinyl group.
  • the C6-10 arylsulfonyl group is a sulfonyl group substituted with a C6-10 aryl group.
  • Examples of the C6-10 arylsulfonyl group include a phenylsulfonyl group and a naphthylsulfonyl 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 (dimethylene 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.
  • the C1-6 haloalkyl group, the C2-6 haloalkenyl group, the C2-6 haloalkynyl group, the C1-6 haloalkoxy group, and the C1-6 haloalkylenedioxy group are the C1-6 alkyl groups, C2-6 A halogeno group is substituted on a 6 alkenyl group, a C2-6 alkynyl group, a C1-6 alkoxy group, and a 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- Trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, pentafluoroethoxy group, 2,2,3,4,4,4-hexafluoro-butoxy group, 1-bromo-1,1,2 , 2-tetrafluoroethoxy group and the like.
  • 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.
  • C1-6 alkoxy C1-6 haloalkyl group, C1-6 haloalkoxy C1-6 haloalkoxy group, C1-6 haloalkylthio group, C1-6 haloalkylsulfinyl group, and C1-6 haloalkylsulfonyl group are the same as those described above, C1 A halogeno group is substituted on a -6 alkoxy C1-6 alkyl group, a C1-6 alkoxy C1-6 alkoxy group, a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, and a C1-6 alkylsulfonyl group.
  • Examples of the C1-6 alkoxy C1-6 haloalkyl group include a difluoro (methoxy) methyl group and a 1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl group.
  • Examples of the C1-6 haloalkoxy group include a difluoro (methoxy) methoxy group and a 1,2,2-trifluoro-2- (trifluoromethoxy) ethoxy group.
  • Examples of the C1-6 haloalkylthio group include a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group.
  • 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.
  • Substituent G 21 shows C1 ⁇ 6 alkyl group, C1 ⁇ 6 haloalkyl group, C1 ⁇ 6 alkoxy group, a C1 ⁇ 6 haloalkoxy group or a halogeno group. These are as already described. If more than one of G 2 or G 4 is a said group substituted with G 21, G 21 according may be the same or different from each other.
  • R1 represents a hydrogen atom, an unsubstituted or C1-6 alkyl group substituted with G1 (preferably unsubstituted), an unsubstituted or substituted alkoxy group with G1 (preferably unsubstituted).
  • a C6-10 aryl group (preferably a phenyl group) which is unsubstituted or substituted with G2 (preferably a C1-6 alkoxy group, a C1-6 alkoxycarbonyloxy group), an unsubstituted or a G2 substituted 6 member
  • G2 preferably a C1-6 alkoxy group, a C1-6 alkoxycarbonyloxy group
  • G2 substituted 6 member A ring heteroaryl group (preferably an unsubstituted pyridyl group), a cyano group or a halogeno group is preferred, and an unsubstituted C1-6 alkyl group or a halogeno group is more preferred.
  • R 2 and R 3 are each independently a hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C3 ⁇ 8 cycloalkyl group substituted by G 1, the unsubstituted or C1 ⁇ 6 alkoxy group substituted by G 1, a formyl group, a formyloxy group, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, C1 is substituted by unsubstituted or G 1 ⁇ 6 alkylcarbonyloxy group, an unsubstituted or C6 ⁇ 10 aryl group substituted by G 2, (unsubstituted or C1 ⁇ 6 alkoxyimino substituted with G 1) -C1 ⁇ 6 alkyl group, a cyano group or a halogeno, Indicates a group.
  • R 2 and R 3 a C1-6 alkyl group, a C3-8 cycloalkyl group, a C1-6 alkoxy group, a C1-6 alkylcarbonyl group, a C1-6 alkylcarbonyloxy group, a C6-10 aryl group, a halogeno group, And the substituents G 1 and G 2 are as described above.
  • Examples of the (C1-6 alkoxyimino) -C1-6 alkyl group include a methoxyimino-methyl group and a 1- (ethoxyimino) -ethyl group.
  • R 1 and R 2 may together form a 5-6 membered ring with the carbon atom to which each of R 1 and R 2 is attached.
  • Examples of such a 5- to 6-membered ring include a cyclopentene ring and a cyclohexene ring.
  • R 2 is a hydrogen atom, unsubstituted or G 1 (preferably a hydroxyl group, a halogeno group, a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group.
  • C1-6 alkyl group unsubstituted or substituted with G 1 -substituted C1-6 alkoxy group (preferably unsubstituted), unsubstituted or substituted with G 2 (preferably C1-6 alkoxy group) been C6 ⁇ 10 aryl group (preferably phenyl group), an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1 (preferably unsubstituted), (C1 substituted with unsubstituted or G 1 ⁇ 6alkoxyimino) -C1-6 alkyl groups (preferably unsubstituted), halogeno groups, cyano groups, and formyl groups are preferred, and unsubstituted C1-6 alkyl groups are more preferred.
  • R 3 is unsubstituted or substituted with G 1 (preferably a hydroxyl group, a halogeno group, a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group).
  • G 1 preferably a hydroxyl group, a halogeno group, a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group.
  • C1 ⁇ 6 alkyl group unsubstituted or C1 ⁇ 6 alkoxy group substituted with G 1 (preferably unsubstituted), unsubstituted C3 ⁇ 8 cycloalkyl group (preferably 3-4 cycloalkyl group), An unsubstituted or G 1 -substituted C1-6 alkylcarbonyloxy group (preferably unsubstituted), an unsubstituted or G 2 -substituted C6-10 aryl group (preferably an unsubstituted phenyl group), ( An unsubstituted or G 1 substituted C1-6 alkoxyimino) -C1-6 alkyl group (preferably unsubstituted), a halogeno group, a cyano group or a formyl group; Preferably, a C1-6 alkyl group or a halogeno group which is unsubstituted or substituted with G1 (preferably a hydroxyl group, a halogeno
  • 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 is 3- to 6-membered heterocyclyl group, an unsubstituted or 3-6 membered heterocyclyl C1 ⁇ 6 alkyl group substituted with G 2, a formyl group, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C3 ⁇ 8 cycloalkyl group which is substituted by G 1, unsubstituted or C
  • R 4 C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl C1-6 alkyl group, 3-6 membered heterocyclyl group, C1-6 alkyl
  • the carbonyl group, C1-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, substituent G 1 and substituent G 2 are as described above.
  • the 3- to 6-membered heterocyclyl C1-6 alkyl group is obtained by substituting a 3- to 6-membered heterocyclyl group for a C1-6 alkyl group.
  • the 3- to 6-membered heterocyclyl C1-6 alkyl group is preferably a 5- to 6-membered saturated heterocyclyl C1-6 alkyl such as a tetrahydrofuranylmethyl group, a tetrahydropyranylmethyl group, a dioxolanylmethyl group, a dioxanylmethyl group or the like.
  • Groups; 5- to 6-membered heteroaryl C1-6 alkyl groups such as a pyrazolylmethyl group and a pyridylmethyl group.
  • the C3-8 cycloalkylcarbonyl group is a group in which the aforementioned C3-8 cycloalkyl group is bonded to a carbonyl group.
  • Examples of the C3-8 cycloalkylcarbonyl group include a cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group, and a cyclohexylcarbonyl 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 alkenylcarbonyl group include an acryloyl group and a methacryloyl 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.
  • 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, an oxycarbonyl group, a carbonyloxy group, an oxycarbonyloxy group, a sulfur atom, a (thio) carbonyl group, a carbonyl (thio) group, a (thio) carbonyloxy group, an oxycarbonyl (thio) group, or a formula : —O—C ( ⁇ O) —
  • Examples of the group represented by the formula (IV) include the following.
  • R 4 is a C 1-6 substituted with a hydrogen atom, unsubstituted or G 1 (preferably a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group, a halogeno group).
  • An alkyl group a C2-6 alkenyl group which is unsubstituted or substituted with G 1 (preferably unsubstituted), a C6-10 aryl which is unsubstituted or substituted with G 2 (preferably a C1-6 alkoxy group) 6 alkyl group (preferably benzyl group), unsubstituted or C 1-6 alkylcarbonyl group substituted with G 1 (preferably C 1-6 alkoxy group, C 1-6 alkylcarbonyloxy group), unsubstituted or G 1
  • R a is a hydrogen atom, an unsubstituted or C1 ⁇ 6 alkyl group substituted with G 1, unsubstituted or C3 ⁇ 8 cycloalkyl group substituted with G 1, amino group, C1 ⁇ 6 alkylcarbonylamino group Or an unsubstituted or G 2 -substituted C6-10 aryl group.
  • the C1-6 alkyl group, C3-8 cycloalkyl group, C6-10 aryl group, substituent G 1 and substituent G 2 in R a are as described above.
  • the C1-6 alkylcarbonylamino group is a group in which the above-described C1-6 alkylcarbonyl group is substituted on the amino group.
  • Examples of the C1-6 alkylcarbonylamino group include an acetylamino group and a propionylamino group.
  • R a a hydrogen atom, an unsubstituted alkyl group, an unsubstituted C3-8 cycloalkyl group (preferably a C3-4 cycloalkyl group), an amino group, a C1-6 alkylcarbonylamino group,
  • a C6-10 aryl group preferably a phenyl group which is unsubstituted or substituted with G 2 (preferably a C1-6 haloalkyl group) is preferred, and an unsubstituted alkyl group or a hydrogen atom is more preferred.
  • 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 in Ar 1 and the substituent G 2 are as described above.
  • 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.
  • the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring.
  • 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, 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.
  • 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 an unsubstituted or G 2 to C 6-10 aryl group (preferably a phenyl group or a naphthyl group) or an unsubstituted or G 2 to 5 membered heteroaryl. preferably group (preferably pyridyl group), more preferably a pyridyl group substituted with a phenyl group or an unsubstituted or G 2 substituted with unsubstituted or G 2.
  • G 2 in Ar 1 is a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 haloalkyl group, a C1-6 haloalkoxy group, a C1-6 alkoxycarbonyl group, substituted or G 21 (preferably C1 ⁇ 6 haloalkyl group) C6 ⁇ 10 aryl group substituted with (preferably phenyl group), substituted with unsubstituted or G 21 (preferably C1 ⁇ 6 haloalkyl group) C6 -10 aryl C1-6 alkyl group (preferably benzyl group), C6-10 aryloxy group (preferably phenoxy group) which is unsubstituted or substituted with G 21 (preferably C1-6 haloalkyl group), C1-6 Haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, pentaf O
  • 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 arylthio group, an unsubstituted or C6 ⁇ 10 aryl sulfinyl group substituted by G 2, unsubstituted or C6 ⁇ 10 arylsulfonyl group substituted by G 2, have been 3-10 substituted with unsubstituted or G 2 It shows a membered heterocyclyl group, an unsubstituted or 3-10 membered heterocyclyloxy group unsubstituted or 3-6 membered heterocyclylthio group or a ferrocenyl group substituted with G 2 which is substituted by G 2.
  • the C6-10 aryl group in Ar 2 is as described above, and is preferably phenyl.
  • the C6-10 aryloxy group is as described above, and is preferably phenoxy.
  • the 3- to 10-membered heterocyclyl group is as described above, preferably a 5- to 10-membered ring heteroaryl group, more preferably a thiazolyl group, a triazolyl group, a pyrazolyl group, a pyridyl group, a pyridazinyl group, a quinolyl group. It is.
  • the 3- to 10-membered heterocyclyloxy group is a hydroxyl group substituted with a 3- to 10-membered heterocyclyl 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 5- to 6-membered heteroaryloxy group is more preferably a pyrazolyloxy group, a pyridyloxy group, a pyridazinyloxy group, or a pyrimidinyloxy group.
  • the 3- to 10-membered heterocyclylthio group is a group in which a 3- to 10-membered heterocyclyl group is substituted on the SH group.
  • Examples of the 3- to 10-membered heterocyclylthio group include 5- to 6-membered heteroarylthio groups such as a pyrazolylthio group and a pyridylthio group, and a pyridylthio group is preferable.
  • the C6-10 arylthio group is as described above, and is preferably a phenylthio group.
  • the arylsulfinyl group is as described above, and is preferably phenylsulfinyl.
  • the arylsulfonyl group is as described above, and is preferably phenylsulfonyl.
  • Substituent G 2 is as described above, preferably C 1-6 alkyl group, C 1-6 haloalkyl group, C 1-6 alkoxy group, C 3-8 cycloalkyl C 1-6 alkoxy group (preferably C 3-6 4 cycloalkylalkoxy group), C1-6 haloalkoxy group, C6-10 aryl group which is unsubstituted or substituted with G 21 (preferably a phenyl group), C6-10 aryl which is unsubstituted or substituted with G 21
  • An oxy group preferably a phenoxy group
  • an unsubstituted or G 21 -substituted 5- to 6-membered heterocyclyl group preferably a pyridyl group
  • an unsubstituted or G 21 -substituted 5- to 6-membered heterocyclyloxy group Preferably a pyridyloxy group
  • a pentafluorosulfanyl group a cyano
  • G 2 more preferably, C1 ⁇ 6 haloalkyl group, C1 ⁇ 6 alkoxy group, C1 ⁇ 6 haloalkoxy group, an unsubstituted or substituted phenyl group G 21, which is substituted by unsubstituted or G 21 A phenoxy group, an unsubstituted or G 21 -substituted pyridyl group, an unsubstituted or G 21 -substituted pyridyloxy group, a halogeno group, or a C1-2 haloalkylenedioxy group.
  • the substituent G 21 is as described above, and is preferably a halogeno group, a C1-6 haloalkyl group or a C1-6 haloalkoxy group.
  • Ar 2 is preferably an unsubstituted or G 2 -substituted C 6-10 aryl group (preferably a phenyl group), an unsubstituted or G 2 -substituted C 6-10 aryloxy group (preferably a phenoxy group), an unsubstituted or 3-10 membered heterocyclyl group (preferably a thiazolyl group which is substituted by G 2, triazolyl group, a pyrazolyl group, a pyridyl group, pyridazinyl group, quinolyl group), unsubstituted or G 2
  • a 3- to 10-membered heterocyclyloxy group (preferably pyridyloxy group, pyrazinyloxy group, pyrimidinyloxy group) substituted with G 2 is more preferably a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a halogeno 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 C1 ⁇ C6 alkyleneoxy C1 ⁇ 6 alkylene group substituted with G 4, unsubstituted or C3 ⁇ C6 cycloalkylene group substituted by G 4, which is substituted unsubstituted or at G 4 C1 ⁇ C6 alkylene C3 ⁇ 6 cycloalkylene group, an unsubstituted or substituted by G 4 a C1 ⁇ C6 alkyleneoxy C3 ⁇ 6 cycloalkylene group, an unsubstituted or C4 ⁇ C6 cycloalkenylene group substituted with G 4, Or a 3- to 6-membered heterocyclylene group which is un
  • C1 ⁇ C6 alkylene radicals are those as already mentioned.
  • 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.
  • the C1 to C6 alkyleneoxy C1 to 6 alkylene group is a group formed by bonding two C1 to 6 alkylene groups via an oxygen atom.
  • Examples of the C1-C6 alkyleneoxy C1-6 alkylene group include a methyleneoxymethylene group, a methyleneoxyethylene group, and an ethyleneoxymethylene group.
  • 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-cyclopentylene 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.
  • the C1-C6 alkylene C3-6 cycloalkylene group is a group formed by bonding a C1-6 alkylene group and a C3-6 cycloalkylene group.
  • the C1 to C6 alkylene C3 to 6 cycloalkylene group is preferably a C1 to 2 alkylene C3 to 6 cycloalkylene group such as methylenecyclopropylene, methyleneoxycyclohexylene, and ethyleneoxycyclohexylene.
  • the C1-C6 alkyleneoxy C3-6 cycloalkylene group is a group formed by bonding a C1-6 alkylene group and a C3-6 cycloalkylene group via an oxygen atom.
  • the C1-C6 alkyleneoxy C3-6 cycloalkylene group is preferably a C1-2 alkyleneoxy C3-6 cycloalkylene group such as methyleneoxycyclopropylene, methyleneoxycyclohexylene, ethyleneoxycyclohexylene.
  • 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) And the like, preferably a cyclopentenylene group or a cyclohexenylene group.
  • 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 dihydrofurylene group, tetrahydrofurylene group, pyrrolinylene group, pyrrolidinylene group, pyrazolinylene group, pyrazolidinylene group, imidazolinylene group, imidazolidinylene group, oxazolinylene group, oxazolidinylene group, Examples include 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 piperidinylene group is particularly preferable.
  • the 3-6 membered heterocyclylene group may be a C1-6 alkylene group, which may be cross-linked.
  • 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 substituents It has been C2 ⁇ C6 alkynylene group, or an unsubstituted or C3 ⁇ C6 cycloalkylene group substituted with G 4 or unsubstituted or 3-6 membered heterocyclylene group substituted by G 4,, more preferably , an unsubstituted or C1 ⁇ C6 alkylene group substituted with G 4, unsubstituted or C3 ⁇ C6 cycloalkylene group substituted with G 4.
  • G 4 is a C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 haloalkyl group, C1-6 alkoxy C1-6 alkyl group, C2-6 alkenyloxy C1-6 alkyl group, hydroxyl group, C1-6 alkoxy group, C1 ⁇ 6 alkoxy C1 ⁇ 6 alkoxy group, substituted with C2 ⁇ 6 alkenyloxy group, C1 ⁇ 6 alkoxycarbonyl group, an unsubstituted or C6 ⁇ 10 aryl group substituted by G 21, unsubstituted or G 21 3-6 membered heterocyclyl group, cyano group, halogeno group, C1-6 alkylene group, C1-6 alkylenedioxy group, oxo group, C3-8 cycloalkyl C1-6 alkyl group, unsubstituted or at G 21 substituted C6 ⁇ 10 aryl C1 ⁇ 6 alkyl group, 3- to 6-membered heterocyclyl C1 ⁇
  • a C1-6 alkyl group, a C3-8 cycloalkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy C1-6 alkyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 alkoxy group, C1 6-6 alkoxycarbonyl group, C1-6 alkylenedioxy group, C6-10 aryl group, C6-10 aryl C1-6 alkyl group, 3-6 membered heterocyclyl group, 3-6 membered heterocyclyl C1-6 alkyl group, halogeno group , C1-6 alkylene group, substituent G 2 and substituent G 21 are as described above.
  • 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 alkenyloxy C1-6 alkyl group is a C1-6 alkyl group substituted with a C2-6 alkenyloxy group.
  • Examples of the C2-6 alkenyloxy C1-6 alkyl group include a vinyloxymethyl group and an allyloxymethyl group.
  • Examples of the C3-8 cycloalkyl C1-6 alkyl group include a cyclopropylmethyl group and a cyclopentylmethyl group.
  • Examples of the C3-8 cycloalkyloxy C1-6 alkyl group include a cyclopropyloxymethyl group and a cyclohexyloxymethyl group.
  • Examples of the C6-10 aryloxy C1-6 alkyl group include a phenoxymethyl group and a naphthyloxymethyl group.
  • the 3- to 6-membered heterocyclyloxy C1-6 alkyl group is preferably a 5- to 6-membered heteroarylmethyl group such as a pyrazolyloxymethyl group and a pyridyloxymethyl group.
  • the C1-6 alkylidene group include a methylidene group and a propane-2-ylidene group.
  • G 4 C1-6 alkyl group, C1-6 haloalkyl group, C1-6 alkoxy C1-6 alkyl group, C2-6 alkenyloxy C1-6 alkyl group, hydroxyl group, C1-6 alkoxy group, C1 A 6-6 alkoxycarbonyl group, an unsubstituted or substituted C6-10 aryl group with G 21 (preferably a phenyl group), an unsubstituted or G 21 substituted 3-6 membered heterocyclyl group (preferably a pyridyl group, pyrimidinyl group, dioxolanyl group), a halogeno group, C1 ⁇ 6 alkylene group, C1 ⁇ 6 alkylenedioxy group, an oxo group, an unsubstituted or have been C6 ⁇ 10 aryl C1 ⁇ 6 alkyl group (preferably benzyl substituted by G 21 Group), a 3-6 membered heterocyclyl C1-6 alkyl group which
  • the substituent G 21 in G 4 is preferably a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a halogeno group.
  • Part of a substituent G 4 carbon atoms or B a of B a may form a 5- or 6-membered ring with the carbon atom on Ar 2.
  • the 5- to 6-membered ring include a cyclopentene ring, a cyclohexene ring, a dihydrofuran ring, a dihydrodioxin ring, a dihydropyran ring, and the like, preferably a cyclopentene ring, a cyclohexene ring, a dihydrodioxin ring, and a dihydropyran ring.
  • 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 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.
  • Agricultural and horticultural fungicides of the present invention include a wide variety of filamentous fungi, such as algae (Oomycetes), Ascomycetes, incomplete fungi (Deuteromycetes), basidiomycetes, mating It can be used for controlling plant diseases derived from fungi belonging to fungi (Zygomycetes).
  • filamentous fungi such as algae (Oomycetes), Ascomycetes, incomplete fungi (Deuteromycetes), basidiomycetes, mating It can be used for controlling plant diseases derived from fungi belonging to fungi (Zygomycetes).
  • Rust disease Puccinia arachidis
  • withering disease Pythium debaryanum
  • rust spot disease Alternaria alternata
  • white silk disease Sclerotium rolfsii
  • cucumber: powdery mildew Sphaerotheca fuliginea
  • Downy mildew Pseudoperonospora cubensis
  • vine blight Mycosphaerella melonis
  • vine split disease Fusarium oxysporum
  • mycorrhizal disease Sclerotinia sclerotiorum
  • gray mold disease Botrytis cinerea
  • anthracnose disease Coldletotrichum orbiculare
  • black star disease Cladosporium cucumerinum
  • brown spot disease Corynespora cassicola
  • seedling blight Pythium debaryanam, Rhizoctonia solani Kuhn
  • Tomato Gray mold disease (Botrytis cinerea), leaf mold disease (Cladosporium fulvum), plague (Phytophthora infestans), half body wilt disease (Verticillium albo-atrum), powdery mildew (Oidium neolycopersici), ring crest Diseases (Alternaria solani), Subtilis (Pseudocercospora fuligena), etc.
  • cabbage root-knot disease (Plasmodiophora brassicae), soft rot disease (Erwinia carotovora), black rot disease (Xanthomonas campesrtis pv. campestris), black spot bacterial disease (Pseudomonas syringae pv. maculicalas, Pseudomonas syringae pv. alisalensis), downy mildew (Peronospora parasitica), mycorrhizal disease (Sclerotinia sclerotiorum), black soot disease (Alternaria brassicicola), gray mold disease (Botrytis cinerea), etc.
  • Kidney Sclerotinia sclerotiorum, gray mold Diseases (Botrytis cinerea), anthrax (Colletotrichum lindemuthianum), keratosis (Phaeoisariopsis griseola), 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), gray mold disease (Botrytis cinerea), etc.
  • Ume black rot (Cladosporium carpophilum), gray mold disease (Botrytis cinerea), gray star disease (Monilinia mumecola), etc.
  • Oysters powdery mildew (Phyllactinia kakicola), anthrax Diseases such as Gloeosporium kaki, Cercospora kaki, peaches: Monilinia fructicola, black scab (Cladosporium carpophilum), homopsis spoilage (Phomopsis sp.), Perforated bacteria (Xanthomonas campestris pv.
  • Pruni and other almonds Monilinia laxa, spot disease (Stigmina carpophila), black spot disease (Cladosporium carpophilum), leaf blight disease (Polystigma rubrum), spotted leaf disease (Alternaria alternata), anthrax Sugar beetle (Colletotrichum gloeospoides), etc.
  • Sweet potato Monilinia fructicola, anthracnose (Colletotrichum acutatum), black spot (Alternaria sp.), Larvae nuclear disease (Monilinia kusanoi), etc.
  • Grapes Gray mold disease (Botrytis) cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black mildew (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot ( Guignardia bidwellii), white rot (Coniella castaneicola), etc.
  • Pear Venturia nashicola, Red Star Disease (Gymnosporangium asiaticum), Black Spot Disease (Alternaria kikuchiana), Ring Ring Disease (Botryosphaeria berengeriana) Powdery mildew (Phyllactinia mali), blight (Phomopsis fukushii), brown spot disease (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc.
  • Rice Rice blast (Pyricularia oryzae), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), sesame leaf blight (Cochliobolus miyabeanus), seedling blight (Pythium graminicolum , White leaf blight (Xanthomonas oryzae), seedling blight (Burkholderia plantarii), brown streak (Acidovorax avenae), blight blight (Burkholderia glumae), streak blight (Cercospora oryzae), rice leaf blight (Ustilaginoidea) virens), brown rice (Alternaria alternata, Curvularia intermedia), belly black rice (Alternaria padwickii), red rice (Epicoccam purpurascenns), etc.
  • Tobacco Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), plague ), Etc.
  • Tulip Gray mold disease (Botrytis cinerea)
  • Sunflower Downy mildew (Plasmopara halstedii), Mycorrhizal disease (Sclerotinia sclerotiorum), etc.
  • Bentgrass Snow rot (Sclerotinia borealis), Large patch (Rhizoctonia solani) , Dollar spot (Sclerotinia homoeocarpa), blast (Pyricularia sp.), Red blight (Pythium aphanidermatum), anthracnose (Colletotrichum graminicola) Orchardgrass: powdery mildew (Erysiphe graminis), etc.
  • Soybean Purpura (Cercospora kikuchii), downy mildew (Peronospora manshurica), stem blight (Phytophthora sojae), rust (Phakopsora pachyrhizi), sclerotia (Sclerotinia sclerotiorum) Anthracnose (Colletotrichum truncatum), gray mold (Botrytis cinerea), etc.
  • Potato Phytophthora infestans, summer plague (Aleternaria solani), black rot (Thanatephorus cucumeris), etc.
  • Banana Panama disease (Fusarium oxysporum), Shiga (Mycosphaerella fijiensis, Mycosphaerella musicola), etc.
  • Rapeseed Sclerotinia sclerotiorum, root rot (Phoma lingam), black spot (Alternaria brassicae), etc.
  • Coffee Rust (Hemileia vastatrix), Anthrax (Colletotrichum coffeanum) Brown eye disease (Cercospora coffeicola), 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 diamondback moth, planthopper, leafhopper and aphids.
  • 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. Can be 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.
  • the agricultural and horticultural fungicide, pest control agent, and insecticidal or acaricidal fungicide for agricultural and horticultural use according to the present invention are other agricultural and horticultural effects having effects such as sterilization, insecticidal / miticidal, nematicidal, and soil-killing pests.
  • Drugs for use; Plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. may be mixed or used together. An example is shown below.
  • Nucleic acid biosynthesis inhibitors (A) RNA polymerase I inhibitor: benalaxyl, benalaxyl-M, furaxyl, metalaxyl, metalaxyl-M; oxadixil; cloziracone, off-race; (B) adenosine deaminase inhibitor: bupilimate, dimethylylmol, ethylimol; (C) DNA / RNA synthesis inhibitors: Himexazole, octirinone; (D) DNA topoisomerase II inhibitor: oxophosphate;
  • Mitotic fission inhibitor and cell division inhibitor (A) ⁇ -tubulin polymerization inhibitor: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; dietofencarb; zoxamide; ethaboxam; (B) Cell division inhibitor: Penciclone; (C) Delocalization inhibitor of spectrin-like protein: fluopicolide;
  • Respiratory inhibitor (A) Complex I NADH oxidoreductase inhibitor: diflumetrim; tolfenpyrad; (B) Complex II succinate dehydrogenase inhibitors: benodanyl, flutolanil, mepronil; isofetamide; fluopyram; fenfram, flumecyclox; carboxin, oxycarboxyl; tifluzamide; , Furametopyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid; (C) Complex III ubiquinol oxidase Qo inhibitor: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyroxystrobin; Piramethostrobin, triclopyricarb; Cresoxime-methyl, trifloxystrobin; Dimoxystrobin, Phenaminestrobin, Metominostrobin
  • Signaling inhibitor (A) Signaling inhibitor: quinoxyphene, proquinazide; (B) MAP / histidine kinase inhibitor in osmotic signal transduction: fenpiclonil, fludioxonil; clozolimate, iprodione, procymidone, vinclozolin;
  • Lipid and cell membrane synthesis inhibitors (A) Phospholipid biosynthesis, methyltransferase-inhibitors: edifenphos, iprobenphos, pyrazophos; isoprothiolane; (B) lipid peroxidants: biphenyl, chloroneb, dichlorane, kinden, technazene, tolcrofosmethyl; etridiazole; (C) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarbfocetylate, prothiocarb; (D) Microorganisms that disturb the cell membrane of pathogenic bacteria: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain; (E) Agents that disrupt the cell membrane: an extract of Goseika Yupte (Tea) P
  • 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
  • Trehalase inhibitor Validamycin
  • B chitin synthase inhibitor: polyoxin, polyoxolim
  • C Cellulose synthase inhibitor: dimethomorph, furmorph, pyrimorph
  • Bench Avaricarb Iprovaricarb, Toluprocarb, Variphenate
  • Mandipropamide
  • Melanin biosynthesis inhibitor (a) Reductase inhibitor of melanin biosynthesis: Fusaride; Pyroxylone; Tricyclazole; (B) Dehydrase inhibitor of melanin biosynthesis: carpropamide; diclocimet; phenoxanyl;
  • 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) , Mankappa, methylam, polycarbamate, propineb, thiram, dineb, ziram; captan, captahol, phorpet; chlorothalonil; dichlorfluanide, tolylfluanid; guazatine, iminotadine acetate, iminoctadine albecate albesylate; anilazine; dithianone Quinomethionate; fluorimide;
  • Acetylcholinesterase inhibitor (A) Carbamate series: Alanicarb, Aldicarb, Bengiocarb, Benfuracarb, Butcarboxyme, Butoxycarboxyme, Carbaryl, Carbofuran, Carbosulfan, Ethiophenecarb, Fenobucarb, Formethanate, Furatiocarb, Isoprocarb, Methiocarb, Mesomil, Oxamyl, Pirimicarb, Propoxycarb Thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb; phenothiocarb, MIPC, MPMC, MTMC, aldoxicarb, alixicarb, aminocarb, bufencarb, cloetocarb, metam sodium, promecarb;
  • 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, bioareslin, 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
  • Nicotinic acetylcholine receptor agonists acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxafurol, nicotine; (5) Nicotinic acetylcholine receptor allosteric modulators: spinetoram, spinosad; (6) Chloride channel activator: abamectin, emamectin benzoate, repimectin, milbemectin; ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime; (7) Juvenile hormone-like substances: hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; geofenolan, ep
  • Mite growth inhibitor clofentezin, diflovidazine, hexythiazox, etoxazole;
  • Microbial-derived insect midgut mesentery Bacillus thuringiensis subsp. Isla elensis, Bacillus sphaericus, Bacillus thuringiensis subsp. Aisawai, Bacillus thuringiensis subsp.
  • Crop proteins Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; (12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, phenbutasine oxide, propargite, tetradiphone; (13) Oxidative phosphorylation uncoupler: chlorfenapyr, sulframide, DNOC; binapacryl, dinobutone, dinocup; (14) Nicotinic acetylcholine receptor channel blockers: bensultap, cartap hydrochloride; nereistoxin; thiosultap monosodium salt, thiocyclam; (15) Chitin synthesis inhibitor: bistrifluron, chlorfluazuron, diflu
  • 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.
  • dosage forms such as wettable powder, emulsion, aqueous solvent, granular wettable powder, powder, tablet and the like can be mentioned.
  • 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 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 physical properties of the target compound were as follows.
  • Ph is a phenyl group
  • Me is a methyl group
  • Et is an ethyl group
  • n Pr is an n-propyl group
  • i Pr is an isopropyl group
  • c Pr is a cyclopropyl group
  • n Bu is n.
  • a t Bu group is t- butyl group
  • Py is a pyridyl group
  • Ac is an acetyl group
  • Bn is PMB benzyl denotes a para-methoxybenzyl group.
  • Table 1 shows compounds represented by formula (I) in which Q is an organic group represented by formula (I) (compound represented by formula (I-1) shown below). Disclose.
  • Tables 2 to 6 are compounds represented by formula (I), wherein Q is an organic group represented by formula (II) (formula (I-2) shown below) Compound).
  • the compounds described in Tables 2 to 6 are compounds in which R 1 , R 2 and R 3 are methyl groups.
  • the carbon atom marked with * in the structural formula in “B a ” represents a carbon atom bonded to oxygen of the oxime (the same meaning is shown in the following tables).
  • the carbon atom or nitrogen atom marked with ** in the structural formula of “B a ” represents a carbon atom or nitrogen atom bonded to “Ar 2 ” (the same meaning is shown in the following tables).
  • Compound c-187 in Table 3 is N-oxide.
  • Tables 7 to 8 show substituents in the compound represented by the formula (I-3).
  • Table 9 shows the substituents in the compound represented by the formula (I-4).
  • Table 11 shows 1 H-NMR data for some of the compounds described in Tables 1 to 10 above.
  • Test Example 1 Wheat powdery mildew control test-1 An emulsion containing 5% active ingredient was prepared by dissolving 5 parts by mass of the compound of the present invention in 95 parts by mass of a dimethylformamide solution containing 1.5% of polyoxyethylene sorbitan monolaurate. The emulsion was diluted with an aqueous solution containing 0.02% polyoxyethylene sorbitan monolaurate to obtain a chemical solution having a compound concentration of 100 ppm. Subsequently, the chemical solution was sprayed on wheat seedlings (variety “Chihoku”, 1.0-1.2 leaf stage) cultivated in an unglazed pot. Leaves were air dried.
  • Test Example 2 Wheat red rust control test-1 An emulsion was prepared in the same manner as in Test Example 1. The emulsion was diluted with an aqueous solution containing 0.02% polyoxyethylene sorbitan monolaurate to obtain a chemical solution having a compound concentration of 100 ppm. The chemical solution was sprayed on wheat seedlings grown in an unglazed pot (variety “Noribayashi No. 61”, 1.0-1.2 leaf stage). Leaves were air dried. Thereafter, 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 leaf was compared with no treatment, and the control value was calculated.
  • Test Example 4 Wheat red rust control test-2 An emulsion was prepared in the same manner as in Test Example 3. The emulsion was diluted with water to an active ingredient of 125 ppm to obtain a chemical solution. The above chemical solution was sprayed on wheat seedlings grown in an unglazed pot (variety “Noribayashi No. 61”, 1.0 to 1.2 leaves). After air-drying the leaves, summer spores of wheat red rust fungus (Puccinia recondita) were shaken off and inoculated and kept in a greenhouse at 20-25 ° C. for 10 days. In the same manner as in Test Example 1, the lesion appearance state on the leaf was compared with no treatment, and the control value was calculated.
  • the wheat red rust control test shown in Table 15 was conducted. All the compounds showed a control value of 75% or more.
  • test examples show that the compound of the present invention is useful as an active ingredient of an insecticide or acaricide.
  • Test Example 6 Efficacy Confirmation Test for Cotton Aphid An emulsion prepared by the same method as Test Example 5 was diluted with water to obtain a chemical solution having a compound concentration of 125 ppm. Cotton aphid adults were inoculated on the first true leaf of cucumber 10 days after germination sowed in a 3 inch pot. One day later, the adult worms were removed, and the drug solution was sprayed on the cucumbers where the larvae that were delivered were infested. It was placed in a constant temperature and humidity room at a temperature of 25 ° C. and a humidity of 65%, and after 5 days, the life of the aphids was examined and the insecticidal rate was calculated. The test was performed in duplicate.
  • Test Example 7 Efficacy Confirmation Test for Spider Mite An emulsion prepared by the same method as Test Example 5 was diluted with water to obtain a chemical solution having a compound concentration of 125 ppm. On the first true leaf of green beans that had been sown for 10 days after being sown in 3 inch pots, 10 adult females of the spider mite were inoculated. One day later, the chemical solution was sprayed. It was placed in a constant temperature and humidity room with a temperature of 25 ° C. and a humidity of 65%, and after 3 days, the life and death of the spider mite were examined, and the insecticidal rate was calculated. The test was performed in duplicate.
  • Test Example 8 Efficacy confirmation test against bean aphids An emulsion prepared by the same method as Test Example 5 was diluted with water to obtain a chemical solution having a compound concentration of 125 ppm. Cowpeas were bred in 3-inch pots and seed aphid nymphs were inoculated on the primary leaves. The said chemical
  • Test Example 9 Efficacy Confirmation Test for Kanzawa Spider Mite An emulsion prepared by the same method as Test Example 5 was diluted with water to obtain a chemical solution having a compound concentration of 125 ppm. Kidney seedlings were bred in 3-inch pots, and 10 adult female Kanzawa spider mites were inoculated on the primary leaves. The said chemical
  • 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. Therefore, the pyridine compound of the present invention is industrially useful.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

La présente invention concerne: un composé représenté par la formule (I) (dans la formule , R1, R2, R3, et R4 représentent chacun indépendamment un atome d'hydrogène, un groupe alkyle en C1 -6, ou analogue. R1 et R2 peuvent se lier pour former ensemble un cycle de 5 à 6 chaînons avec la liaison d'atomes de carbone R1 et R2. Q représente un groupe organique représenté par la formule (II) (dans la formule, Ar1 représente un groupe aryle en C6 -10 ou analogue. Ra représente un atome d'hydrogène, un groupe alkyle en C1 -6, ou analogue. * indique la position de liaison du groupe organique représenté par la formule (II) .)) ou analogue, ou un sel de celui-ci; et un fongicide, un pesticide, un insecticide ou un acaricide agricole et horticole contenant, en tant que principe actif, au moins un élément choisi dans le groupe constitué de ce composé et des sels de celui-ci.
PCT/JP2015/068009 2014-06-24 2015-06-23 Compose pyridine et son utilisation WO2015199065A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2016529594A JP6508540B2 (ja) 2014-06-24 2015-06-23 ピリジン化合物およびその用途

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014129726 2014-06-24
JP2014-129726 2014-06-24

Publications (1)

Publication Number Publication Date
WO2015199065A1 true WO2015199065A1 (fr) 2015-12-30

Family

ID=54938147

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2015/068009 WO2015199065A1 (fr) 2014-06-24 2015-06-23 Compose pyridine et son utilisation

Country Status (3)

Country Link
JP (1) JP6508540B2 (fr)
TW (1) TW201605800A (fr)
WO (1) WO2015199065A1 (fr)

Cited By (6)

* 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
WO2019107393A1 (fr) * 2017-11-30 2019-06-06 日本曹達株式会社 Composé de thiéno[2,3-d]pyrimidine-2,4(1h,3h)dione tétrasubstitué en position 1, 3, 5 et 6, et fongicide agricole et horticole
CN110642748A (zh) * 2019-09-20 2020-01-03 华南理工大学 一种o-(2-三氟甲基-2-羟基乙基)肟醚衍生物及其合成方法与应用
CN112867711A (zh) * 2018-10-17 2021-05-28 杜克大学 醌还原酶2抑制剂化合物及其用途
WO2024127829A1 (fr) * 2022-12-12 2024-06-20 日本曹達株式会社 Composé de chlorure de phénoxycarbamoyle et son procédé de production

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07506097A (ja) * 1992-04-22 1995-07-06 ヘキスト・シェーリング・アグレボ・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 殺ダニ性，殺虫性および殺線虫性の置換された（ヘテロ）アリールアルキルケトンオキシムｏ−エーテル，それらの製造方法，それらを含む薬剤，およびそれらの有害生物防除剤としての使用
JPH093047A (ja) * 1995-06-21 1997-01-07 Nippon Soda Co Ltd ケトンオキシムエーテル誘導体、その製造方法及び農園芸用殺菌剤
WO2001034568A1 (fr) * 1999-11-05 2001-05-17 Nippon Soda Co., Ltd. Composes oxime o-ether et fongicides utiles dans l'agriculture et l'horticulture
WO2002064566A1 (fr) * 2001-02-14 2002-08-22 Nippon Soda Co.,Ltd. Composes d'oxime o-ether et fongicides a usage agricole et horticole
WO2003006432A1 (fr) * 2001-07-09 2003-01-23 Nippon Soda Co.,Ltd. Compose d'ether d'oximes et bactericide agricole ou horticole
WO2003087056A1 (fr) * 2002-04-15 2003-10-23 Nippon Soda Co.,Ltd. Nouveau compose oxime o-ether, procede de production, et bactericide agricole ou horticole
CN1844111A (zh) * 2006-03-22 2006-10-11 南开大学 噻唑肟醚类衍生物和制备及其应用
JP2010138166A (ja) * 2008-11-17 2010-06-24 Ishihara Sangyo Kaisha Ltd 新規ピリジン誘導体又はその塩、それらを含有する有害生物防除剤並びにそれらの製造方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001138166A (ja) * 1999-11-08 2001-05-22 Nippei Toyama Corp 工具交換装置および工具交換方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07506097A (ja) * 1992-04-22 1995-07-06 ヘキスト・シェーリング・アグレボ・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 殺ダニ性，殺虫性および殺線虫性の置換された（ヘテロ）アリールアルキルケトンオキシムｏ−エーテル，それらの製造方法，それらを含む薬剤，およびそれらの有害生物防除剤としての使用
JPH093047A (ja) * 1995-06-21 1997-01-07 Nippon Soda Co Ltd ケトンオキシムエーテル誘導体、その製造方法及び農園芸用殺菌剤
WO2001034568A1 (fr) * 1999-11-05 2001-05-17 Nippon Soda Co., Ltd. Composes oxime o-ether et fongicides utiles dans l'agriculture et l'horticulture
WO2002064566A1 (fr) * 2001-02-14 2002-08-22 Nippon Soda Co.,Ltd. Composes d'oxime o-ether et fongicides a usage agricole et horticole
WO2003006432A1 (fr) * 2001-07-09 2003-01-23 Nippon Soda Co.,Ltd. Compose d'ether d'oximes et bactericide agricole ou horticole
WO2003087056A1 (fr) * 2002-04-15 2003-10-23 Nippon Soda Co.,Ltd. Nouveau compose oxime o-ether, procede de production, et bactericide agricole ou horticole
CN1844111A (zh) * 2006-03-22 2006-10-11 南开大学 噻唑肟醚类衍生物和制备及其应用
JP2010138166A (ja) * 2008-11-17 2010-06-24 Ishihara Sangyo Kaisha Ltd 新規ピリジン誘導体又はその塩、それらを含有する有害生物防除剤並びにそれらの製造方法

Cited By (6)

* 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
WO2019107393A1 (fr) * 2017-11-30 2019-06-06 日本曹達株式会社 Composé de thiéno[2,3-d]pyrimidine-2,4(1h,3h)dione tétrasubstitué en position 1, 3, 5 et 6, et fongicide agricole et horticole
CN112867711A (zh) * 2018-10-17 2021-05-28 杜克大学 醌还原酶2抑制剂化合物及其用途
CN110642748A (zh) * 2019-09-20 2020-01-03 华南理工大学 一种o-(2-三氟甲基-2-羟基乙基)肟醚衍生物及其合成方法与应用
WO2024127829A1 (fr) * 2022-12-12 2024-06-20 日本曹達株式会社 Composé de chlorure de phénoxycarbamoyle et son procédé de production

Also Published As

Publication number Publication date
JPWO2015199065A1 (ja) 2017-04-20
JP6508540B2 (ja) 2019-05-08
TW201605800A (zh) 2016-02-16

Similar Documents

Publication Publication Date Title
JP7158386B2 (ja) オキサジアゾール化合物および農園芸用殺菌剤
JP6508540B2 (ja) ピリジン化合物およびその用途
JP2021008403A (ja) １，３，５，６−テトラ置換チエノ［２，３−ｄ］ピリミジン−２，４（１Ｈ，３Ｈ）ジオン化合物および農園芸用殺菌剤
JP6837052B2 (ja) ピリジン化合物およびその用途
WO2019065516A1 (fr) Composé quinoléine, et agent bactéricide pour application agricole et horticole
WO2016195077A1 (fr) Composé guanidine et bactéricide
JP2021028298A (ja) １，３，５，６−テトラ置換チエノ［２，３−ｄ］ピリミジン−２，４（１Ｈ，３Ｈ）ジオン化合物および農園芸用殺菌剤
WO2016039048A1 (fr) Composé de pyridine et son utilisation
JP6221189B2 (ja) ピリジン化合物およびその用途
JP5322296B2 (ja) テトラゾイルオキシム誘導体を含む植物病害防除剤の使用方法
JP2016079175A (ja) アミジノピリジン化合物を含有する農園芸用殺菌剤
WO2016047550A1 (fr) Fongicide agricole et horticole contenant un composé d'arylamidine
JP2020097575A (ja) １，３，５，６−テトラ置換チエノ［２，３−ｄ］ピリミジン−２，４（１Ｈ，３Ｈ）ジオン化合物および農園芸用殺菌剤
JP2019163223A (ja) １，３，５，６−テトラ置換チエノ［２，３−ｄ］ピリミジン−２，４（１Ｈ，３Ｈ）ジオン化合物および農園芸用殺菌剤
JP2020147544A (ja) キノリン化合物および農園芸用殺菌剤
WO2018097172A1 (fr) Composé phényle guanidine, et bactéricide
WO2018097126A1 (fr) Composé guanidine, et bactéricide
JP2020040947A (ja) １，３，５，６−テトラ置換チエノ［２，３−ｄ］ピリミジン−２，４（１Ｈ，３Ｈ）ジオン化合物及び農園芸用殺菌剤
JP2022035834A (ja) ２，４－ジオキソ－１，４－ジヒドロチエノピリミジン化合物及び農園芸用殺菌剤
JP2023078623A (ja) ３－置換チエノピリミジンジオン化合物を含有する農園芸用殺菌剤
JP2020147545A (ja) オキサジアゾール化合物および農園芸用殺菌剤
WO2020189525A1 (fr) Composé hétérocyclique et bactéricide agricole ou horticole
WO2024143338A1 (fr) Composé hétéroaryle à cinq chaînons et bactéricide agricole et horticole
JP2020203883A (ja) ２，４−ジオキソ−１，４−ジヒドロチエノピリミジン化合物及び農園芸用殺菌剤
JP2023003357A (ja) オキサジアゾール化合物および農園芸用殺菌剤

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 15812571

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2016529594

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 15812571

Country of ref document: EP

Kind code of ref document: A1