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WO2014065411A1 - Sulfonamide derivative as harmful-organism control agent for agricultural/horticultural use - Google Patents

Sulfonamide derivative as harmful-organism control agent for agricultural/horticultural use Download PDF

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Publication number
WO2014065411A1
WO2014065411A1 PCT/JP2013/079010 JP2013079010W WO2014065411A1 WO 2014065411 A1 WO2014065411 A1 WO 2014065411A1 JP 2013079010 W JP2013079010 W JP 2013079010W WO 2014065411 A1 WO2014065411 A1 WO 2014065411A1
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carbon atoms
linear
branched
group
branched alkyl
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PCT/JP2013/079010
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French (fr)
Japanese (ja)
Inventor
正明 酒井
誠 番場
博 宮副
貴男 長野
新一郎 ▲高▼島
貴俊 坂口
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株式会社エス・ディー・エス バイオテック
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Priority to JP2014543367A priority Critical patent/JPWO2014065411A1/en
Publication of WO2014065411A1 publication Critical patent/WO2014065411A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
    • 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
    • C07D213/61—Halogen atoms or nitro radicals
    • 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
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a novel sulfonamide derivative that is useful as a pest control agent, particularly a pest control agent for agriculture and horticulture.
  • Patent Documents 1 to 24 and Non-Patent Documents 1 to 11 it is known that various sulfonamide derivatives have pest control activity.
  • the sulfonamide derivative of the present invention is a novel compound and is not known to have agricultural and horticultural pest control activities.
  • An object of the present invention is to provide a novel sulfonamide derivative and an agricultural and horticultural pest control agent containing the derivative as an active ingredient.
  • the present invention is as follows.
  • the first invention relates to a sulfonamide derivative represented by the following formula [I].
  • R 1 , R 2 , R 3 , R 4 are each a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R , —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, or linear or branched alkynyl having 2 to 8 carbon atoms.
  • Haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (same or different, 1 halogen atom A linear or branched alkenyl group having 2 to 6 carbon atoms substituted with ⁇ 4, and a haloalkoxy (identical or different, the number of carbon atoms substituted with 1 to 9 halogen atoms is 1 1-4 linear or branched alkoxy groups), acylalkoxy ((linear or branched aliphatic hydrocarbon group having
  • alkoxyalkyl straight or straight-chain 1 to 3 carbon atoms substituted with 1 to 5 straight-chain or branched alkoxy groups having 1 to 8 carbon atoms
  • Linear or branched alkyl group haloalkoxyalkyl (same or different, linear or branched 1 to 5 halo having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms)
  • an alkylthioalkyl a linear or branched alkyl group having 1 to 8 carbon atoms having 1 to 8 carbon atoms
  • Substituted carbon field A linear or branched alkyl group of 1 to 3), dialkoxy acetal (a dialkoxymethyl group in which a linear or branched alkoxy group having 1 to 8 carbon atoms is substituted with two methyl groups)
  • a linear or branched alkyl group having 1 to 3 carbon atoms substituted with 1 to 5 cyano groups), halogen, cyano, nitro, amino, Hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothia , Benzoxazolyl, Benzookisoriru, imide, formyl (-CHO), a carboxyl (-COOH), an oxo ( O) may be substituted with 1 to select to 7 substituents from. ]
  • the second invention is a method for producing a sulfonamide derivative represented by the formula [I].
  • the third invention is a pest control agent comprising one or more sulfonamide derivatives represented by the formula [I] as an active ingredient.
  • novel sulfonamide derivative of the present invention represented by the formula [I] has an excellent control effect against pests, particularly agricultural and horticultural pests.
  • the sulfonamide derivative in the present invention includes a salt (sodium salt, potassium salt, magnesium salt, calcium salt, aluminum salt, etc.), hydrate, Also included are solvates, crystalline polymorphic substances, and N-oxides of sulfonamide derivatives of formula [I]. Furthermore, all possible stereoisomers or optical isomers present in the compound of the present invention, and a mixture containing two or more kinds of isomers in any ratio are also represented by the compound of the present invention (sulfonamide derivative represented by the formula [I]). ).
  • R 1 , R 2 , R 3 , R 4 , A and B represented by the compound [I] are as follows.
  • R 1 is a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, — C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon atom having 3 to 8 carbon atoms 3 to
  • R 2 , R 3 and R 4 are each a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, — C (O) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is the number of carbon atoms 1-8 linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or 3 to 3 carbon atoms 8 cycloalkyl
  • Alkyl group), hydroxyalkyl A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 hydroxyl groups), alkoxyalkyl (linear or branched 1 to 5 carbon atoms having 1 to 8 carbon atoms) Linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 alkoxy group), haloalkoxyalkyl (the same or different, the number of carbon atoms substituted with 1 to 9 halogen atoms is A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 4 straight or branched 1 to 5 haloalkoxy groups, alkylthioalkyl (having 1 to 3 carbon atoms) 8 linear or branched alkyl groups having 1 to 3 carbon atoms substituted with 1 to 5 linear or branched alkylthio groups), dialkoxyacetals (having 1 to 8 carbon atoms) Linear or branched alkoxy Is
  • A is phenylene, 5- or 6-membered heteroarrangeyl (heteroarene contains 1 to 3 N, O, and S atoms in the ring, and both phenylene and heteroarrangeyl are —C (O) OR , —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, — NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (wherein R is linear or branched alkyl having 1 to 8 carbon atoms, and having 2 to 8 carbon atoms) Line
  • alkoxyalkyl straight or straight-chain 1 to 3 carbon atoms substituted with 1 to 5 straight-chain or branched alkoxy groups having 1 to 8 carbon atoms
  • Chain or branched alkyl group haloalkoxyalkyl (same or different, linear or branched 1 to 5 carbon atoms having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms)
  • Straight chain or branched alkyl group having 1 to 3 carbon atoms substituted with a haloalkoxy group straight chain or branched alkyl group having 1 to 3 carbon atoms substituted with a haloalkoxy group
  • alkylthioalkyl straight chain or branched alkyl group having 1 to 8 carbon atoms
  • dialkoxyacetal dialkoxymethyl group in which a straight-chain or branched alkoxy group having 1 to 8 carbon atoms is substituted
  • B is selected from any of the following a) to e).
  • B represents —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O ) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, — NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, ⁇ NOR, —SO 2 NHR, —SO 2 NR 2 (where R is the number of carbon atoms 1-8 linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or 3 to 3 carbon atoms 8 cycloalkyl
  • R 1 includes a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O ) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon having 3 to 8 carbon atoms A cycl
  • a ring and an oxazole ring can be mentioned, a benzene ring is preferable.
  • R 2 , R 3 and R 4 are each a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O ) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is a carbon atom) Linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or 3 carbon atoms ⁇
  • A represents phenylene, and substituents include —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O ) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, — NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (wherein R is 1 to 8 carbon atoms) Linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cyclocarbon having 3 to 8 carbon atoms.
  • alkyl or cycloalkenyl carbon atoms 3 ⁇ 8 alkyl or cycloalkenyl carbon atoms 3 ⁇ 8
  • - SiR 5 R 6 R 7, -OSiR 5 R R 7 R 5, R 6 , R 7 linear or branched alkyl having 1 to 6 carbon atoms, two or all phenyl may be all be the same substituent is different substituents
  • haloalkyl Linear or branched alkyl groups having 1 to 4 carbon atoms, which are the same or different and substituted with 1 to 9 halogen atoms, haloalkenyl (identical or different, and having 1 to 4 halogen atoms) Straight or branched alkenyl groups having 2 to 6 carbon atoms), haloalkoxy (identical or different, and having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Linear or branched alkoxy group), acylalkoxy ((linear or branched
  • SiR 5 R 6 R 7 R 5 , R 6 and R 7 are each 1 carbon atom
  • Alkyl group ), hydroxyalkyl (Linear or branched alkyl group having 1 to 3 carbon atoms substituted with 1 to 5 hydroxyl groups), alkoxyalkyl (linear or branched 1 having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by -5 alkoxy groups, a haloalkoxyalkyl (identical or different, carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a linear or branched 1 to 5 haloalkoxy group having 1 to 4 carbon atoms, alkylthioalkyl (the number of carbon atoms is 1 to 8 linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 linear or branched alkylthio groups), dialkoxy acetal (having 1 to 3 carbon atoms) 8 linear or branched alco A dial
  • 5- or 6-membered heteroarylene diyl in A includes oxazolediyl, isoxazolediyl, furandyl, thiazolediyl, isothiazolediyl , Pyrimidinediyl, pyrazinediyl, pyridinediyl, pyrrolediyl, thiophenediyl, imidazolediyl, and pyrazolediyl, and oxazolediyl, thiazolediyl, pyridinediyl, and thiophenediyl are preferable.
  • examples of the substituent include —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, — C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon atom having 3 to 8 carbon atoms 3) to
  • Monocyclic or bicyclic rings optionally containing 0 to 3 heteroatoms in B include phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, Isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzisothiazolyl, pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, benz Examples include imidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl, oxadiazolyl,
  • Examples of straight-chain or branched cycloalkyl having 3 to 8 carbon atoms or cycloalkenyl having 3 to 8 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s- Butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, vinyl, 1-propenyl, 2-propenyl, isopropenyl, ethynyl, propargyl, cyclopropyl , Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cycl
  • n- propyl group a vinyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group is preferred.
  • Alkyl eg, methyl, ethyl, n-propyl, isopropyl
  • alkoxy eg, methoxy, ethoxy, n-propoxy, isopropoxy
  • halogen eg, fluorine, chlorine, bromine
  • 1 to 7 atoms, cyano, haloalkyl for example, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group
  • benzyloxy group, and phenoxy group are substituted.
  • R 5 , R 6 , R 7 in B is linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and even if two or all are the same substituents, Examples of different substituents include a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a t-butyldimethylsilyl group, and a t-butyldiphenylsilyl group, with a trimethylsilyl group and a triethylsilyl group being preferred.
  • —C (O) OR —C (O) NHR, —C (O) NR 2 , —SO 2 NHR, —SO 2 NR 2 (where R is a carbon atom having 1 to 8 carbon atoms) Linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms Or cycloalkenyl, benzyl or cyclic ether having 3 to 8 carbon atoms), halogen, formyl (—CHO) or carboxyl (—COOH).
  • alkyl refers to a linear or branched alkyl group having 1 to 8 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group. And isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, and n-octyl groups.
  • alkenyl refers to a linear or branched alkenyl group having 2 to 8 carbon atoms, such as an ethenyl group, a 1-propenyl group, a 2-propenyl group, an isopropenyl group, 1 -Butenyl group, 2-butenyl group, 3-butenyl group and the like can be mentioned.
  • alkynyl refers to a linear or branched alkynyl group having 2 to 8 carbon atoms, for example, ethynyl group, 2-propynyl group, 2-butynyl group, or 3-butynyl group. Groups and the like.
  • cycloalkyl refers to a cycloalkyl group having 3 to 8 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • cycloalkenyl refers to a cycloalkenyl group having 3 to 8 carbon atoms, such as a 1-cyclopentyl group, 2-cyclopentyl group, 3-cyclopentyl group, 1-cyclohexyl group, 2- A cyclohexyl group or a 3-cyclohexyl group can be mentioned.
  • heteroatom includes a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom.
  • halogen includes fluorine, chlorine, bromine and iodine.
  • halo in “halo...” (For example, “haloalkyl”) includes fluorine, chlorine, bromine and iodine.
  • haloalkyl is the same or different and represents a linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms. Examples thereof include a fluoromethyl group, a monochloromethyl group, a monobromomethyl group, a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, an n-heptafluoropropyl group, and an isoheptafluoropropyl group.
  • haloalkenyl is the same or different and represents a linear or branched alkenyl group having 2 to 6 carbon atoms, which is substituted with 1 to 4 halogen atoms. , 2-difluoroethenyl group, 2,2-difluoroethenyl group, 3,3-difluoro-2-propenyl group, and the like.
  • alkoxy refers to an (alkyl) -O— group in which the alkyl moiety has the above meaning, for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group. , S-butoxy group, t-butoxy group and the like.
  • haloalkoxy refers to a (haloalkyl) -O— group in which the haloalkyl moiety has the above meaning, for example, a monofluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, 2,2-difluoro An ethoxy group, a 2,2,2-trifluoroethoxy group, etc. can be mentioned.
  • acyl or the term “acyl” in acylalkoxy, the term “acyl” in acyloxyalkyl, and the term “acyl” in acyloxy are all (with 1 to 8 carbon atoms).
  • the aliphatic hydrocarbon group means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkynyl.
  • acylalkoxy refers to a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by 1 to 5 acyl groups as described above. Group, acetylethoxy group, acetylpropoxy group and the like.
  • acyloxy refers to a (linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— group, for example, an acetoxy group, propionyloxy group , An isopropionyloxy group, or a pivaloyloxy group.
  • acyloxyalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 acyl groups as described above, for example, acetoxymethyl A group, an acetoxyethyl group, an acetoxypropyl group, and the like.
  • alkylsulfonyl refers to an (alkyl) -SO 2 — group in which the alkyl moiety has the above meaning, for example, a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, or an isopropylsulfonyl group. Examples include groups.
  • alkylsulfonylalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 alkylsulfonyl groups shown above, for example, A methylsulfonylmethyl group, a methylsulfonylethyl group, or a methylsulfonylpropyl group can be exemplified.
  • the term “siloxy” refers to —OSiR 5 R 6 R 7 (R 5 , R 6 , R 7 are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, two All may be the same substituents or all different substituents), for example, trimethylsiloxy group, triethylsiloxy group, triisopropylsiloxy group, t-butyldimethylsiloxy group, t-butyldiphenylsiloxy group, etc. Can do.
  • siloxyalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 siloxy groups shown above, for example, trimethylsiloxy Examples thereof include a methyl group, a trimethylsiloxyethyl group, a trimethylsiloxypropyl group, a triethylsiloxymethyl group, and a t-butyldimethylsiloxy group.
  • hydroxyalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 hydroxyl groups, such as a hydroxymethyl group, hydroxyethyl group, and the like. Group, hydroxypropyl group, hydroxyisopropyl group and the like.
  • alkoxyalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 alkoxy groups as described above, for example, methoxymethyl A group, an ethoxymethyl group, a propoxymethyl group, or an isopropoxymethyl group.
  • alkylthio refers to an (alkyl) -S— group in which the alkyl moiety has the above meaning, and examples include a methylthio group, an ethylthio group, or a propylthio group.
  • haloalkylthio refers to a (haloalkyl) -S— group in which the haloalkyl moiety is as defined above, for example, a monofluoromethylthio group, a difluoromethylthio group, a trifluoromethylthio group, 2,2- A difluoroethylthio group or a 2,2,2-trifluoroethylthio group can be exemplified.
  • alkylthioalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 alkylthio groups shown above, for example, methylthiomethyl A group, an ethylthiomethyl group, a methylthioethyl group, or an ethylthioethyl group.
  • dialkoxyacetal refers to a dialkoxymethyl group in which the above-mentioned alkoxy group is substituted by two methyl groups, such as a dimethoxymethyl group, a diethoxymethyl group, or a dipropoxymethyl group. Can be mentioned.
  • alkoxyalkoxy refers to a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by 1 to 5 alkoxy groups as described above, for example, methoxymethoxy Group, methoxyethoxy group, methoxypropoxy group and the like.
  • haloalkoxyalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 haloalkoxy groups as described above.
  • a monofluoromethoxymethyl group, a difluoromethoxymethyl group, a trifluoromethoxymethyl group, etc. can be mentioned.
  • cyanoalkyl represents a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups, such as a cyanomethyl group, a cyanoethyl group, Or a cyanopropyl group etc. can be mentioned.
  • phenoxy includes a phenoxy group having one or more substituents which may be the same or different, and an unsubstituted phenoxy group.
  • benzyl includes a benzyl group having one or more substituents which are the same or different and an unsubstituted benzyl group.
  • benzyloxy includes a benzyloxy group having one or more substituents which are the same or different and an unsubstituted benzyloxy group.
  • propargyl includes propargyl groups having a substituent at the alkyne end and unsubstituted propargyl groups.
  • propargyloxy includes a propargyloxy group having a substituent at the alkyne end and an unsubstituted propargyloxy group.
  • heteroaryl is oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, Includes benzoisothiazolyl, pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl, ferrocenyl .
  • These groups may have
  • phenylene includes 1,2-phenylene (o-phenylene), 1,3-phenylene (m-phenylene) and 1,4-phenylene (p-phenylene). These groups may have one or more substituents which may be the same or different, and may not have a substituent.
  • the term “5- or 6-membered heteroallene” containing 1 to 3 N, O, S atoms in the ring represents an aromatic heterocycle having 5 or 6 ring atoms, for example, Examples thereof include oxazole, isoxazole, furan, thiazole, isothiazole, pyrimidine, pyrazine, pyridine, pyrrole, thiophene, imidazole, and pyrazole.
  • the term “5- or 6-membered heteroarrangeyl” is a divalent group derived from the aromatic heterocycle having 5 or 6 ring atoms shown above, and the position of the bond at two positions.
  • oxazolediyl isoxazolediyl, furandyl, thiazolediyl, isothiazolediyl, pyrimidinediyl, pyrazinediyl, pyridinediyl, pyrroldiyl, thiophenediyl, imidazolediyl
  • cyclic ether includes epoxy, oxetane, tetrahydrofuran, tetrahydropyran, dioxolane, and dioxane.
  • cyclic amine includes pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholinyl.
  • the term “imide” includes a chain imide and a cyclic imide.
  • acids that form acid addition salts include inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, and phosphoric acid, formic acid, acetic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, and aconite.
  • examples thereof include carboxylic acids such as acids, and sulfonic acids such as methanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid.
  • the present compound [I] represented by the following formula comprises, for example, a sulfonic acid derivative represented by the general formula [II] and an amine derivative represented by the general formula [III] as a base ) And a solvent in the presence of a solvent.
  • R 1 , R 2 , R 3 , R 4 , A and B are as defined above.
  • the term “pest” includes all pests on agricultural and horticultural plants and all pathogenic fungi on agricultural and horticultural plants.
  • pathogenic fungi against agricultural and horticultural plants examples include Plasmodiophoromycota, Omyycota, Zygomycota, Ascomycota, Basidiomycota, Incomplete fungus ( Deuteromycota) and bacteria belong, and the sulfonamide derivative according to the present invention can control plant diseases caused by these pathogenic fungi.
  • specific names of bacteria are given as examples, but are not necessarily limited thereto.
  • Examples of agricultural and horticultural pathogens include, for example, rice blast (Pyricularia oryzae), rice sesame leaf blight (Cochliobolus miyabeanus), rice blight (Rhizoctonia solani), rice idiot (Gibberella fujikuroi), wheat red mold (Gibberella zeae) ), Wheat red rust (Puccinia recondita), wheat powdery mildew (Erysiphe graminis f.sp.
  • Onion sclerotia (Sclerotinia sclerotiorum), onion black spot blight (Septoria alliacea), onion black spot (Alternaria porri), onion rust (Puccinia allii), onion small sclerotia (Sclerotinia allii), small onion Botrytis squamosa, onion white plague (Phytophthora porri), onion anthracnose (Colletotrichum circinans), onion gray mold (Botrytis cinerea), onion gray rot (Botrytis a llii), onion leaf blight (Pleospora herbarum), onion downy mildew (Peronospora destructor), leek rust (Puccinia allii), leek white leaf blight (Botrytis byssoidea), leek plague (Phytophthora nicotianae), leek wilt ( Fusarium oxysporum f
  • pests and mites on agricultural and horticultural plants examples include the order of Hemiptera, Thysanoptera, Lepidoptera, Acari, etc., and the sulfonamide derivatives used in the present invention Can control plant damage caused by these pests, mites and the like.
  • specific pests, ticks and the like are given as examples, but not necessarily limited thereto.
  • pests and mites include, for example, Cossus insularis, Adoxophyes honmai, Adoxophyes orana faciata, Nashihimeshini (Grapholita molesta), Chamonakisuna (Homona magnamina) Leguminivora glycinivorella), Ginmon leafworm (Lyonetia prunifoliella malinella), Chanohosuga (Caloptilia theivora), Butterberry leafworm (Phyllonorycter ringoniella), Citrus leaflet (Phyllocnistis citrella), Negikoga (Acrol) conjugella), Grape squirrel (Nokona regalis), Cosca squirrel (Synanthedon hector), Oyster moth (Stathmopoda candidssa), Peach moth (Carposina sasakii), Iraga (Monema flavescens), Nikaameiga (Chilo supcroscis), Hellul
  • Thrips palmi, Thrips tabaci, etc., Thrips tabaci Tomato leaf fly (Liriomyza sativae), red fly (Delia platura), onion fly (Delia antiqua), ring fly (Rhagoletis pomonella), fly fly (Mayetiola destructor), house fly (Musca domestica), sand flies (calcium calculi) White flies (Melophagus ovinus), Hypoderma lineatum, Bullflies (Hypoderma bovis), Swallow flies (Oestrus ovis), Tsetse flies (Glossina Telmatoscopus albipunctatus), Toepanakanuka (Leptoconops nipponensis), Culex pipipiens ⁇ ⁇ pallens, Aedes albopicutus, Aedes aegypsin rosae ruficornis), pine bee (Neodiprion sertifer),
  • Gryllotalpa Termite pests cat fleas (Ctenocephalidae felis), human fleas (Pulex irritans), flea fleas such as Xenopsylla cheopis, chicken lice (Menacanthus (Haematopinus eurysternus) Mi (Linognathus vituli), Kebukaushijirami (Solenopotes capillatus) Anoplura pests such as.
  • spider mites Panonychus citri
  • apple spider mites Panonychus ulmi
  • Kanzawa spider mites Tinychus kanzawai
  • spider mite Tetranychus urticae
  • Tulip spider mites Tulip spider mites (Aceria Aculops pelekassi, etc., Robin tick (Rhizoglyphus robini), Spinach mite (Tyrophagus similis), Dust mites (Polyphagotarsonemus latus), etc.
  • Ticks such as ticks (Boophilus microplus), ticks (Haemaphysalis longicornis), cucumber ticks (Psoroptes ovis), sword mites (Sarcoptes scabiei), etc.
  • Other crustaceans such as Armadillidium vulgare, sweet potato root nematode (Meloidogyne incognita), fox root nematode (Meloidogyne hapla), potato cyst nematode (Globodera rostochiensis) (Heterodera , Nematodes (Ponacea canaliculata), slug apple moth (Ponacea canaliculata), slug apple moth (Meghimat cus ), And mollusks such as Lehmannina iana valentiana.
  • the agricultural and horticultural pest control agent of the present invention is particularly effective in sterilizing effect and insecticidal effect, and contains one or more compounds represented by the formula [I] as active ingredients.
  • the compound of the present invention represented by the formula [I] is applied to the plant by spraying, spraying, applying, or the like with the active ingredient, or sowing the seed of the plant or the soil or seed around the plant. It can be performed by treating soil, paddy field, hydroponics water with active ingredients.
  • the application can be done before or after the plant is infected with the pathogen.
  • application can be performed before or after the occurrence of pests.
  • This compound is in the form of normal preparations such as granules, powders, aqueous solvents, oils, emulsions, microemulsions, suspoemulsions, solutions, wettable powders, emulsions, suspensions, tablets, granules It can be used as an agent suitable for agricultural and horticultural pest control agents such as wettable powders, microcapsules, aerosols, pastes, jumbo agents, powders, smoke agents, fumigants and the like.
  • Such embodiments include at least one compound of the invention and a suitable solid or liquid carrier, and, if desired, suitable adjuvants (eg, surfactants) to improve the dispersibility of the active ingredient and other properties.
  • suitable adjuvants eg, surfactants
  • solid carriers or diluents include plant materials (eg, crystalline cellulose, starch, wood flour, cork, coffee husk, etc.), fibrous materials, artificial plastic powders, clays (eg, kaolin, bentonite) , White clay, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, acid clay, etc., talc and minerals (eg, vermulite, montmorillonite, pumice, sulfur powder, apatite, mica, sericite, quartz powder, activated carbon, calcium carbonate Etc.), polymer compounds (polyvinyl chloride, petroleum resins, etc.), chemical fertilizers (eg, ammonium sulfate, phosphorous acid, ammonium nitrate, ammonium chloride, calcium chloride, urea, etc.).
  • plant materials eg, crystalline cellulose, starch, wood flour, cork, coffee husk, etc.
  • fibrous materials eg, artificial plastic powders, clays (
  • Liquid carriers and diluents include water, alcohols (eg, methanol, ethanol, isopropanol, cyclohexanol, etc.), ketones (eg, acetone, methyl ethyl ketone, cyclohexanone, etc.), ethers (eg, ethyl cellosolve, butyl cellosolve) , Dioxane, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (eg, kerosene, paraffin, etc.), and swells (eg, isopropyl acetate, benzyl acetate, etc.) Nitriles, amides (eg, N, N-dimethylformamide, dimethyl sulfoxide, etc.), halogenated hydrocarbons (eg, chlor
  • gaseous carriers examples include carbon dioxide gas, butane gas, and fluorocarbon.
  • surfactants include various anionic surfactants and nonionic surfactants conventionally used in the field of agrochemical formulations.
  • anionic surfactant include sulfonic acid-based surfactants such as alkyl sulfonic acid, alpha olefin sulfonic acid, lignin sulfonic acid, alkylbenzene sulfonic acid, alkyl naphthalene sulfonic acid, naphthalene sulfonic acid formalin condensate, and dialkyl sulfosuccinate.
  • Surfactants and salts thereof higher fatty acid salts, polycarboxylic acid type surfactants and salts thereof, and the like.
  • the salts in the above surfactants include salts of sodium, potassium, magnesium, calcium, ammonium, ethanolamine, diethanolamine, triethanolamine, various amines and the like.
  • Examples of the nonionic surfactant include polyoxyethylene alkyl allyl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene alkyl ether, polyoxyethylene phenyl alkyl allyl ether, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycol.
  • Polyoxyethylene alkyl ester polyoxyethylene polyoxypropylene block copolymer, polyoxyalkylene glycol, alkyne diol (acetylene glycol), alkynylene polyoxyethylene diol, sorbitan fatty acid ester, alkyl aryl ether formalin condensate, etc. it can.
  • Stabilizers include isopropyl phosphate mixture, tricresyl phosphate, true oil, epoxy oil, surfactants, fatty acids and esters thereof.
  • the compounds of the present invention can be formulated in admixture with other fungicides, insecticides, herbicides, or fertilizers.
  • the above-mentioned preparation contains 1 to 95% by weight, preferably 1 to 50% by weight, of at least one compound [I] of the present invention.
  • These preparations can be used alone or diluted, and the compound [I] of the present invention is used in an amount of about 1 to 5 kg / ha, preferably about 2 to 100 g / ha, usually about 1 to 50000 ppm, preferably about Used at a concentration of 50-1000 ppm.
  • the compound of the present invention represented by the formula [I] can be used alone or as a preparation thereof, but a bactericidal / fungicidal agent, bactericidal agent, acaricide, nematicide, insecticide, biological pesticide, A mixture of herbicides, plant hormones, plant growth regulators, synergists, attractants, repellents, pigments, fertilizers, etc., or a mixture of one or more selected from those active ingredients
  • the preparation can also be used as a pest control agent. There, it can be expected that the action, pests to be controlled, expansion of the appropriate period of use, or reduction of dosage, synergistic effect, or prevention of development of resistance, etc. Shinogi, cooperative medicinal effects with joint ingredients are achieved.
  • bactericides include SH group enzyme inhibitory compounds, nucleic acid synthesis inhibitory active compounds, spindle yarn formation inhibitory active compounds, benzanilide compounds, strobilurin compounds, other electron transport inhibitory compounds, amino acid synthesis inhibitory active compounds, sterols Biosynthesis inhibitory active compounds, signal signal transduction inhibitory active compounds, lipid synthesis inhibitory active compounds, cell wall biosynthesis inhibitory active compounds, melanin synthesis inhibitory active compounds, host resistance-inducing compounds, other compounds with unclear effects, etc. be able to.
  • SH group enzyme inhibitory active compounds chlorothalonil, dithianon, captan, folpet, iminoctadine-albesilate, iminoctadine-triacetate, farbum ( ferbam), nabam, mancozeb, manneb, maneb, metiram, propineb, polycarbamate, thiram, zineb, ziram, oxidation Cupric oxide, cupric hydroxide, basic copper oxychloride, anhydrous copper sulfate (copper oppsulfate (anhydride)), copper sulfate (copper sulfate), sulfur, etc. .
  • Nucleic acid synthesis inhibitory active compounds metalaxyl, metalaxyl-M, oxadixyl, bupirimate, hymexazol, oxolinic acid, etc.
  • Benzanilide compounds flutolanil, mepronil, fluopyram, carboxin, oxycarboxin, thifluzamide, bixafen, fluxapyroxad, Furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid and the like.
  • Stravylline compounds azoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, kresoxim-methyl, trif Roxystrobin, dimoxystrobin, metominostrobin, orysastrobin, famoxadone, fenamidone, pyribencarb, etc.
  • Amino acid synthesis inhibitory active compounds cyprodinil, mepanipyrim, pyrimethanil, blasticidin-S, kasugamycin, streptomycin, oxytetracycline, and the like.
  • Sterol biosynthesis inhibiting active compounds fenarimol, imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole, azaconazole, bitertanol ), Bromuconazole, cyproconazole, difenoconazole, epoxiconazole, fenbuconazole, flutriafol, hexaconazole, imicon Benconazole (imibenconazole), Metoconazole (metoconazole), Microbutanil (myclobutanil), Penconazole (propconazole), Cimeconazole (simeconazole), Tebuconazole (tebuconazole), Tetraconazole (triconon), Triimmephone (triimon) G Adimenol, triticonazole, fenpropimorph, tridemorph, piperalin, spiroxamine, fenhexamid, pyributicarb, nap
  • Signal signal transduction inhibitory compounds quinoxyfen, proquinazid, fludioxonil, iprodione, procymidone, vinclozolin, microzoline, etc.
  • Lipid synthesis inhibitory active compounds iprobenfos, isoprothiolane, quintozene, propamocarb, prothicarb and the like.
  • Cell wall biosynthesis inhibitory active compounds validamycin, polyoxin B, dimethomorph, benthiavalicarb, iprovalicarb, valifenalate, mandipropamid, etc.
  • Melanin synthesis inhibitory active compounds pyroquilon, tricyclazole, carpropamid, diclocymet, fenoxanil and the like.
  • Host resistance-inducing compounds acibenzolar-S-methyl, probenazole, isotianil, laminarin and the like.
  • insecticides / acaricides / nematicides include acetylcholinesterase inhibitor compounds, GABA-acting chloride channel inhibitor compounds, sodium ion channel inhibitor compounds, nicotinic acetylcholine receptor inhibitor compounds, chloride ion active compounds, Juvenile hormone analogues, non-selective inhibitory compounds, homozygous selective feeding inhibitory compounds, mite growth inhibitory compounds, microorganism-derived insect midgut membrane disruptors, ATP synthesis inhibitory compounds, oxidative phosphorylation uncoupling compounds Nicotinic acetylcholine receptor channel inhibitor compound, chitin biosynthesis inhibitor compound, molting / metamorphosis inhibitor compound, octopamine receptor agonist compound, electron transport system inhibitor compound, voltage-gated sodium channel inhibitor compound, lipid synthesis inhibitor compound, ryanodine receptor inhibitor Compound, other or unclear effects And the like.
  • Acetylcholinesterase-inhibiting compounds aldicarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenobucarb, methiocarb, methomyl, oxamyl ), Thiodicarb, acephate, cadusafos, chlorpyrifos, diazinon, dichlorvos, dimethoate, EPN, fenamiphos, fenitrothion, fenitrothion, fenitrothion (fosthiazate), imacyafos, malathion, methamidophos, monocrotophos, methylthalathion, parafenion, profenofos, terbufos and the like.
  • GABA-acting chloride ion channel-inhibiting compounds endosulfan, ethiprole, fipronil, acetoprole and the like.
  • Sodium ion channel blocking compounds acrinathrin, allethrin, bifenthrin, lambda-cyhalothrin, cypermethrin, etofenprox, fenvalerate, permethrin (permethrin), DDT, methoxychlor, tefluthrin, etc.
  • Nicotinic acetylcholine receptor inhibitory compounds acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, etc. Spinetoram, spinosad, etc.
  • Chloride ion channel active compounds abamectin, emamectin benzoate, lepimectin, milbemectin and the like.
  • Juvenile hormone analogs kinoprene, metoprene, phenoxycarb, pyriproxyfen, etc.
  • Non-selective inhibitory compounds methyl bromide, chloropicrin, etc.
  • Homogeneous selective feeding inhibitory compounds pymetrozine, flonicamid, etc.
  • Tick growth inhibitory compounds clofentezine, hexythiazox, etoxazole, etc.
  • Microorganism-derived insect midgut membrane destroyer Bacillus thuringiensis, etc.
  • ATP synthesis inhibiting compounds diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon, etc.
  • Oxidative phosphorylation uncoupling compounds chlorfenapyr and the like.
  • Nicotinic acetylcholine receptor channel inhibitory compounds bensultap, cartap hydrochloride, thiocyclam, etc.
  • Chitin biosynthesis inhibiting compounds chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron triflumuron, buprofezin, bistrifluron, noviflumuron and the like.
  • Molting / metamorphosis inhibiting compounds cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide and the like.
  • Octopamine receptor agonist compound amitraz and the like.
  • Electron transport inhibitor hydramethylnon, acequinocyl, fluacrypyrim, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tebufenpyrad, tebufenpyrad tolfenpyrad), rotenone, aluminum phosphide, cyenopyrafen, cyflumetofen and the like.
  • Voltage-gated sodium channel inhibitor compounds indoxacarb, metaflumizone, etc.
  • Lipid synthesis inhibiting compounds spirodiclofen, spiromesifen, spirotetramat and the like.
  • Ryanodine receptor inhibitor compounds chlorantraniliprole, cyantraniliprol, flubendiamide and the like.
  • herbicides include the following compounds.
  • Lipid synthesis inhibitors fluazifop- butyl, quizalofop-ethyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl -P-ethyl, alloxydim, sethoxydim, metamifop, esprocarb, prosulfocarb, pyributicarb, benfuresate, etofumesate and the like.
  • Acetolactate synthase (ALS) inhibitors amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, cinosulfuron, cyclosulfam Cyclosulfamuron, ethoxysulfuron, pyrazosulfuron-ethyl, foramsulfuron, imazosulfuron, iodosulfuron, chlorosulfuron, thiosulfuron Methyl (thifensulfuron-methyl), flazaslfuron (flazaslfuron), pyriminobac-methyl, florasulam, imazapyr, imazamox, imazaquin, imazoquin, mesosulfuron methyl methyl), dimefuron, propoxy Rubazone (propoxycarbazone), full carbazone (flucarbazone), metosulam, penoxsulam, flucetosulfuron,
  • Photosynthesis electron transport system inhibitors Simazine, metribuzin, amicarbazone, diuron, linuron, ioxynil, dimethametryn, phenmedipham, oxadiargyl (oxadiargyl), desmedipham, isoproturon, neburon, bromoxynil, methabenzthiazuron, metamitron, paraquat, diquat, Atrazine, flufenpyr-ethyl, bentazone, etc.
  • Protox inhibitors bifenox, lactofen, flumioxazin, carfentrazone-ethyl, pentoxazone, pyraclonil, pyraflufen- ethyl), oxadiazon, sulfentrazone, acifluorfen-sodium, fluthiacet-methyl and the like.
  • 4-HPPD inhibitors mesotrione, isoxaflutole, benzofenap, benzobicyclon, topramezone, sulcotrione, tefyltrione ), Pyrasulfotole, pyrazoxifene, pyrazolate, and the like.
  • Carotenoid biosynthesis inhibitors aclonifen, flurtamone, diflufenican, fluridone, etc.
  • EPSP synthase inhibitor glyphosate and the like.
  • Glutamate synthase inhibitors glufosinate-ammonium, bialaphos, etc.
  • Cell division inhibitor oryzalin, pendimethalin, butamifos, carbetamide, triaziflam, flupoxam, dichlobenil, IPC (propham), trifluralin ), Cumyluron, indaziflam and the like.
  • VLCFAs inhibitors alachlor, metolachlor, tenenylchlor, mefenacet, fentrazamide, cafenstrole, pretilachlor, indanofan, anilofos Flufenacet, napropamide, dimethenamid, propisochlor, fenoxasulfone, ipfencarbazone and the like.
  • Auxin-active herbicides Chromeprop, 2,4-D, MCPA, MCPB, MCPP, triclopyr, etc.
  • Oxidative phosphorylation uncouplers dinoterb, tribufos, ethephon, thidiazuron, cyclanilide, saflufenacil, isoxadifen, ethiozin, etc.
  • biological pesticides include (1) Nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), etc. (2) Steinernema carpocapsae, Steinernema glaseri, Monocrosporium phymatophagum, Steinernema kushidai, Steinernema kushidai etc. (3) Agrobacterium radiobacter, Bacillus subtilis, Erwinia carotovora, Pseudomonas fluorescens, Talaromyces flavus, Talaromyces flavus, (Trichoderma atroviride) etc.
  • NDV Nuclear polyhedrosis virus
  • GV granulosis virus
  • CPV cytoplasmic polyhedrosis virus
  • Steinernema carpocapsae Steinernema glaseri
  • Monocrosporium phymatophagum Steinernema kushidai
  • Examples of pheromone agents include: chodrelua ((E, E) -8,10-Dodecadien-1-ol), beet armorua B ((Z) -9-Tetradecen-1-ol), tetradodecenyl Examples thereof include acetate ((Z) -11-Tetradecenyl acetate), pyrimalua (14-Methyl-1-octadecene), peach flua ((Z) -13-Eicosen-10-one), and the like.
  • Examples of natural fungicides and insecticides include machine oils (Machine oils), methylphenylacetate ( ⁇ ), pinned ( ⁇ -Pinene), protein hydrolysates (Protein hydrolysate), (Z) -1 -Tetradecen-1-ol, turpentine and the like.
  • Step C 4-Iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide
  • Step D N- (Quinolin-4-ylmethyl) -4-((trimethylsilyl) ethynyl) benzenesulfonamide
  • Step E 4-Ethynyl-N- (quinolin-4-ylmethyl) benzenesulfonamide
  • Table 1 Compound No. 2 to 4, 6 to 8, 11 to 16, 18 to 21, 23 to 28, 30 to 39, 41 to 45, 47 to 50, 52 to 55, 57 to 69, 71, 87, 97, 109 to 133, 135-140, 142-156, 158, 160-164, 170-177 were synthesized.
  • N- (2-ethynylphenyl) acetamide, N- (3-ethynylphenyl) acetamide, and N- (4-ethynylphenyl) acetamide are the corresponding anilines according to the method described in Patent Document 16 (US2004 / 87789). More manufactured.
  • 1,1-dichloro-2-methyl-2-ethynylcyclopropane was produced from the corresponding enyne according to the method described in Non-Patent Document 6 (Zhurnal Organicheskoi Kimii, 1982, 18, 2295.). As other acetylenes, commercially available products were used.
  • Table 1 Compound No. 10, 17, 22, 29, 40, 46, 51, 56, 70, 72 to 86, 88 to 96, 98 to 108, and 169 were synthesized.
  • 2-Fluoro-3-iodopyridine was produced from 2-fluoropyridine according to the method described in Non-Patent Document 7 (Tetrahedron, 1993, 49, 49.).
  • 2-Fluoro-4-iodopyridine was produced from 2-fluoro-3-iodopyridine according to the method described in Non-Patent Document 8 (Journal of Organic Chemistry, 1993, 58, 7832.).
  • 3-Iodo-2-methoxypyridine and 4-iodo-2-methoxypyridine were prepared from the corresponding fluoropyridines according to the method described in Patent Document 18 (WO2008 / 25509). As other aryl halides, commercially available products were used.
  • Step C of Synthesis 1 the sulfonamide compound was obtained by using 4-bromo-2-methylbenzenesulfonyl chloride instead of 4-iodobenzenesulfonyl chloride.
  • Step B 2-Methyl-4- (phenylethynyl) -N- (quinolin-4-ylmethyl) benzenesulfonamide
  • Step D of Synthesis 1 the sulfonamide compound obtained in the above step was used instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and phenylacetylene was used instead of trimethylsilylacetylene. 1, compound no. 178 was synthesized.
  • 5-bromopyridine-2-sulfonyl chloride, 6-bromopyridine-3-sulfonyl chloride, 5-bromofuran-2-sulfonyl chloride, 4-bromothiophene-2-sulfonyl chloride, 5-bromothiazole-2-sulfonyl chloride was prepared from the corresponding dihaloheterocyclic compound according to the method described in Non-Patent Document 9 (Synlett, 2011, (8), 1117.).
  • 2-Chloropyrimidine-5-sulfonyl chloride was prepared from 2-aminopyrimidine according to the method described in Patent Document 19 (WO 2006/29154).
  • 3-Bromothiophene-2-sulfonyl chloride was produced from 3-bromothiophene according to the method described in Patent Document 20 (WO 2004/074238). Commercially available products were used for the other sulfonyl chlorides.
  • step D of synthesis ethynyl compound is obtained by using 2,4-dibromothiazole instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide and phenylacetylene instead of trimethylsilylacetylene. It was.
  • Step B 2- (Phenylethynyl) thiazole-4-sulfonyl chloride
  • Step C 2- (Phenylethynyl) -N- (quinolin-4-ylmethyl) thiazole-4-sulfonamide
  • Step C of the synthesis of Compound 1 the sulfonyl chloride compound obtained in the above step was used in place of 4-iodobenzenesulfonyl chloride, so that Table 1, Compound No. 215 was obtained.
  • Step C of Synthesis 1 the sulfonamide compound was obtained by using the methanamine compound obtained in the above step instead of 4- (aminomethyl) quinoline.
  • Step E N-((2-chloroquinolin-4-yl) methyl) -4- (phenylethynyl) benzenesulfonamide
  • Step D of Synthesis 1 the sulfonamide compound obtained in the above step was used instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and phenylacetylene was used instead of trimethylsilylacetylene. 1, compound no. 218 was obtained.
  • Step C of Synthesis 1 sulfonamide compound was obtained by using 4-picolylamine instead of 4- (aminomethyl) quinoline.
  • Step B N- (Pyridin-4-ylmethyl) -4-((trimethylsilyl) ethynyl) benzenesulfonamide
  • step D of the synthesis of 1 trimethylsilyl compound was obtained by using the sulfonamide compound obtained in the above step instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide.
  • Step C 4-Ethynyl-N- (pyridin-4-ylmethyl) benzenesulfonamide
  • step E of the synthesis of 1 the trimethylsilyl compound obtained in the above step was used in place of N- (quinolin-4-ylmethyl) -4-((trimethylsilyl) ethynyl) benzenesulfonamide. . 219 was obtained.
  • Step B Ethyl 3- (4- (N- (tert-butoxycarbonyl) -N- (pyridin-4-ylmethyl) sulfamoyl) phenyl) propiolate
  • Step D of Synthesis 1 the carbamic acid compound obtained in the above step was used in place of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and ethyl propiolate was used in place of trimethylsilylacetylene. A propiolic acid compound was obtained.
  • Step C ethyl 3- (4- (N- (pyridin-4-ylmethyl) sulfamoyl) phenyl) propiolate
  • the propiolic acid compound obtained in the above step and 10 mL of trifluoroacetic acid were added to 10 mL of methylene chloride, and the mixture was stirred at room temperature for 1.5 hours.
  • the reaction solution was concentrated, and the residue was purified by silica gel flash chromatography (eluted with methanol-chloroform) using a flash automatic purifier (Biotage AB / Isolera TM ). 309 was obtained.
  • Step C of Synthesis 1 the sulfonamide compound was obtained by using 3-bromobenzenesulfonyl chloride in place of 4-iodobenzenesulfonyl chloride and 4-picolylamine in place of 4- (aminomethyl) quinoline.
  • Step B 3- (Phenylethynyl) -N- (pyridin-4-ylmethyl) benzenesulfonamide
  • Step D of Synthesis 1 the sulfonamide compound obtained in the above step was used in place of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and phenylacetylene was used instead of trimethylsilylacetylene.
  • Table 1 Compound No. 321 was synthesized.
  • step C of the synthesis of 215 4-picolylamine was used in place of 4- (aminomethyl) quinoline, so that Table 1, Compound No. 346 was obtained.
  • Step B 4- (Azidomethyl) -2-phenylpyridine
  • Step D 4-Iodo-N-((2-phenylpyridin-4-yl) methyl) benzenesulfonamide
  • Step C of Synthesis 1 the sulfonamide compound was obtained by using the methanamine compound obtained in the above step instead of 4- (aminomethyl) quinoline.
  • Step E 4- (Phenylethynyl) -N-((2-phenylpyridin-4-yl) methyl) benzenesulfonamide
  • Step D of Synthesis 1 the sulfonamide compound obtained in the above step was used instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and phenylacetylene was used instead of trimethylsilylacetylene. 1, compound no. 349 was obtained.
  • (3-Chloropyridin-4-yl) methanamine was prepared according to the method described above after the corresponding methanol was prepared according to the method described in Patent Document 25 (WO2010 / 132999).
  • (2-Chloro-6-methylpyridin-4-yl) methanamine and (2,6-dichloropyridin-4-yl) methanamine were prepared according to the method described in Non-Patent Document 11 (Tetrahedron, 2007, 63, 291). After the corresponding methanol was produced, it was produced according to the method described above.
  • (3,5-dichloropyridin-4-yl) methanamine was produced from the corresponding pyridinecarbaldehyde according to the method described in Patent Document 25 (WO2005 / 116209).
  • As other aminomethylpyridines commercially available products were used.
  • Step B 4- (azidomethyl) -2,6-di-tert-butylpyridine
  • Step C of the synthesis of 349 a methanamine compound was obtained by using the azide compound obtained in the above step in place of 4- (azidomethyl) -2-phenylpyridine.
  • Step D N-((2,6-di-tert-butylpyridin-4-yl) methyl) -4-iodobenzenesulfonamide
  • Step C of Synthesis 1 the sulfonamide compound was obtained by using the methanamine compound obtained in the above step instead of 4- (aminomethyl) quinoline.
  • Step E N-((2,6-di-tert-butylpyridin-4-yl) methyl) -4- (phenylethynyl) benzenesulfonamide
  • Step D of Synthesis 1 the sulfonamide compound obtained in the above step was used instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and phenylacetylene was used instead of trimethylsilylacetylene. 1, compound no. 360 was obtained.
  • Table 1 The compounds [I] synthesized as described above, their physical properties and NMR data are shown in Table 1 (Table 1-1 to Table 1-46).
  • Table 1 is a generic name (generic name) of Tables 1-1 to 1-46.
  • Example 2 [Formulation example] Formulation Example 1: Emulsion 10 parts of the compound of the present invention were dissolved in 45 parts of 1,2-dimethyl-4-ethylbenzene and 35 parts of 1-methyl-2-pyrrolidinone, and this was dissolved in Solpol 3005X (an interface manufactured by Toho Chemical Co., Ltd.). 10 parts of an activator (trade name) was added and mixed by stirring to obtain a 10% emulsion.
  • Formulation example 2 wettable powder 10 parts of the compound of the present invention was added to a mixture of 2 parts of sodium lauryl sulfate, 4 parts of sodium lignin sulfonate, 20 parts of white carbon and 64 parts of clay. % Wettable powder was obtained.
  • Formulation Example 3 Granules To 5 parts of the present compound, 2 parts of sodium dodecylbenzenesulfonate, 2 parts of carboxymethylcellulose, 2 parts of sodium lauryl sulfate, 10 parts of bentonite and 79 parts of clay were added and mixed thoroughly. An appropriate amount of water was added and the mixture was further stirred, granulated with a granulator, and dried by ventilation to obtain a 5% granule.
  • Formulation Example 4 Powder 1 part of the original compound is dissolved in 2 parts of soybean oil, 5 parts of white carbon, 0.3 part of isopropyl acid phosphate (PAP) and 91.7 parts of clay are added, and the mixture is stirred and mixed with a juice mixer. A 1% powder was obtained.
  • PAP isopropyl acid phosphate
  • Formulation Example 5 Flowable agent 20 parts of water containing 20 parts of the present compound, 2 parts, 1 part and 0.2 part of polyoxyethylene alkyl ether, sodium dialkylsulfosuccinate and 1,2-benzisothiazolin-3-one, respectively Were mixed with 60 parts of water containing 8 parts and 0.32 parts of propylene glycol and xanthan gum, respectively, to obtain a 20% suspension in water.
  • Formulation Example 6 Granule wettable powder 2 parts of sodium lauryl sulfate, 3 parts of sodium alkylnaphthalene sulfonate, 5 parts of dextrin, 20 parts of white carbon and 50 parts of clay were added to 20 parts of the compound of the present invention and mixed thoroughly. An appropriate amount of water was added, and the mixture was further stirred, granulated with a granulator, and dried by ventilation to obtain a 20% granular wettable powder.
  • Example 3 [Efficacy test] (1) Control effect test against tomato plague A potted tomato (variety; large-scale longevity, 5.5 leaf stage) is a chemical solution in which 10% wettable powder of each test compound is adjusted to 125 ppm (hereinafter referred to as a reagent solution). Sprayed with 15 ml per pot using a spray gun, sprayed with a zoospore suspension (Phytophthora infestans) zoospore suspension (sporemide concentration of 1.0 ⁇ 10 4 cells / ml) one day later, wet at 21 ° C. After standing for 1 day under room conditions and further in a greenhouse for 3 days to cause sufficient disease, the degree of disease on each leaf was examined, and the control value was calculated using the following formula.
  • a zoospore suspension Phytophthora infestans
  • zoospore suspension sporemide concentration of 1.0 ⁇ 10 4 cells / ml
  • Control value calculation; control value ⁇ (untreated disease area rate ⁇ treated drug disease rate) / untreated disease area rate ⁇ ⁇ 100
  • the calculated control value was determined according to the following criteria. The results are shown in Table 2.
  • novel compound of the present invention represented by the formula [I] exhibits an excellent control activity against pests such as pathogens, insects, mites, nematodes and the like that particularly affect agricultural and horticultural plants, it is extremely useful as a new agricultural chemical. It is.

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Abstract

A novel sulfonamide compound represented by this formula (I). This compound exhibits an excellent control activity against harmful organisms, specifically pathogenic bacteria, insects, mites, nematodes and the like which harm agricultural/horticultural plants; hence, the compound is extremely useful as a new agrochemical. R1, R2, R3, R4: H, COOR, etc. A: phenylene, etc. B: a) phenyl, etc., b) C1-6 straight-chain/branching alkyl, etc., c) SiR5R6R7, d) COOR, etc., e) H (R5, R6, R7: C1-6 straight-chain/branching alkyl, phenyl, R: C1-8 straight-chain/branching alkyl, benzyl, cyclic ether, etc.) (given a), b), B may be substituted with formyl, halogen, haloalkyl, cyano, nitro, etc.)

Description

農園芸用の有害生物防除剤としてのスルホンアミド誘導体Sulfonamide derivatives as pest control agents for agriculture and horticulture
　本発明は、有害生物防除剤、特に農園芸用有害生物防除剤として有用である新規なスルホンアミド誘導体に関するものである。 The present invention relates to a novel sulfonamide derivative that is useful as a pest control agent, particularly a pest control agent for agriculture and horticulture.
　特許文献１～２４及び非特許文献１～１１により、種々のスルホンアミド誘導体が、有害生物防除活性を有することが公知となっている。 From Patent Documents 1 to 24 and Non-Patent Documents 1 to 11, it is known that various sulfonamide derivatives have pest control activity.
　しかしながら近年、有害生物防除剤に対する薬剤抵抗性の発達によって、その薬剤効力の低下が由々しい問題となっている。このため、従来の有害生物防除活性を有するスルホンアミド化合物に代わる新たな化合物の開発が依然として必要とされている。本発明のスルホンアミド誘導体は、新規化合物であり、農園芸の有害生物防除活性を有することも知られていない。 However, in recent years, due to the development of drug resistance against pest control agents, a decrease in drug efficacy has become a serious problem. For this reason, there is still a need for the development of new compounds to replace conventional sulfonamide compounds having pest control activity. The sulfonamide derivative of the present invention is a novel compound and is not known to have agricultural and horticultural pest control activities.
ＷＯ２００６／０９７４８９号公報WO2006 / 097489 ＷＯ２００７／０９３５９９号公報WO2007 / 093599 ＷＯ２００８／０２２９３７号公報WO2008 / 022937 ＷＯ２００８／０６２０１１号公報WO2008 / 062011 Publication ＷＯ２００８／０６２０１２号公報WO2008 / 062012 Publication ＷＯ２００９／０７１４４８号公報WO2009 / 071448 ＷＯ２００９／１０１０７８号公報WO2009 / 101078 ＷＯ２００９／１０１０８２号公報WO2009 / 101082 publication ＷＯ２００９／１０３６５０号公報WO2009 / 103650 publication ＷＯ２００９／１１２５３３号公報WO2009 / 112533 ＷＯ２００９／１１２５２３号公報WO2009 / 112523 ＷＯ２００９／１２４９０３号公報WO2009 / 124903 Publication ＷＯ２００９／１４１２４１号公報WO2009 / 141241 ＷＯ２００９／１４１２７４号公報WO2009 / 141274 ＷＯ２００９／１４４１５９号公報WO2009 / 144159 ＵＳ２００４／８７７８９号公報US2004 / 87789 ＷＯ２００９／１１１８３０号公報WO2009 / 111830 publication ＷＯ２００８／２５５０９号公報WO 2008/25509 ＷＯ２００６／２９１５４号公報WO2006 / 29154 ＷＯ２００４／０７４２３８号公報WO2004 / 074238 ＷＯ２００５／８０３５０号公報WO2005 / 80350 Publication ＷＯ２００９／５７８２７号公報WO2009 / 57827 ＵＳ００５６６３３５７号公報US005663357 Publication ＷＯ２０１２／０４３７８号公報WO2012 / 04378 publication ＷＯ２０１０／１３２９９９号公報WO2010 / 132999 ＷＯ２００５／１１６００９号公報WO2005 / 116209 publication
　本発明の課題は、新規なスルホンアミド誘導体及びそれを有効成分とする農園芸用有害生物防除剤を提供することである。 An object of the present invention is to provide a novel sulfonamide derivative and an agricultural and horticultural pest control agent containing the derivative as an active ingredient.
　本発明者らは、前記の課題を解決するために鋭意検討した結果、新規化合物である種のスルホンアミド誘導体が顕著な農園芸の殺虫、殺ダニ、殺線虫及び殺菌活性を有する事を見出し、かかる知見に基づき本発明を完成した。 As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that a certain sulfonamide derivative as a novel compound has remarkable agricultural and horticultural insecticidal, acaricidal, nematicidal and bactericidal activities. Based on this finding, the present invention has been completed.
　即ち、本発明は次の通りである。 That is, the present invention is as follows.
　第１の発明は、次式［Ｉ］で示されるスルホンアミド誘導体に関するものである。 The first invention relates to a sulfonamide derivative represented by the following formula [I].
Figure JPOXMLDOC01-appb-C000005
 　［式中Ｒ１、Ｒ２、Ｒ３、Ｒ４は、各々水素原子、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８のシクロアルキル又は炭素原子数３～８のシクロアルケニルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シアノアルキル（１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）又は、Ｒ１とＲ２が結合してピリジン環上の炭素原子と共に形成するチオフェン環、ピリジン環、ピロール環、イミダゾール環、ベンゼン環、ナフタレン環、ピリミジン環、フラン環、ピラジン環、ピラゾール環、オキサゾール環を表し、
　Ａは、フェニレン、５若しくは６員環のヘテロアレンジイル（ヘテロアレンは１～３個のＮ、Ｏ、Ｓ原子を環に含み、また、フェニレン、ヘテロアレンジイルのいずれも、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、シアノアルキル（１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）から選択する１ないし４個の置換基で置換されていても良い）を表し、
　Ｂは
ａ）フェニル、ベンジル、オキサゾリル、イソオキサゾリル、フリル、ベンゾフリル、イソベンゾフリル、ジヒドロベンゾフリル、チアゾリル、イソチアゾリル、ナフチル、ピリミジニル、ピラジニル、キノキサリル、キナゾリル、ピリジル、キノリル、イソキノリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ピロリル、インドリル、イソインドリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、チエニル、ベンゾチエニル、イミダゾリル、ベンズイミダゾリル、ピラゾリル、ピリドニル、トリアジニル、トリアゾリル、チアジアゾリル、オキサジアゾリル、テトラゾリル、フェロセニルから成る群より選択される、０～３個のヘテロ原子を場合によっては含有する単環式もしくは二環式の環、
ｂ）炭素原子数１～６の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８のシクロアルキル又は炭素原子数３～８のシクロアルケニル、
ｃ）－ＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）、
ｄ）－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニル、ベンジルまたは環状エーテルである）、ハロゲン、ホルミル（－ＣＨＯ）またはカルボキシル（－ＣＯＯＨ）、
ｅ）水素原子
から選択され、ａ）、ｂ）の場合Ｂは－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、＝ＮＯＲ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８のシクロアルキル、炭素原子数３～８のシクロアルケニルまたは環状エーテルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、ハロアルキルチオ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキルチオ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６個の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シアノアルキル（１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）、オキソ（＝Ｏ）から選択する１ないし７個の置換基で置換されていても良い。］
Figure JPOXMLDOC01-appb-C000005
 [Wherein R 1 , R 2 , R 3 , R 4 are each a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R , —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, or linear or branched alkynyl having 2 to 8 carbon atoms. , cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms carbon atoms 3 ~ 8), - SiR 5 R 6 R 7, -OSi 5 R 6 R 7 (R 5 , R 6, R 7 linear or branched alkyl having 1 to 6 carbon atoms, two or all phenyl may be all be the same substituent is different substituents) Haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (same or different, 1 halogen atom A linear or branched alkenyl group having 2 to 6 carbon atoms substituted with ˜4, and a haloalkoxy (identical or different, the number of carbon atoms substituted with 1 to 9 halogen atoms is 1 1-4 linear or branched alkoxy groups), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO— 1 carbon atom substituted by an acyl group of To 3 linear or branched alkoxy groups), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— Straight chain or branched alkyl group having 1 to 3 carbon atoms substituted by 5 acyloxy groups), alkylsulfonylalkyl (1 to 5 straight chain or branched chain having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by an alkylsulfonyl group, or siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (R 5 , R 6 , R 7 Straight chain or branched alkyl or phenyl having 1 to 6 carbon atoms, two or all of which may be the same substituent or all different substituents). Chain or branched alkyl group), hydroxy Alkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted with 1 to 5 hydroxyl groups), alkoxyalkyl (a linear or branched 1 having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by -5 alkoxy groups, a haloalkoxyalkyl (identical or different, carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a linear or branched 1 to 5 haloalkoxy group having 1 to 4 carbon atoms, alkylthioalkyl (the number of carbon atoms is 1 to 8 linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 linear or branched alkylthio groups), dialkoxy acetal (having 1 to 3 carbon atoms) 8 linear or branched A dialkoxymethyl group in which two alkoxy groups are substituted with a methyl group), alkoxyalkoxy (1 to 8 carbon atoms substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) 3 linear or branched alkyl groups), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro , Amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (-CHO), carboxyl (-COOH) or a carbon atom on the pyridine ring by bonding R 1 and R 2 It represents a thiophene ring which together form a pyridine ring, a pyrrole ring, an imidazole ring, a benzene ring, a naphthalene ring, a pyrimidine ring, a furan ring, a pyrazine ring, a pyrazole ring, an oxazole ring,
A is phenylene, 5- or 6-membered heteroarrangeyl (heteroarene contains 1 to 3 N, O, and S atoms in the ring, and both phenylene and heteroarrangeyl are —C (O) OR , —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, — NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (wherein R is linear or branched alkyl having 1 to 8 carbon atoms, and having 2 to 8 carbon atoms) Linear or branched alkenyl, linear or branched alkynyl having 2 to 8 carbon atoms or carbon atom C 3-8 cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms of), - SiR 5 R 6 R 7, -OSiR 5 R 6 R 7 (R 5, R 6, R 7 C 1 -C 6 linear or branched alkyl, phenyl, two or all of which may be the same substituent or all different substituents, and haloalkyl (identical or different, substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 4 carbon atoms), a haloalkenyl (identical or different, linear or substituted with 2 to 6 carbon atoms substituted with 1 to 4 halogen atoms, or Branched alkenyl group), haloalkoxy (same or different, linear or branched alkoxy group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), acylalkoxy ((carbon Number of atoms A linear or branched aliphatic hydrocarbon group having 8 to 8 linear or branched alkoxy groups having 1 to 3 carbon atoms substituted by 1 to 5 acyl groups represented by —CO—. ), Acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— substituted with 1 to 5 acyloxy groups 1 to 3 linear or branched alkyl groups), alkylsulfonylalkyl (1 to 8 carbon atoms substituted by 1 to 5 linear or branched alkylsulfonyl groups having 1 to 8 carbon atoms) To 3 linear or branched alkyl groups), siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (R 5 , R 6 and R 7 are linear or 1 to 6 carbon atoms) Branched alkyl, phenyl, two or all have the same substituents 1 or 3 linear or branched alkyl groups substituted with 1 to 3 carbon atoms), hydroxyalkyl (1 to 5 carbon atoms substituted with 1 to 5 hydroxyl groups). 3 straight-chain or branched alkyl groups), alkoxyalkyl (straight or straight-chain 1 to 3 carbon atoms substituted with 1 to 5 straight-chain or branched alkoxy groups having 1 to 8 carbon atoms) Linear or branched alkyl group), haloalkoxyalkyl (same or different, linear or branched 1 to 5 halo having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by an alkoxy group), an alkylthioalkyl (a linear or branched alkyl group having 1 to 8 carbon atoms having 1 to 8 carbon atoms) Substituted carbon field A linear or branched alkyl group of 1 to 3), dialkoxy acetal (a dialkoxymethyl group in which a linear or branched alkoxy group having 1 to 8 carbon atoms is substituted with two methyl groups) , Alkoxyalkoxy (a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by a linear or branched alkoxy group having 1 to 8 carbon atoms), cyanoalkyl (C1-C3 linear or branched alkyl group substituted with 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl , Phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl Imides, represent formyl (-CHO), a carboxyl to 1 to choose from (-COOH) may be substituted with four substituents),
B is a) phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzoisothiazolyl , Pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl, ferrocenyl A monocyclic or bicyclic ring optionally containing 0 to 3 heteroatoms,
b) linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, Cycloalkyl having 3 to 8 carbon atoms or cycloalkenyl having 3 to 8 carbon atoms,
c) —SiR 5 R 6 R 7 (R 5 , R 6 , R 7 are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, and even if two or all are the same substituents, all Different substituents may be used),
d) —C (O) OR, —C (O) NHR, —C (O) NR 2 , —SO 2 NHR, —SO 2 NR 2 (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon having 3 to 8 carbon atoms C 3 -C 8 cycloalkenyl, benzyl or cyclic ether), halogen, formyl (—CHO) or carboxyl (—COOH),
e) selected from hydrogen atoms, and in the case of a) and b) B is —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, ═NOR, —SO 2 NHR, —SO 2 NR 2 (where R is linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, or linear or branched alkynyl having 2 to 8 carbon atoms. , A cycloalkyl having 3 to 8 carbon atoms, a cycloalkenyl having 3 to 8 carbon atoms or a cyclic ether), —SiR 5 R 6 R 7 , —OSiR 5 R 6 R 7 (R 5 , R 6 , R 7 linear or branched alkyl having 1 to 6 carbon atoms, phenyl, two or all having the same substituents, all May be different substituents), haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (identical or identical) Differently, a linear or branched alkenyl group having 2 to 6 carbon atoms substituted with 1 to 4 halogen atoms, haloalkoxy (identical or different, substituted with 1 to 9 halogen atoms) Straight-chain or branched alkoxy groups having 1 to 4 carbon atoms), haloalkylthio (the same or different, straight-chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Or branched alkyl Group), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO— the number of carbon atoms substituted by 1 to 5 acyl groups represented by —CO— 1 to 3 linear or branched alkoxy groups), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— A linear or branched alkyl group having 1 to 3 carbon atoms substituted with 5 acyloxy groups), an alkylsulfonylalkyl (a linear or branched 1 to 5 carbon atom having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted with 1 alkylsulfonyl group), siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (R 5 , R 6 , R 7 is a linear or branched alkyl having 1 to 6 carbon atoms, A linear or branched alkyl group having 1 to 3 carbon atoms substituted by phenyl, and two or all of them may be the same substituent or all different substituents), hydroxyalkyl (1 to 5 A linear or branched alkyl group having 1 to 3 carbon atoms substituted with a hydroxyl group of), alkoxyalkyl (a linear or branched alkoxy group having 1 to 8 carbon atoms having 1 to 5 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by haloalkoxyalkyl (identical or different, and having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) A straight or branched alkyl group having 1 to 3 carbon atoms substituted by a straight or branched 1 to 5 haloalkoxy group, alkylthioalkyl (straight chain having 1 to 8 carbon atoms) Or branched A linear or branched alkyl group having 1 to 3 carbon atoms substituted with 5 alkylthio groups), a dialkoxyacetal (a linear or branched alkoxy group having 1 to 8 carbon atoms). A dialkoxymethyl group substituted with 2 methyl groups), an alkoxyalkoxy (a straight chain having 1 to 8 carbon atoms and a straight or branched 1 to 5 carbon atom substituted with 1 to 3 carbon atoms). A linear or branched alkyl group having 1 to 3 carbon atoms substituted with 1 to 5 cyano groups), halogen, cyano, nitro, amino, Hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothia , Benzoxazolyl, Benzookisoriru, imide, formyl (-CHO), a carboxyl (-COOH), an oxo (= O) may be substituted with 1 to select to 7 substituents from. ]
　また、第２の発明は、式［Ｉ］で示されるスルホンアミド誘導体の製造方法である。 The second invention is a method for producing a sulfonamide derivative represented by the formula [I].
　さらに、第３の発明は、式［Ｉ］で示されるスルホンアミド誘導体を有効成分として１種または２種以上含む有害生物防除剤である。 Furthermore, the third invention is a pest control agent comprising one or more sulfonamide derivatives represented by the formula [I] as an active ingredient.
　式［Ｉ］で示される本発明の新規なスルホンアミド誘導体は、有害生物、特に、農園芸の有害生物に対し、優れた防除効果を有するものである。 The novel sulfonamide derivative of the present invention represented by the formula [I] has an excellent control effect against pests, particularly agricultural and horticultural pests.
　以下、本発明について詳細に説明する。 Hereinafter, the present invention will be described in detail.
　本発明における上記スルホンアミド誘導体には、式［Ｉ］で示されるスルホンアミド誘導体の他に、当該誘導体の塩（ナトリウム塩、カリウム塩、マグネシウム塩、カルシウム塩、アルミニウム塩など）、水和物、溶媒和物、結晶多形の物質、および式［Ｉ］で示されるスルホンアミド誘導体のＮ－オキシドも包含される。さらに本発明化合物に存在するすべての可能な立体異性体若しくは光学異性体、および２種類以上のその異性体を任意の比率で含む混合物も、本発明化合物（式［Ｉ］で示されるスルホンアミド誘導体）の範囲に含まれる。 In addition to the sulfonamide derivative represented by the formula [I], the sulfonamide derivative in the present invention includes a salt (sodium salt, potassium salt, magnesium salt, calcium salt, aluminum salt, etc.), hydrate, Also included are solvates, crystalline polymorphic substances, and N-oxides of sulfonamide derivatives of formula [I]. Furthermore, all possible stereoisomers or optical isomers present in the compound of the present invention, and a mixture containing two or more kinds of isomers in any ratio are also represented by the compound of the present invention (sulfonamide derivative represented by the formula [I]). ).
　前記の化合物［Ｉ］で表したＲ１、Ｒ２、Ｒ３、Ｒ４、Ａ、Ｂは、次の通りである。 R 1 , R 2 , R 3 , R 4 , A and B represented by the compound [I] are as follows.
　Ｒ１は、水素原子、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数3～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６個の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、シアノアルキル（１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）又は、Ｒ１とＲ２が結合してピリジン環上の炭素原子と共に形成するチオフェン環、ピリジン環、ピロール環、イミダゾール環、ベンゼン環、ナフタレン環、ピリミジン環、フラン環、ピラジン環、ピラゾール環、オキサゾール環を表す。 R 1 is a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, — C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon atom having 3 to 8 carbon atoms 3 to 8 cycloalkenyl), —SiR 5 R 6 R 7 , —OSiR 5 R 6 R 7 (R 5 , R 6 R 7 is linear or branched alkyl having 1 to 6 carbon atoms, phenyl, two or all of which may be the same or different, and haloalkyl (identical or different, halogen atoms A linear or branched alkyl group having 1 to 4 carbon atoms substituted by the number 1 to 9, a haloalkenyl (identical or different, and the number of carbon atoms substituted by 1 to 4 halogen atoms) Is a linear or branched alkenyl group having 2 to 6), haloalkoxy (same or different, linear or branched having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Alkoxy group), acylalkoxy ((straight-chain or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO— the number of carbon atoms substituted by 1 to 5 acyl groups represented by —CO— 1 to 3 linear or branched a COXY group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —carbon substituted by 1 to 5 acyloxy groups represented by —CO—O— Straight or branched alkyl group having 1 to 3 atoms), alkylsulfonylalkyl (carbon atom substituted with 1 to 5 straight or branched alkylsulfonyl group having 1 to 8 carbon atoms) A linear or branched alkyl group of 1 to 3), siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (R 5 , R 6 , R 7 are straight chain having 1 to 6 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by chain or branched alkyl or phenyl, and two or all of them may be the same substituent or all different substituents) , Hydroxyalkyl (1-5 hydrides) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a xyl group), an alkoxyalkyl (a linear or branched 1 to 5 alkoxy group having 1 to 8 carbon atoms) Substituted or straight chain or branched alkyl group having 1 to 3 carbon atoms), haloalkoxyalkyl (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted with a linear or branched haloalkoxy group having 1 to 5 carbon atoms, alkylthioalkyl (a straight chain having 1 to 8 carbon atoms) Or a linear or branched alkyl group having 1 to 3 carbon atoms substituted by a branched alkylthio group having 1 to 5 carbon atoms, dialkoxyacetal (linear or branched having 1 to 8 carbon atoms) -Like alkoxy group to methyl group Dialkoxymethyl group substituted), alkoxyalkoxy (linear or branched having 1 to 3 carbon atoms substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) -Like alkoxy group), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalo Sulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH) or R thiophene 1 and R 2 form together with the carbon atoms on the binding to the pyridine ring Represents a pyridine ring, a pyrrole ring, an imidazole ring, a benzene ring, a naphthalene ring, a pyrimidine ring, a furan ring, a pyrazine ring, a pyrazole ring, an oxazole ring.
　Ｒ２、Ｒ３、Ｒ４は、各々水素原子、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、シアノアルキル（１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）を表す。 R 2 , R 3 and R 4 are each a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, — C (O) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is the number of carbon atoms 1-8 linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or 3 to 3 carbon atoms 8 cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms), —SiR 5 R 6 R 7 , —OSiR 5 R 6 R 7 (R 5 , R 6 , R 7 linear or branched alkyl having 1 to 6 carbon atoms, phenyl, two or all of which may be the same or all different substituents), haloalkyl ( Linear or branched alkyl groups having 1 to 4 carbon atoms, which are the same or different and substituted with 1 to 9 halogen atoms, haloalkenyl (identical or different, and having 1 to 4 halogen atoms) Straight or branched alkenyl groups having 2 to 6 carbon atoms), haloalkoxy (identical or different, and having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Linear or branched alkoxy group), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO- 1-5 acyl groups Straight of 1 to 3 carbon atoms substituted by Or branched alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— represented by 1 to 5 acyloxy groups A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1) or alkylsulfonylalkyl (a linear or branched alkylsulfonyl group having 1 to 8 carbon atoms). A substituted or straight chain or branched alkyl group having 1 to 3 carbon atoms), siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (R 5 , R 6 and R 7 are each 1 carbon atom) 1-6 linear or branched alkyls or phenyls having from 1 to 6 carbon atoms substituted by 2 or all of which may be the same or different substituents. Alkyl group), hydroxyalkyl A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 hydroxyl groups), alkoxyalkyl (linear or branched 1 to 5 carbon atoms having 1 to 8 carbon atoms) Linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 alkoxy group), haloalkoxyalkyl (the same or different, the number of carbon atoms substituted with 1 to 9 halogen atoms is A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 4 straight or branched 1 to 5 haloalkoxy groups, alkylthioalkyl (having 1 to 3 carbon atoms) 8 linear or branched alkyl groups having 1 to 3 carbon atoms substituted with 1 to 5 linear or branched alkylthio groups), dialkoxyacetals (having 1 to 8 carbon atoms) Linear or branched alkoxy Is a dialkoxymethyl group having 2 substituted methyl groups), alkoxyalkoxy (1-3 carbon atoms substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) Linear or branched alkoxy group), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino , Hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (-CHO), carboxyl (- COOH).
　Ａは、フェニレン、５若しくは６員環のヘテロアレンジイル（ヘテロアレンは１－3個のＮ、Ｏ、Ｓ原子を環に含み、また、フェニレン、ヘテロアレンジイルのいずれも、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６個の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、シアノアルキル（１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）から選択する１ないし４個の置換基で置換されていても良い）を表す。 A is phenylene, 5- or 6-membered heteroarrangeyl (heteroarene contains 1 to 3 N, O, and S atoms in the ring, and both phenylene and heteroarrangeyl are —C (O) OR , —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, — NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (wherein R is linear or branched alkyl having 1 to 8 carbon atoms, and having 2 to 8 carbon atoms) Linear or branched alkenyl, linear or branched alkynyl having 2 to 8 carbon atoms, or carbon atom 3-8 cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms of), - SiR 5 R 6 R 7, -OSiR 5 R 6 R 7 (R 5, R 6, R 7 having 1 to 6 carbon atoms Linear or branched alkyl, phenyl, two or all of which may be the same or different, and haloalkyl (identical or different, substituted with 1 to 9 halogen atoms) Linear or branched alkyl group having 1 to 4 atoms), haloalkenyl (same or different, linear or branched having 2 to 6 carbon atoms substituted with 1 to 4 halogen atoms) Alkenyl group), haloalkoxy (same or different, linear or branched alkoxy group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), acylalkoxy ((carbon atoms Number is 1 A linear or branched aliphatic hydrocarbon group having 8 to 8 linear or branched alkoxy groups having 1 to 3 carbon atoms substituted by 1 to 5 acyl groups represented by —CO—. ), Acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— substituted with 1 to 5 acyloxy groups 1 to 3 linear or branched alkyl groups), alkylsulfonylalkyl (1 to 8 carbon atoms substituted by 1 to 5 linear or branched alkylsulfonyl groups having 1 to 8 carbon atoms) To 3 linear or branched alkyl groups), siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (where R 5 , R 6 and R 7 are linear with 1 to 6 carbon atoms) Or branched alkyl, phenyl, two or all substituted the same 1 or 3 linear or branched alkyl groups substituted with 1 to 3 carbon atoms), hydroxyalkyl (1 to 5 carbon atoms substituted with 1 to 5 hydroxyl groups). 3 straight-chain or branched alkyl groups), alkoxyalkyl (straight or straight-chain 1 to 3 carbon atoms substituted with 1 to 5 straight-chain or branched alkoxy groups having 1 to 8 carbon atoms) Chain or branched alkyl group), haloalkoxyalkyl (same or different, linear or branched 1 to 5 carbon atoms having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Straight chain or branched alkyl group having 1 to 3 carbon atoms substituted with a haloalkoxy group), alkylthioalkyl (straight chain or branched alkyl group having 1 to 8 carbon atoms) Carbon substituted by Straight-chain or branched alkyl group having 1 to 3 atoms), dialkoxyacetal (dialkoxymethyl group in which a straight-chain or branched alkoxy group having 1 to 8 carbon atoms is substituted with two methyl groups) ), Alkoxyalkoxy (a linear or branched alkoxy group having 1 to 3 carbon atoms substituted with a linear or branched alkoxy group having 1 to 8 carbon atoms), cyano Alkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, Phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxoly Represents imido, formyl (-CHO), a carboxyl to 1 to choose from (-COOH) may be substituted with 4 substituents).
　Ｂは、下記ａ）～ｅ）のいずれかから選択される。
ａ）フェニル、ベンジル、オキサゾリル、イソオキサゾリル、フリル、ベンゾフリル、イソベンゾフリル、ジヒドロベンゾフリル、チアゾリル、イソチアゾリル、ナフチル、ピリミジニル、ピラジニル、キノキサリル、キナゾリル、ピリジル、キノリル、イソキノリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ピロリル、インドリル、イソインドリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、チエニル、ベンゾチエニル、イミダゾリル、ベンズイミダゾリル、ピラゾリル、ピリドニル、トリアジニル、トリアゾリル、チアジアゾリル、オキサジアゾリル、テトラゾリル、フェロセニルから成る群より選択される、０～3個のヘテロ原子を場合によっては含有する単環式もしくは二環式の環。
ｂ）炭素原子数１～６の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８の直鎖状又は分岐状のシクロアルキルまたは炭素原子数３～８のシクロアルケニル。
ｃ）－ＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）。
ｄ）－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニル、ベンジルまたは環状エーテルである）、ハロゲン、ホルミル（－ＣＨＯ）またはカルボキシル（－ＣＯＯＨ）。
ｅ）水素原子。 B is selected from any of the following a) to e).
a) Phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzoisothiazolyl, pyrrolyl , Indolyl, isoindolyl, benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl, ferrocenyl, 0 Monocyclic or bicyclic rings optionally containing up to 3 heteroatoms.
b) linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, Linear or branched cycloalkyl having 3 to 8 carbon atoms or cycloalkenyl having 3 to 8 carbon atoms.
c) —SiR 5 R 6 R 7 (R 5 , R 6 , R 7 are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, and even if two or all are the same substituents, all May be different substituents).
d) —C (O) OR, —C (O) NHR, —C (O) NR 2 , —SO 2 NHR, —SO 2 NR 2 (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon having 3 to 8 carbon atoms C 3 -C 8 cycloalkenyl, benzyl or cyclic ether), halogen, formyl (—CHO) or carboxyl (—COOH).
e) A hydrogen atom.
　ａ）若しくはｂ）の場合、Ｂは、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、＝ＮＯＲ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数３～８のシクロアルキル、炭素原子数３～８のシクロアルケニルまたは環状エーテルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、ハロアルキルチオ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキルチオ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、シアノアルキル（シアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）、オキソ（＝Ｏ）から選択する１ないし７個の置換基で置換されていても良い。 In the case of a) or b), B represents —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O ) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, — NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, ═NOR, —SO 2 NHR, —SO 2 NR 2 (where R is the number of carbon atoms 1-8 linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or 3 to 3 carbon atoms 8 cycloalkyl, cycloalkenyl, or cyclic ethers having a carbon number of 3 ~ 8), - SiR 5 R 6 R 7, OSiR 5 R 6 R 7 (R 5, R 6, R 7 linear or branched alkyl having 1 to 6 carbon atoms, two or all phenyl may be all be the same substituent is different substituents ), Haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (identical or different, number of halogen atoms A linear or branched alkenyl group having 2 to 6 carbon atoms substituted with 1 to 4), haloalkoxy (identical or different, the number of carbon atoms substituted with 1 to 9 halogen atoms is 1 to 4 linear or branched alkoxy groups), haloalkylthio (same or different, linear or branched alkylthio having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Group), reed Straight chain having 1 to 3 carbon atoms substituted with 1 to 5 acyl groups represented by alkoxy ((straight-chain or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-) Chain or branched alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O- 1-5 acyloxy A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a group), an alkylsulfonylalkyl (a linear or branched alkyl group having 1 to 8 carbon atoms having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1), siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (where R 5 , R 6 , R 7 are the number of carbon atoms) 1 to 6 linear or branched alkyl, phenyl, A linear or branched alkyl group having 1 to 3 carbon atoms substituted by two or all of the same substituents or all different substituents), hydroxyalkyl (by 1 to 5 hydroxyl groups) Substituted with a linear or branched alkyl group having 1 to 3 carbon atoms) or alkoxyalkyl (substituted with a linear or branched alkoxy group having 1 to 8 carbon atoms) Linear or branched alkyl group having 1 to 3 carbon atoms), haloalkoxyalkyl (same or different, linear or substituted with 1 to 9 halogen atoms or 1 to 4 carbon atoms) A straight or branched alkyl group having 1 to 3 carbon atoms substituted by a branched 1 to 5 haloalkoxy group), alkylthioalkyl (straight or branched chain having 1 to 8 carbon atoms) 1-5 Archi Straight-chain or branched alkyl group having 1 to 3 carbon atoms substituted by a thio group), dialkoxyacetal (a straight-chain or branched alkoxy group having 1 to 8 carbon atoms is substituted with 2 methyl groups) Dialkoxymethyl group substituted), alkoxyalkoxy (linear or branched having 1 to 3 carbon atoms substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) -Like alkoxy group), cyanoalkyl (C1-C3 linear or branched alkyl group substituted by cyano group), halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyl Oxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl , Benzookisoriru, imide, formyl (-CHO), a carboxyl (-COOH), an oxo (= O) may be substituted with 1 to select to 7 substituents from.
　Ｒ１としては、水素原子、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、シアノアルキル（１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）を挙げることができるが、水素原子、アルキル（例えば、メチル基、エチル基、ｎ－プロピル基、イソプロピル基）、アルコキシ（例えば、メトキシ基、エトキシ基、ｎ－プロポキシ基、イソプロポキシ基）、ハロゲン（例えば、フッ素原子、塩素原子、臭素原子）、シアノ、ハロアルキル（例えば、モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、ヘプタフルオロイソプロピル基）、シアノアルキル（例えば、シアノメチル基、シアノエチル基）、ハロアルコキシ（例えば、モノフルオロメトキシ基、ジフルオロメトキシ基、トリフルオロメトキシ基）が好ましい。 R 1 includes a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O ) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon having 3 to 8 carbon atoms A cycloalkenyl having 3 to 8 atoms), —SiR 5 R 6 R 7 , —OSiR 5 R 6 R 7 (R 5 , R 6 and R 7 are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, two or all of which may be the same or different, and haloalkyl (identical or different) A linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms, or a haloalkenyl (identical or different, substituted with 1 to 4 halogen atoms) Straight chain or branched alkenyl group having 2 to 6 carbon atoms), haloalkoxy (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms or Branched alkoxy group), acylalkoxy ((straight-chain or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) substituted with 1 to 5 acyl groups represented by —CO—. Linear or branched with 1 to 3 carbon atoms Substituted with 1 to 5 acyloxy groups represented by —CO—O— (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms). Substituted with a linear or branched alkyl group having 1 to 3 carbon atoms) or alkylsulfonylalkyl (a linear or branched alkylsulfonyl group having 1 to 8 carbon atoms). A linear or branched alkyl group having 1 to 3 carbon atoms), siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (wherein R 5 , R 6 and R 7 have 1 to 6 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by linear or branched alkyl or phenyl, and two or all of them may be the same substituent or all different substituents) ), Hydroxyalkyl (1-5) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a hydroxyl group), an alkoxyalkyl (a linear or branched 1 to 5 alkoxy group having 1 to 8 carbon atoms) Substituted or straight chain or branched alkyl group having 1 to 3 carbon atoms), haloalkoxyalkyl (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted with a linear or branched haloalkoxy group having 1 to 5 carbon atoms, alkylthioalkyl (a straight chain having 1 to 8 carbon atoms) Or a linear or branched alkyl group having 1 to 3 carbon atoms substituted by a branched alkylthio group having 1 to 5 carbon atoms, dialkoxyacetal (linear or branched having 1 to 8 carbon atoms) -Like alkoxy group is methyl A dialkoxymethyl group substituted by 2 groups), alkoxyalkoxy (a straight chain having 1 to 3 carbon atoms substituted by a linear or branched 1 to 5 alkoxy group having 1 to 8 carbon atoms) Or branched alkoxy group), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy , Pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH) A hydrogen atom, alkyl (for example, methyl group, ethyl , N-propyl group, isopropyl group), alkoxy (for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group), halogen (for example, fluorine atom, chlorine atom, bromine atom), cyano, haloalkyl (for example, Monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), cyanoalkyl (for example, cyanomethyl group, cyanoethyl group), haloalkoxy (for example, monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group) ) Is preferred.
　Ｒ１がＲ２と結合してピリジン環上の炭素原子と共に形成する環としては、チオフェン環、ピリジン環、ピロール環、イミダゾール環、ベンゼン環、ナフタレン環、ピリミジン環、フラン環、ピラジン環、ピラゾール環、オキサゾール環を挙げることができるが、ベンゼン環が好ましい。 Examples of the ring R 1 to form together with the carbon atoms on the pyridine ring bonded to R 2, thiophene ring, pyridine ring, pyrrole ring, an imidazole ring, a benzene ring, a naphthalene ring, a pyrimidine ring, a furan ring, a pyrazine ring, a pyrazole Although a ring and an oxazole ring can be mentioned, a benzene ring is preferable.
　Ｒ２、Ｒ３、Ｒ４としては、各々水素原子、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シアノアルキル（１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）を挙げることができるが、水素原子、アルキル（例えば、メチル基、エチル基、ｎ－プロピル基、イソプロピル基）、アルコキシ（例えば、メトキシ基、エトキシ基、ｎ－プロポキシ基、イソプロポキシ基）、ハロゲン（例えば、フッ素原子、塩素原子、臭素原子）、シアノ、ハロアルキル（例えば、モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、ヘプタフルオロイソプロピル基）、シアノアルキル（例えば、シアノメチル基、シアノエチル基）、ハロアルコキシ（例えば、モノフルオロメトキシ基、ジフルオロメトキシ基、トリフルオロメトキシ基）が好ましい。 R 2 , R 3 and R 4 are each a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O ) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is a carbon atom) Linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or 3 carbon atoms ~ 8 cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms of), - SiR 5 R 6 R 7, -OSiR R 6 R 7 (R 5, R 6, R 7 linear or branched alkyl having 1 to 6 carbon atoms, two or all phenyl may be all be the same substituent is different substituents), Haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (same or different, halogen atoms having 1 to 4 carbon atoms) A linear or branched alkenyl group having 2 to 6 carbon atoms substituted with 4, haloalkoxy (identical or different, and having 1 to 9 carbon atoms substituted with 1 to 9 halogen atoms). 4 linear or branched alkoxy group), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO— 1 to carbon atoms substituted with acyl group Linear or branched alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— A linear or branched alkyl group having 1 to 3 carbon atoms substituted with an acyloxy group of the above, alkylsulfonylalkyl (a linear or branched alkyl group having 1 to 8 carbon atoms having 1 to 5 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a sulfonyl group), siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (R 5 , R 6 , R 7 are carbon atoms) Straight or branched alkyl or phenyl having 1 to 6 atoms, phenyl, two or all of which may be the same substituent or all different substituents) Or branched alkyl group), hydroxya Kill (linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 hydroxyl groups), alkoxyalkyl (linear or branched 1 having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by -5 alkoxy groups, a haloalkoxyalkyl (identical or different, carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a linear or branched 1 to 5 haloalkoxy group having 1 to 4 carbon atoms, alkylthioalkyl (the number of carbon atoms is 1 to 8 linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 linear or branched alkylthio groups), dialkoxy acetal (having 1 to 3 carbon atoms) 8 linear or branched a A dialkoxymethyl group in which a coxy group is substituted with 2 methyl groups), alkoxyalkoxy (1 to 8 carbon atoms substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) 3 linear or branched alkyl groups), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro , Amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (-CHO), carboxyl (—COOH) can be mentioned, but a hydrogen atom, alkyl (for example, Til, ethyl, n-propyl, isopropyl), alkoxy (eg, methoxy, ethoxy, n-propoxy, isopropoxy), halogen (eg, fluorine, chlorine, bromine), cyano Haloalkyl (for example, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), cyanoalkyl (for example, cyanomethyl group, cyanoethyl group), haloalkoxy (for example, monofluoromethoxy group, difluoromethoxy group) And a trifluoromethoxy group) are preferred.
　Ａはフェニレンを表し、置換基としては、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６個の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シアノアルキル（１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）から選択する１ないし４個の置換基で置換されていても良く、無置換、又はアルキル（例えば、メチル基、エチル基、ｎ－プロピル基、イソプロピル基）、アルコキシ（例えば、メトキシ基、エトキシ基、ｎ－プロポキシ基、イソプロポキシ基）、ハロゲン（例えば、フッ素原子、塩素原子、臭素原子）、シアノ、ハロアルキル（例えば、モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、ヘプタフルオロイソプロピル基）、ハロアルコキシ（例えば、モノフルオロメトキシ基、ジフルオロメトキシ基、トリフルオロメトキシ基）、ベンジルオキシ基、フェノキシ基が１ないし４個置換されていることが好ましい。 A represents phenylene, and substituents include —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O ) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, — NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (wherein R is 1 to 8 carbon atoms) Linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cyclocarbon having 3 to 8 carbon atoms. alkyl or cycloalkenyl carbon atoms 3 ~ 8), - SiR 5 R 6 R 7, -OSiR 5 R R 7 (R 5, R 6 , R 7 linear or branched alkyl having 1 to 6 carbon atoms, two or all phenyl may be all be the same substituent is different substituents), haloalkyl ( Linear or branched alkyl groups having 1 to 4 carbon atoms, which are the same or different and substituted with 1 to 9 halogen atoms, haloalkenyl (identical or different, and having 1 to 4 halogen atoms) Straight or branched alkenyl groups having 2 to 6 carbon atoms), haloalkoxy (identical or different, and having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Linear or branched alkoxy group), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO- 1-5 acyl groups Straight of 1 to 3 carbon atoms substituted by Or branched alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— represented by 1 to 5 acyloxy groups A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1) or alkylsulfonylalkyl (a linear or branched alkylsulfonyl group having 1 to 8 carbon atoms). A substituted or straight chain or branched alkyl group having 1 to 3 carbon atoms), siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (R 5 , R 6 and R 7 are each 1 carbon atom) Straight chain or branched chain having 1 to 3 carbon atoms substituted by up to 6 linear or branched alkyls, phenyls, two or all of which may be the same or different. Alkyl group), hydroxyalkyl (Linear or branched alkyl group having 1 to 3 carbon atoms substituted with 1 to 5 hydroxyl groups), alkoxyalkyl (linear or branched 1 having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by -5 alkoxy groups, a haloalkoxyalkyl (identical or different, carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a linear or branched 1 to 5 haloalkoxy group having 1 to 4 carbon atoms, alkylthioalkyl (the number of carbon atoms is 1 to 8 linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 linear or branched alkylthio groups), dialkoxy acetal (having 1 to 3 carbon atoms) 8 linear or branched alco A dialkoxymethyl group in which the methyl group is substituted with 2 methyl groups), alkoxyalkoxy (1 to 8 carbon atoms substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) 3 linear or branched alkyl groups), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro , Amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (-CHO), carboxyl Optionally substituted with 1 to 4 substituents selected from (—COOH), Substituted or alkyl (for example, methyl group, ethyl group, n-propyl group, isopropyl group), alkoxy (for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group), halogen (for example, fluorine atom, chlorine) Atom, bromine atom), cyano, haloalkyl (for example, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), haloalkoxy (for example, monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group) ), 1 to 4 benzyloxy groups and phenoxy groups are preferably substituted.
　Ａにおける５若しくは６員環のヘテロアレンジイル（ヘテロアレンは１～３個のＮ、Ｏ、Ｓ原子を環に含む）としては、オキサゾールジイル、イソキサゾールジイル、フランジイル、チアゾールジイル、イソチアゾールジイル、ピリミジンジイル、ピラジンジイル、ピリジンジイル、ピロールジイル、チオフェンジイル、イミダゾールジイル、ピラゾールジイルを挙げることができるが、オキサゾールジイル、チアゾールジイル、ピリジンジイル、チオフェンジイルが好ましい。また、置換基としては、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、シアノアルキル（１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）から選択する１ないし３個の置換基で置換されていても良く、無置換、又はアルキル（例えば、メチル基、エチル基、ｎ－プロピル基、イソプロピル基）、アルコキシ（例えば、メトキシ基、エトキシ基、ｎ－プロポキシ基、イソプロポキシ基）、ハロゲン（例えば、フッ素原子、塩素原子、臭素原子）、シアノ、ハロアルキル（例えば、モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、ヘプタフルオロイソプロピル基）、ハロアルコキシ（例えば、モノフルオロメトキシ基、ジフルオロメトキシ基、トリフルオロメトキシ基）、ベンジルオキシ基、フェノキシ基が１ないし３個置換されていることが好ましい。 5- or 6-membered heteroarylene diyl in A (heteroalene contains 1 to 3 N, O, S atoms in the ring) includes oxazolediyl, isoxazolediyl, furandyl, thiazolediyl, isothiazolediyl , Pyrimidinediyl, pyrazinediyl, pyridinediyl, pyrrolediyl, thiophenediyl, imidazolediyl, and pyrazolediyl, and oxazolediyl, thiazolediyl, pyridinediyl, and thiophenediyl are preferable. In addition, examples of the substituent include —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, — C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon atom having 3 to 8 carbon atoms 3) to 8), —SiR 5 R 6 R 7 , —OSiR 5 R 6 R 7 (R 5 , R 6 , R 7 linear or branched alkyl having 1 to 6 carbon atoms, phenyl, two or all of which may be the same or different, and haloalkyl (identical or different, halogen Straight or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 atoms, haloalkenyl (identical or different, carbon atoms substituted with 1 to 4 halogen atoms) Linear or branched alkenyl group having 2 to 6 carbon atoms), haloalkoxy (identical or different, linear or branched carbon atoms having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Alkoxy group), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO— substituted with 1 to 5 acyl groups represented by —CO— 1 to 3 linear or branched Alkoxy group), acyloxyalkyl ((straight-chain or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -carbon substituted with 1 to 5 acyloxy groups represented by -CO-O- Straight or branched alkyl group having 1 to 3 atoms), alkylsulfonylalkyl (carbon atom substituted with 1 to 5 straight or branched alkylsulfonyl group having 1 to 8 carbon atoms) A linear or branched alkyl group of 1 to 3), siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (where R 5 , R 6 and R 7 are linear chains of 1 to 6 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms, which is substituted by a linear or branched alkyl, phenyl, and two or all of them may be the same substituent or all different substituents), Hydroxyalkyl (1-5 hydrides A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a roxyl group), an alkoxyalkyl (a linear or branched alkoxy group having 1 to 8 carbon atoms or 1 to 5 carbon atoms) Substituted or straight chain or branched alkyl group having 1 to 3 carbon atoms), haloalkoxyalkyl (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted with a linear or branched haloalkoxy group having 1 to 5 carbon atoms, alkylthioalkyl (a straight chain having 1 to 8 carbon atoms) Or a linear or branched alkyl group having 1 to 3 carbon atoms substituted by a branched alkylthio group having 1 to 5 carbon atoms, dialkoxyacetal (linear or branched having 1 to 8 carbon atoms) -Like alkoxy group to methyl group Dialkoxymethyl group substituted), alkoxyalkoxy (linear or branched having 1 to 3 carbon atoms substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) -Like alkoxy group), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalo Select from sulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH) Optionally substituted with 1 to 3 substituents, unsubstituted or (Eg, methyl, ethyl, n-propyl, isopropyl), alkoxy (eg, methoxy, ethoxy, n-propoxy, isopropoxy), halogen (eg, fluorine, chlorine, bromine) Atom), cyano, haloalkyl (for example, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), haloalkoxy (for example, monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group), benzyl It is preferable that 1 to 3 oxy groups and phenoxy groups are substituted.
　Ｂにおける０～３個のヘテロ原子を場合によっては含有する単環式、もしくは二環式の環としては、フェニル、ベンジル、オキサゾリル、イソオキサゾリル、フリル、ベンゾフリル、イソベンゾフリル、ジヒドロベンゾフリル、チアゾリル、イソチアゾリル、ナフチル、ピリミジニル、ピラジニル、キノキサリル、キナゾリル、ピリジル、キノリル、イソキノリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ピロリル、インドリル、イソインドリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、チエニル、ベンゾチエニル、イミダゾリル、ベンズイミダゾリル、ピラゾリル、ピリドニル、トリアジニル、トリアゾリル、チアジアゾリル、オキサジアゾリル、テトラゾリル、フェロセニルを挙げることができるが、フェニル、オキサゾリル、イソオキサゾリル、フリル、チアゾリル、イソチアゾリル、ピリミジニル、ピラジニル、ピリジル、ピロリル、チエニル、イミダゾリル、ピラゾリルが好ましく、更にはフェニル、フリル、チアゾリル、ピリジル、チエニルが好ましい。また、置換基としては、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、＝ＮＯＲ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数３～８のシクロアルキル、炭素原子数３～８のシクロアルケニルまたは環状エーテルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、ハロアルキルチオ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキルチオ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６個の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、シアノアルキル（１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）、オキソ（＝Ｏ）から選択する１ないし７個の置換基で置換されていても良く、無置換、又はアルキル（例えば、メチル基、エチル基、ｎ－プロピル基、イソプロピル基）、アルコキシ（例えば、メトキシ基、エトキシ基、ｎ－プロポキシ基、イソプロポキシ基）、ハロゲン（例えば、フッ素原子、塩素原子、臭素原子）、シアノ、ハロアルキル（例えば、モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、ヘプタフルオロイソプロピル基）、ベンジルオキシ基、フェノキシ基が１ないし７個置換されていることが好ましい。 Monocyclic or bicyclic rings optionally containing 0 to 3 heteroatoms in B include phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, Isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzisothiazolyl, pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, benz Examples include imidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl, ferrocenyl, phenyl, oxazolyl , Isoxazolyl, furyl, thiazolyl, isothiazolyl, pyrimidinyl, pyrazinyl, pyridyl, pyrrolyl, thienyl, imidazolyl, pyrazolyl are preferred, further phenyl, furyl, thiazolyl, pyridyl, thienyl are preferred. In addition, examples of the substituent include —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, — C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, -N (OR) C ( O) OR, -NHSO 2 R, -NRSO 2 R, = NOR, -SO 2 NHR, R in -SO 2 NR 2 (wherein, of 1 to 8 carbon atoms Linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms , cycloalkenyl, or cyclic ethers having a carbon number of 3 ~ 8), - SiR 5 R 6 R 7, -OSi 5 R 6 R 7 (R 5 , R 6, R 7 linear or branched alkyl having 1 to 6 carbon atoms, two or all phenyl may be all be the same substituent is different substituents) Haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (same or different, 1 halogen atom A linear or branched alkenyl group having 2 to 6 carbon atoms substituted with ˜4, and a haloalkoxy (identical or different, the number of carbon atoms substituted with 1 to 9 halogen atoms is 1 Linear or branched alkoxy group having 4 to 4 carbon atoms, haloalkylthio (same or different, linear or branched alkylthio group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) ), Acylarco A straight chain having 1 to 3 carbon atoms substituted by 1 to 5 acyl groups represented by cis ((a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-) Chain or branched alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O- 1-5 acyloxy A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a group), an alkylsulfonylalkyl (a linear or branched alkyl group having 1 to 8 carbon atoms having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1), siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (where R 5 , R 6 , R 7 are the number of carbon atoms) 1-6 linear or branched alkyl, phenyl, 2 Or a linear or branched alkyl group having 1 to 3 carbon atoms, all substituted with the same substituent or all different substituents), hydroxyalkyl (substituted with 1 to 5 hydroxyl groups) Carbon having 1 to 3 carbon atoms or a linear or branched alkyl group having 1 to 3 carbon atoms, alkoxyalkyl (carbon having 1 to 8 carbon atoms having 1 to 8 linear or branched alkoxy groups) Linear or branched alkyl group having 1 to 3 atoms), haloalkoxyalkyl (same or different, linear or branched having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Straight chain or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 haloalkoxy groups having a shape, alkylthioalkyl (straight chain or branched chain having 1 to 8 carbon atoms) 1-5 alkylthio 1- to 3-carbon linear or branched alkyl group substituted by 1), dialkoxy acetal (1-8 linear or branched alkoxy group substituted with 2 methyl groups) Dialkoxymethyl group), alkoxyalkoxy (straight-chain or branched chain having 1 to 3 carbon atoms substituted with 1 to 5 straight-chain or branched alkoxy group having 1 to 8 carbon atoms) Alkoxy group), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, Benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxa Optionally substituted with 1 to 7 substituents selected from ryl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH), oxo (═O), unsubstituted, or alkyl (eg, methyl Group, ethyl group, n-propyl group, isopropyl group), alkoxy (for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group), halogen (for example, fluorine atom, chlorine atom, bromine atom), cyano, It is preferable that 1 to 7 haloalkyl groups (for example, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), benzyloxy group, and phenoxy group are substituted.
　Ｂにおける炭素原子数１～６の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８の直鎖状又は分岐状のシクロアルキルまたは炭素原子数３～８のシクロアルケニルとしては、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基、ビニル基、１－プロペニル基、２－プロペニル基、イソプロペニル基、エチニル基、プロパルギル基、シクロプロピル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロペンテニル基、シクロヘキセニル基を挙げることができるが、メチル基、エチル基、ｎ－プロピル基、ビニル基、シクロプロピル基、シクロペンチル基、シクロヘキシル基が好ましい。また、置換基としては、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、＝ＮＯＲ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数３～８のシクロアルキル、炭素原子数３～８のシクロアルケニルまたは環状エーテルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルコキシ基）、ハロアルキルチオ（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキルチオ基）、アシルアルコキシ（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－で表される１～５個のアシルオキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１～５個の－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６個の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状の１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１～８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１～８の直鎖状又は分岐状の１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基）、シアノアルキル（１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）、オキソ（＝Ｏ）から選択する１ないし７個の置換基で置換されても良くを挙げることができるが、無置換、又はアルキル（例えば、メチル基、エチル基、ｎ－プロピル基、イソプロピル基）、アルコキシ（例えば、メトキシ基、エトキシ基、ｎ－プロポキシ基、イソプロポキシ基）、ハロゲン（例えば、フッ素原子、塩素原子、臭素原子）、シアノ、ハロアルキル（例えば、モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、ヘプタフルオロイソプロピル基）、ベンジルオキシ基、フェノキシ基が１ないし７個置換されていることが好ましい。 Linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, Examples of straight-chain or branched cycloalkyl having 3 to 8 carbon atoms or cycloalkenyl having 3 to 8 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s- Butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, vinyl, 1-propenyl, 2-propenyl, isopropenyl, ethynyl, propargyl, cyclopropyl , Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclopentenyl group, and cyclohexenyl group. Le group, n- propyl group, a vinyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group is preferred. In addition, examples of the substituent include —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, — C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, -N (OR) C ( O) OR, -NHSO 2 R, -NRSO 2 R, = NOR, -SO 2 NHR, R in -SO 2 NR 2 (wherein, of 1 to 8 carbon atoms Linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms , cycloalkenyl, or cyclic ethers having a carbon number of 3 ~ 8), - SiR 5 R 6 R 7, -OSi 5 R 6 R 7 (R 5 , R 6, R 7 linear or branched alkyl having 1 to 6 carbon atoms, two or all phenyl may be all be the same substituent is different substituents) Haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (same or different, 1 halogen atom A linear or branched alkenyl group having 2 to 6 carbon atoms substituted with ˜4, and a haloalkoxy (identical or different, the number of carbon atoms substituted with 1 to 9 halogen atoms is 1 Linear or branched alkoxy group having 4 to 4 carbon atoms, haloalkylthio (same or different, linear or branched alkylthio group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) ), Acylarco A straight chain having 1 to 3 carbon atoms substituted by 1 to 5 acyl groups represented by cis ((a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-) Chain or branched alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O- 1-5 acyloxy A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a group), an alkylsulfonylalkyl (a linear or branched alkyl group having 1 to 8 carbon atoms having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1), siloxyalkyl (1 to 5 —OSiR 5 R 6 R 7 (where R 5 , R 6 , R 7 are the number of carbon atoms) 1-6 linear or branched alkyl, phenyl, 2 Or a linear or branched alkyl group having 1 to 3 carbon atoms, all substituted with the same substituent or all different substituents), hydroxyalkyl (substituted with 1 to 5 hydroxyl groups) Carbon having 1 to 3 carbon atoms or a linear or branched alkyl group having 1 to 3 carbon atoms, alkoxyalkyl (carbon having 1 to 8 carbon atoms having 1 to 8 linear or branched alkoxy groups) Linear or branched alkyl group having 1 to 3 atoms), haloalkoxyalkyl (same or different, linear or branched having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Straight chain or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 haloalkoxy groups having a shape, alkylthioalkyl (straight chain or branched chain having 1 to 8 carbon atoms) 1-5 alkylthio 1- to 3-carbon linear or branched alkyl group substituted by 1), dialkoxy acetal (1-8 linear or branched alkoxy group substituted with 2 methyl groups) Dialkoxymethyl group), alkoxyalkoxy (straight-chain or branched chain having 1 to 3 carbon atoms substituted with 1 to 5 straight-chain or branched alkoxy group having 1 to 8 carbon atoms) Alkoxy group), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, Benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxa And may be substituted with 1 to 7 substituents selected from ryl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH), and oxo (═O). Alkyl (eg, methyl, ethyl, n-propyl, isopropyl), alkoxy (eg, methoxy, ethoxy, n-propoxy, isopropoxy), halogen (eg, fluorine, chlorine, bromine) It is preferable that 1 to 7 atoms, cyano, haloalkyl (for example, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), benzyloxy group, and phenoxy group are substituted.
　Ｂにおける－ＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）としては、トリメチルシリル基、トリエチルシリル基、トリイソプロピルシリル基、ｔ－ブチルジメチルシリル基、ｔ－ブチルジフェニルシリル基を挙げることができるが、トリメチルシリル基、トリエチルシリル基が好ましい。 —SiR 5 R 6 R 7 (R 5 , R 6 , R 7 in B is linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and even if two or all are the same substituents, Examples of different substituents include a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a t-butyldimethylsilyl group, and a t-butyldiphenylsilyl group, with a trimethylsilyl group and a triethylsilyl group being preferred.
　Ｂとしては、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニル、ベンジルまたは環状エーテルである）、ハロゲン、ホルミル（－ＣＨＯ）またはカルボキシル（－ＣＯＯＨ）を挙げることができる。 As B, —C (O) OR, —C (O) NHR, —C (O) NR 2 , —SO 2 NHR, —SO 2 NR 2 (where R is a carbon atom having 1 to 8 carbon atoms) Linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms Or cycloalkenyl, benzyl or cyclic ether having 3 to 8 carbon atoms), halogen, formyl (—CHO) or carboxyl (—COOH).
　本願発明において、「アルキル」という用語は、炭素原子数が１～８の直鎖状又は分岐状のアルキル基を示し、例えばメチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基，ｓ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基、ｎ－ヘプチル基、又はｎ－オクチル基等を挙げることができる。 In the present invention, the term “alkyl” refers to a linear or branched alkyl group having 1 to 8 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group. And isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, and n-octyl groups.
　本願発明において、「アルケニル」という用語は、炭素原子数が２～８の直鎖状又は分岐状のアルケニル基を示し、例えばエテニル基、１－プロペニル基、２－プロペニル基、イソプロペニル基、１－ブテニル基、２－ブテニル基、又は３－ブテニル基等を挙げることができる。 In the present invention, the term “alkenyl” refers to a linear or branched alkenyl group having 2 to 8 carbon atoms, such as an ethenyl group, a 1-propenyl group, a 2-propenyl group, an isopropenyl group, 1 -Butenyl group, 2-butenyl group, 3-butenyl group and the like can be mentioned.
　本願発明において、「アルキニル」という用語は、炭素原子数が２～８の直鎖状又は分岐状のアルキニル基を示し、例えば、エチニル基、２－プロピニル基、２－ブチニル基、又は３－ブチニル基等を挙げることができる。 In the present invention, the term “alkynyl” refers to a linear or branched alkynyl group having 2 to 8 carbon atoms, for example, ethynyl group, 2-propynyl group, 2-butynyl group, or 3-butynyl group. Groups and the like.
　本願発明において、「シクロアルキル」という用語は、炭素原子数が３～８のシクロアルキル基を示し、例えばシクロプロピル基、シクロブチル基、シクロペンチル基、又はシクロヘキシル基を挙げることができる。 In the present invention, the term “cycloalkyl” refers to a cycloalkyl group having 3 to 8 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
　本願発明において、「シクロアルケニル」という用語は、炭素原子数が３～８のシクロアルケニル基を示し、例えば、１－シクロペンチル基、２－シクロペンチル基、３－シクロペンチル基、１－シクロヘキシル基、２－シクロヘキシル基、又は３－シクロヘキシル基を挙げることができる。 In the present invention, the term “cycloalkenyl” refers to a cycloalkenyl group having 3 to 8 carbon atoms, such as a 1-cyclopentyl group, 2-cyclopentyl group, 3-cyclopentyl group, 1-cyclohexyl group, 2- A cyclohexyl group or a 3-cyclohexyl group can be mentioned.
　本願発明において、「ヘテロ原子」という用語は、窒素原子、酸素原子、硫黄原子及びケイ素原子を包含する。 In the present invention, the term “heteroatom” includes a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom.
　本願発明において、「ハロゲン」という用語は、フッ素、塩素、臭素及びヨウ素を包含する。 In the present invention, the term “halogen” includes fluorine, chlorine, bromine and iodine.
　本願発明において、「ハロ・・・」（例えば、「ハロアルキル」）における「ハロ」という用語は、フッ素、塩素、臭素及びヨウ素を包含する。 In the present invention, the term “halo” in “halo...” (For example, “haloalkyl”) includes fluorine, chlorine, bromine and iodine.
　本願発明において、「ハロアルキル」という用語は、同一又は異なって、ハロゲン原子数１～９で置換されている炭素原子数が１～４の直鎖状又は分岐状のアルキル基を示し、例えば、モノフルオロメチル基、モノクロロメチル基、モノブロモメチル基、ジフルオロメチル基、トリフルオロメチル基、ペンタフルオロエチル基、ｎ－ヘプタフルオロプロピル基、又はイソヘプタフルオロプロピル基等を挙げることができる。 In the present invention, the term “haloalkyl” is the same or different and represents a linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms. Examples thereof include a fluoromethyl group, a monochloromethyl group, a monobromomethyl group, a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, an n-heptafluoropropyl group, and an isoheptafluoropropyl group.
　本願発明において、「ハロアルケニル」という用語は、同一又は異なって、ハロゲン原子数１～４で置換されている炭素原子数が２～６の直鎖状又は分岐状のアルケニル基を示し、例えば１，２－ジフルオロエテニル基、２，２－ジフルオロエテニル基、又は３，３－ジフルオロ－２－プロペニル基等を挙げることができる。 In the present invention, the term “haloalkenyl” is the same or different and represents a linear or branched alkenyl group having 2 to 6 carbon atoms, which is substituted with 1 to 4 halogen atoms. , 2-difluoroethenyl group, 2,2-difluoroethenyl group, 3,3-difluoro-2-propenyl group, and the like.
　本願発明において、「アルコキシ」という用語は、アルキル部分が上記の意味である（アルキル）－Ｏ－基を示し、例えば、メトキシ基、エトキシ基、ｎ－プロポキシ基、イソプロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、又はｔ－ブトキシ基等を挙げることができる。 In the present invention, the term “alkoxy” refers to an (alkyl) -O— group in which the alkyl moiety has the above meaning, for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group. , S-butoxy group, t-butoxy group and the like.
　本願発明において、「ハロアルコキシ」という用語は、ハロアルキル部分が上記の意味である（ハロアルキル）－Ｏ－基を示し、例えばモノフルオロメトキシ基、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、又は２，２，２－トリフルオロエトキシ基等を挙げることができる。 In the present invention, the term “haloalkoxy” refers to a (haloalkyl) -O— group in which the haloalkyl moiety has the above meaning, for example, a monofluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, 2,2-difluoro An ethoxy group, a 2,2,2-trifluoroethoxy group, etc. can be mentioned.
　本願発明において、「アシル」という用語、あるいは、アシルアルコキシにおける「アシル」という用語、アシルオキシアルキルにおける「アシル」という用語及びアシルオキシにおける「アシル」という用語はいずれも、（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－で表される基を示し、例えば、アセチル基、プロピオニル基、ブチリル基、又はイソブチリル基等を挙げることができる。なお、本願において、脂肪族炭化水素基とは、アルキル、アルケニル、アルキニル、シクロアルキル、シクロアルケニル、及びシクロアルキニルを意味する。 In the present invention, the term “acyl”, or the term “acyl” in acylalkoxy, the term “acyl” in acyloxyalkyl, and the term “acyl” in acyloxy are all (with 1 to 8 carbon atoms). A group represented by a linear or branched aliphatic hydrocarbon group) —CO—, and examples thereof include an acetyl group, a propionyl group, a butyryl group, and an isobutyryl group. In the present application, the aliphatic hydrocarbon group means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkynyl.
　本願発明において、「アシルアルコキシ」という用語は、上記に示した１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基を示し、例えば、アセチルメトキシ基、アセチルエトキシ基、アセチルプロポキシ基等を挙げることができる。 In the present invention, the term “acylalkoxy” refers to a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by 1 to 5 acyl groups as described above. Group, acetylethoxy group, acetylpropoxy group and the like.
　本願発明において、「アシルオキシ」という用語は、（炭素原子数が１～８の直鎖状又は分岐状の脂肪族炭化水素基）－ＣＯ－Ｏ－基を示し、例えば、アセトキシ基、プロピオニルオキシ基、イソプロピオニルオキシ基、又はピバロイルオキシ基等を挙げることができる。 In the present invention, the term “acyloxy” refers to a (linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— group, for example, an acetoxy group, propionyloxy group , An isopropionyloxy group, or a pivaloyloxy group.
　本願発明において、「アシルオキシアルキル」という用語は、上記に示した１～５個のアシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基を示し、例えば、アセトキシメチル基、アセトキシエチル基、又はアセトキシプロピル基等を挙げることができる。 In the present invention, the term “acyloxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 acyl groups as described above, for example, acetoxymethyl A group, an acetoxyethyl group, an acetoxypropyl group, and the like.
　本願発明において、「アルキルスルホニル」という用語は、アルキル部分が上記の意味である（アルキル）－ＳＯ２－基を示し、例えば、メチルスルホニル基、エチルスルホニル基、ｎ－プロピルスルホニル基、又はイソプロピルスルホニル基等を挙げることができる。 In the present invention, the term “alkylsulfonyl” refers to an (alkyl) -SO 2 — group in which the alkyl moiety has the above meaning, for example, a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, or an isopropylsulfonyl group. Examples include groups.
　本願発明において、「アルキルスルホニルアルキル」という用語は、上記に示した１～５個のアルキルスルホニル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基を示し、例えば、メチルスルホニルメチル基、メチルスルホニルエチル基、又はメチルスルホニルプロピル基等を挙げることができる。 In the present invention, the term “alkylsulfonylalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 alkylsulfonyl groups shown above, for example, A methylsulfonylmethyl group, a methylsulfonylethyl group, or a methylsulfonylpropyl group can be exemplified.
　本願発明において、「シロキシ」という用語は、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５，Ｒ６，Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）を示し、例えば、トリメチルシロキシ基、トリエチルシロキシ基、トリイソプロピルシロキシ基、ｔ－ブチルジメチルシロキシ基、ｔ－ブチルジフェニルシロキシ基等を挙げることができる。 In the present invention, the term “siloxy” refers to —OSiR 5 R 6 R 7 (R 5 , R 6 , R 7 are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, two All may be the same substituents or all different substituents), for example, trimethylsiloxy group, triethylsiloxy group, triisopropylsiloxy group, t-butyldimethylsiloxy group, t-butyldiphenylsiloxy group, etc. Can do.
　本発明において、「シロキシアルキル」という用語は、上記に示した１～５個のシロキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基を示し、例えば、トリメチルシロキシメチル基、トリメチルシロキシエチル基、トリメチルシロキシプロピル基、トリエチルシロキシメチル基、又はｔ－ブチルジメチルシロキシ基等を挙げることができる。 In the present invention, the term “siloxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 siloxy groups shown above, for example, trimethylsiloxy Examples thereof include a methyl group, a trimethylsiloxyethyl group, a trimethylsiloxypropyl group, a triethylsiloxymethyl group, and a t-butyldimethylsiloxy group.
　本願発明において、「ヒドロキシアルキル」という用語は、１～５個のヒドロキシル基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基を示し、例えば、ヒドロキシメチル基、ヒドロキシエチル基、ヒドロキシプロピル基、又はヒドロキシイソプロピル基等を挙げることができる。 In the present invention, the term “hydroxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 hydroxyl groups, such as a hydroxymethyl group, hydroxyethyl group, and the like. Group, hydroxypropyl group, hydroxyisopropyl group and the like.
　本願発明において、「アルコキシアルキル」という用語は、上記に示した１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基を示し、例えば、メトキシメチル基、エトキシメチル基、プロポキシメチル基、又はイソプロポキシメチル基等を挙げることができる。 In the present invention, the term “alkoxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 alkoxy groups as described above, for example, methoxymethyl A group, an ethoxymethyl group, a propoxymethyl group, or an isopropoxymethyl group.
　本願発明において、「アルキルチオ」という用語は、アルキル部分が上記の意味である（アルキル）－Ｓ－基を示し、例えば、メチルチオ基、エチルチオ基、又はプロピルチオ基等を挙げることができる。 In the present invention, the term “alkylthio” refers to an (alkyl) -S— group in which the alkyl moiety has the above meaning, and examples include a methylthio group, an ethylthio group, or a propylthio group.
　本願発明において、「ハロアルキルチオ」という用語は、ハロアルキル部分が上記の意味である（ハロアルキル）－Ｓ－基を示し、例えば、モノフルオロメチルチオ基、ジフルオロメチルチオ基、トリフルオロメチルチオ基、２，２－ジフルオロエチルチオ基、又は２，２，２－トリフルオロエチルチオ基等を挙げることができる。 In the present invention, the term “haloalkylthio” refers to a (haloalkyl) -S— group in which the haloalkyl moiety is as defined above, for example, a monofluoromethylthio group, a difluoromethylthio group, a trifluoromethylthio group, 2,2- A difluoroethylthio group or a 2,2,2-trifluoroethylthio group can be exemplified.
　本願発明において、「アルキルチオアルキル」という用語は、上記に示した１～５個のアルキルチオ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基を示し、例えば、メチルチオメチル基、エチルチオメチル基、メチルチオエチル基、又はエチルチオエチル基等を挙げることができる。 In the present invention, the term “alkylthioalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 alkylthio groups shown above, for example, methylthiomethyl A group, an ethylthiomethyl group, a methylthioethyl group, or an ethylthioethyl group.
　本願発明において、「ジアルコキシアセタール」という用語は、上記に示したアルコキシ基がメチル基に２個置換したジアルコキシメチル基を示し、ジメトキシメチル基、ジエトキシメチル基、又はジプロポキシメチル基等を挙げることができる。 In the present invention, the term “dialkoxyacetal” refers to a dialkoxymethyl group in which the above-mentioned alkoxy group is substituted by two methyl groups, such as a dimethoxymethyl group, a diethoxymethyl group, or a dipropoxymethyl group. Can be mentioned.
　本願発明において、「アルコキシアルコキシ」という用語は、上記に示した１～５個のアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルコキシ基を示し、例えば、メトキシメトキシ基、メトキシエトキシ基、又はメトキシプロポキシ基等を挙げることができる。 In the present invention, the term “alkoxyalkoxy” refers to a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by 1 to 5 alkoxy groups as described above, for example, methoxymethoxy Group, methoxyethoxy group, methoxypropoxy group and the like.
　本願発明において、「ハロアルコキシアルキル」という用語は、上記に示した１～５個のハロアルコキシ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基を示し、例えば、モノフルオロメトキシメチル基、ジフルオロメトキシメチル基、トリフルオロメトキシメチル基等を挙げることができる。 In the present invention, the term “haloalkoxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 haloalkoxy groups as described above. A monofluoromethoxymethyl group, a difluoromethoxymethyl group, a trifluoromethoxymethyl group, etc. can be mentioned.
　本願発明において、「シアノアルキル」という用語は、１～５個のシアノ基により置換された炭素原子数１～３の直鎖状又は分岐状のアルキル基を示し、例えば、シアノメチル基、シアノエチル基、又はシアノプロピル基等を挙げることができる。 In the present invention, the term “cyanoalkyl” represents a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups, such as a cyanomethyl group, a cyanoethyl group, Or a cyanopropyl group etc. can be mentioned.
　本願発明において、「フェニル」、「オキサゾリル」、「イソキサゾリル」、「フリル」、「ベンゾフリル」、「イソベンゾフリル」、「ジヒドロベンゾフリル」、「チアゾリル」、「イソチアゾリル」、「ナフチル」、「ピリミジニル」、「ピラジニル」、「キノキサリル」、「キナゾリル」、「ピリジル」、「キノリル」、「イソキノリル」、「ベンゾチアゾリル」、「ベンゾイソチアゾリル」、「ピロリル」、「インドリル」、「イソインドリル」、「ベンゾオキサゾリル」、「ベンゾイソオキサゾリル」、「チエニル」、「ベンゾチエニル」、「イミダゾリル」、「ベンズイミダゾリル」、「ピラゾリル」、「ピリドニル」、「トリアジニル」、「トリアゾリル」、「チアジアゾリル」、「オキサジアゾリル」、「ベンゾジオキソリル」、「テトラゾリル」、「フェロセニル」は、同一又は異なっている１以上の置換基を有していてもよく、置換基を有していなくてもよい。 In the present invention, “phenyl”, “oxazolyl”, “isoxazolyl”, “furyl”, “benzofuryl”, “isobenzofuryl”, “dihydrobenzofuryl”, “thiazolyl”, “isothiazolyl”, “naphthyl”, “pyrimidinyl” ”,“ Pyrazinyl ”,“ quinoxalyl ”,“ quinazolyl ”,“ pyridyl ”,“ quinolyl ”,“ isoquinolyl ”,“ benzothiazolyl ”,“ benzoisothiazolyl ”,“ pyrrolyl ”,“ indolyl ”,“ isoindolyl ”,“ Benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl ”,“ Oxadiazolyl ”,“ Benzodioxo ” Le "," tetrazolyl "," ferrocenyl "may have one or more substituents the same or different, may not have a substituent.
　本願発明において、「フェノキシ」という用語は、同一又は異なっていてもよい１以上の置換基を有するフェノキシ基及び無置換のフェノキシ基を包含する。 In the present invention, the term “phenoxy” includes a phenoxy group having one or more substituents which may be the same or different, and an unsubstituted phenoxy group.
　本願発明において、「ベンジル」という用語は、同一又は異なっている１以上の置換基を有するベンジル基及び無置換のベンジル基を包含する。 In the present invention, the term “benzyl” includes a benzyl group having one or more substituents which are the same or different and an unsubstituted benzyl group.
　本願発明において、「ベンジルオキシ」という用語は、同一又は異なっている１以上の置換基を有するベンジルオキシ基及び無置換のベンジルオキシ基を包含する。 In the present invention, the term “benzyloxy” includes a benzyloxy group having one or more substituents which are the same or different and an unsubstituted benzyloxy group.
　本願発明において、「プロパルギル」という用語は、アルキン末端に置換基を有するプロパルギル基及び無置換のプロパルギル基を包含する。 In the present invention, the term “propargyl” includes propargyl groups having a substituent at the alkyne end and unsubstituted propargyl groups.
　本願発明において、「プロパルギルオキシ」という用語は、アルキン末端に置換基を有するプロパルギルオキシ基及び無置換のプロパルギルオキシ基を包含する。 In the present invention, the term “propargyloxy” includes a propargyloxy group having a substituent at the alkyne end and an unsubstituted propargyloxy group.
　本願発明において、「ヘテロアリール」という用語は、オキサゾリル、イソキサゾリル、フリル、ベンゾフリル、イソベンゾフリル、ジヒドロベンゾフリル、チアゾリル、イソチアゾリル、ナフチル、ピリミジニル、ピラジニル、キノキサリル、キナゾリル、ピリジル、キノリル、イソキノリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ピロリル、インドリル、イソインドリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、チエニル、ベンゾチエニル、イミダゾリル、ベンズイミダゾリル、ピラゾリル、ピリドニル、トリアジニル、トリアゾリル、チアジアゾリル、オキサジアゾリル、テトラゾリル、フェロセニルを包含する。これらの基は、同一又は異なっていてもよい１以上の置換基を有していてもよく、置換基を有していなくてもよい。 In the present invention, the term “heteroaryl” is oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, Includes benzoisothiazolyl, pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl, ferrocenyl . These groups may have one or more substituents which may be the same or different, and may not have a substituent.
　本願発明において、「フェニレン」という用語は、１，２－フェニレン（ｏ－フェニレン）、１，３－フェニレン（ｍ－フェニレン）および１，４－フェニレン（ｐ－フェニレン）を含有する。これらの基は、同一又は異なっていてもよい１以上の置換基を有していてもよく、置換基を有していなくてもよい。 In the present invention, the term “phenylene” includes 1,2-phenylene (o-phenylene), 1,3-phenylene (m-phenylene) and 1,4-phenylene (p-phenylene). These groups may have one or more substituents which may be the same or different, and may not have a substituent.
　本発明において、１～３個のＮ、Ｏ、Ｓ原子を環に含む「５若しくは６員環のヘテロアレン」という用語は、５若しくは６個の環原子を有する芳香族複素環を示し、例えば、オキサゾール、イソキサゾール、フラン、チアゾール、イソチアゾール、ピリミジン、ピラジン、ピリジン、ピロール、チオフェン、イミダゾール、ピラゾール等を挙げることができる。 In the present invention, the term “5- or 6-membered heteroallene” containing 1 to 3 N, O, S atoms in the ring represents an aromatic heterocycle having 5 or 6 ring atoms, for example, Examples thereof include oxazole, isoxazole, furan, thiazole, isothiazole, pyrimidine, pyrazine, pyridine, pyrrole, thiophene, imidazole, and pyrazole.
　本発明において、「５若しくは６員環のヘテロアレンジイル」という用語は、上記に示した５若しくは６個の環原子を有する芳香族複素環に由来する２価の基、２箇所の結合の位置を有する芳香族複素環を示し、例えば、オキサゾールジイル、イソキサゾールジイル、フランジイル、チアゾールジイル、イソチアゾールジイル、ピリミジンジイル、ピラジンジイル、ピリジンジイル、ピロールジイル、チオフェンジイル、イミダゾールジイル、ピラゾールジイル、ピリドンジイル等を挙げることができる。 In the present invention, the term “5- or 6-membered heteroarrangeyl” is a divalent group derived from the aromatic heterocycle having 5 or 6 ring atoms shown above, and the position of the bond at two positions. For example, oxazolediyl, isoxazolediyl, furandyl, thiazolediyl, isothiazolediyl, pyrimidinediyl, pyrazinediyl, pyridinediyl, pyrroldiyl, thiophenediyl, imidazolediyl, pyrazolediyl, pyridonediyl, etc. Can be mentioned.
　本願発明において、「環状エーテル」という用語は、エポキシ、オキセタン、テトラヒドロフラン、テトラヒドロピラン、ジオキソラン、ジオキサンを含有する。 In the present invention, the term “cyclic ether” includes epoxy, oxetane, tetrahydrofuran, tetrahydropyran, dioxolane, and dioxane.
　本願発明において、「環状アミン」という用語は、ピロリジニル、イミダゾリジニル、ピラゾリジニル、ピペリジニル、ピペラジニル、モルホリニルを包含する。 In the present invention, the term “cyclic amine” includes pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholinyl.
　本願発明において、「イミド」という用語は、鎖状イミド、環状イミドを包含する。 In the present invention, the term “imide” includes a chain imide and a cyclic imide.
　式［Ｉ］で示される本発明の化合物はピリジル基を有しているので、これに由来する酸付加塩も本発明に含まれる。 Since the compound of the present invention represented by the formula [I] has a pyridyl group, an acid addition salt derived therefrom is also included in the present invention.
　酸付加塩を形成する酸としては、例えば、塩酸、臭化水素酸、硝酸、硫酸、リン酸などの無機酸、ギ酸、酢酸、シュウ酸、フマル酸、アジピン酸、ステアリン酸、オレイン酸、アコニット酸などのカルボン酸、あるいはメタンスルホン酸、ベンゼンスルホン酸、ｐ－トルエンスルホン酸などのスルホン酸などを挙げることができる。 Examples of acids that form acid addition salts include inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, and phosphoric acid, formic acid, acetic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, and aconite. Examples thereof include carboxylic acids such as acids, and sulfonic acids such as methanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid.
　下記式で示される本発明化合物［Ｉ］は、下記の反応工程に示すように、例えば一般式［ＩＩ］で示されるスルホン酸誘導体と、一般式［ＩＩＩ］で示されるアミン誘導体を塩基（base）および溶媒の存在下反応させることにより製造できる。 As shown in the following reaction step, the present compound [I] represented by the following formula comprises, for example, a sulfonic acid derivative represented by the general formula [II] and an amine derivative represented by the general formula [III] as a base ) And a solvent in the presence of a solvent.
Figure JPOXMLDOC01-appb-C000006
 　（式中、Ｒ１，Ｒ２，Ｒ３，Ｒ４，Ａ及びＢは、前記と同義である。）
Figure JPOXMLDOC01-appb-C000006
 (In the formula, R 1 , R 2 , R 3 , R 4 , A and B are as defined above.)
　また、以上のようにして製造された化合物［Ｉ］が末端アルキンである場合（Ｂ＝Ｈ，化合物Ｉ－１）、カップリング反応を利用して置換基を導入する事も可能である。 Further, when the compound [I] produced as described above is a terminal alkyne (B = H, compound I-1), it is also possible to introduce a substituent using a coupling reaction.
Figure JPOXMLDOC01-appb-C000007
 　（式中、Ｘは臭素またはヨウ素、Ｂはフェニル、ヘテロアリール、アルケニル、Ｒ１，Ｒ２，Ｒ３，Ｒ４及びＡは、前記と同義である。）
Figure JPOXMLDOC01-appb-C000007
 (Wherein X is bromine or iodine, B is phenyl, heteroaryl, alkenyl, R 1 , R 2 , R 3 , R 4 and A are as defined above.)
　さらに、化合物［Ｉ－２］と末端アルキン［Ｖ］から、カップリング反応を利用して置換基を導入する事も可能である。 Furthermore, it is also possible to introduce a substituent from the compound [I-2] and the terminal alkyne [V] using a coupling reaction.
Figure JPOXMLDOC01-appb-C000008
 　（式中、Ｘは臭素またはヨウ素、Ｒ１，Ｒ２，Ｒ３，Ｒ４，Ａ及びＢは、前記と同義である。）
Figure JPOXMLDOC01-appb-C000008
 (In the formula, X is bromine or iodine, and R 1 , R 2 , R 3 , R 4 , A and B are as defined above.)
［防除効果］
　本願発明において、「有害生物」という用語は、農園芸用植物に対するあらゆる病害虫及び農園芸用植物に対するあらゆる病原菌を包含する。 [Control effect]
In the present invention, the term “pest” includes all pests on agricultural and horticultural plants and all pathogenic fungi on agricultural and horticultural plants.
　本発明の化合物（Ｉ）で防除効果が認められる農園芸用有害生物を以下に例示する。 Examples of agricultural and horticultural pests that have a controlling effect with the compound (I) of the present invention are shown below.
（農園芸植物に対する病原菌類）
　農園芸植物に対する病原菌類の例としては、ネコブカビ門(Plasmodiophoromycota)、卵菌門(Oomycota)、接合菌門(Zygomycota)、子嚢菌門(Ascomycota)、担子菌門(Basidiomycota)、不完全菌門(Deuteromycota)および細菌類などが属し、本願発明に係るスルホンアミド誘導体は、これら病原菌類に起因する植物の病害を防除できる。次に具体的な菌名を例としてあげるが、必ずしもこれらに限定されるものではない。 (Pathogenic fungi against agricultural and horticultural plants)
Examples of pathogenic fungi for agricultural and horticultural plants include Plasmodiophoromycota, Omyycota, Zygomycota, Ascomycota, Basidiomycota, Incomplete fungus ( Deuteromycota) and bacteria belong, and the sulfonamide derivative according to the present invention can control plant diseases caused by these pathogenic fungi. Next, specific names of bacteria are given as examples, but are not necessarily limited thereto.
　農園芸病原菌として、例えば、イネいもち病(Pyricularia oryzae)、イネごま葉枯病(Cochliobolus miyabeanus)、イネ紋枯病(Rhizoctonia solani)、イネ馬鹿苗病(Gibberella fujikuroi)、コムギ赤かび病(Gibberella zeae)、コムギ赤さび病(Puccinia recondita)、コムギうどんこ病(Erysiphe graminis f.sp. tritici)、コムギ眼紋病(Pseudocercosporella herpotrichoides)、コムギ炭疽病(Colletotrichum graminicola)、コムギ葉枯病(Septoria tritici)、コムギ雪腐大粒菌核病(Sclerotinia borealis)、コムギ雪腐小粒菌核病(Typhula ishikariensis)、ジャガイモそうか病(Streptomyces scabies)、ジャガイモ疫病(Phytophthora infestans)、ジャガイモ黒あざ病(Thanatephorus cucumeris)、ジャガイモ炭疽病(Colletotrichum atramentarium)、ジャガイモ夏疫病(Alternaria solani)、アズキうどんこ病(Erisiphe pisi)、アズキ褐斑病(Cercospora canescens)、アズキ菌核病(Sclerotinia sclerotiorum)、アズキ炭疽病(Colletotrichum phaseolorum)、インゲンマメ褐斑病(Cercospora canescens)、インゲンマメ菌核病(Sclerotinia sclerotiorum)、インゲンマメ炭疽病(Colletotrichum lindemuthiamum)、インゲンマメ灰色かび病(Botrytis cinerea)、ダイズさび病(Phakopsora pachyrhizi)、ダイズ紫斑病(Cercospora kikuchii)、ダイズ炭疽病(Colletotrichum truncatum)、テンサイ褐斑病(Cercospora beticola)、コンニャク炭疽病(Gloeosporium conjac)、コンニャク褐斑病(Septoria perillae)、チャ赤焼病（Pseudomonas syringae)、チャ網もち病(Exobasidium reticulatum)、チャ褐色円星病(Pseudocercospora ocellata, Cercospora chaae)、チャ炭疽病(Colletotrichum theae-sinensis)、チャもち病(Exobasidium vexans)、チャ輪斑病(Pestalotiopsis longiseta)、日本シバカーブラリア葉枯病(Curvularia geniculata)、日本シバ葉腐病(Rhizoctonia solani)、ベントグラス赤焼病(Pythium aphanidermatum)、ベントグラスダラースポット病(Sclerotinia homoeocarpa)、ベントグラスピシウム病(Pythium vanterpoolii、Pythium graminicola)、ホウレンソウ褐斑病(Cercospora beticola)、ホウレンソウ炭疽病(Colletotrichum spinaciae)、ホウレンソウべと病(Peronospora effusa)、カブ白さび病(Albugo macrospora)、キャベツ黒腐病(Xanthomonas campestris pv. Campestris)、キャベツ菌核病(Sclerotinia sclerotiorum)、キャベツ黒すす病(Alternaria brassicicola)、キャベツべと病(Peronospora parasitica)、ダイコン軟腐病（Erwinia carotovora）、コマツナ炭疽病(Colletotrichum higginsianum)、ハクサイ菌核病(Sclerotinia sclerotiorum)、ハクサイ黒斑病(Alternaria brassicae、Alternaria brassicicola)、ハクサイ根こぶ病(Plasmodiophora brassicae)、カボチャ黒斑病(Alternaria cucumerina)、カボチャ疫病(Phytophthora capsici)、カボチャべと病(Pseudoperonospora cubensis)、キュウリ斑点細菌病（Pseudomonas syringae)、キュウリうどんこ病(Sphaerotheca cucurbitae)、キュウリ疫病(Phytophthora melonis)、キュウリ褐斑病(Corynespora cassiicola)、キュウリ菌核病(Sclerotinia sclerotiorum)、キュウリ黒斑病(Alternaria cucumerina)、キュウリ炭疽病(Colletotrichum orbiculare)、キュウリつる枯病(Didymella bryoniae)、キュウリつる割病(Fusarium oxysporum f.sp. cucumerinum)、キュウリ苗立枯病(Pythium cucurbitacearum、Rhyzoctonia solani)、キュウリ灰色かび病(Botrytis cinerea)、キュウリべと病(Pseudoperonospora cubensis)、スイカうどんこ病(Sphaerotheca fuliginea)、スイカ疫病(Phytophthora cryptogea)、スイカ炭疽病(Colletotrichum orbiculare)、スイカべと病(Pseudoperonospora cubensis)、メロン褐斑病(Corynespora cassiicola)、メロン菌核病(Sclerotinia sclerotiorum)、メロンつる割病(Fusarium oxysporum f.sp. melonis)、メロンべと病(Pseudoperonospora cubensis)、シュンギク萎凋病(Fusarium oxysporum)、シュンギク菌核病(Sclerotinia sclerotiorum)、シュンギクさび病(Puccinia cnici-oleracei)、シュンギク炭疽病(Gloeosporium chrysanthemi、Gloeosporium carthami)、ショウガ根茎腐敗病(Pythium ultimum var. ultimum)、ニンジン萎凋病(Fusarium oxysporum)、ニンジンうどんこ病(Erysiphe heraclei)、ニンジン菌核病(Sclerotinia intermedia、Sclerotinia sclerotiorum)、ニンジン黒葉枯病(Alternaria dauci)、ニンジン黒斑病(Alternaria radicina)、トウガラシ・ピーマン青枯病(Ralstonia solanacearum)、トウガラシ・ピーマンうどんこ病(Oidiopsis sicula)、トウガラシ、ピーマン疫病(Phytophthora capsici)、トウガラシ・ピーマン菌核病(Sclerotinia sclerotiorum)、トウガラシ・ピーマン炭疽病(Colletotrichum gloeosporioides)、トウガラシ・ピーマン斑点病(Cercospora capsici)、トマト萎凋病(Fusarium oxysporum f.sp. lycopersici)、トマトうどんこ病(Oidium violae、Oidiopsis sicula)、トマト疫病(Phytophthora infestans)、トマト菌核病(Sclerotinia sclerotiorum)、トマト灰色かび病(Botrytis cinerea)、トマト葉かび病(Fulvia fulva)、トマト斑点病(Stemphylium lycopersici)、トマト輪紋病(Alternaria solani)、ナス疫病(Phytophthora infestans)、ナス褐色斑点病(Thanatephorus cucumeris)、ナス褐色腐敗病(Phytophthora capsici)、ナスすすかび病(Mycovellosiella nattrassii)、ナス半身萎凋病(Verticillium dahliae)、イチゴ萎黄病(Fusarium oxysporum)、イチゴ萎凋病(Verticillium dahliae)、イチゴうどんこ病(Sphaerotheca humuli)、イチゴ疫病(Phytophthora nicotianae var. parasitica)、イチゴ果実腐敗病(Pythium ultimum var. ultimum)、イチゴ菌核病(Sclerotinia sclerotiorum)、イチゴ黒斑病(Alternaria alternata)、イチゴ蛇の目病(Mycosphaerella fragariae)、イチゴ炭疽病(Colletotrichum acutatum、Glomerella cingulata)、イチゴ灰色かび病(Botrytis cinerea)、アスパラガス褐斑病(Cercospora asparagi)、アスパラガス茎枯病(Phomopsis asparagi)、アスパラガスさび病(Puccinia asparagi-lucidi)、アスパラガス炭疽病(Colletotrichum gloeosporioides)、アスパラガス灰色かび病(Botrytis cinerea)、アスパラガス斑点病(Stemphylium botryosum)、タマネギ疫病(Phytophthora nicotianae)、タマネギ黄斑病(Cladosporium allii-cepae)、タマネギ乾腐病(Fusarium oxysporum f.sp. cepae)、タマネギ菌核病(Sclerotinia sclerotiorum)、タマネギ黒点葉枯病(Septoria alliacea)、タマネギ黒斑病(Alternaria porri)、タマネギさび病(Puccinia allii)、タマネギ小菌核病(Sclerotinia allii)、タマネギ小菌核性腐敗病(Botrytis squamosa)、タマネギ白色疫病(Phytophthora porri)、タマネギ炭疽病(Colletotrichum circinans)、タマネギ灰色かび病(Botrytis cinerea)、タマネギ灰色腐敗病(Botrytis allii)、タマネギ葉枯病(Pleospora herbarum)、タマネギべと病(Peronospora destructor)、ニラさび病(Puccinia allii)、ニラ白斑葉枯病(Botrytis byssoidea)、ネギ疫病(Phytophthora nicotianae)、ネギ萎凋病(Fusarium oxysporum f. sp. cepae)、ネギ黒渋病(Mycosphaerella allicina)、ネギ黒点葉枯病(Septria alliacea)、ネギ黒斑病(Alternaria porri)、ネギ小菌核病(Sclerotinia allii)、ネギさび病(Puccinia allii)、ネギ小菌核腐敗病(Botrytis squamosa)、ネギ白色疫病(Phythoththora porri)、ネギ炭疽病(Colletotrichum circinans)、ネギべと病(Peronospora destructor)、キク黒斑病(Septoria chrysanthemella)、キク白さび病(Puccinia horiana)、マンゴー炭疽病(Colletotrichum gloeosporioides)、カキうどんこ病(Phyllactinia kakicola)、カキ角斑病(Cercospora kakivora)、カキ角斑落葉病(Cercospora kaki)、カキ褐紋病(Macrophoma kaki)、カキ黒星病(Fusicladium levieri)、カキ黒点病(Phomopsis kakivora)、カキ黒斑病(Pseudocercospora fuliginosa)、カキ縮葉病(Physalospora kaki)、カキすす病(Aureobasidium pullulans、Capnophaeum fuliginodes、Cladosporium herbarum、Microxyphium sp.、Scorias communis、Tripospermum juglandis)、カキすす点病(Zygophiala jamaicensis)、カキ炭疽病(Gloeosporium kaki)、カキ灰色かび病(Botrytis cinerea)、カキ葉枯病(Pestalotia diospyri)、カキ円星落葉病(Mycosphaerella nawae)、バナナ炭疽病(Colletotrichum musae)、ウメうどんこ病(Podosphaera tridactyla、Sphaerotheca pannosa)、ウメ枝枯病(Botryosphaeria dothidea)、ウメ菌核病(Sclerotinia sclerotiorum)、ウメ黒星病(Cladosporium carpophilum)、ウメ縮葉病(Taphrina mume)、ウメ白さび病(Leucotelium pruni-persicae)、ウメ白紋羽病(Rosellinia necatrix)、ウメ心腐病(Fusarium lateritium)、ウメせん孔病(Pseudocercospora circumscissa)、ウメそうか病(Sphaceloma pruni-domesticae)、ウメ炭疽病(Glomerella cingulata)、ウメ灰色かび病(Botrytis cinerea)、ウメ灰星病(Monilinia fructicola、Monilinia laxa)、オウトウうどんこ病(Podosphaera tridactyla)、オウトウ菌核病(Sclerotinia sclerotiorum)、オウトウ黒かび病(Rhizopus nigricans)、オウトウ炭疽病(Glomerella cingulata)、オウトウ灰色かび病(Botrytis cinerea)、オウトウ灰星病(Monilinia fructicola)、セイヨウナシうどんこ病(Phyllactinia mali)、セイヨウナシ疫病(Phytophthora cactorum、phytophthora syringae)、セイヨウナシ黒星病(Venturia pirina)、セイヨウナシ炭疽病(Colletotrichum gloeosporioides)、ナシ赤星病(Gymnosporangium asiaticum)、ナシ黒星病(Venturia nashicola)、ナシ黒斑病(Alternaria kikuchiana)、ナシすす点病(Leptothyrium pomi)、ナシ炭疽病(Glomerella cingulata)、ナシ灰色かび病(Botrytis cinerea)、ナシ灰星病(Monilinia fructigena)、ナシ葉炭疽病(Colletotrichum gloeosporioides)、ナシ輪紋病(Physalospora piricola)、モモ赤かび病(Fusarium oxysporum、Gibberella zeae)、モモうどんこ病(Podosphaera tridactyla、Sphaerotheca pannosa)、モモ菌核病(Sclerotinia sclerotiorum)、モモ黒かび病(Rhizopus nigricans)、モモ黒星病(Cladosporium carpophilum)、モモ白さび病(Leucotelium pruni-persicae)、モモすすかび病(Stenella sp.)、モモせん孔病(Pseudocercospora circumscissa、Phyllosticta persicae)、モモ炭疽病(Gloeosporium laeticolor)、モモ灰色かび病(Botrytis cinerea)、モモ灰星病(Monilinia fructicola)、モモホモプシス腐敗病(Phomopsis sp.)、リンゴ赤星病(Gymnosporangium yamadae)、リンゴうどんこ病(Podosphaera leucotricha)、リンゴ疫病(Phytophthora cactorum、phytophthora cambivola、Phytophthora syringae)、リンゴ褐斑病(Diplocarpon mali)、リンゴ環紋葉枯病(Cristulariella moricola)、リンゴ黒星病(Venturia inaequalis)、リンゴすす点病(Zygophiala jamaicensis)、リンゴすす斑病(Gloeodes pomigena)、リンゴ斑点落葉病(Alternaria mali)、リンゴ紫紋羽病(Helicobasidium mompa)、リンゴ輪紋病(Botryosphaeria berengeriana)、ブドウうどんこ病(Uncinula necator)、ブドウ枝枯菌核病(Sclerotinia sclerotiorum)、ブドウ晩腐病(Glomerella cingulata)、ブドウ褐斑病(Pseudocercospora vitis)、ブドウ褐斑葉枯病(Briosia ampelophaga)、ブドウ黒腐病(Phyllosticta ampelicida)、ブドウ黒とう病(Elsinoe ampelina)、ブドウすす点病(Zygophiala jamaicensis)、ブドウつる割病(Phomopsis viticola)、ブドウべと病(Plasmopara viticola)、クリうどんこ病(Microsphaera alphitoides)、クリ褐斑病(Morenoella quercina)、クリすす病(Capnodium salicinum)、クリ炭疽病(Glomerella cingulata)、クリ葉枯病(Monochaetia monochaeta)、カンキツかいよう病(Xanthomonas campestris)、カンキツ青かび病(Penicillium italicum)、カンキツ黄斑病(Mycosphaerella citri、Mycosphaerella horii)、カンキツ褐色腐敗病(Phytophthora citrophthora)、カンキツ黒点病(Diaporthe citri)、カンキツすす点病(Leptothyrium pomi)、カンキツそうか病(Elsinoe fawcettii)、カンキツそばかす病(Mycosphaerella pinodes)、カンキツ炭疽病(Colleto
trichum gloeosporioides)、カンキツ緑かび病(Penicillium digitatum)などが挙げられる。 Examples of agricultural and horticultural pathogens include, for example, rice blast (Pyricularia oryzae), rice sesame leaf blight (Cochliobolus miyabeanus), rice blight (Rhizoctonia solani), rice idiot (Gibberella fujikuroi), wheat red mold (Gibberella zeae) ), Wheat red rust (Puccinia recondita), wheat powdery mildew (Erysiphe graminis f.sp. Sclerotinia borealis, wheat syrup, Typhula ishikariensis, Streptomyces scabies, Phytophthora infestans, Thanatephorus cucumeris, potato Anthracnose (Colletotrichum atramentarium), potato summer plague (Alternaria solani), azuki bean powder (Erisiphe pisi), azuki bean disease (Cercospora canescens), azuki bean sclerotia (Sclerotinia sclerotioru) m), azuki bean anthracnose (Colletotrichum phaseolorum), kidney bean brown spot (Cercospora canescens), kidney bean sclerotia (Sclerotinia sclerotiorum), bean anthracnose (Colletotrichum lindemuthiamum), kidney bean gray mold (Botrytis cinerea) Phakopsora pachyrhizi), soybean purple spot (Cercospora kikuchii), soybean anthracnose (Colletotrichum truncatum), sugar beet brown spot (Cercospora beticola), konjac anthracnose (Gloeosporium conjac), konjac brown spot (Septoria perillae) (Pseudomonas syringae), tea net blast (Exobasidium reticulatum), tea brown rot (Pseudocercospora ocellata, Cercospora chaae), tea anthracnose (Colletotrichum theae-sinensis), tea blast (Exobasidium vexans), tea ring spot ( Pestalotiopsis longiseta), Japanese Shiva Carbaria leaf blight (Curvularia geniculata), Japanese Shiba leaf rot (Rhizoctonia solani), Bentgrass red blight (Pythium aphanidermatum), Bentgrass Dollar spot disease (Sclerotinia homoeocarpa), Bentgrass Picium disease (Pythium vanterpoolii, Pythium graminicola), Spinach brown spot (Cercospora beticola), Spinach anthracnose (Colletotrichum spinaciae), Spinach downy mildew (Peronospora effusa) (Albugo macrospora), cabbage black rot (Xanthomonas campestris pv. Campestris), cabbage mycosis (Sclerotinia sclerotiorum), cabbage black soot (Alternaria brassicicola), cabbage downy mildew (Peronospora parasitica), radish soft rot (Erwinia carotovora) ), Colletotrichum higginsianum, Sclerotinia sclerotiorum, Chinese cabbage black spot (Alternaria brassicae, Alternaria brassicicola), Chinese cabbage root-knot (Plasmodiophora brassicae), Pumpkin black spot (Alternaria cucumerina) Plague (Phytophthora capsici), pumpkin downy mildew (Pseudoperonospora cubensis), cucumber spots Diseases (Pseudomonas syringae), cucumber powdery mildew (Sphaerotheca cucurbitae), cucumber plague (Phytophthora melonis), cucumber brown spot (Corynespora cassiicola), cucumber sclerotia (Sclerotinia sclerotiorum), cucumber black cucumber (Al) Anthracnose (Colletotrichum orbiculare), Cucumber vine blight (Didymella bryoniae), Cucumber vine split (Fusarium oxysporum f.sp. cucumerinum), Cucumber seedling blight (Pythium cucurbitacearum, Rhyzoctonia solani), cucumber gray tis ), Cucumber downy mildew (Pseudoperonospora cubensis), Watermelon powdery mildew (Sphaerotheca fuliginea), Watermelon plague (Phytophthora cryptogea), Watermelon anthracnose (Colletotrichum orbiculare), Watermelon downy mildew (Pseudoperonospora cubensis), Melon brown spot disease cassiicola), melon nuclear disease (Sclerotinia sclerotiorum), melon vine split disease (Fusarium oxysporum f.sp. melonis), melon downy mildew (Pseudoperonospora cubensis), Fusarium oxysporum, Sclerotinia sclerotiorum, Puccinia cnici-oleracei, Shungiku anthracnose (Gloeosporium chrysanthemi, Gloeosporium carthami), Ginger timul var Carrot wilt (Fusarium oxysporum), carrot powdery mildew (Erysiphe heraclei), carrot mycosis (Sclerotinia intermedia, Sclerotinia sclerotiorum), carrot black leaf blight (Alternaria dauci), carrot black spot (Alternaria radicina), red pepper Pepper bacterial wilt (Ralstonia solanacearum), Pepper pepper pepper powdery mildew (Oidiopsis sicula), Pepper pepper, Phytophthora capsici, Pepper pepper sclerotior disease (Sclerotinia sclerotiorum), Pepper glo rio pole Capsici pepper pepper (Cercospora capsici), tomato wilt (Fusarium oxysporum f.sp.lycopersici) ), Tomato powdery mildew (Oidium violae, Oidiopsis sicula), tomato plague (Phytophthora infestans), tomato mycosis (Sclerotinia sclerotiorum), tomato gray mold (Botrytis cinerea), tomato leaf mold (Fulvia fulva), tomato spots Disease (Stemphylium lycopersici), tomato ring rot (Alternaria solani), eggplant plague (Phytophthora infestans), eggplant brown spot disease (Thanatephorus cucumeris), eggplant brown rot (Phytophthora capsici), eggplant subtilis (Mycovellosiella nattrassii) Half body wilt (Verticillium dahliae), strawberry wilt (Fusarium oxysporum), strawberry wilt (Verticillium dahliae), strawberry powdery mildew (Sphaerotheca humuli), strawberry plague (Phytophthora nicotianae var. Parasitica), strawberry fruit rot (Pythium ultimul) var.ultimum), strawberry sclerotia (Sclerotinia sclerotiorum), strawberry black spot (Alternaria alternata), strawberry snake eye disease (Mycosphaerella fragariae), strawberry anthracnose (Colletotrichum acutatum, Glomerella c) ingulata), strawberry gray mold (Botrytis cinerea), asparagus brown spot (Cercospora asparagi), asparagus stem blight (Phomopsis asparagi), asparagus rust (Puccinia asparagi-lucidi), asparagus anthracnose (Colletotrichum gloeosporioides) ), Asparagus gray mold disease (Botrytis cinerea), Asparagus spot disease (Stemphylium botryosum), Onion plague (Phytophthora nicotianae), Onion yellow spot (Cladosporium allii-cepae), Onion dry rot (Fusarium oxysporum f.sp. ), Onion sclerotia (Sclerotinia sclerotiorum), onion black spot blight (Septoria alliacea), onion black spot (Alternaria porri), onion rust (Puccinia allii), onion small sclerotia (Sclerotinia allii), small onion Botrytis squamosa, onion white plague (Phytophthora porri), onion anthracnose (Colletotrichum circinans), onion gray mold (Botrytis cinerea), onion gray rot (Botrytis a llii), onion leaf blight (Pleospora herbarum), onion downy mildew (Peronospora destructor), leek rust (Puccinia allii), leek white leaf blight (Botrytis byssoidea), leek plague (Phytophthora nicotianae), leek wilt ( Fusarium oxysporum f. Sp. Cepae), leeks black astringency (Mycosphaerella allicina), leeks black leaf blight (Septria alliacea), leeks black spot (Alternaria porri), leeks sclerotia nuclear disease (Sclerotinia allii) (Puccinia allii), green onion rot (Botrytis squamosa), green onion white rot (Phythoththora porri), green onion anthracnose (Colletotrichum circinans), leek downy mildew (Peronospora destructor), chrysanthemum black spot (Septoria chrysanthemella), Chrysanthemum rust (Puccinia horiana), mango anthracnose (Colletotrichum gloeosporioides), oyster powdery mildew (Phyllactinia kakicola), oyster keratosis (Cercospora kakivora), oyster keratosis (Cercospora kaki), oyster brown spot ( Macrophoma kaki), oyster black spot disease (Fusicladium levieri), oyster black spot disease (Phomop) sis kakivora), oyster black spot disease (Pseudocercospora fuliginosa), oyster leaf blight (Physalospora kaki), oyster scab (Aureobasidium pullulans, Capnophaeum fuliginodes, Cladosporium herbarum, Microxyphium sp., Scorias communis, Triposperm muss (Zygophiala jamaicensis), oyster anthracnose (Gloeosporium kaki), oyster gray fungus (Botrytis cinerea), oyster leaf blight (Pestalotia diospyri), oyster lobster rot (Mycosphaerella nawae), banana anthracnose (Colletotrichum musae), ume Powdery mildew (Podosphaera tridactyla, Sphaerotheca pannosa), ume branch blight (Botryosphaeria dothidea), ume mycosis (Sclerotinia sclerotiorum), ume black scab (Cladosporium carpophilum), ume white leaf disease (Taphrina mume), ume white rust (Leucotelium pruni-persicae), ume white blight (Rosellinia necatrix), ume heart rot (Fusarium lateritium), ume fistula (Pseudocercospora circumscissa), ume scab (Sphaceloma pruni-domesticae), ume anthrax (Glomerell) a cingulata), ume gray mold disease (Botrytis cinerea), ume gray scab disease (Monilinia fructicola, Monilinia laxa), sweet powdery mildew (Podosphaera tridactyla), sweet potato nuclear disease (Sclerotinia sclerotiorum), sweet potato black mold (Rhizopus gri) ), Sweet potato anthracnose (Glomerella cingulata), sweet potato gray fungus (Botrytis cinerea), sweet pea scab (Monilinia fructicola), pear powdery mildew (Phyllactinia mali), pear plague (Phytophthora cactorum, phytae) Pear black spot disease (Venturia pirina), pear anthracnose disease (Colletotrichum gloeosporioides), pear red star disease (Gymnosporangium asiaticum), pear black spot disease (Venturia nashicola), pear black spot disease (Alternaria kikuchiana), pear soot spot disease (Leptothyrium pomi) , Pear anthracnose (Glomerella cingulata), pear gray mold (Botrytis cinerea), pear ash scab (Monilinia fructigena), pear leaf anthracnose (Colletotrichum gloeosporioides), pear ring rot (Ph ysalospora piricola), peach red mold disease (Fusarium oxysporum, Gibberella zeae), peach powdery mildew (Podosphaera tridactyla, Sphaerotheca pannosa), peach sclerotia (Sclerotinia sclerotiorum), peach black mold disease (Rhizopus nigris) Cladosporium carpophilum), peach leaf rust (Leucotelium pruni-persicae), peach scab (Stenella sp.), Peach perforation (Pseudocercospora circumscissa, Phyllosticta persicae), peach anthracnose (Gloeosporium laeticolor), peach gray rust cinerea), peach ash scab (Monilinia fructicola), peach homoposis rot (Phomopsis sp.), apple red scab (Gymnosporangium yamadae), apple powdery mildew (Podosphaera leucotricha), apple blight (Phytophthora cactorum, phytophthora cophora ), Apple brown spot disease (Diplocarpon mali), apple ring rot (Cristulariella moricola), apple black spot disease (Venturia inaequalis), apple soot spot (Zygophiala jamaicensis), apple soy Spotted disease (Gloeodes pomigena), apple spotted leaf disease (Alternaria mali), apple purple herb disease (Helicobasidium mompa), apple ringworm (Botryosphaeria berengeriana), grape powdery mildew (Uncinula necator), grape blight fungus nuclear disease (Sclerotinia sclerotiorum), grape late rot (Glomerella cingulata), grape brown spot (Pseudocercospora vitis), grape brown leaf blight (Briosia ampelophaga), grape black rot (Phyllosticta ampelicida), grape black rot (Elsinoe ampelina) ), Grape soot spot disease (Zygophiala jamaicensis), grape vine split disease (Phomopsis viticola), grape downy mildew (Plasmopara viticola), chestnut powdery mildew (Microsphaera alphitoides), chestnut brown spot (Morenoella quercina), chestnut soot disease (Capnodium salicinum), chestnut anthracnose (Glomerella cingulata), chestnut leaf blight (Monochaetia monochaeta), citrus scab (Xanthomonas campestris), citrus green mold (Penicillium italicum), citrus yellow spot (Mycosphaerella citri, Mycosphaer h orii), citrus brown rot (Phytophthora citrophthora), citrus black spot (Diaporthe citri), citrus soot spot (Leptothyrium pomi), citrus scab (Elsinoe fawcettii), citrus buckwheat (Mycosphaerella pinodes), citrus charcoal Colleto
trichum gloeosporioides) and citrus green mold (Penicillium digitatum).
　（農園芸植物に対する害虫類およびダニ類等）
　農園芸植物に対する害虫類およびダニ類等の例としては、カメムシ目(Hemiptera)、アザミウマ目(Thysanoptera)、チョウ目(Lepidoptera)、ダニ目(Acari)などが属し、本発明に用いられるスルホンアミド誘導体は、これら害虫類、ダニ類等に起因する植物の被害を防除できる。次に具体的な害虫、ダニ等を例としてあげるが、必ずしもこれらに限定されるものではない。 (Pests and mites on agricultural and horticultural plants)
Examples of pests and mites on agricultural and horticultural plants include the order of Hemiptera, Thysanoptera, Lepidoptera, Acari, etc., and the sulfonamide derivatives used in the present invention Can control plant damage caused by these pests, mites and the like. Next, specific pests, ticks and the like are given as examples, but not necessarily limited thereto.
　害虫類、ダニ類等としては、例えば、ヒメボクトウ(Cossus insularis)、チャノコカクモンハマキ(Adoxophyes honmai)、リンゴコカクモンハマキ(Adoxophyes orana faciata)、ナシヒメシンクイ(Grapholita molesta)、チャハマキ(Homona magnamina)、マメシンクイガ(Leguminivora glycinivorella)、ギンモンハモグリガ(Lyonetia prunifoliella malinella)、チャノホソガ(Caloptilia theivora)、キンモンホソガ(Phyllonorycter ringoniella)、ミカンハモグリガ(Phyllocnistis citrella)、ネギコガ(Acrolepiopsis sapporensis)、コナガ（Plutella xylostella)、リンゴヒメシンクイ（Argyresthia conjugella)、ブドウスカシバ(Nokona regalis)、コスカシバ(Synanthedon hector)、カキノヘタムシガ(Stathmopoda masinissa)、モモシンクイガ(Carposina sasakii)、イラガ(Monema flavescens)、ニカメイガ(Chilo suppressalis)、コブノメイガ(Cnaphalocrocis medinalis)、ハイマダラノメイガ(Hellula undalis)、アワノメイガ(Ostrinia furnacalis)、シバツトガ(Parapediasia teterrella)、スジコナマダラメイガ(Ephestia kuehniella)、ハチノスツヅリガ(Galleria mellonella)、キアゲハ(Papilio machaon hippocrates)、モンシロチョウ(Pieris rapae crucivora)、イチモンジセセリ(Parnara guttata)、ヨモギエダシャク(Ascotis selenaria)、エビガラスズメ(Agrius convolvuli)、ヒメシロモンドクガ(Orgyia thyellina)、アメリカシロヒトリ(Hyphantria cunea)、タマナヤガ(Agrotis ipsilon)、カブラヤガ(Agrotis segetum)、タマナギンウワバ(Autographa nigrisigna)、イラクサギンウワバ(Trichoplusia ni)、オオタバコガ(Helicoverpa armigera)、タバコガ(Helicoverpa assulta)、ヨトウガ(Mamestra brassicae)、アワヨトウ(Mythimna separata)、フタオビコヤガ(Naranga aenescens)、シロイチモジヨトウ(Spodoptera exigua)、ハスモンヨトウ(Spodoptera litura)、コットンボールワーム(Helicoverpa zea)、タバコバッドワーム(Heliothis virescens)、コットンリーフワーム(Spodoptera littoralis)、ツマジロクサヨトウ(Spodoptera frugiperda)、サザンアーミーワーム(Spodoptera eridania)、タバコホーンワーム(Manduca sexta)、グレープベリーモス(Endopiza viteana)、ワタアカミムシ(Pectinophora gossypiella)、コドリンガ(Cydia pomonella)、ヨーロピアンコーンボーラー(Ostrinia nubilalis)、ソイビーンルーパー(Pseudoplusia includens)等のチョウ目害虫、ドウガネブイブイ(Anomala cuprea)、ヒメコガネ(Anomala rufocuprea)、マメコガネ(Popillia japonica)、カンシャクシコメツキ(Melanotus tamsuyensis)、ヒメマルカツオブシムシ(Anthrenus verbasci)、ニジュウヤホシテントウ(Henosepilachna vigintioctopunctata)、チャイロコメノゴミムシダマシ(Tenebrio molitor)、コクヌストモドキ(Tribolium castaneum)、ゴマダラカミキリ(Anoplophora malasiaca)、マツノマダラカミキリ(Monochamus alternatus endai)、アズキゾウムシ(Callosobruchus chinensis）、ウリハムシ(Aulacophora femoralis)、キスジノミハムシ(Phyllotreta striolata)、アリモドキゾウムシ(Cylas formicarius)、クリシギゾウムシ(Curculio sikkimensis)、イネミズゾウムシ(Lissorhoptrus oryzophilus)、コクゾウムシ(Sitophilus zeamais)、シバオサゾウムシ(Sphenophorus venatus vestius)、ワタミハナゾウムシ(Anthonomus grandis)、モモチョッキリ(Rhynchites heros)、タバコシバンムシ(Lasioderma serricorne)、ヒメヒラタケシキスイ(Epuraea domina)、イネドロオイムシ(Oulema oryzae)、アルファルファタコゾウムシ(Hypera postica)、コロラドハムシ(Lepinotarsa decemlineata)、グラナリアコクゾウムシ(Sitophilus granarius)、ジュウイチホシウリハムシ(Diabrotica undecimpunctata)、ウエスタンコーンルートワーム(Diabrotica virgifera virgifera)、ノーザンコーンルートワーム(Diabrotica longicormis barberi)、アオバアリガタハネカクシ(Paederus fuscipes)等のコウチュウ目害虫、フタテンヒメヨコバイ(Arboridia apicalis）、フタテンオオヨコバイ(Epiacanthus stramineus)、チャノミドリヒメヨコバイ(Empoasca onukii)、ツマグロヨコバイ(Nephotettix cincticeps)、ヒメトビウンカ(Laodelphax striatella)、トビイロウンカ(Nilaparvata lugens)、セジロウンカ(Sogatella furcifera)、ミカンキジラミ(Diaphorina citri)、ワタアブラムシ(Aphis gossypii)、ユキヤナギアブラムシ(Aphis spiraecola)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、ダイコンアブラムシ(Brevicoryne brassicae)、リンゴワタムシ(Eriosoma lanigerum)、モモアカアブラムシ(Myzus persicae)、ムギクビレアブラムシ(Rhopalosiphum padi)、タバココナジラミ(Bemisia tabaci)、オンシツコナジラミ(Trialeurodes vaporariorum)、クワコナカイガラムシ(Pseudococcus comstocki)、ツノロウムシ(Ceroplastes ceriferus)、ルビーロウムシ(Ceroplastes rubens)、イネホソミドリカスミカメ(Trigonotylus caelestialium)、ナシグンバイ(Stephanitis nashi)、オオトゲシラホシカメムシ(Eysarcoris lewisi)、シラホシカメムシ(Eysarcoris ventralis)、チャバネアオカメムシ(Plautia crossota stali)、クモヘリカメムシ(Leptocorisa chinensis)、ホソヘリカメムシ(Riptortus clavatus)、ナガメ(Eurydema rugosa)、クサギカメムシ(Halyomorpha halys)、ミナミアオカメムシ(Nezara viridula)、コバネヒョウタンナガカメムシ(Togo hemipterus)、ジャガイモヒメヨコバイ(Empoasca fabae)、ミカンコナジラミ(Dialeurodes citri)、イセリアカイガラムシ(Icerya purchasi)、ヤノネカイガラムシ(Unaspis yanonensis)、ミカントゲコナジラミ(Aleurocanthus spiniferus)、トコジラミ(Cimex lectularius)等のカメムシ目害虫、ヒラズハナアザミウマ(Frankliniella intonsa)、ミカンキイロアザミウマ(Frankliniella occidentalis)、チャノキイロアザミウマ(Scirtothrips dorsalis)、ミナミキイロアザミウマ(Thrips palmi)、ネギアザミウマ(Thrips tabaci)等のアザミウマ目害虫、ミカンコミバエ(Bactrocera dorsalis)、ウリミバエ(Bactrocera cucurbitae)、チチュウカイミバエ(Ceratitis capitata)、マメハモグリバエ(Liriomyza trifolii)、ナモグリバエ(Chromatomyia horticola)、トマトハモグリバエ(Liriomyza sativae)、タネバエ(Delia platura)、タマネギバエ（Delia antiqua）、リンゴミバエ(Rhagoletis pomonella)、ヘシアンバエ(Mayetiola destructor)、イエバエ(Musca domestica)、サシバエ(Stomoxys calcitrans)、ヒツジシラミバエ(Melophagus ovinus)、キスジウシバエ(Hypoderma lineatum)、ウシバエ(Hypoderma bovis)、ヒツジバエ(Oestrus ovis)、ツェツェバエの一種(Glossina palpalis、Glossina morsitans)、キアシオオブユ(Prosimulium yezoensis)、ウシアブ(Tabanus trigonus)、オオチョウバエ(Telmatoscopus albipunctatus)、トクナガヌカカ(Leptoconops nipponensis)、アカイエカ(Culex pipiens pallens)、ヒトスジシマカ(Aedes albopicutus)、ネッタイシマカ(Aedes aegypti)、シナハマダラカ(Anopheles hyracanus sinesis)等のハエ目害虫、クリハバチ(Apethymus kuri)、カブラハバチ(Athalia rosae ruficornis)、マツノキハバチ(Neodiprion sertifer)、クリタマバチ（Dryocosmus kuriphilus)、グンタイアリ(Eciton burchelli, Eciton schmitti)、クロオオアリ(Camponotus japonicus)、オオスズメバチ(Vespa mandarina japonica)、ブルドックアント(Myrmecia spp.)、ヒアリ類(Solenopsis spp.)、イエヒメアリ(Monomorium pharaonis)等のハチ目害虫、クロゴキブリ(Periplaneta fuliginosa)、ヤマトゴキブリ(Periplaneta japonica)、チャバネゴキブリ(Blattella germanica)等のゴキブリ目害虫、エンマコオロギ(Teleogryllus emma)、ケラ(Gryllotalpa orientalis)、トノサマバッタ(Locusta migratoria)、コバネイナゴ(Oxya yezoensis)、サバクワタリバッタ(Schistocerca gregaria)等のバッタ目害虫、イエシロアリ(Coptotermes formosanus)、ヤマトシロアリ(Reticulitermes speratus)、タイワンシロアリ(Odontotermes formosanus)等のシロアリ目害虫、ネコノミ(Ctenocephalidae felis)、ヒトノミ(Pulex irritans)、ケオプスネズミノミ(Xenopsylla cheopis)等のノミ目害虫、ニワトリオオハジラミ(Menacanthus stramineus)、ウシハジラミ(Damalinia bovis)等のハジラミ目害虫、ウシジラミ(Haematopinus eurysternus)、ウシホソジラミ(Linognathus vituli)、ケブカウシジラミ(Solenopotes capillatus)等のシラミ目害虫。ダニ目としては、ミカンハダニ(Panonychus citri)、リンゴハダニ(Panonychus ulmi)、カンザワハダニ(Tetranychus kanzawai)、ナミハダニ(Tetranychus urticae)等のハダニ類、チューリップサビダニ(Aceria tulipae)、トマトサビダニ(Aculops lycopersici)、ミカンサビダニ(Aculops pelekassi)等のフシダニ類、ロビンネダニ(Rhizoglyphus robini)、ホウレンソウケナガコナダニ(Tyrophagus similis）等のコナダニ類、チャノホコリダニ(Polyphagotarsonemus latus)等のホコリダニ類、ミツバチヘギイタダニ(Varroa jacobsoni, Varroa destructor)等のハチダニ類、オウシマダニ(Boophilus microplus)、フタトゲチマダニ(Haemaphysalis longicornis)等のマダニ類、ヒツジキュウセンヒゼンダニ(Psoroptes ovis)等のキュウセンダニ類、ヒゼンダニ(Sarcoptes scabiei)等のヒゼンダニ類等。その他、オカダンゴムシ(Armadillidium vulgare)等の甲殻類、サツマイモネコブセンチュウ(Meloidogyne incognita)、キタネコブセンチュウ(Meloidogyne hapla)、ジャガイモシストセンチュウ(Globodera rostochiensis)、ダイズシストセンチュウ(Heterodera glycines）、キタネグサレセンチュウ(Prathylenchus penetrans)、クルミネグサレセンチュウ(Prathylenchus vulnus)、イネシンガレセンチュウ(Aphelenchoides besseyi)、マツノザイセンチュウ(Bursaphelenchus xylophilus)等のセンチュウ類、スクミリンゴガイ(Ponacea canaliculata)、ナメクジ(Meghimatium bilineata)、ウスカワマイマイ(Acusta despecta sieboldiana)、チャコウラナメクジ(Lehmannina valentiana）等の軟体動物等を挙げることができる。 Examples of pests and mites include, for example, Cossus insularis, Adoxophyes honmai, Adoxophyes orana faciata, Nashihimeshini (Grapholita molesta), Chamonakisuna (Homona magnamina) Leguminivora glycinivorella), Ginmon leafworm (Lyonetia prunifoliella malinella), Chanohosuga (Caloptilia theivora), Butterberry leafworm (Phyllonorycter ringoniella), Citrus leaflet (Phyllocnistis citrella), Negikoga (Acrol) conjugella), Grape squirrel (Nokona regalis), Cosca squirrel (Synanthedon hector), Oyster moth (Stathmopoda masinissa), Peach moth (Carposina sasakii), Iraga (Monema flavescens), Nikaameiga (Chilo supcroscis), Hellula undalis, Ostrinia furnacalis, Shibata toga (Parapediasia teterrella), Ephestia kuehniella, vortica (Papi) (Parnara guttata), mugwort duck (Ascotis selenaria), shrimp squirrel (Agrius convolvuli), white-spotted squirrel (Orgyia thyellina), white-spotted starfish (Hyphantria cunea), Tamanayagai (Agrotis ipaum), grotis , Nettle moth (Trichoplusia ni), giant moth (Helicoverpa armigera), tobacco moth (Helicoverpa assulta), sweet potato (Mamestra brassicae), common scallop (Mythimna separata), Futhobiko moth (Naranga anescens), moth Spodoptera litura, Cotton ball worm (Helicoverpa zea), Tobacco bad worm (Heliothis virescens), Cotton leaf worm (Spodoptera littoralis), Spodoptera frugiperda, Southern army worm (Spodoptera hornid worm) (Manduca sexta), Grapeberry moss (Endopiza viteana), Cotton beetle (Pectinophora gossypiella), Codling moth (Cydia pomonella), European corn borer (Ostrinia nubilalis), Soi bean looper (Pseudoplusia includeala) , Anomala rufocuprea, Bean squirrel (Popillia japonica), Japanese horned beetle (Melanotus su tamsuyensis), Japanese beetle (Anthrenus 、 verbasci), Henosepilachna to vigintioctobrata Ntomodokuki (Tribolium castaneum), Japanese beetle beetle (Anoplophora malasiaca), Japanese pine beetle (Monochamus alternatus endi), Azuki beetle (Callosobruchus chinensis), Urihamushi (Aulacophora femoralis), Kisojiri (Currculio Poppy squirrel (Epuraea domina), rice plant beetle (Oulema oryzae), alfalfa weevil (Hypera postica), Colorado beetle (Lepinotarsa decemlineata), granary weevil (Sitophilus granarius) Coleoptera pests such as deer (Diabrotica undecimpunctata), western corn root worm (Diabrotica virgifera virgifera), northern corn root worm (Diabrotica longicormis barberi), and the like Green leafhopper (Epiacanthus stramineus), Chinese green leafhopper (Empoasca onukii), Green leafhopper (Nephotettix cincticeps), Yellow leafhopper (Laodelphax striatella), Yellow leafhopper (Nilaparvata lugens) gossypii), Aphis spiraecola, potato aphid (Aulacorthum solani), radish aphid (Brevicoryne brassicae), apple rotifer (Eriosoma lanigerum), peach aphid (Myzus persicae), wheat Aphid (Rhopalosiphum padi), Tobacco whitefly (Bemisia tabaci), Onittsu whitefly (Trialeurodes vaporariorum), Scots beetle (Pseudococcusstockcomstocki), Rotifers (Ceroplastes ceriferus), Ruby moths (ens) Stephanitis nashi), Japanese beetle (Eysarcoris lewisi), Shirahoshi beetle (Eysarcoris ventralis), Chabae stink bug (Plautia crossota stali), Spider helicopter (Leptocorisa chinensis), tus , Haryomorpha halys, Nezara viridula, Togo hemipterus, Empoasca fabae, Dialeurodes ciria , Scarabaeidae (Unaspis yanonensis), citrus white lice (Aleurocanthus spiniferus), stink bugs (Cimex lectularius), etc. Thrips palmi, Thrips tabaci, etc., Thrips tabaci , Tomato leaf fly (Liriomyza sativae), red fly (Delia platura), onion fly (Delia antiqua), ring fly (Rhagoletis pomonella), fly fly (Mayetiola destructor), house fly (Musca domestica), sand flies (calcium calculi) White flies (Melophagus ovinus), Hypoderma lineatum, Bullflies (Hypoderma bovis), Swallow flies (Oestrus ovis), Tsetse flies (Glossina Telmatoscopus albipunctatus), Toepanakanuka (Leptoconops nipponensis), Culex pipipiens ヒ ト pallens, Aedes albopicutus, Aedes aegypsin rosae ruficornis), pine bee (Neodiprion sertifer), bee (Dryocosmus kuriphilus), gunt ant (Eciton burchelli, Eciton schmitti), black ant (Camponotus japonicus), giant ant bee (Solenopsis spp.), Bee moths (Monomorium pharaonis), etc. Gryllotalpa Termite pests, cat fleas (Ctenocephalidae felis), human fleas (Pulex irritans), flea fleas such as Xenopsylla cheopis, chicken lice (Menacanthus (Haematopinus eurysternus) Mi (Linognathus vituli), Kebukaushijirami (Solenopotes capillatus) Anoplura pests such as. As for the mite, spider mites (Panonychus citri), apple spider mites (Panonychus ulmi), Kanzawa spider mites (Tetranychus kanzawai), spider mite (Tetranychus urticae) and other spider mites, Tulip spider mites (Aceria Aculops pelekassi, etc., Robin tick (Rhizoglyphus robini), Spinach mite (Tyrophagus similis), Dust mites (Polyphagotarsonemus latus), etc. Ticks, such as ticks (Boophilus microplus), ticks (Haemaphysalis longicornis), cucumber ticks (Psoroptes ovis), sword mites (Sarcoptes scabiei), etc. Other crustaceans such as Armadillidium vulgare, sweet potato root nematode (Meloidogyne incognita), fox root nematode (Meloidogyne hapla), potato cyst nematode (Globodera rostochiensis) (Heterodera , Nematodes (Ponacea canaliculata), slug apple moth (Ponacea canaliculata), slug apple moth (Meghimat cus ), And mollusks such as Lehmannina iana valentiana.
［有害生物防除剤］
　本発明の農園芸用の有害生物防除剤は、特に、殺菌効果および殺虫効果が顕著であり、式［Ｉ］で示される化合物の１種若しくは２種以上を有効成分として含有するものである。 [Pesticides]
The agricultural and horticultural pest control agent of the present invention is particularly effective in sterilizing effect and insecticidal effect, and contains one or more compounds represented by the formula [I] as active ingredients.
　式［Ｉ］で示される本発明化合物の適用は植物に対して、有効成分を、噴霧、散布、塗布等して処理するか、または植物の種子、または植物の周囲の土壌あるいは種子を播種する土壌、水田、水耕栽培の水を有効成分で処理することにより行うことができる。殺菌剤として使用する場合、適用は植物が病原菌に感染する前または感染後に行うことができる。殺虫剤として使用する場合、適用は害虫などが発生する前に、または発生後に行うことが出来る。 The compound of the present invention represented by the formula [I] is applied to the plant by spraying, spraying, applying, or the like with the active ingredient, or sowing the seed of the plant or the soil or seed around the plant. It can be performed by treating soil, paddy field, hydroponics water with active ingredients. When used as a fungicide, the application can be done before or after the plant is infected with the pathogen. When used as an insecticide, application can be performed before or after the occurrence of pests.
　本化合物は通常の製剤の様態、例えば、粒剤、粉粒剤、水溶剤、油剤、エマルション製剤、マイクロエマルション製剤、サスポエマルション製剤、液剤、水和剤、乳剤、懸濁剤、錠剤、顆粒水和剤、マイクロカプセル、エアロゾル、ペースト剤、ジャンボ剤、粉剤、燻煙剤、燻蒸剤などのような農園芸用有害生物防除剤に適する薬剤として使用することができる。このような態様は、少なくとも一種の本発明化合物と適当な固体または液体の担体類、及び所望により、有効成分の分散性や、他の性質の改善のために適当な補助剤（例えば、界面活性剤、溶剤、安定剤）とともに混合する通常の方法によって得ることができる。 This compound is in the form of normal preparations such as granules, powders, aqueous solvents, oils, emulsions, microemulsions, suspoemulsions, solutions, wettable powders, emulsions, suspensions, tablets, granules It can be used as an agent suitable for agricultural and horticultural pest control agents such as wettable powders, microcapsules, aerosols, pastes, jumbo agents, powders, smoke agents, fumigants and the like. Such embodiments include at least one compound of the invention and a suitable solid or liquid carrier, and, if desired, suitable adjuvants (eg, surfactants) to improve the dispersibility of the active ingredient and other properties. Can be obtained by an ordinary method of mixing with an agent, a solvent and a stabilizer.
　固体の担体、または希釈剤の例としては、植物性物質（例えば、結晶性セルロース、デンプン、木粉、コルク、コーヒー殻等）、繊維状物質、人工の可塑性粉末、粘土（例えば、カオリン、ベントナイト、白土、珪藻土、合成含水酸化珪素、フバサミクレー、酸性白土等）、タルク及び無機物（例えば、バーミュライト、モンモリロナイト、軽石、硫黄粉末、リン灰石、雲母、セリサイト、石英粉末、活性炭、炭酸カルシウム等）、高分子化合物（ポリ塩化ビニル、石油樹脂等）、化学肥料（例えば、硫安、燐安、硝安、塩安、塩化カルシウム、尿素等）などがある。液体の担体類及び希釈剤としては、水、アルコール類（例えば、メタノール、エタノール、イソプロパノール、シクロヘキサノール等）、ケトン類（例えば、アセトン、メチルエチルケトン、シクロヘキサノン等）、エーテル類（例えば、エチルセロソルブ、ブチルセロソルブ、ジオキサン等）、芳香族炭化水素（例えば、ベンゼン、トルエン、キシレン、エチルベンゼン、メチルナフタレン等）、脂肪族炭化水素（例えば、ケロシン、パラフィン等）、エスエル類（例えば、酢酸イソプロピル、酢酸ベンジル等）、ニトリル類、アミド類（例えば、Ｎ，Ｎ－ジメチルホルムアミド、ジメチルスルホキシドなど）、ハロゲン化炭化水素（例えば、クロロベンゼン、トリクロロエチレン）などがある。 Examples of solid carriers or diluents include plant materials (eg, crystalline cellulose, starch, wood flour, cork, coffee husk, etc.), fibrous materials, artificial plastic powders, clays (eg, kaolin, bentonite) , White clay, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, acid clay, etc., talc and minerals (eg, vermulite, montmorillonite, pumice, sulfur powder, apatite, mica, sericite, quartz powder, activated carbon, calcium carbonate Etc.), polymer compounds (polyvinyl chloride, petroleum resins, etc.), chemical fertilizers (eg, ammonium sulfate, phosphorous acid, ammonium nitrate, ammonium chloride, calcium chloride, urea, etc.). Liquid carriers and diluents include water, alcohols (eg, methanol, ethanol, isopropanol, cyclohexanol, etc.), ketones (eg, acetone, methyl ethyl ketone, cyclohexanone, etc.), ethers (eg, ethyl cellosolve, butyl cellosolve) , Dioxane, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (eg, kerosene, paraffin, etc.), and swells (eg, isopropyl acetate, benzyl acetate, etc.) Nitriles, amides (eg, N, N-dimethylformamide, dimethyl sulfoxide, etc.), halogenated hydrocarbons (eg, chlorobenzene, trichloroethylene), and the like.
　ガス状担体、すなわち噴射剤としては、例えば炭酸ガス、ブタンガス、フルオロカーボンなどが挙げられる。 Examples of gaseous carriers, ie, propellants, include carbon dioxide gas, butane gas, and fluorocarbon.
　界面活性剤の例としては、従来より農薬製剤分野において使用されている種々のアニオン性界面活性剤、非イオン性界面活性剤等が挙げられる。アニオン性界面活性剤としては、例えば、アルキルスルホン酸、アルファオレフィンスルホン酸、リグニンスルホン酸、アルキルベンゼンスルホン酸、アルキルナフタレンスルホン酸、ナフタレンスルホン酸ホルマリン縮合物、ジアルキルスルホサクシネート等のスルホン酸系界面活性剤およびそれらの塩、ポリオキシエチレンアルキルエーテルサルフェート、ポリオキシエチレンアルキルアリルエーテルサルフェート、ポリオキシエチレンスチリルフェニルエーテルサルフェート、ポリオキシエチレンフェニルアルキルアリルエーテルサルフェート、ポリオキシアルキレングリコールサルフェート、高級アルコールサルフェート、脂肪酸エステルサルフェート、フェニルフェノール（ＥＯ）硫酸塩等のサルフェート系界面活性剤およびそれらの塩、ポリオキシエチレンアルキルエーテルホスフェート、ポリオキシエチレンアルキルアリルホスフェート、フェニルフェノール（ＥＯ）リン酸エステル塩、ポリオキシエチレンフェニルアルキルアリルエーテルホスフェート、高級アルコールホスフェート、ポリオキシエチレントリベンジルフェノールホスフェート等のホスフェート系界面活性剤およびそれらの塩、高級脂肪酸塩、ポリカルボン酸型界面活性剤およびそれらの塩等を挙げることができる。上記各界面活性剤におけるそれらの塩としては、ナトリウム、カリウム、マグネシウム、カルシウム、アンモニウム、エタノールアミン、ジエタノールアミン、トリエタノールアミン、種々のアミン類等の塩が含まれる。非イオン性界面活性剤としては、例えば、ポリオキシエチレンアルキルアリルエーテル、ポリオキシエチレンスチリルフェニルエーテル、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンフェニルアルキルアリルエーテル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレングリコール、ポリオキシエチレンアルキルエステル、ポリオキシエチレンポリオキシプロピレンブロックコポリマー、ポリオキシアルキレングリコール、アルキンジオール（アセチレングリコール）、アルキニレンポリオキシエチレンジオール、ソルビタン脂肪酸エステル、アルキルアリールエーテルホルマリン縮合物等を挙げることができる。 Examples of surfactants include various anionic surfactants and nonionic surfactants conventionally used in the field of agrochemical formulations. Examples of the anionic surfactant include sulfonic acid-based surfactants such as alkyl sulfonic acid, alpha olefin sulfonic acid, lignin sulfonic acid, alkylbenzene sulfonic acid, alkyl naphthalene sulfonic acid, naphthalene sulfonic acid formalin condensate, and dialkyl sulfosuccinate. Agents and salts thereof, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl allyl ether sulfate, polyoxyethylene styryl phenyl ether sulfate, polyoxyethylene phenyl alkyl allyl ether sulfate, polyoxyalkylene glycol sulfate, higher alcohol sulfate, fatty acid ester Sulfate surfactants such as sulfate and phenylphenol (EO) sulfate and the like Salts of polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl allyl phosphate, phenylphenol (EO) phosphate ester salt, polyoxyethylene phenyl alkyl allyl ether phosphate, higher alcohol phosphate, polyoxyethylene tribenzylphenol phosphate, etc. Surfactants and salts thereof, higher fatty acid salts, polycarboxylic acid type surfactants and salts thereof, and the like. The salts in the above surfactants include salts of sodium, potassium, magnesium, calcium, ammonium, ethanolamine, diethanolamine, triethanolamine, various amines and the like. Examples of the nonionic surfactant include polyoxyethylene alkyl allyl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene alkyl ether, polyoxyethylene phenyl alkyl allyl ether, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycol. , Polyoxyethylene alkyl ester, polyoxyethylene polyoxypropylene block copolymer, polyoxyalkylene glycol, alkyne diol (acetylene glycol), alkynylene polyoxyethylene diol, sorbitan fatty acid ester, alkyl aryl ether formalin condensate, etc. it can.
　安定剤としては、イソプロピルリン酸塩混合物、燐酸トリクレジル、トルー油、エポキシ油、界面活性剤類、脂肪酸類およびそのエステル類が挙げられる。上記の成分に加えて、本発明の化合物は他の殺菌剤、殺虫剤、除草剤、または肥料と混合して製剤することができる。 Stabilizers include isopropyl phosphate mixture, tricresyl phosphate, true oil, epoxy oil, surfactants, fatty acids and esters thereof. In addition to the above components, the compounds of the present invention can be formulated in admixture with other fungicides, insecticides, herbicides, or fertilizers.
　一般に、上記製剤は、少なくとも一種の本発明化合物［Ｉ］を、１～９５重量％、好ましくは１～５０重量％含む。これらの製剤は単独でまたは希釈して使用することができ、本発明の化合物［Ｉ］を約１ｇ～５ｋｇ／ヘクタール、好ましくは約２ｇ～１００ｇ／ヘクタールを、通常約１～５００００ｐｐｍ、好ましくは約５０～１０００ｐｐｍの濃度で使用する。 Generally, the above-mentioned preparation contains 1 to 95% by weight, preferably 1 to 50% by weight, of at least one compound [I] of the present invention. These preparations can be used alone or diluted, and the compound [I] of the present invention is used in an amount of about 1 to 5 kg / ha, preferably about 2 to 100 g / ha, usually about 1 to 50000 ppm, preferably about Used at a concentration of 50-1000 ppm.
　式［Ｉ］で示される本発明化合物は、単独あるいはその製剤物として使用することもできるが、殺菌・殺カビ剤、殺バクテリア剤、殺ダニ剤、殺線虫剤、殺虫剤、生物農薬、除草剤、植物ホルモン剤、植物発育調節物質、共力剤、誘引剤、忌避剤、色素、肥料等との混合物または、それらの有効成分から選択される１種又は２種以上を組み合わせた混合物の製剤物を有害生物防除剤として使用することもできる。そこでは作用、防除対象病害虫、使用適期の拡大、或いは薬量の低減、相乗効果を図ること、もしくは抵抗力の発達を妨げることなどが期待でき、多くの場合、混合物の活性は個別の活性をしのぎ、共同成分との協力的薬効が達成される。 The compound of the present invention represented by the formula [I] can be used alone or as a preparation thereof, but a bactericidal / fungicidal agent, bactericidal agent, acaricide, nematicide, insecticide, biological pesticide, A mixture of herbicides, plant hormones, plant growth regulators, synergists, attractants, repellents, pigments, fertilizers, etc., or a mixture of one or more selected from those active ingredients The preparation can also be used as a pest control agent. There, it can be expected that the action, pests to be controlled, expansion of the appropriate period of use, or reduction of dosage, synergistic effect, or prevention of development of resistance, etc. Shinogi, cooperative medicinal effects with joint ingredients are achieved.
　混合物中の共同成分のうち、殺菌・殺カビ剤、殺バクテリア剤、殺虫、殺ダニ剤、殺線虫剤、生物農薬、フェロモン剤、天然殺菌剤、天然殺虫剤の多くは開発され市販されているか、または日本植物防疫協会発行の農薬ハンドブック(２０１１年)、同協会発行の農薬要覧（２０１１年）、全国農業協同組合連合会発行のクミアイ農薬総覧(２０１１年)及び同連合会発行のＳＨＩＢＵＹＡ　ＩＮＤＥＸ(２０１１年)などで知られている。 Of the joint ingredients in the mixture, many of the fungicides and fungicides, bactericides, insecticides, acaricides, nematicides, biopesticides, pheromones, natural fungicides, and natural insecticides have been developed and marketed. Pesticide Handbook (2011) published by the Japan Plant Protection Association, Agricultural Handbook (2011), Kumiai Agricultural Guidebook (2011) published by the National Federation of Agricultural Cooperatives, and SHIBUYA INDEX published by the Federation (2011).
　下記に例を示すが、これらに限定されるものではない。 Examples are shown below, but are not limited thereto.
　殺菌剤の例としては、SH基酵素阻害活性化合物、核酸合成阻害活性化合物、紡錘糸形成阻害活性化合物、ベンズアニリド系化合物、ストロビルリン系化合物、その他電子伝達系阻害活性化合物、アミノ酸合成阻害活性化合物、ステロール生合成阻害活性化合物、シグナル情報伝達阻害活性化合物、脂質合成阻害活性化合物、細胞壁生合成阻害活性化合物、メラニン合成阻害活性化合物、宿主抵抗誘導性化合物、その他のあるいは未明な作用を有する化合物等を挙げることができる。 Examples of bactericides include SH group enzyme inhibitory compounds, nucleic acid synthesis inhibitory active compounds, spindle yarn formation inhibitory active compounds, benzanilide compounds, strobilurin compounds, other electron transport inhibitory compounds, amino acid synthesis inhibitory active compounds, sterols Biosynthesis inhibitory active compounds, signal signal transduction inhibitory active compounds, lipid synthesis inhibitory active compounds, cell wall biosynthesis inhibitory active compounds, melanin synthesis inhibitory active compounds, host resistance-inducing compounds, other compounds with unclear effects, etc. be able to.
　SH基酵素阻害活性化合物：クロロタロニル(chlorothalonil)、ジチアノン(dithianon)、キャプタン(captan)、フォルペット(folpet)、イミノクタジン・アルベシル酸塩(iminoctadine-albesilate)、イミノクタジン酢酸塩(iminoctadine-triacetate)、ファーバム(ferbam)、ナーバム(nabam)、マンゼブ(mancozeb)、マンネブ(maneb)、メチラム(metiram)、プロピネブ(propineb)、ポリカーバメート(polycarbamate)、チウラム(thiram)、ジネブ(zineb)、ジラム(ziram)、酸化第二銅(cupric oxide)、水酸化第二銅(copper hydroxide)、塩基性塩化銅(Copper oxychloride)、無水硫酸銅(Copper sulfate (anhydride))、硫酸銅(copper sulfate)、硫黄(sulphur)等。 SH group enzyme inhibitory active compounds: chlorothalonil, dithianon, captan, folpet, iminoctadine-albesilate, iminoctadine-triacetate, farbum ( ferbam), nabam, mancozeb, manneb, maneb, metiram, propineb, polycarbamate, thiram, zineb, ziram, oxidation Cupric oxide, cupric hydroxide, basic copper oxychloride, anhydrous copper sulfate (copper oppsulfate (anhydride)), copper sulfate (copper sulfate), sulfur, etc. .
　核酸合成阻害活性化合物：メタラキシル(metalaxyl)、メタラキシル・M(metalaxyl-M)、オキサジキシル(oxadixyl)、ブピリメート(bupirimate)、ヒメキサゾール(hymexazol)、オキソニック酸(oxolinic acid)等。 Nucleic acid synthesis inhibitory active compounds: metalaxyl, metalaxyl-M, oxadixyl, bupirimate, hymexazol, oxolinic acid, etc.
　紡錘糸形成阻害活性化合物：ベノミル(benomyl)、カルベンダジム(carbendazim)、チオファネートメチル(thiophanate-methyl)、ジエトフェンカルブ(diethofencarb)、ゾキサミド(zoxamide)、ペンシクロン(pencycuron)、フルオピコリド(fluopicolide)等。 Spindle yarn formation inhibitory active compounds: benomyl, carbendazim, thiophanate-methyl, dietofencarb, zoxamide, pencycuron, fluopicolide and the like.
　ベンズアニリド系化合物：フルトラニル(flutolanil)、メプロニル(mepronil)、フルオピラム(fluopyram)、カルボキシン(carboxin)、オキシカルボキシン(oxycarboxin)、チフルザミド(thifluzamide)、ビキサフェン(bixafen)、フルキサピロキサド(fluxapyroxad)、フラメトピル(furametpyr)、イソピラザム(isopyrazam)、ペンフルフェン(penflufen)、ペンチオピラド(penthiopyrad)、セダキサン(sedaxane)、ボスカリド(boscalid)等。 Benzanilide compounds: flutolanil, mepronil, fluopyram, carboxin, oxycarboxin, thifluzamide, bixafen, fluxapyroxad, Furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid and the like.
　ストロビルリン系化合物：アゾキシストロビン(azoxystrobin)、ピコキシストロビン(picoxystrobin)、ピラオキシストロビン(pyraoxystrobin)、ピラクロストロビン(pyraclostrobin)、ピラメトストロビン(pyrametostrobin)、クレソキシムメチル(kresoxim-methyl)、トリフロキシストロビン(trifloxystrobin)、ジモキシストロビン(dimoxystrobin)、メトミノストロビン(metominostrobin)、オリサストロビン(orysastrobin)、ファモキサドン(famoxadone)、フェナミドン(fenamidone)、ピリベンカルブ(pyribencarb)等。 Stravylline compounds: azoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, kresoxim-methyl, trif Roxystrobin, dimoxystrobin, metominostrobin, orysastrobin, famoxadone, fenamidone, pyribencarb, etc.
　その他電子伝達系阻害活性化合物：ジフルメトリム(diflumetorim)、シアゾファミド(cyazofamid)、アミスルブロム(amisulbrom)、メプチルディノキャップ(meptyldinocap)、フルアジナム(fluazinam)、フェリムゾン(ferimzone)、シルチオファム(silthiofam)、アメトクトラジン(ametoctradin)等。 Other compounds that inhibit electron transport system: diflumetorim, cyazofamid, amisulbrom, meptyldinocap, fluazinam, ferimzone, silthiofam, amethoctrazine etc.
　アミノ酸合成阻害活性化合物：シプロジニル(cyprodinil)、メパニピリム(mepanipyrim)、ピリメタニル(pyrimethanil)、ブラストサイジン・S(blasticidin-S)、カスガマイシン(kasugamycin)、ストレプトマイシン(streptomycin)、オキシテトラサイクリン(oxytetracycline)等。 Amino acid synthesis inhibitory active compounds: cyprodinil, mepanipyrim, pyrimethanil, blasticidin-S, kasugamycin, streptomycin, oxytetracycline, and the like.
　ステロール生合成阻害活性化合物：フェナリモル(fenarimol)、イマザリル(imazalil)、オキスポコナゾール(oxpoconazole)、ペフラゾエート(pefurazoate)、プロクロラズ(prochloraz)、トリフルミゾール(triflumizole)、アザコナゾール(azaconazole)、ビテルタノール(bitertanol)、ブロムコナゾール(bromuconazole)、シプロコナゾール(cyproconazole)、ジフェノコナゾール(difenoconazole)、エポキシコナゾール(epoxiconazole)、フェンブコナゾール(fenbuconazole)、フルトリアフォル(flutriafol)、ヘキサコナゾール(hexaconazole)、イミベンコナゾール(imibenconazole)、メトコナゾール(metoconazole)、ミクロブタニル(myclobutanil)、ペンコナゾール(penconazole)、プロピコナゾール(propiconazole)、シメコナゾール(simeconazole)、テブコナゾール(tebuconazole)、テトラコナゾール(tetraconazole)、トリアジメホン(triadimefon)、トリアジメノール(triadimenol)、トリチコナゾール(triticonazole)、フェンプロピモルフ(fenpropimorph)、トリデモルフ(tridemorph)、ピペラリン(piperalin)、スピロキサミン(spiroxamine)、フェンヘキサミド(fenhexamid)、ピリブチカルブ(pyributicarb)、ナフチフィン(naftifine)、テルビナフィン(terbinafine)等。 Sterol biosynthesis inhibiting active compounds: fenarimol, imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole, azaconazole, bitertanol ), Bromuconazole, cyproconazole, difenoconazole, epoxiconazole, fenbuconazole, flutriafol, hexaconazole, imicon Benconazole (imibenconazole), Metoconazole (metoconazole), Microbutanil (myclobutanil), Penconazole (propconazole), Cimeconazole (simeconazole), Tebuconazole (tebuconazole), Tetraconazole (triconon), Triimmephone (triimon) G Adimenol, triticonazole, fenpropimorph, tridemorph, piperalin, spiroxamine, fenhexamid, pyributicarb, naphthifine Terbinafine, etc.
　シグナル情報伝達阻害活性化合物：キノキシフェン(quinoxyfen)、プロキナジド(proquinazid)、フルジオキソニル(fludioxonil)、イプロジオン(iprodione）、プロシミドン(procymidone)、ビンクロゾリン(vinclozolin)、ミクロゾリン(myclozolin)等。 Signal signal transduction inhibitory compounds: quinoxyfen, proquinazid, fludioxonil, iprodione, procymidone, vinclozolin, microzoline, etc.
　脂質合成阻害活性化合物：イプロベンホス(iprobenfos)、イソプロチオラン(isoprothiolane)、キントゼン(quintozene)、プロパモカルブ(propamocarb)、プロチオカルブ(prothicarb)等。 Lipid synthesis inhibitory active compounds: iprobenfos, isoprothiolane, quintozene, propamocarb, prothicarb and the like.
　細胞壁生合成阻害活性化合物：バリダマイシン(validamycin)、ポリオキシンB(polyoxinB)、ジメトモルフ(dimethomorph)、ベンチアバリカルブ(benthiavalicarb)、イプロバリカルブ(iprovalicarb)、バリフェナレート(valifenalate)、マンジプロパミド(mandipropamid)等。 Cell wall biosynthesis inhibitory active compounds: validamycin, polyoxin B, dimethomorph, benthiavalicarb, iprovalicarb, valifenalate, mandipropamid, etc.
　メラニン合成阻害活性化合物：ピロキロン(pyroquilon)、トリシクラゾール(tricyclazole)、カルプロパミド(carpropamid)、ジクロシメット(diclocymet)、フェノキサニル(fenoxanil)等。 Melanin synthesis inhibitory active compounds: pyroquilon, tricyclazole, carpropamid, diclocymet, fenoxanil and the like.
　宿主抵抗誘導性化合物：アシベンゾラル・S・メチル(acibenzolar-S-methyl)、プロベナゾール(probenazole)、イソチアニル(isotianil)、ラミナリン(laminarin)等。 Host resistance-inducing compounds: acibenzolar-S-methyl, probenazole, isotianil, laminarin and the like.
　その他のあるいは未明な作用を有する化合物：シモキサニル(cymoxanil)、ホセチルアルミニウム(fosetyl-Al)、トリアゾキシド(triazoxide)、フルスルファミド(flusulfamide)、メタスルホカルブ(methasulfocarb)、エタボキサム(ethaboxam)、シフルフェナミド(cyflufenamid)、メトラフェノン(metrafenone)、ピリオフェノン(pyriofenone)、フルチアニル(flutianil)、フェリムゾン(ferimzone)、キノメチオネート(chinomethionat)、テブフロキン(tebufloquin)、ピリジルアミジン(pyridylamidine)、エネストロブリン(enestroburin)、フルモルフ(flumorph)等。 Other or unclear compounds: cymoxanil, fosetyl-Al, triazoxide, fursulfamide, methasulfocarb, ethaboxam, cyflufenamid, Metrafenone, pyriofenone, flutianil, ferimzone, chinomethionat, tebufloquin, pyridylamidine, enestroburin, flumorph, etc.
　殺虫剤・殺ダニ剤・殺線虫剤の例としては、アセチルコリンエステラーゼ阻害化合物、GABA作用性塩素イオンチャネル阻害化合物、ナトリウムイオンチャネル阻害化合物、ニコチン性アセチルコリン受容体阻害化合物、塩素イオンチャル活性化合物、幼若ホルモン類似化合物、非選択性阻害化合物、同翅目選択的摂食阻害化合物、ダニ類成長阻害化合物、微生物由来昆虫中腸内膜破壊剤、ATP合成阻害化合物、酸化的リン酸化脱共役化合物、ニコチン性アセチルコリン受容体チャネル阻害化合物、キチン生合成阻害化合物、脱皮・変態阻害化合物、オクトパミン受容体作動化合物、電子伝達系阻害化合物、電位依存性ナトリウムチャネル阻害化合物、脂質合成阻害化合物、リアノジンレセプター阻害化合物、その他のあるいは未明な作用を有する化合物、等を挙げることができる。 Examples of insecticides / acaricides / nematicides include acetylcholinesterase inhibitor compounds, GABA-acting chloride channel inhibitor compounds, sodium ion channel inhibitor compounds, nicotinic acetylcholine receptor inhibitor compounds, chloride ion active compounds, Juvenile hormone analogues, non-selective inhibitory compounds, homozygous selective feeding inhibitory compounds, mite growth inhibitory compounds, microorganism-derived insect midgut membrane disruptors, ATP synthesis inhibitory compounds, oxidative phosphorylation uncoupling compounds Nicotinic acetylcholine receptor channel inhibitor compound, chitin biosynthesis inhibitor compound, molting / metamorphosis inhibitor compound, octopamine receptor agonist compound, electron transport system inhibitor compound, voltage-gated sodium channel inhibitor compound, lipid synthesis inhibitor compound, ryanodine receptor inhibitor Compound, other or unclear effects And the like.
　アセチルコリンエステラーゼ阻害化合物：アルジカルブ(aldicarb)、ベンフラカルブ(benfuracarb)、カルバリル(carbaryl)、カルボフラン(carbofuran)、カルボスルファン(carbosulfan)、フェノブカルブ(fenobucarb)、メチオカルブ(methiocarb)、メソミル(methomyl)、オキサミル(oxamyl)、チオジカルブ(thiodicarb)、アセフェート(acephate)、カズサホス(cadusafos)、クロルピリホス(chlorpyrifos)、ダイアジノン(diazinon)、ジクロルボス(dichlorvos)、ジメトエート(dimethoate)、EPN、フェナミホス(fenamiphos)、フェニトロチオン(fenitrothion)、フォスチアゼート(fosthiazate)、イミシアホス(imicyafos)、マラチオン(malathion)、メタミドホス(methamidophos)、モノクロトホス(monocrotophos)、メチルパラチオン(parathion-methyl)、プロフェノフォス(profenofos)、テルブフォス(terbufos)等。 Acetylcholinesterase-inhibiting compounds: aldicarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenobucarb, methiocarb, methomyl, oxamyl ), Thiodicarb, acephate, cadusafos, chlorpyrifos, diazinon, dichlorvos, dimethoate, EPN, fenamiphos, fenitrothion, fenitrothion, fenitrothion (fosthiazate), imacyafos, malathion, methamidophos, monocrotophos, methylthalathion, parafenion, profenofos, terbufos and the like.
　GABA作用性塩素イオンチャネル阻害化合物：エンドスルファン(endosulfan)、エチプロール(ethiprole)、フィプロニル(fipronil)、アセトプロール(acetoprole)等。 GABA-acting chloride ion channel-inhibiting compounds: endosulfan, ethiprole, fipronil, acetoprole and the like.
　ナトリウムイオンチャネル阻害化合物：アクリナトリン(acrinathrin)、アレスリン(allethrin)、ビフェンスリン(bifenthrin)、ラムダ・シハロトリン(lambda-cyhalothrin)、シペルメトリン(cypermethrin)、エトフェンプロックス(ethofenprox)、フェンバレレート(fenvalerate)、パーメスリン(permethrin)、DDT、メトキシクロル(methoxychlor)、テフルトリン(tefluthrin)等。 Sodium ion channel blocking compounds: acrinathrin, allethrin, bifenthrin, lambda-cyhalothrin, cypermethrin, etofenprox, fenvalerate, permethrin (permethrin), DDT, methoxychlor, tefluthrin, etc.
　ニコチン性アセチルコリン受容体阻害化合物：アセタミプリド(acetamiprid)、クロチアニジン(clothianidin)、ジノテフラン(dinotefuran)、イミダクロプリド(imidacloprid)、ニテンピラム(nitenpyram)、チアクロプリド(thiacloprid)、チアメトキサム(thiamethoxam)等。スピネトラム(spinetoram)、スピノサド(spinosad)等。 Nicotinic acetylcholine receptor inhibitory compounds: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, etc. Spinetoram, spinosad, etc.
　塩素イオンチャネル活性化合物：アバメクチン(abamectin)、エマメクチン安息香酸塩(emamectin-benzoate)、レピメクチン(lepimectin)、ミルベメクチン(milbemectin)等。 Chloride ion channel active compounds: abamectin, emamectin benzoate, lepimectin, milbemectin and the like.
　幼若ホルモン類似化合物：キノプレン(kinoprene)、メトプレン(methoprene)、フェノキシカルブ(fenoxycarb)、ピリプロキシフェン(pyriproxyfen)等。 Juvenile hormone analogs: kinoprene, metoprene, phenoxycarb, pyriproxyfen, etc.
　非選択性阻害化合物：臭化メチル(methyl bromide)、クロルピクリン(chloropicrin)等。 Non-selective inhibitory compounds: methyl bromide, chloropicrin, etc.
　同翅目選択的摂食阻害化合物：ピメトロジン(pymetrozine)、フロニカミド(flonicamid)等。 Homogeneous selective feeding inhibitory compounds: pymetrozine, flonicamid, etc.
　ダニ類成長阻害化合物：クロフェンテジン(clofentezine)、ヘキシチアゾックス(hexythiazox)、エトキサゾール(etoxazole)等。 Tick growth inhibitory compounds: clofentezine, hexythiazox, etoxazole, etc.
　微生物由来昆虫中腸内膜破壊剤：バチルス　チューリンゲンシス(Bacillus thuringiensis)等。 Microorganism-derived insect midgut membrane destroyer: Bacillus thuringiensis, etc.
　ATP合成阻害化合物：ジアフェンチウロン(diafenthiuron)、アゾシクロチン(azocyclotin)、シヘキサチン(cyhexatin)、酸化フェンブタスズ(fenbutatin oxide)、プロパルギット(propargite)、テトラジホン(tetradifon)等。 ATP synthesis inhibiting compounds: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon, etc.
　酸化的リン酸化脱共役化合物：クロルフェナピル(chlorfenapyr)等。 Oxidative phosphorylation uncoupling compounds: chlorfenapyr and the like.
　ニコチン性アセチルコリン受容体チャネル阻害化合物：ベンスルタップ(bensultap)、カルタップ塩酸塩(cartap hydrochloride)、チオシクラム(thiocyclam)等。 Nicotinic acetylcholine receptor channel inhibitory compounds: bensultap, cartap hydrochloride, thiocyclam, etc.
　キチン生合成阻害化合物：クロルフルアズロン(chlorfluazuron)、ジフルベンズロン(diflubenzuron)、フルフェノクスロン(flufenoxuron)、ヘキサフルムロン(hexaflumuron)、ルフェヌロン(lufenuron)、ノバルロン(novaluron)、テフルベンズロン(teflubenzuron)、トリフルムロン(triflumuron)、ブプロフェジン(buprofezin)、ビストリフルロン(bistrifluron)、ノビフルムロン(noviflumuron)等。 Chitin biosynthesis inhibiting compounds: chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron triflumuron, buprofezin, bistrifluron, noviflumuron and the like.
　脱皮・変態阻害化合物：シロマジン(cyromazine)、クロマフェノジド(chromafenozide)、ハロフェノジド(halofenozide)、メトキシフェノジド(methoxyfenozide)、テブフェノジド(tebufenozide)等。 Molting / metamorphosis inhibiting compounds: cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide and the like.
　オクトパミン受容体作動化合物：アミトラズ(amitraz)等。 Octopamine receptor agonist compound: amitraz and the like.
　電子伝達系阻害化合物：ヒドラメチルノン(hydramethylnon)、アセキノシル(acequinocyl)、フルアクリピリム(fluacrypyrim)、フェナザキン(fenazaquin)、フェンピロキシメート(fenpyroximate)、ピリミジフェン(pyrimidifen)、ピリダベン(pyridaben)、テブフェンピラド(tebufenpyrad)、トルフェンピラド(tolfenpyrad)、ロテノン(rotenone)、リン酸化アルミニウム(aluminium phosphide)、シエノピラフェン(cyenopyrafen)、シフルメトフェン(cyflumetofen)等。 Electron transport inhibitor: hydramethylnon, acequinocyl, fluacrypyrim, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tebufenpyrad, tebufenpyrad tolfenpyrad), rotenone, aluminum phosphide, cyenopyrafen, cyflumetofen and the like.
　電位依存性ナトリウムチャンネル阻害化合物：インドキサカルブ(indoxacarb)、メタフルミゾン(metaflumizone)等。 Voltage-gated sodium channel inhibitor compounds: indoxacarb, metaflumizone, etc.
　脂質合成阻害化合物：スピロジクロフェン(spirodiclofen)、スピロメシフェン(spiromesifen)、スピロテトラマト(spirotetramat)等。 Lipid synthesis inhibiting compounds: spirodiclofen, spiromesifen, spirotetramat and the like.
　リアノジンレセプター阻害化合物：クロラントラニリプロール(chlorantraniliprole)、シアントラニルプロール(cyantraniliprol)、フルベンジアミド(flubendiamide)等。 Ryanodine receptor inhibitor compounds: chlorantraniliprole, cyantraniliprol, flubendiamide and the like.
　その他のあるいは未明な作用を有する化合物：アザジラクチン(azadirachtin)、ベンゾキシメート(benzoximate)、ビフェナゼート(bifenazate)、キノメチオネート(chinomethionat)、ジコホル(dicofol)、ピリダリル(pyridalyl)、ピリフルキナゾン(pyrifluquinazon)、フルエンスルホン(fluensulfone)等が挙げられる。 Other or unclear compounds: azadirachtin, benzoximate, bifenazate, chinomethionat, dicofol, pyridalyl, pyrifluquinazon, fluenesulfone fluensulfone) and the like.
　除草剤の例としては、下記の化合物を挙げることができる。 Examples of herbicides include the following compounds.
　脂質合成阻害剤：フルアジホップ・ブチル(fluazifop- butyl)、キザロホップ・エチル(quizalofop-ethyl)、シハロホップ・ブチル(cyhalofop-butyl)、ジクロホップ・メチル(diclofop-methyl)、フェノキサプロップ・P・エチル(fenoxaprop-P-ethyl)、アロキシジム(alloxydim)、セトキシジム(sethoxydim)、メタミホップ(metamifop)、エスプロカルブ(esprocarb)、プロスルホカルブ(prosulfocarb)、ピリブチカルブ(pyributicarb)、、ベンフレセート(benfuresate)、エトフメセート(ethofumesate)等。 Lipid synthesis inhibitors: fluazifop- butyl, quizalofop-ethyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl -P-ethyl, alloxydim, sethoxydim, metamifop, esprocarb, prosulfocarb, pyributicarb, benfuresate, etofumesate and the like.
　アセト乳酸合成酵素（ＡＬＳ）阻害剤：アミドスルフロン(amidosulfuron)、アジムスルフロン(azimsulfuron)、ベンスルフロン・メチル(bensulfuron-methyl)、クロリムロン・エチル(chlorimuron-ethyl)、シノスルフロン(cinosulfuron)、シクロスルファムロン(cyclosulfamuron)、エトキシスルフロン(ethoxysulfuron)、ピラゾスルフロン・エチル(pyrazosulfuron-ethyl)、ホラムスルフロン(foramsulfuron)、イマゾスルフロン(imazosulfuron)、ヨードスルフロン(iodosulfuron)、クロロスルフロン(chlorsulfuron)、チフェンスルフロン・メチル(thifensulfuron-methyl)、フラザスルフロン(flazaslfuron)、ピリミノバック・メチル(pyriminobac-methyl)、フロラスラム(florasulam)、イマザピル(imazapyr)、イマザモックス(imazamox)、イマザキン(imazaquin)、メソスルフロンメチル (mesosulfuron-methyl)、ジメフロン（dimefuron)、プロポキシカルバゾン(propoxycarbazone)、フルカルバゾン(flucarbazone)、メトスラム(metosulam)、ペノキススラム(penoxsulam)、フルセトスルフロン(flucetosulfuron)、ベンカルバゾン(bencarbazone)、ピリミスルファン(pyrimisulfan)、ピロクススラム(pyroxsulam)、チエンカルバゾン(thiencarbazone)、オルトスルファムロン(orthosulfamuron）、プロピリスルフロン(propyrisulfuron)、メタゾスルフロン(metazosulfuron)等。 Acetolactate synthase (ALS) inhibitors: amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, cinosulfuron, cyclosulfam Cyclosulfamuron, ethoxysulfuron, pyrazosulfuron-ethyl, foramsulfuron, imazosulfuron, iodosulfuron, chlorosulfuron, thiosulfuron Methyl (thifensulfuron-methyl), flazaslfuron (flazaslfuron), pyriminobac-methyl, florasulam, imazapyr, imazamox, imazaquin, imazoquin, mesosulfuron methyl methyl), dimefuron, propoxy Rubazone (propoxycarbazone), full carbazone (flucarbazone), metosulam, penoxsulam, flucetosulfuron, bencarbazone, pyrimisulfan, pyroxsulamth, carbazone Sulfamuron (orthosulfamuron), propyrisulfuron (metapysulfuron), metazosulfuron, etc.
　光合成電子伝達系阻害剤：シマジン(simazine)、メトリブジン(metribuzin)、アミカルバゾン(amicarbazone)、ジウロン(diuron)、リニュロン(linuron)、アイオキシニル(ioxynil)、ジメタメトリン(dimethametryn)、フェンメディファム(phenmedipham)、オキサジアルギル(oxadiargyl)、デスメディファム(desmedipham)、イソプロツロン(isoproturon)、ネブロン(neburon)、ブロモキシニル(bromoxynil)、メタベンズチアズロン(methabenzthiazuron)、メタミトロン(metamitron)、パラコート(paraquat)、ジクワット(diquat)、アトラジン(atrazine)、フルフェンピル・エチル(flufenpyr-ethyl)、ベンタゾン(bentazone)等。 Photosynthesis electron transport system inhibitors: Simazine, metribuzin, amicarbazone, diuron, linuron, ioxynil, dimethametryn, phenmedipham, oxadiargyl (oxadiargyl), desmedipham, isoproturon, neburon, bromoxynil, methabenzthiazuron, metamitron, paraquat, diquat, Atrazine, flufenpyr-ethyl, bentazone, etc.
　プロトックス阻害剤：ビフェノックス(bifenox)、ラクトフェン(lactofen)、フルミオキサジン(flumioxazin)、カルフェントラゾン・エチル(carfentrazone-ethyl)、ぺントキサゾン(pentoxazone)、ピラクロニル(pyraclonil)、ピラフルフェン・エチル(pyraflufen-ethyl)、オキサジアゾン(oxadiazon)、スルフェントラゾン(sulfentrazone)、アシフルオルフェン(acifluorfen-sodium)、フルチアセット・メチル(fluthiacet-methyl)等。 Protox inhibitors: bifenox, lactofen, flumioxazin, carfentrazone-ethyl, pentoxazone, pyraclonil, pyraflufen- ethyl), oxadiazon, sulfentrazone, acifluorfen-sodium, fluthiacet-methyl and the like.
　４－ＨＰＰＤ阻害剤：メソトリオン(mesotrione)、イソキサフルトール(isoxaflutole)、ベンゾフェナップ(benzofenap)、ベンゾビシクロン(benzobicyclon）、トプラメゾン(topramezone)、、スルコトリオン(sulcotrione)、テフリルトリオン(tefuryltrione)、ピラスルホトール(pyrasulfotole)、ピラゾキシフェン(pyrazoxyfen)、ピラゾレート(pyrazolate)等。 4-HPPD inhibitors: mesotrione, isoxaflutole, benzofenap, benzobicyclon, topramezone, sulcotrione, tefyltrione ), Pyrasulfotole, pyrazoxifene, pyrazolate, and the like.
　カロテノイド生合成阻害剤：アクロニフェン(aclonifen)、フルルタモン(flurtamone)、ジフルフェニカン(diflufenican)、フルリドン(fluridone)等。 Carotenoid biosynthesis inhibitors: aclonifen, flurtamone, diflufenican, fluridone, etc.
　ＥＰＳＰ合成酵素阻害剤：グリホサート(glyphosate)等。 EPSP synthase inhibitor: glyphosate and the like.
　グルタミン酸合成酵素阻害剤：グルホシネートアンモニウム塩(glufosinate-ammonium)、ビアラホス(bialaphos)等。 Glutamate synthase inhibitors: glufosinate-ammonium, bialaphos, etc.
　細胞分裂阻害剤：オリザリン(oryzalin)、ペンディメタリン(pendimethalin)、ブタミホス(butamifos)、カルベタミド(carbetamide)、トリアジフラム(triaziflam)、フルポキサム(flupoxam)、ジクロベニル(dichlobenil)、ＩＰＣ(propham)、トリフルラリン(trifluralin)、クミルロン(cumyluron)、インダジフラム(indaziflam)等。 Cell division inhibitor: oryzalin, pendimethalin, butamifos, carbetamide, triaziflam, flupoxam, dichlobenil, IPC (propham), trifluralin ), Cumyluron, indaziflam and the like.
　ＶＬＣＦＡｓ阻害剤：アラクロール(alachlor)、メトラクロール(metolachlor）、テニルクーロル(thenylchlor)、メフェナセット(mefenacet)、フェントラザミド(fentrazamide)、カフェンストロール(cafenstrole)、プレチラクロール(pretilachlor)、インダノファン(indanofan)、アニロホス(anilofos)、フルフェナセット(flufenacet)、ナプロパミド(napropamide)、ジメテナミド(dimethenamid)、プロピソクロール(propisochlor)、フェノキサスルホン(fenoxasulfone)、イプフェンカルバゾン(Ipfencarbazone)等。 VLCFAs inhibitors: alachlor, metolachlor, tenenylchlor, mefenacet, fentrazamide, cafenstrole, pretilachlor, indanofan, anilofos Flufenacet, napropamide, dimethenamid, propisochlor, fenoxasulfone, ipfencarbazone and the like.
　オーキシン活性型除草剤：クロメプロップ(clomeprop)、２，４－Ｄ、ＭＣＰＡ、ＭＣＰＢ、ＭＣＰＰ、トリクロピル(triclopyr)等。 Auxin-active herbicides: Chromeprop, 2,4-D, MCPA, MCPB, MCPP, triclopyr, etc.
　作用性未知化合物：シンメチリン(cinmethylin)、ブロモブチド(bromobutide)、ダイムロン(daimuron)、オキサジクロメホン(oxaziclomefone)、エトベンザニド(etobenzanid)、ベンチオカーブ(benthiocarb)、ピロキサスルホン(pyroxasulfone)等。 Compounds with unknown activity: cinmethylin, bromobutide, daimuron, oxaziclomefone, etobenzanid, benthiocarb, pyroxasulfone, etc.
　酸化的リン酸化脱共役剤：ジノテルブ(dinoterb)、トリブホス(tribufos)、エテホン(ethephon)、チジアズロン(thidiazuron)、シクラニリド(cyclanilide)、サフルフェナシル(saflufenacil)、イソキサジフェン(isoxadifen)、エチオジン(ethiozin)等。 Oxidative phosphorylation uncouplers: dinoterb, tribufos, ethephon, thidiazuron, cyclanilide, saflufenacil, isoxadifen, ethiozin, etc.
　生物農薬の例としては、
　（１）核多角体ウイルス(Nuclear polyhedrosis virus、NPV)、顆粒病ウイルス(Granulosis virus、GV)、細胞質多角体病ウイルス(Cytoplasmic polyhedrosis virus、CPV)等。
　（２）スタイナ－ネマ・カーポカプサエ(Steinernema carpocapsae)、スタイナ－ネマ・グラセライ(Steinernema glaseri)、モノクロスポリウム・フィマトパガム(Monacrosporium phymatophagum)、スタイナ－ネマ・クシダエ(Steinernema kushidai)、パスツーリア・ペネトランス(Pasteuria penetrans)等。
　（３）アグロバクテリウム・ラジオバクター(Agrobacterium radiobacter)、バチルス・ズブチリス(Bacillus subtilis)、エルビニア・カロトボーラ(Erwinia carotovora)、シュードモナス・フルオレッセンス(Pseudomonas fluorescens)、タラロマイセス・フラバス(Talaromyces flavus)、トリコデルマ・アトリロビリデ(Trichoderma atroviride)等。
　（４）バチルス・チューリンゲンシス(Bacillus thuringiensis)、ボーベリア・ブロンニアティ(Beauveria brongniartii)、ボーベリア・バシアーナ(Beauveria bassiana)、ペキロマイセス(Paecilomyces fumosoroseus)、バーティシリ・レカニ(Verticillium lecanii)、ザントモナス・キャンペリトリス(Xanthomonas campestris)等。
　（５）オンシツツヤコバチ(Encarsia formosa)、サバクツヤコバチ（Eretmocerus eremicus)、チチュウカイツヤコバチ（Eretmocerus mundus)、コレマンアブラバチ(Aphidius colemani)、ショクガタマバエ(Aphidoletes aphidimyza)、イサエアヒメコバチ(Diglyphus isaea)、ハモグリコマユバチ(Dacnusa sibirica)、チリカブリダニ(Phytoseiulus persimilis)、ククメリスカブリダニ(Amblyseius cucumeris)、ミヤコカブリダニ（Amblyseius californicus)、タイリクヒメハナカメムシ(Orius strigicollis)等。 Examples of biological pesticides include
(1) Nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), etc.
(2) Steinernema carpocapsae, Steinernema glaseri, Monocrosporium phymatophagum, Steinernema kushidai, Steinernema kushidai etc.
(3) Agrobacterium radiobacter, Bacillus subtilis, Erwinia carotovora, Pseudomonas fluorescens, Talaromyces flavus, Talaromyces flavus, (Trichoderma atroviride) etc.
(4) Bacillus thuringiensis, Beauveria brongniartii, Beauveria bassiana, Paecilomyces fumosoroseus, Verticillium lecanii, nas Xest etc.
(5) Onsatsume wasp (Encarsia formosa), Sakutaku bee (Eretmocerus eremicus), Scarlet wasp (Eretmocerus mundus), Colleman's wasp (Aphidius colemani), Aphidoletes aphidimyzaly ), Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumeris, Amblyseius californicus, Orius strigicollis, etc.
　フェロモン剤の例としては、コドレルア((E,E)-8,10-Dodecadien-1-ol)、ビートアーミールア・Ｂ((Z)-9-Tetradecen-1-ol)、テトラドデセニルアセテート((Z)-11-Tetradecenyl acetate)、ピリマルア(14-Methyl-1-octadecene)、ピーチフルア((Z)-13-Eicosen-10-one)等が挙げられる。 Examples of pheromone agents include: chodrelua ((E, E) -8,10-Dodecadien-1-ol), beet armorua B ((Z) -9-Tetradecen-1-ol), tetradodecenyl Examples thereof include acetate ((Z) -11-Tetradecenyl acetate), pyrimalua (14-Methyl-1-octadecene), peach flua ((Z) -13-Eicosen-10-one), and the like.
　天然殺菌剤・天然殺虫剤の例としては、マシン油(Machine oils)、メチルフェニルアセテート(Methylphenyl acetate）、α-ピネン(α-Pinene)、蛋白加水分解物(Protein hydrolysate)、(Z)-1-Tetradecen-1-ol、テレピン油(Turpentine)等が挙げられる。 Examples of natural fungicides and insecticides include machine oils (Machine oils), methylphenylacetate (α), pinned (α-Pinene), protein hydrolysates (Protein hydrolysate), (Z) -1 -Tetradecen-1-ol, turpentine and the like.
　実施例１
（１）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝Ｈ、Ｒ１，Ｒ２＝－ＣＨ＝ＣＨ－ＣＨ＝ＣＨ－、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．１の合成）
段階Ａ：４－キノリンカルボキシアルデヒド　オキシム Example 1
(1) In the general formula (I), A = 1,4-C 6 H 4 , B = H, R 1 , R 2 = —CH═CH—CH═CH—, R 3 = H, R 4 = H ( Table 1, Synthesis of Compound No. 1)
Stage A: 4-quinolinecarboxaldehyde oxime
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000009
　エタノール６００ｍＬと水３００ｍＬに４－キノリンカルボキシアルデヒド４０．５０ｇ、ヒドロキシルアミン塩酸塩２３．００ｇ、酢酸ナトリウム３１．４０ｇを加え、室温で３時間撹拌した。反応液を濃縮し、残渣を水に懸濁し、白色固体をろ過した。固体を水で洗浄し、減圧下乾燥してオキシム化合物４２．５７ｇを得た。
段階Ｂ：４－（アミノメチル）キノリン To 600 mL of ethanol and 300 mL of water were added 40.50 g of 4-quinolinecarboxaldehyde, 23.00 g of hydroxylamine hydrochloride and 31.40 g of sodium acetate, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated, the residue was suspended in water, and the white solid was filtered. The solid was washed with water and dried under reduced pressure to obtain 42.57 g of an oxime compound.
Step B: 4- (Aminomethyl) quinoline
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000010
　メタノール１．００Ｌに上記段階で得られたオキシム化合物５０．００ｇ、パラジウム炭素（パラジウム１０％、約５５％水湿潤品）１３．６０ｇを加え、１気圧の水素圧下室温で１時間撹拌した。反応液をセライトろ過し、有機層を濃縮し、残渣を減圧下乾燥してキノリン化合物４６．０４ｇを得た。
段階Ｃ：４－ヨード－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミド To 1.00 L of methanol were added 50.00 g of the oxime compound obtained in the above step and 13.60 g of palladium carbon (palladium 10%, approximately 55% water-wet product), and the mixture was stirred at room temperature for 1 hour under a hydrogen pressure of 1 atm. The reaction solution was filtered through Celite, the organic layer was concentrated, and the residue was dried under reduced pressure to obtain 46.04 g of a quinoline compound.
Step C: 4-Iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000011
　ジクロロメタン５３０ｍＬに上記段階で得られたキノリン化合物４６．０４ｇ、トリエチルアミン４０．３０ｍＬを加え、溶液を０℃に冷却した。冷却後この溶液に４－ヨードベンゼンスルホニルクロリド８３．８０ｇを数回に分けて加え、室温で２．５時間攪拌した。反応液に水を加え、白色固体をろ過した。固体を水で２回、ジクロロメタンで１回洗浄し、減圧下乾燥してスルホンアミド化合物９９．７２ｇを得た。
段階Ｄ：Ｎ－（キノリン－４－イルメチル）－４－（（トリメチルシリル）エチニル）ベンゼンスルホンアミド 46.04 g of the quinoline compound obtained in the above step and 40.30 mL of triethylamine were added to 530 mL of dichloromethane, and the solution was cooled to 0 ° C. After cooling, 83.80 g of 4-iodobenzenesulfonyl chloride was added in several portions to this solution and stirred at room temperature for 2.5 hours. Water was added to the reaction solution, and the white solid was filtered. The solid was washed twice with water and once with dichloromethane and dried under reduced pressure to obtain 99.72 g of a sulfonamide compound.
Step D: N- (Quinolin-4-ylmethyl) -4-((trimethylsilyl) ethynyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000012
　テトラヒドロフラン１．５０Ｌに上記段階で得られたスルホンアミド化合物６３．６０ｇ、トリメチルシリルアセチレン３１．１０ｍＬ、ジクロロビス（トリフェニルホスフィン）パラジウム５．２６ｇ、ヨウ化銅１．４３ｇ、トリエチルアミン８３．４０ｍＬを加え、７０℃で４時間撹拌した。反応液を室温まで冷却し、セライトろ過した。ろ液を濃縮後、残渣に水を加え、クロロホルムで抽出した。有機層を飽和炭酸水素ナトリウム水溶液及び飽和食塩水で洗浄後、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、残渣をジエチルエーテルに懸濁し、黄色固体をろ過した。固体をジエチルエーテルで洗浄し、減圧下乾燥してトリメチルシリル化合物５８．４０ｇを得た。
段階Ｅ：４－エチニル－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミド To 1.50 L of tetrahydrofuran was added 63.60 g of the sulfonamide compound obtained in the above step, 31.10 mL of trimethylsilylacetylene, 5.26 g of dichlorobis (triphenylphosphine) palladium, 1.43 g of copper iodide, 83.40 mL of triethylamine, and 70 Stir for 4 hours at ° C. The reaction was cooled to room temperature and filtered through celite. The filtrate was concentrated, water was added to the residue, and the mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, the residue was suspended in diethyl ether, and the yellow solid was filtered. The solid was washed with diethyl ether and dried under reduced pressure to obtain 58.40 g of a trimethylsilyl compound.
Step E: 4-Ethynyl-N- (quinolin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000013
　メタノール２５０ｍＬに上記段階で得られたトリメチルシリル化合物５．００ｇ、炭酸カリウム３．５０ｇを加え、室温で３０分間攪拌した。反応液を濃縮し、残渣に水及び６規定塩酸を加え、クロロホルムで抽出した。有機層を飽和食塩水で洗浄後、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、残渣を減圧下乾燥してエチニル化合物３．１７ｇを得た。 5.00 g of the trimethylsilyl compound obtained in the above step and 3.50 g of potassium carbonate were added to 250 mL of methanol, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated, water and 6N hydrochloric acid were added to the residue, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine and dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was dried under reduced pressure to obtain 3.17 g of an ethynyl compound.
　同様の製造法により、表１、化合物Ｎｏ．２～４，６～８，１１～１６，１８～２１，２３～２８，３０～３９，４１～４５，４７～５０，５２～５５，５７～６９，７１，８７，９７，１０９～１３３，１３５～１４０，１４２～１５６，１５８，１６０～１６４，１７０～１７７を合成した。 According to the same production method, Table 1, Compound No. 2 to 4, 6 to 8, 11 to 16, 18 to 21, 23 to 28, 30 to 39, 41 to 45, 47 to 50, 52 to 55, 57 to 69, 71, 87, 97, 109 to 133, 135-140, 142-156, 158, 160-164, 170-177 were synthesized.
　なお、Ｎ－（２－エチニルフェニル）アセトアミド、Ｎ－（３－エチニルフェニル）アセトアミド、Ｎ－（４－エチニルフェニル）アセトアミドは特許文献１６（ＵＳ２００４／８７７８９）に記載の方法に準じて対応するアニリンより製造した。４－エチニルベンゾニトリル、１－（ジフルオロメトキシ）－４－エチニルベンゼン、（４－エチニルフェニル）（メチル）スルファン、（４－エチニルフェニル）（トリフルオロメチル）スルファン、５－エチニル－２，３－ジヒドロベンゾフラン、１，４－ジクロロ－２－エチニルベンゼン、１，３－ジクロロ－２－エチニルベンゼン、２－クロロ－１－エチニル－４－フルオロベンゼン、４－エチニルキノリン、２－エチニルチアゾール、４－エチニルチアゾール、５－エチニルチアゾール、４－エチニル－１－メチル－１Ｈ－ピラゾール、５－エチニル－１－メチル－１Ｈ－ピラゾールは非特許文献１（Ｓｙｎｌｅｔｔ，１９９６，５２１．）に記載の方法に準じて対応するアルデヒドより製造した。１－（２－エチニルフェニル）エタノン、２，４－ジクロロ－１－エチニルベンゼン、１，３－ジクロロ－５－エチニルベンゼン、３－エチニルフラン、２－エチニルチオフェンは非特許文献２（Ｊｏｕｒｎａｌ　ｏｆ　Ｏｒｇａｎｉｃ　Ｃｈｅｍｉｓｔｒｙ，１９９６，６１，６９０６．）に記載の方法に準じて対応するトリメチルシリルアセチレンより製造した。２－エチニルフランは特許文献１７（ＷＯ２００９／１１１８３０）に記載の方法に準じて対応するジブロモオレフィンより製造した。２－エチニル－２－メチル－１，３－ジオキソラン、２－エチニル－２－メチル－１，３－ジオキサンは非特許文献３（Ｊｏｕｒｎａｌ　ｏｆ　Ｏｒｇａｎｉｃ　Ｃｈｅｍｉｓｔｒｙ，１９９８，６３，１７６１．）に記載の方法に準じて３－ブチン－２－オンより製造した。１，１－ジクロロ－２－エチニルシクロプロパンは非特許文献４（Ｚｈｕｒｎａｌ　Ｏｒｇａｎｉｃｈｅｓｋｏｉ　Ｋｈｉｍｉｉ，１９８６，２２，１１９５．）に記載の方法に準じて対応するアルデヒドを製造した後、非特許文献５（Ｓｙｎｌｅｔｔ，１９９６，５２１．）に記載の方法に準じて製造した。１，１－ジクロロ－２－メチル－２－エチニルシクロプロパンは非特許文献６（Ｚｈｕｒｎａｌ　Ｏｒｇａｎｉｃｈｅｓｋｏｉ　Ｋｈｉｍｉｉ，１９８２，１８，２２９５．）に記載の方法に準じて対応するエンインより製造した。その他のアセチレンは市販品を用いた。 N- (2-ethynylphenyl) acetamide, N- (3-ethynylphenyl) acetamide, and N- (4-ethynylphenyl) acetamide are the corresponding anilines according to the method described in Patent Document 16 (US2004 / 87789). More manufactured. 4-ethynylbenzonitrile, 1- (difluoromethoxy) -4-ethynylbenzene, (4-ethynylphenyl) (methyl) sulfane, (4-ethynylphenyl) (trifluoromethyl) sulfane, 5-ethynyl-2,3- Dihydrobenzofuran, 1,4-dichloro-2-ethynylbenzene, 1,3-dichloro-2-ethynylbenzene, 2-chloro-1-ethynyl-4-fluorobenzene, 4-ethynylquinoline, 2-ethynylthiazole, 4- Ethinylthiazole, 5-ethynylthiazole, 4-ethynyl-1-methyl-1H-pyrazole, and 5-ethynyl-1-methyl-1H-pyrazole are in accordance with the method described in Non-Patent Document 1 (Synlett, 1996, 521.). From the corresponding aldehyde. 1- (2-ethynylphenyl) ethanone, 2,4-dichloro-1-ethynylbenzene, 1,3-dichloro-5-ethynylbenzene, 3-ethynylfuran and 2-ethynylthiophene are not described in Non-Patent Document 2 (Journal of Organic). Chemistry, 1996, 61, 6906.) was prepared from the corresponding trimethylsilylacetylene. 2-Ethynylfuran was produced from the corresponding dibromoolefin according to the method described in Patent Document 17 (WO2009 / 111830). 2-Ethynyl-2-methyl-1,3-dioxolane and 2-ethynyl-2-methyl-1,3-dioxane are the same as those described in Non-Patent Document 3 (Journal of Organic Chemistry, 1998, 63, 1761.). Similarly, it was produced from 3-butyn-2-one. 1,1-dichloro-2-ethynylcyclopropane was prepared according to the method described in Non-Patent Document 4 (Zhurnal Organicheskoi Kimii, 1986, 22, 1195.), and then produced Non-Patent Document 5 (Synlett, 1996, 521.). 1,1-dichloro-2-methyl-2-ethynylcyclopropane was produced from the corresponding enyne according to the method described in Non-Patent Document 6 (Zhurnal Organicheskoi Kimii, 1982, 18, 2295.). As other acetylenes, commercially available products were used.
（２）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝２－ＣＨ２Ｆ－Ｃ６Ｈ４、Ｒ１，Ｒ２＝－ＣＨ＝ＣＨ－ＣＨ＝ＣＨ－、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．５の合成）
段階Ａ：４－（（２－（フルオロメチル）フェニル）エチニル）－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミド (2) In the general formula (I), A = 1,4-C 6 H 4 , B = 2-CH 2 F—C 6 H 4 , R 1 , R 2 = —CH═CH—CH═CH—, R 3 = H, R 4 = H (Table 1, Synthesis of Compound No. 5)
Step A: 4-((2- (Fluoromethyl) phenyl) ethynyl) -N- (quinolin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000014
　ジクロロメタン３０．００ｍＬに表１、化合物Ｎｏ．４のアルコール化合物４００ｍｇ、三フッ化Ｎ，Ｎ－ジエチルアミノ硫黄２００μＬを加え、室温で１時間攪拌した。反応液に飽和炭酸水素ナトリウム水溶液を加えて分液し、ジクロロメタンで２回抽出した後、有機層を硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、残渣をフラッシュ自動精製装置（ｂｉｏｔａｇｅ　ＡＢ社製／ＩｓｏｌｅｒａＴＭ）によるシリカゲルフラッシュクロマトグラフィー（酢酸エチル－ヘキサン：２０％－８０％で溶出）で精製することによって、フルオロ化合物２５０ｍｇを得た。 In 30.00 mL of dichloromethane, Table 1, Compound No. 4 mg of the alcohol compound 4 and 200 μL of N, N-diethylaminosulfur trifluoride were added and stirred at room temperature for 1 hour. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, and the mixture was separated, extracted twice with dichloromethane, and then the organic layer was dried over sodium sulfate. After filtering the sodium sulfate, the organic layer is concentrated, and the residue is purified by silica gel flash chromatography (eluted with ethyl acetate-hexane: 20% -80%) with a flash automatic purifier (Biotage AB / Isolera ™ ). Gave 250 mg of fluoro compound.
　同様の製造法により、表１、化合物Ｎｏ．１６５，１６７，１６８を合成した。 According to the same production method, Table 1, Compound No. 165, 167, and 168 were synthesized.
（３）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝２－ＣＯ２ＣＨ３－Ｃ６Ｈ４、Ｒ１，Ｒ２＝－ＣＨ＝ＣＨ－ＣＨ＝ＣＨ－、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．９の合成）
段階Ａ：２－（（４－（Ｎ－（キノリン－４－イルメチル）スルファモイル）フェニル）エチニル）安息香酸メチル (3) In the general formula (I), A = 1,4-C 6 H 4 , B = 2-CO 2 CH 3 —C 6 H 4 , R 1 , R 2 = —CH═CH—CH═CH—, R 3 = H, R 4 = H (Table 1, Synthesis of Compound No. 9)
Step A: methyl 2-((4- (N- (quinolin-4-ylmethyl) sulfamoyl) phenyl) ethynyl) benzoate
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000015
　テトラヒドロフラン６．００ｍＬに表１、化合物Ｎｏ．１のエチニル化合物３８０ｍｇ、２－ヨード安息香酸メチル４６４ｍｇ、ジクロロビス（トリフェニルホスフィン）パラジウム４１ｍｇ、ヨウ化銅１１ｍｇ、トリエチルアミン６６０μＬを加え、７０℃で８時間撹拌した。反応液を室温まで冷却し、セライトろ過した後に濃縮した。残渣に水を加え、クロロホルムで抽出した。有機層を飽和食塩水で洗浄後、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、残渣をジエチルエーテルに懸濁し、固体をろ過した。固体をジエチルエーテルで洗浄し、減圧下乾燥して安息香酸メチル化合物３０２ｍｇを得た。 In Table 1, compound no. 380 mg of 1 ethynyl compound, 464 mg of methyl 2-iodobenzoate, 41 mg of dichlorobis (triphenylphosphine) palladium, 11 mg of copper iodide and 660 μL of triethylamine were added and stirred at 70 ° C. for 8 hours. The reaction mixture was cooled to room temperature, filtered through celite, and concentrated. Water was added to the residue and extracted with chloroform. The organic layer was washed with saturated brine and dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, the residue was suspended in diethyl ether, and the solid was filtered. The solid was washed with diethyl ether and dried under reduced pressure to obtain 302 mg of methyl benzoate compound.
　同様の製造法により、表１、化合物Ｎｏ．１０，１７，２２，２９，４０，４６，５１，５６，７０，７２～８６，８８～９６，９８～１０８，１６９を合成した。 According to the same production method, Table 1, Compound No. 10, 17, 22, 29, 40, 46, 51, 56, 70, 72 to 86, 88 to 96, 98 to 108, and 169 were synthesized.
　なお、２－フルオロ－３－ヨードピリジンは非特許文献７（Ｔｅｔｒａｈｅｄｒｏｎ，１９９３，４９，４９．）に記載の方法に準じて２－フルオロピリジンより製造した。２－フルオロ－４－ヨードピリジンは非特許文献８（Ｊｏｕｒｎａｌ　ｏｆ　Ｏｒｇａｎｉｃ　Ｃｈｅｍｉｓｔｒｙ，１９９３，５８，７８３２．）に記載の方法に準じて２－フルオロ－３－ヨードピリジンより製造した。３－ヨード－２－メトキシピリジン、４－ヨード－２－メトキシピリジンは特許文献１８（ＷＯ２００８／２５５０９）に記載の方法に準じて対応するフルオロピリジンより製造した。その他のアリールハライドは市販品を用いた。 2-Fluoro-3-iodopyridine was produced from 2-fluoropyridine according to the method described in Non-Patent Document 7 (Tetrahedron, 1993, 49, 49.). 2-Fluoro-4-iodopyridine was produced from 2-fluoro-3-iodopyridine according to the method described in Non-Patent Document 8 (Journal of Organic Chemistry, 1993, 58, 7832.). 3-Iodo-2-methoxypyridine and 4-iodo-2-methoxypyridine were prepared from the corresponding fluoropyridines according to the method described in Patent Document 18 (WO2008 / 25509). As other aryl halides, commercially available products were used.
（４）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝ＣＨＯ、Ｒ１，Ｒ２＝－ＣＨ＝ＣＨ－ＣＨ＝ＣＨ－、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．１３４の合成）
段階Ａ：４－（３－オキソ－１－プロピニル）－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミド (4) In the general formula (I), A = 1,4-C 6 H 4 , B = CHO, R 1 , R 2 = —CH═CH—CH═CH—, R 3 = H, R 4 = H ( Table 1, Synthesis of Compound No. 134)
Step A: 4- (3-Oxo-1-propynyl) -N- (quinolin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000016
　水３４．００ｍＬに表１、化合物Ｎｏ．１５３のアセタール化合物２．８７ｇ、トリフルオロ酢酸６７．００ｍＬを加え、室温で１時間撹拌した。反応液を濃縮し、残渣に飽和炭酸水素ナトリウム水溶液を加え、１０％メタノール－クロロホルムで抽出した。有機層を硫酸ナトリウムで乾燥し、硫酸ナトリウムをろ過した。有機層を濃縮し、残渣をジエチルエーテルに懸濁し、茶色固体をろ過した。固体をジエチルエーテルで洗浄し、減圧下乾燥してアルデヒド化合物２．０８ｇを得た。 In Table 34, compound no. 2.87 g of 153 acetal compound and 67.00 mL of trifluoroacetic acid were added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with 10% methanol-chloroform. The organic layer was dried over sodium sulfate and the sodium sulfate was filtered. The organic layer was concentrated, the residue was suspended in diethyl ether, and the brown solid was filtered. The solid was washed with diethyl ether and dried under reduced pressure to obtain 2.08 g of an aldehyde compound.
　同様の製造法により、表１、化合物Ｎｏ．１４１を合成した。 According to the same production method, Table 1, Compound No. 141 was synthesized.
（５）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝ＣＯＮＨＣＨ３、Ｒ１，Ｒ２＝－ＣＨ＝ＣＨ－ＣＨ＝ＣＨ－、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．１５７の合成）
段階Ａ：Ｎ－メチル－３－（４－（Ｎ－（キノリン－４－イルメチル）スルファモイル）フェニル）プロピオルアミド (5) In the general formula (I), A = 1,4-C 6 H 4 , B = CONHCH 3 , R 1 , R 2 = —CH═CH—CH═CH—, R 3 = H, R 4 = H (Table 1, Synthesis of Compound No. 157)
Step A: N-methyl-3- (4- (N- (quinolin-4-ylmethyl) sulfamoyl) phenyl) propiolamido
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000017
　テトラヒドロフラン１５．００ｍＬに表１、Ｎｏ．１５６のエステル化合物４００ｍｇ、４０％メチルアミン－メタノール溶液２．００ｍＬを加え、室温で２時間攪拌した。反応液を濃縮し、残渣をフラッシュ自動精製装置（ｂｉｏｔａｇｅ　ＡＢ社製／ＩｓｏｌｅｒａＴＭ）によるシリカゲルフラッシュクロマトグラフィー（酢酸エチル－ヘキサン：３０％－１００％の後メタノール－クロロホルム：１５％で溶出）で精製することによって、アミド化合物７５ｍｇを得た。 Add 15.00 mL of tetrahydrofuran to Table 1. 400 mg of 156 ester compound and 2.00 mL of 40% methylamine-methanol solution were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, and the residue was purified by silica gel flash chromatography (ethyl acetate-hexane: 30% -100% followed by methanol-chloroform: 15%) using a flash automatic purifier (Biotage AB / Isolera ™ ). As a result, 75 mg of an amide compound was obtained.
（６）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝Ｃ（＝ＮＯＣＨ３）ＣＨ３、Ｒ１，Ｒ２＝－ＣＨ＝ＣＨ－ＣＨ＝ＣＨ－、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．１５９の合成）
段階Ａ：４－（３－（メトキシイミノ）－１－ブチニル）－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミド (6) In general formula (I), A = 1,4-C 6 H 4 , B = C (= NOCH 3 ) CH 3 , R 1 , R 2 = —CH═CH—CH═CH—, R 3 = H, R 4 = H (Table 1, Synthesis of Compound No. 159)
Step A: 4- (3- (methoxyimino) -1-butynyl) -N- (quinolin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000018
　メタノール１０．００ｍＬに表１、Ｎｏ．１４１のケトン化合物５００ｍｇ、Ｏ－メチルヒドロキシルアミン塩酸塩２３０ｍｇ、硫酸ナトリウム３９０ｍｇ、ピリジン１．６０ｍＬを加え、室温で３０分間攪拌した。反応液に水を加え、酢酸エチルで２回抽出した。有機層を水で２回、飽和食塩水で１回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をシリカゲルフラッシュクロマトグラフィー（酢酸エチル－トルエン：５０％で溶出）で精製することによって、オキシム化合物４１０ｍｇをｃｉｓ：ｔｒａｎｓ＝４：６の異性体混合物として得た。 In Table 1, No. 1 in 10.00 mL of methanol. 141 ketone compound (500 mg), O-methylhydroxylamine hydrochloride (230 mg), sodium sulfate (390 mg) and pyridine (1.60 mL) were added, and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layer was washed twice with water and once with saturated brine, and then dried over magnesium sulfate. After filtering magnesium sulfate, the organic layer is concentrated, and the residue is purified by silica gel flash chromatography (eluted with ethyl acetate-toluene: 50%) to obtain 410 mg of oxime compound as an isomer mixture of cis: trans = 4: 6. Got as.
（７）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝ＣＨＦ２、Ｒ１，Ｒ２＝－ＣＨ＝ＣＨ－ＣＨ＝ＣＨ－、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．１６６の合成）
段階Ａ：４－（３，３－ジフルオロ－１－プロピニル）－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミド (7) In the general formula (I), A = 1,4-C 6 H 4 , B═CHF 2 , R 1 , R 2 = —CH═CH—CH═CH—, R 3 = H, R 4 = H (Table 1, Synthesis of Compound No. 166)
Step A: 4- (3,3-Difluoro-1-propynyl) -N- (quinolin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000019
　ジクロロメタン１０．００ｍＬに表１、Ｎｏ．１３４のアルデヒド化合物３５０ｍｇ、三フッ化Ｎ，Ｎ－ジエチルアミノ硫黄１９８μＬを加え、室温で４時間攪拌した。反応液に飽和炭酸水素ナトリウム水溶液、水、メタノールを加えて分液し、有機層を硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、残渣をフラッシュ自動精製装置（ｂｉｏｔａｇｅ　ＡＢ社製／ＩｓｏｌｅｒａＴＭ）によるシリカゲルフラッシュクロマトグラフィー（酢酸エチル－ヘキサン：５０％－１００％で溶出）で精製することによって、ジフルオロ化合物３５ｍｇを得た。 In Table 1, No. 1 in 10.00 mL of dichloromethane. 134 mg of aldehyde compound 134 and 198 μL of N, N-diethylaminosulfur trifluoride were added, and the mixture was stirred at room temperature for 4 hours. A saturated aqueous sodium hydrogen carbonate solution, water and methanol were added to the reaction solution, and the mixture was separated, and the organic layer was dried over sodium sulfate. After filtering sodium sulfate, the organic layer is concentrated, and the residue is purified by silica gel flash chromatography (elution with ethyl acetate-hexane: 50% -100%) using a flash automatic purifier (Biotage AB / Isolera ™ ). Gave 35 mg of difluoro compound.
（８）一般式（Ｉ）においてＡ＝２－ＣＨ３－１，４－Ｃ６Ｈ４、Ｂ＝Ｃ６Ｈ５、Ｒ１，Ｒ２＝－ＣＨ＝ＣＨ－ＣＨ＝ＣＨ－、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．１７８の合成）
段階Ａ：４－ブロモ－２－メチル－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミド (8) In the general formula (I), A = 2-CH 3 -1,4-C 6 H 4 , B = C 6 H 5 , R 1 , R 2 = —CH═CH—CH═CH—, R 3 = H, R 4 = H (Table 1, Synthesis of Compound No. 178)
Step A: 4-Bromo-2-methyl-N- (quinolin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000020
Figure JPOXMLDOC01-appb-C000020
　表１、化合物Ｎｏ．１の合成の段階Ｃにおいて、４－ヨードベンゼンスルホニルクロリドの代わりに４－ブロモ－２－メチルベンゼンスルホニルクロリドを用いることで、スルホンアミド化合物を得た。
段階Ｂ：２－メチル－４－（フェニルエチニル）－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミド Table 1, Compound No. In Step C of Synthesis 1, the sulfonamide compound was obtained by using 4-bromo-2-methylbenzenesulfonyl chloride instead of 4-iodobenzenesulfonyl chloride.
Step B: 2-Methyl-4- (phenylethynyl) -N- (quinolin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000021
　表１、化合物Ｎｏ．１の合成の段階Ｄにおいて、４－ヨード－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミドの代わりに上記段階で得られたスルホンアミド化合物、トリメチルシリルアセチレンの代わりにフェニルアセチレンを用いることで、表１、化合物Ｎｏ．１７８を合成した。 Table 1, Compound No. In Step D of Synthesis 1, the sulfonamide compound obtained in the above step was used instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and phenylacetylene was used instead of trimethylsilylacetylene. 1, compound no. 178 was synthesized.
　同様の製造法により、表１、化合物Ｎｏ．１７９～２１４を合成した。 According to the same production method, Table 1, Compound No. 179-214 were synthesized.
　なお、５－ブロモピリジン－２－スルホニルクロリド、６－ブロモピリジン－３－スルホニルクロリド、５－ブロモフラン－２－スルホニルクロリド、４－ブロモチオフェン－２－スルホニルクロリド、５－ブロモチアゾール－２－スルホニルクロリドは非特許文献９（Ｓｙｎｌｅｔｔ，２０１１，（８），１１１７．）に記載の方法に準じて対応するジハロへテロ環化合物より製造した。２－クロロピリミジン－５－スルホニルクロリドは特許文献１９（ＷＯ２００６／２９１５４）に記載の方法に準じて２－アミノピリミジンより製造した。３－ブロモチオフェン－２－スルホニルクロリドは特許文献２０（ＷＯ２００４／０７４２３８）に記載の方法に準じて３－ブロモチオフェンより製造した。その他のスルホニルクロリドは市販品を用いた。 5-bromopyridine-2-sulfonyl chloride, 6-bromopyridine-3-sulfonyl chloride, 5-bromofuran-2-sulfonyl chloride, 4-bromothiophene-2-sulfonyl chloride, 5-bromothiazole-2-sulfonyl chloride Was prepared from the corresponding dihaloheterocyclic compound according to the method described in Non-Patent Document 9 (Synlett, 2011, (8), 1117.). 2-Chloropyrimidine-5-sulfonyl chloride was prepared from 2-aminopyrimidine according to the method described in Patent Document 19 (WO 2006/29154). 3-Bromothiophene-2-sulfonyl chloride was produced from 3-bromothiophene according to the method described in Patent Document 20 (WO 2004/074238). Commercially available products were used for the other sulfonyl chlorides.
（９）一般式（Ｉ）においてＡ＝２，４－チアゾール、Ｂ＝Ｃ６Ｈ５、Ｒ１，Ｒ２＝－ＣＨ＝ＣＨ－ＣＨ＝ＣＨ－、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．２１５の合成）
段階Ａ：４－ブロモ－２－（フェニルエチニル）チアゾール (9) In general formula (I), A = 2,4-thiazole, B = C 6 H 5 , R 1 , R 2 = —CH═CH—CH═CH—, R 3 = H, R 4 = H ( Table 1, Synthesis of Compound No. 215)
Step A: 4-Bromo-2- (phenylethynyl) thiazole
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000022
　表１、化合物Ｎｏ．１の合成の段階Ｄにおいて、４－ヨード－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミドの代わりに２，４－ジブロモチアゾール、トリメチルシリルアセチレンの代わりにフェニルアセチレンを用いることで、エチニル化合物を得た。
段階Ｂ：２－（フェニルエチニル）チアゾール－４－スルホニルクロリド Table 1, Compound No. In step D of synthesis 1, ethynyl compound is obtained by using 2,4-dibromothiazole instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide and phenylacetylene instead of trimethylsilylacetylene. It was.
Step B: 2- (Phenylethynyl) thiazole-4-sulfonyl chloride
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000023
　非特許文献９（Ｓｙｎｌｅｔｔ，２０１１，（８），１１１７．）に記載の方法に準じ、上記段階で得られたエチニル化合物よりスルホニルクロリド化合物を得た。
段階Ｃ：２－（フェニルエチニル）－Ｎ－（キノリン－４－イルメチル）チアゾール－４－スルホンアミド A sulfonyl chloride compound was obtained from the ethynyl compound obtained in the above step according to the method described in Non-Patent Document 9 (Synlett, 2011, (8), 1117.).
Step C: 2- (Phenylethynyl) -N- (quinolin-4-ylmethyl) thiazole-4-sulfonamide
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000024
　表１、化合物Ｎｏ．１の合成の段階Ｃにおいて、４－ヨードベンゼンスルホニルクロリドの代わりに上記段階で得られたスルホニルクロリド化合物を用いることで、表１、化合物Ｎｏ．２１５を得た。 Table 1, Compound No. In Step C of the synthesis of Compound 1, the sulfonyl chloride compound obtained in the above step was used in place of 4-iodobenzenesulfonyl chloride, so that Table 1, Compound No. 215 was obtained.
　同様の製造法により、表１、化合物Ｎｏ．２１６，２１７を合成した。 According to the same production method, Table 1, Compound No. 216,217 were synthesized.
（１０）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝Ｃ６Ｈ５、Ｒ１，Ｒ２＝－ＣＨ＝ＣＨ－ＣＨ＝ＣＨ－、Ｒ３＝Ｈ、Ｒ４＝Ｃｌ（表１、化合物Ｎｏ．２１８の合成）
段階Ａ：４－（ブロモメチル）－２－クロロキノリン (10) In the general formula (I), A = 1,4-C 6 H 4 , B = C 6 H 5 , R 1 , R 2 = —CH═CH—CH═CH—, R 3 = H, R 4 = Cl (Table 1, Synthesis of Compound No. 218)
Step A: 4- (Bromomethyl) -2-chloroquinoline
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000025
　四塩化炭素２５．００ｍＬに２－クロロ－４－メチルキノリン２．００ｇ、Ｎ－ブロモスクシンイミド２．１６ｇ、アゾビスイソブチロニトリル１８３ｍｇを加え、８０℃で６時間攪拌した。反応液を室温まで冷却し、水を加え、クロロホルムで抽出した。有機層を硫酸ナトリウムで乾燥し、硫酸ナトリウムをろ過後、有機層を濃縮し、ブロモメチル化合物２．３３ｇを原料との２：１混合物として得た。
段階Ｂ：４－（アジドメチル）－２－クロロキノリン To 25.00 mL of carbon tetrachloride were added 2.00 g of 2-chloro-4-methylquinoline, 2.16 g of N-bromosuccinimide and 183 mg of azobisisobutyronitrile, and the mixture was stirred at 80 ° C. for 6 hours. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, sodium sulfate was filtered off, and the organic layer was concentrated to obtain 2.33 g of bromomethyl compound as a 2: 1 mixture with the raw material.
Step B: 4- (azidomethyl) -2-chloroquinoline
Figure JPOXMLDOC01-appb-C000026
Figure JPOXMLDOC01-appb-C000026
　Ｎ，Ｎ－ジメチルホルムアミド１５．００ｍＬに上記段階で得られたブロモメチル化合物１．６５ｇ、アジ化ナトリウム５８０ｍｇを加え、６０℃で撹拌した。反応液を濃縮し、残渣に水を加え、クロロホルムで抽出した。有機層を硫酸ナトリウムで乾燥し、硫酸ナトリウムをろ過後、有機層を濃縮し、アジド化合物１．３５ｇを得た。
段階Ｃ：（２－クロロキノリン－４－イル）メタンアミン To 15.00 mL of N, N-dimethylformamide were added 1.65 g of the bromomethyl compound obtained in the above step and 580 mg of sodium azide, and the mixture was stirred at 60 ° C. The reaction mixture was concentrated, water was added to the residue, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, sodium sulfate was filtered off, and the organic layer was concentrated to obtain 1.35 g of an azide compound.
Step C: (2-Chloroquinolin-4-yl) methanamine
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000027
　テトラヒドロフラン３０．００ｍＬ、水３．００ｍＬに上記段階で得られたアジド化合物１．３５ｇ、トリフェニルホスフィン１．９４ｇを加え、室温で終夜撹拌した。反応液を濃縮し、残渣をフラッシュ自動精製装置（ｂｉｏｔａｇｅ　ＡＢ社製／ＩｓｏｌｅｒａＴＭ）によるシリカゲルフラッシュクロマトグラフィー（メタノール－クロロホルムで溶出）で精製することによって、メタンアミン化合物２２０ｍｇを得た。
段階Ｄ：Ｎ－（（２－クロロキノリン－４－イル）メチル）－４－ヨードベンゼンスルホンアミド 1.35 g of the azide compound obtained in the above step and 1.94 g of triphenylphosphine were added to 30.00 mL of tetrahydrofuran and 3.00 mL of water, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, and the residue was purified by silica gel flash chromatography (eluted with methanol-chloroform) using a flash automatic purification apparatus (Biotage AB / Isolera ™ ) to obtain 220 mg of a methanamine compound.
Step D: N-((2-chloroquinolin-4-yl) methyl) -4-iodobenzenesulfonamide
Figure JPOXMLDOC01-appb-C000028
Figure JPOXMLDOC01-appb-C000028
　表１、化合物Ｎｏ．１の合成の段階Ｃにおいて、４－（アミノメチル）キノリンの代わりに上記段階で得られたメタンアミン化合物を用いることで、スルホンアミド化合物を得た。
段階Ｅ：Ｎ－（（２－クロロキノリン－４－イル）メチル）－４－（フェニルエチニル）ベンゼンスルホンアミド Table 1, Compound No. In Step C of Synthesis 1, the sulfonamide compound was obtained by using the methanamine compound obtained in the above step instead of 4- (aminomethyl) quinoline.
Step E: N-((2-chloroquinolin-4-yl) methyl) -4- (phenylethynyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000029
Figure JPOXMLDOC01-appb-C000029
　表１、化合物Ｎｏ．１の合成の段階Ｄにおいて、４－ヨード－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミドの代わりに上記段階で得られたスルホンアミド化合物、トリメチルシリルアセチレンの代わりにフェニルアセチレンを用いることで、表１、化合物Ｎｏ．２１８を得た。 Table 1, Compound No. In Step D of Synthesis 1, the sulfonamide compound obtained in the above step was used instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and phenylacetylene was used instead of trimethylsilylacetylene. 1, compound no. 218 was obtained.
（１１）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝Ｈ、Ｒ１＝Ｈ、Ｒ２＝Ｈ、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．２１９の合成）
段階Ａ：４－ヨード－Ｎ－（ピリジン－４－イルメチル）ベンゼンスルホンアミド (11) In general formula (I), A = 1,4-C 6 H 4 , B = H, R 1 = H, R 2 = H, R 3 = H, R 4 = H (Table 1, Compound No. 1). 219)
Step A: 4-Iodo-N- (pyridin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000030
　表１、化合物Ｎｏ．１の合成の段階Ｃにおいて、４－（アミノメチル）キノリンの代わりに４－ピコリルアミンを用いることで、スルホンアミド化合物を得た。
段階Ｂ：Ｎ－（ピリジン－４－イルメチル）－４－（（トリメチルシリル）エチニル）ベンゼンスルホンアミド Table 1, Compound No. In Step C of Synthesis 1, sulfonamide compound was obtained by using 4-picolylamine instead of 4- (aminomethyl) quinoline.
Step B: N- (Pyridin-4-ylmethyl) -4-((trimethylsilyl) ethynyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000031
　表１、化合物Ｎｏ．１の合成の段階Ｄにおいて、４－ヨード－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミドの代わりに上記段階で得られたスルホンアミド化合物を用いることで、トリメチルシリル化合物を得た。
段階Ｃ：４－エチニル－Ｎ－（ピリジン－４－イルメチル）ベンゼンスルホンアミド Table 1, Compound No. In step D of the synthesis of 1, trimethylsilyl compound was obtained by using the sulfonamide compound obtained in the above step instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide.
Step C: 4-Ethynyl-N- (pyridin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-C000032
　表１、化合物Ｎｏ．１の合成の段階Ｅにおいて、Ｎ－（キノリン－４－イルメチル）－４－（（トリメチルシリル）エチニル）ベンゼンスルホンアミドの代わりに上記段階で得られたトリメチルシリル化合物を用いることで、表１、化合物Ｎｏ．２１９を得た。 Table 1, Compound No. In step E of the synthesis of 1, the trimethylsilyl compound obtained in the above step was used in place of N- (quinolin-4-ylmethyl) -4-((trimethylsilyl) ethynyl) benzenesulfonamide. . 219 was obtained.
　同様の製造法により、表１、化合物Ｎｏ．２２０～２２２，２２４～２２６，２３１～２３９，２４３～２５２，２５４～２６３，２６７，２６８，２７２，２７５～２８３，２８８～３０３，３０５～３０８，３１０，３１１，３１６，３１９～３２０を合成した。 According to the same production method, Table 1, Compound No. 220-222,224-226,231-239,243-252,254-263,267,268,272,275-283,288-303,305-308,310,311,316,319-320 were synthesized .
（１２）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝２－ＣＨ２Ｆ－Ｃ６Ｈ４、Ｒ１＝Ｈ、Ｒ２＝Ｈ、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．２２３の合成）
段階Ａ：４－（（２－（フルオロメチル）フェニル）エチニル）－Ｎ－（ピリジン－４－イルメチル）ベンゼンスルホンアミド (12) In general formula (I), A = 1,4-C 6 H 4 , B = 2-CH 2 F—C 6 H 4 , R 1 = H, R 2 = H, R 3 = H, R 4 = H (Table 1, Synthesis of Compound No. 223)
Step A: 4-((2- (Fluoromethyl) phenyl) ethynyl) -N- (pyridin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000033
Figure JPOXMLDOC01-appb-C000033
　表１、化合物Ｎｏ．５の合成の段階Ａにおいて、化合物Ｎｏ．４の代わりに化合物Ｎｏ．２２２を用いることで、表１、化合物Ｎｏ．２２３を得た。 Table 1, Compound No. In step A of the synthesis of compound no. In place of Compound No. 4 222, Table 1, Compound No. 223 was obtained.
　同様の製造法により、表１、化合物Ｎｏ．３１７，３１８を合成した。 According to the same production method, Table 1, Compound No. 317 and 318 were synthesized.
（１３）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝２－ＣＯ２Ｈ－Ｃ６Ｈ４、Ｒ１＝Ｈ、Ｒ２＝Ｈ、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．２２７の合成）
段階Ａ：２－（（４－（Ｎ－（ピリジン－４－イルメチル）スルファモイル）フェニル）エチニル）安息香酸 (13) In the general formula (I), A = 1,4-C 6 H 4 , B = 2-CO 2 H—C 6 H 4 , R 1 = H, R 2 = H, R 3 = H, R 4 = H (Synthesis of Table 1, Compound No. 227)
Step A: 2-((4- (N- (pyridin-4-ylmethyl) sulfamoyl) phenyl) ethynyl) benzoic acid
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-C000034
　表１、化合物Ｎｏ．９の合成の段階Ａにおいて、化合物Ｎｏ．１の代わりに化合物Ｎｏ．２１９を、２－ヨード安息香酸メチルの代わりに２－ヨード安息香酸をそれぞれ用いることで、表１、化合物Ｎｏ．２２７を得た。 Table 1, Compound No. In synthesis step A of compound 9, compound no. In place of Compound No. 1 219 by using 2-iodobenzoic acid in place of methyl 2-iodobenzoate, respectively. 227 was obtained.
　同様の製造法により、表１、化合物Ｎｏ．２２８～２３０，２４０～２４２，２５３，２６４～２６６，２６９～２７１，２７４，２８４～２８７を合成した。 According to the same production method, Table 1, Compound No. 228-230, 240-242, 253, 264-266, 269-271, 274, 284-287 were synthesized.
（１４）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝－（Ｃ＝Ｏ）ＮＨ－ＣＨ＝ＣＨ－ＣＨ＝Ｃ－、Ｒ１＝Ｈ、Ｒ２＝Ｈ、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．２７３の合成）
段階Ａ：４－（（２－オキソ－１，２－ジヒドロピリジン－３－イル）エチニル）－Ｎ－（ピリジン－４－イルメチル）ベンゼンスルホンアミド (14) In general formula (I), A = 1,4-C 6 H 4 , B = — (C═O) NH—CH═CH—CH═C—, R 1 = H, R 2 = H, R 3 = H, R 4 = H (Table 1, Synthesis of Compound No. 273)
Step A: 4-((2-oxo-1,2-dihydropyridin-3-yl) ethynyl) -N- (pyridin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000035
Figure JPOXMLDOC01-appb-C000035
　１，４－ジオキサン１０．００ｍＬに表１、化合物Ｎｏ．２７１のフルオロピリジン化合物７３４ｍｇ、６規定塩酸１０．００ｍＬを加え、１１０℃で９時間攪拌した。反応液に飽和炭酸水素ナトリウム水溶液１００ｍＬ、水酸化ナトリウム２．４０ｇ、水１００ｍＬを加え、溶液を塩基性にした。１０％メタノール－クロロホルムで２回抽出した後、有機層を硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、残渣をフラッシュ自動精製装置（ｂｉｏｔａｇｅ　ＡＢ社製／ＩｓｏｌｅｒａＴＭ）によるシリカゲルフラッシュクロマトグラフィー（メタノール－クロロホルム：２％－２０％で溶出）で精製することによって、表１、化合物Ｎｏ．２７３を得た。 In 10.00 mL of 1,4-dioxane, Table 1, Compound No. 734 mg of 271 fluoropyridine compound and 10.00 mL of 6N hydrochloric acid were added, and the mixture was stirred at 110 ° C. for 9 hours. To the reaction solution, 100 mL of a saturated aqueous sodium hydrogen carbonate solution, 2.40 g of sodium hydroxide and 100 mL of water were added to make the solution basic. After extraction twice with 10% methanol-chloroform, the organic layer was dried over sodium sulfate. After filtering the sodium sulfate, the organic layer was concentrated, and the residue was purified by silica gel flash chromatography (elution with methanol-chloroform: 2% -20%) using a flash automatic purifier (Biotage AB / Isolera ™ ). Table 1, Compound No. 273 was obtained.
（１５）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝（Ｓ）－ＣＨ（ＯＨ）ＣＨ２ＯＨ、Ｒ１＝Ｈ、Ｒ２＝Ｈ、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．３０４の合成）
段階Ａ：（Ｓ）－４－（３，４－ジヒドロキシ－１－ブチン－１－イル）－Ｎ－（ピリジン－４－イルメチル）ベンゼンスルホンアミド (15) In general formula (I), A = 1,4-C 6 H 4 , B = (S) —CH (OH) CH 2 OH, R 1 = H, R 2 = H, R 3 = H, R 4 = H (Synthesis of Table 1, Compound No. 304)
Step A: (S) -4- (3,4-Dihydroxy-1-butyn-1-yl) -N- (pyridin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000036
Figure JPOXMLDOC01-appb-C000036
　１，４－ジオキサン７．００ｍＬに表１、化合物Ｎｏ．３０５のアセトニド化合物５０６ｍｇ、１規定塩酸７．００ｍＬを加え、室温で２時間攪拌した。反応液を濃縮し、残渣に飽和炭酸水素ナトリウム水溶液５０ｍＬと１０％メタノール－クロロホルムを加え、灰白色固体をろ過した。固体をクロロホルム及び水で洗浄し、減圧下乾燥することによって、表１、化合物Ｎｏ．３０４を得た。 In Table 1, compound No. 1 in 7.04 mL of 1,4-dioxane. 506 mg of an acetonide compound of 305, 7.00 mL of 1N hydrochloric acid were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, 50 mL of saturated aqueous sodium hydrogen carbonate solution and 10% methanol-chloroform were added to the residue, and the off-white solid was filtered. The solid was washed with chloroform and water and dried under reduced pressure to give Table 1, Compound No. 304 was obtained.
（１６）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝ＣＯ２Ｅｔ、Ｒ１＝Ｈ、Ｒ２＝Ｈ、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．３０９の合成）
段階Ａ：（４－ヨードフェニル）スルホニル（ピリジン－４－イルメチル）カルバミン酸　ｔｅｒｔ－ブチル (16) In the general formula (I), A = 1,4-C 6 H 4 , B = CO 2 Et, R 1 = H, R 2 = H, R 3 = H, R 4 = H (Table 1, Compound) Synthesis of No. 309)
Step A: (4-Iodophenyl) sulfonyl (pyridin-4-ylmethyl) carbamate tert-butyl
Figure JPOXMLDOC01-appb-C000037
Figure JPOXMLDOC01-appb-C000037
　アセトニトリル１００ｍＬに４－ヨード－Ｎ－（ピリジン－４－イルメチル）ベンゼンスルホンアミド４．００ｇ、二炭酸ジ－ｔｅｒｔ－ブチル２．７７ｇ、Ｎ，Ｎ－ジメチル－４－アミノピリジン６５０ｍｇを加え、室温で４時間撹拌した。反応液に水を加え、白色固体をろ過した。固体を水で洗浄し、減圧下乾燥してカルバミン酸化合物を得た。
段階Ｂ：３－（４－（Ｎ－（ｔｅｒｔ－ブトキシカルボニル）－Ｎ－（ピリジン－４－イルメチル）スルファモイル）フェニル）プロピオール酸エチル To 100 mL of acetonitrile, 4.00 g of 4-iodo-N- (pyridin-4-ylmethyl) benzenesulfonamide, 2.77 g of di-tert-butyl dicarbonate and 650 mg of N, N-dimethyl-4-aminopyridine were added at room temperature. Stir for 4 hours. Water was added to the reaction solution, and the white solid was filtered. The solid was washed with water and dried under reduced pressure to obtain a carbamic acid compound.
Step B: Ethyl 3- (4- (N- (tert-butoxycarbonyl) -N- (pyridin-4-ylmethyl) sulfamoyl) phenyl) propiolate
Figure JPOXMLDOC01-appb-C000038
Figure JPOXMLDOC01-appb-C000038
　表１、化合物Ｎｏ．１の合成の段階Ｄにおいて、４－ヨード－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミドの代わりに上記段階で得られたカルバミン酸化合物を、トリメチルシリルアセチレンの代わりにプロピオール酸エチルを用いることで、プロピオール酸化合物を得た。
段階Ｃ：３－（４－（Ｎ－（ピリジン－４－イルメチル）スルファモイル）フェニル）プロピオール酸エチル Table 1, Compound No. In Step D of Synthesis 1, the carbamic acid compound obtained in the above step was used in place of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and ethyl propiolate was used in place of trimethylsilylacetylene. A propiolic acid compound was obtained.
Step C: ethyl 3- (4- (N- (pyridin-4-ylmethyl) sulfamoyl) phenyl) propiolate
Figure JPOXMLDOC01-appb-C000039
Figure JPOXMLDOC01-appb-C000039
　塩化メチレン１０ｍＬに上記段階で得られたプロピオール酸化合物、トリフルオロ酢酸１０ｍＬを加え、室温で１．５時間攪拌した。反応液を濃縮し、残渣をフラッシュ自動精製装置（ｂｉｏｔａｇｅ　ＡＢ社製／ＩｓｏｌｅｒａＴＭ）によるシリカゲルフラッシュクロマトグラフィー（メタノール－クロロホルムで溶出）で精製することによって、表１、化合物Ｎｏ．３０９を得た。 The propiolic acid compound obtained in the above step and 10 mL of trifluoroacetic acid were added to 10 mL of methylene chloride, and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was concentrated, and the residue was purified by silica gel flash chromatography (eluted with methanol-chloroform) using a flash automatic purifier (Biotage AB / Isolera ™ ). 309 was obtained.
（１７）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝Ｃ（＝ＮＯＣＨ３）ＣＨ３、Ｒ１＝Ｈ、Ｒ２＝Ｈ、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．３１２の合成）
段階Ａ：４－（３－（メトキシイミノ）－１－ブチン－１－イル）－Ｎ－（ピリジン－４－イルメチル）ベンゼンスルホンアミド (17) In general formula (I), A = 1,4-C 6 H 4 , B = C (= NOCH 3 ) CH 3 , R 1 = H, R 2 = H, R 3 = H, R 4 = H (Table 1, Synthesis of Compound No. 312)
Step A: 4- (3- (methoxyimino) -1-butyn-1-yl) -N- (pyridin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000040
Figure JPOXMLDOC01-appb-C000040
　表１、化合物Ｎｏ．１５９の合成の段階Ａにおいて、Ｎｏ．１４１のキノリン化合物の代わりに対応するピリジン化合物を用いることで、表１、化合物Ｎｏ．３１２を得た。 Table 1, Compound No. In step A of the synthesis of 159, no. 141, using the corresponding pyridine compound in place of the quinoline compound of Table 1, compound No. 312 was obtained.
　同様の製造法により、表１、化合物Ｎｏ．３１３～３１５を合成した。 According to the same production method, Table 1, Compound No. 313 to 315 were synthesized.
（１８）一般式（Ｉ）においてＡ＝１，３－Ｃ６Ｈ４、Ｂ＝Ｃ６Ｈ５、Ｒ１＝Ｈ、Ｒ２＝Ｈ、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．３２１の合成）
段階Ａ：３－ブロモ－Ｎ－（ピリジン－４－イルメチル）ベンゼンスルホンアミド (18) In the general formula (I), A = 1,3-C 6 H 4 , B = C 6 H 5 , R 1 = H, R 2 = H, R 3 = H, R 4 = H (Table 1, Synthesis of Compound No. 321)
Step A: 3-Bromo-N- (pyridin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000041
Figure JPOXMLDOC01-appb-C000041
　表１、化合物Ｎｏ．１の合成の段階Ｃにおいて、４－ヨードベンゼンスルホニルクロリドの代わりに３－ブロモベンゼンスルホニルクロリドを、４－（アミノメチル）キノリンの代わりに４－ピコリルアミンを用いることで、スルホンアミド化合物を得た。
段階Ｂ：３－（フェニルエチニル）－Ｎ－（ピリジン－４－イルメチル）ベンゼンスルホンアミド Table 1, Compound No. In Step C of Synthesis 1, the sulfonamide compound was obtained by using 3-bromobenzenesulfonyl chloride in place of 4-iodobenzenesulfonyl chloride and 4-picolylamine in place of 4- (aminomethyl) quinoline. .
Step B: 3- (Phenylethynyl) -N- (pyridin-4-ylmethyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000042
Figure JPOXMLDOC01-appb-C000042
　表１、化合物Ｎｏ．１の合成の段階Ｄにおいて、４－ヨード－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミドの代わりに上記段階で得られたスルホンアミド化合物を、トリメチルシリルアセチレンの代わりにフェニルアセチレンを用いることで、表１、化合物Ｎｏ．３２１を合成した。 Table 1, Compound No. In Step D of Synthesis 1, the sulfonamide compound obtained in the above step was used in place of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and phenylacetylene was used instead of trimethylsilylacetylene. Table 1, Compound No. 321 was synthesized.
　同様の製造法により、表１、化合物Ｎｏ．３２２～３４３，３４７を合成した。 According to the same production method, Table 1, Compound No. 322 to 343,347 were synthesized.
（１９）一般式（Ｉ）においてＡ＝２，４－チアゾール、Ｂ＝Ｃ６Ｈ５、Ｒ１＝Ｈ、Ｒ２＝Ｈ、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．３４６の合成）
段階Ａ：２－（フェニルエチニル）－Ｎ－（ピリジン－４－イルメチル）チアゾール－４－スルホンアミド (19) In general formula (I), A = 2,4-thiazole, B = C 6 H 5 , R 1 = H, R 2 = H, R 3 = H, R 4 = H (Table 1, Compound No. 1). 346)
Step A: 2- (Phenylethynyl) -N- (pyridin-4-ylmethyl) thiazole-4-sulfonamide
Figure JPOXMLDOC01-appb-C000043
Figure JPOXMLDOC01-appb-C000043
　表１、化合物Ｎｏ．２１５の合成の段階Ｃにおいて、４－（アミノメチル）キノリンの代わりに４－ピコリルアミンを用いることで、表１、化合物Ｎｏ．３４６を得た。 Table 1, Compound No. In step C of the synthesis of 215, 4-picolylamine was used in place of 4- (aminomethyl) quinoline, so that Table 1, Compound No. 346 was obtained.
　同様の製造法により、表１、化合物Ｎｏ．３４４，３４５，３４８を合成した。 According to the same production method, Table 1, Compound No. 344, 345, and 348 were synthesized.
　なお、１－（フェニルエチニル）－１Ｈ－ピラゾール－４－スルホニルクロリド非特許文献１２（Ｓｙｎｔｈｅｓｉｓ，２０１１，（５），８１６．）に記載の方法に準じて１－（フェニルエチニル）－１Ｈ－ピラゾールを製造したのち、非特許文献１３（Ｊｏｕｒｎａｌ　ｏｆ　ｃｈｅｍｉｃａｌ　Ｓｏｃｉｅｔｙ（Ｃ），１９６８，１１２０．）に記載の方法に準じて製造した。 1- (Phenylethynyl) -1H-pyrazole-4-sulfonyl chloride According to the method described in Non-Patent Document 12 (Synthesis, 2011, (5), 816.), 1- (phenylethynyl) -1H-pyrazole Was manufactured according to the method described in Non-Patent Document 13 (Journal of chemical Society (C), 1968, 1120.).
（９）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝Ｃ６Ｈ５、Ｒ１＝Ｈ、Ｒ２＝Ｃ６Ｈ５、Ｒ３＝Ｈ、Ｒ４＝Ｈ（表１、化合物Ｎｏ．３４９の合成）
段階Ａ：（２－フェニルピリジン－４－イル）メタノール (9) In general formula (I), A = 1,4-C 6 H 4 , B = C 6 H 5 , R 1 = H, R 2 = C 6 H 5 , R 3 = H, R 4 = H ( Table 1, Synthesis of Compound No. 349)
Step A: (2-Phenylpyridin-4-yl) methanol
Figure JPOXMLDOC01-appb-C000044
Figure JPOXMLDOC01-appb-C000044
　１，４－ジオキサン２０．００ｍＬに（２－ブロモピリジン－４－イル）メタノール１．０ｇ、フェニルボロン酸７７８ｍｇ、テトラキス（トリフェニルホスフィン）パラジウム３０７ｍｇ、炭酸ナトリウム飽和水溶液１０．００ｍＬを加え、１００℃で撹拌した。反応液を室温まで冷却し、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、残渣をフラッシュ自動精製装置（ｂｉｏｔａｇｅ　ＡＢ社製／ＩｓｏｌｅｒａＴＭ）によるシリカゲルフラッシュクロマトグラフィー（酢酸エチル－ヘキサンで溶出）で精製することによって、フェニル化合物９４０ｍｇを得た。
段階Ｂ：４－（アジドメチル）－２－フェニルピリジン To 20.00 mL of 1,4-dioxane, 1.0 g of (2-bromopyridin-4-yl) methanol, 778 mg of phenylboronic acid, 307 mg of tetrakis (triphenylphosphine) palladium, and 10.00 mL of a saturated aqueous solution of sodium carbonate were added, and 100 ° C. Stir with. The reaction was cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. After filtering the sodium sulfate, the organic layer was concentrated, and the residue was purified by silica gel flash chromatography (eluted with ethyl acetate-hexane) using a flash automatic purifier (Biotage AB / Isolera ™ ) to obtain 940 mg of the phenyl compound. Obtained.
Step B: 4- (Azidomethyl) -2-phenylpyridine
Figure JPOXMLDOC01-appb-C000045
Figure JPOXMLDOC01-appb-C000045
　テトラヒドロフラン１０．００ｍＬに上記段階で得られたフェニル化合物９２０ｍｇを加え、溶液を０℃に冷却した。冷却後この溶液に２－アジド－１，３－ジメチルイミダゾリニウムヘキサフルオロホスファート１．７０ｇ、１，８－ジアザビシクロ［５．４．０］ウンデカ－７－エン９６４μＬを加え、室温で１時間撹拌した。反応液に水を加え、濃縮した。残渣に水を加え、ジクロロメタンで抽出した。有機層を硫酸ナトリウムで乾燥し、硫酸ナトリウムをろ過後、有機層を濃縮し、残渣をフラッシュ自動精製装置（ｂｉｏｔａｇｅ　ＡＢ社製／ＩｓｏｌｅｒａＴＭ）によるシリカゲルフラッシュクロマトグラフィー（酢酸エチル－ヘキサンで溶出）で精製することによって、アジド化合物９８０ｍｇを得た。
段階Ｃ：（２－フェニルピリジン－４－イル）メタンアミン To 10.00 mL of tetrahydrofuran was added 920 mg of the phenyl compound obtained in the above step, and the solution was cooled to 0 ° C. To this solution, 1.70 g of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate and 964 μL of 1,8-diazabicyclo [5.4.0] undec-7-ene were added to this solution for 1 hour at room temperature. Stir. Water was added to the reaction solution and concentrated. Water was added to the residue and extracted with dichloromethane. The organic layer was dried over sodium sulfate, the sodium sulfate was filtered, the organic layer was concentrated, and the residue was subjected to silica gel flash chromatography (eluted with ethyl acetate-hexane) with a flash automatic purifier (Biotage AB / Isolera ™ ). By purification, 980 mg of an azide compound was obtained.
Step C: (2-Phenylpyridin-4-yl) methanamine
Figure JPOXMLDOC01-appb-C000046
Figure JPOXMLDOC01-appb-C000046
　テトラヒドロフラン１０．００ｍＬ、水１．００ｍＬに上記段階で得られたアジド化合物９８０ｍｇ、トリフェニルホスフィン１．４７ｇを加え、室温で５時間撹拌した。反応液を濃縮し、残渣をフラッシュ自動精製装置（ｂｉｏｔａｇｅ　ＡＢ社製／ＩｓｏｌｅｒａＴＭ）によるシリカゲルフラッシュクロマトグラフィー（メタノール－クロロホルムで溶出）で精製することによって、メタンアミン化合物８００ｍｇを得た。
段階Ｄ：４－ヨード－Ｎ－（（２－フェニルピリジン－４－イル）メチル）ベンゼンスルホンアミド To 10.00 mL of tetrahydrofuran and 1.00 mL of water were added 980 mg of the azide compound obtained in the above step and 1.47 g of triphenylphosphine, and the mixture was stirred at room temperature for 5 hours. The reaction solution was concentrated, and the residue was purified by silica gel flash chromatography (eluted with methanol-chloroform) using a flash automatic purifier (Biotage AB / Isolera ™ ) to obtain 800 mg of a methanamine compound.
Step D: 4-Iodo-N-((2-phenylpyridin-4-yl) methyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000047
Figure JPOXMLDOC01-appb-C000047
　表１、化合物Ｎｏ．１の合成の段階Ｃにおいて、４－（アミノメチル）キノリンの代わりに上記段階で得られたメタンアミン化合物を用いることで、スルホンアミド化合物を得た。
段階Ｅ：４－（フェニルエチニル）－Ｎ－（（２－フェニルピリジン－４－イル）メチル）ベンゼンスルホンアミド Table 1, Compound No. In Step C of Synthesis 1, the sulfonamide compound was obtained by using the methanamine compound obtained in the above step instead of 4- (aminomethyl) quinoline.
Step E: 4- (Phenylethynyl) -N-((2-phenylpyridin-4-yl) methyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000048
Figure JPOXMLDOC01-appb-C000048
　表１、化合物Ｎｏ．１の合成の段階Ｄにおいて、４－ヨード－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミドの代わりに上記段階で得られたスルホンアミド化合物、トリメチルシリルアセチレンの代わりにフェニルアセチレンを用いることで、表１、化合物Ｎｏ．３４９を得た。 Table 1, Compound No. In Step D of Synthesis 1, the sulfonamide compound obtained in the above step was used instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and phenylacetylene was used instead of trimethylsilylacetylene. 1, compound no. 349 was obtained.
　同様の製造法により、表１、化合物Ｎｏ．３５０～３５９，３６１～３６４を合成した。 According to the same production method, Table 1, Compound No. 350 to 359 and 361 to 364 were synthesized.
　なお、４－（アミノメチル）ピコリノニトリルは非特許文献１０（Ｂｉｏｏｒｇａｎｉｃ＆Ｍｅｄｉｃｉｎａｌ　Ｃｈｅｍｉｓｔｒｙ，２００５，１３，４０２２．）に記載の方法に準じて対応するメチルピリジンより製造した。（２－フルオロピリジン－４－イル）メタンアミンは特許文献２１（ＷＯ２００５／８０３５０）に記載の方法に準じて対応するブロモメチルピリジンより製造した。（３－フルオロピリジン－４－イル）メタンアミンは特許文献２２（ＷＯ２００９／５７８２７）に記載の方法に準じて対応するピリジンカルボアルデヒドより製造した。（３－クロロピリジン－４－イル）メタンアミンは特許文献２５（ＷＯ２０１０／１３２９９９）に記載の方法に準じて対応するメタノールを製造した後、上記記載の方法に準じて製造した。（２－クロロ－６－メチルピリジン－４－イル）メタンアミン、（２，６－ジクロロピリジン－４－イル）メタンアミンは非特許文献１１（Ｔｅｔｒａｈｅｄｒｏｎ，２００７，６３，２９１）に記載の方法に準じて対応するメタノールを製造した後、上記記載の方法に準じて製造した。（３，５－ジクロロピリジン－４－イル）メタンアミンは特許文献２５（ＷＯ２００５／１１６００９）に記載の方法に準じて対応するピリジンカルボアルデヒドより製造した。その他のアミノメチルピリジンは市販品を用いた。 4- (Aminomethyl) picolinonitrile was produced from the corresponding methylpyridine according to the method described in Non-Patent Document 10 (Bioorganic & Medicinal Chemistry, 2005, 13, 4022.). (2-Fluoropyridin-4-yl) methanamine was prepared from the corresponding bromomethylpyridine according to the method described in Patent Document 21 (WO2005 / 80350). (3-Fluoropyridin-4-yl) methanamine was produced from the corresponding pyridinecarbaldehyde according to the method described in Patent Document 22 (WO2009 / 57827). (3-Chloropyridin-4-yl) methanamine was prepared according to the method described above after the corresponding methanol was prepared according to the method described in Patent Document 25 (WO2010 / 132999). (2-Chloro-6-methylpyridin-4-yl) methanamine and (2,6-dichloropyridin-4-yl) methanamine were prepared according to the method described in Non-Patent Document 11 (Tetrahedron, 2007, 63, 291). After the corresponding methanol was produced, it was produced according to the method described above. (3,5-dichloropyridin-4-yl) methanamine was produced from the corresponding pyridinecarbaldehyde according to the method described in Patent Document 25 (WO2005 / 116209). As other aminomethylpyridines, commercially available products were used.
（２１）一般式（Ｉ）においてＡ＝１，４－Ｃ６Ｈ４、Ｂ＝Ｃ６Ｈ５、Ｒ１＝Ｈ、Ｒ２＝ｔｅｒｔ－Ｃ４Ｈ９、Ｒ３＝Ｈ、Ｒ４＝ｔｅｒｔ－Ｃ４Ｈ９（表１、化合物Ｎｏ．３６０の合成）
段階Ａ：４－（ブロモメチル）－２，６－ジ－ｔｅｒｔ－ブチルピリジン (21) In the general formula (I), A = 1,4-C 6 H 4 , B = C 6 H 5 , R 1 = H, R 2 = tert-C 4 H 9 , R 3 = H, R 4 = tert-C 4 H 9 (Synthesis of Table 1, Compound No. 360)
Step A: 4- (Bromomethyl) -2,6-di-tert-butylpyridine
Figure JPOXMLDOC01-appb-C000049
Figure JPOXMLDOC01-appb-C000049
　四塩化炭素５０．００ｍＬに２，６－ジ－ｔｅｒｔ－ブチル－４－メチルピリジン５．００ｇ、Ｎ－ブロモスクシンイミド４．６７ｇ、アゾビスイソブチロニトリル８００ｍｇを加え、６０℃で７時間攪拌した。反応液を室温まで冷却し、水を加え、クロロホルムで抽出した。有機層を硫酸ナトリウムで乾燥し、硫酸ナトリウムをろ過後、有機層を濃縮し、残渣をフラッシュ自動精製装置（ｂｉｏｔａｇｅ　ＡＢ社製／ＩｓｏｌｅｒａＴＭ）によるシリカゲルフラッシュクロマトグラフィーで精製することによって、ブロモメチル化合物０．９６ｇを得た。 To 50.00 mL of carbon tetrachloride, 5.00 g of 2,6-di-tert-butyl-4-methylpyridine, 4.67 g of N-bromosuccinimide, and 800 mg of azobisisobutyronitrile were added and stirred at 60 ° C. for 7 hours. . The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, and after filtering the sodium sulfate, the organic layer was concentrated, and the residue was purified by silica gel flash chromatography using a flash automatic purifier (Biotage AB / Isolera ™ ) to obtain bromomethyl compound 0. .96 g was obtained.
段階Ｂ：４－（アジドメチル）－２，６－ジ－ｔｅｒｔ－ブチルピリジン Step B: 4- (azidomethyl) -2,6-di-tert-butylpyridine
Figure JPOXMLDOC01-appb-C000050
Figure JPOXMLDOC01-appb-C000050
　Ｎ，Ｎ－ジメチルホルムアミド５．００ｍＬに上記段階で得られたブロモメチル化合物０．９５ｇ、アジ化ナトリウム３２６ｍｇを加え、７０℃で撹拌した。反応液を濃縮し、残渣に水を加え、クロロホルムで抽出した。有機層を硫酸ナトリウムで乾燥し、硫酸ナトリウムをろ過後、有機層を濃縮し、アジド化合物８１０ｍｇを得た。
段階Ｃ：（２，６－ジ－ｔｅｒｔ－ブチルピリジン－４－イル）メタンアミン To 5.00 mL of N, N-dimethylformamide were added 0.95 g of the bromomethyl compound obtained in the above step and 326 mg of sodium azide, and the mixture was stirred at 70 ° C. The reaction mixture was concentrated, water was added to the residue, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, sodium sulfate was filtered off, and the organic layer was concentrated to obtain 810 mg of an azide compound.
Step C: (2,6-Di-tert-butylpyridin-4-yl) methanamine
Figure JPOXMLDOC01-appb-C000051
Figure JPOXMLDOC01-appb-C000051
　表１、化合物Ｎｏ．３４９の合成の段階Ｃにおいて、４－（アジドメチル）－２－フェニルピリジンの代わりに上記段階で得られたアジド化合物を用いることで、メタンアミン化合物を得た。
段階Ｄ：Ｎ－（（２，６－ジ－ｔｅｒｔ－ブチルピリジン－４－イル）メチル）－４－ヨードベンゼンスルホンアミド Table 1, Compound No. In Step C of the synthesis of 349, a methanamine compound was obtained by using the azide compound obtained in the above step in place of 4- (azidomethyl) -2-phenylpyridine.
Step D: N-((2,6-di-tert-butylpyridin-4-yl) methyl) -4-iodobenzenesulfonamide
Figure JPOXMLDOC01-appb-C000052
Figure JPOXMLDOC01-appb-C000052
　表１、化合物Ｎｏ．１の合成の段階Ｃにおいて、４－（アミノメチル）キノリンの代わりに上記段階で得られたメタンアミン化合物を用いることで、スルホンアミド化合物を得た。
段階Ｅ：Ｎ－（（２，６－ジ－ｔｅｒｔ－ブチルピリジン－４－イル）メチル）－４－（フェニルエチニル）ベンゼンスルホンアミド Table 1, Compound No. In Step C of Synthesis 1, the sulfonamide compound was obtained by using the methanamine compound obtained in the above step instead of 4- (aminomethyl) quinoline.
Step E: N-((2,6-di-tert-butylpyridin-4-yl) methyl) -4- (phenylethynyl) benzenesulfonamide
Figure JPOXMLDOC01-appb-C000053
Figure JPOXMLDOC01-appb-C000053
　表１、化合物Ｎｏ．１の合成の段階Ｄにおいて、４－ヨード－Ｎ－（キノリン－４－イルメチル）ベンゼンスルホンアミドの代わりに上記段階で得られたスルホンアミド化合物、トリメチルシリルアセチレンの代わりにフェニルアセチレンを用いることで、表１、化合物Ｎｏ．３６０を得た。 Table 1, Compound No. In Step D of Synthesis 1, the sulfonamide compound obtained in the above step was used instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and phenylacetylene was used instead of trimethylsilylacetylene. 1, compound no. 360 was obtained.
　以上のように合成した化合物［Ｉ］、それらの物性及びＮＭＲデータを表１（表１－１～表１－４６）に示す。なお、本明細書中において「表１」とは表１－１ないし表１－４６の総称（包括的名称）である。 The compounds [I] synthesized as described above, their physical properties and NMR data are shown in Table 1 (Table 1-1 to Table 1-46). In this specification, “Table 1” is a generic name (generic name) of Tables 1-1 to 1-46.
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000057
Figure JPOXMLDOC01-appb-T000057
Figure JPOXMLDOC01-appb-T000058
Figure JPOXMLDOC01-appb-T000058
Figure JPOXMLDOC01-appb-T000059
Figure JPOXMLDOC01-appb-T000059
Figure JPOXMLDOC01-appb-T000060
Figure JPOXMLDOC01-appb-T000060
Figure JPOXMLDOC01-appb-T000061
Figure JPOXMLDOC01-appb-T000061
Figure JPOXMLDOC01-appb-T000062
Figure JPOXMLDOC01-appb-T000062
Figure JPOXMLDOC01-appb-T000063
Figure JPOXMLDOC01-appb-T000063
Figure JPOXMLDOC01-appb-T000064
Figure JPOXMLDOC01-appb-T000064
Figure JPOXMLDOC01-appb-T000065
Figure JPOXMLDOC01-appb-T000065
Figure JPOXMLDOC01-appb-T000066
Figure JPOXMLDOC01-appb-T000066
Figure JPOXMLDOC01-appb-T000067
Figure JPOXMLDOC01-appb-T000067
Figure JPOXMLDOC01-appb-T000068
Figure JPOXMLDOC01-appb-T000068
Figure JPOXMLDOC01-appb-T000069
Figure JPOXMLDOC01-appb-T000069
Figure JPOXMLDOC01-appb-T000070
Figure JPOXMLDOC01-appb-T000070
Figure JPOXMLDOC01-appb-T000071
Figure JPOXMLDOC01-appb-T000071
Figure JPOXMLDOC01-appb-T000072
Figure JPOXMLDOC01-appb-T000072
Figure JPOXMLDOC01-appb-T000073
Figure JPOXMLDOC01-appb-T000073
Figure JPOXMLDOC01-appb-T000074
Figure JPOXMLDOC01-appb-T000074
Figure JPOXMLDOC01-appb-T000075
Figure JPOXMLDOC01-appb-T000075
Figure JPOXMLDOC01-appb-T000076
Figure JPOXMLDOC01-appb-T000076
Figure JPOXMLDOC01-appb-T000077
Figure JPOXMLDOC01-appb-T000077
Figure JPOXMLDOC01-appb-T000078
Figure JPOXMLDOC01-appb-T000078
Figure JPOXMLDOC01-appb-T000079
Figure JPOXMLDOC01-appb-T000079
Figure JPOXMLDOC01-appb-T000080
Figure JPOXMLDOC01-appb-T000080
Figure JPOXMLDOC01-appb-T000081
Figure JPOXMLDOC01-appb-T000081
Figure JPOXMLDOC01-appb-T000082
Figure JPOXMLDOC01-appb-T000082
Figure JPOXMLDOC01-appb-T000083
Figure JPOXMLDOC01-appb-T000083
Figure JPOXMLDOC01-appb-T000084
Figure JPOXMLDOC01-appb-T000084
Figure JPOXMLDOC01-appb-T000085
Figure JPOXMLDOC01-appb-T000085
Figure JPOXMLDOC01-appb-T000086
Figure JPOXMLDOC01-appb-T000086
Figure JPOXMLDOC01-appb-T000087
Figure JPOXMLDOC01-appb-T000087
Figure JPOXMLDOC01-appb-T000088
Figure JPOXMLDOC01-appb-T000088
Figure JPOXMLDOC01-appb-T000089
Figure JPOXMLDOC01-appb-T000089
Figure JPOXMLDOC01-appb-T000090
Figure JPOXMLDOC01-appb-T000090
Figure JPOXMLDOC01-appb-T000091
Figure JPOXMLDOC01-appb-T000091
Figure JPOXMLDOC01-appb-T000092
Figure JPOXMLDOC01-appb-T000092
Figure JPOXMLDOC01-appb-T000093
Figure JPOXMLDOC01-appb-T000093
Figure JPOXMLDOC01-appb-T000094
Figure JPOXMLDOC01-appb-T000094
Figure JPOXMLDOC01-appb-T000095
Figure JPOXMLDOC01-appb-T000095
Figure JPOXMLDOC01-appb-T000096
Figure JPOXMLDOC01-appb-T000096
Figure JPOXMLDOC01-appb-T000097
Figure JPOXMLDOC01-appb-T000097
Figure JPOXMLDOC01-appb-T000098
Figure JPOXMLDOC01-appb-T000098
Figure JPOXMLDOC01-appb-T000099
Figure JPOXMLDOC01-appb-T000099
実施例２［製剤例］
製剤例１：乳剤
本発明化合物１０部を、１，２－ジメチル－４－エチルベンゼン４５部および１－メチル－２－ピロリジノン３５部に溶解し、これにソルポール３００５Ｘ（東邦化学工業株式会社製の界面活性剤の商品名）１０部を加え、攪拌混合して１０％乳剤を得た。
製剤例２：水和剤
本発明化合物１０部を、ラウリル硫酸ナトリウム２部、リグニンスルホン酸ナトリウム４部、ホワイトカーボン２０部およびクレー６４部を混合した中に加え、ジュースミキサーで攪拌混合して１０％水和剤を得た。
製剤例３：粒剤
本発明化合物５部に、ドデシルベンゼンスルホン酸ナトリウム２部、カルボキシメチルセルロース２部、ラウリル硫酸ナトリウム２部、ベントナイト１０部およびクレー７９部を加え十分攪拌混合した。適当量の水を加えさらに攪拌し、造粒機で造粒し通風乾燥して５％粒剤を得た。
製剤例４：粉剤
本発化合物１部を大豆油２部に溶解し、ホワイトカーボン５部、酸性リン酸イソプロピル（ＰＡＰ）０．３部およびクレー９１．７部を加え、ジュースミキサーで攪拌混合し、１％粉剤を得た。
製剤例５：フロアブル剤
本発明化合物２０部とポリオキシエチレンアルキルエーテル、ジアルキルスルホサクシネートナトリウムおよび１，２－ベンズイソチアゾリン－３－オンをそれぞれ２部、１部および０．２部含む水２０部を混合しダイノミルを用いて湿式粉砕後、プロピレングリコールおよびキサンタンガムをそれぞれ８部および０．３２部含む水６０部と混合し２０％水中懸濁液を得た。
製剤例６：顆粒水和剤
本発明化合物２０部に、ラウリル硫酸ナトリウム２部、アルキルナフタレンスルホン酸ナトリウム３部、デキストリン５部、ホワイトカーボン２０部、クレー５０部を加え十分攪拌混合した。適当量の水を加えさらに攪拌し、造粒機で造粒し通風乾燥して２０％顆粒水和剤を得た。 Example 2 [Formulation example]
Formulation Example 1: Emulsion 10 parts of the compound of the present invention were dissolved in 45 parts of 1,2-dimethyl-4-ethylbenzene and 35 parts of 1-methyl-2-pyrrolidinone, and this was dissolved in Solpol 3005X (an interface manufactured by Toho Chemical Co., Ltd.). 10 parts of an activator (trade name) was added and mixed by stirring to obtain a 10% emulsion.
Formulation example 2: wettable powder 10 parts of the compound of the present invention was added to a mixture of 2 parts of sodium lauryl sulfate, 4 parts of sodium lignin sulfonate, 20 parts of white carbon and 64 parts of clay. % Wettable powder was obtained.
Formulation Example 3: Granules To 5 parts of the present compound, 2 parts of sodium dodecylbenzenesulfonate, 2 parts of carboxymethylcellulose, 2 parts of sodium lauryl sulfate, 10 parts of bentonite and 79 parts of clay were added and mixed thoroughly. An appropriate amount of water was added and the mixture was further stirred, granulated with a granulator, and dried by ventilation to obtain a 5% granule.
Formulation Example 4: Powder 1 part of the original compound is dissolved in 2 parts of soybean oil, 5 parts of white carbon, 0.3 part of isopropyl acid phosphate (PAP) and 91.7 parts of clay are added, and the mixture is stirred and mixed with a juice mixer. A 1% powder was obtained.
Formulation Example 5: Flowable agent 20 parts of water containing 20 parts of the present compound, 2 parts, 1 part and 0.2 part of polyoxyethylene alkyl ether, sodium dialkylsulfosuccinate and 1,2-benzisothiazolin-3-one, respectively Were mixed with 60 parts of water containing 8 parts and 0.32 parts of propylene glycol and xanthan gum, respectively, to obtain a 20% suspension in water.
Formulation Example 6: Granule wettable powder 2 parts of sodium lauryl sulfate, 3 parts of sodium alkylnaphthalene sulfonate, 5 parts of dextrin, 20 parts of white carbon and 50 parts of clay were added to 20 parts of the compound of the present invention and mixed thoroughly. An appropriate amount of water was added, and the mixture was further stirred, granulated with a granulator, and dried by ventilation to obtain a 20% granular wettable powder.
実施例３［効力試験］
（１）トマト疫病に対する防除効果試験
ポット植えトマト（品種；大型福寿、５．５葉期）に各供試化合物の１０％水和剤を１２５ｐｐｍに調整した薬液（以下供試薬液と称する。）をスプレーガンを用いポット当たり１５ｍｌ散布し、１日後にトマト疫病菌（Phytophthora infestans）の遊走子懸濁液（遊走子濃度１．０×１０４個／ｍｌ）を噴霧接種し、２１℃の湿室条件下に１日置き、さらに温室に３日間置いて十分に発病させた後、各葉の発病程度を調査し、以下の式を用いて防除価を算出した。
防除価の算出；防除価＝{（無処理の発病面積率－処理した薬剤の発病面積率）／無処理の発病面積率}×１００
算出された防除価を下記の基準に従って判定を行った。結果を表２に示す。
防除効果判定　Ａ ： １００％≧防除価≧６０％
防除効果判定　Ｂ ： ６０％＞防除価≧０％ Example 3 [Efficacy test]
(1) Control effect test against tomato plague A potted tomato (variety; large-scale longevity, 5.5 leaf stage) is a chemical solution in which 10% wettable powder of each test compound is adjusted to 125 ppm (hereinafter referred to as a reagent solution). Sprayed with 15 ml per pot using a spray gun, sprayed with a zoospore suspension (Phytophthora infestans) zoospore suspension (sporemide concentration of 1.0 × 10 4 cells / ml) one day later, wet at 21 ° C. After standing for 1 day under room conditions and further in a greenhouse for 3 days to cause sufficient disease, the degree of disease on each leaf was examined, and the control value was calculated using the following formula.
Control value calculation; control value = {(untreated disease area rate−treated drug disease rate) / untreated disease area rate} × 100
The calculated control value was determined according to the following criteria. The results are shown in Table 2.
Control effect judgment A: 100% ≧ control value ≧ 60%
Control effect judgment B: 60%> control value ≧ 0%
Figure JPOXMLDOC01-appb-T000100
Figure JPOXMLDOC01-appb-T000100
（２）キュウリべと病に対する防除効果試験
ポット植えキュウリ（品種；相模半白、２．５葉期）に各供試化合物の１０％水和剤を１２５ｐｐｍに調整した薬液（以下供試薬液と称する。）をスプレーガンを用いポット当たり１５ｍｌ散布し、１日後にキュウリべと病菌（Pseudoperonospora cubensis）の遊走子嚢懸濁液（遊走子嚢濃度１．０×１０４個／ｍｌ）を噴霧接種した。接種後２１℃の湿室条件下に１日置き、更に温室で３日間置いて充分発病させた後、各葉の発病程度を無処理区と対比し、実施例１と同様にして防除効果の判定を行った。結果を表３に示す。 (2) Control effect test for cucumber downy mildew Potato cucumber (variety; Sagamihanjiro, 2.5 leaf stage) 10% wettable powder of each test compound adjusted to 125 ppm (hereinafter referred to as reagent solution and Sprayed 15 ml per pot using a spray gun, and one day later sprayed with a zoospore suspension (Pseudoperonospora cubensis) zoospore sac suspension (zoospore sac concentration 1.0 × 10 4 cells / ml) did. After inoculation, leave under a humid chamber condition at 21 ° C. for 1 day, and after leaving it in a greenhouse for 3 days to cause sufficient disease, the degree of disease on each leaf is compared with that of the untreated group, and the control effect is the same as in Example 1. Judgment was made. The results are shown in Table 3.
Figure JPOXMLDOC01-appb-T000101
Figure JPOXMLDOC01-appb-T000101
（３）キュウリうどんこ病に対する防除効果試験
ポット植えキュウリ（品種；相模半白、２．０葉期）に各供試化合物の１０％水和剤を１２５ｐｐｍに調整した薬液（以下供試薬液と称する。）をスプレーガンを用いポット当たり１５ｍｌ散布し、１日後にキュウリうどんこ病菌（Sphaerotheca cucurbitae）の分生子懸濁液（分生子濃度１．０×１０５個／ｍｌ）を噴霧接種した。温室で１４日間置いて充分発病させた後、各葉の発病程度を無処理区と対比し、実施例１と同様にして防除効果の判定を行った。結果を表４に示す。 (3) Control effect test for cucumber powdery mildew Potted cucumber (variety; Sagamihanjiro, 2.0 leaf stage) 10% wettable powder of each test compound adjusted to 125 ppm (hereinafter referred to as reagent solution and 15 ml per pot using a spray gun, and one day later, a conidia suspension (conidia concentration of 1.0 × 10 5 cells / ml) of Sphaerotheca cucurbitae was spray-inoculated. After sufficient disease was established in a greenhouse for 14 days, the degree of disease on each leaf was compared with the untreated group, and the control effect was determined in the same manner as in Example 1. The results are shown in Table 4.
Figure JPOXMLDOC01-appb-T000102
Figure JPOXMLDOC01-appb-T000102
（４）ワタアブラムシに対する効力試験
直径３ｃｍのキュウリ葉片をプラスチックカップ内の湿らせたスポンジ上に置き、ワタアブラムシ（Aphis gossypii）成虫５頭を放飼し、一晩静置の後、産仔幼虫数を計数した。表１記載化合物の１０％水和剤を２５０ｐｐｍに希釈調製した薬液０．４ｍｌずつを散布し、二日後に死亡虫数を調査して死亡率を算出した。死亡率が５０％以上をＡ、同５０％未満をＢと判定した。結果を表５に示す。 (4) Efficacy test against cotton aphids Place a 3 cm diameter cucumber leaf piece on a moist sponge in a plastic cup, release 5 adult cotton aphids (Aphis gossypii), leave them overnight, and then lay larvae Numbers were counted. 0.4 ml of a chemical solution prepared by diluting a 10% wettable powder of the compounds shown in Table 1 to 250 ppm was sprayed, and the number of dead insects was investigated two days later to calculate the mortality rate. A mortality rate of 50% or more was determined as A, and a mortality rate of less than 50% was determined as B. The results are shown in Table 5.
Figure JPOXMLDOC01-appb-T000103
Figure JPOXMLDOC01-appb-T000103
（５）ハスモンヨトウに対する効力試験
直径３ｃｍのハクサイ葉片を、表１記載化合物の１０％水和剤を２５０ｐｐｍに希釈調製した薬液に浸漬処理した後風乾させ、プラスチックシャーレに収容して、ハスモンヨトウ（Spodptera litura）１令幼虫１０頭を放飼した。処理二日後の死亡虫数を調査して死亡率を算出した。死亡率が５０％以上をＡ、同５０％未満をＢと判定した。結果を表６に示す。 (5) Efficacy test against Spodoptera litura 3 cm diameter Chinese cabbage leaf pieces were immersed in a chemical solution prepared by diluting 10% wettable powder of the compounds shown in Table 1 to 250 ppm, then air-dried, housed in a plastic petri dish, and Spodptera litura ) 10 1st instar larvae were released. The mortality was calculated by examining the number of dead worms two days after treatment. A mortality rate of 50% or more was determined as A, and a mortality rate of less than 50% was determined as B. The results are shown in Table 6.
Figure JPOXMLDOC01-appb-T000104
Figure JPOXMLDOC01-appb-T000104
　式［Ｉ］で示される本発明の新規化合物は、特に農園芸用植物を冒す病原菌、昆虫、ダニ、線虫などの有害生物に対して優れた防除活性を示すので、新たな農薬として極めて有用である。 
  Since the novel compound of the present invention represented by the formula [I] exhibits an excellent control activity against pests such as pathogens, insects, mites, nematodes and the like that particularly affect agricultural and horticultural plants, it is extremely useful as a new agricultural chemical. It is.

Claims (19)

  1. 　次式［Ｉ］：
    Figure JPOXMLDOC01-appb-C000001
     ［式中Ｒ１、Ｒ２、Ｒ３、Ｒ４は、各々水素原子、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数3～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル、ハロアルケニル、ハロアルコキシ、アシルアルコキシ、アシルオキシアルキル、アルキルスルホニルアルキル、シロキシアルキル、ヒドロキシアルキル、アルコキシアルキル、ハロアルコキシアルキル、アルキルチオアルキル、ジアルコキシアセタール、アルコキシアルコキシ、シアノアルキル、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）又は、Ｒ１とＲ２が結合してピリジン環上の炭素原子と共に形成するチオフェン環、ピリジン環、ピロール環、イミダゾール環、ベンゼン環、ナフタレン環、ピリミジン環、フラン環、ピラジン環、ピラゾール環、オキサゾール環を表し、
    Ａは、フェニレン、５若しくは６員環のヘテロアレンジイル（ヘテロアレンは１－３個のＮ、Ｏ、Ｓ原子を環に含み、また、フェニレン、ヘテロアレンジイルのいずれも、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数3～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル、ハロアルケニル、ハロアルコキシ、アシルアルコキシ、アシルオキシアルキル、アルキルスルホニルアルキル、シロキシアルキル、ヒドロキシアルキル、アルコキシアルキル、ハロアルコキシアルキル、アルキルチオアルキル、ジアルコキシアセタール、アルコキシアルコキシ、シアノアルキル、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）から選択する１ないし４個の置換基で置換されていてもよい）を表し、
    Ｂは
    ａ）フェニル、ベンジル、オキサゾリル、イソキサゾリル、フリル、ベンゾフリル、イソベンゾフリル、ジヒドロベンゾフリル、チアゾリル、イソチアゾリル、ナフチル、ピリミジニル、ピラジニル、キノキサリル、キナゾリル、ピリジル、キノリル、イソキノリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ピロリル、インドリル、イソインドリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、チエニル、ベンゾチエニル、イミダゾリル、ベンズイミダゾリル、ピラゾリル、ピリドニル、トリアジニル、トリアゾリル、チアジアゾリル、オキサジアゾリル、テトラゾリル、フェロセニルから成る群より選択される、０～3個のヘテロ原子を場合によっては含有する単環式もしくは二環式の環、
    ｂ）炭素原子数１～６の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８の直鎖状又は分岐状のシクロアルキルまたは炭素原子数３～８のシクロアルケニル、
    ｃ）－ＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）、
    ｄ）－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニル、ベンジルまたは環状エーテルである）、ハロゲン、ホルミル（－ＣＨＯ）またはカルボキシル（－ＣＯＯＨ）、
    ｅ）水素原子
    から選択され、ａ）、ｂ）の場合Ｂは－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）Ｒ、－Ｒ、－ＯＲ、－ＳＲ、－ＳＯ２Ｒ、－ＯＣ（Ｏ）Ｒ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、－ＮＨＲ、－ＮＲ２、－ＮＨＣ（Ｏ）Ｒ、－ＮＲＣ（Ｏ）Ｒ、－ＮＨＣ（Ｏ）ＯＲ、－ＮＲＣ（Ｏ）ＯＲ、－Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、－ＮＨＳＯ２Ｒ、－ＮＲＳＯ２Ｒ、＝ＮＯＲ、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数3～８のシクロアルキル、炭素原子数３～８のシクロアルケニルまたは環状エーテルである）、－ＳｉＲ５Ｒ６Ｒ７、－ＯＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル、ハロアルケニル、ハロアルコキシ、ハロアルキルチオ、アシルアルコキシ、アシルオキシアルキル、アルキルスルホニルアルキル、シロキシアルキル、ヒドロキシアルキル、アルコキシアルキル、ハロアルコキシアルキル、アルキルチオアルキル、ジアルコキシアセタール、アルコキシアルコキシ、シアノアルキル、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（－ＣＨＯ）、カルボキシル（－ＣＯＯＨ）、オキソ（＝Ｏ）から選択する１ないし７個の置換基で置換されていても良い。］
    で示されるスルホンアミド化合物。     Formula [I]:
    Figure JPOXMLDOC01-appb-C000001
     [Wherein R 1 , R 2 , R 3 , R 4 are each a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R , —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, or linear or branched alkynyl having 2 to 8 carbon atoms. Or a cycloalkyl having 3 to 8 carbon atoms or a cycloalkenyl having 3 to 8 carbon atoms), —SiR 5 R 6 R 7 , —OS iR 5 R 6 R 7 (R 5 , R 6 , R 7 is linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and two or all of them may be the same substituent or all different substituents. Good), haloalkyl, haloalkenyl, haloalkoxy, acylalkoxy, acyloxyalkyl, alkylsulfonylalkyl, siloxyalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, dialkoxyacetal, alkoxyalkoxy, cyanoalkyl, halogen, cyano , Nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoo Sazoriru, Benzookisoriru, imide, formyl (-CHO), a carboxyl (-COOH) or thiophene ring to form together with the carbon atoms on the pyridine with R 1 and R 2 bond ring, pyridine ring, pyrrole ring, an imidazole ring, a benzene Represents a ring, naphthalene ring, pyrimidine ring, furan ring, pyrazine ring, pyrazole ring, oxazole ring,
    A is phenylene, 5- or 6-membered heteroarrangeyl (heteroarene contains 1-3 N, O, S atoms in the ring, and both phenylene and heteroarrangeyl are —C (O) OR , —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, — NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (wherein R is linear or branched alkyl having 1 to 8 carbon atoms, and having 2 to 8 carbon atoms) Linear or branched alkenyl, linear or branched alkynyl having 2 to 8 carbon atoms or carbon atom Number 3 is a cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms in ~ 8), - SiR 5 R 6 R 7, -OSiR 5 R 6 R 7 (R 5, R 6, R 7 is C 1 -C To 6 linear or branched alkyls, phenyls, two or all of which may be the same or different, and haloalkyl, haloalkenyl, haloalkoxy, acylalkoxy, acyloxyalkyl, alkylsulfonylalkyl , Siloxyalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, dialkoxyacetal, alkoxyalkoxy, cyanoalkyl, halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, Pi Substituted with 1 to 4 substituents selected from lysyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH) May represent)
    B is a) phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzoisothiazolyl , Pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl, ferrocenyl A monocyclic or bicyclic ring optionally containing 0 to 3 heteroatoms,
    b) linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, Linear or branched cycloalkyl having 3 to 8 carbon atoms or cycloalkenyl having 3 to 8 carbon atoms,
    c) —SiR 5 R 6 R 7 (R 5 , R 6 , R 7 are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, and even if two or all are the same substituents, all Different substituents may be used),
    d) —C (O) OR, —C (O) NHR, —C (O) NR 2 , —SO 2 NHR, —SO 2 NR 2 (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon having 3 to 8 carbon atoms C 3 -C 8 cycloalkenyl, benzyl or cyclic ether), halogen, formyl (—CHO) or carboxyl (—COOH),
    e) selected from hydrogen atoms, and in the case of a) and b) B is —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, ═NOR, —SO 2 NHR, —SO 2 NR 2 (where R is linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, or linear or branched alkynyl having 2 to 8 carbon atoms. Or a cycloalkyl having 3 to 8 carbon atoms, a cycloalkenyl having 3 to 8 carbon atoms or a cyclic ether), —SiR 5 R 6 R 7 , —OSiR 5 R 6 R 7 (R 5 , R 6 , R 7 are linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and two or all of them may be the same substituent. All may be different substituents), haloalkyl, haloalkenyl, haloalkoxy, haloalkylthio, acylalkoxy, acyloxyalkyl, alkylsulfonylalkyl, siloxyalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, dialkoxyacetal, Alkoxyalkoxy, cyanoalkyl, halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, It may be substituted with 1 to 7 substituents selected from thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH), and oxo (═O). ]
    A sulfonamide compound represented by:
  2. 　Ａが、無置換、または１～４個の置換基を有しているフェニレンである、請求項１に記載の化合物。 2. The compound according to claim 1, wherein A is unsubstituted or phenylene having 1 to 4 substituents.
  3. 　Ａが、オキサゾールジイル、イソキサゾールジイル、フランジイル、チアゾールジイル、イソチアゾールジイル、ピリミジンジイル、ピラジンジイル、ピリジンジイル、ピロールジイル、チオフェンジイル、イミダゾールジイル、ピラゾールジイルから成る群より選択されるヘテロアレンジイルであり、ここで、ヘテロアレンジイルが無置換、または１～７個の置換基を有する、請求項１に記載の化合物。 A is a heteroarrangeyl selected from the group consisting of oxazolediyl, isoxazolediyl, frangiyl, thiazolediyl, isothiazolediyl, pyrimidinediyl, pyrazinediyl, pyridinediyl, pyrrolediyl, thiophenediyl, imidazolediyl, pyrazolediyl The compound of claim 1, wherein heteroarendyl is unsubstituted or has 1 to 7 substituents.
  4. 　Ｂが、フェニル、フリル、チアゾリル、ナフチル、ピリジル、キノリル、チエニル、イミダゾリル、ピラゾリル、テトラゾリルから成る群より選択される、単環式もしくは二環式の環である、請求項１～３のいずれか１項に記載の化合物。 Any one of claims 1 to 3, wherein B is a monocyclic or bicyclic ring selected from the group consisting of phenyl, furyl, thiazolyl, naphthyl, pyridyl, quinolyl, thienyl, imidazolyl, pyrazolyl, tetrazolyl. The compound according to item 1.
  5. 　Ｂが、炭素原子数１～６の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、または炭素原子数３～８の直鎖状又は分岐状のシクロアルキルである、請求項１～３のいずれか１項に記載の化合物。 B is linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, or linear or branched having 3 to 8 carbon atoms. The compound according to any one of claims 1 to 3, which is cycloalkyl.
  6. 　Ｂが、－ＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）である、請求項１～３のいずれか１項に記載の化合物。 B is —SiR 5 R 6 R 7 (R 5 , R 6 , R 7 are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, and two or all of them may be the same substituents. The compound according to any one of claims 1 to 3, wherein may be different substituents.
  7. 　Ｂが、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニル、ベンジルまたは環状エーテルである）、ハロゲン、ホルミル（－ＣＨＯ）またはカルボキシル（－ＣＯＯＨ）である、請求項１～３のいずれか１項に記載の化合物。 B is —C (O) OR, —C (O) NHR, —C (O) NR 2 , —SO 2 NHR, —SO 2 NR 2 (wherein R is a direct number of 1 to 8 carbon atoms) Chain or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, or The compound according to any one of claims 1 to 3, which is cycloalkenyl, benzyl or cyclic ether having 3 to 8 carbon atoms), halogen, formyl (-CHO) or carboxyl (-COOH).
  8. 　Ｂが、フェニル、フリル、チアゾリル、ナフチル、ピリジル、キノリル、チエニル、イミダゾリル、ピラゾリル、テトラゾリルから成る群より選択される、単環式もしくは二環式の環であり、Ｒ１、Ｒ２、Ｒ３、Ｒ４が、各々水素原子、－Ｒ、－ＯＲ、－ＳＲ（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数3～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、ハロアルキル、ハロアルコキシ、ハロゲン、シアノ、ニトロ、ヒドロキシ、フェニル、フェノキシである、請求項１～３のいずれか１項に記載の化合物。 B is a monocyclic or bicyclic ring selected from the group consisting of phenyl, furyl, thiazolyl, naphthyl, pyridyl, quinolyl, thienyl, imidazolyl, pyrazolyl, tetrazolyl, R 1 , R 2 , R 3 , R 4 are each a hydrogen atom, —R, —OR, —SR (where R is linear or branched alkyl having 1 to 8 carbon atoms, linear having 2 to 8 carbon atoms) Or a branched alkenyl, a linear or branched alkynyl having 2 to 8 carbon atoms, a cycloalkyl having 3 to 8 carbon atoms, or a cycloalkenyl having 3 to 8 carbon atoms), haloalkyl, haloalkoxy, The compound according to any one of claims 1 to 3, which is halogen, cyano, nitro, hydroxy, phenyl, phenoxy.
  9. 　Ｂが、炭素原子数１～６の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、または炭素原子数３～８の直鎖状又は分岐状のシクロアルキルであり、Ｒ１、Ｒ２、Ｒ３、Ｒ４が、各々水素原子、－Ｒ、－ＯＲ、－ＳＲ（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数3～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、ハロアルキル、ハロアルコキシ、ハロゲン、シアノ、ニトロ、ヒドロキシ、フェニル、又はフェノキシである、請求項１～３のいずれか１項に記載の化合物。 B is linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, or linear or branched having 3 to 8 carbon atoms. R 1 , R 2 , R 3 , R 4 are each a hydrogen atom, —R, —OR, —SR (where R is a linear or branched group having 1 to 8 carbon atoms) Alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, or 3 to 3 carbon atoms The compound according to any one of claims 1 to 3, which is haloalkyl, haloalkoxy, halogen, cyano, nitro, hydroxy, phenyl, or phenoxy.
  10. 　Ｂが、－ＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）であり、Ｒ１、Ｒ２、Ｒ３、Ｒ４が、各々水素原子、－Ｒ、－ＯＲ、－ＳＲ（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数3～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、ハロアルキル、ハロアルコキシ、ハロゲン、シアノ、ニトロ、ヒドロキシ、フェニル、又はフェノキシである、請求項１～３のいずれか１項に記載の化合物。 B is —SiR 5 R 6 R 7 (R 5 , R 6 , R 7 are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, and two or all of them may be the same substituents. R 1 , R 2 , R 3 , and R 4 are each a hydrogen atom, —R, —OR, —SR (wherein R is a straight chain having 1 to 8 carbon atoms). Chain or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms, or The compound according to any one of claims 1 to 3, which is cycloalkenyl having 3 to 8 carbon atoms), haloalkyl, haloalkoxy, halogen, cyano, nitro, hydroxy, phenyl, or phenoxy.
  11. 　Ｂが、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニル、ベンジルまたは環状エーテルである）、ハロゲン、ホルミル（－ＣＨＯ）またはカルボキシル（－ＣＯＯＨ）であり、Ｒ１、Ｒ２、Ｒ３、Ｒ４が、各々水素原子、－Ｒ、－ＯＲ、－ＳＲ（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル又は炭素原子数3～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニルである）、ハロアルキル、ハロアルコキシ、ハロゲン、シアノ、ニトロ、ヒドロキシ、フェニル、又はフェノキシである、請求項１～３のいずれか１項に記載の化合物。 B is —C (O) OR, —C (O) NHR, —C (O) NR 2 , —SO 2 NHR, —SO 2 NR 2 (wherein R is a direct number of 1 to 8 carbon atoms) Chain or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, or C 3-8 cycloalkenyl, benzyl or cyclic ether), halogen, formyl (—CHO) or carboxyl (—COOH), and each of R 1 , R 2 , R 3 and R 4 is a hydrogen atom , -R, -OR, -SR (wherein R is linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, carbon atom) 2-8 linear or branched alkynyl or 3 carbon atoms A haloalkyl, a haloalkoxy, a halogen, a cyano, a nitro, a hydroxy, a phenyl, or a phenoxy. The described compound.
  12. 　Ｂが、フェニル、フリル、チアゾリル、ナフチル、ピリジル、キノリル、チエニル、イミダゾリル、ピラゾリル、テトラゾリルから成る群より選択される、単環式もしくは二環式の環であり、Ｒ１がＲ２と結合してピリジン環上の炭素原子と共に形成するベンゼン環である、請求項１～３のいずれか１項に記載の化合物。 B is a monocyclic or bicyclic ring selected from the group consisting of phenyl, furyl, thiazolyl, naphthyl, pyridyl, quinolyl, thienyl, imidazolyl, pyrazolyl, tetrazolyl, and R 1 is bonded to R 2. The compound according to any one of claims 1 to 3, which is a benzene ring formed together with a carbon atom on the pyridine ring.
  13. 　Ｂが、炭素原子数１～６の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、または炭素原子数３～８の直鎖状又は分岐状のシクロアルキルであり、Ｒ１がＲ２と結合してピリジン環上の炭素原子と共に形成するベンゼン環である、請求項１～３のいずれか１項に記載の化合物。 B is linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, or linear or branched having 3 to 8 carbon atoms. The compound according to any one of claims 1 to 3, wherein the compound is cycloalkyl, and R 1 is a benzene ring that is bonded to R 2 to form together with a carbon atom on the pyridine ring.
  14. Ｂが、－ＳｉＲ５Ｒ６Ｒ７（Ｒ５、Ｒ６、Ｒ７は炭素原子数１～６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）であり、Ｒ１がＲ２と結合してピリジン環上の炭素原子と共に形成するベンゼン環である、請求項１～３のいずれか１項に記載の化合物。 B is —SiR 5 R 6 R 7 (R 5 , R 6 , R 7 are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, and two or all of them may be the same substituents. The compound according to any one of claims 1 to 3, wherein R 1 is a benzene ring formed by combining with R 2 together with a carbon atom on the pyridine ring.
  15. 　Ｂが、－Ｃ（Ｏ）ＯＲ、－Ｃ（Ｏ）ＮＨＲ、－Ｃ（Ｏ）ＮＲ２、－ＳＯ２ＮＨＲ、－ＳＯ２ＮＲ２（ここでのＲは、炭素原子数１～８の直鎖状又は分岐状のアルキル、炭素原子数２～８の直鎖状又は分岐状のアルケニル、炭素原子数２～８の直鎖状又は分岐状のアルキニル、炭素原子数３～８のシクロアルキルまたは炭素原子数３～８のシクロアルケニル、ベンジルまたは環状エーテルである）、ハロゲン、ホルミル（－ＣＨＯ）またはカルボキシル（－ＣＯＯＨ）であり、Ｒ１がＲ２と結合してピリジン環上の炭素原子と共に形成するベンゼン環である、請求項１～３のいずれか１項に記載の化合物。 B is —C (O) OR, —C (O) NHR, —C (O) NR 2 , —SO 2 NHR, —SO 2 NR 2 (wherein R is a direct number of 1 to 8 carbon atoms) Chain or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, or C 3-8 cycloalkenyl, benzyl or cyclic ether), halogen, formyl (—CHO) or carboxyl (—COOH), and R 1 is bonded to R 2 together with the carbon atom on the pyridine ring The compound according to any one of claims 1 to 3, which is a benzene ring to be formed.
  16. 　式［ＩＩ］で示されるスルホン酸誘導体と、式［ＩＩＩ］で示されるアミン誘導体を塩基（base）および溶媒の存在下反応させることを特徴とする請求項１記載の式［Ｉ］で示されるスルホンアミド誘導体の製造方法。
    Figure JPOXMLDOC01-appb-C000002
     　（式中、Ｒ１，Ｒ２，Ｒ３，Ｒ４，Ａ及びＢは、請求項１に記載した意味を有する。）     The sulfonic acid derivative represented by the formula [II] and the amine derivative represented by the formula [III] are reacted in the presence of a base and a solvent. A method for producing a sulfonamide derivative.
    Figure JPOXMLDOC01-appb-C000002
     (In the formula, R 1 , R 2 , R 3 , R 4 , A and B have the meanings described in claim 1).
  17. 　式［Ｉ‐１］で示される末端アルキンに、カップリング反応を利用して置換基を導入する事を特徴とする請求項１記載の式［Ｉ］で示されるスルホンアミド誘導体の製造方法。
    Figure JPOXMLDOC01-appb-C000003
     　（式中、Ｘは臭素またはヨウ素、Ｂはフェニル、ヘテロアリール、アルケニル、Ｒ１，Ｒ２，Ｒ３，Ｒ４及びＡは、請求項１に記載した意味を有する。）     The method for producing a sulfonamide derivative represented by the formula [I] according to claim 1, wherein a substituent is introduced into the terminal alkyne represented by the formula [I-1] using a coupling reaction.
    Figure JPOXMLDOC01-appb-C000003
     (Wherein X is bromine or iodine, B is phenyl, heteroaryl, alkenyl, R 1 , R 2 , R 3 , R 4 and A have the meanings given in claim 1)
  18. 　式［Ｉ－２］で示される化合物と末端アルキン［Ｖ］から、カップリング反応を利用して置換基を導入する事を特徴とする請求項１記載の式［Ｉ］で示されるスルホンアミド誘導体の製造方法。
    Figure JPOXMLDOC01-appb-C000004
     　（式中、Ｘは臭素またはヨウ素、Ｒ１，Ｒ２，Ｒ３，Ｒ４，Ａ及びＢは、請求項１に記載した意味を有する。）     The sulfonamide derivative represented by the formula [I] according to claim 1, wherein a substituent is introduced from the compound represented by the formula [I-2] and the terminal alkyne [V] using a coupling reaction. Manufacturing method.
    Figure JPOXMLDOC01-appb-C000004
     (In the formula, X is bromine or iodine, R 1 , R 2 , R 3 , R 4 , A and B have the meanings described in claim 1).
  19. 　請求項１に記載の式［Ｉ］で示されるスルホンアミド誘導体を有効成分として１種若しくは２種以上含む有害生物防除剤。
          A pest control agent comprising one or more sulfonamide derivatives represented by the formula [I] according to claim 1 as an active ingredient.
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